WO2020251049A1

WO2020251049A1 - Polycyclic aromatic compound

Info

Publication number: WO2020251049A1
Application number: PCT/JP2020/023312
Authority: WO
Inventors: 琢次畠山; 馬場　大輔; 亮介川角; 笹田　康幸; 詠希町田; 田中　裕之; 一雄奥村; 靖宏近藤
Original assignee: 学校法人関西学院; Jnc株式会社
Priority date: 2019-06-14
Filing date: 2020-06-12
Publication date: 2020-12-17
Also published as: KR20220024468A; TW202104239A; JPWO2020251049A1; CN114026147A

Abstract

Provided by the present invention is a polycyclic aromatic compound represented by formula (1), or a polymer thereof. The compound according to the present invention can be used in an organic device such as an organic EL element. (In formula (1), rings A, B and C are optionally substituted aryl rings or heteroaryl rings, at least one ring selected from the group consisting of ring A, ring B, and ring C is a condensed ring formed from two or more rings selected from the group consisting of an aryl ring, a heteroaryl ring, and a cyclopentadiene ring, Y¹ is B or the like, X¹ and X² are >N-R (R being an aryl or the like), rings A, B, C, etc. can be condensed by a cycloalkane or the like, and the hydrogen in formula (1) can be substituted by deuterium, cyano or halogen.)

Description

Polycyclic aromatic compounds

The present invention relates to polycyclic aromatic compounds. The present invention also relates to an organic electroluminescent device, an organic field effect transistor and an organic thin-film solar cell using the polycyclic aromatic compound, and a display device and a lighting device.

Conventionally, display devices using electroluminescent devices that emit electroluminescence have been studied in various ways because they can save power and become thinner. Further, organic electroluminescent devices made of organic materials (“organic EL devices” in the present specification. "Or simply referred to as" element ".) Has been actively studied because it is easy to reduce the weight and size. In particular, the development of organic materials having light emitting characteristics such as blue, which is one of the three primary colors of light, and the development of organic materials having charge transporting ability such as holes and electrons (which have the potential to become semiconductors and superconductors). Regarding development, both high molecular weight compounds and low molecular weight compounds have been actively studied so far.

The organic EL element has a structure composed of a pair of electrodes composed of an anode and a cathode, and one layer or a plurality of layers containing an organic compound, which are arranged between the pair of electrodes. Layers containing organic compounds include light emitting layers and charge transport / injection layers that transport or inject charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

As a material for a light emitting layer, for example, a benzofluorene compound or the like has been developed (Patent Document 1). Further, as a hole transport material, for example, a triphenylamine compound or the like has been developed (Patent Document 2). Further, as an electron transport material, for example, an anthracene-based compound and the like have been developed (Patent Document 3).

Further, in recent years, a material having an improved triphenylamine derivative has been reported as a material used for an organic EL element or an organic thin-film solar cell (Patent Document 4). This material is based on N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD), which has already been put into practical use. It is a material characterized in that its flatness is improved by connecting aromatic rings constituting triphenylamine. In this document, for example, the charge transport property of a NO-linking compound (Compound 1 on page 63) is evaluated, but a method for producing a material other than the NO-linking compound is not described, and the element to be linked is not described. Since the electronic state of the entire compound is different if they are different, the properties obtained from materials other than the NO-linking compound are not yet known. Other examples of such compounds can be found (Patent Document 5). For example, a compound having a conjugated structure having a large triplet exciton energy (T1) is useful as a material for a blue light emitting layer because it can emit phosphorescence having a shorter wavelength. Further, as an electron transport material or a hole transport material that sandwiches the light emitting layer, a compound having a novel conjugated structure having a large T1 is required.

The host material of the organic EL element is generally a molecule in which a plurality of existing aromatic rings such as benzene and carbazole are linked by a single bond or a phosphorus atom or a silicon atom. This is because the large HOMO-LUMO gap (bandgap Eg in the thin film) required for the host material is secured by connecting a large number of relatively small aromatic rings of the conjugated system. In addition, the host material of the organic EL element using a phosphorescent material or a heat activated delayed fluorescent material, high triplet excitation energy (E _T) is also required, the donor or acceptor properties of the aromatic ring and substituents in the molecule by connecting, to localize the SOMO1 and SOMO2 triplet excited state (T1), by reducing the exchange interaction between the two trajectories, it is possible to improve the triplet excitation energy (E _T) It becomes. However, the small aromatic ring of the conjugated system does not have sufficient redox stability, and the device using the molecule connecting the existing aromatic ring as the host material does not have a sufficient life. On the other hand, polycyclic aromatic compounds having an extended π conjugated system, generally, but the redox stability is excellent, because HOMO-LUMO gap and triplet excitation energy (band gap Eg of the thin film) (E _T) is low, It has been considered unsuitable for host materials.

International Publication No. 2004/061047 Japanese Unexamined Patent Publication No. 2001-172232 Japanese Unexamined Patent Publication No. 2005-170911 International Publication No. 2012/118164 International Publication No. 2011/107186 International Publication No. 2015/102118

As described above, various materials have been developed as materials used for organic EL devices, but in order to increase the choices of materials for organic EL devices, it is desired to develop a material made of a compound different from the conventional one. There is. In particular, the organic EL properties obtained from materials other than the NO-linking compounds reported in Patent Documents 1 to 4 and the method for producing the same are not yet known.

Further, Patent Document 6 reports a polycyclic aromatic compound containing boron and an organic EL device using the same, but in order to further improve the device characteristics, light emission efficiency and device life can be improved. There is a demand for layer materials, especially dopant materials.

As a result of diligent studies to solve the above problems, the present inventors have used a polycyclic aromatic compound having a structure in which a fused ring is further introduced as a material for a light emitting layer in the polycyclic aromatic compound described in Patent Document 6. It has been found that the light emission efficiency and the device life can be improved by configuring the organic EL element. The present invention is a completion of the present invention based on this finding.
Specifically, the present invention has the following configuration.

<1> A multimer of a polycyclic aromatic compound represented by the following formula (1) or a polycyclic aromatic compound having a plurality of structures represented by the following formula (1).

(In equation (1),
Rings A, B, and C are independently aryl rings or heteroaryl rings, and at least one hydrogen in these rings may be substituted, provided that rings A, B, and C are substituted. At least one ring selected from the group consisting of is a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring. At least one hydrogen in this fused ring may be substituted.
Rings B and C may be attached via a single bond or a linking group.
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is aryl, alkyl, or Cycloalkyl,
X ¹ and X ² are independently>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R. R is hydrogen, optionally substituted aryl (except amino as a substituent), optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. Yes, the R of> Si (-R) ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or substituted. The R of> C (-R) ₂ may be an independently hydrogen, an aryl which may be substituted, a heteroaryl which may be substituted, an alkyl which may be substituted, and the like. Alternatively, it is a cycloalkyl which may be substituted, and the two Rs of> Si (-R) ₂ and> C (-R) ₂ may be bonded to each other to form a ring, and the above> N R in at least one of -R,> Si (-R) ₂ , and> C (-R) ₂ is bonded to at least one ring of the A ring, B ring, and C ring by a linking group or a single bond. May be
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by the formula (1) may be condensed with at least one cycloalkane, and at least one in the cycloalkane. Hydrogen may be substituted and at least one -CH _2- in the cycloalkane may be substituted with -O-.
At least one hydrogen in the compound or structure represented by the formula (1) may be substituted with deuterium, cyano, or halogen. )

<2> At least one ring selected from the group consisting of A ring, B ring and C ring is a fused ring which is a heteroaryl ring containing a sulfur atom or an oxygen atom, and at least one hydrogen in this fused ring is May be replaced,
The polycyclic aromatic compound according to <1> or a multimer thereof.

<3> The polycyclic aromatic compound according to <1> or <2>, wherein at least one ring selected from the group consisting of A ring, B ring and C ring is a ring represented by the formula (BHet) or That multimer.

(In the formula (BHet), R ^a1 to R ^a6 are hydrogens or substituents, except that any two or three of R ^a1 to R ^a6 adjacent to each other are Y ¹ and Y ¹ in the formula (1). It becomes a bond with X ¹ and / or X ^2, and X is>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C (-R) ₂ , and the above> The Rs of NR,> Si (-R) ₂ , or> C (-R) ₂ are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, substituted, respectively. It is an alkyl which may be an alkyl or a cycloalkyl which may be substituted, and the two Rs of> Si (-R) ₂ and> C (-R) ₂ may be bonded to each other to form a ring. Good.)

<4> At least one ring selected from the group consisting of the B ring and the C ring is a ring represented by the formula (BHet).
In the formula (BHet), any two adjacent R ^a1 to R ^a6 serve as a bond with Y ¹ and X ¹ or X ² in the formula (1).
Others ^Ra1 to ^Ra6 are hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl hetero. Arylamino, substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted. Alkoxy, substituted or unsubstituted aryloxy, or substituted silyl,
In the ring A and the rings B and C that are not fused rings, the substituents in which the hydrogen of the aryl ring or the heteroaryl ring may be substituted are substituted or unsubstituted aryl, substituted or unsubstituted hetero. Aryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino, substituted or unsubstituted diarylboryl (two aryls via a single bond or a linking group). One selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, and substituted silyl. That's it,
Rings A, B, and C all include a 5- or 6-membered ring that shares a bond with the central condensed 2-ring structure of formula (1) composed of Y ¹ , X ¹ , and X ² .
Rings B and C may be bonded via a single bond,>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S or> Se, as described above. > N-R and> Si (-R) ₂ R may be independently substituted with hydrogen, alkyl or cycloalkyl, or heteroaryl, alkyl or cycloalkyl, respectively. Alkyl or cycloalkyl, wherein the> C (-R) ₂ R may be substituted with hydrogen, alkyl or cycloalkyl, or heteroaryl, alkyl or cycloalkyl. It is cycloalkyl, and the R in at least one of>N-R,> Si (-R) ₂ and> C (-R) ₂ is -O-, -S-, -C (-R). _It may be bonded to at least one ring of the B ring and the C ring by a _2- or a single bond, and the R of the -C (-R) _2- is hydrogen, alkyl, or cycloalkyl, and the said. The two Rs> Si (-R) ₂ and> C (-R) ₂ may be combined with each other to form a ring.
X ¹ and X ² are independently>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R. And> Si (-R) ₂ R may be independently substituted with an aryl, alkyl or cycloalkyl optionally substituted with hydrogen, alkyl or cycloalkyl, heteroaryl, alkyl, or cyclo, respectively. The R of> C (-R) ₂ is alkyl, optionally substituted with hydrogen, alkyl or cycloalkyl, and optionally substituted with aryl, alkyl or cycloalkyl, heteroaryl, alkyl, or cycloalkyl. The two Rs of> Si (-R) ₂ and> C (-R) ₂ may be bonded to each other to form a ring, and the above-mentioned> N-R and> Si (-R) may be formed. ) ₂ and> R in at least one of C (-R) ₂ are -O-, -S-, -C (-R) _2- , or by a single bond, the A ring, B ring, and C. It may be attached to at least one ring of the ring, wherein the -C (-R) _2- R is hydrogen, alkyl, or cycloalkyl.
In the case of a multimer, it is a dimer or trimer having two or three structures represented by the formula (1).
The polycyclic aromatic compound according to <3> or a multimer thereof.

<5> The polycyclic aromatic compound or a multimer thereof according to <3> or <4>, which contains at least one tertiary-alkyl represented by the following formula (tR).

(In the formula (tR), ^Ra , R ^b, and R ^c are independently alkyl having 1 to 24 carbon atoms, and any -CH _{2- in the} alkyl may be substituted with -O-. , * Is the connection position.)

<6> also ^{X 1} and ^{X 2} are both a> N-R, at least one R of> N-R in ^{which X 1} and ^{X 2} may be the have also be 2-biphenylyl or substituted with substituted The polycyclic aromatic compound according to any one of <3> to <5>, which is terphenyl-2'-yl, or a multimer thereof.
<7> At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by the formula (1) is condensed with at least one cycloalkane, and at least one in the cycloalkane. The polycyclic aromatic according to any one of <3> to <6>, wherein one hydrogen may be substituted, and at least one -CH _2- in the cycloalkane may be substituted with -O-. A compound or a multimer thereof.

<8> In <1> or <2> represented by the following formulas (2), (3), (4), (5), (6), (7), (8), or (9). The polycyclic aromatic compound described or a multimer thereof.

(In equations (2), (3), (4), (5), (6), (7), (8), and (9),
R ¹ to R ¹⁷ , R ²¹ to R ²⁴ , R ³¹ to R ³⁴ , and R ⁴¹ to R ⁴⁴ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino, respectively. , Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyls, in which at least one hydrogen is aryl, heteroaryl may be substituted by alkyl or cycloalkyl, or together with a ring adjacent groups are bonded to one of R 1 ^~ R ^3, is adjacent groups of R 8 ^~ R ¹¹ Adjacent groups of R ⁴ to R ⁷ are bonded to each other together with the b ring to bond with the c ring, and adjacent groups of R ¹² to R ¹⁴ are bonded to each other with the a12 ring to form R ¹⁵ to. Adjacent groups of R ¹⁷ are bonded to each other with the b15 ring, and adjacent groups of R ²¹ to R ²⁴ are bonded to each other with the c21 ring, and adjacent groups of R ³¹ to R ³⁴ are bonded to each other. They may be combined to form an aryl ring or a heteroaryl ring, respectively, with the b31 ring and with the adjacent groups of R ⁴¹ to R ⁴⁴ bonded together with the b41 ring, at least in the formed ring. One hydrogen can be aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl. , Alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen in these is aryl, heteroaryl, alkyl, or. May be substituted with cycloalkyl
However, in the formula (2), at least one set of two adjacent groups of R ¹ to R ¹¹ are combined to form a divalent group represented by the formula (Het). R ⁴ and R ⁵ and R ⁶ and R ⁷ do not simultaneously constitute a divalent group represented by the formula (Het), and R ⁸ and R ⁹ and R ¹⁰ and R ¹¹ simultaneously formulate. It does not constitute a divalent group represented by (Het), and in the formula (7), at least one set of two adjacent groups of R ¹ to R ³ and R ⁹ to R ¹⁷ Is combined to form a divalent group represented by the formula (Het).
In formula (Het), R ^b1 and R ^b2 are hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are attached via a single bond or a linking group). Can be), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, where * is. Represents the bond position
X is independently>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C (-R) ₂ , and the above-mentioned>N-R,> Si ( _{-R) 2,} or> C _{(-R) 2} of R each independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, wherein> Si _{(-R) 2,} and> C (-R ) The _two Rs of 2 may be combined with each other to form a ring.
R ⁷ and R ⁸ in formula (2), R ⁸ and R ²⁴ in formula (3), or R ³⁴ and R ²⁴ in formula (5) are combined to form a single bond,>O,>NR,>. Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se may be set, and the R of> N-R and> Si (-R) ₂ may be independent of each other. Hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the R of> C (-R) ₂ is , Hydrogen, aryl with 6 to 12 carbons, heteroaryl with 2 to 15 carbons, alkyl with 1 to 6 carbons, or cycloalkyl with 3 to 14 carbons, said> Si (-R) ₂ , and. The two Rs of> C (-R) ₂ may be combined with each other to form a ring, and at least one of the above-mentioned>N-R,> Si (-R) ₂ and> C (-R) ₂ . R in one is bonded to at least one of the b ring, b31 ring, c ring, and c21 ring by an -O-, -S-, -C (-R) _2- , or a single bond. Well,
Y ¹ is independently B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is Aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms.
X ¹ , X ² , X ³ , and X ⁴ are independent of>O,>NR,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se, respectively. Yes, the R of> N-R and> Si (-R) ₂ are independently hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, and 2 to 2 carbon atoms which may be substituted. 15 heteroaryl, optionally substituted alkyl having 1 to 6 carbon atoms, or optionally substituted cycloalkyl having 3 to 14 carbon atoms, wherein R of> C (-R) ₂ is hydrogen. , An aryl having 6 to 12 carbon atoms which may be substituted, a heteroaryl which may have 2 to 15 carbon atoms which may be substituted, an alkyl having 1 to 6 carbon atoms which may be substituted, or an alkyl having 1 to 6 carbon atoms which may be substituted. It is a good cycloalkyl having 3 to 14 carbon atoms, and the two Rs of> Si (-R) ₂ and> C (-R) ₂ may be bonded to each other to form a ring, and the above> R in at least one of NR,> Si (-R) ₂ , and> C (-R) ₂ is by -O-, -S-, -C (-R) _2- , or a single bond. It may be bonded to at least one ring of a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, a 5-membered ring, a b31 ring, and a b41 ring.
Selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9). At least one of them may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 30 carbon atoms and 2 to 30 carbon atoms. Heteroaryl, alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms may be substituted, and at least one -CH _2- in the cycloalkane may be substituted with -O-. Often,
At least one hydrogen in the compound represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9) is deuterium, cyano,. Alternatively, it may be replaced with halogen. )

<9> R ¹ to R ¹⁷ , R ²¹ to R ²⁴ , R ³¹ to R ³⁴ , and R ⁴¹ to R ⁴⁴ are independently hydrogen, aryl with 6 to 30 carbon atoms, and 2 to 30 carbon atoms, respectively. Heteroaryl, diarylamino (where aryl is aryl with 6-12 carbon atoms), diarylboryl (where aryl is aryl with 6-12 carbon atoms, the two aryls are attached via a single bond or a linking group. (May be), alkyl with 1 to 24 carbon atoms, cycloalkyl or trialkylsilyl with 3 to 24 carbon atoms (where alkyl is alkyl with 1 to 6 carbon atoms), and adjacent to R ¹ to R ^3. The groups are bonded to each other together with the a ring, the adjacent groups of R ⁸ to R ¹¹ are bonded to each other to form the b ring, and the adjacent groups of R ⁴ to R ⁷ are bonded to each other together with the c ring. , R ¹² to R ¹⁴ adjacent groups are bonded to the a12 ring, and R ¹⁵ to R ¹⁷ adjacent groups are bonded to the b15 ring, and R ²¹ to R ²⁴ are adjacent to each other. The groups are bonded together with the c21 ring, the adjacent groups of R ³¹ to R ³⁴ are bonded together with the b31 ring, and the adjacent groups of R ⁴¹ to R ⁴⁴ are bonded together with the b41 ring. , Each may form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen in the formed ring is an aryl ring having 6 to 10 carbon atoms and having 6 to 10 carbon atoms, respectively. It may be substituted with an alkyl of 1 to 12, a cycloalkyl of 3 to 16 carbon atoms or a trialkylsilyl (where alkyl is an alkyl having 1 to 4 carbon atoms).
In the formula (Het), R ^b1 and R ^b2 are hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diallylamino (where aryl is an aryl having 6 to 12 carbon atoms), and a diallylboryl (whereever Aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or It is a trialkylsilyl (although alkyl is an alkyl having 1 to 6 carbon atoms).
X is independently>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C (-R) ₂ , and the above-mentioned>N-R,> Si ( -R) ₂ or> C (-R) ₂ R is an aryl with 6 to 30 carbon atoms, a heteroaryl with 2 to 30 carbon atoms, an alkyl with 1 to 24 carbon atoms, or a cycloalkyl with 3 to 24 carbon atoms. And
R ⁷ and R ⁸ or R ¹⁵ and R ¹⁶ may be combined to form>O,>N-R,> C (-R) ₂ , or> S, as described above> N-R. Is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and R of> C (-R) ₂ is hydrogen and an aryl having 6 to 10 carbon atoms. , An alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
Y ¹ is B, P, P = O, P = S, or Si-R, and R of the Si-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a carbon number of carbon atoms. 5-10 cycloalkyl,
X ¹ , X ² , X ³ and X ⁴ are independently>O,>N-R,> C (-R) ₂ , or> S, and R in> N-R is replaced. Aryl having 6 to 10 carbon atoms which may be substituted, alkyl having 1 to 4 carbon atoms which may be substituted, or cycloalkyl having 5 to 10 carbon atoms which may be substituted, and the above-mentioned> C (-. R) ₂ R is a hydrogen, an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
Selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), and (9). At least one of the compounds may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 16 carbon atoms and 2 to 22 carbon atoms. Heteroaryl, alkyl having 1-12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms may be substituted.
At least one hydrogen in the compound represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9) is deuterium, cyano,. Alternatively, the polycyclic aromatic compound according to <8>, which may be substituted with halogen, or a multimer thereof.

<10> The polycyclic aromatic compound or a multimer thereof according to <8> or <9>, which contains at least one tertiary-alkyl represented by the following formula (tR).

<11> formula (2), (3), (4), (5), and ^{X 1} and ^{X 2} as well as the formula (7) in (6), ^X 1, ^{X 2} in (8), and (9) , X ³ and X ⁴ are all> N-R, and R may be substituted 2-biphenylyl or optionally substituted terphenyl-as X ¹ , X ² , X ³ or X ^4. The polycyclic aromatic compound according to any one of <8> to <10> or a multimer thereof, which comprises at least one 2'-yl> NR.
<12> Consists of an aryl ring and a heteroaryl ring in the compound represented by the formula (2), (3), (4), (5), (6), (7), (8), or (9). At least one selected from the group is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH _2- in the cycloalkane is-. The polycyclic aromatic compound according to any one of <8> to <11>, which may be substituted with O−, or a multimer thereof.

<13> The polycyclic aromatic according to <1> or <2>, wherein at least one ring selected from the group consisting of A ring, B ring, and C ring is a ring represented by the formula (DBHet). A compound or a multimer thereof.

(In the formula (DBHet), R ^a11 to R ^a18 are hydrogens or substituents, except that any two or three of R ^a11 to R ^a18 adjacent to each other are Y ¹ and Y ¹ in the formula (1). It becomes a bond with X ¹ and / or X ^2, and X is>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C (-R) ₂ , and the above> R of NR,> Si (-R) ₂ , or> C (-R) ₂ is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, Alternatively, it is a cycloalkyl which may be substituted, and the two Rs of> Si (-R) ₂ and> C (-R) ₂ may be bonded to each other to form a ring.)

<14> at least one ring selected from ring B and the group consisting of C ring is a ring represented by the formula ^(DBHet), one of ^R a11 ^~ R ^a18, two or adjacent the formula ( 1) Becomes a bond with Y ¹ and X ¹ or X ² in
In formula (DBHet), other ^R a11 ^{~ R a18} is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted di-heteroarylamino, Substituent or unsubstituted aryl heteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted. Cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl.
The substituents of the aryl ring or the heteroaryl ring in the ring A and the rings B and C which are not the fused rings may be substituted or unsubstituted aryl, substituted or unsubstituted hetero. Aryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino, substituted or unsubstituted diarylboryl (two aryls via a single bond or a linking group). One selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, and substituted silyl. That's it,
Rings A, B, and C all include a 5- or 6-membered ring that shares a bond with the central condensed 2-ring structure of formula (1) composed of Y ¹ , X ¹ , and X ² .
Rings B and C may be bonded via a single bond,>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se. The> N-R and> Si (-R) ₂ R may be independently substituted with aryl, alkyl or cycloalkyl optionally substituted with hydrogen, alkyl or cycloalkyl, respectively. , Alkyl, or cycloalkyl, wherein R of> C (-R) ₂ is aryl, which may be substituted with hydrogen, alkyl or cycloalkyl, or heteroaryl, which may be substituted with alkyl or cycloalkyl. It is alkyl or cycloalkyl, and the two Rs of> Si (-R) ₂ and> C (-R) ₂ may be bonded to each other to form a ring, and the above> NR, The R in at least one of> Si (-R) ₂ and> C (-R) ₂ is -O-, -S-, -C (-R) _2- , or the B ring and C by a single bond. It may be attached to at least one ring of the ring, wherein the -C (-R) _2- R is hydrogen, alkyl, or cycloalkyl.
X ¹ and X ² are independently>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R. And> Si (-R) ₂ R may be independently substituted with an aryl, alkyl or cycloalkyl optionally substituted with hydrogen, alkyl or cycloalkyl, heteroaryl, alkyl, or cyclo, respectively. The R of> C (-R) ₂ is alkyl, optionally substituted with hydrogen, alkyl or cycloalkyl, and optionally substituted with aryl, alkyl or cycloalkyl, heteroaryl, alkyl, or cycloalkyl. The two Rs of> Si (-R) ₂ and> C (-R) ₂ may be bonded to each other to form a ring, and the above-mentioned> N-R and> Si (-R) may be formed. ) ₂ and> R in at least one of C (-R) ₂ are -O-, -S-, -C (-R) _2- , or by a single bond, the A ring, B ring, and C. It may be attached to at least one ring of the ring, wherein the -C (-R) _2- R is hydrogen, alkyl, or cycloalkyl.
In the case of a multimer, it is a dimer or trimer having two or three structures represented by the formula (1).
The polycyclic aromatic compound according to <13> or a multimer thereof.

<15> The polycyclic aromatic compound or a multimer thereof according to <13> or <14>, which comprises at least one tertiary-alkyl represented by the following formula (tR).

<16> ^{X 1} and ^{X 2} both are> N-R, ^X at least one R ¹ and at the ^{X 2>} N-R may be a not also be 2-biphenylyl or substituted with substituted The polycyclic aromatic compound according to any one of <13> to <15>, which is terphenyl-2'-yl, or a multimer thereof.
<17> At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by the formula (1) is condensed with at least one cycloalkane, and at least one in the cycloalkane. The polycyclic aromatic according to any one of <13> to <16>, wherein one hydrogen may be substituted, and at least one -CH _2- in the cycloalkane may be substituted with -O-. A compound or a multimer thereof.

<18> In <1> or <2> represented by the following formulas (12), (13), (14), (15), (16), (17), (18), or (19). The polycyclic aromatic compound described or a multimer thereof.

(In equations (12), (13), (14), (15), (16), (17), (18), (19), and (20),
R ¹ ~ ^{R 3} and ^R 8 ^{~ R 11} are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, Jiariruboriru (two aryl is a single bond or a linking group (May be bonded via), alkyl, alkoxy, aryloxy, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen is aryl, heteroaryl, May be substituted with alkyl or cycloalkyl,
R ⁵¹ to R ⁵⁸ and R ⁶¹ to R ⁶⁸ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded or linking groups). (May be bonded via), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Often,
Adjacent groups of R ¹ to R ³ are bonded to each other to form a ring, and adjacent groups of R ⁸ to R ¹¹ are bonded to each other to form a ring b, which are adjacent to each other of R ⁵¹ to R ^54. The groups are bonded together with the c51 ring, the adjacent groups of R ⁵⁵ to R ⁵⁸ are bonded together with the c55 ring, and the adjacent groups of R ⁶¹ to R ⁶⁴ are bonded together with the b61 ring. And adjacent groups of R ⁶⁵ to R ⁶⁸ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b65 ring, respectively, and at least one hydrogen in the formed ring is an aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diallylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or It may be substituted with a substituted silyl,
X is independently>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C (-R) ₂ , and the above-mentioned>N-R,> Si ( -R) ₂ or> C (-R) ₂ R are independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, respectively, and> Si (-R) ₂ and> C (-R). _{The two} Rs of 2 may be combined with each other to form a ring.
Y ¹ is independently B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is It is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.
X ¹ and X ² are independently>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R. And> R of Si (-R) ₂ are independently hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, a heteroaryl having 2 to 15 carbon atoms which may be substituted, respectively. It is an alkyl having 1 to 6 carbon atoms which may be present, or a cycloalkyl having 3 to 14 carbon atoms which may be substituted, and R of> C (−R) ₂ may be hydrogen or substituted. An aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted, an alkyl having 1 to 6 carbon atoms which may be substituted, or an alkyl having 3 to 14 carbon atoms which may be substituted. It is a cycloalkyl, and the two Rs of> Si (-R) ₂ and> C (-R) ₂ may be bonded to each other to form a ring, and the above>N-R,> Si ( The R in at least one of -R) ₂ and> C (-R) ₂ is -O-, -S-, -C (-R) _2- or by a single bond, a ring, b ring, c51 ring, And may be associated with at least one ring of the b61 ring.
From aryl and heteroaryl rings in compounds represented by formulas (12), (13), (14), (15), (16), (17), (18), (19), or (20). At least one selected from the group may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl or carbon having 6 to 30 carbon atoms. It may be substituted with a heteroaryl of number 2 to 30, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH _2- in the cycloalkane is substituted with -O-. May have been
At least one hydrogen in the compounds represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19), and (20) is deuterium. It may be substituted with hydrogen, cyano, or halogen. )
^<19> ^R 1 ~ R ³ and ^R 8 ^{- R 11} are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl of 2-30 carbon atoms, diarylamino (where aryl is C 6-30 12 aryls), diarylboryls (where aryls are aryls with 6-12 carbon atoms, and the two aryls may be attached via a single bond or linking group), or alkyls with 1-24 carbon atoms. Yes,
R ⁵¹ to R ⁵⁸ and R ⁶¹ to R ⁶⁸ are independently hydrogen, aryl with 6 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, and diarylamino (where aryl is aryl with 6 to 12 carbon atoms). ), Diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, and 3 to 24 carbon atoms. Twenty-four cycloalkyls, or trialkylsilyls (where alkyls are alkyls with 1-6 carbon atoms).
Adjacent groups of R ¹ to R ³ are bonded to each other to form a ring, and adjacent groups of R ⁸ to R ¹¹ are bonded to each other to form a ring b, which are adjacent to each other of R ⁵¹ to R ^54. The groups are bonded together with the c51 ring, the adjacent groups of R ⁵⁵ to R ⁵⁸ are bonded together with the c55 ring, and the adjacent groups of R ⁶¹ to R ⁶⁴ are bonded together with the b61 ring. and adjacent groups together with binding to b65 ring of R ^{65 ~} R ^68, respectively, may form a heteroaryl ring of aryl or C 6-15 carbon atoms 9-16, formed At least one hydrogen in the ring is aryl with 6 to 10 carbon atoms, alkyl with 1 to 12 carbon atoms, or cycloalkyl or trialkylsilyl with 3 to 16 carbon atoms (where alkyl is alkyl with 1 to 4 carbon atoms). ) May be replaced
X is independently>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C (-R) ₂ , and the above-mentioned>N-R,> Si ( -R) ₂ or> C (-R) ₂ R is an aryl with 6 to 30 carbon atoms, a heteroaryl with 2 to 30 carbon atoms, an alkyl with 1 to 24 carbon atoms, or a cycloalkyl with 3 to 24 carbon atoms. And
Y ¹ is B, P, P = O, P = S or Si-R, and R of the Si-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or 5 carbon atoms. ~ 10 cycloalkyl,
X ¹ and X ² are independently>O,>N-R,> C (-R) ₂ , or> S, where R in> N-R may be substituted carbon. Aryl of number 6 to 10, alkyl having 1 to 4 carbon atoms which may be substituted, or cycloalkyl having 5 to 10 carbon atoms which may be substituted, and R of> C (-R) ₂ is , Hydrogen, aryl with 6 to 10 carbon atoms, alkyl with 1 to 4 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms.
From aryl and heteroaryl rings in compounds represented by formulas (12), (13), (14), (15), (16), (17), (18), (19), and (20). At least one selected from the group may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl or carbon having 6 to 16 carbon atoms. It may be substituted with a heteroaryl of number 2 to 22, an alkyl of 1 to 12 carbons, or a cycloalkyl of 3 to 16 carbons.
At least one hydrogen in the compound represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19), or (20) is deuterium. The polycyclic aromatic compound or a multimer thereof according to <18>, which may be substituted with hydrogen, cyano, or halogen.

<20> The polycyclic aromatic compound or a multimer thereof according to <18> or <19>, which comprises at least one tertiary alkyl represented by the following formula (tR).

<21> also ^{X 1} and ^{X 2} are both a> N-R, at least one R of> N-R in ^{which X 1} and ^{X 2} may be the have also be 2-biphenylyl or substituted with substituted The polycyclic aromatic compound according to any one of <18> to <20>, which is terphenyl-2'-yl, or a multimer thereof.
<22> Consists of an aryl ring and a heteroaryl ring in the compound represented by the formula (12), (13), (14), (15), (16), (17), (18), or (19). At least one selected from the group is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH _2- in the cycloalkane is-. The polycyclic aromatic compound according to any one of <18> to <21> or a multimer thereof, which may be substituted with O−.
<23> The polycyclic aromatic according to any one of <1> to <7> and <13> to <17>, wherein the A ring is a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring. A group compound or a multimer thereof.
<24> The polycyclic aromatic compound according to any one of <1> to <23>, in which Y ¹ is B, or a multimer thereof.

<25> The polycyclic according to any one of <1> to <24>, wherein R contains at least one> NR, which is X ¹ , X ² , X ³ or X ⁴ , and R is any of the following groups. A ring aromatic compound or a multimer thereof.

(Me indicates methyl, tBu indicates t-butyl, * indicates the binding position.)

<26> The polycyclic aromatic compound according to any one of <1> to <25>, or a multimer thereof, wherein the halogen is fluorine.

<27> The polycyclic aromatic compound according to <1> or a multimer thereof, which is represented by any of the following structural formulas.

(In the above structural formula, "D" indicates deuterium, "Me" indicates methyl, "tBu" indicates t-butyl, and "tAm" indicates t-amyl.)

<28> The polycyclic aromatic compound according to <1> or a multimer thereof, which is represented by any of the following structural formulas.

(In the above structural formula, "Me" indicates methyl and "tBu" indicates t-butyl.)

<29> The polycyclic aromatic compound according to <1> or a multimer thereof, which is represented by any of the following structural formulas.

<30> A reactive compound in which the polycyclic aromatic compound according to any one of <1> to <29> or a multimer thereof is substituted with a reactive substituent.
<31> A polymer compound obtained by polymerizing the reactive compound according to <30> as a monomer, or a polymer crosslinked product obtained by further cross-linking the polymer compound.
<32> A pendant type polymer compound in which the main chain type polymer is substituted with the reactive compound according to <30>, or a pendant type polymer crosslinked product in which the pendant type polymer compound is further crosslinked.
<33> A material for an organic device containing the polycyclic aromatic compound according to any one of <1> to <29> or a multimer thereof.
<34> A material for an organic device containing the reactive compound according to <30>.
<35> A material for an organic device containing the polymer compound or polymer crosslinked product according to <34>.
<36> A material for an organic device containing the pendant type polymer compound or the pendant type polymer crosslinked body according to <32>.
<37> The material for an organic device according to any one of <33> to <36>, wherein the material for the organic device is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell. ..
<38> The material for an organic device according to <37>, wherein the material for the organic electroluminescent element is a material for a light emitting layer.
<39> A composition containing the polycyclic aromatic compound according to any one of <1> to <32> or a multimer thereof, and an organic solvent.
<40> A composition containing the reactive compound according to <30> and an organic solvent.
<41> A composition containing a main chain polymer, the reactive compound according to <33>, and an organic solvent.
<42> A composition containing the polymer compound or polymer crosslinked product according to <31> and an organic solvent.
<43> A composition containing the pendant-type polymer compound or the pendant-type polymer crosslinked product according to <32> and an organic solvent.

<44> The polycyclic aromatic compound according to any one of <1> to <29> or a polymer thereof, which is arranged between the pair of electrodes composed of an anode and a cathode and the pair of electrodes, according to <30>. Organic layer having the reactive compound of, the polymer compound or polymer crosslinked body according to <31>, or the organic layer containing the pendant type polymer compound or pendant type polymer crosslinked body according to <32>. Electromagnetic light emitting element.
<45> The polycyclic aromatic compound according to any one of <1> to <29> or a polymer thereof, which is arranged between the pair of electrodes composed of an anode and a cathode and the pair of electrodes, according to <30>. The organic having a reactive compound of, the polymer compound or polymer crosslinked body according to <31>, or a light emitting layer containing the pendant type polymer compound or pendant type polymer crosslinked body according to <32>. Electrode emitting element.
<46> The light emitting layer is a host and the polycyclic aromatic compound as a dopant, a multimer thereof, a reactive compound, a polymer compound, a polymer crosslinked product, a pendant type polymer compound or a pendant type polymer crosslinked product. The organic field light emitting element according to <45>, which comprises.
<47> The organic electroluminescent device according to <46>, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound.

<48> It has an electron transporting layer and / or an electron injecting layer arranged between the cathode and the light emitting layer, and at least one of the electron transporting layer and the electron injecting layer is a borane derivative, a pyridine derivative, or fluorantene. Derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives and azoline The organic electric field light emitting element according to any one of <45> to <47>, which contains at least one selected from the group consisting of derivatives.
<49> The electron transporting layer and / or electron injecting layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, and an alkaline soil. Contains at least one selected from the group consisting of metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes. , <48>.
<50> A polymer obtained by polymerizing at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer as a monomer of a low molecular weight compound capable of forming each layer. A compound, a polymer crosslinked product obtained by further cross-linking the polymer compound, or a pendant type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain type polymer, or the pendant type height. The organic electroluminescent element according to any one of <44> to <49>, which comprises a pendant type polymer crosslinked body in which a molecular compound is further crosslinked.
<51> A display device or a lighting device including the organic electroluminescent element according to any one of <44> to <50>.

<52> A reaction step of metallizing the halogen atom (Hal) between X ¹ and X ² in the following intermediate-1 using an organic alkaline compound, and
Halides Y ^1, amination halides Y ^1, a reaction step of exchanging said metal and Y ¹ using a reagent selected from the group consisting of aryloxy compound of alkoxides and Y ¹ of Y ^1,
And a reaction step of coupling the B ring and C ring by the Y ¹ by successive electrophilic aromatic substitution using a Bronsted base, multi formula (1) according to <1> A method for producing a multimer of a ring aromatic compound or a polycyclic aromatic compound having a plurality of structures represented by the formula (1).

<53> The production method according to <52>, wherein the reaction is promoted by further adding a Lewis acid.
<54> A plurality of polycyclic aromatic compounds represented by the formula (1) or a structure represented by the formula (1) according to the following <1>, which comprises a reaction step of allowing an acid to act on the intermediate-2. A method for producing a multimer of a polycyclic aromatic compound having.

(In Intermediate-2, Z is —B (OH) ₂ which may be esterified.)

The present invention provides a novel polycyclic aromatic compound. The polycyclic aromatic compound of the present invention is useful as a material for organic devices, particularly as a material for a light emitting layer for forming a light emitting layer of an organic electroluminescent element. By using the compound of the present invention in the light emitting layer, it is possible to provide an organic EL device having high efficiency and long life.

It is the schematic sectional drawing which shows the example of the organic EL element. It is a figure explaining the method of manufacturing the organic EL element by the inkjet method on the substrate which has a bank.

The present invention will be described in detail below. The description of the constituent elements described below may be based on typical embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, the numerical range represented by using "-" means a range including the numerical values before and after "-" as the lower limit value and the upper limit value. Further, in the present specification, "hydrogen" in the description of the structural formula means "hydrogen atom (H)".

In the present specification, the chemical structure and the substituent may be represented by the number of carbon atoms, but the number of carbon atoms in the case where the substituent is substituted in the chemical structure or the substituent is further substituted in the substituent is the chemical structure or the substitution. It means the carbon number of each group, and does not mean the total carbon number of the chemical structure and the substituent or the total carbon number of the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent A of carbon number X" is substituted with "substituent B of carbon number Y". However, the number of carbon atoms Y is not the total number of carbon atoms of the substituent A and the substituent B. Further, for example, "substituent B having a carbon number Y substituted with a substituent A" means that "substituent A having no limitation on the number of carbon atoms" is substituted with "substituent B having a carbon number Y". However, the number of carbon atoms Y is not the total number of carbon atoms of the substituent A and the substituent B.

1. 1. Polycyclic aromatic compounds and multimers thereof The compounds of the present invention are polycyclic aromatic compounds represented by the following formula (1) or polycyclic aromatic compounds having a plurality of structures represented by the following formula (1). It is a multimer.

In the formula (1), "A" to "C" are symbols indicating a ring structure.

The A ring, B ring, and C ring in the formula (1) are independently aryl rings or heteroaryl rings, respectively, but at least one selected from the group consisting of A ring, B ring, and C ring. The ring is a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring. At least one hydrogen in these rings may be substituted with a substituent. The substituents are substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino (with aryl). Amino with heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, Substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl is preferable. When these groups have a substituent, examples of the substituent include aryl, heteroaryl, alkyl or cycloalkyl, and diarylamino.

It is preferable that at least one of the A ring, the B ring and the C ring is a ring having at least one substituent, and each of the A ring, the B ring and the C ring is a ring having at least one substituent. More preferably, it is a ring in which each of the A ring, the B ring and the C ring has one substituent.
As the substituent, a substituted or unsubstituted alkyl (particularly neopentyl), a cycloalkyl such as adamantyl is preferable, and a tertiary-alkyl (tR) is preferable. This is because such a bulky substituent increases the intermolecular distance and thus improves the emission quantum yield (PLQY). Further, as the substituent, diarylamino is also preferable.

The tertiary alkyl is represented by the following formula (tR).

In formula (tR), ^Ra , R ^b , and R ^c are independently alkyl having 1 to 24 carbon atoms, and any -CH _{2- in the} alkyl may be substituted with -O-. , The group represented by the formula (tR) is replaced with at least one hydrogen in the compound or structure represented by the formula (1) in *.

The "alkyl having 1 to 24 carbon atoms" of R ^a , R ^b and R ^c may be either a straight chain or a branched chain, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. Chain alkyl, alkyl with 1 to 18 carbon atoms (branched chain alkyl with 3 to 18 carbon atoms), alkyl with 1 to 12 carbon atoms (branched chain alkyl with 3 to 12 carbon atoms), alkyl with 1 to 6 carbon atoms (carbon) Examples thereof include branched chain alkyls having 3 to 6 carbon atoms and alkyl having 1 to 4 carbon atoms (branched chain alkyls having 3 to 4 carbon atoms).

The total number of carbon atoms of ^Ra , R ^b , and R ^c in the formula (tR) of the formula (1) is preferably 3 to 20 carbon atoms, and particularly preferably 3 to 10 carbon atoms.

Specific alkyls of R ^a , R ^b , and R ^c include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t. -Pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1- Methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, Examples thereof include 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicosyl.

Examples of the group represented by the formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-. Methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1- Dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1- Methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl- Examples thereof include 1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl and 1,1-dimethylhexyl. Of these, t-butyl and t-amyl are preferred.

Other preferred examples of substituents on the A, B, and C rings include, for example, diarylamino substituted with a group of formula (tR), carbazolyl substituted with a group of formula (tR) (preferably. Examples thereof include benzocarbazolyl (preferably N-benzocarbazolyl) substituted with a group of formula (tR) or N-carbazolyl. Examples of the "diarylamino" include groups described below as the "first substituent". As a form of substitution of a group of formula (tR) with diarylamino, carbazolyl and benzocarbazolyl, a part or all of hydrogen of the aryl ring or benzene ring in these groups was substituted with the group of formula (tR). For example.
The above description of the preferred substituents also applies to the polycyclic aromatic compounds represented by the formulas (2) to (9) and (12) to (19) and their multimers.

The aryl ring, heteroaryl ring, or condensed ring in the A ring, B ring, and C ring is a five-membered structure that shares a bond with the condensed bicyclic structure in the center of formula (1) composed of Y ¹ , X ^1, and X ^2. It may have a ring or a 6-membered ring.
Here, the "condensed bicyclic structure" means a structure in which two saturated hydrocarbon rings including Y ¹ , X ¹ and X ² shown in the center of the formula (1) are condensed. Further, the “6-membered ring that shares a bond with the condensed 2-ring structure” means a 6-membered ring (for example, a benzene ring) condensed into the condensed 2-ring structure. Further, "the aryl ring (which is the A ring) or the heteroaryl ring has the 6-membered ring" means that the A-ring is formed only by the 6-membered ring or includes the 6-membered ring. This means that another ring or the like is condensed with this 6-membered ring to form an A ring. In other words, the "aryl ring or heteroaryl ring having a 6-membered ring (which is an A ring)" as used herein means that a 6-membered ring constituting all or a part of the A ring is condensed into the condensed two-ring structure. It means that you are doing it. The same explanation applies to "B ring", "C ring", and "5-membered ring".

At least one ring selected from the group consisting of A ring, B ring and C ring in the formula (1) is two selected from the group consisting of a monocyclic aryl ring, a cyclopentadiene ring and a monocyclic heteroaryl ring. A condensed ring composed of the above rings (hereinafter, may be referred to as "condensed ring F". ". At least one hydrogen in this condensed ring may be substituted. The present inventors may perform such a condensation. It has been found that the light emission efficiency and the device life can be improved by constructing an organic EL element using a polycyclic aromatic compound having a ring as a material for a light emitting layer.

In formula (1), one or two rings selected from the group consisting of A ring, B ring and C ring are preferably fused ring F, and 1 selected from the group consisting of B ring and C ring. More preferably, one or two rings are fused rings F.

The number of rings constituting the fused ring F is not particularly limited, but is preferably 2 to 5, and more preferably 2 or 3. Examples of the constitution of the fused ring F include a fused ring of one aryl ring which is a monocyclic ring and one heteroaryl ring which is a monocyclic ring, a fused ring of one aryl ring which is a monocyclic ring and one cyclopentadiene ring, and a monocyclic ring. Examples thereof include a fused ring of two aryl rings and one heteroaryl ring which is a monocycle, and a fused ring of two aryl rings which are monocyclic and one cyclopentadiene ring. The aryl ring, which is a monocyclic ring at this time, is preferably a benzene ring. Examples of the monocyclic heteroaryl ring include a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyrimidine ring, and a pyridazine ring.

The fused ring F is preferably a combination of a 6-membered ring and a 5-membered ring. At this time, the 6-membered ring may share a bond with the condensed 2-ring structure described above, or the 5-membered ring may share a bond with the condensed 2-ring structure described above. The fused ring F is not composed only of the cyclopentadiene ring. The cyclopentadiene ring is preferably a 1,1-dimethyl-2,4-cyclopentadiene ring.
In the formula (1), among the A ring, the B ring, and the C ring, the ring other than the fused ring F is preferably a monocyclic aryl ring or a monocyclic heteroaryl ring, preferably a benzene ring. It is more preferably a pyridine ring or a pyrimidine ring, and even more preferably a benzene ring.

As one aspect, it is preferable that the fused ring F is composed of a heteroaryl ring containing a sulfur atom or an oxygen atom.
The fused ring F is a ring represented by the formula (BHet), a ring represented by the formula (DBHet), a ring represented by the formula (PBHet), or a ring represented by the formula (PPHet). Is preferable, and a ring represented by the formula (BHet) or a ring represented by the formula (DBHet) is more preferable. That is, the polycyclic aromatic compound represented by the formula (1) and its multimer are a ring represented by the formula (BHet), a ring represented by the formula (DBHet), and a ring represented by the formula (PBHet). , And at least one fused ring selected from the group consisting of rings represented by the formula (PPHet), preferably the ring represented by the formula (BHet) and the ring represented by the formula (DBHet). More preferably, it contains at least one fused ring selected from the group consisting of. The polycyclic aromatic compound represented by the formula (1) and its multimer are represented by a ring represented by the formula (BHet), a ring represented by the formula (DBHet), and a ring represented by the formula (PBHet) as the condensed ring F. It may contain any one kind of fused ring selected from the group consisting of the ring to be formed and the ring represented by the formula (PPHet), or may contain any two or more kinds of fused rings.

In the formula (BHet), R ^a1 to R ^a6 are hydrogens or substituents, except that any two or three of R ^a1 to R ^a6 adjacent to each other are Y ¹ and X ¹ in the formula (1). And / or a bond with X ² , where X is>O,>S,>Se,>NR,> Si (-R) _2, or> C (-R) ₂ . The R of>N-R,> Si (-R) ₂ , or> C (-R) ₂ as X is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, substituted. It may be an alkyl which may be substituted or a cycloalkyl which may be substituted, and the two Rs may be bonded to each other to form a ring.

R ^a1 to R ^a6 are hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroaryl. Amino, substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted. It is preferably alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. It is preferable that 0 to 2 of R ^a1 to R ^a6 are substituents (other than hydrogen) and the others (excluding those which are the above-mentioned binding agents) are hydrogen, and 0 to 0 of R ^a1 to R ^a6. It is more preferable that one is a substituent and the other is hydrogen. As the substituent at this time, a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.) represented by the above formula (tR), neopentyl, or adamantyl is preferable.

In the formula (BHet), X is preferably>O,>S,> NR, or> C (-R) ₂ , more preferably>O,> S, or> NR. ,> S is even more preferred. > R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. > R in C (—R) ₂ is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. ..

The two adjacent R ^a1 to R ^a6 that form a bond between Y ¹ and X ¹ and / or X ² include R ^a5 and R ^a6 , R ^a2 and R ^a3 , R ^a1 and R ^a2 , and R ^a3 and ^{Ra4 and the} like can be mentioned. When one or two rings selected from the group consisting of rings B and C are rings represented by the formula (BHet), R ^a5 and R ^a6 , R ^a2 and R ^a3 , R ^a1 and R ^a2 , ^{Alternatively} , it is preferable that R ^a3 and R ^a4 serve as a ^bonder, and it is more preferable that R ^a5 and R ^a6 serve as a ^bonder .
When ring A in the formula (1) is a ring represented by the formula (BHET), formula (BHET) binds to ^Y 1, ^{X 1,} and ^{^{^{X 2, R a1, R a2}}} , and ^{R a3} or, R ^a2 , R ^a3 , and R ^a4 serve as a bond.

In the formula (DBHet), R ^a11 to R ^a18 are hydrogens or substituents, except that any two or three of R ^a11 to R ^a18 adjacent to each other are Y ¹ and X in the formula (1). It becomes a bond with ¹ and / or X ^2, and X is>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C (-R) ₂ , and the above> N. The R of -R,> Si (-R) ₂ , or> C (-R) ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted. It is a good alkyl, or a optionally substituted cycloalkyl, and the two Rs may be bonded to form a ring. )
R ^a11 to R ^a18 are hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroaryl. Amino, substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted. It is preferably alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. It is preferable that 0 to 2 of R ^a11 to R ^a18 are substituents (other than hydrogen) and the others (excluding those that are the above-mentioned binding ^agents ) are hydrogen, and 0 to 0 to R ^a18 of R ^a11 to R ^a18. It is more preferable that one is a substituent and the other is hydrogen. As the substituent at this time, a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.) represented by the above formula (tR), neopentyl, or adamantyl is preferable.

In the formula (DBHet), X is preferably>O,>S,> N-R, or> C (-R) ₂ , and is>O,> S, or> C (-R) _2. Is more preferable, and> S or> O is even more preferable. > R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. > R in C (—R) ₂ is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. ..

The two adjacent R ^a11 to R ^a18 that form a bond between Y ¹ and X ¹ and / or X ² include R ^a11 and R ^a12 , R ^a12 and R ^a13 , R ^a13 and R ¹⁴ , R ^a15 and R. ^16, ^{R a16} and ^{R 17,} and ^{R a17} and ^{R 18} can be mentioned. When one or two rings selected from the group consisting of rings B and C are rings represented by the formula (DBHet), R ^a11 and R ^a12 , R ^a12 and R ^a13 , R ^a13 and R ¹⁴ , It is preferable that R ^a15 and R ¹⁶ , R ^a16 and R ¹⁷ , or R ^a17 and R ¹⁸ are the binding hands.
When the A ring in the formula (1) is a ring represented by the formula (BHet), the formula (DBHet) is combined with Y ¹ , X ¹ , and X ² , and R ^a11 , R ^a12 , and R ^a13 , R. ^a12, ^{R 13,} and ^{^{^{R 14, R a15, R 16}}} , and ^{R a16} or ^{^R 16,} ^R ^a17,, and ^{R 18} is a bond.

In formula (PBHet), Z is independently ^{C-R z} or N, at least one Z is ^N, R ^{z, R a26} and ^{R a25} is hydrogen or a substituent, provided that, ^{R z} , R ^a26 and R ^a25 , any two or three adjacent to each other will be a bond with Y ¹ and X ¹ and / or X ² in the formula (1), but R ^a26 and R are preferable. ^a25 serves as a ^bonder , and X is>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C (-R) ₂ , and the above-mentioned>N-R,> Si ( -R) ₂ or> C (-R) ₂ R is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or substituted. It is a cycloalkyl that may be present.

It is preferable that one or two of the four Zs in the formula (PBHet) are N, and it is more preferable that one is N. When the two are N, it is preferable that the two N are not adjacent to each other.

R ^z , R ^a26 and R ^a25 are hydrogen, or substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted ^{diheteroarylamino} , substituted or unsubstituted. Aryl Heteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or It is preferably unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl.
It is preferable that 0 to 2 of R ^z , R ^a26 and R ^a25 are substituents (other than hydrogen) and the others (excluding those which are the above-mentioned bonds) are hydrogen, and R ^z , R ^a26 and It is more preferable that 0 to 1 of R ^a25 is a substituent and the other is hydrogen. As the substituent at this time, a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.) represented by the above formula (tR), neopentyl, or adamantyl is preferable.

In the formula (PBHet), X is preferably>O,>S,> N-R, or> C (-R) ₂ , more preferably>O,> S, or> N-R. ,> S, or> O. > R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. > R in C (—R) ₂ is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. ..

In formula (PPHet), Z is independently C-R ^z or N, at least one Z is N, R ^z is hydrogen or a substituent, but any of the adjacent R ^z . Two or three of are the binders for Y ¹ and X ¹ and / or X ² in the formula (1), where X is>O,>S,>Se,>NR,> Si ( -R) ₂ or> C (-R) ₂ , and the R of>N-R,> Si (-R) ₂ , or> C (-R) ₂ is independently hydrogen-substituted. Aryl may be substituted, heteroaryl which may be substituted, alkyl which may be substituted, or cycloalkyl which may be substituted.

It is preferable that one or two of Z in the formula (PBHet) is N, and it is more preferable that one is N. When the two are N, it is preferable that the two N are not adjacent to each other.
R ^z is hydrogen, or substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino, substituted. Alternatively, unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted. Alternatively, it is preferably an unsubstituted aryloxy or a substituted silyl. It is preferable that 0 to 2 of R ^z are substituents (other than hydrogen) and the others (excluding those that form the above-mentioned bond) are hydrogen, and 0 to 0 of R ^z , R ^a26 and R ^a25. It is more preferable that one is a substituent and the other is hydrogen. As the substituent at this time, a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.) represented by the above formula (tR), neopentyl, or adamantyl is preferable.

In the formula (PPHet), X is preferably>O,>S,> N-R, or> C (-R) ₂ , more preferably>O,> S, or> N-R. ,> S, or> O. > R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. > R in C (—R) ₂ is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. ..

Y ¹ in the formula (1) is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is aryl. , Alkyl, or cycloalkyl. In the case of P = O, P = S, Si-R, or Ge-R, the atom bonded to the A ring, B ring, or C ring is P, Si, or Ge. As Y ¹ , B, P, P = O, P = S, or Si—R is preferable, and B is particularly preferable.

X ¹ and X ² in the formula (1) are independently>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se, respectively. It is preferable that at least one of X ¹ and X ² in the formula (1) is> NR, both of which are> NR, or ^one of X ¹ and X ² is> NR. It is more preferable that the other is> C (−R) ₂ .
The> N-R R in X ¹ and X ² is hydrogen, optionally substituted aryl (except amino as a substituent), optionally substituted heteroaryl, optionally substituted alkyl or It is a cycloalkyl which may be substituted, and the R of> Si (-R) ₂ is independently hydrogen, an aryl which may be substituted, a heteroaryl which may be substituted, and a substituent. It is an alkyl which may be substituted or a cycloalkyl which may be substituted, and the R of> C (-R) ₂ is independently hydrogen, an aryl which may be substituted, and a hetero which may be substituted. Aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, the two Rs are preferably identical, and the two Rs may be bonded to form a ring.

The R of> N-R in X ¹ and X ² is preferably an aryl that may be substituted or a heteroaryl that may be substituted. Here, the aryl is preferably phenyl, biphenylyl (particularly 2-biphenylyl), and terphenylyl (particularly terphenyl-2'-yl), and the heteroaryl is benzothienyl (2-benzothienyl, 6-benzo). Thienyl, etc.), benzofuranyl (2-benzofuranyl, 3-benzofuranyl, 5-benzofuranyl, etc.), dibenzofuranyl (4-dibenzofuranyl, etc.), dimethylxanthenyl (2-dimethylxanthenyl, etc.), dibenzodioxynyl, etc. preferable. As the substituent, tertiary-alkyl (particularly t-butyl) represented by the above formula (tR) or cycloalkyl (particularly adamantyl) is preferable. The number of substituents in aryl and heteroaryl is preferably 0 to 2, more preferably 1 or 2, and even more preferably 1. It is also preferable that the aryl ring in the above aryl is condensed with cycloalkane as described later.

Particularly preferred examples of> N-R Rs in X ¹ and X ² are condensed with optionally substituted 2-biphenylyl, optionally substituted terphenyl-2'-yl, and cycloalkane. Aryl (which may be substituted) is mentioned. As the 2-biphenylyl which may be substituted, 2-biphenylyl substituted with 1 to 3 t-butyl is particularly preferable. As the optionally substituted terphenyl-2'-yl, unsubstituted [1,1': 3', 1'''-terphenyl] -2'-yl is particularly preferable. The aryl condensed with cycloalkane is particularly preferably as follows.

(Me indicates methyl, tBu indicates t-butyl, * indicates the binding position.)

By using the compound of the present invention having R> N-R in the above preferable range as X ¹ or X ² as a light emitting material, the luminous efficiency and the device life can be further improved.

When both X ¹ and ^{X 2} are> N-R, ^{X 1} and only either one of R of> N-R in ^{X 2} may be substituted 2- biphenylyl or ^{X 1} and X, It is more preferable that the terphenyl-2'-yl is obtained by substituting only one R of> N-R in ² or the R of> N-R on both sides. As the terphenyl-2'-yl, [1,1': 3', 1'''-terphenyl] -2'-yl is preferable. X ¹ and only either one of R of> N-R in X ² is, on the other when they are may also be 2-biphenylyl or substituted optionally which may be substituted terphenyl-2'-yl> N -R of R is preferably phenyl which may be substituted. Examples of such a compound include the following compounds (1F-25), compounds (1F-90), and compounds such as compound (1F-90').

When both X ¹ and X ² are> N-R, one of R a> N-R in X ¹ and X ^2, (optionally substituted) aryl fused with cycloalkane Is also preferable. At this time, the other R of> N-R is preferably phenyl which may be substituted.
Also, ^one R of> N-R in X1 and X2 is ² -biphenylyl which may be substituted, and the other> N-R R is an aryl condensed with a cycloalkane (). It may be substituted).

> N-R in X ¹ and ^{_{X 2,> Si (-R)}} 2 and> C _(-R) is at least one on in R ₂ wherein ring A by a linking group or a single bond, B ring, and the ring C It may be bonded to at least one ring. As the linking group, -O-, -S-, or -C (-R) ₂ -is preferable. The R of the above-mentioned "-C (-R) _2- " is hydrogen, alkyl or cycloalkyl. This specification can be expressed by a compound having a ring structure in which X ¹ and X ² are incorporated into the condensed ring B'and the condensed ring C', which are represented by the following formula (2-3-1). That is, for example, a B'ring formed by condensing other rings by incorporating X ¹ (or X ² ) into a benzene ring which is a b ring (or c ring) in the formula (2) described later. Or a compound having a C'ring). The formed fused ring B'(or fused ring C') is, for example, a carbazole ring, a phenothiazine ring, a phenothiazine ring, or an acridine ring.

Further, the above specification is a compound having a ring structure in which X ¹ and / or X ² is incorporated into the condensed ring A', which is represented by the following formula (2-3-2) or formula (2-3-3). But it can be expressed. That is, for example, it is a compound having an A'ring formed by condensing other rings so as to incorporate X ¹ (and / or X ² ) into the benzene ring which is the a ring in the formula (2). The formed fused ring A'is, for example, a carbazole ring, a phenothiazine ring, a phenothiazine ring, or an acridine ring.

In the formula (1), the B ring and the C ring may be bonded via a single bond or a linking group. Examples of the linking group include>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R and> Si. The Rs of (-R) ₂ are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, respectively. The R of> C (-R) ₂ is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cyclo. It is alkyl. Further, R in at least one of>N-R,> Si (-R) ₂ and> C (-R) ₂ is bonded to at least one ring of the B ring and C ring by a linking group or a single bond. As the linking group, -O-, -S-, or -C (-R) ₂ -is preferable. The R of the above-mentioned "-C (-R) _2- " is hydrogen, alkyl, or cycloalkyl. R in at least one of>N-R,> Si (-R) ₂ and> C (-R) ₂ is bonded to at least one ring of the B ring and C ring by a linking group or a single bond. For details of the morphology, refer to the above-mentioned explanations using the formulas (2-3-1), (2-3-2), and (2-3-3) for X ¹ and X ^2. Can be done.

When the B ring and the C ring are bonded via a linking group, it is preferable that the above linking group directly bonds the aryl ring and the heteroaryl ring in the B ring and the C ring. It is also preferable that the substituents of the aryl ring and the heteroaryl ring in the B ring and the C ring are bonded via a single bond.

Specific>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S, as a linking group that binds X ¹ , X ² , and B and C rings. Or>Se,>O,>N-R,> C (-R) ₂ , or> S is preferred,>O,> N-R, or> C (-R) ₂ is more preferred,> O or> N-R is particularly preferred.

Examples of the "aryl ring" which is the A ring, the B ring, and the C ring of the formula (1) include an aryl ring having 6 to 30 carbon atoms, and an aryl ring having 6 to 16 carbon atoms is preferable. An aryl ring of 6 to 12 is more preferable, and an aryl ring having 6 to 10 carbon atoms is particularly preferable.

Specific "aryl rings" include a benzene ring which is a monocyclic system, a biphenyl ring which is a bicyclic system, a naphthalene ring which is a fused bicyclic system, an inden ring, and a terphenyl ring (m-tel) which is a tricyclic system. (Phenyl, o-terphenyl, p-terphenyl), fused tricyclics, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, anthracene ring, fused tetracyclic triphenylene ring, pyrene ring, naphthalene ring, Examples thereof include a chrysen ring, a perylene ring which is a fused pentacyclic system, and a pentacene ring. In addition, the fluorene ring, the benzofluorene ring, and the indene ring also include a structure in which a fluorene ring, a benzofluorene ring, a cyclopentane ring, and the like are spiro-bonded, respectively. In the fluorene ring, benzofluorene ring, and indene ring, two of the two hydrogens of methylene are substituted with alkyl such as methyl as the first substituent described later, respectively, and the dimethylfluorene ring and the dimethylbenzofluorene ring are respectively. And those having a dimethylindene ring are also included.

Examples of the "heteroaryl ring" which is the A ring, the B ring, and the C ring of the formula (1) include a heteroaryl ring having 2 to 30 carbon atoms, and a heteroaryl ring having 2 to 25 carbon atoms is preferable. , A heteroaryl ring having 2 to 20 carbon atoms is more preferable, a heteroaryl ring having 2 to 15 carbon atoms is further preferable, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferable. Further, examples of the "heteroaryl ring" include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms. In addition, this "heteroaryl ring" is a hetero formed by bonding adjacent groups of "R ¹ to R ¹¹ " defined by the formula (2) described later together with an a ring, a b ring or a c ring. Since the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, the total carbon number of the fused ring in which a 5-membered ring is condensed is 6 carbon atoms. It is the lower limit of carbon number.

Specific "heteroaryl rings" include, for example, a pyrrole ring, an oxazole ring, an isooxazole ring, a thiazole ring, an isothazole ring, an imidazole ring, an oxazole ring, a thiazazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, and the like. Ppyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring , Synnoline ring, quinazoline ring, quinoxalin ring, phthalazine ring, naphthylidine ring, purine ring, pteridine ring, carbazole ring, aclysin ring, phenoxatiein ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indolidin ring, Fran ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, flazan ring, thiantolen ring, indolocarbazole ring, benzoindrocarbazole ring, benzobenzoindrocarbazole ring, naphthobenzofuran ring, Examples thereof include a dioxine ring, a dihydroaclysin ring, a xanthene ring, a thioxanthene ring, and a dibenzodioxin ring. Further, in the dihydroacridine ring, the xanthene ring, and the thioxanthene ring, two of the two hydrogens of methylene are substituted with an alkyl such as methyl as the first substituent described later, respectively, and the dimethyldihydroacridine ring and the dimethyl are substituted. Those having a xanthene ring, a dimethylthioxanthene ring, or the like are also preferable. Further, a bipyridine ring, a phenylpyridine ring, a pyridylphenyl ring, a tricyclic terpyridyl ring, a bispyridylphenyl ring, and a pyridylbiphenyl ring are also mentioned as "heteroaryl rings". Further, the "heteroaryl ring" shall also include a pyran ring.

At least one hydrogen in the "aryl ring" or "heteroaryl ring" is the first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted. "Diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryls via a single bond or a linking group) (May be bonded) ", substituted or unsubstituted" alkyl ", substituted or unsubstituted" cycloalkyl ", substituted or unsubstituted" alkoxy ", substituted or unsubstituted" aryloxy ", or substituted Although it may be substituted with "silyl" in the above, "aryl" or "heteroaryl" as the first substituent, aryl of "diarylamino", heteroaryl of "diheteroarylamino", "arylhetero" Examples of the aryl and heteroaryl of "arylamino", the aryl of "diarylboryl", and the aryl of "aryloxy" include the monovalent group of the above-mentioned "aryl ring" or "heteroaryl ring".

Specifically, examples of the "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and aryls having 6 to 16 carbon atoms. Is more preferable, aryl having 6 to 12 carbon atoms is particularly preferable, and aryl having 6 to 10 carbon atoms is most preferable.

Specific examples of the aryl include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused dicyclic aryl. , (2-, 3-, 4-, 5-, 6-, 7-) indenyl, terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-4'-yl, which is a tricyclic aryl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m -Terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2 -Il, p-terphenyl-3-yl, p-terphenyl-4-yl), acetylene- (1-, 3-, 4-, 5-) yl, which is a fused tricyclic aryl, fluoren- ( 1-, 2-, 3-, 4-, 9-) yl, phenalene- (1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthryl, tetracyclic aryl Quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m -Quaterphenylyl), triphenylene- (1-, 2-) yl, which is a fused tetracyclic aryl, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) ) Ill, perylene- (1-, 2-, 3-) yl, which is a fused pentacyclic aryl, pentasen- (1-, 2-, 5-, 6-) yl and the like.

Examples of the "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, and 2 to 20 carbon atoms. Heteroaryl of 15 is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific heteroaryls include, for example, frills, thienyl, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, frazayl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, dibenzofuranyl, benzo [b] thienyl, dibenzothienyl, indrill, isoindrill, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, synnolyl, quinazolyl, Examples thereof include quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxadinyl, phenothiazine, phenazinyl, phenoxatinyl, thiantrenyl and indolidinyl.

Further, the "alkyl" as the first substituent may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms and a branched chain alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and an alkyl having 1 to 8 carbon atoms is more preferable. (Branched chain alkyl having 3 to 8 carbon atoms) is more preferable, and alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms) is particularly preferable, and alkyl having 1 to 5 carbon atoms (3 to 5 carbon atoms) is particularly preferable. Branched chain alkyl) is most preferred.

Specific alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-. Hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3) -Tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc. can give.
Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2- Trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3- Dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1 -Propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like can also be mentioned.

The "cycloalkyl" as the first substituent includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, and cycloalkyl having 3 to 14 carbon atoms. , Cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms, and the like.

Specific cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, alkyl (particularly methyl) substituents having 1 to 5 carbon atoms, norbornenyl, and bicyclo [1]. .0.1] Butyl, Bicyclo [1.1.1] Pentyl, Bicyclo [2.0.1] Pentyl, Bicyclo [1.2.1] Hexyl, Bicyclo [3.0.1] Hexyl, Bicyclo [2] .1.2] Heptyl, bicyclo [2.2.2] Octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.

Further, as the "alkoxy" as the first substituent, for example, an alkoxy having a straight chain having 1 to 24 carbon atoms or a branched chain having 3 to 24 carbon atoms can be mentioned. Alkoxy having 1 to 18 carbon atoms (alkoxy of branched chains having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbon atoms (alkoxy of branched chains having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms is more preferable. Alkoxy (alkoxy of branched chains having 3 to 6 carbon atoms) is more preferable, and alkoxy having 1 to 5 carbon atoms (alkoxy of branched chains having 3 to 5 carbon atoms) is particularly preferable.

Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

Further, as the "substituted silyl" as the first substituent, for example, silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl can be mentioned. For example, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

Examples of the "trialkylsilyl" include groups in which each of the three hydrogens in the silyl group is independently substituted with an alkyl, and this alkyl cites the group described as "alkyl" in the first substituent described above. be able to. Preferred alkyls for substitution are alkyls having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

Specific trialkylsilyls include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, trit-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethyl Cyril, t-butyldipropylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, Examples thereof include methyldii-propylsilyl, ethyldii-propylsilyl, butyldii-propylsilyl, sec-butyldii-propylsilyl, t-butyldii-propylsilyl, and t-amyldii-propylsilyl.

Examples of the "tricycloalkylsilyl" include groups in which the three hydrogens in the silyl group are independently substituted with cycloalkyl, and this cycloalkyl has been described as "cycloalkyl" in the first substituent described above. The group can be quoted. Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo [1.1.1] pentyl, bicyclo [. 2.0.1] Pentyl, bicyclo [1.2.1] hexyl, bicyclo [3.0.1] hexyl, bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, Examples include decahydronaphthalenyl and decahydroazurenyl.

Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

Specific examples of the dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and the alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls are selected from the specific alkyls and cycloalkyls described above. Examples thereof include silyl in which the group to be substituted is substituted.

Specific examples of the dialkylarylsilyl substituted with two alkyls and one aryl, the alkyldiarylsilyl substituted with one alkyl and two aryls, and the triarylsilyl substituted with three aryls include the specific alkyls described above. And silyls substituted with groups selected from aryl. Specific examples of triarylsilyl include triphenylsilyl.

Further, as the "aryl" in the "diarylboryl" of the first substituent, the above-mentioned description of aryl can be cited. Further, the two aryls may be bonded via a single bond or a linking group (for example,> C (-R) ₂ ,>O,> S or> NR). Here, R of> C (-R) ₂ and> N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy (above, the first substituent), and the first is said. The substituent may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (hereinafter, the second substituent), and specific examples of these groups include aryl and hetero as the first substituent described above. Descriptions of aryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy can be cited.

Substituents, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted Alternatively, an unsubstituted "aryl heteroarylamino", a substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", Substitutive or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted "silyl" are as described as substituted or unsubstituted. At least one hydrogen in the above may be substituted with a second substituent. Examples of the second substituent include aryl, heteroaryl, alkyl, and cycloalkyl, and specific examples thereof include the monovalent group of the above-mentioned "aryl ring" or "heteroaryl ring", and also. A description of "alkyl" or "cycloalkyl" as the first substituent can be referred to. Further, in aryl and heteroaryl as the second substituent, at least one hydrogen in them is aryl such as phenyl (specific example is the group described above), methyl, alkyl such as t-butyl (specific example is described above). Aryl or heteroaryl as a second substituent is also included in a structure substituted with a cycloalkyl (specific example is the group described above) such as (group) or cyclohexyl. As an example, when the second substituent is carbazolyl, carbazolyl in which at least one hydrogen at the 9-position is substituted with aryl such as phenyl, alkyl such as methyl or cycloalkyl such as cyclohexyl is also the second. Included in heteroaryl as a substituent.

The emission wavelength can be adjusted by the steric hindrance, electron donation and electron attraction of the structure of the first substituent. It is preferably a group represented by the following structural formula, and more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-. Xyryl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3,6- Dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xsilyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6 -Di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, a larger steric hindrance is preferable for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, and p-tolyl. , 2,4-xylyl, 2,5-xsilyl, 2,6-xsilyl, 2,4,6-mesityl, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, 3,6- Dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

In the following structural formula, "Me" is methyl, "tBu" is t-butyl, "tAm" is t-amyl, "tOct" is t-octyl, and * represents the binding position.

R a Si-R and Ge-R in Y ¹ in the formula (1) is aryl, is an alkyl or cycloalkyl, the aryl, group described above can be exemplified as alkyl or cycloalkyl. In particular, aryls having 6 to 10 carbon atoms (for example, phenyl, naphthyl, etc.), alkyls having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or cycloalkyls having 5 to 10 carbon atoms (preferably cyclohexyl, adamantyl, etc.) are preferable. This description will be described in the following equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6) -1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1) ), (15-1), (16-1), (17-1), (18-1), a ^{Y 1} same in (19-1) and (20-1).

R of> N-R in X ¹ and X ² in the formula (1), and, R in the> N-R as a connecting group bonding B ring and C ring is substituted with a second substituent described above may, aryl, heteroaryl, alkyl or cycloalkyl (where the aryl as R of> N-R in X ¹ and X ² amino no substitution). Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. Further, as the second substituent at this time, for example, alkyl such as methyl, tertiary butyl, amyl, p-terrary butyl phenyl and the like are preferable. The alkyl substitution position is preferably a para position with respect to the N substitution position. > R of NR includes an aryl having 6 to 10 carbon atoms (for example, phenyl, naphthyl, etc.) which may be substituted with a second substituent, and a carbon which may be substituted with a second substituent. Heteroaryls of number 2 to 15 (eg, carbazolyl), alkyls of 1 to 5 carbons (eg, methyl, ethyl, etc.) or cycloalkyls of 5 to 10 carbons (preferably cyclohexyl or adamantyl) are preferred. This description will be described in the following equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14). , (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), ( 6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14- X ¹ , X ² , X ³ , and X in 1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1). ^The same applies to ⁴ , and the same applies to the linking group formed by combining R ⁷ and R ^{8 in} the formula (2), R ⁸ and R ²⁴ in the formula (3), or R ³⁴ and R ²⁴ in the formula (5). Is.

The R of> N-R in X ¹ and X ² is particularly preferably the above-mentioned range as the R of> N-R in X ¹ and X ² of the formula (1), and the above-mentioned preferable range is the formulas (7) and (7). The same applies to X ³ and X ⁴ in (8), (9), (7-1), (8-1), and (9-1).

^{X 1} and> Si in ^{X 2} _{(-R) 2} of R of formula (1), as well as the> Si _{(-R) 2} of R as a connecting group bonding B ring and C ring, the above-described 2 Aryl, heteroaryl, alkyl or cycloalkyl, which may be substituted with the substituents of. Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above. In particular, aryls having 6 to 10 carbon atoms (for example, phenyl, naphthyl, etc.), heteroaryls having 2 to 15 carbon atoms (for example, carbazolyl), alkyls having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or 5 to 10 carbon atoms. Cycloalkyl (preferably cyclohexyl or adamantyl) is preferred. This description will be described in the following equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14). , (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), ( 6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14- X ¹ , X ² , X ³ , and X in 1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1). ^The same applies to ⁴ , and the same applies to the linking group formed by combining R ⁷ and R ^{8 in} the formula (2), R ⁸ and R ²⁴ in the formula (3), or R ³⁴ and R ²⁴ in the formula (5). Is.

^{X 1} and> in ^{X 2} C _{(-R) 2} of R, and, as a connecting group bonding ring B and ring C> C _{(-R) 2} of R of formula (1) is hydrogen, the above-described Aryl, heteroaryl, alkyl or cycloalkyl, which may be substituted with a second substituent. Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above. In particular, aryls having 6 to 10 carbon atoms (for example, phenyl, naphthyl, etc.), heteroaryls having 2 to 15 carbon atoms (for example, carbazolyl), alkyls having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or 5 to 10 carbon atoms. Cycloalkyl (preferably cyclohexyl or adamantyl) is preferred. This description will be described in the following equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14). , (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), ( 6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14- X ¹ , X ² , X ³ , and X in 1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1). ^The same applies to the linking group formed by combining R ⁷ and R ^{8 in} the formula (2), R ⁸ and R ²⁴ in the formula (3), or R ³⁴ and R ²⁴ in the formula (5).

Examples of the linking group in the formula (1) when the linking group that binds the X ¹ , X ² , or the B ring and the C ring is bonded to at least one ring of the A ring, the B ring, and the C ring are used. -O-, -S-, -C (-R) ₂ -or single bond, etc. can be mentioned, and the R of "-C (-R) _2- " in these is hydrogen, alkyl, or cycloalkyl. However, examples of this alkyl or cycloalkyl include the groups described above. In particular, an alkyl having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferable. This description will be described in the following equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6) -1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1) ), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1), which are the linking groups "-C (-R) _2". -”Is the same.

In addition, the present invention is a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the formula (1), preferably the formulas (2), (3), (4), (5), which will be described later. (6), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1) ), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20) It relates to a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by -1). The multimer is preferably a dimer, more preferably a dimer, and particularly preferably a dimer. The multimer may be in a form having a plurality of the above unit structures in one compound. For example, the multimer is a single bond, and a plurality of the unit structures are bonded by a linking group such as alkylene, phenylene, naphthylene and the like having 1 to 3 carbon atoms. In addition to the form (connected multimer), any ring (A ring, B ring or C ring, or a ring, b ring or c ring, etc.) included in the unit structure is shared by a plurality of unit structures. It may be in the form of a bond (ring-shared multimer), or any ring (A ring, B ring or C ring, or a ring, b ring or c ring) included in the unit structure. Although they may be in the form of being bonded in such a way that they are condensed (ring-condensed multimer), a ring-covalent multimer and a ring-condensed multimer are preferable, and a ring-covalent multimer is more preferable.
As an example of the structure of the multimer, the structure represented by the formula (9) described later can be given.

Further, the hydrogen in the chemical structure of the polycyclic aromatic compound represented by the formula (1) and its multimer may be deuterium, cyano, or halogen in whole or in part. For example, in the formula (1), A ring, B ring, C ring (A ~ C ring aryl or heteroaryl ring), substituent to A ~ C ring, ^{Y 1} is Si-R or Ge-R R (= alkyl, cycloalkyl, aryl) when, and R when X ¹ and X ² are>N-R,> C (-R) ₂ , or> Si (-R) _2. = Alkyl, cycloalkyl, aryl) hydrogen can be replaced with deuterium, cyano or halogen, of which all or part of the hydrogen in aryl or heteroaryl is replaced with deuterium, cyano, or halogen. Can be given. The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and even more preferably fluorine. From the viewpoint of durability, it is also preferable that all or part of the hydrogen in the chemical structure of the polycyclic aromatic compound represented by the formula (1) and its multimer is deuterium.

As preferable examples of the polycyclic aromatic compound represented by the formula (1) and its multimer, the following formulas (2), (3), (4), (5), (6), (7), (8) ) Or (9), polycyclic aromatic compounds and their multimers, and the following formulas (12), (13), (14), (15), (16), (17), (18) ( 19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), ( 9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-) Examples thereof include polycyclic aromatic compounds represented by 1), (18-1), (19-1) and (20-1) and their multimers. The equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15) , (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1) , (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), ( Regarding the structure of the substituents and the contained rings in (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1), the corresponding formulas ( Each explanation of 1) can be referred to.

In equations (2), (3), (4), (5), (6), (7), (8), and (9), R ¹ to R ¹⁷ , R ²¹ to R ²⁴ , R ³¹ to R ³⁴ and R ⁴¹ to R ⁴⁴ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls via a single bond or a linking group). , Alkoxy, cycloalkyl, alkoxy, aryloxy, or substituted silyls, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Further, the adjacent groups of R ¹ to R ³ are bonded to each other to form the a ring, and the adjacent groups of R ⁸ to R ¹¹ are bonded to each other to form the b ring of R ⁴ to R ⁷ . Adjacent groups are bonded to each other to form a ring c, adjacent groups of R ¹² to R ¹⁴ are bonded to each other to form a12 ring, and adjacent groups of R ¹⁵ to R ¹⁷ are bonded to each other to form a ring b15. With, adjacent groups of R ²¹ to R ²⁴ are bonded to each other with the c21 ring, adjacent groups of R ³¹ to R ³⁴ are bonded to each other with the b31 ring, and of R ⁴¹ to R ⁴⁴ . Adjacent groups of the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b41 ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, or dihetero. Arylamino, aryl heteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, It may be substituted with dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

In the formula (2), at least one set of two adjacent groups of R ¹ to R ¹¹ are combined to form a divalent group represented by the formula (Het). However, if the ^{R 4} and ^{R 5} and ^{R 6} and ^{R 7} constitute a divalent group represented by the formula (Het) simultaneously, as well as the ^{R 8} and ^{R 9} and ^{R 10} and ^{R 11} simultaneously It is excluded when it constitutes a divalent group represented by the formula (Het). That is, neither the b ring nor the c ring is formed by combining two divalent groups represented by two or more formulas (Het) to form a three-ring condensed ring.
In formula (7), at least one set of two adjacent groups of R ¹ to R ³ and R ⁹ to R ¹⁷ are combined to form a divalent group represented by the formula (Het). There is.

In equations (2), (3), (4), (5), (6), (7), (8), and (9), R ¹ to R ¹⁷ , R ²¹ to R ²⁴ , R ³¹ to R ³⁴ and R ⁴¹ to R ⁴⁴ are independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, and diallylamino (where aryl is aryl having 6 to 12 carbon atoms), respectively. Diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, and an alkyl having 3 to 24 carbon atoms. Cycloalkyl or trialkylsilyl (where alkyl is an alkyl having 1 to 6 carbon atoms) is preferred. Further, adjacent groups of R ¹ to R ³ are bonded to each other to form a ring, and adjacent groups of R ⁸ to R ¹¹ are bonded to each other to form a ring b, of which R ⁴ to R ⁷ are formed. Adjacent groups are bonded to each other to form a c ring, adjacent groups of R ¹² to R ¹⁴ are bonded to each other to form an a12 ring, and adjacent groups of R ¹⁵ to R ¹⁷ are bonded to each other to form a b15 ring. At the same time, adjacent groups of R ²¹ to R ²⁴ are bonded to each other to form a c21 ring, and adjacent groups of R ³¹ to R ³⁴ are bonded to each other to form a b31 ring, and of R ⁴¹ to R ⁴⁴ . Adjacent groups may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, respectively, together with the b41 ring, and at least one hydrogen in the formed ring may be formed. , Aryl with 6 to 10 carbon atoms, alkyl with 1 to 12 carbon atoms, cycloalkyl with 3 to 16 carbon atoms or trialkylsilyl (where alkyl is alkyl with 1 to 4 carbon atoms) may be substituted.

R ² in the formulas (2), (3), (4), (5) and (6) is alkyl (methyl, t-butyl, etc.), substituted phenyl (2,6, dimethylphenyl, etc.), diarylamino ( It is preferably diphenylamino or the like) or carbazolyl (N-carbazolyl or the like). Further, it is preferable that R ¹ and R ³ , which are groups other than R ² in the a ring, are hydrogen, respectively.

Equation (2) (Equation (Het)), Equation (3), Equation (4), Equation (5), Equation (6), Equation (7) (Equation (Het)), Equation (8), and Equation ( 9) Among them, X is>O,>S,>Se,>NR,> Si (-R) ₂ , or> C (-R) ₂ . The R of>N-R,> Si (-R) ₂ , or> C (-R) ₂ as X is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl. , Aryl which may be substituted or cycloalkyl which may be substituted, an aryl having 6 to 30 carbon atoms which may be substituted, a heteroaryl which may be substituted and having 2 to 30 carbon atoms, substituted. It is preferably an alkyl having 1 to 24 carbon atoms which may be substituted, or a cycloalkyl having 3 to 24 carbon atoms which may be substituted. > R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. > R in C (—R) ₂ is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. .. Further, X is preferably>O,>S,> N-R, or> C (-R) ₂ , more preferably>O,>S,> N-R, and> S, or. > O is even more preferred.

In formula (Het), R ^b1 and R ^b2 are hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are attached via a single bond or a linking group). Can be), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, where * is. Represents the bond position (bonding hand as a substituent), where X is>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C (-R) ₂ , and the above> The R of NR,> Si (-R) ₂ , or> C (-R) ₂ is aryl, heteroaryl, alkyl or cycloalkyl. In formula (Het), R ^b1 and R ^b2 are hydrogen, aryls having 6 to 30 carbon atoms, heteroaryls having 2 to 30 carbon atoms, diallylamino (where aryls are aryls having 6 to 12 carbon atoms), and diallylboryls (provided that they are arylboryls). Aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or It is preferably a trialkylsilyl (where alkyl is an alkyl having 1 to 6 carbon atoms).

R ⁷ and R ⁸ in formula (2), R ⁸ and R ²⁴ in formula (3), or R ³⁴ and R ²⁴ in formula (5) are combined to form a single bond,>O,>NR,>. Even if Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se (preferably>O,>N-R,> C (-R) ₂ , or> S) Good. This is an example of the case where the B ring and the C ring are bonded in the formula (1). For example, in the form in which R ⁷ and R ⁸ are bound, a 6-membered ring is formed from Y ¹ , (a part of) c ring, the binding site of R ⁷ and R ⁸ and (a part of) b ring. Corresponds to the form Further, a 5-membered ring or a 6-membered ring surrounded by Y ¹ , one side of the benzene ring which is the c ring, the binding sites of R ⁷ and R ⁸ , and one side of the benzene ring which is the b ring was formed. It can be said to be a form. The> N-R and> Si (-R) ₂ R independently have an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a carbon number of carbon atoms. It is a cycloalkyl of 3 to 14, and the R of> C (-R) ₂ is hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or carbon. The number 3 to 14 is cycloalkyl, and the R in at least one of>N-R,> Si (-R) ₂ , and> C (-R) ₂ is -O-, -S-, It may be bonded to at least one ring of the b ring and the c ring by -C (-R) _2- or a single bond. The R of> N-R is preferably an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. The R of> C (—R) ₂ is preferably hydrogen, an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.

Y ¹ in equations (2), (3), (4), (5), (6), (7), (8) and (9) are independently B, P, P = O. , P = S, Al, Ga, As, Si-R, or Ge-R, and the R of Si-R and Ge-R is an aryl having 6 to 12 carbon atoms and an alkyl having 1 to 6 carbon atoms. Alternatively, it is a cycloalkyl having 3 to 14 carbon atoms. As Y ¹ , B, P, P = O, P = S, or Si—R is preferable, and B is particularly preferable.

Equation (2), (3), (4), (5), X 1, X 2 in (6), and, (7), (8) ^X 1 in and ^{(9), X} 2, X ³ and X ⁴ are independently>O,>NR,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se, and the above-mentioned> NR and> Se. > R of Si (-R) ₂ is independently hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, a heteroaryl having 2 to 15 carbon atoms which may be substituted, and substituted. It may be an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and R of> C (−R) ₂ is hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted. It is a heteroaryl having 2 to 15 carbon atoms which may be substituted, an alkyl having 1 to 6 carbon atoms which may be substituted, or a cycloalkyl having 3 to 14 carbon atoms which may be substituted. Further, R in at least one of>N-R,> Si (-R) ₂ and> C (-R) ₂ is -O-, -S-, -C (-R) _2- , or simply. By bonding, it binds to at least one ring selected from the group consisting of a 5-membered ring that condenses with an a-ring, a b-ring, a c-ring, an a12 ring, a b15 ring, a c21 ring, and a 5-membered ring that condenses with a b31 ring. You may be.

Here, R in at least one of "the above>N-R,> Si (-R) ₂ and> C (-R) ₂ in the formula (1) is the A ring, the B ring and the A ring, the B ring and The provision that "it is bonded to at least one ring of C ring" is defined in the formula (2), (3), (4), (5), (6), (7), (8) or (9). Then, "R in at least one of>N-R,> Si (-R) ₂ and> C (-R) ₂ is -O-, -S-, -C (-R) _2- or a single bond. At least one ring selected from the group consisting of a 5-membered ring that condenses with an a ring, a b ring, a c ring, an a12 ring, a b15 ring, a c21 ring, a 5-membered ring that condenses with a b31 ring, and a b41 ring. Corresponds to the provision of "combined with".

X ¹ , X ² , X ³ , and X ⁴ are independently>O,>NR,> C (-R) ₂ , or> S, and the R of> NR is It is preferably an aryl having 6 to 10 carbon atoms which may be substituted, an alkyl having 1 to 4 carbon atoms which may be substituted, or a cycloalkyl having 5 to 10 carbon atoms which may be substituted. The R of C (-R) ₂ is hydrogen, an aryl having 6 to 10 carbon atoms which may be substituted, an alkyl having 1 to 4 carbon atoms which may be substituted, or 5 carbon atoms which may be substituted. It is preferably about 10 cycloalkyl.

Selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), and (9). At least one (a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, and b41 ring, the formed ring, at least one of the aryl and the heteroaryl) is. It may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane has an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, and 1 carbon atom. It may be substituted with an alkyl of ~ 24 or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH _2- in the cycloalkane may be substituted with -O-.

Selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9). When at least one of the cycloalkanes is condensed with at least one cycloalkane, the at least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane has 6 to 6 carbon atoms. It is preferably a cycloalkane that may be substituted with 16 aryl, a heteroaryl having 2 to 22 carbon atoms, an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.

At least one hydrogen in the compound represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9) is deuterium, cyano or It may be replaced with halogen.

The compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), and (9) are each represented by the above formula (tR). It is preferable that the structure contains at least one tertiary alkyl. In particular, one or more of the substituents of the ring to which R ^b1 , R ^b2 , and Formula Het are bonded in each of the formulas (2) and (7), and R ²¹ to each of the formulas (3) and (4) Any one or more of R ²⁴ , any one or more of R ²¹ to R ²⁴ and R ³¹ to R ³⁴ in each of the formulas (5) and (6), and any one of R ⁴¹ to R ⁴⁴ in the formula (8). One or more, and any one or more of R ³¹ to R ³⁴ and R ⁴¹ to R ^{44 in} the formula (9) are represented by the above formula (tR), such as tertiary-alkyl (t-butyl or t-amyl). ), Neopentyl or adamantyl-containing substituents are preferred.

Of the polycyclic aromatic compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9) or their multimers, the formulas The polycyclic aromatic compound represented by (3), (4), (5), (6), (7), (8), or (9) or a multimer thereof is more preferable, and the formula (3), The polycyclic aromatic compound represented by (4) or a multimer thereof is more preferable.

Equation (12), (13), (14), (15), (16), (17), (18), in (19) and ^{^{(20), R 1 ~ R}} 3 and ^R 8 ^{~ R 11} is , Independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl , Alkoxy, aryloxy, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. .. R ¹ ~ ^{R 3} and ^R 8 ^{~ R 11} are each independently hydrogen, aryl of 6 to 30 carbon atoms, heteroaryl of 2-30 carbon atoms, diarylamino (where aryl is an aryl having 6 to 12 carbon atoms ), Diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), or an alkyl having 1 to 24 carbon atoms. preferable.

In formulas (12), (13), (14), (15), (16), (17), (18), (19) and (20), R ⁵¹ to R ⁵⁸ and R ⁶¹ to R ⁶⁸ are , Independently, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl , Cycloalkyl, alkoxy, aryloxy, or substituted silyls, wherein at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. R ⁵¹ to R ⁵⁸ and R ⁶¹ to R ⁶⁸ are independently hydrogen, aryl with 6 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, and diarylamino (where aryl is aryl with 6 to 12 carbon atoms). ), Diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, and 3 to 24 carbon atoms. It is preferably 24 cycloalkyl or trialkylsilyl (where alkyl is an alkyl having 1 to 6 carbon atoms).

Equation (12), (13), (14), (15), (16), (17), (18), (19) and (20) in ^the adjacent groups of R 1 ~ ^{R 3} together Are bonded together with the a ring, adjacent groups of R ⁸ to R ¹¹ are bonded to each other with the b ring, and adjacent groups of R ⁵¹ to R ⁵⁴ are bonded to each other with the c51 ring, and the R ⁵⁵ Adjacent groups of ~ R ⁵⁸ are bonded together with the c55 ring, adjacent groups of R ⁶¹ to R ⁶⁴ are bonded together with the b61 ring, and adjacent groups of R ⁶⁵ to R ⁶⁸ are bonded together. They may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b65 ring, respectively, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, aryl. Heteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyls may be substituted. The aryl ring or heteroaryl ring formed is preferably an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen in the formed ring has 6 to 10 carbon atoms. It may be substituted with aryl, alkyl having 1 to 12 carbon atoms, or cycloalkyl or trialkylsilyl having 3 to 16 carbon atoms (where alkyl is alkyl having 1 to 4 carbon atoms).

Equation (12), (13), (14), (15), (16), (17), (18), (19) and ^{R 2} is in (20), alkyl (methyl, t- butyl, etc.) , Substituted phenyl (2,6, dimethylphenyl, etc.), diarylamino (diphenylamino, etc.) or carbazolyl (N-carbazolyl, etc.). Further, it is preferable that R ¹ and R ³ , which are groups other than R ² in the a ring, are hydrogen, respectively.

In equations (12), (13), (14), (15), (16), (17), (18), (19) and (20), X is independently>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C (-R) ₂ . The R of>N-R,> Si (-R) ₂ , or> C (-R) ₂ is hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, preferably an aryl having 6 to 30 carbon atoms. Heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms. > R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. > R in C (—R) ₂ is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. .. Further, X is preferably>O,>S,> N-R, or> C (-R) ₂ , more preferably>O,> S, or> N-R, and> O or. > S is even more preferred.

In equations (12), (13), (14), (15), (16), (17), (18), (19) and (20), Y ¹ is independently B and P, respectively. , P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and the R of the Si-R and Ge-R is an aryl having 6 to 12 carbon atoms and 1 to 1 to carbon atoms. It is an alkyl of 6 or a cycloalkyl of 3 to 14 carbon atoms. As Y ¹ , B, P, P = O, P = S, or Si—R is preferable, and B is particularly preferable.

In formulas (12), (13), (14), (15), (16), (17), (18), (19) and (20), X ¹ and X ² are independent of each other. >O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se, and the R of> N-R and> Si (-R) ₂ is Independently, hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, a heteroaryl which may have 2 to 15 carbon atoms which may be substituted, and an alkyl having 1 to 6 carbon atoms which may be substituted. Alternatively, it is a cycloalkyl having 3 to 14 carbon atoms which may be substituted, and R of> C (-R) ₂ is hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, and is substituted. It may be a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms which may be substituted, or a cycloalkyl having 3 to 14 carbon atoms which may be substituted, and the above-mentioned> NR. ,> Si (-R) ₂ and> C (-R) ₂ R in at least one of -O-, -S-, -C (-R) _2- , or a ring by a single bond, It may be bonded to at least one ring selected from the group consisting of the b ring, the c51 ring, and the b61 ring.

Consists of aryl and heteroaryl rings in the compounds represented by formulas (12), (13), (14), (15), (16), (17), (18), (19) or (20). At least one selected from the group (at least one of the a ring, b ring, c51 ring, c55 ring, b61 ring, b65 ring, the formed ring, the aryl, and the heteroaryl) has 3 carbon atoms. It may be condensed with at least one cycloalkane of ~ 24, and at least one hydrogen in the cycloalkane is an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, and 1 to 24 carbon atoms. It may be substituted with an alkyl or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH _2- in the cycloalkane may be substituted with -O-.
Consists of an aryl ring and a heteroaryl ring in the compound represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19) or (20). When at least one selected from the group is condensed with at least one cycloalkane, the at least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is carbon. It is preferably a cycloalkane that may be substituted with an aryl of number 6 to 16, a heteroaryl having 2 to 22 carbon atoms, an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.

At least one hydrogen in the compound represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19) or (20) is deuterium. , Can be substituted with cyano or halogen.

The compounds represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19) or (20) are represented by the above formula (tR). It is preferable that the structure contains at least one tertiary alkyl represented. In particular, in each of the formulas (12), (13), (14), (15), (16), (17), (18), (19) and (20), R ⁵¹ to R ⁵⁸ and R ⁶¹ It is preferable that any of 1 to R ⁶⁸ is a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.) represented by the above formula (tR), neopentyl, or adamantyl.

Equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), ( 10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18- In 1), (19-1) and (20-1), Z is independently CR ^z or N, at least one Z is N, and R ^z is independently hydrogen. , Aryl, Heteroaryl, Diarylamino, Diheteroarylamino, Arylheteroarylamino, Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryl It is an oxy, or substituted silyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. R ^z is independently hydrogen, aryl with 6 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, diarylamino (where aryl is aryl with 6 to 12 carbon atoms), and diallylboryl (where aryl is carbon). It is preferably an aryl of number 6-12, and the two aryls may be bonded via a single bond or a linking group), or an alkyl having 1 to 24 carbon atoms.

Equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), ( 10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18- In 1), (19-1) and (20-1), adjacent groups of R ^{z in} the a'ring are bonded to each other and together with the a'ring, adjacent to the R ^z in the b'ring. 'together with the ring, c' b and groups to each other bound to 'with ring, c21' c adjacent groups are bonded to one of R ^z in the ring adjacent groups of R ^z in the ring bonded to c21 'with ring, b31' b31 'with ring, b15' adjacent groups are bonded to one of R ^z in the ring adjacent groups of R ^z in the ring is bonded to b15 'together with the ring, a12''together with the ring, b41' a12 adjacent groups are bonded to one of R ^z in the ring b41 'with ring adjacent groups are bonded to one of R ^z in the ring, c51 with ring 'c51 adjacent groups are bonded to one of R ^z in the ring', c55 with ring 'c55 adjacent groups are bonded to one of R ^z in the ring', b61 'in the ring of b61 'together with the ring, b65' adjacent groups are bonded to one of R ^z b65 'with ring, c70' adjacent groups are bonded to one of R ^z in the ring of R ^z in the ring Adjacent groups are bonded to each other to form a c70'ring, and adjacent groups of R ^z in the b70'ring are bonded to each other to form an aryl ring or a heteroaryl ring, respectively. At least one hydrogen in the formed ring may be aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, diarylboryl (two aryls bonded via a single bond or a linking group). It may be substituted), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. The aryl ring or heteroaryl ring formed is preferably an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen in the formed ring has 6 to 10 carbon atoms. It may be substituted with aryl, alkyl having 1 to 12 carbon atoms, or cycloalkyl or trialkylsilyl having 3 to 16 carbon atoms (where alkyl is alkyl having 1 to 4 carbon atoms).

Equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), ( 10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18- In each of 1), (19-1), and (20-1), the number of rings (monocycles) containing Z, which is N, is preferably 1 to 4, and more preferably 1 to 3. It is more preferably 1 to 2 pieces, and particularly preferably 1 piece. Equations (2-1), (3-1), (4-1), (5-1), (6-1), (10-1), (11-1), (12-1), ( In each of 13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1), At least a ring containing Z in which the a'ring is N is preferable, and a ring containing Z in which only the a'ring is N is more preferable. Further, in each of the formulas (7-1), (8-1), and (9-1), it is preferable that the ring contains Z in which at least the a'ring and the a12'ring are N, and the a'ring and the a'ring are preferable. It is more preferable that the ring contains Z in which only the a12'ring is N. Equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), ( 10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18- In 1), (19-1), and (20-1), in the ring (monocycle) containing Z which is N, it is preferable that one or two of the plurality of Zs are N, and two are N. When N, it is preferable that the two Ns are not adjacent to each other. The ring (monocycle) containing Z, which is N, is preferably a pyridine ring or a pyrimidine ring. When the a'ring is a ring containing Z which is N, a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring is preferable, and a pyridine ring or a pyrimidine ring is more preferable.

Equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), ( 10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18- In 1), (19-1), and (20-1), X is independently>O,>S,>Se,>N-R,> Si (-R) ₂ , or> C. (-R) ₂ . The Rs of>N-R,> Si (-R) ₂ or> C (-R) ₂ are independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, and the two Rs are bonded to each other. Aryl may have 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms. > R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. > R in C (—R) ₂ is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. .. Further, X is preferably>O,>S,> N-R, or> C (-R) ₂ , more preferably>O,> S, or> N-R, and> O or. > S is even more preferred.

Equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), ( 10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18- In 1), (19-1), and (20-1), Y ¹ is independently B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge. -R, and R of the Si—R and Ge—R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. As Y ¹ , B, P, P = O, P = S, or Si—R is preferable, and B is particularly preferable.

Equations (2-1), (3-1), (4-1), (5-1), (6-1), (10-1), (11-1), (12-1), ( X in 13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1) ¹ and X ² and X ¹ , X ² , X ³ and X ⁴ in equations (7-1), (8-1) and (9-1) are independently> O, respectively. >N-R,> Si (-R) ₂ ,> C (-R) ₂ ,> S, or> Se, and the R of> N-R and> Si (-R) ₂ are independent of each other. The aryl may be substituted with 6 to 12 carbon atoms, the heteroaryl may be substituted with 2 to 15 carbon atoms, the alkyl may be substituted with 1 to 6 carbon atoms, or the moiety is substituted. It is a cycloalkyl having 3 to 14 carbon atoms, and R of> C (-R) ₂ is hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, and 2 carbon atoms which may be substituted. It is a heteroaryl of up to 15, an alkyl having 1 to 6 carbon atoms which may be substituted, or a cycloalkyl having 3 to 14 carbon atoms which may be substituted, and the above-mentioned>NR,> Si (-). R in at least one of R) ₂ and> C (-R) ₂ is -O-, -S-, -C (-R) _2- , or by a single bond, a'ring, b'ring, At least one selected from the group consisting of a c'ring, an a12'ring, a b15'ring, a 5-membered ring fused to a c21'ring, a 5-membered ring fused to a b31'ring, a c51'ring, and a b61'ring. It may be bonded to the ring.

Equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), ( 10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18- 1) In at least one (a'ring, b'ring, c'ring, selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by (19-1) or (20-1), Of the c21', b31' ring, b15' ring, a12' ring, b41' ring, c51' ring, c55' ring, b61' ring, b65' ring, the formed ring, the aryl, and the heteroaryl. At least one) may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane has an aryl having 6 to 30 carbon atoms and 2 to 30 carbon atoms. It may be substituted with heteroaryl, an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH _2- in the cycloalkane may be substituted with -O-.

Equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), ( 10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18- 1) When at least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound represented by (19-1) or (20-1) is condensed with at least one cycloalkane, at least 1 One cycloalkane is a cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane has an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 carbon atoms, and 1 to 12 carbon atoms. It is preferably a cycloalkane that may be substituted with an alkyl or a cycloalkyl having 3 to 16 carbon atoms.

Equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), ( 10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18- 1) At least one hydrogen in the compounds represented by (19-1) and (20-1) may be substituted with deuterium, cyano, or halogen.

Equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), ( 10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18- The compound represented by 1), (19-1) or (20-1) is a tertiary alkyl (t-butyl, t-amyl, etc.), neopentyl, or adamantyl represented by the above formula (tR). A structure containing at least one is preferable.

The compound (1F-86) and the compound (1F-87) of the examples are a ring (pyridine ring) containing Z in which only the a'ring is N in the formulas (4-1) and (13-1), respectively. It corresponds to the compound which is. As shown in Examples (Table 2), it can be seen that an organic EL device using these compounds in the light emitting layer has a long time to maintain high brightness and can improve the device life.

As described above, Eq. (1) or Eq. (2), (3), (4), (5), (6), (7), (8), (9) (12), (13) , (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5- 1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1) , (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) or (20-1). At least one of the aryl and heteroaryl rings in the chemical structure of the compound and its multimers may be condensed with at least one cycloalkane. By using the compound of the present invention having such a structure as a light emitting material, the luminous efficiency and the device life can be further improved.

For example, A ring, B ring, C ring, a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, b41 ring, c51 ring, c55 ring, b61 ring, b65 ring, a'ring. , B'ring, c'ring, c21'ring, b31'ring, b15'ring, a12'ring, b41'ring, c51'ring, c55'ring, b61'ring, b65'ring, aryl ring and In heteroaryl rings, aryl and heteroaryl rings in fused rings, and aryls as first and second substituents in rings A-C (aryl, diallylamino, arylheteroarylamino, diallylboryl or aryloxy). Aryl moiety) and heteroaryl (heteroaryl, diheteroarylamino or heteroaryl moiety in aryl heteroarylamino), a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, b41 ring, c51 ring, c55 ring, b61 ring, (as above) aryl (as above) and heteroaryl in the first and second substituent to b65 ring, the Si-R and Ge-R is ^{Y 1} R Aryl as R (similar to above), and aryl as R of>N-R,> Si (-R) ₂ and> C (-R) ₂ which are X ¹ , X ² , X ³ , X ⁴ At least one of (similar to above) and heteroaryl (similar to above) may be condensed with at least one cycloalcan.

Preferably, A ring, B ring, C ring, a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, b41 ring, c51 ring, c55 ring, b61 ring, b65 ring, a'. Aryl ring which is a ring, b'ring, c'ring, c21'ring, b31'ring, b15'ring, a12'ring, b41'ring, c51'ring, c55'ring, b61'ring, b65'ring. And the heteroaryl ring, aryl (aryl moiety in aryl, diarylamino, diarylboryl or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituent in rings A to C. ), Aryl (same as above) and heteroaryl (same as above) as the first substituents on rings a to c, and X ¹ , X ² , X ³ , X ⁴ > NR. ,> Si (-R) ₂ and> C (-R) ₂ as R, at least one of aryl (same as above) and heteroaryl (similar to above) is condensed with at least one cycloalcan. You may.

More preferably, A ring, B ring, C ring, a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, b41 ring, c51 ring, c55 ring, b61 ring, b65 ring, a. Aryl that is'ring, b'ring, c'ring, c21'ring, b31'ring, b15'ring, a12'ring, b41'ring, c51'ring, c55'ring, b61'ring, b65'ring. Rings, aryl (aryl moiety in aryl or diarylamino) and heteroaryl (heteroaryl moiety in heteroaryl) as the first substituent in rings A to C, a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, b41 ring, c51 ring, c55 ring, b61 ring, b65 ring, a'ring, b'ring, c'ring, c21'ring, b31'ring, b15'ring, a12' Aryl (same as above) and heteroaryl (same as above) and X ¹ as first substituents on rings, b41'-rings, c51'-rings, c55'-rings, b61'-rings, b65'-rings. , X ² , X ³ , X ⁴ >N-R,> Si (-R) ₂ and> C (-R) ₂ at least one of the aryls as R (similar to the above) is at least 1. It may be condensed with one cycloalgecan.

More preferably, A ring, B ring, C ring, a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, b41 ring, c51 ring, c55 ring, b61 ring, b65 ring, a. Aryl that is'ring, b'ring, c'ring, c21'ring, b31'ring, b15'ring, a12'ring, b41'ring, c51'ring, c55'ring, b61'ring, b65'ring. Rings, aryl (aryl moiety in aryl or diarylamino) as the first substituent in rings A to C, a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, b41 ring , C51 ring, c55 ring, b61 ring, b65 ring, a'ring, b'ring, c'ring, c21'ring, b31'ring, b15' ring, a12' ring, b41' ring, c51' ring, c55 Aryl as the first substituent on the'ring, b61', b65' ring (same as above), and X ¹ , X ² , X ³ , X ⁴ >N-R,> Si ( At least one of the aryl as R of —R) ₂ and> C (−R) ₂ (similar to the above) may be condensed with at least one cycloalgecan.

Examples of the "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, and cycloalkanes having 5 to 10 carbon atoms. Examples thereof include alkanes, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo [1.0.1] butane, bicyclo [1.1.1] pentane, Bicyclo [2.0.1] pentane, bicyclo [1.2.1] hexane, bicyclo [3.0.1] hexane, bicyclo [2.1.2] heptane, bicyclo [2.2.2] octane, Examples thereof include adamantane, diamantane, decahydronaphthalene and decahydroazulene, and alkyl (particularly methyl) substituents, halogen (particularly fluorine) substitutes and dehydrohydrone substitutes having 1 to 5 carbon atoms thereof.

Among these, at least one hydrogen in the α-position carbon of cycloalkane (the carbon at the position adjacent to the carbon at the condensation site in the cycloalkyl condensed on the aryl ring or the heteroaryl ring) as shown in the following structural formula, for example. The structure in which is substituted is preferable, the structure in which two hydrogens are substituted in the carbon at the α-position is more preferable, and the structure in which a total of four hydrogens are substituted in the carbon at the α-position is further preferable. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent.

The number of cycloalkanes condensed on one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are condensed on one benzene ring (phenyl) is shown below. * Indicates the bond position and may be any carbon that constitutes a benzene ring and does not constitute a cycloalkane. Cycloalkanes condensed as in the formulas (Cy-1-4) and (Cy-2-4) may be condensed with each other. Even if the ring (group) to be condensed is an aryl ring or a heteroaryl ring other than the benzene ring (phenyl), the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. Is the same.

At least one -CH _2- in the cycloalkane may be substituted with -O-. For example, an example in which one or more -CH _2- is replaced with -O- in a cycloalkane condensed on one benzene ring (phenyl) is shown below. Even if the ring (group) to be condensed is an aromatic ring or a heteroaromatic ring other than the benzene ring (phenyl), the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. Even if there is, it is the same.

At least one hydrogen in the cycloalkane may be substituted, and the substituents include, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded). (Or may be attached via a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, dehydrogen, cyano or halogen, the details of which are described above in the first substituent. The explanation can be quoted. Among these substituents, alkyl (for example, alkyl having 1 to 6 carbon atoms), cycloalkyl (for example, cycloalkyl having 3 to 14 carbon atoms), halogen (for example, fluorine), deuterium and the like are preferable. Further, when cycloalkyl is substituted, a substituted form forming a spiro structure may be used, and an example thereof is shown below.

As the form of cycloalkane condensation, first, the A ring, the B ring, and the C ring in the formula (1) (formulas (2), (3), (4), (5), (6), (7), ( 8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), ( 3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11- 1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) , Or a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, b41 ring, c51 ring, c55 ring, b61 ring, b65 ring, a'ring, b'in (20-1). Aryl ring and heteroaryl which are (ring, c'ring, c21'ring, b31'ring, b15'ring, a12'ring, b41'ring, c51'ring, c55'ring, b61'ring, b65'ring). Examples thereof include a ring, an aryl ring in a condensed ring, and a heteroaryl ring condensed with cycloalkane. In particular, the b-ring of formula (3) (particularly as R ⁹ and R ¹⁰ combine to form a ring), the c21 ring of formula (3), and the b-ring of formula (4) (particularly R ⁹ and R ^10). The c21 ring of the formula (4) (particularly so that R ²² and R ²³ are bonded to form a ring) is condensed with a cycloalkane (so that they are bonded to form a ring).

Other forms of cycloalkane condensation include formulas (1) or (2), (3), (4), (5), (6), (7), (8), (9), (12). ), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1) ), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), Tables of (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), or (20-1). The polycyclic aromatic compound and its multimer are, for example,> NR in which R is condensed with cycloalkane> NR, diarylamino condensed with cycloalkane (condensed to this aryl moiety), cycloalkane. Examples include condensed carbazolyl (condensed on this benzene ring portion) or benzocarbazolyl condensed with cycloalkane (condensed on this benzene ring portion). Examples of the "diarylamino" include the groups described as the "first substituent" above.

Further, as more specific examples, the equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13) , (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5- 1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1) , (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), or (20-1). family compound and R ² in the multimers, eg a condensed diarylamino with cycloalkane (this condensation to aryl moiety) or fused carbazolyl with cycloalkane (fused to the benzene ring portion) and the like.

An example of this is a polycyclic aromatic compound represented by the following formula (2-A) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2-A). Cy is a cycloalkane, n is an independently integer of 1 to 3 (preferably 1), and "= (Cy) n" is at an arbitrary position in the structure in which n cycloalkanes are to be condensed. It means to condense (in the following formula (2-A), n cycloalkanes are condensed on the benzene ring (phenyl)), and the definition of each code in the structural formula is the definition of each code in the formula (2). Same as definition. In the following equation, at least one of the a ring, the b ring and the c ring is the equation (2), (3), (4), (5), (6), (7), (8). ), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3) -1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1) ), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), Alternatively, it shall be a fused ring according to the provisions of (20-1).

Specific examples thereof include compounds represented by the following formulas. "Cy" in the following formula represents cycloalkane, and n is a number that can be independently condensed from 0 to the maximum (however, not all n becomes 0), preferably 0 to 2 (however, all n). Is never 0), more preferably 1, and "= (Cy) n" means that n cycloalkanes are condensed at an arbitrary position in the structure to be condensed (for example, the following formula "1-". In "Cy- (1)", it means that n cycloalkanes are condensed at an arbitrary position on each benzene ring). In the following structural formula, "OPh" indicates phenoxy and "Me" indicates methyl, and each compound may be substituted with the above-mentioned first substituent and second substituent. In the following formula, at least one of the rings bonded to the element corresponding to Y ¹ in the formula (1) is the formulas (2), (3), (4), (5), (6), ( 7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2- 1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1) , (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), ( A condensation composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring according to the provisions of 19-1) or (20-1). It shall be a ring.

The polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device. Examples of the organic device include an organic electroluminescent device, an organic field effect transistor, and an organic thin film solar cell. In particular, in an organic electroluminescent device, as a dopant material for the light emitting layer, a compound in which Y ¹ is B, X ¹ and X ² (and X ³ and X ⁴ ) is> NR in any of the above formulas. Compounds where Y ¹ is B, X ¹ (and X ⁴ or X ³ ) is> O, X ² (and X ³ or X ⁴ ) is> NR, Y ¹ is B, X ¹ and X ² (and Compounds in which X ³ and X ⁴ ) are> O, compounds in which Y ¹ is B, X ¹ and X ² (and X ³ and X ⁴ ) are> C (-R) ₂ , are preferred, and Y ¹ is B, Compounds where X ¹ and X ² (and X ³ and X ⁴ ) are> N-R, Y ¹ is B, X ¹ and X ² (and X ³ and X ⁴ ) are> C (-R) ₂ . Compounds are more preferred, with compounds having Y ¹ of B, X ¹ and X ² (and X ³ and X ⁴ )> N-R being most preferred. As the host material of the light emitting layer, Y ¹ is B, X ¹ (and X ⁴ or X ³ ) is> O, X ² (and X ³ or X ⁴ ) is> NR, Y ¹ is B, Compounds in which X ¹ and X ² (and X ³ and X ⁴ ) are> O are preferred, with Y ¹ being B, X ¹ and X ² (and X ³ and X ⁴ ) being> O as electron transport materials. Compounds, compounds in which Y ¹ is P = O, X ¹ and X ² (and X ³ and X ⁴ ) are> O, are preferably used.

A more specific example of the polycyclic aromatic compound of the present invention is a compound represented by the following structural formula. In the following structural formula, "D" indicates deuterium, "Me" indicates methyl, "tBu" indicates t-butyl, and "tAm" indicates t-amyl.

The polycyclic aromatic compound represented by the formula (1) and its multimer according to the present invention are polymer compounds obtained by polymerizing a reactive compound in which a reactive substituent is substituted therein as a monomer (this polymer). The monomer for obtaining a compound has a polymerizable substituent) or a polymer crosslinked product obtained by further cross-linking the polymer compound (the polymer compound for obtaining this polymer crosslinked product has a crosslinkable substituent). (Having), or a pendant type polymer compound obtained by reacting a main chain type polymer with the above-mentioned reactive compound (the above-mentioned reactive compound for obtaining this pendant type polymer compound has a reactive substituent), or A material for an organic device can also be used as a pendant type polymer crosslinked product obtained by further cross-linking the pendant type polymer compound (the pendant type polymer compound for obtaining this pendant type polymer crosslinked product has a crosslinkable substituent). For example, it can be used as a material for an organic field light emitting element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.

As the above-mentioned reactive substituent (including the polymerizable substituent, the crosslinkable substituent, and the reactive substituent for obtaining a pendant type polymer, hereinafter, also simply referred to as “reactive substituent”). , A substituent capable of increasing the molecular weight of the polycyclic aromatic compound or its multimer, a substituent capable of further cross-linking the polymer compound thus obtained, and a substituent capable of pendant reaction with a main chain type polymer. The group is not particularly limited, but alkenyl, alkynyl, an unsaturated compound of cycloalkyl (for example, cyclobutenyl), a group in which at least one -CH _2- in cycloalkyl is substituted with -O- (for example, epoxy) is condensed. Examples thereof include an unsaturated compound of cycloalkane (for example, condensed cyclobutene), and substituents having the following structure are preferable. * In each structural formula indicates the bonding position.

L is a single bond, -O-, -S-,> C = O, -OC (= O)-, an alkylene having 1 to 12 carbon atoms, and an oxyalkylene having 1 to 12 carbon atoms, respectively. And a polyoxyalkylene having 1 to 12 carbon atoms. Among the above-mentioned substituents, it is represented by the formula (XLS-1), the formula (XLS-2), the formula (XLS-3), the formula (XLS-9), the formula (XLS-10) or the formula (XLS-17). The group represented by the formula (XLS-1), the formula (XLS-3) or the formula (XLS-17) is more preferable.

Details of the uses of such polymer compounds, polymer crosslinked bodies, pendant type polymer compounds and pendant type polymer crosslinked bodies (hereinafter, also simply referred to as “polymer compounds and polymer crosslinked bodies”) will be described later.

2. 2. Method for Producing Polycyclic Aromatic Compounds and Their Multimers Formulas (1) or (2), (3), (4), (5), (6), (7), (8), (9), The polycyclic aromatic compounds represented by (12), (13), (14), (15), (16), (17), (18), or (19) and their multimers are basically. First, an intermediate is produced by bonding the A ring (a ring), the B ring (b ring), and the C ring (c ring) with a bonding group (a group containing X ¹ and X ² ) (first). reaction), subsequently, a ring (a ring), it is possible to produce a final product by binding ring B (b ring) and C rings (c ring) group comprising a binding group (Y ¹ a) (Second reaction). In the first reaction, for example, in the case of an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used, and in the case of an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. Further, in the second reaction, a tandem hetero-Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same applies hereinafter) can be used. At least one ring selected from the group consisting of A ring, B ring and C ring by using a raw material having a desired fused ring or adding a step of condensing the ring somewhere in the reaction step. The compound can be produced from a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring.

Production Method Via Intermediate-1 The polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For each step below, the description of International Publication No. 2015/102118 can be referred to.
A reaction step of metallizing the halogen atom (Hal) between X ¹ and X ² in the following intermediate-1 using an organic alkaline compound, a halide of Y ¹ , an amination halide of Y ¹ , and a reaction of Y ¹ . a reaction step of exchanging said metal and Y ¹ using a reagent selected from the group consisting of aryloxy compound of alkoxides and Y ^1, wherein the continuous electrophilic aromatic substitution using a Bronsted base method comprising a reaction step of coupling the B ring and C ring Y ^1.

Production Method Via Intermediate-2 The polycyclic aromatic compound of the present invention is preferably produced by a production method including a reaction step of reacting the following intermediate-2 with an acid.

(In Intermediate-2, Z is —B (OH) ₂ which may be esterified.)

Z in Intermediate-2 is —B (OH) ₂ , which may be esterified. Preferred Y ¹ is an esterified group of —B (OH) ₂ .

The group in which -B (OH) ₂ is esterified (-B (OR) ₂ ) is not particularly limited, and examples thereof include groups obtained by the reaction of an alcohol containing a diol or a carboxylic acid with boronic acid. Be done. Examples of R of −B (OR) ₂ include alkyls having 1 to 4 carbon atoms (branched chain alkyls having 3 to 4 carbon atoms) which may be substituted, and Rs are bonded to each other to form a ring. Also, the formed ring may contain an aromatic ring such as benzene. Specifically, the basis of the following structure can be mentioned. In the following structure, "Me" represents methyl, "Et" represents ethyl, "iPr" represents isopropyl, and * represents the binding position.

Method for Producing Boronic Acid or Boronic Acid Ester such as Intermediate-2 The compound represented by Intermediate-2 (boronic acid or boronic acid ester) is basically a ring A (ring a) and a ring B (b). An intermediate is produced by binding the ring) and the C ring (c ring) with a bonding group (X ¹ and X ² ) (first reaction), and then the Y ¹ group is introduced to first obtain boronic acid. An ester can be produced, and the boronic acid can be produced by hydrolyzing the ester. In the first reaction, for example, in the case of an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used, and in the case of an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. The symbols in the structural formulas in each scheme shown below are the same as the above definitions.

The second reaction is to introduce a boronic acid ester such as shown in the following scheme (1) or (2) is Y ¹ to the intermediate obtained in the first reaction Bpin (pinacolato boryl) reaction Is.

In the above schemes (1) and (2), the hydrogen atom is first orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium or the like to be lithiated. Here, a method using n-butyllithium, sec-butyllithium, t-butyllithium, etc. alone has been shown, but N, N, N', N'-tetramethylethylenediamine, etc. are added in order to improve the reactivity. You may. Then, by adding a boronic acid esterification reactant such as 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to the obtained lithiated product, a pinacol ester of boronic acid was added. Can be manufactured. Here, the method using 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is shown, but in addition, trimethoxyborane, triisoprocoxivorane and the like can also be used. .. Further, by applying the method described in International Publication No. 2013/016185, 4,4,5,5-tetramethyl-1,3,2-dioxaborolane and the like can also be used in the same manner.

Further, as shown in the following scheme (3) or (4), boronic acid can be produced by hydrolyzing the boronic acid ester produced by the method of the above scheme (1) or (2).

Further, by allowing an appropriate alcohol to act on the boronic acid esters or boronic acids obtained in the above schemes (1) to (4), different boronic acid esters can be produced through transesterification or reesterification. ..

The above schemes (1) and (2) show a method for producing a boronic acid ester represented by the formula (1) or (2), but have a structure represented by the formula (1) or (2). A multimeric compound having a plurality of esters can be produced by using an intermediate compound having a plurality of A ring (a ring), B ring (b ring) and C ring (c ring). Details will be described in the following schemes (5) to (7). In this case, the target product such as a dimer compound or a trimer compound can be obtained by doubling or tripling the amount of the reagent such as butyllithium to be used.

Although the above schemes (5) to (7) show a method for producing a multimer compound of a boronic acid ester, the boronic acid compound can be produced by hydrolysis according to the above scheme (4), and different ester compounds can also be produced. It can be produced through transesterification or re-esterification using alcohol.

Boronic acid or boronic acid ester having a substituent at a desired position can be synthesized by appropriately selecting the above-mentioned synthesis method and appropriately selecting the raw material to be used.

In the above schemes (1) to (7), lithium was introduced to a desired position by orthometalation, but as in the following schemes (8) or (9), a halogen such as a bromine atom is added to the position where lithium is to be introduced. Lithium can also be introduced at the desired position by introducing and halogen-metal exchange. Then, a boronic acid ester can be produced from the obtained lithium product.

In the above schemes (8) and (9), the halogen atom is first lithiated by performing a halogen-lithium exchange reaction with n-butyllithium, sec-butyllithium, t-butyllithium or the like. Here, a method using n-butyllithium, sec-butyllithium, t-butyllithium, etc. alone has been shown, but N, N, N', N'-tetramethylethylenediamine, etc. are added in order to improve the reactivity. You may. Then, by adding a boronic acid esterification reactant such as 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to the obtained lithiated product, a pinacol ester of boronic acid was added. Can be manufactured. Here, the method using 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is shown, but in addition, trimethoxyborane, triisoprocoxivorane and the like can also be used. .. Further, by applying the method described in International Publication No. 2013/016185, 4,4,5,5-tetramethyl-1,3,2-dioxaborolane and the like can also be used in the same manner.

The above schemes (8) and (9) show a method for producing a boronic acid ester represented by the formula (1) or (2), and the boronic acid ester thus obtained is hydrolyzed. By doing so, boronic acid can be produced (see scheme (3) or (4) above). Further, by allowing an appropriate alcohol to act on these boronic acid esters and boronic acids, different boronic acid esters can be produced through transesterification or reesterification. Further, the multimeric compound having a plurality of structures represented by the formula (1) or (2) is also an intermediate having a plurality of A ring (a ring), B ring (b ring) and C ring (c ring). Can be produced by using (see the above schemes (5) to (7)).

Further, as shown in the following scheme (10) or (11), the bromoated product and bis (pinacolato) diboron or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane and the like are subjected to a palladium catalyst. Boronic acid esters can also be synthesized in the same manner by performing a coupling reaction using and bases.

The above schemes (10) and (11) show a method for producing a boronic acid ester represented by the formula (1) or (2), and the boronic acid ester thus obtained is hydrolyzed. By doing so, boronic acid can be produced (see scheme (3) or (4) above). Further, by allowing an appropriate alcohol to act on these boronic acid esters and boronic acids, different boronic acid esters can be produced through transesterification or reesterification. Further, the multimeric compound having a plurality of structures represented by the formula (1) or (2) is also an intermediate having a plurality of A ring (a ring), B ring (b ring) and C ring (c ring). Can be produced by using (see the above schemes (5) to (7)).

The metallizing reagents used in the halogen-metal exchange reaction in the schemes described so far include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, isopropylmagnesium chloride, and bromide. Examples thereof include isopropylmagnesium, phenylmagnesium chloride, phenylmagnesium bromide and a lithium chloride complex of isopropylmagnesium chloride known as a turbo Grignard reagent.

In addition to the above reagents, the metallizing reagents used in the orthometal exchange reaction in the schemes described so far include lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hex. Examples thereof include organic alkaline compounds such as methyldisilazide, lithium tetramethylpiperidinylmagnesium chloride / lithium chloride complex, and lithium tri-n-butylmagnate.

Furthermore, as additives that accelerate the reaction when alkyllithium is used as the metalation reagent, N, N, N', N'-tetramethylethylenediamine, 1,4-diazabicyclo [2.2.2] octane, etc. Examples thereof include N and N-dimethylpropylene urea.

In addition, the boronic acid or boronic acid ester of the present invention includes those in which at least a part of hydrogen atoms are substituted with deuterium and those in which halogens such as fluorine and chlorine are substituted. Compounds and the like can be synthesized in the same manner as described above by using a raw material in which desired portions are deuterated, fluorinated or chlorinated.

Method for Producing Polycyclic Aromatic Compound from Boronic Acid of Intermediate-2 Compound Next, a polycyclic aromatic compound and polycyclic using a boronic acid or boronic acid ester represented by intermediate-2 compound or the like. A method for producing an aromatic multimer compound will be described. The symbols in the structural formulas in each scheme shown below are the same as the above definitions.

In the following scheme (12) or (13), a polycyclic aromatic compound is produced by reacting a boronic acid or a boronic acid ester represented by an intermediate-2 compound or the like with a Lewis acid such as aluminum chloride. Can be done.

Bronsted acids such as p-toluenesulfonic acid can also be used. In particular, when the reaction is carried out using Lewis acid, a base such as diisopropylethylamine may be added in order to improve the selectivity and yield.

Further, a polycyclic aromatic multimeric compound can also be produced by using the multimeric compounds having a plurality of structures represented by intermediate-2 by the methods shown in the following schemes (14) to (16). .. In this case, the target product such as a dimer compound or a trimer compound can be obtained by doubling or triple the amount of the reagent such as aluminum chloride used according to the structure of the multimer compound. it can.

The Lewis acids used in the above schemes (12) to (16) include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ , OEt ₂ , BCl ₃ , BBr ₃ , GaCl ₃ , GaBr ₃ , InCl ₃ , InBr ₃ , and so on. In (OTf) ₃ , SnCl ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc (OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn (OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg (OTf) ₂ , LiOTf, Na _{_{_{, KOTf, Me 3 SiOTf, Cu}}} (OTf) such as _{_{_{2, CuCl 2, YCl 3,}}} Y (OTf) 3, TiCl 4, TiBr 4, ZrCl 4, ZrBr 4, FeCl 3, FeBr 3, CoCl 3, CoBr 3 is can give. Further, those in which these Lewis acids are supported on a solid can also be used in the same manner.

Examples of the blended acid used in the above schemes (12) to (16) include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carborane acid, trifluoroacetic acid, and (trifluoromethanesulfonyl) imide. , Tris (trifluoromethanesulfonyl) methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride and the like. Examples of solid Bronsted acids include Amberlist (trade name: Dow Chemical), Nafion (trade name: DuPont), zeolite, and TAYCA Cure (trade name: TAYCA Corporation).

Examples of the amines that may be added in the above schemes (12) to (16) include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo [2.2.2] octane, N, N-dimethyl-p-toluidine, and the like. Examples thereof include N, N-dimethylaniline, pyridine, 2,6-lutidine, and 2,6-di-t-butylamine.

The solvents used in the above schemes (12) to (16) include o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2. , 4-Trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, methyl-t-butyl ether and the like.

Next, as an example, when Y ¹ is a phosphorus sulfide, a phosphorus oxide or a phosphorus atom, and X ¹ and X ² are oxygen atoms, the following schemes (17-1), (17-2), (18) to ( 19). As before, first ortho-metalated with n- butyl lithium, etc. a hydrogen atom between X ¹ and X ^2. Then, phosphorus trichloride were added in the order of sulfur, finally by adding three Lewis acid such as aluminum chloride and N, Bronsted base such as N- diisopropylethylamine, tandem phosphorylase Fafu Riedel is Crafts reaction, Y ¹ is phosphorus A compound that is a sulfide can be obtained. The obtained Rinsurufido compound Y ¹ is able to obtain the compound is a phosphorus oxide by treatment with at m- chloroperbenzoic acid (m-CPBA), Y ¹ by treatment with triethyl phosphine phosphorus A compound that is an atom can be obtained.

Also, for multimers when Y ¹ is phosphor sulfide and X ¹ and X ² are oxygen atoms, halogens such as bromine atoms and chlorine atoms are located at the positions where lithium is to be introduced as in the above schemes (6) and (7). Lithium can also be introduced at the desired position by halogen-metal exchange (schedules (20), (21) and (22) below). Further, the multimers in the case where Y ¹ is phosphor sulfide and X ¹ and X ² are oxygen atoms thus formed are also m-chloroperbenzoic acid (m-chloroperbenzoic acid (19) as in the above schemes (18) and (19). Treatment with m-CPBA) can give a compound in which Y ¹ is a phosphorus oxide, and treatment with triethylphosphine can give a compound in which Y ¹ is a phosphorus atom.

Here, an example in which Y ¹ is B, P, P = O or P = S, and X ¹ and X ² are O or NR has been described. However, by appropriately changing the raw materials, Y ¹ can be changed to Compounds that are Al, Ga, As, Si-R or Ge-R, and compounds in which X ¹ and X ² are S can also be synthesized.

Specific examples of the solvent used in the above reaction are t-butylbenzene, xylene and the like.

Further, in Formula (2), a ring, b aryl or heteroaryl ring adjacent groups is a ring attached, with b ring or c ring of the rings and c ring substituents R ^{1 ~} R ¹¹ At least one hydrogen in the formed ring may be substituted with aryl or heteroaryl. Therefore, the polycyclic aromatic compound represented by the formula (2) has the formulas (2-1) of the following schemes (23) and (24) depending on the mutual bonding form of the substituents in the a ring, the b ring and the c ring. ) And the formula (2-2), the ring structure constituting the compound changes. These compounds can be synthesized by applying the synthetic methods shown in the above schemes (1) to (19) to the intermediates shown in the following schemes (23) and (24).

Equation (2-1) and ring A ', B' in the formula (2-2) ring and C 'ring, and adjacent groups are bonded of the substituents ^R 1 ^{~ R 11,} respectively a ring , An aryl ring or a heteroaryl ring formed together with the b ring and the c ring (it can also be said to be a fused ring formed by condensing another ring structure on the a ring, the b ring or the c ring). Although not shown in the formula, there are some compounds in which all of the a ring, b ring and c ring are changed to A'ring, B'ring and C'ring.

Further, R in at least one of "the above>N-R,> Si (-R) ₂ and> C (-R) _{2 in} the formula (2) is -O-, -S-, -C (-R). ) ₂ -or is bonded to at least one ring of the a ring, b ring and c ring by a single bond "is expressed by the formula (2-3-1) of the following scheme (25). A compound having a ring structure in which X ¹ and X ² are incorporated into the fused ring B'and the condensed ring C', or represented by the formulas (2-3-2) and (2-3-3). It can be represented by a compound having a ring structure in which X ¹ and X ² are incorporated into the fused ring A'. These compounds can be synthesized by applying the synthetic methods shown in the above schemes (1) to (19) to the intermediates shown in the following scheme (25).

Further, in the synthetic methods of the above schemes (17-1) (17-2) and (20) to (25), hydrogen between X ¹ and X ² is used before adding boron trichloride, boron tribromide, or the like. An example of tandem heterofree del crafts reaction by orthometalating an atom (or halogen atom) with butyllithium or the like was shown, but boron tribromide or boron trichloride was shown without orthometalation using butyllithium or the like. The reaction can also be allowed to proceed by adding boron tribromide or the like.

When Y ¹ is phosphorus-based, the hydrogen atom between X ¹ and X ² (O in the following formula) is n-butyllithium, sec-, as shown in the following schemes (26) and (27). Orthometallation with butyllithium or t-butyllithium, then bisdiethylaminochlorophosphine is added, lithium-phosphorus metal exchange is performed, and then Lewis acid such as aluminum trichloride is added to tandem phosphafreedelcrafts. The desired product can be obtained by reacting. This reaction method is also described in International Publication No. 2010/104047 (for example, page 27).

Also in the above schemes (26) and (27), a multimeric compound is synthesized by using an orthometalation reagent such as butyllithium in a molar amount twice or three times the molar amount of intermediate 1. can do. Further, a halogen such as a bromine atom or a chlorine atom is introduced in advance at a position where a metal such as lithium is to be introduced, and the metal can be introduced at a desired position by exchanging the halogen-metal.

Further, for the compound condensed with cycloalkane, a desired position can be obtained by using a raw material condensed with cycloalkane or adding a step of condensing cycloalkane somewhere in the reaction step in each scheme. Can produce cycloalkane-condensed compounds.

In addition, for the polycyclic aromatic compound represented by the formula (2-A), a cycloalkane-condensed intermediate is synthesized and the desired position is formed by cyclizing the intermediate as in the following scheme (28). Can synthesize polycyclic aromatic compounds condensed with cycloalkane. In scheme (28), X represents halogen or hydrogen, and the definitions of other codes are the same as the definitions of codes in formula (2).

The pre-cyclization intermediate in scheme (28) also has a desired substituent by appropriately combining a Buchwald-Hartwig reaction, a Suzuki coupling reaction, an etherification reaction by a nucleophilic substitution reaction, an Ullmann reaction, or the like. Intermediates can be synthesized. In these reactions, commercially available products can also be used as the raw material to be the precursor of cycloalkane condensation.

The compound of formula (2-A) having a cycloalkane-condensed diphenylamino can also be synthesized by, for example, the following method. That is, when diphenylamino which is cycloalkane-condensed bromobenzene and trihalogenated aniline is introduced by an amination reaction such as Buchwald-Hartwig reaction, and then X ¹ and X ² are N-R. Is induced to the intermediate (M-3) by etheration with phenol when X ¹ and X ² are O in an amination reaction such as Buchwald-Hartwig reaction, and then, for example, butyl lithium. Tandem Bora Friedelcrafts by acting a metallizing reagent such as, transmetallating, then a boron halide such as boron tribromide, and then a blended base such as diethylisopropylamine. By the reaction, the compound of the formula (2-A) can be synthesized. These reactions can also be applied to other cycloalkane condensed compounds.

The orthometallation reagents used in the above scheme include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium and t-butyllithium, lithium diisopropylamide, lithium tetramethylpiperidide and lithium hexamethyl. Examples thereof include organic alkali compounds such as disilamide and potassium hexamethyldisilazide, and dispersed alkali metals such as organic solvent-dispersed Na.

As the metal exchange reagent metal -Y ¹ used in the above scheme, the three fluoride ^{Y 1,} trichloride of ^{Y 1,} halogen ^{Y 1} such tribromide, triiodide of ^{Y 1} of ^{Y 1} Examples thereof include isomers, Y ¹ amination halides such as CIPN (NET ₂ ) ₂ , Y ¹ alkoxides, and Y ¹ aryl bromides.

The blended bases used in the above scheme include N, N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N, N-Dimethylaniline, N, N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar ₄ BNa, Ar ₄ BK, Ar ₃ B, Examples thereof include Ar ₄ Si (where Ar is an aryl such as phenyl).

Lewis acids used in the above scheme include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ , OEt ₂ , BCl ₃ , BBr ₃ , GaCl ₃ , GaBr ₃ , InCl ₃ , InBr ₃ , In (OTf) ₃ , SnCl. _{_{_{4, SnBr 4, AgOTf, ScCl}}} 3, Sc (OTf) 3, ZnCl 2, ZnBr 2, Zn (OTf) 2, MgCl 2, MgBr 2, Mg (OTf) 2, LiOTf, NaOTf, KOTf, Me 3 SiOTf, Examples thereof include Cu (OTf) ₂ , CuCl ₂ , YCl ₃ , Y (OTf) ₃ , TiCl ₄ , TiBr ₄ , ZrCl ₄ , ZrBr ₄ , FeCl ₃ , FeBr ₃ , CoCl ₃ , and CoBr ₃ .

In the above scheme, Bronsted bases or Lewis acids may be used to facilitate the tandem hetero-Friedel-Crafts reaction. However, when Y ¹ halides such as Y ¹ trifluoride, Y ¹ trichloride, Y ¹ tribromide, and Y ¹ triiodide are used, as the aromatic electrophobic substitution reaction progresses, Since acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are produced, it is effective to use a blended base that captures the acid. On the other hand, amination halides Y ^1, in the case of using alkoxides of Y ^1, with the progress of the aromatic electrophilic substitution reaction, an amine, for the alcohol to produce, often use Bronsted base Although not necessary, the low desorption ability of aminos and alkoxys makes the use of Lewis acids, which promote their desorption, effective.

In addition, the polycyclic aromatic compound of the present invention and its multimer include a compound in which at least a part of hydrogen atoms are substituted with deuterium or cyano, or a compound in which at least a part of hydrogen atoms is substituted with halogen such as fluorine or chlorine. However, such a compound or the like can be synthesized in the same manner as described above by using a raw material in which the desired position is dehydrogenated, cyanated, fluorinated or chlorinated.

3. 3. Organic Devices The amino-substituted polycyclic aromatic compounds according to the present invention can be used as materials for organic devices. Examples of the organic device include an organic electroluminescent device, an organic field effect transistor, and an organic thin film solar cell.

3-1. Organic electroluminescent device The organic EL device according to this embodiment will be described in detail below with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing an organic EL device according to the present embodiment.

<Structure of organic electroluminescent device>
The organic EL element 100 shown in FIG. 1 is placed on a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer 103. The hole transport layer 104 is provided, the light emitting layer 105 is provided on the hole transport layer 104, the electron transport layer 106 is provided on the light emitting layer 105, and the electron transport layer 106 is provided. It has an electron injection layer 107 and a cathode 108 provided on the electron injection layer 107.

The organic EL element 100 is manufactured in the reverse order, for example, the substrate 101, the cathode 108 provided on the substrate 101, the electron injection layer 107 provided on the cathode 108, and the electron injection layer 107. Above the electron transport layer 106 provided on the electron transport layer 106, the light emitting layer 105 provided on the electron transport layer 106, the hole transport layer 104 provided on the light emitting layer 105, and the hole transport layer 104. The hole injection layer 103 provided in the hole injection layer 103 and the anode 102 provided on the hole injection layer 103 may be provided.

Not all of the above layers are required, and the minimum structural unit is composed of the anode 102, the light emitting layer 105, and the cathode 108, and the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection. The layer 107 is an arbitrarily provided layer. Further, each of the above layers may be composed of a single layer or a plurality of layers.

As the mode of the layer constituting the organic EL element, in addition to the above-mentioned "board / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode", " Substrate / anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / Anosome / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode "," substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode "," substrate / "Anofect / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light emitting layer / electron Transport layer / cathode ”,“ substrate / anode / hole injection layer / light emitting layer / electron injection layer / cathode ”,“ substrate / anode / hole injection layer / light emitting layer / electron transport layer / cathode ”,“ substrate / anode The configuration may be "/ light emitting layer / electron transport layer / cathode" or "substrate / anode / light emitting layer / electron injection layer / cathode".

<Substrate in organic electroluminescent device>
The substrate 101 is a support for the organic EL element 100, and usually quartz, glass, metal, plastic, or the like is used. The substrate 101 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Of these, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable. As for the glass substrate, soda lime glass, non-alkali glass, or the like is used, and the thickness may be sufficient to maintain the mechanical strength. Therefore, for example, 0.2 mm or more may be used. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, non-alkali glass is preferable because it is better that there are few elution ions from the glass, but soda lime glass with a barrier coat such as SiO ₂ is also commercially available, so it is possible to use this. it can. Further, in order to enhance the gas barrier property, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side, and a synthetic resin plate, film or sheet having a particularly low gas barrier property may be used as the substrate 101. When used, it is preferable to provide a gas barrier film.

<Anode in organic electroluminescent device>
The anode 102 serves to inject holes into the light emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these. ..

Examples of the material forming the anode 102 include inorganic compounds and organic compounds. Examples of the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxidation, etc.). (IZO, etc.), metals halide (copper iodide, etc.), copper sulfide, carbon black, ITO glass, nesa glass, etc. Examples of the organic compound include polythiophene such as poly (3-methylthiophene) and conductive polymers such as polypyrrole and polyaniline. In addition, it can be appropriately selected and used from the substances used as the anode of the organic EL element.

The resistance of the transparent electrode is not limited as long as a sufficient current can be supplied to emit light from the light emitting element, but it is desirable that the resistance is low from the viewpoint of power consumption of the light emitting element. For example, an ITO substrate of 300 Ω / □ or less functions as an element electrode, but since it is now possible to supply a substrate of about 10 Ω / □, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω. It is especially desirable to use a low resistance product of / □. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 50 to 300 nm.

<Hole injection layer and hole transport layer in organic electroluminescent devices>
The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are formed by laminating and mixing one or more of the hole injection / transport materials or a mixture of the hole injection / transport material and the polymer binder, respectively. Will be done. Further, an inorganic salt such as iron (III) chloride may be added to the hole injection / transport material to form a layer.

As a hole injection / transport material, it is necessary to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied, and the hole injection efficiency is high, and the injected holes are efficiently transported. Is desirable. For that purpose, it is preferable that the substance has a small ionization potential, a large hole mobility, excellent stability, and is less likely to generate trap impurities during production and use.

As the material for forming the hole injection layer 103 and the hole transport layer 104, in the photoconductive material, a compound conventionally used as a hole charge transport material, a p-type semiconductor, and a hole injection layer of an organic EL element. And any compound can be selected and used from the known compounds used in the hole transport layer. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis (N-arylcarbazole) or bis (N-alkylcarbazole), and triarylamine derivatives (aromatic tertiary). Polymers with amino in the main or side chains, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4 , 4'-diaminobiphenyl, N, N'-diphenyl-N, N'-dinaphthyl-4,4'-diaminobiphenyl, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4 , 4'-diphenyl-1,1'-diamine, N, N'-dinaphthyl -N, ^{N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N} 4, N ^{4 '-} diphenyl - N ^{^4,} N ⁴ ^'- bis (9-phenyl -9H- carbazol-3-yl) - [1,1'-biphenyl] ^{^{-4,4'-diamine, N 4, N 4, N}} 4', N 4 ^' -Tetra [1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] -4,4'-diamine, 4,4', 4 "-tris (3-methylphenyl (phenyl) Amino) triphenylamine, N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazole-3-yl) phenyl)- 9H-fluoren-2-amine, N, N-bis (4- (dibenzo [b, d] furan-4-yl) phenyl)-[1,1': 4', 1 "-terphenyl] -4- Triphenylamine derivatives such as amines, starburstamine derivatives, etc.), stillben derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives ( For example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile), heterocyclic compounds such as porphyrin derivatives, polysilane and the like. In the polymer system, polycarbonate or styrene derivative having the monomer in the side chain, polyvinylcarbazole, polysilane, etc. are preferable, but a thin film necessary for producing a light emitting element can be formed, holes can be injected from the anode, and holes can be further injected. There is no particular limitation as long as it is a compound capable of transporting.

It is also known that the conductivity of organic semiconductors is strongly affected by doping. The organic semiconductor matrix substance is composed of a compound having a good electron donating property or a compound having a good electron accepting property. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping electron donors. (For example, reference "M.Pfeiffer, A.Beyer, T.Fritz, K.Leo, Appl.Phys.Lett., 73 (22), 3202-3204 (1998)" and reference "J. Blochwitz, M." .Pfeiffer, T.Fritz, K.Leo, Appl.Phys.Lett., 73 (6), 729-731 (1998) "). They generate so-called holes by an electron transfer process in an electron-donating base material (hole-transporting material). Depending on the number of holes and the mobility, the conductivity of the base material changes considerably. As the matrix material having hole transporting properties, for example, a benzidine derivative (TPD or the like) or a starburst amine derivative (TDATA or the like), or a specific metal phthalocyanine (particularly, zinc phthalocyanine (ZnPc) or the like) is known (such as zinc phthalocyanine). JP-A-2005-167175).

The above-mentioned materials for the hole injection layer and the material for the hole transport layer are polymer compounds obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer, or a polymer crosslinked product thereof, or a polymer crosslinked product thereof. A pendant type polymer compound obtained by reacting a main chain type polymer with the above-mentioned reactive compound, or a pendant type polymer crosslinked product thereof can also be used as a material for a hole layer. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the formula (1) can be cited.
Details of the uses of such polymer compounds and crosslinked polymers will be described later.

<Light emitting layer in organic electroluminescent device>
The light emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between the electrodes to which an electric field is applied. The material for forming the light emitting layer 105 may be a compound (light emitting compound) that is excited by recombination of holes and electrons to emit light, and can form a stable thin film shape and is in a solid state. It is preferable that the compound exhibits a strong emission (fluorescence) efficiency. In the present invention, as the material for the light emitting layer, a host material and, for example, a polycyclic aromatic compound represented by the formula (1) as a dopant material can be used.

The light emitting layer may be either a single layer or a plurality of layers, and each is formed of a light emitting layer material (host material, dopant material). The host material and the dopant material may be one kind or a combination of two or more. The dopant material may be included entirely, partially, or partially in the host material. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be mixed with the host material in advance and then vapor-deposited at the same time.

The amount of host material used differs depending on the type of host material, and may be determined according to the characteristics of the host material. The guideline for the amount of the host material used is preferably 50 to 99.99% by mass, more preferably 80 to 99.95% by mass, and further preferably 90 to 99.9% by mass of the entire material for the light emitting layer. Is.

The amount of the dopant material used differs depending on the type of the dopant material, and may be determined according to the characteristics of the dopant material. The guideline for the amount of the dopant used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and further preferably 0.1 to 10% by mass of the entire light emitting layer material. is there. The above range is preferable in that, for example, the density quenching phenomenon can be prevented. From the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms of the dopant material are deuterated.

Host materials include fused ring derivatives such as anthracene, pyrene, dibenzoglycene or fluorene, which have long been known as luminescent materials, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives. , Examples of compounds represented by any of the following formulas (H1), (H2) and (H3). Anthracene compounds, fluorene compounds or dibenzochrysene compounds, compounds represented by any of the following formulas (H1), (H2) and (H3) are preferable, and anthracene compounds or formulas (H1) and (H2) below And the compound represented by any of (H3) is more preferable. Further, from the viewpoint of durability, it is also preferable that a part or all of the hydrogen atoms of the host material are deuterated. Further, a host compound in which some or all deuterated hydrogen atoms are deuterated and a dopant compound in which some or all deuterated hydrogen atoms are deuterated are combined to form a light emitting layer. It is also preferable to do so.

The formula (H1), (H2) and (H3) in, ^{L 1} is an arylene having 6 to 24 carbon atoms, heteroarylene having 2 to 24 carbon atoms, heteroarylene arylene and 6 to 24 carbon atoms having 6 to 24 carbon atoms The arylene is a heteroarylene arylene, preferably an arylene having 6 to 16 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms, and particularly preferably an arylene having 6 to 10 carbon atoms, specifically, a benzene ring or a biphenyl ring. , Divalent groups such as terphenyl ring and fluorene ring. As the heteroarylene, a heteroarylene having 2 to 24 carbon atoms is preferable, a heteroarylene having 2 to 20 carbon atoms is more preferable, a heteroarylene having 2 to 15 carbon atoms is further preferable, and a heteroarylene having 2 to 10 carbon atoms is particularly preferable. Preferably, specifically, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxazole ring, a thiazazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, Pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, synnoline ring, quinazoline ring , Kinoxalin ring, phthalazine ring, naphthylidine ring, purine ring, pteridine ring, carbazole ring, aclysin ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolidin ring, furan ring, benzofuran ring, isobenzofuran ring , Dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, frazane ring, oxazole ring, thiantolene ring and other divalent groups.
At least one hydrogen in the compound represented by each of the above formulas may be substituted with alkyl, cyano, halogen or deuterium having 1 to 6 carbon atoms.

A preferable specific example is a compound represented by any of the structural formulas listed below. In the following structural formula, Me is methyl. In the structural formulas listed below, at least one hydrogen may be substituted with halogen, cyano, alkyl having 1 to 4 carbon atoms (for example, methyl or t-butyl), phenyl or naphthyl.

<Anthracene compounds>
The anthracene-based compound as a host is, for example, a compound represented by the following formula (3-H) or the following formula (3-2-H).

In equation (3-H),
X and Ar ⁴ are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, respectively. Aryl heteroarylamino which may be substituted, alkyl which may be substituted, cycloalkyl which may be substituted, alkenyl which may be substituted, alkoxy which may be substituted, which may be substituted. Aryloxy, optionally substituted arylthio or optionally substituted silyl, all X and Ar ⁴ are not hydrogenated at the same time.
At least one hydrogen in the compound represented by the formula (3-H) may be substituted with a halogen, cyano, deuterium or a heteroaryl which may be substituted.

Further, a multimer (preferably a dimer) may be formed by using the structure represented by the formula (3-H) as a unit structure. In this case, for example, the unit structures represented by the formula (3-H) may be bonded to each other via X, and the X includes a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.) and a heteroarylene (pyridine). A group in which a ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, a phenyl-substituted carbazole ring, etc. have a divalent bond value) and the like can be mentioned.

Details of the above aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl will be described in the section of preferred embodiments below. Examples of the substituents thereof include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl, and these. Details will also be described in the section of preferred embodiments below.

Preferred embodiments of the anthracene-based compound will be described below. The definition of the code in the structure below is the same as the definition described above.

In the formula (3-H), X is a group independently represented by the formula (3-X1), the formula (3-X2) or the formula (3-X3), and the formula (3-X1) and the formula (3-X1). The group represented by (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3-H) in *. Preferably, the two Xs do not simultaneously become groups represented by the formula (3-X3). More preferably, the two Xs do not simultaneously become a group represented by the formula (3-X2).

The naphthalene moiety in the formulas (3-X1) and (3-X2) may be condensed with one benzene ring. The structure condensed in this way is as follows.

Ar ¹ and Ar ² are independently represented by hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or formula (A). Groups to be (including carbazolyl, benzocarbazolyl and phenyl-substituted carbazolyl). When Ar ¹ or Ar ² is a group represented by the formula (A) described later, the group represented by the formula (A) is represented by the formula (3-X1) or the formula (3-X2) in the *. It binds to the naphthalene ring inside.

Ar ³ is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the formula (A) (carbazolyl, benzocarbazolyl). And phenyl-substituted carbazolyl). When Ar ³ is a group represented by the formula (A), the group represented by the formula (A) is bonded to the single bond represented by the straight line in the formula (3-X3) in the *. .. That is, the anthracene ring of the formula (3-H) and the group represented by the formula (A) are directly bonded.

Further, Ar ³ may have a substituent, and at least one hydrogen in Ar ³ is further an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl and phenanthryl. , Fluolenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the formula (A) (including carbazolyl and phenyl-substituted carbazolyl) may be substituted. When the substituent contained in Ar ³ is a group represented by the formula (A), the group represented by the formula (A) is bonded to Ar ³ in the formula (3-X3) in the *.

Ar ⁴ is independently substituted with hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or alkyl having 1 to 4 carbon atoms (methyl, ethyl, t-butyl, etc.) and / or cycloalkyl having 5 to 10 carbon atoms. Cyril has been.

Examples of alkyl having 1 to 4 carbon atoms to be substituted with silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, cyclobutyl, etc., and the three hydrogens in silyl are independent of each other. , Substituted with these alkyls.

Specific "silyl substituted with alkyl having 1 to 4 carbon atoms" includes trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyl. Dimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyl Diethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldii-propylsilyl, ethyldii-propylsilyl, Examples thereof include butyl di-propyl silyl, sec-butyl di-propyl silyl and t-butyl di-propyl silyl.

Cycloalkyls having 5 to 10 carbon atoms to be substituted with silyl are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo [1.1.1] pentyl, bicyclo [2.0.1] pentyl, Bicyclo [1.2.1] hexyl, bicyclo [3.0.1] hexyl, bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, decahydronaphthalenyl, decahydro Azulenyl and the like are mentioned, and each of the three hydrogens in silyl is independently substituted with these cycloalkyls.

Specific examples of the "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentyl silyl and tricyclohexyl silyl.

Substituted silyls include dialkylcycloalkylsilyls substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyls substituted with one alkyl and two cycloalkyls, which are substituted alkyls and cycloalkyls. As a specific example of, the above-mentioned group can be mentioned.

Further, hydrogen in the chemical structure of the anthracene compound represented by the formula (3-H) may be substituted with the group represented by the formula (A). When substituted with a group represented by the formula (A), the group represented by the formula (A) is substituted with at least one hydrogen in the compound represented by the formula (3-H) in the *.

The group represented by the formula (A) is one of the substituents that the anthracene-based compound represented by the formula (3-H) can have.

In formula (A), Y is —O—, —S— or> N—R ²⁹ , and R ²¹ to R ²⁸ are independently hydrogen, optionally substituted alkyl, optionally substituted, respectively. Cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tri Cycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, the adjacent groups of R ²¹ to R ²⁸ are bonded to each other to form a hydrocarbon ring. It may form an aryl ring or a heteroaryl ring, and R ²⁹ is an aryl that may be hydrogen or substituted.

The "alkyl" of the "optionally substituted alkyl" in R ²¹ to R ²⁸ may be either a straight chain or a branched chain, for example, a linear alkyl having 1 to 24 carbon atoms or a linear alkyl having 3 to 24 carbon atoms. Branched chain alkyl can be mentioned. An alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and an alkyl having 1 to 6 carbon atoms is more preferable. (Branched chain alkyl having 3 to 6 carbon atoms) is more preferable, and alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is particularly preferable.

Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 -Methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2 -Propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, Examples thereof include n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicocil.

The "cycloalkyl" of the "optionally substituted cycloalkyl" in R ²¹ to R ²⁸ includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, and cycloalkyl having 3 to 16 carbon atoms. , Cycloalkyl having 3 to 14 carbon atoms, Cycloalkyl having 5 to 10 carbon atoms, Cycloalkyl having 5 to 8 carbon atoms, Cycloalkyl having 5 to 6 carbon atoms, Cycloalkyl having 5 carbon atoms and the like.

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, alkyl (particularly methyl) substituents having 1 to 4 carbon atoms, norbornenyl, and bicyclo. [1.0.1] Butyl, Bicyclo [1.1.1] Pentyl, Bicyclo [2.0.1] Pentyl, Bicyclo [1.2.1] Hexyl, Bicyclo [3.0.1] Hexil, Bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like can be mentioned.

Examples of the "aryl" of the "optionally substituted aryl" in R ²¹ to R ²⁸ include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 16 carbon atoms, and 6 to 12 carbon atoms. Aryl is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable.

Specific examples of "aryl" include phenyl, which is a monocyclic system, biphenylyl, which is a bicyclic system, naphthyl, which is a condensed bicyclic system, and terfenylyl, which is a tricyclic system (m-terphenylyl, o-terphenylyl, p-terphenylyl). , Condensed tricyclics such as acenaphthylenyl, fluorenyl, phenylenyl, phenylentrenyl, condensed tetracyclics triphenylenyl, pyrenyl, naphthalenyl, condensed pentacyclics perylenyl, pentasenyl and the like.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" in R ²¹ to R ²⁸ include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and carbon. Heteroaryls of number 2 to 20 are more preferred, heteroaryls of 2 to 15 carbon atoms are even more preferred, and heteroaryls of 2 to 10 carbon atoms are particularly preferred. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific "heteroaryl" includes, for example, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-. Indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, synnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenoxadinyl. Examples thereof include phenazinyl, indridinyl, frill, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo [b] thienyl, dibenzothienyl, frazanyl, oxadiazolyl, thiantranyl, naphthobenzofuranyl and naphthobenzothienyl.

Examples of the “alkoxy” of the “optionally substituted alkoxy” in R ²¹ to R ²⁸ include a straight-chain alkoxy having 1 to 24 carbon atoms or a branched chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (alkoxy of branched chains having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbon atoms (alkoxy of branched chains having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms is more preferable. Alkoxy (alkoxy of branched chains having 3 to 6 carbon atoms) is more preferable, and alkoxy having 1 to 4 carbon atoms (alkoxy of branched chains having 3 to 4 carbon atoms) is particularly preferable.

Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.

The "aryloxy" of the "optionally substituted aryloxy" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -OH group is substituted with an aryl, and this aryl is used in R ²¹ to R ²⁸ described above. The group described as "aryl" can be cited.

The "arylthio" of the "optionally substituted arylthio" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -SH group is substituted with an aryl, and this aryl is the "aryl" in R ²¹ to R ²⁸ described above. Can be quoted as the group described as.

Examples of the "trialkylsilyl" in R ²¹ to R ²⁸ include groups in which the three hydrogens in the silyl group are independently substituted with alkyl, and this alkyl is referred to as the "alkyl" in R ²¹ to R ²⁸ described above. The groups described can be quoted. Preferred alkyls for substitution are alkyls having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl and cyclobutyl.

Specific "trialkylsilyl" includes trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyl. Dimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyl Dipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldii-propylsilyl, ethyldii-propylsilyl, butyldii-propylsilyl, sec-butyldii -Propylsilyl, t-butyldii-propylsilyl and the like can be mentioned.

Examples of the "tricycloalkylsilyl" in R ²¹ to R ²⁸ include groups in which the three hydrogens in the silyl group are independently substituted with cycloalkyl, and this cycloalkyl is the above-mentioned "tricycloalkylsilyl" in R ²¹ to R ²⁸ . The group described as "cycloalkyl" can be cited. Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo [1.1.1] pentyl, bicyclo [. 2.0.1] Pentyl, bicyclo [1.2.1] hexyl, bicyclo [3.0.1] hexyl, bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, Examples thereof include decahydronaphthalenyl and decahydroazurenyl.

Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

Examples of the "substituted amino" of the "optionally substituted amino" in R ²¹ to R ²⁸ include aminos in which two hydrogens are substituted with aryl or heteroaryl. Amino in which two hydrogens are substituted with aryl is a diaryl substituted amino, amino in which two hydrogens are substituted with heteroaryl is a diheteroaryl substituted amino, and amino in which two hydrogens are substituted with aryl and heteroaryl. Is an aryl heteroaryl substituted amino. As the aryl or heteroaryl, the groups described as "aryl" or "heteroaryl" in R ²¹ to R ²⁸ described above can be cited.

Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, and naphthylpyridylamino.

Examples of the "halogen" in R ²¹ to R ²⁸ include fluorine, chlorine, bromine and iodine.

Among the groups described as R ²¹ to R ²⁸ , some may be substituted as described above, and examples of the substituent in this case include alkyl, cycloalkyl, aryl or heteroaryl. The alkyl, cycloalkyl, aryl or heteroaryl can be cited as the groups described above as "alkyl", "cycloalkyl", "aryl" or "heteroaryl" in R ²¹ -R ²⁸ .

R ²⁹ in the "> N-R ^29" as Y is hydrogen or aryl which may be substituted, be cited a group described as the "aryl" in R ^{21 ~} R ²⁸ described above as the aryl As the substituent, the group described as the substituent for R ²¹ to R ²⁸ can be cited.

Adjacent groups of R ²¹ to R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. The case where the ring is not formed is the group represented by the following formula (A-1), and the case where the ring is formed is, for example, the group represented by the following formulas (A-2) to (A-14). Be done. In addition, at least one hydrogen in the group represented by any of formulas (A-1) to (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl,. It may be substituted with tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl substituted amino, diheteroaryl substituted amino, aryl heteroaryl substituted amino, halogen, hydroxy or cyano.

Examples of the ring formed by bonding adjacent groups to each other include a cyclohexane ring in the case of a hydrocarbon ring, and "aryl" and "heteroaryl" in R ²¹ to R ²⁸ described above as an aryl ring and a heteroaryl ring. The ring structures described in the above are mentioned, and these rings are formed so as to condense with one or two benzene rings in the formula (A-1).

Examples of the group represented by the formula (A) include groups represented by any of the formulas (A-1) to (A-14), and the groups represented by the formulas (A-1) to (A-5). ) And the group represented by any of the formulas (A-12) to (A-14), and more preferably the group represented by any of the formulas (A-1) to (A-4). , The group represented by any of the formula (A-1), the formula (A-3) and the formula (A-4) is more preferable, and the group represented by the formula (A-1) is particularly preferable.

The group represented by the formula (A) is the naphthalene ring in the formula (3-X1) or the formula (3-X2), the single bond in the formula (3-X3), and the formula in * in the formula (A). As described above, it binds to Ar ³ in (3-X3) and replaces it with at least one hydrogen in the compound represented by the formula (3-H), but among these binding forms, the formula (3-X3) Preferably, the form is X1) or a naphthalene ring in the formula (3-X2), a single bond in the formula (3-X3) and / or a bond with Ar ³ in the formula (3-X3).

Further, in the structure of the group represented by the formula (A), the naphthalene ring in the formula (3-X1) or the formula (3-X2), the single bond in the formula (3-X3), and the formula (3-X3). ) Ar ³ is bonded position in, also in the structure of the group represented by the formula (a), and substitution position with at least one hydrogen in the compound represented by the formula (3-H) has the formula ( It may be at any position in the structure of A), for example, either of the two benzene rings in the structure of formula (A), or adjacent R ²¹ to R ^{28 in} the structure of formula (A). It can be bonded at any ring formed by bonding the groups to each other, or at any position in R ²⁹ at "> N-R ²⁹ " as Y in the structure of formula (A).

Examples of the group represented by the formula (A) include the following groups. Y and * in the formula have the same definition as above.

Further, the hydrogen in the chemical structure of the anthracene compound represented by the formula (3-H) may be deuterium in whole or in part.

Further, as the anthracene compound, an anthracene compound represented by the following formula (3-2-H) can be mentioned.

Wherein ^{(3-2-H), Ar c} ', Ar 14', and ^{Ar 15} 'are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl , Or a group represented by any of the above formulas (A-1) to (A-14), and at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzo. It may be substituted with fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any of formulas (A-1) to (A-14). Here, when the hydrogen of methylene in both fluorenyl and benzofluorenyl is substituted with phenyl, these phenyls may be bonded to each other in a single bond. ^{^{Further, Ar c ', Ar 14'}} , and Ar 15 ^'are the carbon atoms on the anthracene ring which is not bound methyl or t- butyl instead of hydrogen may be substituted. At least one hydrogen in the compound represented by the formula (3-2-H) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by the formula (3-2-H) may be substituted. It has been replaced with deuterium.

Wherein ^{(3-2-H), Ar c} ', Ar 14', and ^{Ar 15} 'each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl or above equation, (A-1) ~ formula ( It is preferably a group represented by any of A-4), and at least one hydrogen in these groups is phenyl, naphthyl, phenanthryl, fluorenyl, or formulas (A-1) to (A-4). It may be substituted with a group represented by any of.

In the compound represented by the formula (3-2-H), at least the hydrogen bonded to the carbon of 10-position of the anthracene ring (Ar c ^'is a carbon position 9 binding) is replaced by deuterium It is preferable to have. That is, the compound represented by the formula (3-2-H) is preferably a compound represented by the following formula (3-2-Hb). In the formula (1Ab), D is ^{^{deuterium, Ar c ', Ar 14'}} , and ^{Ar 15} 'are the same as defined in the formula (3-2-H). D in the formula ((3-2-Hb) indicates that at least this position is deuterium, and any one or more of the other hydrogens in the formula (3-2-Hb) are deuterium at the same time. It is also preferable that all the hydrogens in the formula (3-2-Hb) are deuterium.

Specific examples of the anthracene-based compound include compounds represented by the following formulas (3-1) to (3-72). In the following structural formula, "Me" indicates methyl, "D" indicates deuterium, and "tBu" indicates t-butyl.

In addition, as other specific examples of anthracene compounds, for example, compounds represented by the following formulas (3-131-Y) to (3-179-Y), the following formula (3-180-Y). ~ Compound represented by the formula (3-182-Y), the following formula (3-183-N), the following formula (3-184-Y) to the following formula (3-254-Y), the formula (3-254- Examples thereof include compounds represented by formulas (Y) to (3-269-Y) and the following formulas (3-500) to (3-557). Compounds represented by the following formulas (3-131-Y) to (3-179-Y), compounds represented by the following formulas (3-180-Y) to (3-182-Y), the following formulas. (3-183-N), the following formulas (3-184-Y) to (3-254-Y), formulas (3-254-Y) to formulas (3-269-Y), and the following formulas (3). In −500) to formula (3-557), the hydrogen atom may be partially or wholly substituted with deuterium. Y in the equation is -O-, -S-,> N-R ²⁹ (R ²⁹ has the same definition as above) or> C (-R ³⁰ ) ₂ (R ³⁰ may be concatenated aryl or alkyl ), Where R ²⁹ is, for example, phenyl and R ³⁰ is, for example, methyl. For example, when Y is O, the formula (3-131-Y) is the formula (3-131-O), and when Y is -S- or> N-R ²⁹ , the formula (3-131-Y) is used. 131-S) or formula (3-131-N).

Among these compounds, formulas (3-131-Y) to formulas (3-134-Y), formulas (3-138-Y), formulas (3-140-Y) to formulas (3-143-Y). , Equation (3-150-Y), Equation (3-153-Y) to Equation (3-156-Y), Equation (3-166-Y), Equation (3-168-Y), Equation (3-168-Y) 173-Y), formula (3-177-Y), formula (3-180-Y) to formula (3-183-N), formula (3-185-Y), formula (3-190-Y), Formula (3-223-Y), Formula (3-241-Y), Formula (3-250-Y), Formula (3-252-Y) to Formula (3-254-Y), Formula (3-501) ), Equation (3-507), Equation (3-508), Equation (3-509), Equation (3-513), Equation (3-514), Equation (3-518), Equation (3-521). , Formulas (3-538) to (3-547) or formulas (3-600) to (3-620) are preferred. Further, Y is preferably —O—.

The anthracene-based compound represented by the formula (3-H) has a compound having a reactive group at a desired position in the anthracene skeleton and a reactive group in a partial structure such as the structure of X, Ar ⁴ and the formula (A). It can be produced by applying Suzuki coupling, Negishi coupling, or other known coupling reactions using the compound as a starting material. Examples of the reactive group of these reactive compounds include halogen and boronic acid. As a specific production method, for example, the synthesis method in paragraphs [089] to [0175] of International Publication No. 2014/141725 can be referred to.
The anthracene-based compound represented by the formula (3-2-H) is a production method described in International Publication No. 2006/003842, Korean Publication No. 2017-116885, International Publication No. 2009/142230, and the like. It can be manufactured by a method according to the above.

<Fluorene compounds>
The compound represented by the formula (4-H) basically functions as a host.

In formula (4-H),
R ¹ to R ¹⁰ are independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in the formula (4-H) via a linking group), diarylamino, and diarylamino. Heteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one of which may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
In addition, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ or R ⁹ and R ¹⁰ are independently combined. It may form a fused ring or a spiro ring, and at least one hydrogen in the formed ring may be aryl or heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group). ), Diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, in which at least one hydrogen is aryl, heteroaryl, alkyl or cycloalkyl. May be replaced with
At least one hydrogen in the compound represented by the formula (4-H) may be substituted with halogen, cyano or deuterium.

For the details of each group in the definition of the formula (4-H), the above-mentioned description of the polycyclic aromatic compound of the formula (1) can be cited.

Examples of the alkenyl in R ¹ to R ¹⁰ include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, and having 2 to 6 carbon atoms. Alkenyl is more preferable, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

As a specific example of the heteroaryl, any one from the compounds of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4) or formula (4-Ar5) A monovalent group represented by excluding one hydrogen atom can also be mentioned.

Wherein (4-Ar5) from equation (4-Ar1), ^{Y 1} are each independently, O, S or N-R, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen,
At least one hydrogen in the structures of formulas (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

These heteroaryls may be attached to the fluorene skeleton in formula (4-H) via a linking group. That is, not only the fluorene skeleton in the formula (4-H) and the heteroaryl may be directly bonded, but also they may be bonded via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, and -OCH ₂ CH ₂ O-.

In addition, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ or R ⁷ and R ⁸ in the equation (4-H) are independent of each other. They may be bonded to form a fused ring, and R ⁹ and R ¹⁰ may be bonded to form a spiro ring. The condensed ring formed by R ¹ to R ⁸ is a ring that condenses with the benzene ring in the formula (4-H), and is an aliphatic ring or an aromatic ring. It is preferably an aromatic ring, and examples of the structure including the benzene ring in the formula (4-H) include a naphthalene ring and a phenanthrene ring. The spiro ring formed by R ⁹ and R ¹⁰ is a ring spiro-bonded to the 5-membered ring in the formula (4-H), and is an aliphatic ring or an aromatic ring. It is preferably an aromatic ring, and examples thereof include a fluorene ring.

The compound represented by the formula (4-H) is preferably a compound represented by the following formula (4-H-1), formula (4-H-2) or formula (4-H-3). , A compound formed by condensing a benzene ring formed by combining R ¹ and R ^{2 in} the formula (4-H), and a benzene ring formed by combining R ³ and R ⁴ in the formula (4-H), respectively. There compounds condensed, a compound either is not bound to R ¹ ^to R ⁸ in the formula (4-H).

Equation (4-H-1), the definition of ^{R 10} from ^{R 1} in the formula (4-H-2) and formula (4-H-3) and ^{R 10} from ^{R 1} corresponding in formula (4-H) It is the same, and the definitions of R ¹¹ to R ^{14 in} the formulas (4-H-1) and (4-H-2) are the same as those of R ¹ to R ¹⁰ in the formula (4-H).

The compound represented by the formula (4-H) is more preferably a compound represented by the following formula (4-H-1A), formula (4-H-2A) or formula (4-H-3A). Yes, they are compounds in which R ⁹ and R ¹⁰ are combined to form a spiro-fluorene ring in the formula (4-H-1), formula (4-H-1) or formula (4-H-3), respectively. is there.

The definitions of R ² to R ^{7 in} the formula (4-1A), the formula (4-2A) and the formula (4-3A) are in the formula (4-1), the formula (4-2) and the formula (4-3). corresponding the same from ^{R 2} and ^{R 7,} ^R in the formula also defined formula (4-1) of the ^{R 14} from ^{R 11} in (4-1A) and (4-2A) and (4-2) ¹¹ from is the same as ^{R 14.}

Further, the hydrogen in the compound represented by the formula (4-H) may be entirely or partially substituted with halogen, cyano or deuterium.

A more specific example of the fluorene compound as the host of the present invention is a compound represented by the following structural formula. In addition, "Me" indicates methyl.

<Dibenzochrysene compounds>
The dibenzochysene compound as a host is, for example, a compound represented by the following formula (5-H).

In formula (5-H),
R ¹ to R ¹⁶ are independent of hydrogen, aryl, heteroaryl (the heteroaryl may be attached to the dibenzocrysen skeleton in formula (5-H) via a linking group), diarylamino, Diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one of which may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Further, adjacent groups of R ¹ to R ¹⁶ may be bonded to each other to form a fused ring, and at least one hydrogen in the formed ring is aryl or heteroaryl (the heteroaryl is via a linking group). It may be attached to the formed ring), and may be substituted with diallylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least in these. One hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
At least one hydrogen in the compound represented by the formula (5-H) may be substituted with halogen, cyano or deuterium.

For the details of each group in the definition of the formula (5-H), the above-mentioned description of the polycyclic aromatic compound of the formula (1) can be cited.

Examples of the alkenyl in the definition of the formula (5-H) include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, and having 2 carbon atoms. An alkenyl of to 6 is more preferable, and an alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

As a specific example of the heteroaryl, any one from the compounds of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) A monovalent group represented by excluding one hydrogen atom can also be mentioned.

Wherein (5-Ar5) from equation (5-Ar1), ^{Y 1} are each independently, O, S or N-R, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen,
At least one hydrogen in the structures of formulas (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

These heteroaryls may be attached to the dibenzochrysene skeleton in formula (5-H) via a linking group. That is, not only the dibenzochrysene skeleton in the formula (5-H) and the heteroaryl may be directly bonded, but also they may be bonded via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, and -OCH ₂ CH ₂ O-.

The compound represented by the formula (5-H) is preferably R ¹ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , R ¹² , R ¹³ and R ¹⁶ are hydrogen. In this case, ^R ^2, R ³ in the formula ^{(5-H), R 6} , R 7, R 10, R 11, R 14 and ^{R 15} are each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl , Phenanthrenyl, formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or monovalent group having the structure of formula (5-Ar5) (having the structure) The monovalent group is via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O- via formula (5-). It may be bound to the dibenzoglycene skeleton in H)), preferably methyl, ethyl, propyl, or butyl.

The compound represented by the formula (5-H) is more ^{^{^{^{preferably, R 1, R 2, R}}}} 4, R 5, R 7, R 8, R 9, R 10, R 12, R 13, R 15 and R ¹⁶ is hydrogen. In this case, at least one (preferably one or two, more preferably one) of R ³ , R ⁶ , R ¹¹ and R ¹⁴ in formula (5-H) is a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, _{_{_{ethylene, -OCH 2 CH 2 -, -}}} CH 2 CH 2 O-, _or, via a -OCH 2 _CH 2 O-, the formula (5-Ar @ 1), the formula (5-Ar2), A monovalent group having a structure of formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5).
Other than the at least one (that is, other than the position where the monovalent group having the structure is substituted) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one of these. Hydrogen may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

Moreover, Table formula as (5-H) ^R 2 ^{^{^{^{in, R 3, R 6, R}}}} 7, R 10, R 11, R 14 and ^{R 15,} the formula (5-Ar1) from equation (5-Ar5) When a monovalent group having the structure to be used is selected, at least one hydrogen in the structure is bonded to any of R ¹ to R ^{16 in} the formula (5-H) to form a single bond. You may.

A more specific example of the dibenzochrysene compound as the host of the present invention is a compound represented by the following structural formula. In addition, "tBu" indicates t-butyl.

The above-mentioned materials for the light emitting layer (host material and dopant material) are polymer compounds obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer, or a polymer crosslinked product thereof, or a main chain. A pendant type polymer compound obtained by reacting a type polymer with the above-mentioned reactive compound, or a pendant type polymer crosslinked product thereof can also be used as a material for a light emitting layer. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the formula (1) can be cited.
Details of the uses of such polymer compounds and crosslinked polymers will be described later.

In equation (SPH-1)
MU is an independent divalent aromatic group, EC is an independent monovalent aromatic group, two hydrogens in MU are replaced with EC or MU, and k is an integer of 2 to 50,000. is there.

More specifically
The MUs are arylene, heteroarylene, dialylene arylamino, dialylene arylboryl, oxaborin-diyl, and azaborin-diyl, respectively.
ECs are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy.
At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl and cycloalkyl.
k is an integer from 2 to 50,000.
k is preferably an integer of 20,000 to 50,000, and more preferably an integer of 100 to 50,000.

At least one hydrogen in MU and EC in the formula (SPH-1) may be substituted with an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, a halogen or deuterium, and further described above. arbitrary -CH ₂ in the alkyl - is -O- or -Si _(CH _{3) 2} - may be substituted with the formula in the alkyl (SPH-1) -CH connected directly to the EC of ₂ - Any —CH ₂ − except for may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine.

Examples of the MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds.

More specifically, a divalent group represented by any of the following structures can be mentioned. In these, the MU binds to another MU or EC at *.

Further, as the EC, for example, a monovalent group represented by any of the following structures can be mentioned. In these, EC binds to MU at *.

In the compound represented by the formula (SPH-1), from the viewpoint of solubility and coating film forming property, 10 to 100% of the total number of MUs (k) in the molecule has an alkyl having 1 to 24 carbon atoms. It is more preferable that 30 to 100% of the total number of MUs (k) in the molecule has an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and the total number of MUs in the molecule ( It is more preferable that 50 to 100% of MU of k) has an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule has an alkyl having 7 to 24 carbon atoms, and the total number of MUs in the molecule (k). ), It is more preferable that 30 to 100% of the MU has an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

Details of the uses of such polymer compounds and crosslinked polymers will be described later.

<Electron injection layer and electron transport layer in organic electroluminescent device>
The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting the electrons injected from the cathode 108 or the electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are formed by laminating and mixing one or more of the electron transport / injection materials or a mixture of the electron transport / injection material and the polymer binder, respectively.

The electron injection / transport layer is a layer in which electrons are injected from the cathode and is in charge of further transporting electrons. It is desirable that the electron injection efficiency is high and the injected electrons are efficiently transported. For that purpose, it is preferable that the substance has a high electron affinity, a high electron mobility, excellent stability, and is less likely to generate trap impurities during production and use. However, when considering the transport balance between holes and electrons, the electron transport capacity is so high when it mainly plays a role of efficiently blocking the holes from the anode from flowing to the cathode side without recombination. Even if it is not high, it has the same effect of improving luminous efficiency as a material having high electron transport capacity. Therefore, the electron injection / transport layer in the present embodiment may also include the function of a layer capable of efficiently blocking the movement of holes.

As the material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107, it is used for a compound conventionally used as an electron transfer compound in a photoconducting material, an electron injection layer and an electron transport layer of an organic EL element. It can be arbitrarily selected and used from the known compounds known.

The material used for the electron transport layer or the electron injection layer is a compound composed of an aromatic ring or a complex aromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus. It preferably contains at least one selected from a pyrrole derivative, a condensed ring derivative thereof, and a metal complex having an electron-accepting nitrogen. Specifically, fused ring-based aromatic ring derivatives such as naphthalene and anthracene, styryl-based aromatic ring derivatives typified by 4,4'-bis (diphenylethenyl) biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives. , Quinone derivatives such as anthraquinone and diphenoquinone, phosphoroxide derivatives, arylnitrile derivatives and indole derivatives. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complex, azomethine complex, tropolone metal complex, flavonol metal complex and benzoquinoline metal complex. These materials may be used alone, but may be mixed with different materials.

Specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, and perylene derivatives. , Oxaziazole derivatives (1,3-bis [(4-t-butylphenyl) 1,3,4-oxadiazolyl] phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1, etc.) 3,4-Triazole, etc.), thiazazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxalin derivatives, quinoxalin derivative polymers, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorophenylene derivatives, triazine derivatives, pyrazines Derivatives, benzoquinolin derivatives (2,2'-bis (benzo [h] quinoline-2-yl) -9,9'-spirobifluorene, etc.), imidazole pyridine derivatives, borane derivatives, benzoimidazole derivatives (tris (N-) Phenylbenzoimidazole-2-yl) benzene, etc.), benzoxazole derivative, benzothiazole derivative, quinoline derivative, oligopyridine derivative such as terpyridine, bipyridine derivative, telpyridine derivative (1,3-bis (4'-(2,2') : 6'2 "-terpyridinyl)) benzene, etc.), naphthylidine derivatives (bis (1-naphthyl) -4- (1,8-naphthylidine-2-yl) phenylphosphine oxide, etc.), aldazine derivatives, arylnitrile derivatives, indols, etc. Derivatives, phosphine oxide derivatives, bisstyryl derivatives and the like can be mentioned.

Further, a metal complex having electron-accepting nitrogen can also be used. For example, hydroxyazole complexes such as quinolinol-based metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes can be used. can give.

The above-mentioned materials can be used alone, but they may be mixed with different materials.

Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, and quinolinol derivatives Metal derivatives are preferred.

<Borane derivative>
The borane derivative is, for example, a compound represented by the following formula (ETM-1), and is disclosed in detail in JP-A-2007-27587.

In formula (ETM-1), R ¹¹ and R ¹² are independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, respectively. At least one of the rings, or cyanos, R ¹³ to R ¹⁶ are independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, respectively. , X are optionally substituted arylene, Y is optionally substituted aryl having 16 or less carbon atoms, substituted boron, or optionally substituted carbazolyl, and n. Are independently integers from 0 to 3. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

Among the compounds represented by the formula (ETM-1), the compound represented by the following formula (ETM-1-1) and the compound represented by the following formula (ETM-1-2) are preferable.

In formula (ETM-1-1), R ¹¹ and R ¹² are independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen, respectively. At least one of the containing heterocycles, or cyano, R ¹³ to R ¹⁶ are independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, respectively. R ²¹ and R ²² are independently of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano. At least one, X ¹ is an arylene having 20 or less carbon atoms which may be substituted, n is an integer of 0 to 3 independently, and m is 0 to 4 independently. Is an integer of. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

In formula (ETM-1-2), R ¹¹ and R ¹² are independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen, respectively. At least one of the containing heterocycles, or cyano, R ¹³ to R ¹⁶ are independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, respectively. X ¹ is an arylene having 20 or less carbon atoms which may be substituted, and n is an integer of 0 to 3 independently. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

Specific examples of X ¹ include divalent groups represented by any of the following formulas (X-1) to (X-9).

(In each formula, ^Ra is an independently alkyl, cycloalkyl or optionally substituted phenyl, and * represents the bond position.)

Specific examples of this borane derivative include the following compounds.

This borane derivative can be produced by using a known raw material and a known synthesis method.

<Pyridine derivative>
The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by the formula (ETM-2-1) or the formula (ETM-2-2).

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4. is there.

In the formula (ETM-2-1), R ¹¹ to R ¹⁸ are independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), and cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms). ) Or aryl (preferably aryl with 6 to 30 carbon atoms).

In the formula (ETM-2-2), R ¹¹ and R ¹² are independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), and cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms). ) Or aryl (preferably aryl having 6 to 30 carbon atoms), and R ¹¹ and R ¹² may be bonded to form a ring.

In each formula, the "pyridine-based substituent" is any of the following formulas (Py-1) to (Py-15) (* in the formula represents a bond position), and the pyridine-based substituent is Each may be independently substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl and the like, with methyl being preferred. Further, the pyridine-based substituent may be bonded to φ, anthracene ring or fluorene ring in each formula via a phenylene group or a naphthylene group.

The pyridine-based substituent is any of the formulas (Py-1) to (Py-15) (* in the formula represents the bonding position), and among these, the following formula (Py-21) It is preferably any of the formulas (Py-44).

At least one hydrogen in each pyridine derivative may be substituted with deuterium, and of the two "pyridine-based substituents" in formula (ETM-2-1) and formula (ETM-2-2). One may be replaced with aryl.

The "alkyl" in R ¹¹ to R ¹⁸ may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms and a branched chain alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms). A particularly preferable "alkyl" is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

As the alkyl having 1 to 4 carbon atoms to be substituted with the pyridine-based substituent, the above description of the alkyl can be cited.

Examples of the "cycloalkyl" in R ¹¹ to R ¹⁸ include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferable "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. A more preferable "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms.
Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl and the like.

As the "aryl" in R ¹¹ to R ¹⁸ , a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, and more preferably an aryl having 6 to 14 carbon atoms. Yes, and particularly preferably an aryl having 6 to 12 carbon atoms.

Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, which is a monocyclic aryl, (1-, 2-) naphthyl, which is a fused dicyclic aryl, and acenaphthylene-, which is a condensed tricyclic aryl (1 and 2-). 1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1-, 2-) yl, (1-, 2) -, 3-, 4-, 9-) phenanthryl, triphenylene- (1-, 2-) yl, which is a fused tetracyclic aryl, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 2-) , 2-, 5-) yl, perylene- (1-, 2-, 3-) yl, which is a fused pentacyclic aryl, pentacene- (1-, 2-, 5-, 6-) yl, etc. ..

Preferred "aryls having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl or phenanthryl, and particularly preferably phenyl, 1 -Naftil or 2-naphthyl can be mentioned.

R ¹¹ and R ¹² in the formula (ETM-2-2) may be combined to form a ring, and as a result, the 5-membered ring of the fluorene skeleton has cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane. , Fluorene, inden, etc. may be spiro-bonded.

Specific examples of this pyridine derivative include the following compounds.

This pyridine derivative can be produced by using a known raw material and a known synthesis method.

<Fluoranthene derivative>
The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and is disclosed in detail in International Publication No. 2010/134352.

In formula (ETM-3), X ¹² to X ²¹ are hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted hetero. Represents aryl. Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, cycloalkyl and the like.

Specific examples of this fluoranthene derivative include the following compounds.

<BO derivative>
The BO derivative is, for example, a multimer of a polycyclic aromatic compound represented by the following formula (ETM-4) or a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

R ¹ to R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these. May be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

Further, adjacent groups of R ¹ to R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring, and at least one hydrogen in the formed ring. May be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, in which at least one hydrogen is aryl, heteroaryl, alkyl or It may be substituted with cycloalkyl.

Further, at least one hydrogen in the compound or structure represented by the formula (ETM-4) may be substituted with halogen or deuterium.

For the explanation of the substituent and the form of ring formation in the formula (ETM-4), the description of the polycyclic aromatic compound represented by the formula (1) or the like can be cited.

Specific examples of this BO-based derivative include the following compounds.

This BO derivative can be produced using a known raw material and a known synthesis method.

<Anthracene derivative>
One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5).

Ar ¹ is independently a single bond, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

Ar ² is independently an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. .. Specific examples of "aryl having 6 to 20 carbon atoms" include phenyl, which is a monocyclic aryl, (o-, m-, p-) trill, and (2,3-,2,4-,2,5-). , 2,6-, 3,4-, 3,5-) xsilyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p-) cumenyl, bicyclic aryl (2) -, 3-, 4-) Biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenyl (m-terphenyl-2'-yl, m-terphenyl-4) '-Il, m-terphenyl-5'-il, o-terphenyl-3'-il, o-terphenyl-4'-il, p-terphenyl-2'-il, m-terphenyl-2 -Il, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p- Terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused tricyclic aryl, anthracene- (1-, 2-, 9-) yl, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluoren- (1-, 2-, 3-, 4-, 9-) il, phenalen- (1-, 2-) il, (1-, 2-) 2-, 3-, 4-, 9-) phenanthril, fused tetracyclic aryl triphenylene- (1-, 2-) yl, pyrene- (1-, 2-, 4-) yl, tetracene- (1) Examples thereof include-, 2-, 5-) yl and perylene- (1-, 2-, 3-) yl, which is a condensed pentacyclic aryl. Specific examples of the "aryl having 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetrasenyl, perylenyl and the like.

R ¹ to R ⁴ are independently hydrogen, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 6 carbon atoms, or an aryl having 6 to 20 carbon atoms.
The alkyl having 1 to 6 carbon atoms in R ¹ to R ⁴ may be either a straight chain or a branched chain. That is, it is a straight chain alkyl having 1 to 6 carbon atoms or a branched chain alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, Examples thereof include 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, etc., preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl. , Methyl, ethyl, or t-butyl is more preferred.

Specific examples of cycloalkyl having 3 to 6 carbon atoms in R ¹ to R ⁴ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl and dimethylcyclohexyl.

As for the aryl having 6 to 20 carbon atoms in R ¹ to R ^4, the aryl having 6 to 16 carbon atoms is preferable, the aryl having 6 to 12 carbon atoms is more preferable, and the aryl having 6 to 10 carbon atoms is particularly preferable. As a specific example of "aryl having 6 to 20 carbon atoms", a specific example of "aryl having 6 to 20 carbon atoms" in Ar ² can be cited. Preferred "aryl of 6-20 carbons" are phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5'-yl. More preferably, it is phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

Specific examples of these anthracene derivatives include the following compounds.

These anthracene derivatives can be produced using known raw materials and known synthetic methods.

<Benzofluorene derivative>
The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

Ar ¹ is an aryl having 6 to 20 carbon atoms independently, and the same explanation as “aryl having 6 to 20 carbon atoms” in Ar ² of the formula (ETM-5) can be quoted. Aryl having 6 to 16 carbon atoms is preferable, aryl having 6 to 12 carbon atoms is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphtylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetrasenyl, perylenyl and the like.

Ar ² is independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms). ), and the two Ar ² may form a ring.

The "alkyl" in Ar ² may be either a straight chain or a branched chain, and examples thereof include a linear alkyl having 1 to 24 carbon atoms and a branched chain alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms). A particularly preferable "alkyl" is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms). Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 Examples include -methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like.

Examples of the "cycloalkyl" in Ar ² include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferable "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. A more preferable "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl and the like.

As the "aryl" in Ar ² , a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, and more preferably an aryl having 6 to 14 carbon atoms, particularly. It is preferably an aryl having 6 to 12 carbon atoms.

Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, pentasenyl and the like.

Two Ar ² may form a ring, as a result, the 5-membered ring of the fluorene skeleton, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene are spiro-linked You may.

Specific examples of this benzofluorene derivative include the following compounds.

This benzofluorene derivative can be produced by using a known raw material and a known synthesis method.

<Phosphine oxide derivative>
The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in International Publication No. 2013/07927 and International Publication No. 2013/079678.

R ⁵ is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, an aryl having 6 to 20 carbon atoms, or a heteroaryl having 5 to 20 carbon atoms.
R ⁶ is CN, substituted or unsubstituted, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, and 5 to 5 carbon atoms. 20 heteroaryl, 1 to 20 carbon alkoxy or 6 to 20 carbon aryloxy.
R ⁷ and R ⁸ are independently substituted or unsubstituted aryls having 6 to 20 carbon atoms or heteroaryls having 5 to 20 carbon atoms, respectively.
R ⁹ is oxygen or sulfur
j is 0 or 1, k is 0 or 1, r is an integer of 0-4, and q is an integer of 1-3.
Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, cycloalkyl and the like.

The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2).

R ¹ to R ³ may be the same or different, hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), aryl thio ether (aryl). It is selected from a fused ring formed between a thioether group), an aryl, a heterocyclic group, a halogen, a cyano, an aldehyde, a carbonyl, a carboxyl, an amino, a nitro, a silyl, and an adjacent substituent.

Ar ¹ may be the same or different and is an arylene or a heteroarylene. Ar ² may be the same or different and is aryl or heteroaryl. However, at least one of Ar ¹ and Ar ² has a substituent or forms a fused ring with an adjacent substituent. n is an integer of 0 to 3, and when n is 0, the unsaturated structure portion does not exist, and when n is 3, R ¹ does not exist.

Among these substituents, alkyl means, for example, a saturated aliphatic hydrocarbon group such as methyl, ethyl, propyl, butyl, etc., which may be unsubstituted or substituted. The substituent when substituted is not particularly limited, and examples thereof include alkyl, aryl, and heterocyclic groups, and this point is also common to the following description. The number of carbon atoms of the alkyl is not particularly limited, but is usually in the range of 1 to 20 from the viewpoint of availability and cost.

Further, the cycloalkyl means, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may be substituted or substituted. The number of carbon atoms in the alkyl moiety is not particularly limited, but is usually in the range of 3 to 20.

Further, aralkyl refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon such as benzyl or phenylethyl, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be substituted or substituted. Absent. The carbon number of the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

Further, the alkenyl indicates an unsaturated aliphatic hydrocarbon group containing a double bond such as vinyl, allyl, butadienyl, etc., which may be substituted or substituted. The carbon number of the alkenyl is not particularly limited, but is usually in the range of 2 to 20.

Further, cycloalkenyl means, for example, an unsaturated alicyclic hydrocarbon group containing a double bond such as cyclopentenyl, cyclopentadienyl, cyclohexenyl, etc., which may be unsubstituted or substituted.

Further, alkynyl indicates an unsaturated aliphatic hydrocarbon group containing a triple bond such as acetylenyl, which may be unsubstituted or substituted. The carbon number of alkynyl is not particularly limited, but is usually in the range of 2 to 20.

Further, the alkoxy refers to an aliphatic hydrocarbon group via an ether bond such as methoxy, and the aliphatic hydrocarbon group may be substituted or substituted. The number of carbon atoms of the alkoxy is not particularly limited, but is usually in the range of 1 to 20.

Alkoxythio is a group in which the oxygen atom of the ether bond of alkoxy is replaced with a sulfur atom.

In addition, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is replaced with a sulfur atom.

Further, the aryl ether indicates, for example, an aromatic hydrocarbon group via an ether bond such as phenoxy, and the aromatic hydrocarbon group may be substituted or substituted. The number of carbon atoms of the aryl ether is not particularly limited, but is usually in the range of 6 to 40.

Arylthioether is a group in which the oxygen atom of the ether bond of the aryl ether is replaced with a sulfur atom.

Aryl means, for example, an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, turphenyl, and pyrenyl. Aryl may be unsubstituted or substituted. The number of carbon atoms of the aryl is not particularly limited, but is usually in the range of 6 to 40.

Further, the heterocyclic group refers to a cyclic structural group having an atom other than carbon such as flanyl, thienyl, oxazolyl, pyridyl, quinolinyl, and carbazolyl, which may be substituted or substituted. The number of carbon atoms of the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

Halogen refers to fluorine, chlorine, bromine, and iodine.

Aldehydes, carbonyls, and aminos can also contain groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like.

In addition, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocycles may be substituted or substituted.

The silyl indicates a silicon compound group such as trimethylsilyl, which may be unsubstituted or substituted. The carbon number of silyl is not particularly limited, but is usually in the range of 3 to 20. The number of silicon is usually 1 to 6.

The fused rings formed between the adjacent substituents are, for example, Ar ¹ and R ² , Ar ¹ and R ³ , Ar ² and R ² , Ar ² and R ³ , R ² and R ³ , and Ar ¹ . It is a conjugated or non-conjugated fused ring formed between Ar ^{2 and the} like. Here, when n is 1, may be formed conjugated or non-conjugated fused ring with two of R ¹ each other. These fused rings may contain nitrogen, oxygen, and sulfur atoms in the ring structure, or may be condensed with another ring.

Specific examples of this phosphine oxide derivative include the following compounds.

This phosphine oxide derivative can be produced by using a known raw material and a known synthesis method.

<Pyrimidine derivative>
The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). Details are also described in International Publication No. 2011/021689.

Ar is an aryl that may be substituted or a heteroaryl that may be substituted independently of each other. n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

Examples of the "aryl" of the "optionally substituted aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, and more preferably aryls having 6 to 20 carbon atoms. More preferably, it is an aryl having 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused bicyclic aryl. , Terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-3'-yl, tricyclic aryl -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-Il, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , Condensed tricyclic aryls, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1) -, 2-) Il, (1-, 2-, 3-, 4-, 9-) Phenantril, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, which is a tetracyclic aryl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene- (1-, 2), a fused tetracyclic aryl -) Ill, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) yl, perylene- (1-, 2-, 3-), which is a fused pentacyclic aryl ) Il, pentasen- (1-, 2-, 5-, 6-) il and the like.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferable, heteroaryl having 2 to 15 carbon atoms is further preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific heteroaryls include, for example, frills, thienyl, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, frazayl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, benzo [b] thienyl, indrill, isoindrill, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, synnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthylidine, prynyl. , Pteridinyl, carbazolyl, acridinyl, phenoxadinyl, phenothiazinyl, phenazinyl, phenoxatinyl, thiantranyl, indridinyl and the like.

Further, the above-mentioned aryl and heteroaryl may be substituted, and for example, the above-mentioned aryl and heteroaryl may be substituted, respectively.

Specific examples of this pyrimidine derivative include the following compounds.

This pyrimidine derivative can be produced by using a known raw material and a known synthesis method.

<Aryl nitrile derivative>
The arylnitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of the compounds are bonded by a single bond or the like. Details can be found in US Application Publication No. 2014/0197386.

Ar _ni preferably has a large number of carbon atoms from the viewpoint of fast electron transportability, and preferably has a small number of carbon atoms from the viewpoint of high T1. Specifically, Ar _ni is preferably a high T1 for use in a layer adjacent to the light emitting layer, is an aryl having 6 to 20 carbon atoms, and is preferably an aryl having 6 to 14 carbon atoms, more preferably. It is an aryl having 6 to 10 carbon atoms. Further, the number of substitutions n of the nitrile groups is preferably large from the viewpoint of high T1 and preferably small from the viewpoint of high S1. Specifically, the number of substitutions n of the nitrile group is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and even more preferably 1.

Ar is an aryl that may be substituted or a heteroaryl that may be substituted independently of each other. From the viewpoint of high S1 and high T1, donor heteroaryls are preferable, and donor heteroaryls are preferably small because they are used as an electron transport layer. From the viewpoint of charge transportability, aryl or heteroaryl having a large number of carbon atoms is preferable, and it is preferable to have a large number of substituents. Specifically, the number of substitutions m of Ar is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

The arylnitrile derivative may be a multimer in which a plurality of compounds represented by the formula (ETM-9) are bonded by a single bond or the like. In this case, in addition to the single bond, an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring) may be bonded.

Specific examples of this arylnitrile derivative include the following compounds.

This arylnitrile derivative can be produced using a known raw material and a known synthesis method.

This carbazole derivative can be produced using a known raw material and a known synthetic method.

<Triazine derivative>
The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). Details can be found in US Patent Application Publication No. 2011/0156013.

Ar is an aryl that may be substituted or a heteroaryl that may be substituted independently of each other. n is an integer of 1 to 3, preferably 2 or 3.

Specific examples of this triazine derivative include the following compounds.

This triazine derivative can be produced using a known raw material and a known synthesis method.

<Benzimidazole derivative>
The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzfluorene ring, phenanthrene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4. Yes, in the "benzimidazole-based substituent", the pyridyl group in the "pyridine-based substituent" in the formula (ETM-2), the formula (ETM-2-1) and the formula (ETM-2-2) is changed to benzimidazolyl. It is a substituted substituent, and at least one hydrogen in the benzimidazole derivative may be substituted with dehydrogen.

^{R 11} in the above benzimidazolyl is hydrogen, alkyl of 1 to 24 carbon atoms, aryl cycloalkyl or a C 6 to 30 3 to 12 carbon atoms, the formula (ETM-2-1) and formula (ETM-2 It may be cited to the description of ^{R 11} in -2).

φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be quoted from the description in the formula (ETM-2-1) or the formula (ETM-2-2), and each formula can be cited. In R ¹¹ to R ¹⁸ , the explanation in the formula (ETM-2-1) or the formula (ETM-2-2) can be quoted. Further, in the formula (ETM-2-1) or the formula (ETM-2-2), two pyridine-based substituents are described in a bonded form, but when these are replaced with benzoimidazole-based substituents, both are used. The pyridine-based substituent may be replaced with a benzoimidazole-based substituent (that is, n = 2), any one of the pyridine-based substituents may be replaced with the benzoimidazole-based substituent, and the other pyridine-based substituent may be replaced with R ¹¹ to. It may be replaced with R ¹⁸ (that is, n = 1). Further, for example, at least one of R ¹¹ to R ¹⁸ in the formula (ETM-2-1) may be replaced with a benzimidazole-based substituent, and the “pyridine-based substituent” may be replaced with R ¹¹ to R ¹⁸ .

Specific examples of this benzoimidazole derivative include 1-phenyl-2- (4- (10-phenylanthracene-9-yl) phenyl) -1H-benzo [d] imidazole, 2- (4- (10- (10-). Naphthalene-2-yl) anthracene-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 2- (3- (10- (naphthalen-2-yl) anthracene-9-yl) phenyl) -1-Phenyl-1H-benzo [d] imidazole, 5- (10- (naphthalene-2-yl) anthracene-9-yl) -1,2-diphenyl-1H-benzo [d] imidazole, 1- (4) -(10- (Naphthalene-2-yl) anthracene-9-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 2- (4- (9,10-di (naphthalen-2-yl)) Anthracene-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 1- (4- (9,10-di (naphthalene-2-yl) anthracene-2-yl) phenyl) -2- Examples thereof include phenyl-1H-benzo [d] imidazole and 5- (9,10-di (naphthalene-2-yl) anthracene-2-yl) -1,2-diphenyl-1H-benzo [d] imidazole.

This benzimidazole derivative can be produced using a known raw material and a known synthetic method.

<Phenanthroline derivative>
The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1). Details are described in International Publication No. 2006/021982.

R ¹¹ to R ¹⁸ of each formula are independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably carbon). The number 6 to 30 aryl). Further, in the formula (ETM-12-1), any one of R ¹¹ to R ¹⁸ is bonded to φ which is an aryl ring.

At least one hydrogen in each phenanthroline derivative may be replaced with deuterium.

Alkyl in R ¹¹ ~ ^{R 18,} cycloalkyl and aryl may be cited to the description of ^R 11 ^{~ R 18} in the formula (ETM-2). In addition to the above examples, φ has the following structural formulas, for example. In addition, R in the following structural formula is hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl independently, and * represents a binding position.

Specific examples of this phenanthroline derivative include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di (1,10-). Phenanthroline-2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, 1,3,5-tri (1,10-phenanthroline-5-yl) benzene, 9,9' -Difluoro-bi (1,10-phenanthroline-5-yl), vasocproin, 1,3-bis (2-phenyl-1,10-phenanthroline-9-yl) benzene and compounds represented by the following structural formulas can give.

This phenanthroline derivative can be produced using a known raw material and a known synthetic method.

<Kinolinol-based metal complex>
The quinolinol-based metal complex is, for example, a compound represented by the following formula (ETM-13).

In the formula, R ¹ to R ⁶ are independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl, and M is Li, Al, Ga, Be, or Zn. Yes, n is an integer of 1 to 3.

Specific examples of the quinolinol-based metal complex include 8-quinolinol lithium, tris (8-quinolinolate) aluminum, tris (4-methyl-8-quinolinolate) aluminum, tris (5-methyl-8-quinolinolate) aluminum, and tris (3). , 4-dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-8-quinolinolate) ( Phenolate) Aluminum, bis (2-methyl-8-quinolinolate) (2-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenorate) aluminum, bis (2-methyl-8- Kinolinolate) (4-methylphenorate) aluminum, bis (2-methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum, bis (2-Methyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,3-dimethylphenorate) aluminum, bis (2-methyl-8-quinolinolate) ( 2,6-Dimethylphenolate) Aluminum, bis (2-methyl-8-quinolinolate) (3,4-dimethylphenorate) Aluminum, bis (2-methyl-8-quinolinolate) (3,5-dimethylphenolate) Aluminum, bis (2-methyl-8-quinolinolate) (3,5-di-t-butylphenolate) Aluminum, bis (2-methyl-8-quinolinolate) (2,6-diphenylphenolate) Aluminum, bis ( 2-Methyl-8-quinolinolate) (2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl -8-quinolinolate) (2,4,5,6-tetramethylphenorate) aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholate) aluminum, bis (2-methyl-8-quinolinolate) (2) -Naftrat) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (2-phenylphenolate) Aluminum, bis (2,4-dimethyl-8-quinolinolate) G) (3-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethyl) Phenolate) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-di-t-butylphenolate) aluminum, bis (2-methyl-8-quinolinolate) aluminum-μ-oxo-bis ( 2-Methyl-8-quinolinolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-4-) Ethyl-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-4-ethyl-8-quinolinolate) aluminum, bis (2-methyl-4-methoxy-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-4-ethyl-8-quinolinolate) 2-Methyl-4-methoxy-8-quinolinolate) aluminum, bis (2-methyl-5-cyano-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-quinolinolate) aluminum, Bis (2-methyl-5-trifluoromethyl-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolate) aluminum, bis (10-hydroxybenzo [h] quinolinate) ) Berylium etc. can be mentioned.

This quinolinol-based metal complex can be produced by using a known raw material and a known synthesis method.

<Thiazole derivative and benzothiazole derivative>
The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).

The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2).

Φ of each formula is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is 1 to 4 The "thiazole-based substituent" and "benzothiazole-based substituent" are the "pyridine-based substituents" in the formulas (ETM-2), (ETM-2-1) and (ETM-2-2). The pyridyl in the "group" is a substituent in which the following thiazole or benzothiazolyl is replaced, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted with dehydrogen.

φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be quoted from the description in the formula (ETM-2-1) or the formula (ETM-2-2). In R ¹¹ to R ¹⁸ , the explanation in the formula (ETM-2-1) or the formula (ETM-2-2) can be quoted. Further, in the formula (ETM-2-1) or the formula (ETM-2-2), two pyridine-based substituents are described in a bonded form, and these are described as a thiazole-based substituent (or a benzothiazole-based substituent). ), Both pyridine-based substituents may be replaced with thiazole-based substituents (or benzothiazole-based substituents) (that is, n = 2), or any one of the pyridine-based substituents may be replaced with thiazole-based substituents. It may be replaced with (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R ¹¹ to R ¹⁸ (that is, n = 1). Further, for example, at least one of R ¹¹ to R ¹⁸ in the formula (ETM-2-1) is replaced with a thiazole-based substituent (or a benzothiazole-based substituent), and the "pyridine-based substituent" is replaced with R ¹¹ to R ¹⁸ . It may be replaced.

These thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthetic methods.

<Siror derivative>
The siror derivative is, for example, a compound represented by the following formula (ETM-15). Details are described in Japanese Patent Application Laid-Open No. 9-194487.

X and Y are independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, which may be substituted. For details of these groups, the explanations in the formulas (1) and (2) and the explanations in the formula (ETM-7-2) can be cited. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl moiety in the alkoxy is replaced with alkenyl or alkynyl, respectively, and the details of these alkenyl and alkynyl can be referred to in the formula (ETM-7-2).
Further, X and Y, which are all alkyl, may be bonded to form a ring.

R ¹ to R ⁴ are independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyl. Oxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocianate group, It is an isothiocyanate group or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, or may form a fused ring with an adjacent substituent.

In R ¹ ~ ^{R 4,} halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, details of the alkenyl and alkynyl can cite the description in Equation (1) and (2).

In R 1 ^~ R ^4, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, during alkoxycarbonyloxy and aryloxycarbonyloxy, alkyl, for the details of aryl and alkoxy, wherein The explanations in (1) and equation (2) can be cited.

Examples of the silyl include a silyl group and a group in which at least one of the three hydrogens of the silyl group is independently substituted with an aryl, alkyl or cycloalkyl, and a tri-substituted silyl is preferable. Examples thereof include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl and alkyldicycloalkylsilyl. For details of aryl, alkyl and cycloalkyl in these, the explanations in formulas (1) and (2) can be cited.

The fused ring formed between the adjacent substituent is, for example, a conjugated or non-conjugated fused ring formed between R ¹ and R ² , R ² and R ³ , R ³ and R ^{4, and the} like. .. These fused rings may contain nitrogen, oxygen, and sulfur atoms in the ring structure, or may be condensed with another ring.

However, preferably, when R ¹ and R ⁴ are phenyl, X and Y are not alkyl or phenyl. Also preferably, when ^{R 1} and ^{R 4} is thienyl, X and Y are alkyl, ^{R 2} and ^{R 3} form an alkyl, aryl, a ring alkenyl or ^{R 2} and ^{R 3} It is a structure that does not satisfy cycloalkyl at the same time. Also, preferably, when R ¹ and R ⁴ are silyl groups, R ² , R ³ , X and Y are independently hydrogen or alkyl having 1 to 6 carbon atoms, respectively. Also, preferably, in the case of a structure in which benzene rings are condensed at R ¹ and R ² , X and Y are not alkyl and phenyl.

These siror derivatives can be produced using known raw materials and known synthetic methods.

<Azolin derivative>
The azoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in International Publication No. 2017/014226.

In the formula (ETM-16),
φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ has 1 carbon atom. It may be substituted with an alkyl of ~ 6, a cycloalkyl of 3-14 carbons, an aryl of 6-18 carbons or a heteroaryl of 2-18 carbons.
Y is independently of -O-, -S- or> N-Ar, where Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar. May be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and R ¹ to R ⁵ are independent of each other. Hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, however, any ^one of Ar and R ¹ to R ⁵ in> N-Ar is bonded to L. Is the part to be
L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2).

In formula (L-1), X ¹ to X ⁶ are independently = CR ⁶ − or = N −, and at least two of X ¹ to X ⁶ are = CR ⁶ −, and X ¹ R ⁶ in two of ~ X ⁶ = CR ⁶ − is a site that binds to φ or an azoline ring, and R ⁶ in the other = CR ⁶ − is hydrogen.
In formula (L-2), X ⁷ to X ¹⁴ are independently = CR ^6- or = N-, and at least two of X ⁷ to X ¹⁴ are = CR ^6- , and X ⁷ R ⁶ in two = CR ⁶ − of ~ X ¹⁴ is a site that binds to φ or an azoline ring, and R ⁶ in the other = CR ⁶ − is hydrogen.
At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.
m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and
At least one hydrogen in the compound represented by the formula (ETM-16) may be substituted with deuterium.

The specific azoline derivative is a compound represented by the following formula (ETM-16-1) or formula (ETM-16-2).

In the formula (ETM-16-1) and the formula (ETM-16-2),
φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ has 1 carbon atom. It may be substituted with an alkyl of ~ 6, a cycloalkyl of 3-14 carbons, an aryl of 6-18 carbons or a heteroaryl of 2-18 carbons.
In formula (ETM-16-1), Y is independently -O-, -S- or> N-Ar, where Ar is an aryl having 6 to 12 carbon atoms or a hetero with 2 to 12 carbon atoms. It is aryl, even if at least one hydrogen of Ar is substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms. Often,
In the formula (ETM-16-1), R ¹ to R ⁴ are independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, respectively, except that R ¹ and R ² are the same. And R ³ and R ⁴ are the same,
In the formula (ETM-16-2), R ¹ to R ⁵ are independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, respectively, except that R ¹ and R ² are the same. And R ³ and R ⁴ are the same,
In the formula (ETM-16-1) and the formula (ETM-16-2),
L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2).

In formula (L-1), X ¹ to X ⁶ are independently = CR ⁶ − or = N −, and at least two of X ¹ to X ⁶ are = CR ⁶ −, and X ¹ R ⁶ in two = CR ⁶ − of ~ X ⁶ is a site that binds to φ or an azoline ring, and R ⁶ in the other = CR ⁶ − is hydrogen.
In formula (L-2), X ⁷ to X ¹⁴ are independently = CR ^6- or = N-, and at least two of X ⁷ to X ¹⁴ are = CR ^6- , and X ⁷ R ⁶ in two = CR ⁶ − of ~ X ¹⁴ is a site that binds to φ or an azoline ring, and R ⁶ in the other = CR ⁶ − is hydrogen.
At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.
m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and
At least one hydrogen in the compound represented by the formula (ETM-16-1) or the formula (ETM-16-2) may be substituted with deuterium.

Preferably, φ is a monovalent group represented by the following formulas (φ1-1) to (φ1-18) and a divalent group represented by the following formulas (φ2-1) to (φ2-34). It consists of a trivalent group represented by the following formulas (φ3-1) to (φ3-3) and a tetravalent group represented by the following formulas (φ4-1) to (φ4-2). Selected from the group, at least one hydrogen of φ is substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms or a heteroaryl having 2 to 18 carbon atoms. May be good.

Z in the formula is> CR ₂ ,>N-Ar,> N-L, -O- or -S-, and R in> CR ₂ is an alkyl having 1 to 4 carbon atoms, respectively. It is a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and R may be bonded to each other to form a ring, and Ar in> N-Ar is It is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and L in> NL is the formula (ETM-16), the formula (ETM-16-1) or the formula (ETM-16-2). Is L in. * In the formula represents the connection position.

Preferably, L is a divalent group of rings selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthylidine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine. At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.

Preferably, Ar in> N-Ar as Y or Z consists of the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyldinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl. Selected, at least one hydrogen of Ar in> N—Ar as Y may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms or an aryl having 6 to 10 carbon atoms.

Preferably, R ¹ to R ⁴ are independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, where R ¹ and R ² are the same, and R ³ and R are R. ⁴ are the same, and not that all of R ^{1 ~} R ⁴ are simultaneously hydrogen, and, m is 1 or 2, when m is 2, group formed by the azoline ring and L Are the same.

Specific examples of the azoline derivative include the following compounds. In addition, "Me" in the structural formula represents methyl.

More preferably, φ is a divalent group represented by the following formulas (φ2-1), formula (φ2-31), formula (φ2-32), formula (φ2-33) and formula (φ2-34). Selected from the group consisting of, at least one hydrogen of φ may be substituted with an aryl having 6 to 18 carbon atoms.

L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen of L is an alkyl having 1 to 4 carbon atoms and 5 to 5 carbon atoms. It may be substituted with 10 cycloalkyl, an aryl of 6 to 10 carbon atoms or a heteroaryl having 2 to 14 carbon atoms.
Ar in> N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl, and at least one hydrogen of the Ar is an alkyl having 1 to 4 carbon atoms and 5 to 5 carbon atoms. It may be substituted with 10 cycloalkyl or an aryl having 6 to 10 carbon atoms.
R ¹ to R ⁴ are independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, respectively, where R ¹ and R ² are the same, and R ³ and R ⁴ are the same. , and the addition of all the R ^{1 ~} R ⁴ are not simultaneously hydrogen, and,
m is 2, and the groups formed by the azoline ring and L are the same.

Other specific examples of the azoline derivative include, for example, the following compounds. In addition, "Me" in the structural formula represents methyl.

For details of alkyl, cycloalkyl, aryl or heteroaryl in each of the above formulas defining this azoline derivative, the explanations in formulas (1) and (2) can be cited.

This azoline derivative can be produced by using a known raw material and a known synthesis method.

The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As this reducing substance, various substances are used as long as they have a certain reducing property. For example, alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkali. From the group consisting of earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes At least one selected can be preferably used.

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), and Ca (2.95 eV). Examples thereof include alkaline earth metals such as 9 eV), Sr (2.0 to 2.5 eV) and Ba (2.52 eV), and a substance having a work function of 2.9 eV or less is particularly preferable. Of these, the more preferable reducing substance is an alkali metal of K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have a particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, the emission brightness and the life of the organic EL device can be extended. Further, as a reducing substance having a work function of 2.9 eV or less, a combination of these two or more kinds of alkali metals is also preferable, and in particular, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred. By containing Cs, the reducing ability can be efficiently exhibited, and by adding to the material forming the electron transport layer or the electron injection layer, the emission brightness and the life of the organic EL element can be extended.

The above-mentioned materials for the electron injection layer and the material for the electron transport layer are polymer compounds obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer, or a polymer crosslinked product thereof, or a main chain. A pendant type polymer compound obtained by reacting a type polymer with the above-mentioned reactive compound, or a pendant type polymer crosslinked product thereof can also be used as a material for an electron layer. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the formula (1) can be cited.
Details of the uses of such polymer compounds and crosslinked polymers will be described later.

<Cathode in organic electroluminescent device>
The cathode 108 serves to inject electrons into the light emitting layer 105 via the electron injecting layer 107 and the electron transporting layer 106.

The material for forming the cathode 108 is not particularly limited as long as it is a substance capable of efficiently injecting electrons into the organic layer, but the same material as the material for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium-silver alloy, magnesium). -Indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.) are preferable. Alloys containing lithium, sodium, potassium, cesium, calcium, magnesium or these low work function metals are effective for increasing electron injection efficiency and improving device characteristics. However, these low work function metals are generally often unstable in the atmosphere. In order to improve this point, for example, a method of doping an organic layer with a trace amount of lithium, cesium or magnesium and using a highly stable electrode is known. Inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used as other dopants. However, it is not limited to these.

In addition, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium for electrode protection, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride. , Laminating a hydrocarbon-based polymer compound or the like is a preferable example. The method for producing these electrodes is also not particularly limited as long as conduction can be obtained, such as resistance heating, electron beam deposition, sputtering, ion plating and coating.

<Binder that may be used in each layer>
The materials used for the above-mentioned hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer independently, but as a polymer binder, polyvinyl chloride, polycarbonate, etc. Polystyrene, poly (N-vinylcarbazole), polymethylmethacrylate, polybutylmethacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin It is also possible to disperse and use it in solvent-soluble resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin and other curable resins. is there.

<Method of manufacturing organic electroluminescent device>
Each layer constituting the organic EL element is made of a thin film by a method such as a vapor deposition method, a resistance heating vapor deposition, an electron beam vapor deposition, a sputtering, a molecular lamination method, a printing method, a spin coating method or a casting method, or a coating method. By setting, it can be formed. The film thickness of each layer formed in this manner is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like. When a thin film is formed by using a thin film deposition method, the vapor deposition conditions differ depending on the type of material, the target crystal structure and association structure of the film, and the like. The vapor deposition conditions are generally: boat heating temperature +50 to + 400 ° C., vacuum degree ^10-6 to ^10-3 Pa, vapor deposition rate 0.01 to 50 nm / sec, substrate temperature to -150 to + 300 ° C., film thickness 2 nm to 5 μm. It is preferable to set appropriately within the range.

When a DC voltage is applied to the organic EL element thus obtained, the anode may be applied with a positive polarity and the cathode may be applied with a negative polarity, and when a voltage of about 2 to 40 V is applied, a transparent or translucent electrode is applied. Emission can be observed from the side (anode or cathode, or both). The organic EL element also emits light when a pulse current or an alternating current is applied. The waveform of the alternating current to be applied may be arbitrary.

Next, as an example of a method for manufacturing an organic EL device, an organic EL device composed of an anode / hole injection layer / hole transport layer / light emitting layer composed of a host material and a dopant material / electron transport layer / electron injection layer / cathode. The manufacturing method of the above will be described.

<Thin-film deposition method>
A thin film of an anode material is formed on an appropriate substrate by a vapor deposition method or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on this to form a thin film to form a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a cathode material is formed by a vapor deposition method or the like. By forming it into a cathode, the desired organic EL element can be obtained. In the above-mentioned production of the organic EL device, it is also possible to reverse the production order and manufacture the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode in this order. Is.

<Wet film formation method>
The wet film forming method is carried out by preparing a low molecular weight compound capable of forming each organic layer of an organic EL device as a liquid organic layer forming composition and using the same. If there is no suitable organic solvent to dissolve this low molecular weight compound, it is high together with other monomers having a soluble function as a reactive compound in which the low molecular weight compound is substituted with a reactive substituent and a main chain type polymer. A composition for forming an organic layer may be prepared from a molecularized polymer compound or the like.

In the wet film forming method, a coating film is generally formed by undergoing a coating step of applying an organic layer forming composition to a substrate and a drying step of removing a solvent from the applied organic layer forming composition. When the polymer compound has a crosslinkable substituent (also referred to as a crosslinkable polymer compound), it is further crosslinked by this drying step to form a crosslinked polymer. Depending on the difference in the coating process, the method using a spin coater is the spin coating method, the method using the slit coater is the slit coating method, the method using the plate is gravure, offset, reverse offset, the flexographic printing method, and the method using the inkjet printer is the inkjet method. , The method of spraying in a mist form is called the spray method.

As an example, a method of forming a coating film on a substrate having a bank by using an inkjet method will be described with reference to FIG. First, the bank (200) is provided on the electrode (120) on the substrate (110). In this case, the coating film (130) can be produced by dropping ink droplets (310) between banks (200) from the inkjet head (300) and drying them. By repeating this process to prepare the next coating film (140) and further to the light emitting layer (150), and forming an electron transport layer, an electron injection layer and an electrode by a vacuum vapor deposition method, the light emitting part is separated by a bank material. It is possible to manufacture an organic EL element.

There are methods such as air drying, heating, and vacuum drying in the drying process. The drying step may be performed only once, or may be performed a plurality of times using different methods and conditions. Further, different methods may be used in combination, for example, firing under reduced pressure.

The wet film forming method is a film forming method using a solution, and is, for example, a partial printing method (injection method), a spin coating method or a casting method, a coating method, or the like. Unlike the vacuum vapor deposition method, the wet film deposition method does not require the use of an expensive vacuum vapor deposition apparatus and can form a film under atmospheric pressure. In addition, the wet film formation method enables a large area and continuous production, leading to a reduction in manufacturing cost.

On the other hand, when compared with the vacuum vapor deposition method, the wet film deposition method may be difficult to stack. When the laminated film is prepared by the wet film formation method, it is necessary to prevent the lower layer from being dissolved by the upper layer composition, and the composition with controlled solubility, the lower layer cross-linking and the orthogonal solvent (Orthogonal solvent) are dissolved in each other. No solvent) etc. are used. However, even if these techniques are used, it may be difficult to use the wet film forming method for coating all the films.

Therefore, in general, a method is adopted in which only some layers are formed by a wet film forming method and the rest are formed by a vacuum vapor deposition method to produce an organic EL element.

For example, the procedure for manufacturing an organic EL device by partially applying the wet film forming method is shown below.
(Procedure 1) Film formation by vacuum vapor deposition method of anode (Procedure 2) Film formation by wet film formation method of composition for forming hole injection layer containing material for hole injection layer (Procedure 3) Material for hole transport layer Formation of a composition for forming a hole transport layer containing (Procedure 4) Formation of a composition for forming a light emitting layer containing a host material and a dopant material by a wet film formation method (Procedure 5) Electron transport layer (Procedure 6) Film formation by vacuum vapor deposition method of electron injection layer (Procedure 7) Film formation by vacuum vapor deposition method of cathode By going through this procedure, anode / hole injection layer / hole transport An organic EL element composed of a light emitting layer / electron transport layer / electron injection layer / cathode composed of a layer / host material and a dopant material can be obtained.
Of course, there is a means for preventing the dissolution of the light emitting layer of the lower layer, or a layer including the material for the electron transport layer and the material for the electron injection layer is formed by using a means for forming a film from the cathode side contrary to the above procedure. It can be prepared as a composition for use and deposited by a wet film forming method.

<Other film formation methods>
A laser heating drawing method (LITI) can be used to form a film of the composition for forming an organic layer. LITI is a method in which a compound attached to a substrate is heated and vapor-deposited with a laser, and an organic layer forming composition can be used as a material to be applied to the substrate.

<Arbitrary process>
Appropriate treatment steps, cleaning steps, and drying steps may be appropriately added before and after each step of film formation. Examples of the treatment step include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for producing a bank can be mentioned.

Photolithography technology can be used to create the bank. As the bank material that can be used for photolithography, a positive resist material and a negative resist material can be used. In addition, patternable printing methods such as an inkjet method, gravure offset printing, reverse offset printing, and screen printing can also be used. In that case, a permanent resist material can also be used.

Materials used for banks include polysaccharides and derivatives thereof, homopolymers and copolymers of ethylenic monomers having hydroxyls, biopolymer compounds, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, and polyetherimides. , Polysulfide, polysulfone, polyphenylene, polyphenyl ether, polyurethane, epoxy (meth) acrylate, melamine (meth) acrylate, polyolefin, cyclic polyolefin, acrylonitrile-butadiene-styrene copolymer polymer (ABS), silicone resin, polyvinyl chloride, chlorine Fluoropolymers such as polyethylene chemicals, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, polyfluorovinylidene, polytetrafluoroethylene, polyhexafluoropropylene, fluoroolefin-hydrocarbon olefin copolymer polymer, fluorocarbon polymer, etc. However, it is not limited to that.

<Composition for forming an organic layer used in a wet film formation method>
The composition for forming an organic layer is obtained by dissolving a low molecular weight compound capable of forming each organic layer of an organic EL element or a high molecular weight compound obtained by polymerizing the low molecular weight compound in an organic solvent. For example, the composition for forming a light emitting layer includes a polycyclic aromatic compound (or a polymer compound thereof) which is at least one type of dopant material as a first component, at least one kind of host material as a second component, and a third component. It contains at least one organic solvent as a component. The first component functions as a dopant component of the light emitting layer obtained from the composition, and the second component functions as a host component of the light emitting layer. The third component functions as a solvent for dissolving the first component and the second component in the composition, and at the time of application, the third component itself gives a smooth and uniform surface shape by the controlled evaporation rate of the third component itself.

<Organic solvent>
The composition for forming an organic layer contains at least one kind of organic solvent. By controlling the evaporation rate of the organic solvent at the time of film formation, it is possible to control and improve the film forming property, the presence or absence of defects in the coating film, the surface roughness, and the smoothness. Further, when the film is formed by using the inkjet method, the meniscus stability at the pinhole of the inkjet head can be controlled, and the ejection property can be controlled and improved. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, the electrical characteristics, light emission characteristics, efficiency, and life of the organic EL device having the organic layer obtained from the composition for forming the organic layer can be improved. Can be done.

(1) Physical Properties of Organic Solvent The boiling point of at least one organic solvent is 130 ° C. to 300 ° C., more preferably 140 ° C. to 270 ° C., and even more preferably 150 ° C. to 250 ° C. When the boiling point is higher than 130 ° C., it is preferable from the viewpoint of ejection property of the inkjet. Further, when the boiling point is lower than 300 ° C., it is preferable from the viewpoint of coating film defects, surface roughness, residual solvent and smoothness. The organic solvent is more preferably configured to contain two or more kinds of organic solvents from the viewpoint of good inkjet ejection property, film forming property, smoothness and low residual solvent. On the other hand, in some cases, the composition may be in a solid state by removing the solvent from the composition for forming an organic layer in consideration of transportability and the like.

Further, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP _GS ) of the good solvent (GS) is higher than the boiling point (BP _PS ) of the poor solvent (PS). Also low, configuration is particularly preferred.
By adding the poor solvent having a high boiling point, the good solvent having a low boiling point volatilizes first at the time of film formation, and the concentration of the content in the composition and the concentration of the poor solvent increase to promote rapid film formation. As a result, a coating film having few defects, a small surface roughness, and high smoothness can be obtained.

Differential solubility _(S GS _{-S PS)} is preferably 1% or more, more preferably 3% or more, more preferably 5% or more. The difference in boiling points (BP _PS- BP _GS ) is preferably 10 ° C. or higher, more preferably 30 ° C. or higher, and even more preferably 50 ° C. or higher.

The organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, and heating after the film formation. When heating is performed, it is preferable to perform heating at a glass transition temperature (Tg) of at least one kind of solute + 30 ° C. or less from the viewpoint of improving the coating film-forming property. From the viewpoint of reducing the residual solvent, it is preferable to heat the solute at at least one glass transition point (Tg) of −30 ° C. or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Further, the drying may be performed a plurality of times at different temperatures, or a plurality of drying methods may be used in combination.

(2) Specific Examples of Organic Solvents Examples of the organic solvent used in the composition for forming an organic layer include an alkylbenzene solvent, a phenyl ether solvent, an alkyl ether solvent, a cyclic ketone solvent, an aliphatic ketone solvent, and a monocyclic solvent. Examples thereof include a ketone solvent, a solvent having a diester skeleton, and a fluorine-containing solvent. Specific examples thereof include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, and the like. Heptane-2-ol, octane-2-ol, decane-2-ol, dodecane-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol Monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol Dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene , O-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoro Anisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mecitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methyl Anisole, phenetol, benzodioxol, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methyl Anisole, Simene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, Decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, benzoic acid Methyl, isopentylbenzene, 3,4-dimethylanisole, o-tornitrile, n-amylbenzene, veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene , 1-Methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-vitril, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydro Benzofuran, 1-methyl-4- (propoxymethyl) benzene, 1-methyl-4- (butyloxymethyl) benzene, 1-methyl-4- (pentyloxymethyl) benzene, 1-methyl-4- (hexyloxymethyl) ) Benzene, 1-methyl-4- (heptyloxymethyl) benzenebenzylbutyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, benzyloctyl ether and the like, but are not limited thereto. Moreover, the solvent may be used alone or may be mixed.

<Arbitrary ingredient>
The composition for forming an organic layer may contain an arbitrary component as long as the properties are not impaired. Examples of the optional component include a binder and a surfactant.

(1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film at the time of film formation and joins the obtained film to the substrate. It also plays a role in dissolving, dispersing and binding other components in the composition for forming an organic layer.

Examples of the binder used in the composition for forming an organic layer include acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, and the like. Ionomer, chlorinated polyether, diallyl phthalate resin, unsaturated polyester resin, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resin, acrylonitrile -Styrene copolymer (AS) resin, phenol resin, epoxy resin, melamine resin, urea resin, alkyd resin, polyurethane, and copolymers of the above resins and polymers, but are not limited thereto.

The binder used in the composition for forming an organic layer may be only one type or a mixture of a plurality of types.

(2) Surfactant The composition for forming an organic layer contains, for example, a surfactant for controlling the film surface uniformity, the solvent-like property and the liquid repellency of the film surface of the composition for forming an organic layer. May be good. Surfactants are classified into ionic and nonionic based on the structure of hydrophilic groups, and further classified into alkyl-based, silicon-based and fluorine-based based on the structure of hydrophobic groups. Further, from the molecular structure, it is classified into a monomolecular system having a relatively small molecular weight and a simple structure and a polymer system having a large molecular weight and having side chains and branches. Further, it is classified into a single system, a mixed system in which two or more kinds of surfactants and a base material are mixed, according to the composition. As the surfactant that can be used in the composition for forming an organic layer, all kinds of surfactants can be used.

Examples of the surfactant include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade name, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbak 161, Disperbake 162, Disperbake 163, Disperbake 164, Disperbake 166, Disperbake 170, Disperbake 180, Disperbake 181 and Disper. Bake 182, BYK300, BYK306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade name, manufactured by Big Chemie Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF -50-100CS (trade name, manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ethylene 222F, Ethylene 251 and FTX-218 (trade name) Product name, Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (trade name, manufactured by Mitsubishi Materials Co., Ltd.), Megafuck F- 470, Megafuck F-471, Megafuck F-475, Megafuck R-08, Megafuck F-477, Megafuck F-479, Megafuck F-553, Megafuck F-554 (trade name, DIC Co., Ltd.) ), Fluoroalkylbenzene sulfonate, Fluoralkylcarboxylate, Fluoroalkyl polyoxyethylene ether, Fluoroalkyl ammonium iodide, Fluoroalkyl betaine, Fluoroalkyl sulfonate, Diglycerin tetrakis (fluoroalkyl polyoxyethylene ether) ), Fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene Steerate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, Polyoxyethylene sorbitan oleate, polyoxyethyle Examples thereof include naphthyl ether, alkylbenzene sulfonate and alkyldiphenyl ether disulfonate.

Further, the surfactant may be used alone or in combination of two or more.

<Composition and physical properties of composition for forming organic layer>
The content of each component in the composition for forming an organic layer is obtained from the good solubility, storage stability and film forming property of each component in the composition for forming an organic layer, and the composition for forming an organic layer. Good film quality of the coating film, good ejection property when the inkjet method is used, and good electrical characteristics, light emission characteristics, efficiency, and life of the organic EL element having an organic layer produced by using the composition. It is decided in consideration of the viewpoint of. For example, in the case of a composition for forming a light emitting layer, the first component is 0.0001% by mass to 2.0% by mass with respect to the total mass of the composition for forming a light emitting layer, and the second component is for forming a light emitting layer. 0.0999% by mass to 8.0% by mass with respect to the total mass of the composition, and 90.0% by mass to 99.9% by mass with respect to the total mass of the composition for forming the light emitting layer as the third component. preferable.

More preferably, the first component is 0.005% by mass to 1.0% by mass with respect to the total mass of the light emitting layer forming composition, and the second component is based on the total mass of the light emitting layer forming composition. 0.095% by mass to 4.0% by mass, and the third component is 95.0% by mass to 99.9% by mass with respect to the total mass of the composition for forming a light emitting layer. More preferably, the first component is 0.05% by mass to 0.5% by mass with respect to the total mass of the light emitting layer forming composition, and the second component is based on the total mass of the light emitting layer forming composition. The third component is 0.25% by mass to 2.5% by mass, and the third component is 97.0% by mass to 99.7% by mass with respect to the total mass of the composition for forming a light emitting layer.

The composition for forming an organic layer can be produced by appropriately selecting the above-mentioned components by a known method such as stirring, mixing, heating, cooling, dissolving, and dispersing. Further, after the preparation, filtration, degassing (also referred to as degas), ion exchange treatment, inert gas replacement / encapsulation treatment and the like may be appropriately selected.

As for the viscosity of the composition for forming an organic layer, the higher the viscosity, the better the film forming property and the good ejection property when the inkjet method is used. On the other hand, the lower the viscosity, the easier it is to form a thin film. From this, the viscosity of the composition for forming an organic layer is preferably 0.3 to 3 mPa · s at 25 ° C., and more preferably 1 to 3 mPa · s. In the present invention, the viscosity is a value measured using a conical flat plate type rotational viscometer (cone plate type).

The lower the surface tension of the composition for forming an organic layer, the better the film forming property and the coating film without defects. On the other hand, the higher the value, the better the inkjet ejection property. From this, the viscosity of the composition for forming an organic layer is preferably 20 to 40 mN / m and more preferably 20 to 30 mN / m in surface tension at 25 ° C. In the present invention, the surface tension is a value measured by using the suspension method.

<Crosslinkable polymer compound: Compound represented by the formula (XLP-1)>
Next, a case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following formula (XLP-1).

In equation (XLP-1)
MUx, ECx and k have the same definition as MU, EC and k in formula (SPH-1), except that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS). The content of the monovalent or divalent aromatic group having a crosslinkable substituent is preferably 0.1 to 80% by mass in the molecule.

The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably 0.5 to 50% by mass, more preferably 1 to 20% by mass.

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group capable of further crosslinking the above-mentioned polymer compound, but a substituent having the following structure is preferable. * In each structural formula indicates the bonding position.

Examples of the divalent aromatic compound having a crosslinkable substituent include a compound having the following partial structure.

<Manufacturing method of polymer compound and crosslinkable polymer compound>
The method for producing the polymer compound and the crosslinkable polymer compound will be described by taking the compound represented by the above formula (SPH-1) and the compound represented by (XLP-1) as examples. These compounds can be synthesized by appropriately combining known production methods.

Examples of the solvent used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents and the like, and examples thereof include dimethoxyethane, 2- (2-methoxyethoxy) ethane, and 2- (2). -Ethoxyethoxy) ethane and the like.

Further, the reaction may be carried out in a two-phase system. When the reaction is carried out in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added, if necessary.

When producing the compound of the formula (SPH-1) and the compound of (XLP-1), it may be produced in one step or in multiple steps. Further, it may be carried out by a batch polymerization method in which the reaction is started after all the raw materials are placed in the reaction vessel, or it may be carried out by a dropping polymerization method in which the raw materials are added dropwise to the reaction vessel, and the product advances the reaction. It may be carried out by a precipitation polymerization method in which the mixture precipitates, and these can be combined and synthesized as appropriate. For example, when the compound represented by the formula (SPH-1) is synthesized in one step, a monomer having a polymerizable group bonded to a monomer unit (MU) and a monomer having a polymerizable group bonded to an end cap unit (EC) are used. The desired product is obtained by carrying out the reaction in the state of being added to the reaction vessel. Further, when the compound represented by the formula (SPH-1) is synthesized in multiple stages, a monomer having a polymerizable group bonded to a monomer unit (MU) is polymerized to a target molecular weight, and then the end cap unit (EC) is formed. The desired product is obtained by adding a monomer having a polymerizable group bonded thereto and reacting the mixture. By adding a monomer having a polymerizable group bonded to a different type of monomer unit (MU) in multiple stages and carrying out a reaction, a polymer having a concentration gradient with respect to the structure of the monomer unit can be produced. In addition, after preparing the precursor polymer, the target polymer can be obtained by a post-reaction.

In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer. For example, as shown in 1 to 3 of the synthetic scheme, it is possible to synthesize a polymer having a random primary structure (1 of the synthetic scheme), a polymer having a regular primary structure (2 and 3 of the synthetic scheme), and the like. Therefore, it can be used in combination as appropriate according to the target product. Furthermore, hyperbranched polymers and dendrimers can be synthesized by using a monomer unit having three or more polymerizable groups.

Examples of the monomers that can be used in the present invention include JP-A-2010-189630, International Publication No. 2012/086671, International Publication No. 2013/91088, International Publication No. 2002/045184, International Publication No. 2011/049421. , International Publication No. 2013/146806, International Publication No. 2005/0495446, International Publication No. 2015/145871, Japanese Patent Application Laid-Open No. 2010-215886, Japanese Patent Application Laid-Open No. 2008-106241, Japanese Patent Application Laid-Open No. 2010-215886, International Publication No. It can be synthesized according to the methods described in 2016/031639, Japanese Patent Application Laid-Open No. 2011-174062, International Publication No. 2016/031639, International Publication No. 2016/031639, and International Publication No. 2002/045184.

Regarding specific polymer synthesis procedures, Japanese Patent Application Laid-Open No. 2012-0363888, International Publication No. 2015/008851, Japanese Patent Application Laid-Open No. 2012-366381, Japanese Patent Application Laid-Open No. 2012-144722, International Publication No. 2015/194448 , International Publication No. 2013/146806, International Publication No. 2015/145871, International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2016/031639, International Publication No. 2016/031639, International It can be synthesized according to the methods described in Publication No. 2016/125560, International Publication No. 2015/145871, International Publication No. 2011/049241, and Japanese Patent Application Laid-Open No. 2012-144722.

<Application example of organic electroluminescent device>
The present invention can also be applied to a display device provided with an organic EL element, a lighting device provided with an organic EL element, and the like.
A display device or a lighting device provided with an organic EL element can be manufactured by a known method such as connecting an organic EL element according to the present embodiment to a known drive device, and can be manufactured by a known method such as DC drive, pulse drive, AC drive, or the like. It can be driven by appropriately using a known driving method.

Examples of the display device include a panel display such as a color flat panel display and a flexible display such as a flexible color organic electroluminescent (EL) display (for example, JP-A-10-335066, JP-A-2003-321546). See Japanese Patent Application Laid-Open No. 2004-281086, etc.). Further, as the display method of the display, for example, a matrix and / or a segment method can be mentioned. The matrix display and the segment display may coexist in the same panel.

In the matrix, pixels for display are arranged two-dimensionally such as in a grid pattern or mosaic pattern, and characters and images are displayed as a set of pixels. The shape and size of the pixels are determined by the application. For example, for displaying images and characters on a personal computer, monitor, or television, quadrangular pixels with a side of 300 μm or less are usually used, and in the case of a large display such as a display panel, pixels with a side on the order of mm should be used. become. In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. Then, as the driving method of this matrix, either a line sequential driving method or an active matrix may be used. Line sequential drive has the advantage of a simpler structure, but when considering operating characteristics, the active matrix may be superior, so it is also necessary to use it properly depending on the application.

In the segment method (type), a pattern is formed so as to display predetermined information, and a predetermined area is made to emit light. For example, time and temperature displays on digital clocks and thermometers, operating status displays of audio equipment and electromagnetic cookers, and panel displays of automobiles can be mentioned.

Examples of the lighting device include a lighting device such as an indoor lighting device, a backlight of a liquid crystal display device, and the like (for example, Japanese Patent Application Laid-Open No. 2003-257621, Japanese Patent Application Laid-Open No. 2003-277741, Japanese Patent Application Laid-Open No. 2004-119211 Etc.). The backlight is mainly used for the purpose of improving the visibility of a display device that does not emit light by itself, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display board, a sign, and the like. In particular, as a backlight for a liquid crystal display device, especially for a personal computer for which thinning is an issue, considering that it is difficult to thin the backlight because the conventional method consists of a fluorescent lamp and a light guide plate, the present embodiment The backlight using the light emitting element according to the above is characterized by being thin and lightweight.

3-2. Other Organic Devices The polycyclic aromatic compounds according to the present invention can be used for producing organic field effect transistors, organic thin-film solar cells, and the like, in addition to the above-mentioned organic field-emitting devices.

The organic field effect transistor is a transistor that controls the current by the electric field generated by the voltage input, and is provided with a gate electrode in addition to the source electrode and drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) flowing between the source electrode and the drain electrode can be arbitrarily blocked to control the current. The field effect transistor is easier to miniaturize than a simple transistor (bipolar transistor), and is often used as an element constituting an integrated circuit or the like.

The structure of the organic field effect transistor is usually provided with a source electrode and a drain electrode in contact with the organic semiconductor active layer formed by using the polycyclic aromatic compound according to the present invention, and further in contact with the organic semiconductor active layer. It suffices if the gate electrode is provided so as to sandwich the insulating layer (dielectric layer). Examples of the element structure include the following structures.
(1) Substrate / Gate electrode / Insulator layer / Source electrode / Drain electrode / Organic semiconductor active layer (2) Substrate / Gate electrode / Insulator layer / Organic semiconductor active layer / Source electrode / Drain electrode (3) Substrate / Organic Semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic electric field effect transistor configured in this way is It can be applied as a pixel-driven switching element of an active matrix-driven liquid crystal display or an organic electroluminescence display.

The organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer, depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin film solar cell. In addition to the above, the organic thin film solar cell may appropriately include a hole block layer, an electron block layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. For the organic thin-film solar cell, known materials used for the organic thin-film solar cell can be appropriately selected and used in combination.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto. First, an example of synthesizing a polycyclic aromatic compound will be described below.

Synthesis example (1)
Synthesis of Compound (1F-1) 1.6 M tert-Butyllithium in a flask containing compound (X-1) (7.7 g) and tert-butylbenzene (50 ml) at −30 ° C. under a nitrogen atmosphere. A pentane solution (12.3 ml) was added. After completion of the dropping, the temperature was raised to 60 ° C. and the mixture was stirred for 2 hours, and then components having a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to −30 ° C., boron tribromide (5 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. Then, the mixture was cooled to 0 ° C. again, N, N-diisopropylethylamine (3.5 ml) was added, and the mixture was stirred at room temperature until the exotherm subsided, then heated to 120 ° C. and heated and stirred for 3 hours. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath and then heptane were added to separate the layers. Then, after purification with a silica gel short pass column (additional solution: toluene), the solvent was distilled off under reduced pressure, the obtained solid was dissolved in toluene, heptane was added and reprecipitated, and the mixture was represented by the formula (1F-1). Compound can be obtained.
EI-MS: m / z = 740

Synthesis example (2)
Synthesis of Compound (1F-2) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-2) can be obtained using the compound (X-2).
EI-MS: m / z = 759

Synthesis example (3)
Synthesis of Compound (1F-3) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-3) can be obtained using the compound (X-3).
EI-MS: m / z = 756

Synthesis example (4)
Synthesis of Compound (1F-4) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-4) can be obtained using the compound (X-4).
EI-MS: m / z = 756

Synthesis example (5)
Synthesis of Compound (1F-5) Compound (X-5) (5.5 g), Aluminum Chloride (5.0 g), N, N-diisopropylethylamine (EtN ⁱ Pr ₂ ) (6.5 mL) and Chlorobenzene (20 ml) The flask containing the mixture was stirred at 120 ° C. for 1 hour under a nitrogen atmosphere. The reaction mixture cooled to room temperature was poured into ice water (200 ml), toluene was added, and the organic layer was extracted. The solvent of the organic layer was distilled off under reduced pressure, and the obtained solid was dissolved in chloroform and passed through a silica gel short pass column (eluent: toluene). The crude product obtained by distilling off the solvent under reduced pressure is reprecipitated with cyclopentyl methyl ether and methanol to obtain a compound represented by the formula (1F-5).
EI-MS: m / z = 809

Synthesis example (6)
Synthesis of Compound (1F-6) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-6) can be obtained using the compound (X-6).
EI-MS: m / z = 740

Synthesis example (7)
Synthesis of Compound (1F-7) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-7) can be obtained using the compound (X-7).
EI-MS: m / z = 756

Synthesis example (8)
Synthesis of Compound (1F-8) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-8) can be obtained using the compound (X-8).
EI-MS: m / z = 756

Synthesis example (9)
Synthesis of Compound (1F-9) Using the same method as in Synthesis Example (5), the compound represented by the formula (1F-9) can be obtained using the compound (X-9).
EI-MS: m / z = 811

Synthesis example (10)
Synthesis of Compound (1F-10) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-10) can be obtained using the compound (X-10).
EI-MS: m / z = 756

Synthesis example (11)
Synthesis of Compound (1F-11) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-11) can be obtained using the compound (X-11).
EI-MS: m / z = 756

Synthesis example (12)
Synthesis of Compound (1F-12) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-12) can be obtained using the compound (X-12).
EI-MS: m / z = 756

Synthesis example (13)
Synthesis of Compound (1F-13) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-13) can be obtained using the compound (X-13).
EI-MS: m / z = 756

Synthesis example (14)
Synthesis of Compound (1F-14) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-14) can be obtained using the compound (X-14).
EI-MS: m / z = 817

Synthesis example (15)
Synthesis of Compound (1F-15) Using the same method as in Synthesis Example (1), a compound represented by the formula (1F-15) can be obtained using the compound (X-15).
EI-MS: m / z = 756

Synthesis example (16)
Synthesis of Compound (1F-16) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-16) can be obtained using the compound (X-16).
EI-MS: m / z = 756

Synthesis example (17)
Synthesis of Compound (1F-17) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-17) can be obtained using the compound (X-17).
EI-MS: m / z = 756

Synthesis example (18)
Synthesis of Compound (1F-18) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-18) can be obtained using the compound (X-18).
EI-MS: m / z = 889

Synthesis example (19)
Synthesis of Compound (1F-19) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-19) can be obtained using the compound (X-19).
EI-MS: m / z = 923

Synthesis example (20)
Synthesis of Compound (1F-20) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-20) can be obtained using the compound (X-20).
EI-MS: m / z = 818

Synthesis example (21)
Synthesis of Compound (1F-21) Using the same method as in Synthesis Example (1), a compound represented by the formula (1F-21) can be obtained using the compound (X-21).
EI-MS: m / z = 874

Synthesis example (22)
Synthesis of Compound (1F-22) Using the same method as in Synthesis Example (1), a compound represented by the formula (1F-22) can be obtained using compound (X-22).
EI-MS: m / z = 802

Synthesis example (23)
Synthesis of Compound (1F-23) Using the same method as in Synthesis Example (5), the compound represented by the formula (1F-23) can be obtained using the compound (X-23).
EI-MS: m / z = 852

Synthesis example (24)
Synthesis of Compound (1F-24) Using the same method as in Synthesis Example (5), the compound represented by the formula (1F-24) can be obtained using the compound (X-24).
EI-MS: m / z = 786

Synthesis example (25)
Synthesis of Compound (1F-25) Using the same method as in Synthesis Example (1), compound (X-25) is used to obtain a compound represented by the formula (1F-25).
EI-MS: m / z = 790

Synthesis example (26)
Synthesis of Compound (1F-26) Using the same method as in Synthesis Example (1), compound (X-26) is used to obtain a compound represented by the formula (1F-26).
EI-MS: m / z = 953

Synthesis example (27)
Synthesis of Compound (1F-27) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-27) can be obtained using the compound (X-27).
EI-MS: m / z = 774

Synthesis example (28)
Synthesis of Compound (1F-28) Using the same method as in Synthesis Example (1), compound (X-28) is used to obtain a compound represented by the formula (1F-28).
EI-MS: m / z = 790

Synthesis example (29)
Synthesis of Compound (1F-29) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-29) can be obtained using the compound (X-29).
EI-MS: m / z = 1000

Synthesis example (30)
Synthesis of Compound (1F-30) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-30) can be obtained using the compound (X-30).
EI-MS: m / z = 798

Synthesis example (31)
Synthesis of Compound (1F-31) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-31) can be obtained using the compound (X-31).
EI-MS: m / z = 1056

Synthesis example (32)
Synthesis of Compound (1F-32) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-32) can be obtained using the compound (X-32).
EI-MS: m / z = 738

Synthesis example (33)
Synthesis of Compound (1F-33) Using the same method as in Synthesis Example (1), compound (X-33) is used to obtain a compound represented by the formula (1F-33).
EI-MS: m / z = 770

Synthesis example (34)
Synthesis of Compound (1F-34) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-34) can be obtained by using the compound (X-34).
EI-MS: m / z = 738

Synthesis example (35)
Synthesis of Compound (1F-35) Using the same method as in Synthesis Example (1), compound (X-35) is used to obtain a compound represented by the formula (1F-35).
EI-MS: m / z = 889

Synthesis example (36)
Synthesis of Compound (1F-36) Using the same method as in Synthesis Example (1), a compound represented by the formula (1F-36) can be obtained using compound (X-36).
EI-MS: m / z = 785

Synthesis example (37)
Synthesis of Compound (1F-37) Using the same method as in Synthesis Example (1), compound (X-37) is used to obtain a compound represented by the formula (1F-37).
EI-MS: m / z = 800

Synthesis example (38)
Synthesis of Compound (1F-38) Using the same method as in Synthesis Example (1), compound (X-38) is used to obtain a compound represented by the formula (1F-38).
EI-MS: m / z = 887

Synthesis example (39)
Synthesis of Compound (1F-39) Using the same method as in Synthesis Example (1), compound (X-39) is used to obtain a compound represented by the formula (1F-39).
EI-MS: m / z = 867
^{1 1} H-NMR (CDCl ₃ ): δ = 1.1 (s, 9H), 1.3 (s, 9H), 1.4 (s, 9H), 1.5 (s, 9H), 5.6 (S, 1H), 5.7 (s, 1H), 6.5 (d, 1H), 6.6 (d, 1H), 6.9 (t, 2H), 7.0 (d, 4H) , 7.1 (t, 4H), 7.1 (d, 2H), 7.3 (d, 2H), 7.4 (dd, 1H), 7.4 (dd, 1H), 7.5 ( d, 2H), 7.5 (d, 2H), 7.9 (d, 1H), 8.7 (d, 1H).

Synthesis example (40)
Synthesis of Compound (1F-40) Using the same method as in Synthesis Example (1), compound (X-40) is used to obtain a compound represented by the formula (1F-40).
EI-MS: m / z = 1000
^{1 1} H-NMR (CDCl ₃ ): δ = 1.0 (s, 9H), 1.2 (s, 9H), 1.3 (s, 9H), 1.4 (s, 9H), 1.5 (S, 9H), 5.7 (s, 1H), 5.7 (s, 1H), 6.5 (s, 1H), 6.7 (d, 1H), 6.9 (m, 6H) , 7.1 (m, 9H), 7.3 (m, 2H), 7.4 (dd, 1H), 7.4 (m, 2H), 7.5 (m, 3H), 7.9 ( d, 1H), 8.7 (d, 1H).

Synthesis example (41)
Synthesis of Compound (1F-41) Using the same method as in Synthesis Example (1), compound (X-41) is used to obtain a compound represented by the formula (1F-41).
EI-MS: m / z = 889

Synthesis example (42)
Synthesis of Compound (1F-42) Using the same method as in Synthesis Example (1), compound (X-42) is used to obtain a compound represented by the formula (1F-42).
EI-MS: m / z = 740

Synthesis example (43)
Synthesis of Compound (1F-43) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-43) can be obtained by using the compound (X-43).
EI-MS: m / z = 945

Synthesis example (44)
Synthesis of Compound (1F-44) Using the same method as in Synthesis Example (1), compound (X-44) is used to obtain a compound represented by the formula (1F-44).
EI-MS: m / z = 889
^{1 1} H-NMR (CDCl ₃ ): δ = 1.0 (s, 9H), 1.1 (s, 9H), 1.3 (s, 9H), 1.5 (s, 9H), 1.5 (S, 9H), 1.5 (s, 9H), 6.2 (d, 2H), 6.6 (s, 1H), 6.7 (s, 1H), 7.0 (d, 2H) , 7.2 (m, 3H), 7.4 (dd, 1H), 7.4 to 7.5 (m, 3H), 7.6 (dd, 1H), 7.7 (d, 1H), 7.7 (d, 2H), 7.9 (d, 1H), 8.7 (d, 1H).

Synthesis example (45)
Synthesis of Compound (1F-45) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-45) can be obtained by using the compound (X-45).
EI-MS: m / z = 903

Synthesis example (46)
Synthesis of Compound (1F-46) Using the same method as in Synthesis Example (1), compound (X-46) is used to obtain a compound represented by the formula (1F-46).
EI-MS: m / z = 1000

Synthesis example (47)
Synthesis of Compound (1F-47) Using the same method as in Synthesis Example (1), compound (X-47) can be used to obtain the compound represented by the formula (1F-47). EI-MS: m / z = 865

Synthesis example (48)
Synthesis of Compound (1F-48) Using the same method as in Synthesis Example (1), compound (X-48) is used to obtain a compound represented by the formula (1F-48).
HRMS m / z 846.5671 (calcd C ₆₀ H ₇₁ BN ₂ O, 846.5569).

Synthesis example (49)
Synthesis of Compound (1F-49) Using the same method as in Synthesis Example (1), compound (X-49) is used to obtain a compound represented by the formula (1F-49).
HRMS m / z 898.5955 (calcd C ₆₄ H ₇₅ BN ₂ O, 898.5972).

Synthesis example (50)
Synthesis of Compound (1F-50) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-50) can be obtained using the compound (X-50).
HRMS m / z 901.5163 (calcd C ₆₄ H ₆₄ BN ₃ O, 901.5142).

Synthesis example (51)
Synthesis of Compound (1F-51) Using the same method as in Synthesis Example (1), compound (X-51) is used to obtain a compound represented by the formula (1F-51).
HRMS m / z 846.5.668 (calcd C ₆₀ H ₇₁ BN ₂ O, 846.5569).

Synthesis example (52)
Synthesis of Compound (1F-52) Using the same method as in Synthesis Example (1), compound (X-52) is used to obtain a compound represented by the formula (1F-52).
HRMS m / z 898.5988 (calcd C ₆₄ H ₇₅ BN ₂ O, 898.5972).

Synthesis example (53)
Synthesis of Compound (1F-53) Using the same method as in Synthesis Example (1), compound (X-53) is used to obtain a compound represented by the formula (1F-53).
HRMS m / z 901.5161 (calcd C ₆₄ H ₆₄ BN ₃ O, 901.5142).

Synthesis example (54)
Synthesis of Compound (1F-54) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-54) can be obtained using the compound (X-54).
HRMS m / z 991.5238 (calcd C ₇₀ H ₆₆ BN ₃ O ₂ , 991.5248).

Synthesis example (55)
Synthesis of Compound (1F-55) Using the same method as in Synthesis Example (1), compound (X-55) is used to obtain a compound represented by the formula (1F-55).
HRMS m / z 1012.6095 (calcd C ₇₂ H ₇₇ BN ₂ O ₂ , 1012.6078).

Synthesis example (56)
Synthesis of Compound (1F-56) Using the same method as in Synthesis Example (1), compound (X-56) is used to obtain a compound represented by the formula (1F-56).
HRMS m / z 988.6050 (calcd C ₇₀ H ₇₇ BN ₂ O ₂ , 988.6078).

Synthesis example (57)
Synthesis of Compound (1F-57) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-57) can be obtained by using the compound (X-57).
HRMS m / z 1103.6522 (calcd C ₇₈ H ₈₂ BN ₃ O ₂ , 1103.6500).

Synthesis example (58)
Synthesis of Compound (1F-58) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-58) can be obtained using the compound (X-58).
HRMS m / z 1012.6059 (calcd C ₇₂ H ₇₇ BN ₂ O ₂ , 1012.6078).

Synthesis example (59)
Synthesis of Compound (1F-59) Using the same method as in Synthesis Example (1), compound (X-59) is used to obtain a compound represented by the formula (1F-59).
HRMS m / z 988.6088 (calcd C ₇₀ H ₇₇ BN ₂ O ₂ , 988.6078).

Synthesis example (60)
Synthesis of Compound (1F-60) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-60) can be obtained using the compound (X-60).
HRMS m / z 651.4085 (calcd C ₄₅ H ₅₄ BNS, 651.4070).

Synthesis example (61)
Synthesis of Compound (1F-61) Using the same method as in Synthesis Example (1), compound (X-61) is used to obtain a compound represented by the formula (1F-61).
HRMS m / z 701.4241 (calcd C ₄₉ H ₅₆ BNS, 701.4227).

Synthesis example (62)
Synthesis of Compound (1F-62) Using the same method as in Synthesis Example (1), compound (X-62) is used to obtain a compound represented by the formula (1F-62).
HRMS m / z 818.3911 (calcd C ₅₅ H ₅₅ BN ₂ S ₂ , 818.3900).

Synthesis example (63)
Synthesis of Compound (1F-63) Using the same method as in Synthesis Example (1), compound (X-63) is used to obtain a compound represented by the formula (1F-63).
HRMS m / z 690.37796 (calcd C ₄₉ H ₄₇ BN ₂ O, 690.3781).

Synthesis example (64)
Synthesis of Compound (1F-64) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-64) can be obtained using the compound (X-64).
HRMS m / z 900.5573 (calcd C ₆₃ H ₇₃ BN ₂ S, 900.5588).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.09-1.16 (m, 18H), 1.25-1.34 (m, 6H), 1.42-1.50 (m, 24H), 1.76-1.86 (m, 4H), 2.19 (s, 3H), 6.03-6.12 (m, 2H), 6.57-6.66 (m, 2H), 7. 01-7.08 (m, 2H), 7.12-7.25 (m, 4H), 7.37-7.44 (m, 2H), 7.48-7.54 (m, 1H), 7.58 (dd, 1H), 7.60-7.67 (m, 1H), 7.67-7.71 (m, 1H), 7.88 (d, 1H), 8.68-8. 72 (m, 1H).

Synthesis example (65)
Synthesis of Compound (1F-65) Using the same method as in Synthesis Example (1), compound (X-65) is used to obtain a compound represented by the formula (1F-65).
HRMS m / z 942.6066 (calcd C ₆₆ H ₇₉ BN ₂ S, 942.6057).
^{1 1} H-NMR (CDCl ₃ ): δ = 0.98-1.02 (m, 9H), 1.09-1.14 (m, 18H), 1.20 (s, 9H), 1.26- 1.34 (m, 6H), 1.39-1.50 (m, 15H), 1.75-1.88 (m, 4H), 6.13-1.35 (m, 2H), 6. 66-6.73 (m, 2H), 7.00-7.07 (m, 2H), 7.12-7.26 (m, 5H), 7.39 (dd, 1H), 7.48- 7.79 (m, 3H), 7.71 (s, 1H), 7.86 (d, 1H), 8.58 (d, 1H).

Synthesis example (66)
Synthesis of Compound (1F-66) Using the same method as in Synthesis Example (1), compound (X-66) is used to obtain a compound represented by the formula (1F-66).
HRMS m / z 844.4941 (calcd C ₅₉ H ₆₅ BN ₂ S, 844.4962).

Synthesis example (67)
Synthesis of Compound (1F-67) Using the same method as in Synthesis Example (1), compound (X-67) is used to obtain a compound represented by the formula (1F-67).
HRMS m / z 858.5131 (calcd C ₆₀ H ₆₇ BN ₂ S, 858.5118).

Synthesis example (68)
Synthesis of Compound (1F-68) Using the same method as in Synthesis Example (1), compound (X-68) is used to obtain a compound represented by the formula (1F-68).
HRMS m / z 990.6077 (calcd C ₇₀ H ₇₉ BN ₂ S, 990.6057).

Synthesis example (69)
Synthesis of Compound (1F-69) Using the same method as in Synthesis Example (1), compound (X-69) is used to obtain a compound represented by the formula (1F-69).
HRMS m / z 912.5562 (calcd C ₆₄ H ₇₃ BN ₂ S, 912.5588).

Synthesis example (70)
Synthesis of Compound (1F-70) Using the same method as in Synthesis Example (1), compound (X-70) is used to obtain a compound represented by the formula (1F-70).
HRMS m / z 714.4166 (calcd C ₄₉ H ₅₅ BN ₂ S, 714.4179).

Synthesis example (71)
Synthesis of Compound (1F-71) Using the same method as in Synthesis Example (1), compound (X-71) is used to obtain a compound represented by the formula (1F-71).
HRMS m / z 768.4659 (calcd C ₅₃ H ₆₁ BN ₂ S, 768.4649).

Synthesis example (72)
Synthesis of Compound (1F-72) Using the same method as in Synthesis Example (1), compound (X-72) is used to obtain a compound represented by the formula (1F-72).
HRMS m / z 810.5130 (calcd C ₅₆ H ₆₇ BN ₂ S, 810.5118).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.01 (s, 9H), 1.27 (s, 3H), 1.29 (s, 3H), 1.36 (s, 9H), 1.45 (S, 3H), 1.46 (s, 9H), 1.49 (s, 3H), 1.51 (s, 9H), 1.81-1.89 (m, 4H), 6.05 ( d, 1H), 6.14 (br, 1H), 6.36 (br, 1H), 6.64 (br, 1H), 6.96 (dd, 1H), 7.19 (dd, 1H), 7.28 (d, 2H), 7.46 (dd, 1H), 7.49 (d, 1H), 7.63 (d, 1H), 7.68 (d, 2H), 7.97 (d) , 1H), 8.76 (s, 1H).

Synthesis example (73)
Synthesis of Compound (1F-73) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-73) can be obtained using the compound (X-73).
HRMS m / z 768.4661 (calcd C ₅₃ H ₆₁ BN ₂ S, 768.4649).

Synthesis example (74)
Synthesis of Compound (1F-74) Using the same method as in Synthesis Example (1), compound (X-74) is used to obtain a compound represented by the formula (1F-74).
HRMS m / z 866.5757 (calcd C ₆₀ H ₇₅ BN ₂ S, 866.5744).

Synthesis example (75)
Synthesis of Compound (1F-75) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-75) can be obtained using the compound (X-75).
HRMS m / z 942.6080 (calcd C ₆₆ H ₇₉ BN ₂ S, 942.6057).

Synthesis example (76)
Synthesis of Compound (1F-76) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-76) can be obtained by using the compound (X-76).
HRMS m / z 900.5599 (calcd C ₆₃ H ₇₃ BN ₂ S, 900.5588).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.10 (s, 9H), 1.11-1.13 (m, 9H), 1.16-1.18 (m, 9H), 1.25- 1.36 (m, 6H), 1.43-1.47 (m, 6H), 1.48 (s, 9H), 1.77-1.87 (m, 4H), 2.22 (s, 3H), 6.07-6.11 (m, 1H), 6.20 (s, 1H), 6.54-6.62 (m, 2H), 6.99-7.08 (m, 2H) , 7.15-7.30 (m, 5H), 7.37 (dd, 1H), 7.46-7.56 (m, 1H), 7.58-7.68 (m, 2H), 7 .69-7.73 (m, 1H), 7.85 (d, 1H), 8.59-8.55 (m, 1H).

Synthesis example (77)
Synthesis of Compound (1F-77) Using the same method as in Synthesis Example (1), compound (X-77) is used to obtain a compound represented by the formula (1F-77).
HRMS m / z 1033.6459 (calcd C ₇₂ H ₈₄ BN ₃ S, 1033.6479).
^{1 1} H-NMR (CDCl ₃ ): δ = 0.97 (s, 9H), 1.10 (s, 9H), 1.27-1.34 (m, 33H), 1.40-1.47 ( m, 6H), 1.75-1.90 (m, 4H), 6.00-6.28 (m, 2H), 6.36 (s, 1H), 6.65-6.80 (m, 6H) 1H), 6.80-6.96 (m, 1H), 7.00 (d, 4H), 7.14 (d, 2H), 7.18-7.26 (m, 5H), 7.38 (D, 1H), 7.43-7.58 (m, 3H), 7.65 (d, 1H), 7.85 (d, 1H), 8.53 (s, 1H).

Synthesis example (78)
Synthesis of Compound (1F-78) Using the same method as in Synthesis Example (5), the compound represented by the formula (1F-78) can be obtained using the compound (X-78).
HRMS m / z 804.5177 (calcd C ₅₇ H ₆₅ BN ₂ O, 804.5190).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.4 (s, 18H), 1.5 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 2.2 (S, 3H), 6.0 (s, 1H), 6.1 (s, 1H), 6.7 (d, 1H), 6.8 (d, 1H), 7.2 (d, 2H) , 7.3 (d, 2H), 7.4 (dd, 1H), 7.5 to 7.6 (m, 2H), 7.6 (t, 1H), 7.7 (d, 2H), 7.9 (d, 1H), 7.9 (d, 1H), 9.3 (d, 1H).

Synthesis example (79)
Synthesis of Compound (1F-79) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-79) can be obtained using the compound (X-79).
HRMS m / z 748.4557 (calcd C ₅₃ H ₅₇ BN ₂ O, 748.4564).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.2 (s, 18H), 1.4 (s, 9H), 1.5 (s, 9H), 2.2 (s, 3H), 5.8 (D, 1H), 6.1 (s, 1H), 6.3 (s, 1H), 6.6 (t, 1H), 6.7 (d, 1H), 7.1 (t, 1H) , 7.3 (d, 2H), 7.4 (d, 2H), 7.4 (d, 1H), 7.5 (m, 2H), 7.6 (d, 1H), 7.7 ( d, 2H), 8.7 (d, 1H), 8.8 (d, 1H).

Synthesis example (80)
Synthesis of Compound (1F-80) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-80) can be obtained using the compound (X-80).
HRMS m / z 822.5133 (calcd C ₅₇ H ₆₇ BN ₂ S, 822.5118).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.04-1.10 (m, 15H), 1.25 (s, 6H), 1.38-1.45 (m, 6H), 1.49 ( s, 9H), 1.53 (s, 6H), 1.66-1.83 (m, 8H), 2.20 (s, 3H), 6.06 (d, 2H), 6.41 (s) , 1H), 6.50 (d, 1H), 7.07 (dd, 1H), 7.26 (d, 1H), 7.38 (dd, 1H), 7.46 (d, 2H), 7 .59 (d, 1H), 7.74 (d, 2H), 7.88 (d, 1H), 8.70 (d, 1H).

Synthesis example (81)
Synthesis of Compound (1F-81) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-81) can be obtained using the compound (X-81).
HRMS m / z 808.4977 (calcd C ₅₆ H ₆₅ BN ₂ S, 808.4962).

Synthesis example (82)
Synthesis of Compound (1F-82) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-82) can be obtained using the compound (X-82).
HRMS m / z 991.6022 (calcd C ₆₉ H ₇₈ BN ₃ S, 991.6010).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.10 (s, 9H), 1.17-1.20 (m, 9H), 1.25-1.38 (m, 33H), 1.42- 1.48 (m, 6H), 1.76-1.88 (m, 4H), 2.19 (s, 3H), 6.02-6.16 (m, 3H), 6.57-6. 62 (m, 2H), 6.86-6.96 (m, 7H), 7.01-7.14 (m, 3H), 7.20 (d, 4H), 7.36 (dd, 1H) , 7.39-7.50 (m, 3H), 7.60-7.67 (m, 1H), 7.83 (d, 1H), 8.47 (d, 1H).

Synthesis example (83)
Synthesis of Compound (1F-83) Using the same method as in Synthesis Example (1), compound (X-83) is used to obtain a compound represented by the formula (1F-83).
HRMS m / z 1123.6961 (calcd C ₇₉ H ₉₀ BN ₃ S, 1123.6949).

Synthesis example (84)
Synthesis of Compound (1F-84) Using the same method as in Synthesis Example (1), compound (X-84) is used to obtain a compound represented by the formula (1F-84).
HRMS m / z 790.4122 (calcd C ₅₄ H ₅₅ BN ₂ OS, 790.4128).

Synthesis example (85)
Synthesis of Compound (1F-85) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-85) can be obtained using the compound (X-85).
HRMS m / z 764.3622 (calcd C ₅₁ H ₄₉ BN ₂ O ₂ S, 764.3608).

Synthesis example (86)
Synthesis of Compound (1F-86) Using the same method as in Synthesis Example (1), compound (X-86) is used to obtain a compound represented by the formula (1F-86).
HRMS m / z 701.3988 (calcd C ₄₇ H ₅₂ BN ₃ S, 701.3975).

Synthesis example (87)
Synthesis of Compound (1F-87) Using the same method as in Synthesis Example (1), compound (X-87) is used to obtain a compound represented by the formula (1F-87).
HRMS m / z 679.3722 (calcd C ₄₇ H ₄₆ BN ₃ O, 679.3734).

Synthesis example (88)
Synthesis of Compound (1F-88) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-88) can be obtained using the compound (X-88).
HRMS m / z 838.4677 (calcd C ₅₉ H ₅₉ BN ₂ O ₂ , 838.4670).

Synthesis example (89)
Synthesis of Compound (1F-89) Using the same method as in Synthesis Example (1), compound (X-89) is used to obtain a compound represented by the formula (1F-89).
HRMS m / z 1061.6022 (calcd C ₇₅ H ₇₆ BN ₃ O ₂ , 1061.6031)

Synthesis example (90)
Synthesis of Compound (1F-90) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-90) can be obtained using the compound (X-90).
HRMS m / z 796.4022 (calcd C ₅₆ H ₅₃ BN ₂ S, 796.4023).

Synthesis example (91)
Synthesis of Compound (1F-91) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-91) can be obtained by using the compound (X-91).
HRMS m / z 886.5422 (calcd C ₆₂ H ₇₁ BN ₂ S, 886.5431).
^{1 1} H-NMR (CDCl ₃ ): δ = 0.99-1.02 (m, 9H), 1.10 (s, 9H), 1.21 (s, 9H), 1.25-1.34 ( m, 6H), 1.38-1.47 (m, 6H), 1.49 (s, 9H), 1.75-1.88 (m, 4H), 6.02-6.45 (m, 2H), 6.62-6.78 (m, 2H), 6.96-7.50 (m, 3H), 7.14-7.29 (m, 5H), 7.38 (dd, 1H) , 7.47-7.73 (m, 4H), 7.85 (d, 1H), 8.58 (d, 1H).

Synthesis example (92)
Synthesis of Compound (1F-92) Using the same method as in Synthesis Example (1), compound (X-92) is used to obtain a compound represented by the formula (1F-92).
HRMS m / z 998.6688 (calcd C ₇₀ H ₈₇ BN ₂ S, 998.6683).
^{1 1} H-NMR (CDCl ₃ ): δ = 0.86-0.90 (m, 18H), 1.02 (s, 9H), 1.10 (s, 9H), 1.27-1.30 ( m, 6H), 1.40-1.50 (m, 24H), 1.76-1.86 (m, 4H), 6.02-6.38 (m, 2H), 6.55-6. 80 (m, 2H), 6.84-90 (m, 2H), 6.93-6.96 (m, 2H), 7.08-7.24 (m, 1H), 7.30-7. 54 (m, 4H), 7.58-773 (m, 2H), 7.86 (d, 1H), 8.61 (s, 1H).

Synthesis example (93)
Synthesis of Compound (1F-93) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-93) can be obtained using the compound (X-93).
HRMS m / z 996.6522 (calcd C ₇₀ H ₈₅ BN ₂ S, 996.6527).
^{1 1} H-NMR (CDCl ₃ ): δ = 0.53-0.60 (m, 6H), 0.99 (s, 9H), 1.04-1.09 (m, 6H), 1.10 ( s, 9H), 1.29 (s, 6H), 1.40-1.58 (m, 28H), 1.86-1.76 (m, 4H), 6.05-6.38 (m, 2H), 6.72 (d, 2H), 6.96-7.04 (m, 2H), 7.06 (d, 1H), 7.14-7.31 (m, 2H), 7.36 -7.55 (m, 3H), 7.56-7.74 (m, 3H), 7.88 (d, 1H), 8.66 (s, 1H).

Synthesis example (94)
Synthesis of Compound (1F-94) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-94) can be obtained using the compound (X-94).
HRMS m / z 982.6922 (calcd C ₇₀ H ₈₇ BN ₂ O, 982.6911).

Synthesis example (95)
Synthesis of Compound (1F-95) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-95) can be obtained by using the compound (X-95).
HRMS m / z 794.5352 (calcd C ₅₆ H ₆₇ BN ₂ O, 794.5346).

Synthesis example (96)
Synthesis of Compound (1F-96) Using the same method as in Synthesis Example (1), compound (X-96) is used to obtain a compound represented by the formula (1F-96).
^{1 1} H-NMR (CDCl ₃ ): δ = 0.9 (s, 9H), 1.3 (s, 9H), 1.5 (s, 9H), 6.3 (d, 1H), 6.5 (D, 1H), 6.6 (d, 1H), 6.9 (m, 3H), 7.1 (m, 1H), 7.1-7.2 (m, 8H), 7.3 ( m, 2H), 7.3 (t, 1H), 7.6 (t, 1H), 7.7 (d2H), 8.0 (d, 1H), 8.3 (d, 1H).

Synthesis example (97)
Synthesis of Compound (1F-97) Using the same method as in Synthesis Example (1), compound (X-97) is used to obtain a compound represented by the formula (1F-97).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.2 (s, 18H), 1.5 (s, 9H), 1.5 (s, 9H), 2.1 (s, 3H), 5.6 (S, 1H), 6.0 (s, 1H), 6.7 (s, 1H), 7.2 to 7.3 (m, 4H), 7.4 (m, 6H), 7.5 ( m, 3H), 7.7 (d, 2H), 8.0 (d, 1H), 8.0 (dd, 1H), 8.9 (m, 2H).

Synthesis example (98)
Synthesis of Compound (1F-98) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-98) can be obtained using the compound (X-98).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.1 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 2.2 (s, 3H), 6.0 (S, 1H), 6.1 (s, 1H), 6.5 (d, 1H), 6.6 (d, 1H), 7.0 (m, 3H), 7.2-7.3 ( m, 3H), 7.4 to 7.5 (m, 4H), 7.6 (dd, 1H), 7.7 (d, 1H), 7.7 (d, 2H), 7.9 (d) , 1H), 8.7 (d, 1H).

Synthesis example (99)
Synthesis of Compound (1F-99) Using the same method as in Synthesis Example (1), compound (X-99) is used to obtain a compound represented by the formula (1F-99).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.2 (s, 9H), 1.4 (s, 9H), 1.4 (s, 9H), 1.5 (s, 9H), 5.7 (D, 1H), 5.8 (d, 1H), 6.1 (d, 1H), 6.7 (d, 1H), 6.9 (m, 7H), 7.1 (m, 9H) , 7.2-7.3 (m, 3H), 7.4 (m, 2H), 7.5 (m, 3H), 7.9 (d, 1H), 8.7
(D, 1H).

Synthesis example (100)
Synthesis of Compound (1F-100) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-100) can be obtained using the compound (X-100).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.4 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 2.2 (S, 3H), 5.8 (d, 1H), 6.0 (s, 1H), 6.2 (s, 1H), 6.6 (d, 1H), 6.9 (dd, 1H) , 7.3 (d, 2H), 7.4 to 7.5 (m, 3H), 7.7 (d, 2H), 7.7 (d, 2H), 8.0 (d, 1H), 8.8 (d, 1H).

Synthesis example (101)
Synthesis of Compound (1F-101) Using the same method as in Synthesis Example (1), a compound represented by the formula (1F-01) can be obtained using compound (X-101).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.1 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 1.9 (T, 6H), 2.1 (d, 6H), 2.2 (s, 3H), 2.2 (m, 3H), 6.0 (s, 1H), 6.1 (s, 1H) , 6.5 (d, 1H), 6.6 (d, 1H), 7.3 (dd, 2H), 7.4 to 7.5 (m, 4H), 7.7 (dd, 2H), 7.7 (dd, 2H), 7.9 (d, 1H), 8.8 (d, 1H).

Synthesis example (102)
Synthesis of Compound (1F-102) Using the same method as in Synthesis Example (1), compound (X-102) is used to obtain a compound represented by the formula (1F-102).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.1 (s, 18H), 1.5 (s, 9H), 1.5 (s, 9H), 1.7 (s, 9H), 2, 2 (S, 3H), 5.9 (d, 1H), 6.1 (s, 1H), 6.3 (s, 1H), 6.6 (t, 1H), 6.7 (d, 1H) , 7.1 (t, 1H), 7.3 (d, 2H), 7.4 (d, 2H), 7.4 to 7.5 (m, 3H), 7.7 (d, 2H), 8.7 (d, 1H), 8.8 (s, 1H).

Synthesis example (103)
Synthesis of Compound (1F-103) Using the same method as in Synthesis Example (1), compound (X-103) is used to obtain a compound represented by the formula (1F-103).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.1 (s, 18H), 1.5 (s, 9H), 1.5 (s, 9H), 2.3 (s, 3H), 6.2 (S, 1H), 6.7 (d, 1H), 6.9 (t, 1H), 7.0 to 7.3 (m, 7H), 7.5 (dd, 1H), 7.7 ( m, 3H), 7.8 (d, 1H), 8.1 (d, 1H), 8.7 (d, 1H), 8.8 (d, 1H).

Synthesis example (104)
Synthesis of Compound (1F-104) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-104) can be obtained by using the compound (X-104).
^{1 1} H-NMR (CDCl ₃ ): δ = 0.99 (s, 9H), 1.11 (s, 9H), 1.30 (s, 6H), 1.43 (s, 3H), 1.46 (M, 12H), 1.51 (s, 9H), 1.78-1.86 (m, 4H), 6.15 (s, 1H), 6.65 (s, 1H), 6.74 ( s, 1H), 7.23-7.29 (d, 4H), 7.41 (d, 1H), 7.46 (d, 1H), 7.53 (s, 1H), 7.66-7 .68 (m, 3H), 7.90 (d, 1H), 8.78 (s, 1H).

Synthesis example (105)
Synthesis of Compound (1F-105) Using the same method as in Synthesis Example (1), compound (X-105) is used to obtain a compound represented by the formula (1F-105).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.11 (s, 9H), 1.19 (s, 9H), 1.26 (s, 3H), 1.28 (s, 3H), 1.37 (S, 18H), 1.44-1.47 (m, 6H), 1.77-1.86 (m, 4H), 2.21 (s, 3H), 6.08 (s, 1H), 6.10 (s, 1H), 6.53 (d, 1H), 6.61 (d, 1H), 7.20 (d, 2H), 7.26 (dd, 1H), 7.31 (dd) , 1H), 7.40 (dd, 1H), 7.48 (d, 1H), 7.61 (t, 1H), 7.66 (d, 1H), 7.88 (d, 1H), 8 .69 (d, 1H).

Synthesis example (106)
Synthesis of Compound (1F-106) Using the same method as in Synthesis Example (1), compound (X-106) is used to obtain a compound represented by the formula (1F-106).
^{1 1} H-NMR (CDCl ₃ ): δ = 0.96-0.99 (m, 9H), 1.10 (s, 9H), 1.12 (s, 9H), 1.25-1.32 ( m, 6H), 1.39-1.51 (m, 24H), 1.76-1.86 (m, 4H), 6.05-6.28 (m, 2H), 6.66-6. 80 (m, 2H), 7.01-7.08 (m, 2H), 7.12-7.24 (m, 4H), 7.37-7.47 (m, 2H), 7.48- 7.69 (m, 3H), 7.70 (s, 1H), 7.88 (d, 1H), 8.70 (s, 1H).

Synthesis example (107)
Synthesis of Compound (1F-107) Using the same method as in Synthesis Example (1), compound (X-107) is used to obtain a compound represented by the formula (1F-107).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.23 (s, 3H), 1.29 (s, 3H), 1.36 (s, 9H), 1.46 (s, 9H), 1.49 (S, 6H), 1.51 (s, 9H), 1.82-1.89 (m, 4H), 2.22 (s, 3H), 5.80 (d, 1H), 5.99 ( s, 1H), 6.24 (s, 1H), 6.56 (d, 1H), 6.92 (d, 1H), 7.20 (dd, 1H), 7.22-7.28 (m) , 2H), 7.44-7.47 (m, 2H), 7.63 (d, 1H), 7.68 (d, 2H), 7.96 (s, 1H), 8.78 (d, 1H).

Synthesis example (108)
Synthesis of Compound (1F-108) Using the same method as in Synthesis Example (1), compound (X-108) is used to obtain a compound represented by the formula (1F-108).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.09 (s, 9H), 1.18 (d, 6H), 1.32 (d, 6H), 1.46 (d, 6H), 1.50 (S, 9H), 1.52 (s, 6H), 1.96 (s, 2H), 2.06 (s, 2H), 2.21 (s, 3H), 6.07 (s, 2H) , 6.25 (s, 1H), 6.51 (s, 1H), 7.08 (d, 1H), 7.17 (dd, 1H), 7.38-7.41 (m, 2H), 7.47 (d, 2H), 7.65 (d, 2H), 7.88 (d, 1H), 8.51 (s, 1H).

Synthesis example (109)
Synthesis of Compound (1F-109) Using the same method as in Synthesis Example (1), compound (X-109) is used to obtain a compound represented by the formula (1F-109).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.11 (s, 9H), 1.18-1.24 (m, 6H), 1.37-1.45 (m, 15H), 1.51 ( s, 9H), 1.71-1.80 (m, 4H), 1.94 (s, 6H), 6.07 (s, 1H), 6.11 (s, 1H), 6.48-6 .55 (m, 2H), 6.97-7.09 (m, 3H), 7.23 (d, 2H), 7.30 (dd, 1H), 7.39-7.43 (m, 2H) ), 7.46 (dd, 1H), 7.57-7.64 (m, 3H), 7.91 (d, 1H), 8.82 (d, 1H).

Synthesis example (110)
Synthesis of Compound (1F-110) Using the same method as in Synthesis Example (1), compound (X-110) is used to obtain a compound represented by the formula (1F-110).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.11 (s, 9H), 1.17-1.24 (m, 15H), 1.32 (s, 18H), 1.37-1.45 ( m, 6H), 1.71-1.80 (m, 4H), 1.97 (s, 6H), 6.11 (s, 1H), 6.14 (s, 1H), 6.52 (dd) , 2H), 6.97-7.09 (m, 3H), 7.18 (d, 2H), 7.28-7.34 (m, 2H), 7.38-7.43 (m, 2H) ), 7.52 (t, 1H), 7.60 (d, 1H), 7.89 (d, 1H), 8.72 (d, 1H).

Synthesis example (111)
Synthesis of Compound (1F-111) Using the same method as in Synthesis Example (1), a compound represented by the formula (1F-111) can be obtained using compound (X-111).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.2 (s, 18H), 1.4 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 2.2 (S, 3H), 5.9 (d, 1H), 6.1 (s, 1H), 6.3 (s, 1H), 6.6 (t, 1H), 6.7 (d, 1H) , 7.1 (t, 1H), 7.3 (d, 2H), 7.4 to 7.5 (m, 3H), 7.5 (m, 2H), 7.6 (d, 2H), 7.7 (d, 2H), 8.1 (d, 2H), 8.9 (d, 1H), 9.1 (s, 1H).

Synthesis example (112)
Synthesis of Compound (1F-112) Using the same method as in Synthesis Example (1), compound (X-112) is used to obtain a compound represented by the formula (1F-112).
HRMS m / z 1067.5977 (calcd C ₇₄ H ₇₈ BN ₃ OS, 1067.5599).

Synthesis example (113)
Synthesis of Compound (1F-113) Using the same method as in Synthesis Example (1), the compound represented by the formula (1F-113) can be obtained using the compound (X-113).
HRMS m / z 1123.6588 (calcd C ₇₈ H ₈₆ BN ₃ OS, 1123.6585).
1 H-NMR (CDCl ₃ ): δ = 0.9 (s, 9H), 1.1 (s, 9H), 1.2 (s, 18H), 1.3 (m, 6H), 1.4 to 1.5 (m, 15H), 1.7 to 1.8 (m, 4H), 6.2 (d, 1H), 6.3 (d, 2H), 6.7 (s, 1H), 6 .8 (d, 1H), 6.9 (q, 8H), 7.2 (dd, 1H), 7.4 (m, 4H), 7.5 (d, 2H), 7.6 (dd, dd, 1H), 7.9 (d, 1H), 7.9 (t, 1H), 8.0 (d, 1H), 8.5 (d, 1H).

Synthesis example (114)
Synthesis of Compound (1F-114) Using the same method as in Synthesis Example (1), compound (X-114) is used to obtain a compound represented by the formula (1F-114).
HRMS m / z 1061,6788 (calcd C ₇₄ H ₈₈ BN ₃ S, 1061.6792)

Synthesis example (115)
Synthesis of Compound (1F-115) Using the same method as in Synthesis Example (1), a compound represented by the formula (1F-115) can be obtained using compound (X-115).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.1 (s, 18H), 1,4 (s, 9H), 1.5 (s, 9H), 1.5 (s, 6H), 2.2 (S, 3H), 6.2 (s, 1H), 6.7 (d, 1H), 7.0 (t, 1H), 7.1 (m, 2H), 7.2 (s, 1H) , 7.3 (d, 2H), 7.3 (d, 2H), 7.4 (d, 1H), 7.6 (dd, 1H), 7.6 (dd, 2H), 7.8 ( d, 2H), 8.7 (d, 1H), 8.8 (s, 1H).

Synthesis example (116)
Synthesis of Compound (1F-116) Using the same method as in Synthesis Example (1), compound (X-116) is used to obtain a compound represented by the formula (1F-116).
HRMS m / z 476.1522 (calcd C ₃₂ H ₂₁ BN ₂ S, 476.1518).

Synthesis example (117)
Synthesis of Compound (1F-117) Using the same method as in Synthesis Example (1), a compound represented by the formula (1F-117) can be obtained using compound (X-117).
^{1 1} H-NMR (CDCl ₃ ): δ = 0.9 (m, 6H), 1.1 (d, 9H), 1.3 to 1.4 (m, 12H), 1.5 (m, 24H) , 1.6 to 1.7 (m, 4H), 1.7 to 1.8 (m, 4H), 2.2 (d, 3H), 6.6 (d, 2H), 6.5 (d) , 1H), 6.6 (t, 1H), 7.0 (d, 1H), 7.1 (d, 1H), 7.1-7.2 (m, 4H), 7.4 (m, 1H), 7.5 (m, 1H), 7.6 (m, 1H), 7.7 (m, 1H), 7.9 (s, 1H), 8.7 (t, 1H).

Synthesis example (118)
Synthesis of Compound (1F-118) Using the same method as in Synthesis Example (1), compound (X-118) is used to obtain a compound represented by the formula (1F-118).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.1 (m, 15H), 1.1 (d, 9H), 1.2 (s, 9H), 1.3 to 1.4 (m, 12H) , 1.4 (s, 3H), 1.5 (s, 12H), 1.6 to 1.7 (m, 4H), 1.7 to 1.9 (m, 4H), 6.2 (brd) , 2H), 6.6 (s, 1H), 6.7 (s, 1H), 7.0 (t, 2H), 7.1-7.2 (m, 5H), 7.5 (d, 1H), 7.6 (d, 1H), 7.7 (t, 1H), 7.7 (s, 1H), 7.9 (s, 1H), 8.6 (d, 1H).

Synthesis example (119)
Synthesis of Compound (1F-119) Using the same method as in Synthesis Example (1), compound (X-119) is used to obtain a compound represented by the formula (1F-119).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.0 (d, 6H), 1.1 (d, 9H), 1.2 (s, 9H), 1.3 to 1.4 (m, 12H) , 1.5 (m, 15H), 1.6 to 1.7 (m, 4H), 1.8 to 1.9 (m, 4H), 2.2 (d, 3H), 6.0 (d) , 1H), 6.2 (s, 1H), 6.5 (d, 1H), 6.6 (dd, 1H), 7.0 (d, 1H), 7.0 (d, 1H), 7 .1 to 7.2 (m, 5H), 7.5 (dd, 1H), 7.6 (dt, 1H), 7.7 (t, 1H), 7.7 (dd, 1H), 7. 8 (d, 1H), 8.6 (dd, 1H).

Synthesis example (119)
Synthesis of Compound (1F-119) Using the same method as in Synthesis Example (1), compound (X-119) is used to obtain a compound represented by the formula (1F-119).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.0 to 1.2 (m, 24H), 1.3 (m, 12H), 1,5 (m, 15H), 1.8 to 1.9 ( m, 4H), 1.9 (s, 2H), 2.2 (s, 3H), 5.9 (d, 1H), 6.2 (s, 1H), 6.2 (s, 1H), 6.6 (d, 1H), 7.0 (d, 1H), 7.0 (d, 1H), 7.1 to 7.3 (m, 5H), 7.5 (dd, 1H), 7 .6 (m, 3H), 7.7 (dd, 1H), 8.6 (dd, 1H).

Synthesis example (120)
Synthesis of Compound (1F-120) Using the same method as in Synthesis Example (1), compound (X-120) is used to obtain a compound represented by the formula (1F-120).
^{1 1} H-NMR (CDCl ₃ ): δ = 1.0 (s, 9H), 1.1 (s, 3H), 1.1 (s, 3H), 1.3 (s, 6H), 1.4 (S, 6H), 1.5 (m, 24H), 1.7 to 1.9 (m, 4H), 1.9 (s, 2H), 6.0 (s, 1H), 6.1 ( Brs, 1H), 6.3 (brs, 1H), 6.6 (s, 1H), 7.2 (dd, 1H), 7.3 (d, 2H), 7.5 (dd, 1H), 7.5 (d, 1H), 7.6 to 7.7 (m, 4H), 8.8 (s, 1H).

By appropriately changing the raw material compound, the other polycyclic aromatic compound of the present invention can be synthesized by a method according to the above-mentioned synthesis example.

Next, in order to explain the present invention in more detail, examples of an organic EL device using the compound of the present invention will be shown, but the present invention is not limited thereto.

<Evaluation of thin-film deposition type organic EL element>
An organic EL element according to Example 1 was produced, and the voltage (V), emission wavelength (nm), and external quantum efficiency (%), which are the characteristics at the time of 1000 cd / m ² emission, were measured, and then 10 mA / cm ² The time for maintaining a brightness of 90% or more of the initial brightness when driven at a constant current with a current density is measured.

The quantum efficiency of the light emitting element includes the internal quantum efficiency and the external quantum efficiency. In the internal quantum efficiency, the external energy injected as electrons (or holes) into the light emitting layer of the light emitting element is converted into pure photons. Shows the ratio. On the other hand, the external quantum efficiency is calculated based on the amount of these photons emitted to the outside of the light emitting element, and a part of the photons generated in the light emitting layer is continuously absorbed or reflected inside the light emitting element. Therefore, the external quantum efficiency is lower than the internal quantum efficiency because it is not emitted to the outside of the light emitting element.

The method for measuring the external quantum efficiency is as follows. Using a voltage / current generator R6144 manufactured by Advantest, the device was made to emit light by applying a voltage at which the brightness of the device was 1000 cd / m ² . The spectral radiance in the visible light region was measured from the direction perpendicular to the light emitting surface using a spectral radiance meter SR-3AR manufactured by TOPCON. Assuming that the light emitting surface is a perfect diffusion surface, the value obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying by π is the number of photons at each wavelength. Next, the number of photons was integrated over the entire observed wavelength region to obtain the total number of photons emitted from the device. The value obtained by dividing the applied current value by the elementary charge is the number of carriers injected into the device, and the value obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency.

The material composition of each layer in the organic EL device according to Examples 1 to 88 and Comparative Examples 1 to 4 is shown in Table 1 below.

In Table 1, "HI" is N ⁴ , N ^4' -diphenyl-N ⁴ , N ^4' -bis (9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl] -4, It is 4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile, and "HT-1" is N- ([1,1'-biphenyl]. ] -4-yl-9,9-dimethyl-N- [4- (9-phenyl-9H-carbazole-3-yl) phenyl) -9H-fluorene-2-amine [1,1'-biphenyl] -4 -Amin, "HT-2" is N, N-bis (4- (dibenzo [b, d] furan-4-yl) phenyl)-[1,1': 4', 1 "-terphenyl] It is -4-amine, "BH-1" is 2- (10-phenylanthracene-9-yl) naphtho [2,3-b] benzofuran, and "BH-2" is 2- (10-phenyl). Anthracene-9-yl) dibenzo [b, d] furan, "BH-3" is 9- ([2,2'-binaphthalene] -7-yl) -10-phenylanthracene, "BH-4" Is 2,7,10,15-tetraphenyldibenzo [g, p] chrysene, and "BH-5" is 2- (dibenzo [g, p] chrysene-2-yl) naphtho [2,3-b]. ] Dibenzofuran, "BH-6" is 5,9-di (naphthalen-2-yl) spiro [benzo [c] fluorene-7,9'-fluorene, "BH-7" is 8- (phenyl) -D5) -1- (10- (phenyl-d5) anthracene-9-yl) dibenzo [b, d] furan, "BH-8" is 2-phenyl-8- (10-phenylanthracene-9-) Il) Dibenzo [b, d] furan, "BH-9" is 4-phenyl-6- (10-phenylanthracene-9-yl) dibenzo [b, d] furan, and "BH-10" is 10-([1,1'-biphenyl] -2-yl) -1,8-diphenylanthracene, and "BH-11" is 2- (4,5-diphenylanthracene-9-yl) -8-phenyl. Dibenzo [b, d] furan, "ET-1" is 4,6,8,10-tetraphenyl [1,4] benzoxabolinino [2,3,4-kl] phenoxabolinine, "ET-2" is 9,9'-(5- (6- (1,1'-biphenyl) -4-yl) -2-phenylpyrimidine-4-yl) -1,3-phenylene. ] Bis (9H-carbazole), and "ET-3" is 2,2'-[(2-phenylanthracene-9,10-diyl) dibenzene-4,1-diyl] dipyridine. The chemical structure is shown below together with "Liq" and "Comparative Compound-1".

A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science, Inc.) obtained by polishing ITO formed to a thickness of 180 nm by sputtering to 150 nm is used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, BH-1, compound (1F-1), ET. A molybdenum vapor deposition boat containing -1 and ET-2, and an aluminum nitride vapor deposition boat containing Liq, LiF and aluminum, respectively, are installed.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 5 × 10 ^-4 Pa, and HI is first heated to be vapor-deposited to a film thickness of 40 nm, and then HAT-CN is heated to be vapor-deposited to a film thickness of 5 nm. Next, HT-1 is heated and vapor-deposited to a film thickness of 45 nm, and then HT-2 is heated and vapor-deposited to a film thickness of 10 nm to form a hole layer consisting of four layers. To do. Next, BH-1 and the compound (1F-1) are simultaneously heated and vapor-deposited to a film thickness of 25 nm to form a light emitting layer. The vapor deposition rate is adjusted so that the mass ratio of BH-1 to the compound (1F-1) is approximately 98: 2. Further, ET-1 is heated and vapor-deposited to a film thickness of 5 nm, and then ET-3 and Liq are simultaneously heated and vapor-deposited to a film thickness of 25 nm to form an electronic layer composed of two layers. Form. The deposition rate is adjusted so that the mass ratio of ET-3 and Liq is approximately 50:50. The deposition rate of each layer is 0.01 to 1 nm / sec. Then, LiF is heated and vapor-deposited to a film thickness of 1 nm at a vapor deposition rate of 0.01 to 0.1 nm / sec, and then aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. Then, the organic EL element of Example 1 is obtained. The same applies to Examples 2 to 69 and Comparative Examples 1 to 4.

A DC voltage is applied with the ITO electrode as the anode and the LiF / aluminum electrode as the cathode, and the characteristics at the time of 1000 cd / m ² emission are measured, and the time for maintaining the brightness of 90% or more of the initial brightness is measured.
The results are shown in Table 2.

<Evaluation of coating type organic EL element>
Next, an organic EL device obtained by coating and forming an organic layer will be described.

<Polymer host compound: Synthesis of SPH-101>
SPH-101 was synthesized according to the method described in WO 2015/008851. A copolymer in which M2 or M3 is bonded is obtained next to M1, and it is estimated from the charging ratio that each unit has a 50:26:24 (molar ratio).

<Polymer hole transport compound: Synthesis of XLP-101>
XLP-101 was synthesized as follows according to the method described in JP-A-2018-61028. A copolymer in which M2 or M3 is bound is obtained next to M7, and it is estimated from the charging ratio that each unit is 40:10:50 (molar ratio). In the following formula, Bpin represents pinacolatoboryl.

<Examples 102 to 110>
A coating solution of the material forming each layer is prepared to prepare a coating type organic EL device.

<Manufacturing of Organic EL Devices of Examples 102 to 104>
Table 3 shows the material composition of each layer in the organic EL device.

The structure of "ET4" in Table 3 is shown below.

<Preparation of composition (1) for forming a light emitting layer>
The composition for forming a light emitting layer (1) is prepared by stirring the following components until a uniform solution is obtained. By spin-coating the prepared composition for forming a light emitting layer on a glass substrate and heating and drying it under reduced pressure, a coating film having no film defects and excellent smoothness can be obtained.
Compound (1F-1) 0.04% by mass
SPH-101 1.96% by mass
Xylene 69.00% by mass
Decalin 29.00% by mass

<PEDOT: PSS solution>
A commercially available PEDOT: PSS solution (Clevios (TM) P VP AI4083, PEDOT: PSS aqueous dispersion, manufactured by Heraeus Holdings) is used.

<Preparation of OTPD solution>
OTPD (LT-N159, manufactured by Luminescence Technology Corp) and IK-2 (photocationic polymerization initiator, manufactured by San Apro) were dissolved in toluene, and the OTPD concentration was 0.7% by mass and the IK-2 concentration was 0.007% by mass. OTPD solution is prepared.

<Preparation of XLP-101 solution>
XLP-101 is dissolved in xylene at a concentration of 0.6% by mass to prepare a 0.7% by mass XLP-101 solution.

<Preparation of PCz solution>
PCz (polyvinylcarbazole) is dissolved in dichlorobenzene to prepare a 0.7% by mass PCz solution.

<Example 102>
A PEDOT: PSS film having a film thickness of 40 nm is formed by spin-coating a PEDOT: PSS solution on a glass substrate on which ITO is deposited to a thickness of 150 nm and firing it on a hot plate at 200 ° C. for 1 hour. (Hole injection layer). Next, the OTPD solution was spin-coated, dried on a hot plate at 80 ° C. for 10 minutes, exposed to an exposure intensity of 100 mJ / cm ² with an exposure machine, and baked on a hot plate at 100 ° C. for 1 hour to obtain the solution. An OTPD film having a film thickness of 30 nm, which is insoluble in, is formed (hole transport layer). Next, the composition for forming a light emitting layer (1) is spin-coated and fired on a hot plate at 120 ° C. for 1 hour to form a light emitting layer having a film thickness of 20 nm.

The produced multilayer film was fixed to a substrate holder of a commercially available thin-film deposition equipment (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing ET1, a molybdenum vapor deposition boat containing LiF, and tungsten containing aluminum Install a vapor deposition boat. After depressurizing the vacuum chamber to 5 × 10 ^-4 Pa, ET1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The vapor deposition rate when forming the electron transport layer is 1 nm / sec. Then, LiF is heated to deposit at a vapor deposition rate of 0.01 to 0.1 nm / sec so as to have a film thickness of 1 nm. Next, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Example 103>
An organic EL device is obtained in the same manner as in Example 102. The hole transport layer is formed by spin-coating an XLP-101 solution and firing it on a hot plate at 200 ° C. for 1 hour to form a film having a film thickness of 30 nm.

<Example 104>
An organic EL device is obtained in the same manner as in Example 102. The hole transport layer is formed by spin-coating a PCz solution and firing it on a hot plate at 120 ° C. for 1 hour to form a film having a film thickness of 30 nm.

<Manufacturing of Organic EL Devices of Examples 105 to 107>
Table 4 shows the material composition of each layer in the organic EL device.

<Preparation of compositions (2) to (4) for forming a light emitting layer>
The composition for forming a light emitting layer (2) is prepared by stirring the following components until a uniform solution is obtained.
Compound (1F-1) 0.02% by mass
mCBP 1.98 mass%
Toluene 98.00% by mass

The composition for forming a light emitting layer (3) is prepared by stirring the following components until a uniform solution is obtained.
Compound (1F-1) 0.02% by mass
SPH-101 1.98% by mass
Xylene 98.00% by mass

The composition for forming a light emitting layer (4) is prepared by stirring the following components until a uniform solution is obtained.
Compound (1F-1) 0.02% by mass
DOBNA 1.98% by mass
Toluene 98.00% by mass

In Table 4, "mCBP" is 3,3'-bis (N-carbazolyl) -1,1'-biphenyl and "DOBNA" is 3,11-di-o-tolyl-5,9-dioxa-13b. -Boranaphtho [3,2,1-de] anthracene, "TSPO1" is a diphenyl [4- (triphenylsilyl) phenyl] phosphine oxide. The chemical structure is shown below.

<Example 105>
An ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) solution is spin-coated on a glass substrate on which ITO is formed to a thickness of 45 nm, and then heated at 50 ° C. for 3 minutes in an air atmosphere, and further at 230 ° C., 15 By heating for a minute, an ND-3202 film having a film thickness of 50 nm is formed (hole injection layer). Next, the XLP-101 solution is spin-coated and heated on a hot plate at 200 ° C. for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film having a film thickness of 20 nm (hole transport layer). Next, the light emitting layer forming composition (2) is spin-coated and heated at 130 ° C. for 10 minutes in a nitrogen gas atmosphere to form a 20 nm light emitting layer.

The produced multilayer film was fixed to a substrate holder of a commercially available thin-film deposition equipment (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing TSPO1, a molybdenum vapor deposition boat containing LiF, and tungsten containing aluminum. Install a vapor deposition boat. After depressurizing the vacuum chamber to 5 × 10 ^-4 Pa, TSPO1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The vapor deposition rate when forming the electron transport layer is 1 nm / sec. Then, LiF is heated to deposit at a vapor deposition rate of 0.01 to 0.1 nm / sec so as to have a film thickness of 1 nm. Next, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Examples 106 and 107>
Using the light emitting layer forming composition (3) or (4), an organic EL device is obtained in the same manner as in Example 5.

<Manufacturing of Organic EL Devices of Examples 108 to 110>
Table 5 shows the material composition of each layer in the organic EL device.

<Preparation of compositions (5) to (7) for forming a light emitting layer>
The composition for forming a light emitting layer (5) is prepared by stirring the following components until a uniform solution is obtained.
Compound (1F-1) 0.02% by mass
2PXZ-TAZ 0.18% by mass
mCBP 1.80% by mass
Toluene 98.00% by mass

The composition for forming a light emitting layer (6) is prepared by stirring the following components until a uniform solution is obtained.
Compound (1F-1) 0.02% by mass
2PXZ-TAZ 0.18% by mass
SPH-101 1.80% by mass
Xylene 98.00% by mass

The composition for forming a light emitting layer (7) is prepared by stirring the following components until a uniform solution is obtained.
Compound (1F-1) 0.02% by mass
2PXZ-TAZ 0.18% by mass
DOBNA 1.80% by mass
Toluene 98.00% by weight

In Table 5, "2PXZ-TAZ" is 10,10'-((4-phenyl-4H-1,2,4-triazole-3,5-diyl) bis (4,1-phenyl)) bis (10H-). Phenoxazine). The chemical structure is shown below.

<Example 108>
An ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) solution is spin-coated on a glass substrate on which ITO is formed to a thickness of 45 nm, and then heated at 50 ° C. for 3 minutes in an air atmosphere, and further at 230 ° C., 15 By heating for a minute, an ND-3202 film having a film thickness of 50 nm is formed (hole injection layer). Next, the XLP-101 solution is spin-coated and heated on a hot plate at 200 ° C. for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film having a film thickness of 20 nm (hole transport layer). Next, the light emitting layer forming composition (5) is spin-coated and heated at 130 ° C. for 10 minutes in a nitrogen gas atmosphere to form a 20 nm light emitting layer.

<Examples 109 and 110>
An organic EL device is obtained in the same manner as in Example 108, except that the host in the light emitting layer forming composition (5) is changed from mCBP to SPH-101 and DOBNA, respectively.

<Example>
<Preparation of composition for forming light emitting layer>
The compositions for forming a light emitting layer according to Examples 201 to 246 and Comparative Example 201 were prepared. The compounds used to prepare the composition are shown below.

<Example 201>
A composition for forming a light emitting layer was prepared by mixing and stirring the following components.
Compound (1-F1) 0.01% by mass
Compound (3-73) 0.99% by mass
Cyclohexylbenzene 70% by mass
3-Phenoxytoluene 30% by mass

<Example 202 to Example 246, Comparative Example 201>
Each composition for forming a light emitting layer was prepared by a method according to Example 201 using the compositions shown in Table 6.

<Evaluation>
The solubility and coatability of the obtained light emitting layer forming compositions according to Examples 201 to 246 and Comparative Example 201 were evaluated.

(Evaluation of solubility)
An example in which all the compounds were dissolved to obtain a uniform solution was defined as "dissolved", and an example in which an insoluble substance remained was defined as "insoluble".

(Evaluation of coatability)
Regarding those that were "dissolved" in the evaluation of the solubility of the prepared ink composition, the film-forming property of the film obtained after spin coating film formation or after inkjet printing was evaluated. After film formation, those with pinholes or precipitation or unevenness were indicated by "defective", and those without pinholes, precipitation and unevenness of compounds were indicated by "good".

<Application method with spin coating>
UV-O3 treatment was performed by irradiating a clean glass substrate having a thickness of 0.5 mm and a size of 28 × 26 mm with an irradiation energy of 1000 mJ / cm ² (low-pressure mercury lamp (254 nanometers)). Then, 0.3 to 0.6 mL of the ink composition was dropped onto the glass, and spin coating (slope, 5 seconds → 500 to 5000 rpm, 10 seconds → slope, 5 seconds) was performed. Further, it was dried on a hot plate at 120 ° C. for 10 minutes.

<Applying method by inkjet>
Regarding the coatability, the film-forming property of the coating film which was discharged into a pixel of 100 ppi and dried at 100 ° C. was evaluated by using an inkjet. The results are summarized in Table 6.

<Viscosity measurement method>
The viscosity was measured using a conical flat plate type rotational viscometer (cone plate type).

<Measurement method of surface tension>
Surface tension was measured using the suspension method.

<Polymer hole transport compound: Synthesis of XLP-101>
XLP-101 was synthesized as follows according to the method described in JP-A-2018-61028. A copolymer in which M5 or M6 is bonded is obtained next to M4, and it is estimated from the charging ratio that each unit has a molar ratio of 40:10:50. In the following formula, Bpin is pinacolatoboryl.

<Manufacturing of Organic EL Devices of Examples 301 to 346 and Comparative Example 301>
Table 7 shows the material composition of each layer in the organic EL device.

The structure of "ET5" in Table 7 is shown below.

<PEDOT: PSS solution>
A commercially available PEDOT: PSS solution (Clevios (TM) P VP AI4083, PEDOT: PSS aqueous dispersion, manufactured by Heraeus Holdings) was used.

<Preparation of OTPD solution>
OTPD (LT-N159, manufactured by Luminescence Technology Corp) and IK-2 (photocationic polymerization initiator, manufactured by San Apro) were dissolved in toluene, and the OTPD concentration was 0.7% by mass and the IK-2 concentration was 0.007% by mass. OTPD solution was prepared.

<Preparation of XLP-101 solution>
XLP-101 was dissolved in xylene at a concentration of 0.6% by mass to prepare a 0.6% by mass XLP-101 solution.

<Preparation of PCz solution>
PCz (polyvinylcarbazole, average molecular weight 1,100,000 g / mol) was dissolved in dichlorobenzene to prepare a 0.7 mass% PCz solution.

<Example 301>
A PEDOT: PSS film having a film thickness of 40 nm was formed by spin-coating a PEDOT: PSS solution on a glass substrate on which ITO was deposited to a thickness of 150 nm and firing it on a hot plate at 200 ° C. for 1 hour. (Hole injection layer). Next, the OTPD solution is spin-coated, dried on a hot plate at 80 ° C. for 10 minutes, exposed to an exposure intensity of 100 mJ / cm ² with an exposure machine, and baked on a hot plate at 100 ° C. for 1 hour to obtain the solution. An OTPD film having a film thickness of 30 nm, which is insoluble in, was formed (hole transport layer). Next, the composition for forming a light emitting layer prepared in Example 201 was spin-coated and fired on a hot plate at 120 ° C. for 1 hour to form a light emitting layer having a film thickness of 20 nm.

The produced multilayer film was fixed to a substrate holder of a commercially available thin-film deposition equipment (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing ET1, a molybdenum vapor deposition boat containing LiF, and tungsten containing aluminum. A boat for vapor deposition was installed. After depressurizing the vacuum chamber to 5 × 10 ^-4 Pa, ET1 was heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The vapor deposition rate when forming the electron transport layer was 1 nm / sec. Then, LiF was heated and deposited at a vapor deposition rate of 0.01 to 0.1 nm / sec so as to have a film thickness of 1 nm. Next, aluminum was heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element was obtained.

<Example 302> to <Example 346> and <Comparative Example 301>
An organic EL device was produced in the same procedure as in Example 301 except that the light emitting layer forming composition prepared in each of the examples shown in Table 7 was used instead of the light emitting layer forming composition prepared in Example 301. did.

The polycyclic aromatic compound of the present invention is useful as a material for organic devices, particularly as a material for a light emitting layer for forming a light emitting layer of an organic electroluminescent element. By using the compound of the present invention in the light emitting layer, it is possible to provide an organic EL device having high efficiency and long life.

100 Organic electroluminescent element 101 substrate 102 anode 103 hole injection layer 104 hole transport layer 105 light emitting layer 106 electron transport layer 107 electron injection layer 108 cathode 110 substrate 120 electrode 130 coating film 140 coating film 150 light emitting layer 200 bank 300 inkjet head 310 Ink droplets

Claims

A multimer of a polycyclic aromatic compound represented by the following formula (1) or a polycyclic aromatic compound having a plurality of structures represented by the following formula (1).

(In equation (1),
Rings A, B, and C are independently aryl rings or heteroaryl rings, and at least one hydrogen in these rings may be substituted, provided that rings A, B, and C are substituted. At least one ring selected from the group consisting of is a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring. At least one hydrogen in this fused ring may be substituted.
Rings B and C may be attached via a single bond or a linking group.
Y 1 is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is aryl, alkyl, or Cycloalkyl,
X 1 and X 2 are independently>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the above-mentioned> N-R. R is hydrogen, optionally substituted aryl (except amino as a substituent), optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. Yes, the R of> Si (-R) 2 is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or substituted. The R of> C (-R) 2 may be an independently hydrogen, an aryl which may be substituted, a heteroaryl which may be substituted, an alkyl which may be substituted, and the like. Alternatively, it is a cycloalkyl which may be substituted, and the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring, and the above> N R in at least one of -R,> Si (-R) 2 , and> C (-R) 2 is bonded to at least one ring of the A ring, B ring, and C ring by a linking group or a single bond. May be
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by the formula (1) may be condensed with at least one cycloalkane, and at least one in the cycloalkane. Hydrogen may be substituted and at least one -CH 2- in the cycloalkane may be substituted with -O-.
At least one hydrogen in the compound or structure represented by the formula (1) may be substituted with deuterium, cyano, or halogen. )
At least one ring selected from the group consisting of A ring, B ring and C ring is a fused ring which is a heteroaryl ring containing a sulfur atom or an oxygen atom, and at least one hydrogen in this fused ring is substituted. May,
The polycyclic aromatic compound according to claim 1 or a multimer thereof.
The polycyclic aromatic compound or a multimer thereof according to claim 1 or 2, wherein at least one ring selected from the group consisting of A ring, B ring and C ring is a ring represented by the formula (BHet).

(In the formula (BHet), R a1 to R a6 are hydrogens or substituents, except that any two or three of R a1 to R a6 adjacent to each other are Y 1 and Y 1 in the formula (1). It becomes a bond with X 1 and / or X 2, and X is>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above> The Rs of NR,> Si (-R) 2 , or> C (-R) 2 are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, substituted, respectively. It is an alkyl which may be an alkyl or a cycloalkyl which may be substituted, and the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring. Good.)
At least one ring selected from the group consisting of the B ring and the C ring is a ring represented by the formula (BHet).
In the formula (BHet), any two adjacent R a1 to R a6 serve as a bond with Y 1 and X 1 or X 2 in the formula (1).
Others Ra1 to Ra6 are hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl hetero. Arylamino, substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted. Alkoxy, substituted or unsubstituted aryloxy, or substituted silyl,
In the ring A and the rings B and C that are not fused rings, the substituents in which the hydrogen of the aryl ring or the heteroaryl ring may be substituted are substituted or unsubstituted aryl, substituted or unsubstituted hetero. Aryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino, substituted or unsubstituted diarylboryl (two aryls via a single bond or a linking group). One selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, and substituted silyl. That's it,
Rings A, B, and C all include a 5- or 6-membered ring that shares a bond with the central condensed 2-ring structure of formula (1) composed of Y 1 , X 1 , and X 2 .
Rings B and C may be bonded via a single bond,>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S or> Se, as described above. > N-R and> Si (-R) 2 R may be independently substituted with hydrogen, alkyl or cycloalkyl, or heteroaryl, alkyl or cycloalkyl, respectively. Alkyl or cycloalkyl, wherein the> C (-R) 2 R may be substituted with hydrogen, alkyl or cycloalkyl, or heteroaryl, alkyl or cycloalkyl. It is cycloalkyl, and the R in at least one of>N-R,> Si (-R) 2 and> C (-R) 2 is -O-, -S-, -C (-R). It may be bonded to at least one ring of the B ring and the C ring by a 2- or a single bond, and the R of the -C (-R) 2- is hydrogen, alkyl, or cycloalkyl, and the said. The two Rs> Si (-R) 2 and> C (-R) 2 may be combined with each other to form a ring.
X 1 and X 2 are independently>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the above-mentioned> N-R. And> Si (-R) 2 R may be independently substituted with an aryl, alkyl or cycloalkyl optionally substituted with hydrogen, alkyl or cycloalkyl, heteroaryl, alkyl, or cyclo, respectively. The R of> C (-R) 2 is alkyl, optionally substituted with hydrogen, alkyl or cycloalkyl, and optionally substituted with aryl, alkyl or cycloalkyl, heteroaryl, alkyl, or cycloalkyl. The two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring, and the above-mentioned> N-R and> Si (-R) may be formed. ) 2 and> R in at least one of C (-R) 2 are -O-, -S-, -C (-R) 2- , or by a single bond, the A ring, B ring, and C. It may be attached to at least one ring of the ring, wherein the -C (-R) 2- R is hydrogen, alkyl, or cycloalkyl.
In the case of a multimer, it is a dimer or trimer having two or three structures represented by the formula (1).
The polycyclic aromatic compound according to claim 3 or a multimer thereof.
The polycyclic aromatic compound or a multimer thereof according to claim 3 or 4, which comprises at least one tertiary-alkyl represented by the following formula (tR).

(In the formula (tR), Ra , R b, and R c are independently alkyl having 1 to 24 carbon atoms, and any -CH 2- in the alkyl may be substituted with -O-. , * Is the connection position.)
X 1 and X 2 are both> N-R, at least one of R may be substituted 2- biphenylyl or optionally substituted terphenyl of> N-R in X 1 and X 2 - The polycyclic aromatic compound or a multimer thereof according to any one of claims 3 to 5, which is 2'-yl.
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by the formula (1) is condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane is The polycyclic aromatic compound according to any one of claims 3 to 6, which may be substituted, and at least one -CH 2- in the cycloalkane may be substituted with -O-. Multimer.
The polycyclic aromatic compound according to claim 1 or 2, which is represented by the following formulas (2), (3), (4), (5), (6), (7), (8), or (9). Group compounds or their multimers.

(In equations (2), (3), (4), (5), (6), (7), (8), and (9),
R 1 to R 17 , R 21 to R 24 , R 31 to R 34 , and R 41 to R 44 are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino, respectively. , Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyls, in which at least one hydrogen is aryl, heteroaryl may be substituted by alkyl or cycloalkyl, or together with a ring adjacent groups are bonded to one of R 1 ~ R 3, is adjacent groups of R 8 ~ R 11 Adjacent groups of R 4 to R 7 are bonded to each other together with the b ring to bond with the c ring, and adjacent groups of R 12 to R 14 are bonded to each other with the a12 ring to form R 15 to. Adjacent groups of R 17 are bonded to each other with the b15 ring, and adjacent groups of R 21 to R 24 are bonded to each other with the c21 ring, and adjacent groups of R 31 to R 34 are bonded to each other. They may be combined to form an aryl ring or a heteroaryl ring, respectively, with the b31 ring and with the adjacent groups of R 41 to R 44 bonded together with the b41 ring, at least in the formed ring. One hydrogen can be aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl. , Alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen in these is aryl, heteroaryl, alkyl, or. May be substituted with cycloalkyl
However, in the formula (2), at least one set of two adjacent groups of R 1 to R 11 are combined to form a divalent group represented by the formula (Het). R 4 and R 5 and R 6 and R 7 do not simultaneously constitute a divalent group represented by the formula (Het), and R 8 and R 9 and R 10 and R 11 simultaneously formulate. It does not constitute a divalent group represented by (Het), and in the formula (7), at least one set of two adjacent groups of R 1 to R 3 and R 9 to R 17 Is combined to form a divalent group represented by the formula (Het).
In formula (Het), R b1 and R b2 are hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are attached via a single bond or a linking group). Can be), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, where * is. Represents the bond position
X is independently>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above-mentioned>N-R,> Si ( -R) 2, or> C (-R) 2 of R each independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, wherein> Si (-R) 2, and> C (-R ) The two Rs of 2 may be combined with each other to form a ring.
R 7 and R 8 in formula (2), R 8 and R 24 in formula (3), or R 34 and R 24 in formula (5) are combined to form a single bond,>O,>NR,>. Si (-R) 2 ,> C (-R) 2 ,> S, or> Se may be set, and the R of> N-R and> Si (-R) 2 may be independent of each other. Hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the R of> C (-R) 2 is , Hydrogen, aryl with 6 to 12 carbons, heteroaryl with 2 to 15 carbons, alkyl with 1 to 6 carbons, or cycloalkyl with 3 to 14 carbons, said> Si (-R) 2 , and. The two Rs of> C (-R) 2 may be combined with each other to form a ring, and at least one of the above-mentioned>N-R,> Si (-R) 2 and> C (-R) 2 . R in one is bonded to at least one of the b ring, b31 ring, c ring, and c21 ring by an -O-, -S-, -C (-R) 2- , or a single bond. Well,
Y 1 is independently B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is Aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms.
X 1 , X 2 , X 3 , and X 4 are independent of>O,>NR,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, respectively. Yes, the R of> N-R and> Si (-R) 2 are independently hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, and 2 to 2 carbon atoms which may be substituted. 15 heteroaryl, optionally substituted alkyl having 1 to 6 carbon atoms, or optionally substituted cycloalkyl having 3 to 14 carbon atoms, wherein R of> C (-R) 2 is hydrogen. , An aryl having 6 to 12 carbon atoms which may be substituted, a heteroaryl which may have 2 to 15 carbon atoms which may be substituted, an alkyl having 1 to 6 carbon atoms which may be substituted, or an alkyl having 1 to 6 carbon atoms which may be substituted. It is a good cycloalkyl having 3 to 14 carbon atoms, and the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring, and the above> R in at least one of NR,> Si (-R) 2 , and> C (-R) 2 is by -O-, -S-, -C (-R) 2- , or a single bond. It may be bonded to at least one ring of a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, a 5-membered ring, a b31 ring, and a b41 ring.
Selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9). At least one of them may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 30 carbon atoms and 2 to 30 carbon atoms. Heteroaryl, alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms may be substituted, and at least one -CH 2- in the cycloalkane may be substituted with -O-. Often,
At least one hydrogen in the compound represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9) is deuterium, cyano,. Alternatively, it may be replaced with halogen. )
R 1 to R 17 , R 21 to R 24 , R 31 to R 34 , and R 41 to R 44 are independently hydrogen, aryl having 6 to 30 carbon atoms, and heteroaryl having 2 to 30 carbon atoms, respectively. Diarylamino (where aryls are aryls with 6-12 carbon atoms), diarylboryls (where aryls are aryls with 6-12 carbon atoms and the two aryls may be attached via a single bond or a linking group). , alkyl having 1 to 24 carbon atoms, cycloalkyl or trialkylsilyl (wherein the alkyl is an alkyl of 1 to 6 carbon atoms) having 3 to 24 carbon atoms is also adjacent groups of R 1 ~ R 3 together Are bonded together with the a ring, adjacent groups of R 8 to R 11 are bonded to each other with the b ring, and adjacent groups of R 4 to R 7 are bonded to each other with the c ring, and the R 12 Adjacent groups of R 14 are bonded to each other with the a12 ring, and adjacent groups of R 15 to R 17 are bonded to each other with the b15 ring, and adjacent groups of R 21 to R 24 are bonded to each other. Are bonded together with the c21 ring, adjacent groups of R 31 to R 34 are bonded to each other to form the b31 ring, and adjacent groups of R 41 to R 44 are bonded to each other together with the b41 ring, respectively. An aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms may be formed, and at least one hydrogen in the formed ring is an aryl ring having 6 to 10 carbon atoms and 1 to 12 carbon atoms. Alkyl, cycloalkyl with 3 to 16 carbon atoms or trialkylsilyl (where alkyl is alkyl with 1 to 4 carbon atoms) may be substituted.
In the formula (Het), R b1 and R b2 are hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diallylamino (where aryl is an aryl having 6 to 12 carbon atoms), and a diallylboryl (whereever Aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or It is a trialkylsilyl (although alkyl is an alkyl having 1 to 6 carbon atoms).
X is independently>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above-mentioned>N-R,> Si ( -R) 2 or> C (-R) 2 R is an aryl with 6 to 30 carbon atoms, a heteroaryl with 2 to 30 carbon atoms, an alkyl with 1 to 24 carbon atoms, or a cycloalkyl with 3 to 24 carbon atoms. And
R 7 and R 8 or R 15 and R 16 may be combined to form>O,>N-R,> C (-R) 2 , or> S, as described above> N-R. Is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and R of> C (-R) 2 is hydrogen and an aryl having 6 to 10 carbon atoms. , An alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
Y 1 is B, P, P = O, P = S, or Si-R, and R of the Si-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a carbon number of carbon atoms. 5-10 cycloalkyl,
X 1 , X 2 , X 3 and X 4 are independently>O,>N-R,> C (-R) 2 , or> S, and R in> N-R is replaced. Aryl having 6 to 10 carbon atoms which may be substituted, alkyl having 1 to 4 carbon atoms which may be substituted, or cycloalkyl having 5 to 10 carbon atoms which may be substituted, and the above-mentioned> C (-. R) 2 R is a hydrogen, an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
Selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), and (9). At least one of the compounds may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 16 carbon atoms and 2 to 22 carbon atoms. Heteroaryl, alkyl having 1-12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms may be substituted.
At least one hydrogen in the compound represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9) is deuterium, cyano,. The polycyclic aromatic compound according to claim 8, which may be substituted with halogen, or a multimer thereof.
The polycyclic aromatic compound or a multimer thereof according to claim 8 or 9, which comprises at least one tertiary-alkyl represented by the following formula (tR).

(In the formula (tR), Ra , R b, and R c are independently alkyl having 1 to 24 carbon atoms, and any -CH 2- in the alkyl may be substituted with -O-. , * Is the connection position.)
X 1 and X 2 in equations (2), (3), (4), (5), and (6) and X 1 , X 2 , X 3 in equations (7), (8), and (9). And X 4 are both> N-R and R may be substituted 2-biphenylyl or optionally substituted terphenyl-2'-as X 1 , X 2 , X 3 or X 4. The polycyclic aromatic compound or a multimer thereof according to any one of claims 8 to 10, which comprises at least one of yl> NR.
Selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9). At least one of the compounds is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2- in the cycloalkane is -O-. The polycyclic aromatic compound or a multimer thereof according to any one of claims 8 to 11, which may be substituted.
The polycyclic aromatic compound according to claim 1 or 2, or a multimer thereof, wherein at least one ring selected from the group consisting of A ring, B ring, and C ring is a ring represented by the formula (DBHet). ..

(In the formula (DBHet), R a11 to R a18 are hydrogens or substituents, except that any two or three of R a11 to R a18 adjacent to each other are Y 1 and Y 1 in the formula (1). It becomes a bond with X 1 and / or X 2, and X is>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above> R of NR,> Si (-R) 2 , or> C (-R) 2 is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, Alternatively, it is a cycloalkyl which may be substituted, and the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring.)
B at least one ring is selected from the group consisting of ring and C ring is a ring represented by the formula (DBHet), one of R a11 ~ R a18, two or adjacent the formula (1) Becomes a bond with Y 1 and X 1 or X 2
In formula (DBHet), other R a11 ~ R a18 is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted di-heteroarylamino, Substituent or unsubstituted aryl heteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted. Cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl.
The substituents of the aryl ring or the heteroaryl ring in the ring A and the rings B and C which are not the fused rings may be substituted or unsubstituted aryl, substituted or unsubstituted hetero. Aryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino, substituted or unsubstituted diarylboryl (two aryls via a single bond or a linking group). One selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, and substituted silyl. That's it,
Rings A, B, and C all include a 5- or 6-membered ring that shares a bond with the central condensed 2-ring structure of formula (1) composed of Y 1 , X 1 , and X 2 .
Rings B and C may be bonded via a single bond,>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se. The> N-R and> Si (-R) 2 R may be independently substituted with aryl, alkyl or cycloalkyl optionally substituted with hydrogen, alkyl or cycloalkyl, respectively. , Alkyl, or cycloalkyl, wherein R of> C (-R) 2 is aryl, which may be substituted with hydrogen, alkyl or cycloalkyl, or heteroaryl, which may be substituted with alkyl or cycloalkyl. It is alkyl or cycloalkyl, and the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring, and the above> NR, The R in at least one of> Si (-R) 2 and> C (-R) 2 is -O-, -S-, -C (-R) 2- , or the B ring and C by a single bond. It may be attached to at least one ring of the ring, wherein the -C (-R) 2- R is hydrogen, alkyl, or cycloalkyl.
X 1 and X 2 are independently>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the above-mentioned> N-R. And> Si (-R) 2 R may be independently substituted with an aryl, alkyl or cycloalkyl optionally substituted with hydrogen, alkyl or cycloalkyl, heteroaryl, alkyl, or cyclo, respectively. The R of> C (-R) 2 is alkyl, optionally substituted with hydrogen, alkyl or cycloalkyl, and optionally substituted with aryl, alkyl or cycloalkyl, heteroaryl, alkyl, or cycloalkyl. The two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring, and the above-mentioned> N-R and> Si (-R) may be formed. ) 2 and> R in at least one of C (-R) 2 are -O-, -S-, -C (-R) 2- , or by a single bond, the A ring, B ring, and C. It may be attached to at least one ring of the ring, wherein the -C (-R) 2- R is hydrogen, alkyl, or cycloalkyl.
In the case of a multimer, it is a dimer or trimer having two or three structures represented by the formula (1).
The polycyclic aromatic compound according to claim 13 or a multimer thereof.
The polycyclic aromatic compound or a multimer thereof according to claim 13 or 14, which comprises at least one tertiary-alkyl represented by the following formula (tR).

(In the formula (tR), Ra , R b, and R c are independently alkyl having 1 to 24 carbon atoms, and any -CH 2- in the alkyl may be substituted with -O-. , * Is the connection position.)
X 1 and X 2 are both> N-R, at least one of R may be substituted 2- biphenylyl or optionally substituted terphenyl of> N-R in X 1 and X 2 - The polycyclic aromatic compound or a multimer thereof according to any one of claims 13 to 15, which is 2'-yl.
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by the formula (1) is condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane is The polycyclic aromatic compound according to any one of claims 13 to 16, which may be substituted, and at least one -CH 2- in the cycloalkane may be substituted with -O-. Multimer.
The polycyclic aromatic compound according to claim 1 or 2, represented by the following formulas (12), (13), (14), (15), (16), (17), (18), or (19). Group compounds or their multimers.

(In equations (12), (13), (14), (15), (16), (17), (18), (19), and (20),
R 1 ~ R 3 and R 8 ~ R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, Jiariruboriru (two aryl is a single bond or a linking group (May be bonded via), alkyl, alkoxy, aryloxy, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen is aryl, heteroaryl, May be substituted with alkyl or cycloalkyl,
R 51 to R 58 and R 61 to R 68 are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded or linking groups). (May be bonded via), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Often,
Adjacent groups of R 1 to R 3 are bonded to each other to form a ring, and adjacent groups of R 8 to R 11 are bonded to each other to form a ring b, which are adjacent to each other of R 51 to R 54. The groups are bonded together with the c51 ring, the adjacent groups of R 55 to R 58 are bonded together with the c55 ring, and the adjacent groups of R 61 to R 64 are bonded together with the b61 ring. And adjacent groups of R 65 to R 68 may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b65 ring, respectively, and at least one hydrogen in the formed ring is an aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diallylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or It may be substituted with a substituted silyl,
X is independently>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above-mentioned>N-R,> Si ( -R) 2 or> C (-R) 2 R are independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, respectively, and> Si (-R) 2 and> C (-R). The two Rs of 2 may be combined with each other to form a ring.
Y 1 is independently B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is It is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.
X 1 and X 2 are independently>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the above-mentioned> N-R. And> R of Si (-R) 2 are independently hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, a heteroaryl having 2 to 15 carbon atoms which may be substituted, respectively. It is an alkyl having 1 to 6 carbon atoms which may be present, or a cycloalkyl having 3 to 14 carbon atoms which may be substituted, and R of> C (−R) 2 may be hydrogen or substituted. An aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted, an alkyl having 1 to 6 carbon atoms which may be substituted, or an alkyl having 3 to 14 carbon atoms which may be substituted. It is a cycloalkyl, and the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring, and the above>N-R,> Si ( The R in at least one of -R) 2 and> C (-R) 2 is -O-, -S-, -C (-R) 2- or by a single bond, a ring, b ring, c51 ring, And may be associated with at least one ring of the b61 ring.
From aryl and heteroaryl rings in compounds represented by formulas (12), (13), (14), (15), (16), (17), (18), (19), or (20). At least one selected from the group may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl or carbon having 6 to 30 carbon atoms. It may be substituted with a heteroaryl of number 2 to 30, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH 2- in the cycloalkane is substituted with -O-. May have been
At least one hydrogen in the compounds represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19), and (20) is deuterium. It may be substituted with hydrogen, cyano, or halogen. )
R 1 ~ R 3 and R 8 ~ R 11 are each independently hydrogen, aryl of 6 to 30 carbon atoms, heteroaryl of 2-30 carbon atoms, diarylamino (where aryl is an aryl having 6 to 12 carbon atoms ), Diarylboryl (where aryls are aryls with 6-12 carbon atoms and the two aryls may be attached via a single bond or a linking group), or alkyls with 1-24 carbon atoms.
R 51 to R 58 and R 61 to R 68 are independently hydrogen, aryl with 6 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, and diarylamino (where aryl is aryl with 6 to 12 carbon atoms). ), Diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, and 3 to 24 carbon atoms. Twenty-four cycloalkyls, or trialkylsilyls (where alkyls are alkyls with 1-6 carbon atoms).
Adjacent groups of R 1 to R 3 are bonded to each other to form a ring, and adjacent groups of R 8 to R 11 are bonded to each other to form a ring b, which are adjacent to each other of R 51 to R 54. The groups are bonded together with the c51 ring, the adjacent groups of R 55 to R 58 are bonded together with the c55 ring, and the adjacent groups of R 61 to R 64 are bonded together with the b61 ring. and adjacent groups together with binding to b65 ring of R 65 ~ R 68, respectively, may form a heteroaryl ring of aryl or C 6-15 carbon atoms 9-16, formed At least one hydrogen in the ring is aryl with 6 to 10 carbon atoms, alkyl with 1 to 12 carbon atoms, or cycloalkyl or trialkylsilyl with 3 to 16 carbon atoms (where alkyl is alkyl with 1 to 4 carbon atoms). ) May be replaced
X is independently>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above-mentioned>N-R,> Si ( -R) 2 or> C (-R) 2 R is an aryl with 6 to 30 carbon atoms, a heteroaryl with 2 to 30 carbon atoms, an alkyl with 1 to 24 carbon atoms, or a cycloalkyl with 3 to 24 carbon atoms. And
Y 1 is B, P, P = O, P = S or Si-R, and R of the Si-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or 5 carbon atoms. ~ 10 cycloalkyl,
X 1 and X 2 are independently>O,>N-R,> C (-R) 2 , or> S, where R in> N-R may be substituted carbon. Aryl of number 6 to 10, alkyl having 1 to 4 carbon atoms which may be substituted, or cycloalkyl having 5 to 10 carbon atoms which may be substituted, and R of> C (-R) 2 is , Hydrogen, aryl with 6 to 10 carbon atoms, alkyl with 1 to 4 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms.
From aryl and heteroaryl rings in compounds represented by formulas (12), (13), (14), (15), (16), (17), (18), (19), and (20). At least one selected from the group may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl or carbon having 6 to 16 carbon atoms. It may be substituted with a heteroaryl of number 2 to 22, an alkyl of 1 to 12 carbons, or a cycloalkyl of 3 to 16 carbons.
At least one hydrogen in the compound represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19), or (20) is deuterium. The polycyclic aromatic compound or a multimer thereof according to claim 18, which may be substituted with hydrogen, cyano, or halogen.
The polycyclic aromatic compound or a multimer thereof according to claim 18 or 19, which comprises at least one tertiary-alkyl represented by the following formula (tR).

(In the formula (tR), Ra , R b, and R c are independently alkyl having 1 to 24 carbon atoms, and any -CH 2- in the alkyl may be substituted with -O-. , * Is the connection position.)
X 1 and X 2 are both> N-R, at least one of R may be substituted 2- biphenylyl or optionally substituted terphenyl of> N-R in X 1 and X 2 - The polycyclic aromatic compound or a multimer thereof according to any one of claims 18 to 20, which is 2'-yl.
Selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by the formulas (12), (13), (14), (15), (16), (17), (18), or (19). At least one of the compounds is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2- in the cycloalkane is -O-. The polycyclic aromatic compound or a multimer thereof according to any one of claims 18 to 21, which may be substituted.
The polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 7 and 13 to 17, wherein the A ring is a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring.
The polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 23, wherein Y 1 is B.
The polycyclic aromatic according to any one of claims 1 to 24, wherein R comprises at least one group of> NR as X 1 , X 2 , X 3 or X 4. A compound or a multimer thereof.

(Me indicates methyl, tBu indicates t-butyl, * indicates the binding position.)
The polycyclic aromatic compound according to any one of claims 1 to 25, or a multimer thereof, wherein the halogen is fluorine.
The polycyclic aromatic compound according to claim 1 or a multimer thereof, which is represented by any of the following structural formulas.

(In the above structural formula, "D" indicates deuterium, "Me" indicates methyl, "tBu" indicates t-butyl, and "tAm" indicates t-amyl.)
The polycyclic aromatic compound according to claim 1 or a multimer thereof, which is represented by any of the following structural formulas.

(In the above structural formula, "Me" indicates methyl and "tBu" indicates t-butyl.)
The polycyclic aromatic compound according to claim 1 or a multimer thereof, which is represented by any of the following structural formulas.
A reactive compound in which a reactive substituent is substituted on the polycyclic aromatic compound according to any one of claims 1 to 29 or a multimer thereof.
A polymer compound obtained by polymerizing the reactive compound according to claim 30 as a monomer, or a polymer crosslinked product obtained by further cross-linking the polymer compound.
A pendant type polymer compound in which the main chain type polymer is substituted with the reactive compound according to claim 30, or a pendant type polymer crosslinked product in which the pendant type polymer compound is further crosslinked.
A material for an organic device containing the polycyclic aromatic compound according to any one of claims 1 to 29 or a multimer thereof.
A material for an organic device containing the reactive compound according to claim 30.
A material for an organic device containing the polymer compound or polymer crosslinked product according to claim 34.
A material for an organic device containing the pendant type polymer compound or the pendant type polymer crosslinked body according to claim 32.
The material for an organic device according to any one of claims 33 to 36, wherein the material for the organic device is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.
The material for an organic device according to claim 37, wherein the material for the organic electroluminescent element is a material for a light emitting layer.
A composition containing the polycyclic aromatic compound according to any one of claims 1 to 32 or a multimer thereof, and an organic solvent.
A composition containing the reactive compound according to claim 30 and an organic solvent.
A composition containing a main chain polymer, the reactive compound according to claim 33, and an organic solvent.
A composition containing the polymer compound or polymer crosslinked product according to claim 31 and an organic solvent.
A composition containing the pendant-type polymer compound or the pendant-type polymer crosslinked product according to claim 32 and an organic solvent.
The polycyclic aromatic compound according to any one of claims 1 to 29 or a polymer thereof, which is arranged between the pair of electrodes composed of an anode and a cathode and the pair of electrodes, and the reactivity according to claim 30. An organic electroluminescent element having a compound, the polymer compound or polymer crosslinked body according to claim 31, or an organic layer containing the pendant type polymer compound or pendant type polymer crosslinked body according to claim 32. ..
The polycyclic aromatic compound according to any one of claims 1 to 29 or a polymer thereof, which is arranged between the pair of electrodes composed of an anode and a cathode and the pair of electrodes, and the reactivity according to claim 30. An organic electroluminescent element having a compound, a polymer compound or a polymer crosslinked product according to claim 31, or a light emitting layer containing the pendant type polymer compound or the pendant type polymer crosslinked product according to claim 32. ..
The light emitting layer contains a host and the polycyclic aromatic compound as a dopant, a multimer thereof, a reactive compound, a polymer compound, a polymer crosslinked product, a pendant type polymer compound or a pendant type polymer crosslinked product. The organic electroluminescent element according to claim 45.
The organic electroluminescent element according to claim 46, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound.
It has an electron transporting layer and / or an electron injecting layer arranged between the cathode and the light emitting layer, and at least one of the electron transporting layer and the electron injecting layer is a borane derivative, a pyridine derivative, a fluorentene derivative, or BO. Consists of system derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives and azoline derivatives. The organic electric field light emitting element according to any one of claims 45 to 47, which comprises at least one selected from the group.
The electron transporting layer and / or electron injecting layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, and an alkaline earth metal. Claim that it contains at least one selected from the group consisting of halides, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals. 48. The organic electric field light emitting element.
At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer is a polymer compound obtained by polymerizing a low molecular compound capable of forming each layer as a monomer, or , A polymer crosslinked product obtained by further cross-linking the polymer compound, or a pendant type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain type polymer, or the pendant type polymer compound. The organic electroluminescent element according to any one of claims 44 to 49, which comprises a pendant type polymer crosslinked body further crosslinked.
A display device or a lighting device provided with the organic electroluminescent element according to any one of claims 44 to 50.
A reaction step of metallation halogen atom (Hal) between X 1 and X 2 in the following intermediates -1 using an organic alkali compound,
Halides Y 1, amination halides Y 1, a reaction step of exchanging said metal and Y 1 using a reagent selected from the group consisting of aryloxy compound of alkoxides and Y 1 of Y 1,
And a reaction step of coupling the B ring and C ring by the Y 1 by successive electrophilic aromatic substitution using a Bronsted base, multi formula (1) according to claim 1 A method for producing a multimer of a ring aromatic compound or a polycyclic aromatic compound having a plurality of structures represented by the formula (1).
The production method according to claim 52, wherein the reaction is promoted by further adding Lewis acid.
The polycyclic aromatic compound represented by the formula (1) according to claim 1 or a polycyclic having a plurality of structures represented by the formula (1), which comprises a reaction step of allowing an acid to act on the intermediate-2 below. A method for producing a multimer of an aromatic compound.

(In Intermediate-2, Z is —B (OH) 2 which may be esterified.)