KR20130097784A - Organic electroluminescent element and charge-transporting material - Google Patents

Abstract

Provided is an organic electroluminescent device having a low driving voltage, excellent durability, small efficiency drop during high-brightness driving, small chromaticity change, and small fluctuation in device characteristics due to a change in dope concentration.
An organic electroluminescent element which has at least one organic layer containing a light emitting layer between electrodes, and contains the compound represented by General formula (1) in at least one organic layer.
R ₀ each independently represents an aryl group consisting of only an alkyl group or a monocyclic ring. m is an integer of 0-4, n shows the integer of 1-4. Moreover, the connection form of phenylene groups is all meta or para, and when n = 1, all three phenylene groups are connected by para.
R _A , R _B and R _C independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting only of a single ring, a silyl group, a cyano group, a halogen atom, or a group obtained by combining these.
a1 and b1 represent the integer of 0-4 independently. c1 represents the integer of 0-3 independently.

Description

Organic electroluminescent device and charge transport material {ORGANIC ELECTROLUMINESCENT ELEMENT AND CHARGE-TRANSPORTING MATERIAL}

The present invention relates to organic electroluminescent devices and charge transport materials.

Organic electroluminescent elements (hereinafter also referred to as "elements" and "organic EL elements") have been actively researched and developed because high-luminance light emission is obtained by low voltage driving. An organic electroluminescent element has an organic layer between a pair of electrodes, the electron injected from the cathode and the hole injected from the anode recombine in an organic layer, and use the energy of the excitons produced | generated for light emission.

In recent years, the use of phosphorescent materials, such as an iridium complex and a platinum complex, is increasing the efficiency of the device. Moreover, the dope type element which uses the light emitting layer which doped the light emitting material in the host material is employ | adopted widely.

Development of charge transport materials contained in host materials and other organic layers used in light emitting layers is also being actively carried out.

For example, Patent Documents 1 and 2 disclose an organic electroluminescent device using a compound having a plurality of triphenylene structures.

Japanese Unexamined Patent Publication No. 2008-543086 Japanese Unexamined Patent Publication No. 2002-329580

The organic electroluminescent device using a compound having a plurality of triphenylene structures as described in the above Patent Documents 1 and 2 also has a further improvement in driving voltage and durability, and a decrease in efficiency and high chromaticity change during high brightness driving. Further improvement is desired about the thing, the thing with small fluctuation | variation of the element characteristic by the change of dope density | concentration, etc.

An object of the present invention is to provide an organic electroluminescent device having a low driving voltage, excellent durability, low efficiency in high-brightness driving, small chromaticity change, and small fluctuation in device characteristics due to a change in dope concentration.

Another object of the present invention is to provide a compound and a charge transport material which can be provided to the organic electroluminescent device.

That is, this invention can be achieved by the following means.

An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode on a <1> substrate and at least one organic layer including a light emitting layer between the electrodes, the organic electroluminescent device comprising at least one of the at least one organic layer. The organic electroluminescent element containing the compound represented by following General formula (1).

[Formula 1]

(In General formula (1), R <_0> represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently, n represents the integer of 1-4. Moreover, phenylene groups Are all meta or para, and when n = 1 all three phenylene groups are linked by para.

R _A , R _B and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a halogen atom, or a group obtained by combining these. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different.

a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3 each independently.)

The organic electroluminescent element as described in said <1> whose compound represented by <2> above-mentioned general formula (1) is a compound represented by any of the following general formulas (2)-(4).

(2)

(In General Formula (2)-(4), R represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently.)

<3> R ₀ is an organic electroluminescent element described in alkyl group, or the general formula (2) ~ R is an alkyl group of the <1> according to any one of (4) or <2> in the general formula (1).

The organic electroluminescent element as described in said <1> or <2> whose m is 0 in any one of <4> General Formula (1)-(4).

The organic electroluminescent element as described in any one of said <1>-<4> whose molecular weight of the compound represented by any of <5> General Formula (1)-(4) is 1000 or less.

The organic electroluminescent element as described in any one of said <1>-<5> containing at least 1 sort (s) of phosphorescent light emitting material in a <6> light emitting layer.

The organic electroluminescent element as described in said <5> in which a <7> said phosphorescence emitting material is represented with the following general formula (E-1).

(3)

(In General Formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.

A ₁ represents a group of atoms which together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms.

B ₁ represents an atomic group which forms a 5 or 6 membered ring together with Z ² and a carbon atom.

(X-Y) represents a monoanionic bidentate ligand.

n _E1 represents an integer of 1 to 3.)

The organic electroluminescent element as described in said <7> in which the phosphorescence emitting material represented by <8> said general formula (E-1) is represented with the following general formula (E-2).

[Formula 4]

(In General Formula (E-2), A ^E1 to A ^E8 each independently represent a nitrogen atom or CR ^E.

R ^E represents a hydrogen atom or a substituent.

(X-Y) represents a monoanionic bidentate ligand.

n _E2 represents an integer of 1 to 3.)

The organic electroluminescent element as described in said <7> or <8> whose maximum light emission wavelength of the phosphorescence emitting material represented by <9> said general formula (E-1) is 500 nm-700 nm.

The organic electroluminescent element as described in any one of said <1>-<9> which contains the compound represented by <10> said general formula (1) in a light emitting layer.

The organic electroluminescent element as described in any one of said <1>-<10> which contains the compound represented by <11> the said General formula (1) between the said light emitting layer and the said cathode, and is contained in the positive hole block layer adjacent to the said light emitting layer. .

<12> The light-emitting device containing the organic electroluminescent element in any one of said <1>-<11>.

The display apparatus containing the organic electroluminescent element in any one of <13> said <1>-<11>.

The lighting apparatus containing the organic electroluminescent element in any one of <14> said <1>-<11>.

Charge transport material containing the compound represented by <15> General formula (1).

[Chemical Formula 5]

(In General formula (1), R <_0> represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently, n represents the integer of 1-4. Moreover, phenylene groups Are all meta or para, and when n = 1 all three phenylene groups are linked by para.

R _A , R _B and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a halogen atom, or a group obtained by combining these. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different.

a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3 each independently.)

Charge transport material which consists of a compound represented by any of <16> following General Formula (2)-(4).

[Formula 6]

(In General Formula (2)-(4), R represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently.)

<17> A compound represented by General Formula (1).

[Formula 7]

(In General formula (1), R <_0> represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently, n represents the integer of 1-4. Moreover, phenylene groups Are all meta or para, and when n = 1 all three phenylene groups are linked by para.

R _A , R _B and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a halogen atom, or a group obtained by combining these. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different.

a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3 each independently.)

<18> A compound represented by any one of the following General Formulas (2) to (4).

[Formula 8]

(In General Formula (2)-(4), R represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently.)

By using the compound represented by General formula (1) in this invention, a drive voltage is low, it is excellent in durability, the efficiency fall at the time of a high brightness drive, the chromaticity change is small, and the fluctuation | variation of the element characteristic by a dope density change is small. An organic electroluminescent device can be provided. The small efficiency reduction and chromaticity change at the time of high brightness drive are important for the use which requires use at high brightness, such as illumination. In addition, if the variation in device characteristics is small with respect to the change in dope concentration, there is an advantage in that nonuniformity during device fabrication is less likely to occur, and the yield is improved. Moreover, according to this invention, the compound and charge transport material which can be provided to the said organic electroluminescent element can be provided.

The compound represented by the general formula (1) has a wider π-conjugated system, and thus has a high charge injection / transportability, high stability for charges and excitons, and a large T ₁ energy. It is estimated that the above-mentioned effect is obtained because the balance of? Is good, the charge balance is not disturbed well, and partial concentration does not easily occur.

The wider π conjugated system has advantages such as improved charge injection / transportability and improved stability to charges and excitons, but too wider the T ₁ energy, resulting in lower efficiency and lower durability when used in phosphorescent devices. do.

 By using the structure represented by the general formula (1), it is possible to achieve a state in which the π conjugated system is moderately widened, and changes in device characteristics with respect to the dope concentration change, which are small in efficiency reduction and chromaticity change during low driving voltage, high durability, and high luminance driving. The material which shows the outstanding characteristic, such as being small, is obtained. As a mechanism of decreasing the efficiency reduction and chromaticity change at the time of high brightness driving and decreasing the element characteristic change with respect to the dope density change when used for a light emitting layer, by using the compound represented by General formula (1) to a host, It is considered that the injection and transport properties of electrons and holes in the light emitting layer are both good, and the charge balance is not disturbed well, and the charges or excitons are not accumulated at the interface of the organic layer.

1 is a schematic view showing an example of the configuration of an organic electroluminescence device according to the present invention.
2 is a schematic view showing an example of a light-emitting device related to the present invention.
3 is a schematic view showing an example of a lighting apparatus according to the present invention.

In the present invention, substituent groups A and B are defined as follows.

(Substituent group A)

Alkyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C10, For example, methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl , n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like.), alkenyl group (preferably C 2 to 30, more preferably C 2 to 20, particularly preferably C 2 to 10 And vinyl, allyl, 2-butenyl, 3-pentenyl, and the like, for example.), An alkynyl group (preferably C 2 to 30, more preferably C 2 to 20, particularly preferably C2-C10, for example, propargyl, 3-pentynyl, etc.), an aryl group (preferably C6-C30, More preferably, C6-C20, Especially preferably, C1-C10 6-12, For example, phenyl, p-methylphenyl, naphthyl, anthracenyl, etc. are mentioned. ), An amino group (preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, for example, amino, methylamino, dimethylamino, diethylamino, dibenzyl) Amino, diphenylamino, ditolylamino, etc.), an alkoxy group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C10, For example, Methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.), an aryloxy group (preferably C6-C30, More preferably, C6-C20, Especially preferably, C6-C6 Phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc.), heterocyclic oxy group (preferably C1-C30, More preferably, it is C1-C20 Especially preferably, it is C1-C12, for example Ridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), an acyl group (preferably C2-C30, more preferably C2-C20, Especially preferably, C2-C12 And acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably C2-C30, more preferably C2-C20, Especially preferably, C2-C) 12, for example, methoxycarbonyl, ethoxycarbonyl, etc.), an aryloxycarbonyl group (preferably C7 to 30, more preferably C7 to 20, particularly preferably C7 Phenyloxycarbonyl, etc.), an acyloxy group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example acetoxy, benzoyl And an acylamino group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, acetylamino, benzoylamino, etc. are mentioned. ), An alkoxycarbonylamino group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C12, For example, a methoxycarbonylamino etc. are mentioned. .), An aryloxycarbonylamino group (preferably C7-30, More preferably, it is C7-20, Especially preferably, it is C7-12, For example, phenyloxycarbonylamino etc. are mentioned. ), A sulfonylamino group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, methanesulfonylamino, benzenesulfonylamino, etc. are mentioned. Sulfamoyl group (preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, for example, sulfamoyl, methyl sulfamoyl, dimethyl sulfamoyl, and phenyl). Sulfamoyl, etc.), carbamoyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, carbamoyl, methylcarbo, Barmoyl, diethylcarbamoyl, phenylcarbamoyl, etc.), alkylthio group (preferably C1-C30, More preferably, C1-C20, Especially preferably, C1-C12 And methylthio, ethylthio, etc.) and an arylthio group (preferably C6-C30, More preferably, it is C6-C20, Especially preferably, it is C6-C12, Example Phenylthio etc. can be mentioned.), Hete Ring thio group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, pyridylthio, 2-benzimizolylthio, 2-benzoxazolyl Thio, 2-benzthiazolylthio, etc.), sulfonyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, mesyl , Tosyl, etc.), sulfinyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, methanesulfinyl, benzenesulfinyl Etc.), a ureide group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, fluoride, methyl ureide, phenyl Ureide, etc.), phosphate amide group (bar Preferably it is C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, diethyl phosphate amide, a phenyl phosphate amide, etc. are mentioned.), A hydroxyl group, Mercapto group, halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, Heterocyclic group (The aromatic heterocyclic group is also included, Preferably it is C1-C30, More preferably, it is C1-C12, As a hetero atom, For example, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom) , Selenium atom, tellurium atom, and pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl , Quinolyl, Reel, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzooxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group , Azepinyl group, sirolyl group, etc.), silyl group (preferably C3-C40, more preferably C3-C30, especially preferably C3-C24, for example trimethylsilyl , Triphenylsilyl, etc.), silyloxy group (preferably C3-C40, More preferably, it is C3-C30, Especially preferably, it is C3-C24, For example, trimethylsilyloxy, Triphenylsilyloxy, etc.) and a phosphoryl group (For example, a diphenylphosphoryl group, a dimethylphosphoryl group, etc. are mentioned.). These substituents may further be substituted and group selected from the substituent group A demonstrated above as an additional substituent is mentioned. Moreover, the substituent substituted by the substituent may further be substituted and group selected from the substituent group A demonstrated above as further substituent is mentioned. Moreover, the substituent substituted by the substituent substituted by the substituent may further be substituted, and as further substituent, group chosen from the substituent group A demonstrated above is mentioned.

(Substituent group B)

Alkyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C10, For example, methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl , n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like.), alkenyl group (preferably C 2 to 30, more preferably C 2 to 20, particularly preferably C 2 to 10 And vinyl, allyl, 2-butenyl, 3-pentenyl, and the like, for example.), An alkynyl group (preferably C 2 to 30, more preferably C 2 to 20, particularly preferably C2-C10, for example, propargyl, 3-pentynyl, etc.), an aryl group (preferably C6-C30, More preferably, C6-C20, Especially preferably, C1-C10 6-12, For example, phenyl, p-methylphenyl, naphthyl, anthranyl, etc. are mentioned. C), cyano group, heterocyclic group (aromatic heterocyclic group is also included, and preferably has 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and as a hetero atom, for example, nitrogen atom, oxygen atom, sulfur Atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, Isoxazolyl, Isothiazolyl, Quinolyl, Furyl, Thienyl, Selenophenyl, Telurophenyl, Piperidyl, Piperidino, Morpholino, Pyrrolidyl, Pyrrolidino, Benzooxazolyl, Benzoimide Dazolyl, benzothiazolyl, carbazolyl group, azepinyl group, sirolyl group, and the like.) These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group B. Moreover, the substituent substituted by the substituent may further be substituted and group chosen from the substituent group B demonstrated above as an additional substituent is mentioned. Moreover, the substituent substituted by the substituent substituted by the substituent may further be substituted and the group selected from the substituent group B demonstrated above as a further substituent is mentioned.

An organic electroluminescent device of the present invention is an organic electroluminescent device having a pair of electrodes comprising an anode and a cathode on a substrate, and at least one organic layer including a light emitting layer between the electrodes, wherein at least one of the organic layers is present. It contains the compound represented by following General formula (1).

[Chemical Formula 9]

(In General formula (1), R <_0> represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently, n represents the integer of 1-4. Moreover, phenylenes The linking form of is all meta or para, and when n = 1 all three phenylenes are linked by para.

R _A , R _B and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a halogen atom, or a group obtained by combining these. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different.

a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3 each independently.)

The alkyl group as R ₀ may be linear, branched or cyclic, and examples thereof include alkyl groups in the substituent group A described above, and generally have 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms. More preferably, it is a C1-C10, More preferably, it is a C1-C6, Most preferably, it is a C1-C4 alkyl group. For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, 1, 1-dimethylpropyl group, 2-methylpentyl group, n-hexyl group, cyclohexyl group, methylpentyl group, dimethylbutyl group, etc. are mentioned, A methyl group, an ethyl group, n-propyl group, n-butyl group, or t -Butyl group is more preferable, More preferably, it is either a methyl group or t-butyl group, Most preferably, it is a methyl group.

The alkyl group as R ₀ may have substituents, such as the substituent illustrated as substituent group A.

An aryl group consisting of only a single ring as R _{0 means} a phenyl group or a monovalent substituent in which a plurality of phenylenes are linked by a single bond (the number of benzene rings linked by a single bond is preferably 3 or less, more preferably 1 or 2). It represents and a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a queen phenyl group, etc. are mentioned, for example. Among these, any of a phenyl group, a biphenyl group, and a terphenyl group (particularly 3,5-diphenylphenyl) is preferable, any one of a phenyl group and a biphenyl group is more preferable, and a phenyl group is most preferable.

The aryl group as R ₀ may have substituents such as the substituents exemplified as the substituent group A, and the substituent is particularly preferably an alkyl group.

When the alkyl group is substituted with an aryl group, the preferred range is the same as in the case of the alkyl group as R ₀ described above.

4 or less are preferable from a viewpoint of chemical stability, as for the sum total of m in General formula (1), 2 or less are more preferable, It is especially preferable that it is 0.

R ₀ is preferably an alkyl group from the viewpoint of chemical stability.

It is preferable that n is 1 or more and 3 or less, and 1 or 2 is especially preferable. That is, in general formula (1), as a phenylene structure which connects the triphenylene structure of both ends, terphenyl structure (group in which three phenylenes were connected) or quarterphenyl structure (group in which four phenylenes were connected) It is especially preferable to form.

In particular, in general formula (1), when n is 1 and becomes a p-terphenyl structure (a group in which all three phenylenes are bonded at the para position), or n is 2, and m-quaterphenyl structure ( It is preferred if the four phenylenes are all groups bonded at the meta position.

In addition, in the case of having a structure of p-quaterphenyl as the phenylene structure in the general formula (1), since the T ₁ energy is smaller than that of the green phosphorescent material, the red phosphorescent device material is more than the green phosphorescent material. It is preferable to use. In the case of having a structure of p-quaterphenyl (p-quaterphenyl, p-quinkyphenyl, p-sexyphenyl, etc.) FIG. ₀ also has one or more alkyl groups as R ₀ , and the T ₁ energy is larger than that of the green phosphor. It can use suitably as a material for them.

R _A , R _B and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a halogen atom, or a group obtained by combining these.

As an alkyl group, Preferably it is C1-C10, More preferably, it is a C1-C6, More preferably, it is a C1-C4 alkyl group, A methyl group, an ethyl group, n-propyl group, n-butyl group, or t- Butyl groups are preferred.

As a cycloalkyl group, Preferably it is a C3-C10, More preferably, it is a C4-6, C5 or 6 cycloalkyl group, A cyclopentyl group or a cyclohexyl group is preferable.

As an aryl group which consists only of a ring, a phenyl group is preferable.

As a heteroaryl group which consists only of a monocyclic ring, the heteroaryl group which consists only of nitrogen-containing or sulfur-containing monocyclic groups is preferable, A pyridyl group, a pyrazyl group, a pyrimidyl group, or a thiophenyl group is more preferable, A pyridyl group or a pyrimidyl group is more preferable.

As a silyl group, Preferably it is C3-C40, More preferably, it is C3-C30, Especially preferably, it is C3-C24, A trimethylsilyl group and a triphenylsilyl group are especially preferable.

R _A , R _B , and R _C are preferably an aryl group consisting of only an alkyl group and a monocyclic ring, a silyl group, and a cyano group, more preferably an aryl group consisting of only an alkyl group and a monocyclic ring, and still more preferably an aryl consisting of only a single ring. Qi.

In General Formula (1), a1 and b1 respectively independently represent the integer of 0-4. In order for charge transport property and the synthesis | combination to be easy, the integer of 0-2 is preferable, as a1 and b1, 0 or 1 is more preferable, and 0 is still more preferable.

In general formula (1), c1 represents the integer of 0-3. In order to facilitate charge transport and synthesis, an integer of 0 to 2 is preferable, as c1, 0 or 1 is more preferable, and 0 is more preferable.

In particular, the compound in which the compound represented by the said General formula (1) is represented by either of following General formula (2)-(4) is preferable.

[Formula 10]

(In General Formulas (2) to (4), each R independently represents an aryl group consisting of only an alkyl group or a monocyclic ring which may have an alkyl group. M each independently represents an integer of 0 to 4).

It is preferable that m = 0.

It is preferable that R is an alkyl group.

The aryl group which consists only of the monocyclic which may have the alkyl group or alkyl group as R is the same as that in R <_0> in General formula (1).

In a compound represented by the general formula (1), film state T ₁ energy, 2.39 eV (55 ㎉ / ㏖ ) more than 3.25 eV (75 ㎉ / ㏖) is preferably, 2.47 eV (57.0 ㎉ / ㏖ ) more than 3.04 or less It is more preferable that it is eV (70 dl / mol) or less, and it is still more preferable that it is 2.52 eV (58.0 dl / mol) or more and 2.82 eV (65 dl / mol) or less. In particular, in the case of using a phosphorescent light emitting material as the light emitting material, it is preferable that the T ₁ energy falls within the above range.

T ₁ energy can be obtained from the short wavelength end by measuring the phosphorescence emission spectrum of the thin film of the material. For example, on the cleaned quartz glass substrate, a material is formed into a film thickness of about 50 nm by the vacuum vapor deposition method, and the phosphorescence emission spectrum of a thin film is F-7000 Hitachi spectrophotometer (Hitachi High Technologies) under liquid nitrogen temperature. Measure with). The T ₁ energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.

It is preferable that the molecular weight of the compound represented by General formula (1) is 1200 or less, It is more preferable that it is 1000 or less, It is more preferable that it is 680 or more and 1000 or less, It is especially preferable that it is 680 or more and 900 or less, It is most preferable that it is 680 or more and 850 or less. . By making molecular weight into this range, the film | membrane quality is favorable and the material excellent in sublimation purification and vapor deposition aptitude is obtained.

It is preferable to use the compound represented by General formula (1) for a light emitting layer, a hole block layer, an electron block layer, It is more preferable to use for a light emitting layer, a hole block layer, It is still more preferable to use for a light emitting layer.

From the viewpoint of operating the organic electroluminescent device stably with respect to heat generation during high temperature driving or driving the device, the glass transition temperature (Tg) of the compound represented by the general formula (1) is preferably 80 ° C or more and 400 ° C or less, and 100 ° C or more. It is more preferable that it is 400 degrees C or less, and it is still more preferable that they are 120 degreeC or more and 400 degrees C or less.

Although the specific example of a compound represented by General formula (1) is shown below, it is not limited to these.

[Formula 11]

[Chemical Formula 12]

[Chemical Formula 13]

[Formula 14]

[Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

The compound represented by the said General formula (1) is a method as described in Unexamined-Japanese-Patent No. 2004-43349, Unexamined-Japanese-Patent No. 2004-83481, US 2006/0280965, WO 2009/021107, Unexamined-Japanese-Patent No. 2009-114068, etc. In addition, it can synthesize | combining other well-known reaction.

After synthesis, purification by column chromatography, recrystallization or the like is preferably followed by purification by sublimation purification. Sublimation purification not only separates organic impurities, but also effectively removes inorganic salts, residual solvents, and the like.

The compound represented by General formula (1) may be contained in any organic layer between the cathode and the anode of an organic electroluminescent element. It is preferable that the compound represented by General formula (1) is contained in the light emitting layer or the organic layer between a light emitting layer and a cathode, and adjacent to a light emitting layer.

 As an organic layer which may contain the compound represented by General formula (1), a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge block layer (hole block layer, an electron block layer, etc.) etc. These are mentioned, Preferably it is any of a light emitting layer, an exciton block layer, a charge block layer, an electron carrying layer, an electron injection layer, More preferably, it is a light emitting layer, an exciton block layer, a charge block layer, or an electron carrying layer, More preferably, Is a light emitting layer or a hole block layer.

When contained in a light emitting layer, the compound represented by General formula (1) is contained 0.1-99 mass% with respect to the total mass of a light emitting layer, It is more preferable that 1-95 mass% is contained, It is 10-95 mass% More preferably included.

 When the compound represented by General formula (1) is contained in organic layers other than a light emitting layer, it is preferable to contain 70-100 mass% with respect to the total mass of the organic layer, and it is more preferable that 85-100 mass% is contained.

[Charge Transport Material Represented by General Formula (1)]

This invention relates also to the charge transport material represented by the said General formula (1).

The compound and charge transport material represented by the general formula (1) of the present invention can be suitably used for organic electronic devices such as electrophotographic, organic transistors, organic photoelectric conversion devices (energy conversion applications, sensor applications, etc.) and organic electroluminescent devices. It is possible to use it for an organic electroluminescent element, and it is especially preferable.

 The range with preferable charge transport material represented by General formula (1) is as above-mentioned.

[Composition containing a compound represented by General Formula (1)]

This invention relates also to the composition containing the compound represented by General formula (1). In this composition, it is preferable that content of the compound represented by General formula (1) is 30-99 mass% with respect to the total solid in a composition, It is more preferable that it is 50-97 mass%, It is 70-96 mass% More preferred. As another component which may be contained in the composition of this invention, an organic substance may be sufficient as an organic substance, and the material illustrated as a host material mentioned below, a fluorescent luminescent material, a phosphorescent luminescent material, and a hydrocarbon material can be applied as an organic substance. And a host material, a phosphorescent material, and a hydrocarbon material.

The composition can form the organic layer of an organic electroluminescent element by dry film forming methods, such as a vapor deposition method and a sputtering method, and a wet film forming method, such as a transfer method and a printing method.

[Thin Film Containing Compound Represented by General Formula (1)]

This invention relates also to the thin film containing the compound represented by General formula (1). The thin film can be formed by a wet film forming method such as a dry film forming method such as a vapor deposition method or a sputtering method, a transfer method, or a printing method using the composition. The film thickness of the thin film may be any thickness depending on the application, preferably 0.1 nm to 1 mm, more preferably 0.5 nm to 1 μm, still more preferably 1 nm to 200 nm, and particularly preferably 1 Nm to 100 nm.

[Organic electroluminescent device]

The organic electroluminescent element of this invention is demonstrated in detail.

An organic electroluminescent device of the present invention is an organic electroluminescent device having a pair of electrodes composed of an anode and a cathode on a substrate, and at least one organic layer including a light emitting layer between the electrodes, wherein the organic layer of the at least one layer The compound represented by General formula (1) of this invention is included in at least one layer of any. It is preferable that at least one of the anode and the cathode which are a pair of electrodes is transparent or translucent on the property of a light emitting element.

In addition to the light emitting layer, a hole injection layer, a hole transport layer, a block layer (hole block layer, exciton block layer, etc.), an electron transport layer, etc. are mentioned as an organic layer. Two or more layers of these organic layers may be formed, respectively, and when forming two or more layers, they may be formed with the same material, and may be formed with a different material for every layer.

It is preferable that the organic electroluminescent element of this invention contains at least 1 sort (s) of phosphorescent light emitting material in the said light emitting layer.

An example of a structure of the organic electroluminescent element which concerns on FIG. 1 at this invention is shown. The organic electroluminescent element 10 of FIG. 1 has an organic layer including the light emitting layer 6 between a pair of electrodes (anode 3 and the cathode 9) on the board | substrate 2. As the organic layer, the hole injection layer 4, the hole transport layer 5, the light emitting layer 6, the hole block layer 7 and the electron transport layer 8 are laminated in this order from the anode side 3.

<Configuration of Organic Layer>

There is no restriction | limiting in particular as a laminated constitution of the said organic layer, Although it can select suitably according to the use and the objective of an organic electroluminescent element, What is formed on the said transparent electrode or the said semi-transparent electrode is preferable. In this case, the organic layer is formed on the front surface or one surface of the transparent electrode or the translucent electrode electrode.

There is no restriction | limiting in particular about the shape, size, thickness, etc. of an organic layer, According to the objective, it can select suitably.

Although the following is mentioned as a specific laminated constitution, This invention is not limited to these constitutions.

Anode / hole transporting layer / light emitting layer / electron transporting layer / cathode,

Anode / hole transporting layer / light emitting layer / block layer / electron transporting layer / cathode,

Anode / hole transporting layer / light emitting layer / block layer / electron transporting layer / electron injection layer / cathode,

Anode / hole injection layer / hole transport layer / light emitting layer / hole block layer / electron transport layer / cathode,

Anode / hole injecting layer / hole transporting layer / light emitting layer / electron transporting layer / electron injecting layer / cathode,

Anode / hole injection layer / hole transport layer / light emitting layer / hole block layer / electron transport layer / electron injection layer / cathode.

About the element structure of a organic electroluminescent element, a board | substrate, a cathode, and an anode, it is described in detail in Unexamined-Japanese-Patent No. 2008-270736, for example, and the matter of the publication can be applied to this invention.

<Substrate>

It is preferable that it is a board | substrate which does not scatter or attenuate the light emitted from an organic layer as a board | substrate used by this invention. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.

<Anode>

The anode may have a function as an electrode which normally supplies holes to an organic layer, and there is no restriction | limiting in particular about the shape, structure, size, etc., According to the use and the objective of a light emitting element, it can select suitably from well-known electrode materials. As mentioned above, the anode is usually formed as a transparent anode.

<Cathode>

The cathode may have a function as an electrode which injects electrons into an organic layer normally, and there is no restriction | limiting in particular about the shape, structure, size, etc., According to the use and the objective of a light emitting element, it can select suitably from well-known electrode materials.

<Organic layer>

The organic layer in this invention is demonstrated.

(Formation of Organic Layer)

In the organic electroluminescent device of the present invention, each organic layer is preferably formed by any one of dry coating methods such as vapor deposition and sputtering, solution coating such as transfer, printing, spin coating, and bar coating. Can be. It is preferable that at least 1 layer of an organic layer is formed by the solution coating method, and it is more preferable that the layer containing the compound represented by the said General formula (1) is formed by the solution coating method.

(Light emitting layer)

The light emitting layer has a function of receiving holes from an anode, a hole injection layer or a hole transport layer when receiving an electric field, receiving electrons from a cathode, an electron injection layer or an electron transport layer, and providing a place for recombination of holes and electrons to emit light. to be. It is preferable that the light emitting layer in the organic electroluminescent element of this invention contains at least 1 sort (s) of phosphorescent material.

(Luminescent material)

As the light emitting material in the present invention, any of a phosphorescent light emitting material and a fluorescent light emitting material can be used.

The light emitting layer in this invention can contain two or more types of light emitting materials in order to improve color purity and to widen a light emission wavelength range. It is preferable that at least one of the light emitting materials is a phosphorescent light emitting material.

In the present invention, in addition to at least one phosphorescent light emitting material contained in the light emitting layer, as the light emitting material, a phosphorescent light emitting material different from the phosphorescent light emitting material contained in the light emitting layer can be used.

For these fluorescent light emitting materials and phosphorescent light emitting materials, for example, paragraphs [0100] to [0164] of JP 2008-270736, and paragraph numbers of JP 2007-266458 to [0088] to [0090] The details of these publications can be applied to the present invention as described in detail in the following.

Phosphorescent light emitting materials that can be used in the present invention include, for example, US 6303238 B1, US 6097147, WO 00/57676, WO 00/70655, WO 01/08230, WO 01/39234 A2, WO 01/41512 A1, WO 02/02714 A2, WO 02/15645 A1, WO 02/44189 A1, WO 05/19373 A2, JP 2001-247859, JP 2002-302671, JP 2002-117978 Japanese Unexamined Patent Publication No. 2003-133074, Japanese Unexamined Patent Publication No. 2002-235076, Japanese Unexamined Patent Publication No. 2003-123982, Japanese Unexamined Patent Publication No. 2002-170684, EP 1211257, Japanese Unexamined Patent Publication No. 2002-226495, Japan Japanese Unexamined Patent Publication No. 2002-234894, Japanese Unexamined Patent Publication No. 2001-247859, Japanese Unexamined Patent Publication No. 2001-298470, Japanese Unexamined Patent Publication 2002-173674, Japanese Unexamined Patent Publication 2002-203678, Japanese Unexamined Patent Publication 2002- 203679, JP 2004-357791, JP 2006-256999, JP 2007-19462, JP 2007-8463 The phosphorescent compound described in the patent document of Unexamined-Japanese-Patent No. 2007-96259, etc. are mentioned, Especially, as a more preferable luminescent material, Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex And phosphorescent metal complex compounds such as Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd complex, Dy complex, and Ce complex. Particularly preferred are Ir complexes, Pt complexes, or Re complexes, among which Ir complexes, Pt complexes comprising at least one coordination mode of metal-carbon bonds, metal-nitrogen bonds, metal-oxygen bonds, metal-sulfur bonds Or a Re complex is preferred. Moreover, Ir complex and Pt complex are especially preferable from a viewpoint of luminous efficiency, drive durability, chromaticity, etc., and Ir complex is the most preferable.

It is preferable to use the iridium complex represented by general formula (E-1) shown below, or the platinum complex represented by the following general formula (C-1) as a phosphorescence emitting material contained in the light emitting layer in this invention. .

General formula (E-1) is demonstrated.

[Chemical Formula 18]

In General Formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.

A ₁ represents a group of atoms which together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms.

B ₁ represents an atomic group which forms a 5 or 6 membered ring together with Z ² and a carbon atom.

(X-Y) represents a monoanionic bidentate ligand.

_nE1 represents the integer of 1-3.

_nE1 represents the integer of 1-3, Preferably it is 2 or 3.

Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom. Z ¹ and Z ² are preferably carbon atoms.

A ₁ represents a group of atoms which together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms. Examples of the 5 or 6 membered hetero ring containing A ₁ , Z ¹ and a nitrogen atom include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring and thiazole ring , Triazole ring, oxadiazole ring, thiadiazole ring and the like.

In view of stability of the complex, emission wavelength control and emission quantum yield, a 5 or 6 membered hetero ring formed of A ₁ , Z ¹ and nitrogen atoms, preferably a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring More preferably a pyridine ring, an imidazole ring, a pyrazine ring, still more preferably a pyridine ring, an imidazole ring, and most preferably a pyridine ring.

The 5 or 6 membered hetero ring formed of A ₁ , Z ¹ and a nitrogen atom may have a substituent, and as the substituent on the carbon atom, the substituent group A is applicable to the substituent group B as the substituent on the nitrogen atom. Can be. As a substituent on carbon, Preferably, they are an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, and a fluorine atom.

Substituents are appropriately selected for emission wavelength or potential control, but in the case of shortening, an electron donating group, a fluorine atom, an aromatic ring group is preferable, and for example, an alkyl group, a dialkylamino group, an alkoxy group, a fluorine atom, an aryl group, and an aromatic group Hetero ring groups and the like are selected. Moreover, when making it long-wavelength, an electron withdrawing group is preferable, for example, a cyano group, a perfluoroalkyl group, etc. are selected.

As a substituent on nitrogen, Preferably it is an alkyl group, an aryl group, an aromatic heterocyclic group, and an alkyl group and an aryl group are preferable from a viewpoint of stability of a complex.

The substituents may be linked to each other to form a condensed ring. Examples of the ring formed include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring and a pyrazole. A ring, a thiophene ring, a furan ring, etc. are mentioned. The ring formed may have a substituent and the substituent on the carbon atom mentioned above and the substituent on a nitrogen atom are mentioned as a substituent.

B ₁ represents a 5 or 6 membered ring containing Z ² and a carbon atom. Examples of the 5 or 6 membered ring formed of B ₁ , Z ² and carbon atoms include benzene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring and oxazole ring , Thiazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiophene ring, furan ring and the like.

As a 5 or 6 membered ring formed from B ₁ , Z ² and carbon atoms in terms of stability of the complex, emission wavelength control and emission quantum yield, preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring , Thiophene ring, More preferably, they are a benzene ring, a pyridine ring, a pyrazole ring, More preferably, they are a benzene ring and a pyridine ring.

The 5 or 6 membered ring formed of said B <_1> , Z <^2> and a carbon atom may have a substituent, The said substituent group B is applicable as a substituent on a carbon atom, and the said substituent group B is applicable as a substituent on a nitrogen atom. . As a substituent on carbon, Preferably, they are an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, and a fluorine atom.

The substituent is appropriately selected for the control of the emission wavelength or potential, but in the case of making the wavelength longer, an electron donating group and an aromatic ring group are preferable, and an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, an aromatic heterocyclic group, etc. are selected. do. Moreover, when shortening, an electron withdrawing group is preferable, for example, a fluorine atom, a cyano group, a perfluoroalkyl group, etc. are selected.

As a substituent on nitrogen, Preferably it is an alkyl group, an aryl group, an aromatic heterocyclic group, and an alkyl group and an aryl group are preferable from a viewpoint of stability of a complex. The substituents may be linked to each other to form a condensed ring. Examples of the ring formed include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring and a pyrazole. A ring, a thiophene ring, a furan ring, etc. are mentioned. The ring formed may have a substituent and the substituent on the carbon atom mentioned above and the substituent on a nitrogen atom are mentioned as a substituent.

Moreover, the substituent of the 5 or 6-membered heterocyclic ring formed with said A <_1> , Z <^1> and a nitrogen atom, and the substituent of the 5 or 6-membered ring formed with said B <_1> , Z <^2> and a carbon atom are connected, and are the same condensed ring as mentioned above May be formed.

As the ligand represented by (XY), there are various known ligands used in conventionally known metal complexes. For example, `` Photochemistry and Photophysics of Coordination Compounds '' by Springer-Verlag, H. Yersin, published in 1987, "Organic Metal Chemistry-Foundations and Applications-Shokabo Publishing Co., Ltd. Yamamoto Akio Published in 1982, etc. Ligands (eg halogen ligands (preferably chlorine ligands), nitrogen-containing heteroaryl ligands (eg bipyridyl, phenan) A diketone ligand (for example, acetylacetone, etc.) As a ligand represented by (XY), Preferably it is a diketone or a picolinic acid derivative, and the stability of a complex and high luminous efficiency are acquired. Most preferable is acetylacetonate (acac) shown below from a viewpoint.

[Chemical Formula 19]

* Indicates a coordination position relative to iridium.

 As the ligand represented by (X-Y), the following general formulas (l-1) to (l-14) are preferable, but the present invention is not limited to these.

[Chemical Formula 20]

* Represents a coordination position with respect to iridium in general formula (E-1). Rx, Ry and Rz each independently represent a hydrogen atom or a substituent.

When Rx, Ry, and Rz represent a substituent, the substituent selected from the said substituent group A is mentioned. Preferably, Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, a fluorine atom, It is a phenyl group which may be substituted, Most preferably, they are a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom, and a phenyl group. Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom, or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may be substituted, and most preferably hydrogen It is either an atom or a methyl group. Since these ligands are not considered to be sites where electrons are concentrated by the charge transport or excitation in the device, Rx, Ry, and Rz may be chemically stable substituents, and do not affect the effect of the present invention.

Moreover, it is also preferable to use the monoanionic ligand shown by general formula (I-15) as an auxiliary ligand.

[Chemical Formula 21]

R ^I1 to R ^I4 in General Formula (I-15) represent a substituent selected from a hydrogen atom or a substituent group A, and B represents a CR or a nitrogen atom. R represents a substituent selected from substituent group A. R ^I5 to R ^I7 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O) R,- NR _2, -NO _2, -OR, halogen atom, an aryl group or a heteroaryl group, a may have a substituent further. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group. * Represents a coordination position with respect to iridium in general formula (E-1).

Any two of R ^I1 , R ^I5 , R ^I6 and R ^I7 may be bonded to each other to form a condensed 4 to 7 membered ring, and the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 The 7-membered ring may further have a substituent Z.

Z is independently a halogen atom, -R '', -OR '', -N (R '') ₂ , -SR '', -C (O) R '', -C (O) OR '', -C (O) N (R '') ₂ , -CN, -NO ₂ , -SO ₂ , -SOR '', -SO ₂ R '', or -SO ₃ R '', and R '' is Each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

The preferable ranges of R ^I1 to R ^I7 are the same as the preferable ranges of R ^T1 to R ^T7 in General Formula (E-3) described later. As B, Preferably it is CR, As R, Preferably it is an aryl group, More preferably, it is a C6-C30 substituted or unsubstituted aryl group (for example, a phenyl group, a tolyl group, a naphthyl group, etc.), Especially Preferably it is a phenyl group.

As (X-Y), More preferably, they are (I-1), (I-4), (I-15), Especially preferably, they are (I-1) and (I-15). Complexes having these ligands can be synthesized in the same manner as known synthesis examples by using the corresponding ligand precursor. For example, it can synthesize | combine by the method shown below using the commercially available difluoroacetylacetone similarly to the method of international publication 2009-073245.

The preferable aspect of Ir complex represented by general formula (E-1) is Ir complex represented by general formula (E-2).

[Chemical Formula 22]

In General Formula (E-2), A ^E1 to A ^E8 each independently represent a nitrogen atom or CR ^E.

R ^E represents a hydrogen atom or a substituent.

(X-Y) represents a monoanionic bidentate ligand.

_nE2 represents the integer of 1-3.

A ^E1 to A ^E8 each independently represent a nitrogen atom or CR ^E. R ^E represents a hydrogen atom or a substituent, and R ^E may be connected to each other to form a ring. As a ring formed, the thing similar to the condensed ring mentioned in general formula (E-1) mentioned above is mentioned. As a substituent represented by R <^E> , what was illustrated as said substituent group A is applicable.

A ^E1 to A ^E4 are preferably CR ^E , and when A ^E1 to A ^E4 are CR ^E , R ^E of A ^E3 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, or an aryl jade. It is a time period, a fluorine atom, or a cyano group, More preferably, it is a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, Especially preferably, it is a hydrogen atom or a fluorine atom, A ^E1 , A ^E2 and A R ^E of ^E4 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, and more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group Or a fluorine atom, particularly preferably a hydrogen atom.

A ^A5 to A ^E8 is preferably CR ^E , and when A ^E5 to A ^E8 is CR ^E , as R ^E , preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, It is a dialkylamino group, a diarylamino group, an alkyloxy group, a cyano group, or a fluorine atom, More preferably, it is a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, or a fluorine atom, Preferably, they are a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. If possible, substituents may be linked to each other to form a condensed structure. When shifting the emission wavelength toward the short wavelength side, it is preferable that A ^E6 is a nitrogen atom.

(XY) and n _E2 are synonymous with (XY) and n _E1 in general formula (E-1), and its preferable range is also the same.

The more preferable aspect of the compound represented by said general formula (E-2) is a compound represented with the following general formula (E-3).

(23)

In General Formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, A perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O) R, -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, and further a substituent Z You may have it. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

A represents CR 'or a nitrogen atom, and R' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O ), R, -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, and may further have a substituent Z. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

R ^T1 -R ^T7 And R ' Arbitrary two may bond with each other to form a condensed 4 to 7 membered ring, the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 membered ring further has a substituent Z You may be. Of these, the case in which the R chukhwan ^T1 and ^T7 R or R and R ^{T5 T6} form a benzene ring are preferred, and it is particularly preferred if the chukhwan as R and R ^{T5 T6} form a benzene ring.

Substituents Z are each independently a halogen atom, -R '', -OR '', -N (R '') ₂ , -SR '', -C (O) R '', -C (O) OR '' , -C (O) N (R '') ₂ , -CN, -NO ₂ , -SO ₂ , -SOR '', -SO ₂ R '', or -SO ₃ R '', and R '' Each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

(XY) represents a monoanionic ligand. _nE3 represents the integer of 1-3.

As the alkyl group, the substituent Z described above may be mentioned as a group which may have a substituent, may be saturated or unsaturated, and may substitute. R ^T1 -R ^T7 And R ' As an alkyl group represented by these, Preferably it is an alkyl group of 1-8 carbon atoms, More preferably, it is an alkyl group of 1-6 carbon atoms, For example, a methyl group, an ethyl group, i-propyl group, a cyclohexyl group, t-butyl group etc. are mentioned, A methyl group is especially preferable.

The cycloalkyl group may have a substituent, may be saturated or unsaturated, or the substituent Z described above may be mentioned as the group which may be substituted. R ^T1 -R ^T7 And R ' As a cycloalkyl group shown by these, Preferably it is a cycloalkyl group of 4-7 ring atoms, More preferably, it is a cycloalkyl group of 5-6 carbon atoms, For example, a cyclopentyl group, a cyclohexyl group, etc. are mentioned. have.

R ^T1 -R ^T7 And R ' As an alkenyl group represented by these, Preferably it is C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, vinyl, allyl, 1-propenyl, 1-isopro Phenyl, 1-butenyl, 2-butenyl, 3-pentenyl, and the like.

R ^T1 to R ^T7 and R ' As an alkynyl group represented by these, Preferably it is C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, ethynyl, Propargyl, 1-propynyl, 3 -Pentynyl, etc. are mentioned.

R ^T1 -R ^T7 And R ' Examples of the perfluoroalkyl group include those in which all hydrogen atoms of the alkyl group described above are substituted with fluorine atoms.

R ^T1 -R ^T7 And R ' As an aryl group represented by these, Preferably a C6-C30 substituted or unsubstituted aryl group, for example, a phenyl group, a tolyl group, a naphthyl group, etc. are mentioned, A phenyl group is especially preferable.

R ^T1 to R ^T7 and R ' As a heteroaryl group represented by these, Preferably it is a C5-8 heteroaryl group, More preferably, it is a 5 or 6-membered substituted or unsubstituted heteroaryl group, For example, a pyridyl group, a pyrazinyl group, Pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, furyl, benzofu Aryl group, thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group , Benzisothiazolyl group, thiadiazolyl group, isoxoxazolyl group, benzisooxazolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolidinyl group, thiazolinyl group, sulfonyl group , Carbazolyl group, dibenzofuryl group, dibenzothienyl group, 7 Pyrido indolyl group etc. are mentioned. Preferable examples are pyridyl group, pyrimidinyl group, imidazolyl group and thienyl group, and more preferably pyridyl group and pyrimidinyl group.

R ^T1 -R ^T7 And R ' Preferably, it is a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group, heteroaryl group, More preferably, a hydrogen atom, an alkyl group, and a cyano group , A trifluoromethyl group, a fluoro group and an aryl group, more preferably a hydrogen atom, an alkyl group and an aryl group. As the substituent Z, an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom is more preferable.

R ^T1 -R ^T7 And R ' Arbitrary two may combine with each other to form a condensed 4 to 7 membered ring, the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 membered ring further has a substituent Z You may have it. Definitions and preferred ranges of cycloalkyl, aryl, heteroaryl to be formed are R ^T1 to R ^T7 And a cycloalkyl group, an aryl group, a heteroaryl group defined by R '.

In addition, while A represents CR ', R ^T1 to R ^T7 It is especially preferable that 0-2 are alkyl groups or a phenyl group, and all remainders are hydrogen atoms in R ', and R <^T1> -R <^T7>. And R ' Wherein from 0 to two are each the group, and the remainder is a particularly preferred all a hydrogen atom, R R ~ ^{T1 T7} And R ' Among them, most preferably 0 to 2 are methyl groups, and the rest are all hydrogen atoms.

It is preferable that n _E3 is 2 or 3. It is preferable that the kind of ligand in a complex is comprised from 1-2 types, More preferably, it is one type. When introducing a reactive group into a complex molecule, it is also preferable that a ligand consists of two types from a viewpoint of the ease of synthesis.

 (X-Y) is synonymous with (X-Y) in General formula (E-1), and its preferable range is also the same.

One of the preferable forms of the compound represented by said general formula (E-3) is a compound represented with the following general formula (E-4).

&Lt; EMI ID =

R ^T1 to R ^T4 , A, (XY) and n _E4 in General Formula (E-4) are R ^T1 to R ^T4 , A, (XY) and n _{E3 in} General Formula (E-3). It is synonymous with and a preferable range is also the same. R ₁ 'to R ₅ ' are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O) R , -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, may further have a substituent Z. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

Any two of R ₁ ′ to R ₅ ′ may be bonded to each other to form a condensed 4 to 7 membered ring, and the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 membered ring May further have a substituent Z.

Z is independently a halogen atom, -R '', -OR '', -N (R '') ₂ , -SR '', -C (O) R '', -C (O) OR '', -C (O) N (R '') ₂ , -CN, -NO ₂ , -SO ₂ , -SOR '', -SO ₂ R '', or -SO ₃ R '', and R '' is Each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

Moreover, the preferable range in R <_1> -R <_5>'is the same as that of R <^T1> -R <^T7> , R' in general formula (E-3). In A a "with a represents a, R ^T1 ~ R ^T4, R 'CR and R _1' ~ R ₅ 'of, from 0 to two are each an alkyl group or a phenyl group, and the other is a particularly preferred if all of the hydrogen atoms, R More preferably, 0 to 2 are alkyl groups in ^T1 to R ^T4 , R 'and R ₁ ' to R ₅ ', and the rest are all hydrogen atoms.

Another preferable form of the compound represented by said general formula (E-3) is a compound represented with the following general formula (E-5).

(25)

In the formula ^{(E5) R T2 ~ R T6} , A, (XY) n and _E5 is R ~ R ^{T2 T6,} A in the formula (E3), (XY) n and _E3 and It is synonymous and a preferable range is also the same. R ₆ 'to R ₈ ' are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O) R , -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, may further have a substituent Z. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

Any two of R ^T5 , R ^T6 and R ₆ 'to R ₈ ' may combine with each other to form a condensed 4 to 7 membered ring, and the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and The condensed 4 to 7 membered ring may further have a substituent Z.

Z is independently a halogen atom, -R '', -OR '', -N (R '') ₂ , -SR '', -C (O) R '', -C (O) OR '', -C (O) N (R '') ₂ , -CN, -NO ₂ , -SO ₂ , -SOR '', -SO ₂ R '', or -SO ₃ R '', and R '' is Each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

Moreover, the preferable range in R <_6>'-R<_8>' is the same as that of R <^T1> -R <^T7> , R 'in general formula (E-3). In A a "with a represents a, R ^T2 ~ R ^T6, R, CR, and R ₆ '~ R _8, wherein from 0 to two are each an alkyl group or a phenyl group, are particularly preferred if the rest is all hydrogen atoms, and R More preferably, 0 to 2 are alkyl groups in ^T2 to R ^T6 , R 'and R ₆ ' to R ₈ ', and the rest are all hydrogen atoms.

When using the phosphorescent light emitting material represented by General Formula (E-4) or (E-5), the compound represented by General Formula (1) is preferably contained in the light emitting layer or the hole block layer, and more preferably contained in the light emitting layer. desirable.

Another preferable form of a compound represented by general formula (E-1) is a case represented by the following general formula (E-6).

(26)

In General Formula (E-6), R _1a to R _1k are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, and -CO ₂ R , -C (O) R, -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, and may further have a substituent Z. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

Any two of R _1a to R _1k may be bonded to each other to form a condensed 4 to 7 membered ring, the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 membered ring is further added. May have a substituent Z.

Z is independently a halogen atom, -R '', -OR '', -N (R '') ₂ , -SR '', -C (O) R '', -C (O) OR '', -C (O) N (R '') ₂ , -CN, -NO ₂ , -SO ₂ , -SOR '', -SO ₂ R '', or -SO ₃ R '', and R '' is Each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

(X-Y) represents a monoanionic bidentate ligand.

_nE6 represents the integer of 1-3.

In general formula (E-6), the preferable range of R <_1a> -R <_1k> is the same as that of R <^T1> -R <^T7> , R 'in general formula (E-3). Moreover, the case where 0-2 is an alkyl group or a phenyl group among R <_1a> -R <_1k> is especially preferable that all remainders are hydrogen atoms, and when R <_2a> -R <_1k> is 0-2 pieces are alkyl groups and all remainders are all hydrogen atoms, More preferred.

It is especially preferable when _R1j and _R1k are connected to form a single bond.

Preferable ranges of (XY) and n _E6 are the same as (XY) and n _{E3 in} General formula (E-3).

The more preferable aspect of a compound represented by general formula (E-6) is a case represented by the following general formula (E-7).

(27)

In General Formula (E-7), R _1a to R _1i are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, and -CO ₂ R , -C (O) R, -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, and may further have a substituent Z. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

Any two of R _1a to R _1k may be bonded to each other to form a condensed 4 to 7 membered ring, and the condensed 4 to 7 membered ring is a cycloalkyl group, an aryl group or a heteroaryl group, and the condensed 4 to 7 membered ring May further have a substituent Z.

Z is independently a halogen atom, -R '', -OR '', -N (R '') ₂ , -SR '', -C (O) R '', -C (O) OR '', -C (O) N (R '') ₂ , -CN, -NO ₂ , -SO ₂ , -SOR '', -SO ₂ R '', or -SO ₃ R '', and R '' is Each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

(X-Y) represents a monoanionic bidentate ligand.

_nE7 represents the integer of 1-3.

In the general formula (E-7), defined and preferred ranges of R _1a ~ R _1i is the same as R _1a ~ R _1i in the formula (E-6). Moreover, the case where 0-2 is an alkyl group or an aryl group among R <_1a> -R <_1i> , and the remainder are all hydrogen atoms is especially preferable. The definition and the preferred range of (XY) and n _E7 are the same as those of (XY) and n _E3 in General Formula (E-3).

When using the phosphorescence emitting material represented by general formula (E-6) or (E-7), it is preferable that the compound represented by general formula (1) is contained in a light emitting layer or a hole block layer.

Although the preferable specific example of a compound represented by general formula (E-1) is listed below, it is not limited to the following.

(28)

[Formula 29]

(30)

The compound illustrated as a compound represented by said general formula (E-1) can be synthesize | combined by the method of Unexamined-Japanese-Patent No. 2009-99783, and the various methods of US Pat. After synthesis, purification by column chromatography, recrystallization or the like is preferably followed by purification by sublimation purification. By sublimation purification, not only organic impurities can be separated but also inorganic salts, residual solvents, and the like can be effectively removed.

Although it is preferable that the compound represented by general formula (E-1) is contained in a light emitting layer, the use is not limited and may be further contained in any layer in an organic layer.

Although the compound represented by general formula (E-1) in a light emitting layer is contained 0.1 mass%-50 mass% with respect to the mass of all the compounds which form a light emitting layer generally in a light emitting layer, 1 mass%-50 from a viewpoint of durability and an external quantum efficiency. It is preferable to contain mass%, and it is more preferable to contain 2 mass%-40 mass%.

As a platinum complex which can be used as a phosphorescence emitting material, Preferably it is a platinum complex represented by following General formula (C-1).

(31)

(Wherein, Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand that coordinates to Pt. L ¹ , L ² and L ³ each independently represent a single bond or a divalent linking group.)

General formula (C-1) is demonstrated. Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand that coordinates to Pt. At this time, any one of Q ¹ , Q ² , Q ³ and Q ⁴ and Pt may be a covalent bond, an ionic bond, a coordination bond, or the like. Q ^1, Q ^2, atom bonded to the Q ³ and Q ⁴ Pt in is the carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom is preferred and, Q ^1, Q ^2, Q ³ and Q ⁴ Pt of It is preferable that at least 1 is a carbon atom, it is more preferable that 2 is a carbon atom among the couple | bonding atoms, It is especially preferable that 2 is a carbon atom and 2 is a nitrogen atom.

Q ¹ , Q ² , Q ^3, and Q ⁴ bonded to the carbon atom Pt may be an anionic ligand or a neutral ligand, and an anionic ligand may be a vinyl ligand or an aromatic hydrocarbon ring ligand (for example, a benzene ligand, a naphthalene ligand). , Anthracene ligand, phenanthrene ligand, etc., heterocyclic ligand (e.g. furan ligand, thiophene ligand, pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, Pyrrole ligands, imidazole ligands, pyrazole ligands, triazole ligands and condensates containing them (for example, quinoline ligands, benzothiazole ligands, etc.). Neutral ligands include carbene ligands.

The group represented by Q <^1> , Q <^2> , Q <^3> and Q <^4> may have a substituent, and what was illustrated as said substituent group A as a substituent is applicable suitably. Moreover, substituents may be connected (when Q <^3> and Q <^4> are connected, it will become a Pt complex of a cyclic 4 left ligand).

As the group represented by Q ¹ , Q ² , Q ³ and Q ⁴ , preferably, an aromatic hydrocarbon ring ligand bonded to Pt by a carbon atom, an aromatic heterocyclic ligand bonded to Pt by a carbon atom, and a nitrogen-containing aromatic bond to Pt by a nitrogen atom Heterocyclic ligand, acyloxy ligand, alkyloxy ligand, aryloxy ligand, heteroaryloxy ligand, silyloxy ligand, more preferably an aromatic hydrocarbon ring ligand bonded to Pt by a carbon atom, an aromatic hetero ring bonded to Pt by a carbon atom Ligands, nitrogen-containing aromatic heterocyclic ligands bound to Pt with nitrogen atoms, acyloxy ligands, aryloxy ligands, more preferably aromatic hydrocarbon ring ligands bound to Pt with carbon atoms, aromatic heterocyclic ligands bound to Pt with carbon atoms, Nitrogen-containing aromatics bound to Pt with a nitrogen atom Interrogating ring ligand, an acyloxy ligand.

L ¹ , L ² and L ³ represent a single bond or a divalent linking group. Examples of the divalent linking groups represented by L ¹ , L ^2, and L ³ include an alkylene group (methylene, ethylene, propylene, and the like), an arylene group (phenylene, naphthalenediyl), a heteroarylene group (pyridindiyl, thiophendiyl, and the like), Imino group (-NR-) (phenylimino group, etc.), oxy group (-O-), thio group (-S-), phosphinidene group (-PR-) (phenylphosphinidene group, etc.), silylene group (- SiRR'-) (dimethylsilylene group, diphenylsilylene group, etc.), or what combined these is mentioned. Here, as R and R ', an alkyl group, an aryl group, etc. are respectively independently mentioned. These linking groups may further have a substituent.

In view of the stability of the complex and the luminescence quantum yield, L ¹ , L ² and L ³ are preferably a single bond, an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group, a silylene group, More preferably, they are a single bond, an alkylene group, an arylene group, and an imino group, More preferably, they are a single bond, an alkylene group, an arylene group, More preferably, they are a single bond, a methylene group, a phenylene group, More preferably, It is a bond and a di-substituted methylene group, More preferably, it is a single bond, a dimethyl methylene group, a diethyl methylene group, a diisobutyl methylene group, a dibenzyl methylene group, an ethyl methylene methylene group, a methylpropyl methylene group, isobutyl methylene methylene Group, diphenylmethylene group, methylphenylmethylene group, cyclohexanediyl group, cyclopentanediyl group, fluorenediyl group, and fluoromethylmethylene group.

L ¹ is particularly preferably a dimethylmethylene group, a diphenylmethylene group or a cyclohexanediyl group, and most preferably a dimethylmethylene group.

Most preferably, it is a single bond as L <^2> and L <^3> .

Among the platinum complexes represented by General Formula (C-1), more preferably, they are platinum complexes represented by the following General Formula (C-2).

(32)

In the formula, L ²¹ represents a single bond or a divalent linking group. A ²¹ and A ²² each independently represent a carbon atom or a nitrogen atom. Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic hetero ring. Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic hetero ring.)

General formula (C-2) is demonstrated. L <^21> is synonymous with L <^1> in the said general formula (C-1), and its preferable range is also the same.

A ²¹ and A ²² each independently represent a carbon atom or a nitrogen atom. At least one of A ²¹ and A ²² is preferably a carbon atom, and A ²¹ and A ²² are preferably both carbon atoms from the viewpoint of the stability of the complex and the light emitting quantum yield of the complex.

Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic hetero ring. Examples of the nitrogen-containing aromatic hetero rings represented by Z ²¹ and Z ²² include pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring and oxa A diazole ring, a thiadiazole ring, and the like. From the viewpoint of stability of the complex, emission wavelength control and emission quantum yield, the ring represented by Z ²¹ , Z ²² is preferably a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, more preferably a pyridine ring, It is an imidazole ring and a pyrazole ring, More preferably, it is a pyridine ring and a pyrazole ring, Especially preferably, it is a pyridine ring.

Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic hetero ring. Examples of the nitrogen-containing aromatic hetero rings represented by Z ²³ and Z ²⁴ include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring and tria A sol ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, a furan ring, etc. are mentioned. As a ring represented by Z ²³ , Z ²⁴ from the viewpoint of stability of the complex, emission wavelength control, and emission quantum yield, a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, a thiophene ring, and Preferably they are a benzene ring, a pyridine ring, a pyrazole ring, More preferably, they are a benzene ring and a pyridine ring.

Among the platinum complexes represented by General Formula (C-2), one of more preferred embodiments is a platinum complex represented by the following General Formula (C-4).

(33)

(In General Formula (C-4), A ⁴⁰¹ to A ⁴¹⁴ each independently represent CR or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁴¹ represents a single bond or a divalent linking group.)

General formula (C-4) is demonstrated.

A ⁴⁰¹ to A ⁴¹⁴ each independently represent CR or a nitrogen atom. R represents a hydrogen atom or a substituent.

As a substituent represented by R, the thing illustrated as said substituent group A is applicable.

It is preferably CR as A ⁴⁰¹ to A ⁴⁰⁶ , and R may be connected to each other to form a ring. When A ⁴⁰¹ to A ⁴⁰⁶ are CR, each of R ⁴⁰² and A ⁴⁰⁵ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, and more preferably. Is a hydrogen atom, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, Especially preferably, they are a hydrogen atom and a fluorine atom. R of A ⁴⁰¹ , A ⁴⁰³ , A ⁴⁰⁴ , A ⁴⁰⁶ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, and more preferably a hydrogen atom or an amino group , An alkoxy group, an aryloxy group and a fluorine atom, particularly preferably a hydrogen atom.

L ⁴¹ has the same meaning as L ¹ in General Formula (C-1), and the preferred range thereof is also the same.

As A ⁴⁰⁷ -A ⁴¹⁴ , in each of A ⁴⁰⁷ -A ⁴¹⁰ and A ⁴¹¹ -A ⁴¹⁴ , the number of N (nitrogen atoms) is preferably 0 to 2, and more preferably 0 to 1. In the case where the emission wavelength is shifted to the shorter wavelength side, either A ⁴⁰⁸ or A ⁴¹² is preferably a nitrogen atom, and more preferably A ⁴⁰⁸ and A ⁴¹² are a nitrogen atom together.

Among the platinum complexes represented by General Formula (C-2), one of more preferred embodiments is a platinum complex represented by the following General Formula (C-5).

[Formula 34]

(In General Formula (C-5), A ⁵⁰¹ to A ⁵¹² each independently represent CR or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁵¹ represents a single bond or a divalent linking group.)

General formula (C-5) is demonstrated. A ⁵⁰¹ to A ⁵⁰⁶ and L ⁵¹ have the same meanings as A ⁴⁰¹ to A ⁴⁰⁶ and L ^{41 in} the general formula (C-4), and the preferred range thereof is also the same.

A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² each independently represent a CR or nitrogen atom. R represents a hydrogen atom or a substituent. As a substituent represented by R, the thing illustrated as said substituent group A is applicable.

Among the platinum complexes represented by General Formula (C-1), another more preferred embodiment is a platinum complex represented by the following General Formula (C-6).

(35)

In the formula, L ⁶¹ represents a single bond or a divalent linking group. A ⁶¹ each independently represents a carbon atom or a nitrogen atom. Z ⁶¹ and Z ⁶² each independently represent a nitrogen-containing aromatic hetero ring. Z ⁶³ represents Each independently represents a benzene ring or an aromatic hetero ring, wherein Y is an anionic, acyclic ligand that binds to Pt.)

General formula (C-6) is demonstrated. L ⁶¹ has the same meaning as L ¹ in General Formula (C-1), and the preferred range thereof is also the same.

A ⁶¹ represents a carbon atom or a nitrogen atom. It is preferable that A ⁶¹ is a carbon atom from a viewpoint of the stability of a complex, and the light emission quantum yield of a complex.

Z ⁶¹ and Z ⁶² have the same meanings as Z ²¹ and Z ^{22 in} General Formula (C-2), and the preferred ranges are also the same. Z ⁶³ has the same meaning as Z ²³ in General Formula (C-2), and the preferred range thereof is also the same.

Y is an anionic acyclic ligand that binds to Pt. Acyclic ligands are those in which atoms bonded to Pt do not form a ring in the ligand state. As an atom couple | bonded with Pt in Y, a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom are preferable, a nitrogen atom and an oxygen atom are more preferable, and an oxygen atom is the most preferable.

Examples of Y bonded to Pt as a carbon atom include vinyl ligands. Examples of Y bonded to Pt by a nitrogen atom include amino ligands and imino ligands. Examples of Y bonded to Pt by an oxygen atom include alkoxy ligands, aryloxy ligands, heteroaryloxy ligands, acyloxy ligands, silyloxy ligands, carboxyl ligands, phosphoric acid ligands, sulfonic acid ligands and the like. Examples of Y bonded to Pt with a sulfur atom include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, and thiocarboxylic acid ligands.

The ligand represented by Y may have a substituent and the thing illustrated as said substituent group A can be suitably applied as a substituent. Moreover, substituents may be connected.

As a ligand represented by Y, Preferably it is a ligand couple | bonded with Pt by an oxygen atom, More preferably, it is an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand, a silyloxy ligand, More preferably, it is an acyloxy I'm a traitor.

Among the platinum complexes represented by General Formula (C-6), one of more preferred embodiments is a platinum complex represented by the following General Formula (C-7).

(36)

(Wherein, A ⁷⁰¹ to A ⁷¹⁰ each independently represent CR or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁷¹ represents a single bond or a divalent linking group. Y represents an anionic bond to Pt. Acyclic ligand.)

General formula (C-7) is demonstrated. L ⁷¹ has the same meaning as L ⁶¹ in General Formula (C-6), and the preferred range thereof is also the same. A ⁷⁰¹ to A ⁷¹⁰ have the same meanings as A ⁴⁰¹ to A ⁴¹⁰ in General Formula (C-4), and the preferred ranges are also the same. Y is synonymous with Y in General formula (C-6), and its preferable range is also the same.

As a platinum complex represented by general formula (C-1), the compound as described in [0143]-[0152], [0157]-[0158], [0162]-[0168] of Unexamined-Japanese-Patent No. 2005-310733 specifically, , The compounds described in [0065] to [0083] of JP 2006-256999 A, the compounds described in [0065] to [0090] of JP 2006-93542 A, and the compounds of JP 2007-73891 A The compound described in [0071], The compound described in [0079] to [0083] of JP 2007-324309, The compound described in [0065] to [0090] of JP 2006-93542, JP The compound as described in [0055]-[0071] of 2007-96255, the compound as described in [0043]-[0046] of Unexamined-Japanese-Patent No. 2006-313796, and the platinum complex illustrated below are mentioned. .

[Formula 37]

(38)

[Chemical Formula 39]

The platinum complex compound represented by General Formula (C-1) is described, for example, on page 789 of the Journal of Organic Chemistry 53, 786, (1988), GR Newkome et al. 2752 of the method described, page 790, left column 18-38, the method described on page 790, right column 19-30, and combinations thereof, Chemische Berichte 113, 2749 (1980), H. Lexy et al. It can synthesize | combine by various techniques, such as the method of page, line 26-35.

For example, the ligand, or the dissociation agent and the metal compound thereof may be a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, and a sulfone type). Solvents, sulfoxide solvents, water, and the like, or in the absence of a solvent and in the presence of a base (inorganic and organic bases, for example, sodium methoxide and t-butoxy potassium) And triethylamine, potassium carbonate and the like), or in the absence of a base, can be obtained at room temperature or lower, or by heating (a method of heating by microwave in addition to normal heating is also effective).

It is preferable that content of the compound represented by general formula (C-1) in the light emitting layer of this invention is 1-30 mass% in a light emitting layer, It is more preferable that it is 3-25 mass%, It is 5-20 mass% More preferred.

Although the kind of the said fluorescent light emitting material is not specifically limited, For example, benzoxazole, benzoimidazole, benzothiazole, styrylbenzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin , Pyran, perinone, oxadiazole, aldazine, pyralidine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolepyridine, cyclopentadiene, styrylamine, condensed polycyclic Aromatic compounds (such as anthracene, phenanthroline, pyrene, perylene, rubrene or pentacene), metal complexes of 8-quinolinol, various metal complexes represented by pyrimethene complexes or rare earth complexes, polythiophenes, polyphenyls Polymer compounds such as ylene and polyphenylenevinylene, organic silanes, and derivatives thereof.

Although the specific example of a fluorescent light emitting material is shown below, this invention is not limited to these.

[Formula 40]

(41)

(42)

(43)

(44)

[Chemical Formula 45]

(46)

It is preferable that content of the fluorescent luminescent material in the light emitting layer of this invention is 1-30 mass% in a light emitting layer, It is more preferable that it is 1-20 mass%, It is further more preferable that it is 1-10 mass%.

In this invention, it is preferable that the maximum light emission wavelength of a luminescent material is 400-700 nm, It is more preferable that it is 500-700 nm from the point of quenching with the compound represented by General formula (1), 520-650 It is more preferable that it is nm, and it is most preferable that it is 520-550 nm.

The maximum light emission wavelength of the phosphorescent light emitting material represented by General Formula (E-3) includes a plurality of R ^T1 to R ^T7. And R ' In the case of not forming a ring together with each other, the maximum emission wavelength of the phosphorescent light emitting material represented by the general formula (E-4) or (E-5) is in the range of about 550 to 650 nm.

Although the thickness of a light emitting layer is not specifically limited, Usually, it is preferable that it is 2 nm-500 nm, Especially, it is more preferable that it is 5 nm-200 nm from a viewpoint of external quantum efficiency, It is more preferable that it is 10 nm-100 nm. desirable.

The light emitting layer in the element of this invention may be comprised only by the light emitting material, and may be the structure made into the mixed layer of a host material and a light emitting material. The kind of light emitting material may be 1 type, or 2 or more types may be sufficient as it. The host material is preferably a charge transporting material. The host material may be one type or two or more types, and the structure which mixed the electron-transport host material and the hole-transport host material is mentioned, for example. In addition, the light emitting layer may include a material having no charge transporting property and not emitting light.

The light emitting layer may be one layer or a multilayer of two or more layers, the same light emitting material and host material may be included in each layer, or different materials may be included for each layer. When there are a plurality of light-emitting layers, each light-emitting layer may emit light of a different color.

(Host material)

The host material is a compound mainly responsible for the injection and transport of electric charges in the light emitting layer, and is a compound that does not substantially emit light itself. The term "substantially does not emit light" herein means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less, and more preferably 1 It means that it is% or less.

As a host material, the compound represented by General formula (1) can be used.

As another host material which can be used for this invention, the following compounds are mentioned, for example.

Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran , Polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound , Porphyrin compounds, cyclic aromatic hydrocarbon compounds (fluorene, naphthalene, phenanthrene, triphenylene, etc.), polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, polythiophenes Conductive polymer oligomers, organic silanes, carbon films, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, etc. , Thiopyran dioxide, Heterocyclic tetracarboxylic anhydrides such as levodiimide, fluorenylidene methane, distyrylpyrazine, fluorine-substituted aromatic compounds, naphthaleneperylene, metal complexes of phthalocyanine, 8-quinolinol derivatives, metal phthalocyanine, benzoxazole and Various metal complexes and derivatives thereof (which may have a substituent or a condensation) etc. which are represented by the metal complex which makes benzothiazole a ligand are mentioned.

Among these, carbazole, dibenzothiophene, dibenzofuran, arylamine, a cyclic aromatic hydrocarbon compound and a metal complex are particularly preferable.

In the present invention, the host material that can be used in combination may be a hole transporting host material or an electron transporting host material.

In the light emitting layer, it is preferable that the triplet minimum excitation energy (T ₁ energy) in the film state of the host material is higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, luminous efficiency and driving durability. T ₁ of the host material is 0.1 eV or more greater than the T ₁ is preferably a phosphorescent light emitting material, and at least 0.2 eV and preferably greater than it, it is more preferably greater than 0.3 eV.

If T ₁ in the film state of the host material is smaller than the T ₁ of the phosphorescent light emitting material, the light emission due to discarding by quenching, the host material, the large T ₁ is required than the phosphorescent light-emitting material. In addition, even if the T ₁ of the host material is larger than the phosphorescent light-emitting material, in the case of both T ₁ difference it is small, because of rising energy transfer to the host material from a portion, the phosphorescent light emitting material, causing decreased efficiency degradation or durability. Accordingly, a host material having a sufficiently large T ₁ and high chemical stability and carrier injection and transportability is desired.

Moreover, although content of the host compound in this invention is not specifically limited, It is preferable that it is 15 mass% or more and 95 mass% or less with respect to the mass of all the compounds which form a light emitting layer from a light emitting efficiency and a driving voltage. In the case where the light emitting layer contains a plurality of types of host compounds containing the compound represented by the general formula (1), the compound represented by the general formula (1) is preferably 50 mass% or more and 99 mass% or less in all the host compounds.

It is preferable that the light emitting element of this invention contains an organic layer of at least 1 layer between a light emitting layer and a cathode, and it is the efficiency and drive of an element that at least 1 type of compound represented by following General formula (O-1) contains in this organic layer. It is preferable from a voltage point of view. General formula (O-1) is demonstrated below.

[Formula 47]

(In General Formula (O-1), R ^O1 represents an alkyl group, an aryl group, or a heteroaryl group. A ^O1 to A ^O4 each independently represent CR ^A or a nitrogen atom. R ^A represents a hydrogen atom, an alkyl group, or an aryl group. Or a heteroaryl group, a plurality of R ^As may be the same as or different from each other, L ^O1 represents a divalent to hexavalent linking group consisting of an aryl ring or a heteroaryl ring, n ^O1 represents an integer of 2 to 6;

R ^O1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms), and these are selected from the substituent group A described above You may have a substituent to become. R ⁰¹ is preferably an aryl group or a heteroaryl group, more preferably an aryl group. As a preferable substituent in the case where the aryl group of R <^O1> has a substituent, an alkyl group, an aryl group, or a cyano group is mentioned, An alkyl group or an aryl group is more preferable, An aryl group is still more preferable. When the aryl group of R ^O1 has plural substituents, the plural substituents may be bonded to each other to form a 5 or 6-membered ring. The aryl group of R ^O1 is preferably a phenyl group which may have a substituent selected from substituent group A, more preferably an alkyl group or a phenyl group which may be substituted by an aryl group, still more preferably an unsubstituted phenyl group or 2-phenyl It is a phenyl group.

A ^O1 to A ^O4 each independently represent CR ^A or a nitrogen atom. Of A ^O1 to A ^O4 , 0 to 2 are preferably nitrogen atoms, and 0 or 1 is more preferably a nitrogen atom. It is more preferable that all of A ^O1 to A ^O4 are CR ^A or A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are CR ^A , A ^O1 is a nitrogen atom, and A ^O2 to A ^O4 are CR ^A. It is more preferable that A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are CR ^A , and all of R ^A are hydrogen atoms.

R ^A represents a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms), and these groups of substituents described above You may have a substituent selected from A. Moreover, some R ^<A> may be same or different. R ^A is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.

L ^O1 represents a divalent to hexavalent linking group consisting of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms). L ^O1 is preferably an arylene group, a heteroarylene group, an aryltriyl group or a heteroaryltriyl group, more preferably a phenylene group, a biphenylene group or a benzenetriyl group, still more preferably a biphenylene group or a benzene tree It is a diary. L ^O1 may have a substituent selected from the substituent group A described above, and the substituent in the case of having a substituent is preferably an alkyl group, an aryl group or a cyano group. The following are mentioned as a specific example of L <^O1> .

(48)

^nO1 represents the integer of 2-6, Preferably it is an integer of 2-4, More preferably, it is 2 or 3. n ^O1 is most preferably 3 from the viewpoint of device efficiency, and most preferably 2 from the viewpoint of device durability.

The compound represented by general formula (O-1) is more preferably a compound represented by the following general formula (O-2).

(49)

(In General Formula (O-2), R ^O1 represents an alkyl group, an aryl group, or a heteroaryl group. R ^O2 to R ^O4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. A ^O1 to A ^O4 Each independently represents CR ^A or a nitrogen atom, R ^A represents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group, and a plurality of R ^A may be the same or different.)

R ^O1 and A ^O1 ~ ^O4 A is the same meaning as R A and ^{O1 O1} ~ ^O4 A in the formula (O1), yet it is the same from their preferred range.

R ⁰² to R ⁰⁴ each independently represent a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms) These may have a substituent selected from the substituent group A mentioned above. R ⁰² to R ⁰⁴ are preferably hydrogen atoms, alkyl groups or aryl groups, more preferably hydrogen atoms or aryl groups, and most preferably hydrogen atoms.

It is preferable that the glass transition temperature (Tg) is 100 degreeC-300 degreeC from the viewpoint which the compound represented by the said general formula (O-1) stably operates with respect to the stability at high temperature storage, the heat generation at the time of high temperature drive, and the drive. And it is more preferable that it is 120 degreeC-300 degreeC, It is still more preferable that it is 120 degreeC-300 degreeC, It is still more preferable that it is 140 degreeC-300 degreeC.

Although the specific example of a compound represented by general formula (O-1) is shown below, this invention is not limited to these.

(50)

(51)

The compound represented by the above general formula (O-1) can be synthesized by the method described in JP-A-2001-335776. After the synthesis, it is preferable to perform purification by column chromatography, recrystallization, reprecipitation or the like, and then purification by sublimation purification. Not only organic impurities can be separated by sublimation purification, but also inorganic salts, residual solvents, water and the like can be effectively removed.

In the light emitting device of the present invention, the compound represented by the general formula (O-1) is contained in the organic layer between the light emitting layer and the cathode, but is preferably contained in the layer on the cathode side adjacent to the light emitting layer.

 It is preferable that 70-100 mass% is contained with respect to the total mass of the organic layer to add, and, as for the compound represented by general formula (O-1), it is more preferable that 85-100 mass% is contained.

It is preferable that the light emitting element of this invention contains an organic layer of at least 1 layer between a light emitting layer and a cathode, and it is the efficiency and drive voltage of an element that the organic layer contains at least 1 sort (s) of compound represented by following General formula (P). It is preferable at the point of view. General formula (P) is demonstrated below.

(52)

(In general formula (P), ^RP represents an alkyl group (preferably C1-C8), an aryl group (preferably C6-C30), or heteroaryl group (preferably C4-C12), they may contain a substituent group selected from the aforementioned substituent group a. nP is the case of an integer of 1 ~ 10, R ^P is a plurality, they may be the same or different. R ^P at least one of the following general formula It is a substituent represented by (P-1)-(P-3).

(53)

(In General Formulas (P-1) to (P-3), R ^P1 to R ^P3 and R ' ^P1 to R' ^P3 each represent an alkyl group (preferably having 1 to 8 carbon atoms) and an aryl group (preferably having 6 carbon atoms). 30) or heteroaryl group (preferably C4-C12), These may have a substituent selected from the substituent group A mentioned above. N ^P1 and n ^P2 represent the integer of 0-4, R is If ^{P1 ~ R P3, R 'P1} ~ R' P3 is a plurality, they may be the same or different. L ^P1 ~ L ^P3 represents any of a divalent linking group consisting of a single bond, an aryl ring or heteroaryl ring * Indicates the position of attachment to the anthracene ring of formula (P).)

Preferable substituents other than the substituent represented by (P-1)-(P-3) as R <^P> are an aryl group, More preferably, they are any of a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, More preferably, a naphthyl group to be.

R ^P1 to R ^P3 and R ' ^P1 to R' ^P3 are preferably any one of an aryl group and a heteroaryl group, more preferably an aryl group, still more preferably a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group. It is either, Most preferably, it is a phenyl group.

L ^P1 to L ^P3 are preferably any of a divalent linking group consisting of a single bond and an aryl ring, more preferably any of a single bond, phenylene, biphenylene, terphenylene and naphthylene, and more preferably. Preferably a single bond, phenylene or naphthylene.

Although the specific example of a compound represented by general formula (P) is shown below, this invention is not limited to these.

[Formula 54]

(55)

The compound represented by the said general formula (P) can be synthesize | combined by the method as described in WO2003 / 060956, WO2004 / 080975, etc. After the synthesis, it is preferable to perform purification by column chromatography, recrystallization, reprecipitation or the like, and then purification by sublimation purification. Not only organic impurities can be separated by sublimation purification, but also inorganic salts, residual solvents, water and the like can be effectively removed.

In the light emitting device of the present invention, the compound represented by the general formula (P) is contained in the organic layer between the light emitting layer and the cathode, but is preferably contained in a layer adjacent to the cathode.

It is preferable that 70-100 mass% is contained with respect to the total mass of the organic layer to add, and, as for the compound represented by general formula (P), it is more preferable that 85-100 mass% is contained.

(Charge transport layer)

The charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element. Specifically, a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, or an electron injecting layer can be given. Preferably it is a hole injection layer, a hole transport layer, an electron block layer, or a light emitting layer. If the charge transport layer formed by the coating method is a hole injection layer, a hole transport layer, an electron blocking layer, or a light emitting layer, it is possible to manufacture an organic electroluminescent device having low cost and high efficiency. The charge transport layer is more preferably a hole injection layer, a hole transport layer or an electron block layer.

(Hole injection layer, hole transport layer)

The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.

As for the hole injection layer and the hole transport layer, the matters described in paragraphs [0165] to [0167] of JP2008-270736A can be applied to the present invention.

The hole injection layer preferably contains an electron accepting dopant. By including an electron-accepting dopant in the hole injecting layer, the hole injecting property is improved, the driving voltage is lowered, and the efficiency is improved. The electron-accepting dopant may be any of an organic material and an inorganic material as long as it is a material capable of drawing electrons from a material to be doped to generate radical cations. For example, tetracyanoquinomimethane (TCNQ), tetra Fluorotetracyanoquinomethane (F ₄ -TCNQ), molybdenum oxide, and the like.

It is preferable to contain 0.01 mass%-50 mass% with respect to the mass of the whole compound which forms a hole injection layer, and, as for the electron accepting dopant in a hole injection layer, it is more preferable that 0.1 mass%-40 mass% are contained, 0.2 mass%- It is more preferable to contain 30 mass%.

(Electron injection layer, electron transport layer)

The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or cathode side and transporting them to the anode side. The electron injecting material and electron transporting material used in these layers may be a low molecular compound or a high molecular compound.

As an electron transport material, the compound represented by General formula (1) of this invention can be used. Other materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, benzo Imidazole derivatives, imidazopyridine derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, Various metal complexes represented by metal complexes of aromatic ring tetracarboxylic anhydrides such as naphthalene and perylene, phthalocyanine derivatives and 8-quinolinol derivatives, and metal complexes having metal phthalocyanine, benzoxazole or benzothiazole as ligands, Organosilane Derivatives Represented by Silol, Naphthalene, Anthracene, Phenanthrene, Triphenylene It is preferable to select from cyclic hydrocarbon compounds, such as pyrene, and a pyridine derivative, a benzimidazole derivative, an imidazopyridine derivative, a metal complex, and a cyclic hydrocarbon compound.

It is preferable that the thickness of an electron injection layer and an electron carrying layer is 500 nm or less from a viewpoint of reducing a drive voltage, respectively.

As thickness of an electron carrying layer, it is preferable that it is 1 nm-500 nm, It is more preferable that it is 5 nm-200 nm, It is further more preferable that it is 10 nm-100 nm. Moreover, as thickness of an electron injection layer, it is preferable that it is 0.1 nm-200 nm, It is more preferable that it is 0.2 nm-100 nm, It is still more preferable that it is 0.5 nm-50 nm.

The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or a multi-layer structure composed of plural layers of the same composition or different composition.

The electron injecting layer preferably contains an electron donating dopant. Including an electron donating dopant in the electron injecting layer has the effect of improving the electron injecting property, lowering the driving voltage, and improving the efficiency. The electron donating dopant may be any of an organic material and an inorganic material as long as it is capable of imparting electrons to the doped material and generating radical anions. For example, tetrathiafulvalene (TTF) and tetrathia And dihydroimidazole compounds such as naphthacene (TTT) and bis- [1,3diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, cesium and the like.

The electron donating dopant in the electron injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, more preferably 0.1% by mass to 40% by mass, and more preferably 0.5% by mass, based on the total mass of the compound forming the electron injection layer. It is more preferable to contain-30 mass%.

(Hole blocking layer)

The hole block layer is a layer having a function of preventing the holes transported from the anode side to the light emitting layer from escaping to the cathode side. In the present invention, the hole block layer can be formed as an organic layer adjacent to the light emitting layer and the cathode side.

Examples of the organic compound constituting the hole block layer include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (Aluminum (III) bis (2-methyl-8-quinolinato) 4- aluminum complexes such as phenylphenolate (abbreviated as Balq), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-Dimethyl-4,7-diphenyl- And phenanthroline derivatives such as 1,10-phenanthroline (abbreviated as BCP).

As a material which comprises a hole block layer, the compound represented by General formula (1) can be used.

The thickness of the hole block layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, still more preferably 5 nm to 50 nm.

The hole blocking layer may be a single layer structure composed of one or more of the above-described materials, or a multi-layer structure composed of plural layers of the same composition or different compositions.

The material used for the hole block layer is preferably higher than the T ₁ energy of the phosphorescent light emitting material in view of color purity, luminous efficiency and driving durability. To be larger by the state of the film material used for the hole blocking layer T ₁ is at least 0.1 eV greater than T ₁ is preferably a phosphorescent light emitting material, and at least 0.2 eV and preferably greater than it, more than 0.3 eV is more preferable.

(Electronic block layer)

The electron block layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from escaping to the anode side. In the present invention, the electron blocking layer can be formed as the organic layer adjacent to the light emitting layer and the anode side.

As an example of the organic compound which comprises an electron block layer, what was illustrated as the above-mentioned hole transport material is applicable, for example.

As thickness of an electron blocking layer, it is preferable that it is 1 nm-500 nm, It is more preferable that it is 3 nm-100 nm, It is still more preferable that it is 5 nm-50 nm.

The electronic block layer may be a single layer structure composed of one or more of the above-described materials, or a multi-layer structure composed of a plurality of layers of the same composition or different compositions.

The material used for the electron blocking layer is preferably higher than the T ₁ energy of the phosphorescent light emitting material in view of color purity, luminous efficiency and driving durability. It preferred that the T ₁ of the film state of the material used for the electron-blocking layer at least 0.1 eV greater than the T ₁ of the phosphorescent light emitting material, and at least 0.2 eV and preferably greater than it, it is more preferably greater than 0.3 eV.

(Protective layer)

In the present invention, the entire organic EL device may be protected by a protective layer.

About a protective layer, the matter of Paragraph No. [0169]-[0170] of Unexamined-Japanese-Patent No. 2008-270736 can be applied to this invention.

(Bag container)

The element of this invention may seal the whole element using a sealing container.

About the sealing container, the matter described in Paragraph No. [0171] of Unexamined-Japanese-Patent No. 2008-270736 can be applied to this invention.

(Driving)

In the organic electroluminescent device of the present invention, light emission can be obtained by applying a direct current (may include an alternating current component) voltage (usually 2 volts to 15 volts) or a direct current between the anode and the cathode.

As for the driving method of the organic electroluminescent element of the present invention, JP-A-2-148687, JP-A-6-301355, JP-A 5-29080, JP-A-7- 134558, Japanese Patent Application Laid-Open No. Hei 8-234685, Japanese Patent Application Laid-Open No. Hei 8-241047, the driving method described in each specification of Japanese Patent No. 2784615, US Patent No. 5828429, US Patent No. 6023308, etc. are applied. can do.

As external quantum efficiency of the organic electroluminescent element of this invention, 7% or more is preferable, 10% or more is more preferable, 12% or more is more preferable. The external quantum efficiency value can be the maximum value of the external quantum efficiency when the device is driven at 20 ° C, or the value of the external quantum efficiency at around 300 to 400 cd / m2 when the device is driven at 20 ° C. have.

It is preferable that the internal quantum efficiency of the organic electroluminescent element of this invention is 30% or more, 50% or more is more preferable, and 70% or more is more preferable. The internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a typical organic EL device, the light extraction efficiency is about 20%. However, by studying the shape of the substrate, the shape of the electrode, the thickness of the organic layer, the thickness of the inorganic layer, the refractive index of the organic layer, To 20% or more.

(Use of the device of the present invention)

The element of this invention can be used suitably for a display element, a display, a backlight, an electrophotographic, an illumination light source, a recording light source, an exposure light source, a reading light source, a cover, a sign, interior, or optical communication. In particular, it is used suitably for the device driven in the area | region where light emission brightness is high, such as an illumination device and a display device.

(Light emitting device)

Next, the light emitting device of the present invention will be described with reference to FIG.

The light emitting device of the present invention is made using the organic electroluminescent element.

2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention. The light emitting device 20 of FIG. 2 is comprised by the transparent substrate (support substrate) 2, the organic electroluminescent element 10, the sealing container 16, etc. As shown in FIG.

The organic electroluminescent device 10 is constituted by sequentially stacking a positive electrode (first electrode) 3, an organic layer 11, and a negative electrode (second electrode) 9 on a substrate 2. Moreover, the protective layer 12 is laminated | stacked on the cathode 9, and the sealing container 16 is formed on the protective layer 12 via the contact bonding layer 14. As shown in FIG. Further, a part of each of the electrodes 3 and 9, a partition wall, an insulating layer, and the like are omitted.

Here, as the adhesive layer 14, photocurable adhesives, such as an epoxy resin, and a thermosetting adhesive can be used, For example, a thermosetting adhesive sheet can also be used.

The use of the light emitting device of the present invention is not particularly limited, and for example, a display device such as a television, a personal computer, a mobile phone, an electronic paper, and the like can be used.

(Lighting device)

Next, the lighting apparatus of this invention is demonstrated with reference to FIG.

3 is a cross-sectional view schematically showing an example of the lighting apparatus of the present invention. As shown in FIG. 3, the illuminating device 40 of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the illumination device 40 is configured such that the substrate 2 of the organic EL element 10 and the light-scattering member 30 are in contact with each other.

The light scattering member 30 is not particularly limited as long as it can scatter light. In FIG. 3, the light scattering member 30 is a member in which the fine particles 32 are dispersed on the transparent substrate 31. As the transparent substrate 31, a glass substrate is mentioned preferably, for example. As the microparticles | fine-particles 32, transparent resin microparticles | fine-particles are mentioned preferably. As a glass substrate and transparent resin microparticles | fine-particles, a well-known thing can all be used. When the light emission from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30, the lighting device 40 scatters the incident light by the light scattering member 30, and scatters the light. The light is emitted from the light exit surface 30B as illumination light.

Example

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.

1. Synthesis Example (Synthesis Example 1) Synthesis of Compound 1

(56)

4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -1,3,2-dioxaborane 7.08 g (20.0 mmol), m.bromoiobenzene 16.97 g (60.0 mmol), palladium acetate 135 mg (0.60 mmol), triphenylphosphine (PPh) 629 mg (2.40 mmol), sodium carbonate 4.24 g (40.0 mmol), 1,2-dimethoxyethane (DME) 100 ml 50 ml of water was mixed and heated to reflux for 7 hours under a nitrogen atmosphere. After the reaction, water and ethyl acetate were added to extract the organic layer. The organic layer was concentrated under reduced pressure, and then the origin component was removed by silica gel column chromatography (developing solvent: toluene). The solvent was distilled off under reduced pressure, the obtained solid was dissolved in a small amount of methylene chloride, and methanol was added to precipitate a solid. This solid was filtered and 7.33g of synthetic intermediate 2 was obtained by wash | cleaning sequentially with methanol and hexane (yield 96%).

7.20 g (18.8 mmol) of synthetic intermediate 2, 7.16 g (28.2 mmol) of bis (pinacolato) diboron, [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloridedichloromethane complex ( 1: 1) (PdCl ₂ (dppf)) 461 mg (0.56 mmol), potassium acetate (AcOK) 5.54 g (56.4 mmol), and 80 ml of dimethyl sulfoxide (DMSO) were mixed, and it was 70 degreeC under nitrogen atmosphere. Stirred for 4 hours. The reaction solution was poured into ice water, and the precipitated solid was filtered and washed sequentially with pure water and methanol. Thereafter, the origin component was removed by silica gel chromatography (developing solvent: toluene). After distilling off the solvent under reduced pressure, 5.73 g of the synthetic intermediate 3 was obtained by dropping and washing the obtained solid with ethanol (yield 71%).

2.35 g (5.46 mmol) of synthetic intermediate 3, 613 mg (2.60 mmol) of p-dibromobenzene, tris (dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) 71 mg (0.078 mmol) , 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (SPhos) 128 mg (0.312 mmol), potassium phosphate 2.21 g (10.4 mmol), 50 ml of toluene, 20 ml of water were mixed The mixture was heated to reflux for 7 hours under a nitrogen atmosphere. After cooling the reaction solution at room temperature, the precipitate was filtered and washed sequentially with pure water, ethanol and hexane. 1.61g of compounds 1 were obtained by falling toluene and washing the obtained solid 3 times (yield 91%).

Synthesis Example 2 Synthesis of Compound 6

(57)

2.26 g (5.25 mmol) of the synthetic intermediate 3, 3,4'-dibromo1,1'-biphenyl 780 mg (2.50 mmol), tris (dibenzylideneacetone) dipalladium 69 mg (0.075 mmol) ), 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl 123 mg (0.300 mmol), potassium phosphate 2.12 g (10.0 mmol), toluene 50 ml, water 20 ml were mixed, and nitrogen At reflux for 7 hours under the atmosphere. After cooling the reaction solution at room temperature, the precipitate was filtered and washed sequentially with pure water, ethanol and hexane. 1.57g of compounds 6 were obtained by falling toluene and washing the obtained solid 3 times (yield 83%).

Synthesis Example 3 Synthesis of Compound 8

(58)

2.26 g (5.25 mmol) of the synthetic intermediate 3, 3,3'-dibromo1,1'-biphenyl 780 mg (2.50 mmol), tris (dibenzylideneacetone) dipalladium 69 mg (0.075 mmol) ), 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl 123 mg (0.300 mmol), potassium phosphate 2.12 g (10.0 mmol), toluene 50 ml, water 20 ml were mixed, and nitrogen At reflux for 7 hours under the atmosphere. After cooling the reaction solution at room temperature, the precipitate was filtered and washed sequentially with pure water, ethanol and hexane. 1.61g of compounds 8 were obtained by falling toluene and wash | cleaning three times the obtained solid (yield 85%).

[Chemical Formula 59]

Compound 2 was synthesized in the same manner as in Synthesis example 1 except for changing the synthetic intermediate 3 to the synthetic intermediate 4.

Compound 3 was synthesized in the same manner as in Synthesis Example 1 except that Synthetic Intermediate 3 was changed to Synthetic Intermediate 5, and p-dibromobenzene was changed to Synthetic Intermediate 6.

Compound 4 was synthesized in the same manner as in Synthesis example 1 except for changing the synthetic intermediate 3 to the synthetic intermediate 7.

Compound 5 was synthesized in the same manner as in Synthesis Example 1 except that Synthetic Intermediate 3 was changed to Synthetic Intermediate 8 and p-dibromobenzene was synthesized.

Compound 7 was synthesized in the same manner as in Synthesis example 1 except that p-dibromobenzene was changed to synthetic intermediate 9.

Compound 9 was synthesized in the same manner as in Synthesis Example 3 except that Synthetic Intermediate 3 was changed to Synthetic Intermediate 4.

Compound 10 was synthesized in the same manner as in Synthesis example 1 except that p-dibromobenzene was changed to 4,4'-dibromo 1,1'-biphenyl.

Compound 11 was synthesized in the same manner as in Synthesis Example 1 except that Synthetic Intermediate 3 was changed to Synthetic Intermediate 10, and p-dibromobenzene was changed to 5-bromo-2-iodinetoluene.

Compound 12 was synthesized in the same manner as in Synthesis Example 3 except that Synthetic Intermediate 3 was changed to Synthetic Intermediate 10.

All the materials used for element manufacture performed sublimation purification, and it confirmed that the purity (absorption intensity area ratio of 254 nm) was 99.9% or more by high performance liquid chromatography (TOSO TSKgel ODS-100Z).

(Example 1)

A glass substrate having an ITO film of 0.5 mm in thickness and 2.5 cm in width (Geomatec Co., Ltd., surface resistance 10Ω / □ (Ω / sq.)) Was placed in a washing container, ultrasonically cleaned in 2-propanol, and then UV-cured for 30 minutes. Ozone treatment was performed. The following organic compound layers were sequentially deposited on this transparent anode (ITO film) by vacuum deposition.

First layer: HAT-CN: film thickness 10 nm

Second layer: TBDB: film thickness 27 nm

Third layer: HT-1: film thickness 3 nm

Fourth layer: The dope concentration of the host material and GD-1 (mass ratio 90:10), ie, GD-1, shown in Table 1 is 10 mass%: film thickness 30 nm.

5th layer: HBL material described in Table 1: film thickness 5 nm

Sixth layer: Alq: film thickness 45 nm

On this, 0.1 nm of lithium fluoride and 100 nm of metallic aluminum were deposited in this order to obtain a cathode.

The obtained laminated body was put into the glove box substituted with nitrogen gas, without contacting air | atmosphere, and it sealed using the glass sealing can and an ultraviolet curable adhesive (XNR5516HV, Nagase Chiba Co., Ltd.), and the elements 1-1 to 1 -9 and the comparative elements 1-1 to 1-5 were obtained. Tables 1 and 2 show the results obtained by evaluating these devices in terms of drive voltage, durability, efficiency change during high luminance driving, color change during high luminance driving, and change in efficiency for dope concentration change. Moreover, in Comparative element 1-6, since the comparative compound 6 could not be formed into a film by the vacuum vapor deposition method, an element could not be manufactured.

(a) driving voltage

Each element is made to emit light by applying a DC voltage such that the luminance is 1000 cd / m 2. The applied voltage at this time was used as an index for driving voltage evaluation. The smaller the number is, the more preferable the driving voltage is.

(b) driving durability

A DC voltage was applied to each element to emit light using a Toyo Technica source major unit 2400, and the luminance thereof was measured using a top meter manufactured luminance meter BM-8. The emission spectrum and emission wavelength were measured using the Hamamatsu Photonics spectrum analyzer PMA-11. Each element was continued to emit light by applying a DC voltage so that the luminance became 5000 cd / m 2, and the time required until the luminance became 4000 cd / m 2 was used as an index of durability. In Table 1, the value of element 1-1 is shown in Table 3, the value of element 2-1 is shown in Table 3, the value of element 3-1 is shown in Table 4, and the value of element 4-1 is shown in Table 6, Table 7 In Table 8, the value of the element 5-1 was set to 1.0, and the value of the element 6-1 was set to 1.0. Durability is so preferable that a number is large.

(c) Efficiency change during high brightness driving

Each element was made to emit light by applying a direct current voltage such that the luminance was 50000 cd / m 2. The external quantum efficiency η ₅₀₀₀₀ at this time was calculated by the luminance conversion method, and the ratio (η ₅₀₀₀₀ / η ₁₀₀₀ ) to the external quantum efficiency η ₁₀₀₀ at the time of emitting light by applying a DC voltage such that the luminance was 1000 cd / m 2 was obtained. It was set as the index of the efficiency change at the time of high brightness drive. The larger this value is, the more preferable.

(d) Chromaticity change during high brightness driving

Each element is made to emit light by applying a DC voltage such that the luminance is 50000 cd / m 2. At this time, the chromaticity (x, y) ₅₀₀₀₀ is compared with the chromaticity (x, y) ₁₀₀₀ when a direct current voltage is applied so that the luminance is 1000 cd / m 2 and emits light. It expressed in the form of ((DELTA) x, (DELTA) y), and made it into the index of the chromaticity change at the time of high brightness drive. The smaller the values of Δx and Δy are, the more preferable.

(e) Efficiency change with respect to dope concentration change

External quantum efficiency (η _5% , η _{15%) at} a luminance of 1000 cd / m 2 of the device manufactured by making the dope concentration of the light emitting material GD-1 in the fourth layer (light emitting layer) 5 mass% and 15 mass%. ) And the ratio (η _5% / η _10% , η _15% / η ₁₀ ) to the external quantum efficiency (η _10% ) at a luminance of 1000 cd / m 2 of the device manufactured with a dope concentration of 10 mass%. _% ) Was used as an index of the efficiency change with respect to the dope concentration change. The closer to 1.0 this value is, the better.

In addition, in Table 2, the efficiency change of the element manufactured by changing the dope density | concentration of the luminescent material about the elements 1-1 to 1-6, comparative elements 1-2, and 1-4 in Table 1 was shown.

Moreover, in Table 5, the efficiency change of the element manufactured by changing the dope density | concentration of the luminescent material about the elements 3-1 to 3-4 and the comparative elements 3-1 to 3-3 in Table 4 was shown.

(Example 2)

Except having changed the layer structure to what is shown below, the element was manufactured like Example 1, and the result of having performed evaluation similar to Example 1 about drive voltage and drive durability is shown in Table 3.

First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm

Second layer: NPD: film thickness 5 nm

Third layer: HT-2: film thickness 3 nm

Fourth layer: H-1 and GD-2 (mass ratio 85:15): film thickness 30 nm

Fifth layer: HBL material described in Table 3: Film thickness 10 nm

Sixth layer: ET-2: film thickness 20 nm

(Example 3)

Except having changed the layer structure to what is shown below, the element was manufactured like Example 1, and the result of having evaluated similarly to Example 1 is shown in Table 4. FIG.

First layer: CuPc: film thickness 10 nm

Second layer: NPD: film thickness 30 nm

Third layer: host material and RD-1 (mass ratio 90: 10) described in Table 4: film thickness 30 nm

Fourth layer: ET-3: film thickness 50 nm

(Example 4)

Except having changed the layer structure to what is shown below, the element was manufactured like Example 1, and the result of having evaluated similarly to Example 1 about drive voltage and drive durability is shown in Table 6. FIG.

First layer: TCTA: film thickness 35 nm

Second layer: HT-2: film thickness 5 nm

Third layer: BAlq and RD-2 (mass ratio 90: 10): film thickness 30 nm

Fourth layer: HBL material described in Table 6: Film thickness 5 nm

Fifth layer: ET-4: film thickness 45 nm

(Example 5)

Except having changed the layer structure to what is shown below, the element was manufactured like Example 1, and the result of having evaluated similarly to Example 1 about drive voltage and drive durability is shown in Table 7.

First layer: HAT-CN: film thickness 10 nm

Second layer: NPD: film thickness 115 nm

Third layer: TPAC: film thickness 5 nm

4th layer: H-2 and Firpic (mass ratio 90:10): film thickness 30 nm

Fifth layer: HBL material described in Table 7: film thickness 5 nm

Sixth layer: BAlq: film thickness 25 nm

(Example 6)

Except having changed the layer structure to what is shown below, the element was manufactured like Example 1, and the result of having performed evaluation similar to Example 1 about drive voltage and drive durability is shown in Table 8.

First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 120 nm

Second layer: NPD: film thickness 7 nm

Third layer: HT-2: film thickness 3 nm

Fourth layer: H-3 and BD-1 (mass ratio 85:15): film thickness 30 nm

5th layer: HBL material described in Table 8: film thickness 5 nm

Sixth layer: BAlq: film thickness 25 nm

(60)

(61)

[Formula 62]

(63)

&Lt; EMI ID =

The maximum light emission wavelength of the light emitting material is as follows.

RD-1: 625 nm

RD-2: 630 nm

GD-1: 525 nm

GD-2: 505 nm

Firpic: 475 nm

BD-1: 460 nm

Industrial availability

According to the present invention, it is possible to provide an organic electroluminescent device having a low driving voltage, excellent durability, low efficiency in high-brightness driving, small chromaticity change, and small fluctuation in device characteristics due to dope concentration change.

Although this invention was detailed also demonstrated with reference to the specific embodiment, it is clear for those skilled in the art that various changes and correction can be added without deviating from the mind and range of this invention.

This application is based on the JP Patent application (patent application 2010-231030) for which it applied on October 13, 2010, and the Japanese patent application (Patent application 2010-244820) for which it applied on October 29, 2010, The content here Is taken as a reference.

2: substrate
3: anode
4: Hole injection layer
5: hole transport layer
6: light emitting layer
7: Hole block layer
8: Electron transport layer
9: cathode
10: Organic electroluminescent device
11: Organic layer
12: Protective layer
14: Adhesive layer
16: Encapsulation container
20: Light emitting device
30: light scattering member
31: transparent substrate
30A: light incidence surface
30B: light emitting surface
32: particulate
40: Lighting device

Claims (18)

An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode on a substrate, and at least one organic layer including a light emitting layer between the electrodes,
The organic electroluminescent element containing the compound represented by following General formula (1) in any at least one layer of the said at least one organic layer.
[Formula 1]

(In General formula (1), R <_0> represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently, n represents the integer of 1-4. Moreover, phenylene groups Are all meta or para, and when n = 1 all three phenylene groups are linked by para.
R _A , R _B and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a halogen atom, or a group obtained by combining these. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different.
a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3 each independently.) The method of claim 1,
The organic electroluminescent element whose compound represented by the said General formula (1) is a compound represented by either of following General formula (2)-(4).
(2)

(In General Formula (2)-(4), R represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently.) 3. The method according to claim 1 or 2,
In general formula (1), R <_0> is an alkyl group, or in any of general formula (2)-(4), R is an organic group, The organic electroluminescent element. 3. The method according to claim 1 or 2,
The organic electroluminescent element whose m is 0 in any one of general formula (1)-(4). The method according to any one of claims 1 to 4,
The organic electroluminescent element whose molecular weight of the compound represented by any of General formula (1)-(4) is 1000 or less. 6. The method according to any one of claims 1 to 5,
An organic electroluminescent element comprising at least one phosphorescent light emitting material in a light emitting layer. The method according to claim 6,
An organic electroluminescent device, wherein the phosphorescent material is represented by the following general formula (E-1).
(3)

(In General Formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.
A ₁ represents a group of atoms which together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms.
B ₁ represents an atomic group which forms a 5 or 6 membered ring together with Z ² and a carbon atom.
(XY) represents a monoanionic ligand.
n _E1 represents an integer of 1 to 3.) The method of claim 7, wherein
The organic electroluminescent element in which the phosphorescence emitting material represented by said general formula (E-1) is represented with the following general formula (E-2).
[Chemical Formula 4]

(In General Formula (E-2), A ^E1 to A ^E8 each independently represent a nitrogen atom or CR ^E.
R ^E represents a hydrogen atom or a substituent.
(XY) represents a monoanionic ligand.
n _E2 represents an integer of 1 to 3.) 9. The method according to claim 7 or 8,
The organic electroluminescent element whose maximum light emission wavelength of the phosphorescence emitting material represented by said general formula (E-1) is 500 nm-700 nm. 10. The method according to any one of claims 1 to 9,
The organic electroluminescent element containing the compound represented by the said General formula (1) in a light emitting layer. 11. The method according to any one of claims 1 to 10,
The organic electroluminescent element which contains the compound represented by the said General formula (1) in the positive hole block layer which is between the said light emitting layer and the said cathode, and adjoins the said light emitting layer. The light-emitting device containing the organic electroluminescent element of any one of Claims 1-11. The display device containing the organic electroluminescent element in any one of Claims 1-11. The illuminating device containing the organic electroluminescent element of any one of Claims 1-11. The charge transport material containing the compound represented by General formula (1).
[Chemical Formula 5]

(In General formula (1), R <_0> represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently, n represents the integer of 1-4. Moreover, phenylene groups Are all meta or para, and when n = 1 all three phenylene groups are linked by para.
R _A , R _B and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a halogen atom, or a group obtained by combining these. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different.
a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3 each independently.) The charge transport material which consists of a compound represented by any of following General formula (2)-(4).
[Chemical Formula 6]

(In General Formula (2)-(4), R represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently.) The compound represented by general formula (1).
(7)

(In General formula (1), R <_0> represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently, n represents the integer of 1-4. Moreover, phenylene groups Are all meta or para, and when n = 1 all three phenylene groups are linked by para.
R _A , R _B and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a halogen atom, or a group obtained by combining these. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different.
a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3 each independently.) The compound represented by any of the following general formulas (2)-(4).
[Chemical Formula 8]

(In General Formula (2)-(4), R represents an aryl group which consists only of an alkyl group or a monocyclic ring each independently. M represents the integer of 0-4 each independently.)

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