KR20140090411A - Asymmetric antracene derivatives having two naphthyl groups and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to antracene derivatives represented by [Formula A] and [Formula B], and an organic light-emitting diode including the same. Substituents X_1 to X_14, Y, and Z are the same as defined in the detailed description.

Description

[0001] The present invention relates to an asymmetric anthracene derivative having two naphthyl groups and an organic light emitting device comprising the same. [0002] Asymmetric anthracene derivatives having two naphthyl groups and organic light-

The present invention relates to an asymmetric anthracene derivative having two naphthyl groups and an organic light emitting device comprising the same. More particularly, the present invention relates to an asymmetric anthracene derivative capable of lowering a driving voltage and exhibiting an excellent luminescent efficiency, To an organic light emitting device.

In recent years, the demand for a flat display device having a small space occupation has been increasing due to the enlargement of a display device. The liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT (cathode ray tube) angle is limited and a back light is necessarily required. In contrast, an organic light emitting diode (OLED), a new flat display device, is a display using an auto-luminescent phenomenon and has advantages such as a large viewing angle, a light weight and a small size compared to a liquid crystal display, In recent years, application to a full-color display or illumination is expected.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light-emitting material in order to increase the light-emitting efficiency through the light-emitting layer.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

In order for the organic luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material Should be preceded.

On the other hand, in the organic light emitting device, the charges injected from both electrodes are recombined in the light emitting layer to emit light, and the moving speed of the holes is faster than the electron moving speed, so that the efficiency deterioration due to part of the holes escaping from the light emitting layer . Therefore, an electron transporting material having a high electron-transporting speed is required.

In order to produce an organic compound having excellent electron transporting ability and hole blocking ability, excellent light emitting efficiency and high stability in a thin film state, in Registration No. 10-0691543 (Mar. 3, 2007), an anthracene- Discloses organic compounds having one or two hetero-functional groups incorporated therein, and JP-A-10-2012-0104204 (2012.09.20) describes an organic compound in which a pyridone indole derivative is bonded to a substituted anthracene ring structure And JP-A-2010-168363 (Aug. 5, 2010) discloses an anthracene derivative having a pyridine naphthyl group, which has excellent characteristics of external quantum efficiency and driving voltage.

However, in spite of efforts to manufacture an electron transporting material for an organic light emitting device, development of a material for low driving voltage and high luminous efficiency is not sufficient, There is a continuing need for the development of an excellent material for an electron transport layer for an organic light emitting device.

Patent Registration No. 10-0691543 (Mar. 3, 2007)

Japanese Patent Application Laid-Open No. 10-2012-0104204 (2012.09.20)

Japanese Unexamined Patent Application Publication No. 2010-168363 (Aug. 05, 2010)

Therefore, the first technical object of the present invention is to provide an organic compound for an organic light emitting device which can be used for an electron transporting layer and has a low voltage driving characteristic and an excellent luminous efficiency.

A second object of the present invention is to provide an organic light emitting device including the organic compound.

In order to achieve the first technical object, the present invention provides an anthracene derivative represented by the following formula (A) or (B) as an organic compound that can be used in an electron transport layer of an organic light emitting device.

[Chemical Formula A]

In the above formulas (A) and (B)

Y is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted group having 1 to 50 carbon atoms A substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms,

Z is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms Lt; / RTI >group;

m and m 'are integers of 1 to 8;

Each of X ₁ to X ₁₄ is the same or different and is independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 aryl A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroatom having O, N or S A heteroaryl group of a small number of 2 to 50, a cyano group, a nitro group, and any one selected from the group consisting of halogen group, may form a fused ring group of aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other;

In the above formula (A), X ₁ To X ₇ And at least one of X ₈ To X < ₁₄ > is a heteroaryl group having 2 to 20 carbon atoms each containing a nitrogen atom.

According to another aspect of the present invention, there is provided a plasma display panel comprising a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, An organic light emitting device comprising at least one anthracene derivative represented by the formula (A) or (B).

According to the present invention, an anthracene derivative represented by the formula (A) or (B) has characteristics of driving at a low voltage as compared with a conventional material and has a superior luminescence efficiency and can be used for the production of a stable and excellent device have.

1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

The present invention provides an anthracene derivative which can be used in an electron transporting layer or a light emitting layer of an organic light emitting device, and which is represented by the following formula (A) or (B).

[Chemical Formula A]

In the above formulas (A) and (B)

Y is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group,

Z is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms Lt; / RTI >group;

m and m 'are integers of 1 to 8;

When the substituents Y and Z are not bonded to the carbon of the aromatic ring of the naphthyl group or the anthracenyl group, hydrogen is bonded;

Each of X ₁ to X ₁₄ is the same or different and is independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 aryl A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroatom having O, N or S A heteroaryl group of a small number of 2 to 50, a cyano group, a nitro group, and any one selected from the group consisting of halogen group, may form a fused ring group of aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other;

At least one of X ₁ to X ₇ in the above formula (A) and at least one of X ₈ to X ₁₄ in the formula (B) is a heteroaryl group having 2 to 20 carbon atoms and each of which contains a nitrogen atom;

The 'substituted' in the above 'substituted or unsubstituted' means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , An alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 1 to 24 carbon atoms.

The aryl group used in the compound of the present invention means an aromatic system composed of a hydrocarbon containing at least one ring. When the substituent is present, the adjacent substituent may be fused with each other to form a ring.

Specific examples of the aryl group include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl and the like. At least one hydrogen atom of the aryl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, , An amino group (-NH ₂ , -NH (R), -N (R ') (R "), R' and R" are independently an alkyl group having 1 to 10 carbon atoms and in this case an "alkylamino group" An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms , A heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group, which is a substituent used in the compounds of the present invention, refers to a C 2 -C 24 ring aromatic system containing 1, 2 or 3 heteroatoms selected from N, O, P or S and the remaining ring atoms are carbon, The rings may be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like. The atom may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, Butylsilyl, dimethylpurylsilyl and the like, and at least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

More preferably, in the present invention, at least one of X ₁ to X ₇ and at least one of X ₈ to X ₁₄ in the above-mentioned formulas (A) and (B) is a hetero ring having 2 to 20 carbon atoms When the aryl group is an aryl group, the heteroaryl group may be any one substituent selected from the structural formulas 1 to 6. [

[Structural formula 1]

[Structural formula 2]

[Structural Formula 3]

[Structural Formula 4]

[Structural Formula 5]

 [Structural Formula 6]

In the formulas 1 to 6, T ₁ to T ₈ are the same or different and independently of one another are C (R ₁₁ ), C (R ₁₁ ) (R ₁₂ ), N, N (R ₁₃ ) S; Wherein R ₁ to R ₁₃ are the same or different from each other and independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a heteroaryl group having 2 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S, a cycloalkyl group having 3 to 30 carbon atoms, In each of Structural Formulas ₁ to 6, one of R ₁ to R ₁₃ may be a single bond forming a bond with the naphthyl group in Formulas A and B above.

Here, the formula 3 may include a compound represented by the formula 3-1 by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

Provided that T ₁ to T ₅ and R ₃ and R ₄ are the same as defined above.

In the present invention, when at least one of X ₁ to X ₇ and X ₈ to X ₁₄ in the formula [B] is a heteroaryl group having 2 to 20 carbon atoms and contains a nitrogen atom, The heteroaryl group may have a plurality of rings. When the heteroaryl group has a plurality of rings, it is considered that all the rings are composed of heteroaryl containing nitrogen, or a ring of a heteroaryl moiety containing nitrogen and a ring of aryl moieties not containing a heteroatom Can be. In this case, the moiety bonded to the naphthyl group of the formula (A) or (B) may be a ring moiety including nitrogen, or may be a ring of an aryl moiety not containing nitrogen.

If T ₁ to T ₃ have at least one nitrogen atom and T ₄ , T ₅ , R ₃ and R ₄ are an aryl group moiety not containing nitrogen in the case of the structural formula 3, The moiety bonded to the naphthyl group of the formula (A) or (B) may be any one of T ₁ to T ₃ , or any one selected from T ₄ , T ₅ , R ₃ and R ₄ may be bonded to the naphthyl group .

In this case, more preferably, the ring of the aryl group moiety not containing nitrogen may be a moiety bonded to the naphthyl group of the above formula (A) and (B).

This can be similarly understood in the above-mentioned [Structural formulas 4] to [Structural formula 6].

In the present invention, Y and Z in the above-mentioned [Formula A] and [Formula B] are the same or different, and independently of each other, hydrogen, deuterium; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 5 to 20 carbon atoms; , And m and m 'may each be an integer of 1 to 4.

In this case, only one of the substituents X ₁ to X ₇ in the above-mentioned formula (A) of the present invention is any substituent selected from the structural formulas 1 to 6, and only one of the substituent groups X ₈ to X ₁₄ May be any one substituent selected from the structural formulas (1) to (6).

In the present invention, each of the substituents in the structural formulas 1 to 6 may be substituted with 1 to 3 nitrogen atoms in the aromatic carbon residue in the substituent to form a heteroaryl group.

When the nitrogen atom is contained in the aromatic carbon site, the nitrogen atom can make the aromatic ring system in a state lacking electrons and can serve as an electron transport layer.

More specifically, in the present invention, the substituent X ₁ To X ₇ And at least one of substituent X ₈ of formula (B) To X < ₁₄ > may each be any one of substituents 101 to 606 shown below.

[Substituent 101] [Substituent 102] [Substituent 103]

[Substituent group 104] [Substituent group 105] [Substituent group 106]

[Substituent group 107] [Substituent group 108] [Substituent group 109]

[Substituent group 110] [Substituent group 111] [Substituent group 112] [Substituent group 113]

[Substituent group 201] [Substituent group 202] [Substituent group 203]

[Substituent group 204] [Substituent group 205] [Substituent group 206]

[Substituent 207] [Substituent 208]

[Substituent group 301] [Substituent group 302] [Substituent group 303]

[Substituent group 304] [Substituent group 305] [Substituent group 306]

[Substituent group 307] [Substituent group 308]

[Substituent 401] [Substituent 402] [Substituent 403]

[Substituent group 404] [Substituent group 405] [Substituent group 406]

[Substituent group 407] [Substituent group 408] [Substituent group 409]

[Substituent group 410] [Substituent group 411] [Substituent group 412] [Substituent group 413]

[Substituent group 501] [Substituent group 502] [Substituent group 503]

[Substituent 601] [Substituent 602] [Substituent 603]

[Substituent 604] [Substituent 605] [Substituent 606]

Wherein R is the same or different and is independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, Or an unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted (having 6 to 60 carbon atoms) amino group, a di (substituted or unsubstituted) alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and each of May be fused to adjacent groups to form a ring,

n is an integer of 0 to 9,

When the substituent R is not bonded to the carbon of the aromatic ring in the heteroaryl group of the substituents 101 to 606, hydrogen is bonded,

And one of the Rs is a single bond bonded to the naphthyl group of the above [Formula A] and [Formula B].

In this case, in the present invention, only one of X ₁ to X ₇ in the formula (A) is any one substituent selected from the substituents 101 to 606, and only one of the substituents X ₈ to X ₁₄ in the formula (B) May be any one substituent selected from substituents 101 to 606. [

The present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one of the anthracene derivatives of the present invention.

In the present invention, "(organic layer) includes one or more compounds "," (organic layer) may include one kind of compound belonging to the scope of the present invention or two or more different compounds belonging to the category of the above compound Can be interpreted as "exist".

 At this time, the organic layer containing the compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.

In the present invention, the organic layer interposed between the first electrode and the second electrode may include an electron transporting layer and a light emitting layer. In this case, the anthracene derivative of the present invention is contained in an electron transporting layer, Lt; / RTI >

In the present invention, specific examples of the dopant material used in the light emitting layer include pyrene-based compounds, deuterium-substituted pyrene-based compounds, fluorene-based compounds, deuterium-substituted fluorene-based compounds, benzofluorene- Benzene fluorene compound, dibenzofluorene compound, deutero-substituted dibenzofluorene compound, indenophenanthrene compound, deuterium-substituted indenophenanthrene compound, arylamine, deuterium-substituted arylamine, , Deuterated substituted peryl-based compounds, pyrrole-based compounds, deutero-substituted pyrrole-based compounds, hydrazone based compounds, deuterated substituted hydrazone based compounds, carbazole based compounds, deuterated substituted carbazole based compounds, stilbene based compounds, A starburst-based compound, a deuterium-substituted starburst-based compound, an oxadiazole-based compound, But are coumarin hydrogen substituted oxadiazole-based compound, (coumarine), deuterium-substituted coumarin (coumarine), the present invention is not limited thereby.

As the host used in the light emitting layer, Alq ₃ , CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole) (Naphthalen-2-yl) anthracene (ADN), TCTA, TPBI (1,3,5-tris (N-phenylbenzimidazole-2 (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), E3, DSA (distyrylarylene), dmCBP Deuterium substituents of host compounds, and the like, but are not limited thereto.

PVK ADN

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

In the present invention, when the anthracene derivative is used in an electron transporting layer, the electron transporting layer may contain other kinds of electron transporting compounds in addition to the anthracene derivative of the present invention.

Herein, a compound for an electron transport layer different from the anthracene derivative is an anthracene derivative having a structure of [Formula A] and [Formula B], but may be a compound of a different kind, or a compound represented by Formula [A] An anthracene derivative having no structure of [Formula A] or [Formula B] may be used as another electron transport layer compound.

As the compound for an electron transporting layer having no structure represented by the above formula (A) or (B), an oxadiazole derivative such as PBD, BMD, BND, Liq, Alq ₃ or a compound having a structure represented by the following formula .

≪ RTI ID = 0.0 &

In the above formula (C)

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M A ligand chelated by coordination bond with the single bond, and

Wherein M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom, and OA is a monovalent ligand capable of single bond or coordination bond with M,

O is oxygen,

A represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2 to C20 Substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, and substituted or unsubstituted hetero atoms having 2 to 50 carbon atoms having O, N or S, An aryl group,

M is 1 and n is 0 when M is a metal selected from an alkali metal,

M = 1, n = 1, or m = 2 and n = 0 when M is a metal selected from alkaline earth metals,

M is from 1 to 3 when M is boron or aluminum, and n is any of from 0 to 2, and m + n = 3;

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, An aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

In the present invention, Y may be the same or different and independently of each other may be any one selected from the following formulas [C1] to [C39], but is not limited thereto.

[Structural formula C1] [Structural formula C2] [Structural formula C3]

[Structural formula C4] [Structural formula C5] [Structural formula C6]

[Structural formula C7] [Structural formula C8] [Structural formula C9] [Structural formula C10]

[Structural formula C11] [Structural formula C12] [Structural formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structural formula C17] [Structural formula C18] [Structural formula C19] [Structural formula C20]

[Structural formula C21] [Structural formula C22] [Structural formula C23]

[Structural formula C24] [Structural formula C25] [Structural formula C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structural formula C31] [Structural formula C32] [Structural formula C33]

[Structural formula C34] [Structural formula C35] [Structural formula C36]

[Structural formula C37] [Structural formula C38] [Structural formula C39]

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

When the anthracene derivative in the present invention is mixed with other electron transporting compounds and used in an electron transporting layer, the mixing ratio thereof is 10:90 to 90:10 by weight, preferably 25:75 to 90:10, 75:25.

In the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular deposition method or a solution process, The organic light emitting element can be used for a display element, a display element, or a monochromatic or white illumination element.

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

1 is a cross-sectional view showing the structure of an organic light emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60, and a cathode 80, An injection layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, the organic light emitting device of the present invention and a method of manufacturing the same will be described below. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

The hole injection layer material is not particularly limited as long as it is conventionally used in the art. For example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- ], Etc. However, the present invention is not limited thereto.

The material for the hole transport layer is not particularly limited as long as it is commonly used in the art and includes, for example, N, N'-bis (3-methylphenyl) -N, N'- -Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (a-NPD). However, the present invention is not necessarily limited thereto.

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

The light emitting layer may be made of a host and a dopant.

Further, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM.

At this time, the dopant used in the light emitting layer may be a compound represented by the following formula (1) or (2).

[Chemical Formula 1] < EMI ID =

Among the above-mentioned formulas (1) and (2)

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, an optionally substituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having O, N or S as a hetero atom, preferably an anthracene, pyrene, phenanthrene, indenophenanthrene, klysene, naphtha Phenylene, perylene, and pentacene.

At this time, A may be a compound represented by the following formulas (A1) to (A10).

[Chemical Formula A1] [Chemical Formula A2] [Chemical Formula A3] Chemical Formula A4 [Chemical Formula A5]

(A9) a compound of the formula (A10)

Wherein Z ₁ to Z ₂ in the formula [A3] are each independently selected from the group consisting of hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted Or an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C60 alkylamino group, , (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, and Z ₁ to Z ₂ are the same or different from each other and can form a condensed ring with adjacent groups.

In the above formula (1)

X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other,

Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted Or a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen. more selected species and, Y ₁ to Y ₂ each are the same or different each other, may form a fused ring group of the aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other It was.

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

In the above formula (2)

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form, Each of which may be substituted with deuterium or alkyl, and may be the same as or different from each other.

The B Is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, R ₅ and R ₆ are the same or different from each other;

Wherein _{R 1, R 2, R 3} , R 5 and R ₆ are, each independently, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, Or beach (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a di (substituted or unsubstituted) alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms,

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and R ₃ Each R ₃ may be in fused form, and n is an integer from 1 to 4.

The amine group bonded to A in the formulas (1) and (2) may be represented by any one selected from the group consisting of the following [substituents 1] to [52], but is not limited thereto.

[Substituent 1] [Substituent 2] [Substituent 3] [Substituent 4]

[Substituent group 5] [Substituent group 6] [Substituent group 7] [Substituent group 8]

[Substituent group 9] [Substituent group 10] [Substituent group 11] [Substituent group 12]

[Substituent group 13] [Substituent group 14] [Substituent group 15] [Substituent group 16]

[Substituent group 17] [Substituent group 18] [Substituent group 19] [Substituent group 20]

[Substituent group 21] [Substituent group 22] [Substituent group 23] [Substituent group 24]

[Substituent 25] [Substituent 26]

[Substituent group 27] [Substituent group 28] [Substituent group 29] [Substituent group 30]

[Substituent group 31] [Substituent group 32] [Substituent group 33] [Substituent group 34]

[Substituent group 35] [Substituent group 36] [Substituent group 37] [Substituent group 38]

[Substituent group 39] [Substituent group 40] [Substituent group 41] [Substituent group 42]

[Substituent group 43] [Substituent group 44] [Substituent group 45] [Substituent group 46]

[Substituent group 47] [Substituent group 48] [Substituent group 49] [Substituent group 50]

[Substituent group 51] [Substituent group 52]

In the above substituents, R may be the same or different and independently of one another selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms , A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a di (substituted or unsubstituted C1-C60 alkyl) amino group, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, , Each of which may be substituted from 1 to 12, and each substituent may form a condensed ring with adjacent groups.

In the present invention, the host may be a compound represented by the following general formula (1A) to (1D).

≪ EMI ID =

In the above formula (1A)

Ar _7, Ar ₈ and Ar ₉ are the same or different and each independently represents a single bond, a substituted or unsubstituted C ₅ -C ₆₀ aromatic linking group, or a substituted or unsubstituted C ₂ -C ₆₀ A heteroaromatic linking group;

R ₂₁ to R ₃₀ are the same or different from each other and each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group, A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, A substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, a di (substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, Or an unsubstituted aryl group having 6 to 60 carbon atoms) amino group, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron Each substituent may form a fused ring with the adjacent groups;

E, f and g are the same as or different from each other and each independently 0 or an integer of 1 to 4;

The two sites indicated by * in the anthracene may be the same as or different from each other, and may independently form an anthracene derivative selected from the following formulas (1Aa-1) to (1Aa-3) in combination with the P or Q structure.

[Chemical Formula 1Aa-1] [Chemical Formula 1Aa-2] Chemical Formula 1Aa-3]

The 'substituted' in the 'substituted or unsubstituted' refers to a group selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group having 1 to 24 carbon atoms, an arylsilyl group, and an aryloxy group having 1 to 24 carbon atoms.

≪ RTI ID = 0.0 &

In the above formula (1B)

Wherein Ar ₁₇ to Ar ₂₀ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ in Formula 1A, and R ₆₀ to R ₆₃ are the same as defined in R ₂₁ to R ₃₀ in Formula 1A Lt; / RTI >

W and ww are the same as or different from each other, x and xx are the same as or different from each other, w + ww and x + xx are the same or different from each other and independently an integer of 0 to 3; Y and yy are the same or different, and z and zz are the same or different from each other, y + yy to z + zz are not more than 2, and each is an integer of 0 to 2;

[Chemical Formula 1C]

In the above formula (1C)

Wherein Ar ₂₁ to Ar ₂₄ are the same or different and are made of the same substituents as defined for Ar ₇ to Ar ₈ in the (1A) each independently from each other, wherein R ₆₄ to R ₆₇ is at R ₂₁ to R ₃₀ of Formula 1A Lt; / RTI > is as defined above.

The above ee to hh are the same as or different from each other, and each independently is an integer of 1 to 4, and the above-mentioned II to 11 are the same or different and independently an integer of 0 to 4.

[Chemical Formula 1D]

In the above formula (1D)

Wherein Ar ₂₅ to Ar ₂₇ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ in formula (1A), and R ₆₈ to R ₇₃ are the same or different from each other, The substituent groups are the same as defined in R ₂₁ to R ₃₀ of 1 A, and each substituent may form a saturated or unsaturated cyclic structure adjacent to each other. In addition, the mm to ss are the same or different from each other and each independently an integer of 0 to 4.

More specifically, the host may be represented by any one selected from the group consisting of the following [compounds 1] to [56], but is not limited thereto.

[Compound 1] [Compound 2] [Compound 3] [Compound 4]

[Compound 5] [Compound 6] [Compound 7] [Compound 8]

[Compound 9] [Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15] [Compound 16]

[Compound 17] [Compound 18] [Compound 19] [Compound 20]

[Compound 21] [Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27] [Compound 28]

[Compound 29] [Compound 30] [Compound 31] [Compound 32]

[Compound 33] [Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39] [Compound 40]

[Compound 41] [Compound 42] [Compound 43] [Compound 44]

[Compound 45] [Compound 46] [Compound 47] [Compound 48]

[Compound 49] [Compound 50] [Compound 51] [Compound 52]

[Compound 53] [Compound 54] [Compound 55] [Compound 56]

The light emitting layer may further include various dopants and various hosts as well as the dopant and the host.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

<Examples>

Synthesis Example 1. Synthesis of [Compound 1]

Synthesis Example 1-1 Synthesis of (10- (naphthalen-2-yl) anthracene-9-yl) boronic acid

Synthesis Example 1-1-a) Synthesis of 9- (naphthalen-2-yl) anthracene

2-naphthalene boronic acid 29.9 g (174 mmol), 9- bromo-anthracene 37.4 g (145 mmol), 40.3 g of potassium carbonate (290 mmol), Pd (PPh 3) 4 3.3 g (2 mmol) in a round bottom flask, 80 ml of water, 200 ml of toluene and 200 ml of tetrahydrofuran were placed and subjected to a reflux reaction.

After completion of the reaction, the layers were separated to remove the water layer, and the organic layer was concentrated under reduced pressure to obtain 30 g (yield 80%) of 9- (naphthalene-2-yl) anthracene by column chromatography.

Synthesis Example 1-1-b) Synthesis of 9-bromo-10- (naphthalen-2-yl) anthracene

30 g (0.119 mol) of 9- (naphthalen-2-yl) anthracene prepared in Synthesis Example 1-1-a) and 270 ml of dichloromethane were placed in a round bottom flask and the crystals were dissolved at room temperature. After that, 19 g (0.118 mol) of bromine was diluted in 50 ml of dichloromethane and reacted slowly. After completion of the reaction, the layers were separated to remove the water layer, and the organic layer was concentrated under reduced pressure to precipitate crystals with methanol, and then recrystallized to obtain 28.6 g (yield: 77%) of yellow 9-bromo-10- (naphthalen- ) Was obtained

Synthesis Example 1-1-c) Synthesis of (10-naphthalen-2-yl) anthracene-9-yl) boronic acid

9-bromo-10- (naphthalen-2-yl) anthracene (28.6 g, 75 mmol) prepared in Synthesis Example 1-1-b was dissolved in 230 mL of THF in a round bottom flask. N-Butyllithium (56 mL) was added slowly while cooling to -78 ° C. After the addition, trimethylborate (36.4 g, 105 mmol) was added at -78 ° C for 1 hour. After stirring at -78 ° C for 1 hour, the mixture was stirred at room temperature for 2 hours, and 2N aqueous hydrochloric acid solution was added to adjust the acidity. The solvent was removed by extraction with EA, and crystals were obtained with hexane to obtain 19.8 g (yield: 75%) of (10-naphthalene-2-yl) anthracene-9-yl) boronic acid.

Synthesis Example 1-2) Synthesis of 8-iodonaphthalen-2-yl trifluoromethanesulfonate

Synthesis Example 1-2-a) Synthesis of 8-iodo-2-naphthol

Scheme 1-2-a)

100 g (628 mmol) of 8-amino-2-naphthol is dissolved in 300 mL of acetic acid, cooled to 0 ° C, and 200 mL of sulfuric acid is slowly added dropwise to a round bottom flask. After the dropwise addition, 52 g (754 mmol) of sodium nitrite was added dropwise to the mixture. The mixture was stirred at the same temperature for 1 hour. After the mixture was heated to room temperature, 3 g of ice and urea were added. When the mixture was cooled to 0 캜, potassium iodide was slowly added dropwise do. After the dropwise addition was completed, the mixture was stirred at room temperature, treated with sodium thiosulfate, extracted, concentrated, and subjected to column separation to obtain 8-iodo-2-naphthol. (105 g, yield 61.9%).

Synthesis Example 1-2-b) Synthesis of 8-iodonaphthalen-2-yl trifluoromethanesulfonate

Scheme 1-2-b)

19.6 g (73 mmol) of the 8-iodo-2-naphthol obtained in Synthesis Example 1-2-a was dissolved in dichloromethane, and 7 mL (87 mmol) of pyridine was added to the round bottom flask and cooled to 0 ° C.

After 14.7 mL (87 mmol) of anhydrous trifluoromethanesulfonic anhydride was slowly added dropwise, the reaction mixture was heated to room temperature and sufficiently stirred. After confirming by TLC, 2 M hydrochloric acid was added, and the mixture was extracted and concentrated. (22 g, yield 75.3%).

Synthesis Example 1-3 Synthesis of 8- (10- (naphthalen-2-yl) anthracen-9-yl) naphthalen-2-yl trifluoromethanesulfonate

Scheme 1-3)

22 g (55 mmol) of the 8-iodonaphthalen-2-yl trifluoromethanesulfonate prepared in Synthesis Example 1-2), 10- ( 1.27 g of tetrakis (triphenylphosphine) palladium (0), 15.2 g (109 mmol) of potassium carbonate in tetrahydrofuran (1 mmol) were added to a tetrahydrofuran 110 mL of toluene, 110 mL of toluene and 44 mL of water, and reflux. When the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate / water, and the organic layer was concentrated, followed by column separation to obtain the product. (21.5 g, yield 73%).

Synthesis Example 1-4) Synthesis of [Compound 1]

5.2 g (9 mmol) of the 8- (10- (naphthalen-2-yl) anthracen-9-yl) naphthalen-2-yl trifluoromethanesulfonate prepared in Synthesis Example 1-3) , 0.4 g of tetrakis (triphenylphosphine) palladium (0), 3.3 g of potassium carbonate, 25 mL of ethanol, 1 mL of toluene 25 mL, and water (10 mL), and reflux. When the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate / water, and the organic layer was concentrated and then subjected to column separation to synthesize [Compound 1]. (2.8 g, yield 61%).

MS (MALDI-TOF): m / z 498 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

129.6, 122.4, 125.4, 125.6, 126.3, 127.2, 128.3, 128.4, 129, 130.9, 131.6, 131.8,

[36C]

Synthesis Example 2. Synthesis of [Compound 2]

The same procedure as in Synthesis Example 1 was repeated except that 6-quinoxaline boronic acid was used instead of (1H-1,2,4-triazol-1-yl) boronic acid used in Synthesis Example 1-4) Compound 2] was synthesized. (3.4 g, 52% yield)

MS (MALDI-TOF): m / z 575 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

129.6, 125.1, 125.3, 125.4, 125.6, 126.3, 127.1, 127.2, 127.9, 128.3, 128.8, 129, 130.9, 131.8, 133.1,

[43C]

Synthesis Example 3. Synthesis of [Compound 3]

Amino-2-naphthol was used in place of 8-amino-2-naphthol used in Synthesis Example 1-2-a), and (1H-1,2,4-triazole -1-yl) boronic acid was used instead of 2-pyrimidinylboronic acid in the synthesis of [Compound 3]. (2.3 g, yield 42%).

MS (MALDI-TOF): m / z 509 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

123.7, 129.6,

[38C]

Synthesis Example 4. Synthesis of [Compound 4]

Except that (6-methylnaphthalen-2-yl) boronic acid was used in place of 2-naphthaleneboronic acid used in Synthesis Example 1-1-a) Synthesis of [Compound 4] was performed using the same method except that 8-quinolinol boronic acid was used in place of (1H-1,2,4-triazol-1-yl) boronic acid used in Example 1-4) Respectively. (3.0 g, 42% yield)

MS (MALDI-TOF): m / z 572 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

121.5, 119.6, 121.5, 125.1, 125.2, 125.4, 125.6, 126.2, 126.6, 127.2, 127.5, 127.6, 127.8, 128.1, 129, 130.2, 130.9, 131.1, 131.2, 131.3, 131.8, 132, 132.8, 133.1, 134.1, 134.7, 136.4, 138.1, 139.6, 146.5, 149.9

[44C]

Synthesis Example 5. Synthesis of [Compound 5]

Synthesis Example 5-1) Synthesis of 5- (10- (naphthalen-2-yl) anthracen-9-yl) naphthalen-1-yl trifluoromethanesulfonate

Amino-1-naphthol was used in place of 8-amino-2-naphthol used in Synthesis Example 1-2-a), the same procedure as in Synthesis Example 1-2) and Synthesis Example 1-3) To give a product. (7.4 g, 70% yield)

Synthesis Example 5-2) Synthesis of 2-methyl-2H-1,2,3-benzotriazole-5-boronic acid

Scheme 5-2)

5-Bromo-2-methyl-2H-1,2,3-benzotriazole (8.5 g, 40 mmol) was dissolved in 650 mL of THF in a round bottom flask. The n-BuLi (30 mL) was added slowly while cooling to -78 ° C. After the addition, trimethylborate (5.9 g, 56 mmol) was added thereto at -78 ° C for about 1 hour. After stirring at -78 ° C for 1 hour, the mixture was stirred at room temperature for 2 hours, and 2N HCl was added to adjust the acidity. The product was extracted with EA, and the solvent was removed to obtain crystals with hexane to obtain the product. (5.4 g, yield 78%).

Synthesis Example 5-3) Synthesis of [Compound 5]

Scheme 5-3)

5.2 g (9 mmol) of 5- (10- (naphthalen-2-yl) anthracen-9-yl) naphthalen-1-yl trifluoromethanesulfonate prepared in the above Synthesis Example 5-1) was added to a round bottom flask, 1.6 g (9 mmol) of 2-methyl-2H-1,2,3-benzotriazole-5-boronic acid prepared in the above Synthesis Example 5-2, tetrakis (triphenylphosphine) palladium g, 3.3 g of potassium carbonate, 25 mL of ethanol, 25 mL of toluene and 10 mL of water, and reflux. When the reaction was completed, the reaction solution was cooled to room temperature and extracted with ethyl acetate / water. The organic layer was concentrated and then subjected to column separation to synthesize [Compound 5]. (2.2 g, yield 60%).

MS (MALDI-TOF): m / z 562 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

123.9, 119.6, 125.1, 125.4, 125.6, 126.3, 127.2, 127.4, 127.9, 128.3, 129,

[41C]

Synthesis Example 6. Synthesis of [Compound 6]

Synthesis Example 6-1. Synthesis of 2,6-dialkyl substituted 10- (naphthalen-2-yl) anthracene-9-yl boronic acid

Synthesis Example 6-1-a) Synthesis of 2,6-dialkyl-substituted anthracene derivative

2-Methyl-2-hexanol (35 g, 300 mmol) and anthracene (18.4 g, 100 mmol) were added to 50 mL trifluoroacetic acid and refluxed under nitrogen for 24 h. Upon completion of the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The organic layer is concentrated under reduced pressure, and the resulting solid is filtered off and separated by column chromatography. The product was recrystallized from methanol. (6 g, yield 16%).

Synthesis Example 6-1-b) Synthesis of 2,6-dialkyl-substituted 9,10-dibromoanthracene

(6 g, 16 mmol) synthesized in Synthesis Example 6-1-a was added to 100 mL of dichloroethane and bromine (2.1 mL, 40 mmol) was added thereto while stirring at room temperature for 4 hours. Was added dropwise. This was poured into water and sodium sulfate was added to consume the residual bromine. This was then extracted with dichloromethane and the organic layer was dried over magnesium sulfate. The resulting material was passed through an alumina column using dichloromethane eluent, then evaporated, and methanol was added to precipitate a pale yellow solid to give about 7.2 g of product.

Synthesis Example 6-1-c) Synthesis of 2,6-dialkyl-substituted 9-bromo-10- (naphthalen-2-yl) anthracene

7.2 g (13 mmol) of 2,6-dialkyl-substituted 9,10-dibromoanthracene prepared in Synthesis Example 6-1-b), 2.4 g (13 mmol) of 2-naphthaleneboronic acid, Insert the 3.7 g (27 mmol), Pd (PPh 3) 4 0.3 g (3 mmol), 15 ml water, 40 ml of toluene and tetrahydrofuran and 40 ml of potassium carbonate was reacted under reflux.

After completion of the reaction, the reaction mixture was subjected to layer separation to remove the water layer, and the organic layer was concentrated under reduced pressure and recrystallized from toluene hexane to obtain the product (5.2 g, yield 68%).

Synthesis Example 6-1-d) Synthesis of 2,6-dialkyl-substituted 10- (naphthalen-2-yl) anthracene-9-yl boronic acid

The 2,6-dialkyl-substituted 9-bromo-10- (naphthalen-2-yl) anthracene prepared in Synthesis Example 6-1-c) Boronic acid (7.4 g, yield 77%) was synthesized using the same procedure except that bromo-10- (naphthalen-2-yl) anthracene was used.

Synthesis Example 6-2) Synthesis of 4-iodonaphthalen-1-yl trifluoromethanesulfonate

The product (20 g, yield 76%) was obtained using the same method except that 4-amino-1-naphthol was used in place of 8-amino-2-naphthol used in Synthesis Example 1-2).

Synthesis Example 6-3) Synthesis of 4- (2,6-bis (2-methylhexan-2-yl) -10- (naphthalen-2-yl) anthracene-9-yl) naphthalen- 1 -yltrifluoromethanesulfo Synthesis of Nate

Iodonaphthalen-1-yl trifluoromethanesulfonate prepared in Synthesis Example 6-2) instead of 8-iodonaphthalen-2-yl trifluoromethanesulfonate used in Synthesis Example 1-3) Diacrylate was used instead of 2,6-dialkyl-substituted 10- (naphthalene-2-yl) aniline prepared in Synthesis Example 6-1) instead of (10- ) Anthracene-9-ylboronic acid, the product (12 g, yield 71%) was obtained.

Synthesis Example 6-4) Synthesis of [Compound 6]

Was obtained in the same manner as in Synthesis Example 6-1) except that 8- (10- (naphthalen-2-yl) anthracene-9-yl) naphthalen-2-yl trifluoromethanesulfonate used in Synthesis Example 1-4) 9-yl) naphthalen-1-yl trifluoromethanesulfonate was used instead of 4- (2,6-bis (2-methylhexan-2-yl) -10- (naphthalen- The same procedure was followed except that (1,10-phenanthroline-5-yl) boronic acid was used instead of 1H-1,2,4-triazol-1-yl) (Yield: 42%).

MS (MALDI-TOF): m / z 838 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

129.1, 138.3, 123.5, 124.7, 125.4, 126.3, 127.2, 128.3, 128.4, 129.6, 130.3, 130.7, 131, 131.6, 131.8, 131.9, 132.9, 133.1, 133.9,134.2,135.7,136.4,137,147.3,149.9,154.6

[62C]

SYNTHESIS EXAMPLE 7 Synthesis of [Compound 7]

Synthesis Example 7-1) Synthesis of 2,3-dibromonaphthalen-1-amine

Scheme 7-1)

125 g (873 mmol) of 1-aminonaphthalene and 445 mL of acetic acid are added to a round bottom flask and the temperature of the reactor is cooled to 0 ° C. Bromine is diluted in 890 mL of acetic acid and added dropwise to the reactor. After completion, the temperature is raised to 60 占 폚 and stirred for 1 hour. When the reaction is complete, the temperature of the reactor is lowered to room temperature and the resulting salt is filtered. The filtered salt is added to an aqueous solution of sodium hydroxide and stirred. The resulting solid is filtered off and column separated. (145 g, 55%).

Synthesis Example 7-2) Synthesis of 5-bromonaphtho [1,2-d] [1,2,3] oxadiazole

Scheme 7-2)

60 g (200 mmol) of 2,3-dibromonaphthalene-1-amine prepared in Synthesis Example 7-1) and 900 mL of acetic acid were placed in a round-bottomed flask, and 150 mL of propionic acid And stir. Add 16 g of sodium nitrite and stir for 30 minutes. Pour the reaction solution into ice water. The resulting solid is filtered, and water is further added to the filtrate, followed by stirring and filtering. (24 g, 46%).

Synthesis Example 7-3) Synthesis of 4-bromo-2-naphthol

Scheme 7-3)

24 g (95 mmol) of 5-bromonaphtho [1,2-d] [1,2,3] oxadiazole prepared in Synthesis Example 7-2) was added to a round bottom flask under a nitrogen stream, Lt; / RTI &gt; 1.16 g of sodium borohydride is added to the reactor and stirred for 12 hours. An aqueous hydrochloric acid solution containing 28 mL of hydrochloric acid in 2334 mL of water is added dropwise to the reactor and stirred for 1 hour. When the reaction is completed, 10% aqueous sodium hydroxide solution is added to neutralize the reaction solution. Upon completion of the neutralization, the mixture is extracted with dichloromethane and water, and the organic layer is concentrated. The column is refined and recrystallized. (17 g, 78%)

Synthesis Example 7-4) Synthesis of 4-bromonaphthalen-2-yl trifluoromethanesulfonate

Scheme 7-4)

Bromo-2-naphthol (14.5 g, 65 mmol) synthesized in the above Synthesis Example 7-3) was dissolved in dichloromethane, and then 5.7 g (72 mmol) of pyridine was added thereto and the mixture was cooled do. 15.8 g (85 mmol) of trifluoromethanesulfonic anhydride is slowly added dropwise. After completion of the addition, the mixture is heated to room temperature and stirred sufficiently. After confirming by TLC, 2 M hydrochloric acid is added, and the mixture is extracted and concentrated. (20 g, 86.7%).

Synthesis Example 7-5) Synthesis of 5-bromo-1,2-diphenyl-1H-benzimidazole

4-Methylbenzenesulfonic acid (3.1 g, 16 mmol) was added to a solution of N ¹ -benzyl-4-bromobenzene-1,2-diamine (45 g, 160 mmol), 500 mL of dichloromethane and 30 mL of trimethyl orthobenzoate And the mixture is reacted under nitrogen at room temperature for about 40 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure, washed with 40% methanol / water and sodium hydrogencarbonate / water, and dried to obtain a product (22.3 g, yield 40%).

Synthesis Example 7-6 Synthesis of (1,2-diphenyl-1H-benzo [d] imidazol-5-yl)

Bromo-10- (naphthalen-2-yl) anthracene used in the above Synthesis Example 1-1-c) was used in place of the 9-bromo- -Benzimidazole (7 g, yield 35%). &Lt; RTI ID = 0.0 &gt;

Synthesis Example 7-7) Synthesis of 5- (4-bromonaphthalen-2-yl) -1,2-diphenyl-1H-benzo [d] imidazole

The same procedure as in Synthesis Example 7-1) was repeated except that 8- (10- (naphthalen-2-yl) anthracene-9-yl) naphthalen-2-yl trifluoromethanesulfonate used in Synthesis Example 1-4) -Bromonaphthalen-2-yl trifluoromethanesulfonate was used instead of (1H-1,2,4-triazol-1-yl) (7 g, yield 70%) was obtained using the same method except that 2-diphenyl-1H-benzo [d] imidazol-5-yl)

Synthesis Example 7-8) Synthesis of [Compound 7]

(4-bromonaphthalen-2-yl) -1 (4-bromophenyl) -1,2,3,4-tetrahydroisoquinolinecarboxylate prepared in the above Synthesis Example 7-7 instead of 8-iodonaphthalen- (2-diphenyl-1H-benzo [d] imidazole) was synthesized in the same manner as in [Compound 7] (3.2 g, yield 47%).

MS (MALDI-TOF): m / z 699 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

114.6, 115.7, 119.6, 122.1, 122.9, 125.4, 125.6, 126.3, 127.2, 127.5, 128.2, 128.3, 129, 129.2, 129.6, 130.9, 131, 131.1, 131.8, 132.33.1, 134.4, 134.2, 134.6, 134.7, 134.9, 137, 137.2, 138.2, 139.4, 143.2, 149.4

[53C]

Synthesis Example 8 Synthesis of [Compound 8]

Synthesis Example 8-1) Synthesis of 1,8-di (1,3,4-oxadiazol-2-yl) naphthalene

Scheme 8-1)

Dibromonaphthalene was used instead of 9-bromoanthracene used in Synthesis Example 1-1-a), and instead of phenylboronic acid (1,3,4-oxadiazol-2-yl) boron The product was obtained using the same method except that the acid was used (26 g, yield: 71%).

Synthesis Example 8-2) Synthesis of 2,2 '- (4-bromonaphthalene-1,8-diyl) bis (1,3,4-oxadiazole)

Scheme 8-2)

29 g (103 mmol) of 1,8-di (1,3,4-oxadiazol-2-yl) naphthalene prepared in Synthesis Example 8-1) was dissolved in 0.3 L of dichloromethane, Lt; 0 &gt; C. 18.2 g (114 mmol) of bromine was dropwise added dropwise to 0.1 L of dichloromethane. After stirring for 3 hours at room temperature, sodium bicarbonate solution was added to terminate the reaction, and the aqueous layer was removed. The organic layer was collected, concentrated, and then crystallized with methanol and slurried with acetone. (25 g, yield 75%).

Synthesis Example 8-3) Synthesis of [Compound 8]

2-yl trifluoromethanesulfonate used in Synthesis Example 1-3) was used instead of 2,2 '- (4-bromonaphthalene-1-yl) trifluoromethanesulfonate prepared in the above Synthesis Example 8-2 instead of 8-iodonaphthalen- 8-diyl) bis (1,3,4-oxadiazole) was used to synthesize [Compound 8]. (3.0 g, 40% yield)

MS (MALDI-TOF): m / z 567 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

129.6, 122.8, 124.7, 125.2, 125.4, 125.6, 126.3, 127.2,

[38C]

Synthesis Example 9. Synthesis of [Compound 9]

Synthesis Example 9-1) Synthesis of 7-chloro-2-phenyl-1-naphthol

Scheme 9-1)

To a round bottom flask was added phenylboronic acid 15.3 g (125 mmol), 2- bromo-7-chloro-1-naphthol 34.0 g (132 mmol), 36.6 g of potassium carbonate (264 mmol), Pd (PPh 3) 4 3 g (2 mmol), water (70 ml), toluene (180 ml) and tetrahydrofuran (180 ml).

After completion of the reaction, the reaction mixture was subjected to layer separation to remove the water layer, and the organic layer was concentrated under reduced pressure to obtain 26 g of a product (yield: 77%) by column chromatography.

Synthesis Example 9-2) Synthesis of 2-phenyl-7- (4-pyridinyl) -1-naphthol

Scheme 9-2)

To a round bottom flask was added 15.1 g (122 mmol) of 4-pyridinylboronic acid, 26.0 g (102 mmol) of 7-chloro-2-phenyl-1-naphthol prepared in Synthesis Example 9-1, 28.3 g _{204 mmol), Pd (PPh 3} ) 4 2.3 g (1.55 mmol), 54 ml of water, 140 ml of toluene and tetrahydrofuran and reacted under reflux into a 140 ml.

After completion of the reaction, layer separation was performed to remove the aqueous layer, and the organic layer was concentrated under reduced pressure to obtain 21.7 g (yield: 72%) of the product using column chromatography.

Synthesis Example 9-3) Synthesis of 2-phenyl-7- (4-pyridinyl) naphthalen-1-yl trifluoromethanesulfonate

Scheme 9-3)

Phenyl-7- (4-pyridinyl) -1-naphthol prepared in Synthesis Example 9-2) instead of 8-iodo-2-naphthol used in Synthesis Example 1-2-b) The product was obtained using the same method except for (21.3 g, yield 68%).

Synthesis Example 9-4) Synthesis of [Compound 9]

Phenyl-7- (4-pyridinyl) naphthalene-2-carboxylate prepared in Synthesis Example 9-3) instead of the 8-iodonaphthalen-2-yl trifluoromethanesulfonate used in Synthesis Example 1-3) [Compound 9] was synthesized by using the same method except that 1-yl trifluoromethane sulfonate was used (3.7 g, yield 53%).

MS (MALDI-TOF): m / z 584 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

128.6, 124.6, 126.4, 149.7

[45C]

Synthesis Example 10. Synthesis of [Compound 10]

Synthesis Example 10-1) Synthesis of (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid

Synthesis Example 10-1-a) Synthesis of 9- (naphthalen-1-yl) anthracene

To a round bottom flask was added 1-naphthalene boronic acid 19.4 g (158 mmol), 9- bromo-anthracene 34 g (132 mmol), potassium carbonate 36.6 g (264 mmol), Pd (PPh 3) 4 3 g (2 mmol), 70 ml of water, 180 ml of toluene and 180 ml of tetrahydrofuran were placed and subjected to a reflux reaction.

After completion of the reaction, the layers were separated to remove the aqueous layer, and the organic layer was concentrated under reduced pressure to obtain 32.7 g (yield: 80%) of 9- (naphthalene-1-yl) anthracene by column chromatography.

Synthesis Example 10-1-b) Synthesis of 9-bromo-10- (naphthalen-1-yl) anthracene

32.9 g (0.108 mol) of 9- (naphthalen-1-yl) anthracene prepared in Synthesis Example 10-1-a) and 550 ml of dichloromethane were placed in a round bottom flask and the crystals were dissolved at room temperature. After that, 20.2 g (0.126 mol) of bromine was diluted in 100 ml of dichloromethane and allowed to react slowly. After completion of the reaction, the water layer was removed to remove the water layer, and the organic layer was concentrated under reduced pressure, and crystals were precipitated from methanol and then recrystallized to obtain 30.6 g of yellow 9-bromo-10- (naphthalen-1-yl) ) Was obtained

Synthesis Example 10-1-c) Synthesis of (10- (naphthalen-1-yl) anthracene-9-yl) boronic acid

9-bromo-10- (naphthalen-1-yl) anthracene (30.6 g, 80 mmol) prepared in Synthesis Example 10-1-b) was dissolved in 220 mL of THF in a round bottom flask. N-Butyllithium (60 mL) was added slowly while cooling to -78 ° C. After the addition, trimethylborate (11.8 g, 112 mmol) was added at -78 ° C for about 1 hour. After stirring at -78 ° C for 1 hour, the mixture was stirred at room temperature for 2 hours, and 2N aqueous hydrochloric acid solution was added to adjust the acidity. EA followed by removal of the solvent, and crystals were obtained from hexane to obtain 21 g (yield: 76%) of 10- (naphthalen-1-yl) anthracene-9-yl) boronic acid.

Synthesis Example 10-2) Synthesis of 3-iodonaphthalen-2-yl trifluoromethanesulfonate

Synthesis Example 10-2-a) Synthesis of 3-iodo-2-naphthol

Scheme 10-2-a)

100 g (628 mmol) of 3-amino-2-naphthol are dissolved in 300 mL of acetic acid, cooled to 0 ° C, and 200 mL of sulfuric acid is slowly added dropwise to a round bottom flask. After the dropwise addition, 52 g (754 mmol) of sodium nitrite was added dropwise to the mixture. The mixture was stirred at the same temperature for 1 hour. After the mixture was heated to room temperature, 3 g of ice and urea were added. When the mixture was cooled to 0 캜, potassium iodide was slowly added dropwise do. After the dropwise addition was completed, the mixture was stirred at room temperature, treated with sodium thiosulfate, extracted, concentrated, and subjected to column separation to obtain 3-iodo-2-naphthol. (105 g, yield 61.9%).

Synthesis Example 10-2-b) Synthesis of 3-iodonaphthalen-2-yl trifluoromethanesulfonate

Scheme 10-2-b)

19.6 g (73 mmol) of the 3-iodo-2-naphthol obtained in Synthesis Example 10-2-a) was dissolved in dichloromethane, and 7 mL (87 mmol) of pyridine was added to the round bottom flask and cooled to 0 ° C .

After 14.7 mL (87 mmol) of anhydrous trifluoromethanesulfonic anhydride was slowly added dropwise, the reaction mixture was heated to room temperature and sufficiently stirred. After confirming by TLC, 2 M hydrochloric acid was added, and the mixture was extracted and concentrated. (22 g, yield 75.3%).

Synthesis Example 10-3 Synthesis of 3- (10- (naphthalen-1-yl) anthracen-9-yl) naphthalen-2-yl trifluoromethanesulfonate

Scheme 10-3)

22 g (55 mmol) of 3-iodonaphthalen-2-yl trifluoromethanesulfonate prepared in Synthesis Example 10-2), 10- ( (60 mmol) of tetrakis (triphenylphosphine) palladium (0) (1.27 g, 1 mmol), potassium carbonate (15.2 g, 109 mmol) and tetrahydrofuran 110 mL of toluene, 110 mL of toluene and 44 mL of water, and reflux. When the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate / water, and the organic layer was concentrated, followed by column separation to obtain the product. (27 g, 86% yield)

Synthesis Example 10-4) Synthesis of [Compound 10]

5.5 g (9 mmol) of 3- (10- (naphthalen-1-yl) anthracen-9-yl) naphthalen-2-yl trifluoromethanesulfonate prepared in Synthesis Example 10-3) was added to a round bottom flask, 1.1 g (9 mmol) of 2-pyrimidinylboronic acid, 0.4 g of tetrakis (triphenylphosphine) palladium (0), 3.3 g of potassium carbonate, 25 mL of ethanol, 25 mL of toluene and 10 mL of water are placed and refluxed. When the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate / water, and the organic layer was concentrated and then subjected to column separation to synthesize [Compound 10]. (1.8 g, 47% yield)

MS (MALDI-TOF): m / z 509 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

117.7,125.6,126.1,126.2,126.6,127.7,128.1,128.2,129,130.9,132,132.7,132.8,133.1,134.2,135.2,137.2,156.1,164.2

[38C]

Synthesis Example 11. Synthesis of [Compound 11]

[Compound 11] was synthesized in the same manner as in Synthesis Example 10 except that 3-pyridinylboronic acid was used instead of 2-pyrimidinylboronic acid used in Synthesis Example 10-4). (3.0 g, 48% yield)

MS (MALDI-TOF): m / z 508 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

126.1, 126.6, 126.6, 127.7, 128.1, 128.2, 129, 130.9, 132, 132.7, 133,

[39C]

Synthesis Example 12. Synthesis of [Compound 12]

Amino-2-naphthol was used in place of 3-amino-2-naphthol used in Synthesis Example 10-2-a), the same procedure as Synthesis Example 10-2) was used, [Compound 12] was synthesized in the same manner as in Synthesis Example 10 except that 6-quinoxaline boronic acid was used in place of 2-pyrimidinylboronic acid used in 4). (3.0 g, 53% yield)

MS (MALDI-TOF): m / z 559 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

126.3, 125.2, 126.3, 127.1, 127.7, 127.9, 128.1, 128.2, 128.3, 130.9,

[42C]

Synthesis Example 13. Synthesis of [Compound 13]

Amino-2-naphthol was used in place of 3-amino-2-naphthol used in Synthesis Example 10-2-a), the same procedure as Synthesis Example 10-2) was used, [Compound 13] was synthesized using the same method except that 8-quinolinoluboronic acid was used in place of 2-pyrimidinylboronic acid used in 4). (2.5 g, 40% yield)

MS (MALDI-TOF): m / z 558 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

128.5, 127.2, 127.2, 127.5, 127.7, 127.8, 128.1, 128.2, 130.9, 132, 132.7, 132.8, 133.1, 134.1, 134.2, 134.7, 136.3, 136.4, 136.7, 137.2, 138.1, 146.5,149.9

[43C]

Synthesis Example 14. Synthesis of [Compound 14]

The same procedure as in Synthesis Example 10-1) was repeated except for using (6-methylnaphthalen-1-yl) boronic acid instead of 1-naphthaleneboronic acid used in Synthesis Example 10-1-a) Amino-2-naphthol was used in place of 3-amino-2-naphthol used in Example 10-2-a), the same procedure as in Synthesis Example 10-2) was used, [Compound 14] was synthesized by the same method except that (1, 10-phenanthroline-5-yl) boronic acid was used in place of 2-pyrimidinylboronic acid used in Example 1. (3.4 g, 45% yield)

MS (MALDI-TOF): m / z 623 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

130.5,

[47C]

Synthesis Example 15. Synthesis of [Compound 15]

Synthesis Example 15-1) Synthesis of 5-bromo-1,2-diphenyl-1H-benzimidazole

4-Methylbenzenesulfonic acid (3.1 g, 16 mmol) was added to a solution of N ¹ -benzyl-4-bromobenzene-1,2-diamine (45 g, 160 mmol), 500 mL of dichloromethane and 30 mL of trimethyl orthobenzoate And the mixture is reacted under nitrogen at room temperature for about 40 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure, washed with 40% methanol / water and sodium hydrogencarbonate / water, and dried to obtain a product (22.3 g, yield 40%).

Synthesis Example 15-2 Synthesis of (1,2-diphenyl-1H-benzo [d] imidazol-5-yl)

Bromo-10- (naphthalen-2-yl) anthracene used in Synthesis Example 10-1-c) was used in place of 9-bromo- -Benzimidazole (6.8 g, yield 37%). &Lt; RTI ID = 0.0 &gt;

Synthesis Example 15-3 Synthesis of [Compound 15]

Amino-2-naphthol was used in place of 3-amino-2-naphthol used in Synthesis Example 10-2-a), the same procedure as Synthesis Example 10-2) was used, Except that 1,2-diphenyl-1H-benzo [d] imidazol-5-yl) boronic acid prepared in Synthesis Example 15-2) was used in place of 2-pyrimidinylboronic acid used in 4) [Compound 15] was synthesized using the same method as Synthesis Example 10. (2.4 g, 47% yield)

MS (MALDI-TOF): m / z 699 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

123.6

[53C]

Synthesis Example 16. Synthesis of [Compound 16]

Synthesis Example 16-1. Synthesis of 2,6-dialkyl-substituted 10- (naphthalen-1-yl) anthracene-9-ylboronic acid

Synthesis Example 16-1-a) Synthesis of 2,6-dialkyl-substituted anthracene derivative

2-Methyl-2-hexanol (35 g, 300 mmol) and anthracene (18.4 g, 100 mmol) were added to 50 mL trifluoroacetic acid and refluxed under nitrogen for 24 h. Upon completion of the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The organic layer is concentrated under reduced pressure, and the resulting solid is filtered off and separated by column chromatography. The product was recrystallized from methanol. (6 g, yield 16%).

Synthesis Example 16-1-b) Synthesis of 2,6-dialkyl-substituted 9,10-dibromoanthracene

The 2,6-dialkyl-substituted anthracene (6 g, 16 mmol) synthesized in the above Synthesis Example 16-1-a was placed in 100 mL of dichloroethane and bromine (2.1 mL, 40 mmol) was added thereto with stirring at room temperature for 4 hours ) Was added dropwise. This was poured into water and sodium sulfate was added to consume the residual bromine. This was then extracted with dichloromethane and the organic layer was dried over magnesium sulfate. The resulting material was passed through an alumina column using dichloromethane eluent, then evaporated, and methanol was added to precipitate a pale yellow solid to give about 7.2 g of product.

Synthesis Example 16-1-c) Synthesis of 2,6-dialkyl-substituted 9-bromo-10- (naphthalen-1-yl) anthracene

7.2 g (13 mmol) of 2,6-dialkyl-substituted 9,10-dibromoanthracene prepared in Synthesis Example 16-1-b), 2.2 g (13 mmol) of 1-naphthaleneboronic acid, Insert the 3.7 g (27 mmol), Pd (PPh 3) 4 0.3 g (3 mmol), 15 ml water, 40 ml of toluene and tetrahydrofuran and 40 ml of potassium carbonate was reacted under reflux.

After completion of the reaction, the layers were separated to remove the aqueous layer, and the organic layer was concentrated under reduced pressure, and recrystallized with toluene hexane to obtain a product. (4.9 g, yield 65%).

Synthesis Example 16-1-d) Synthesis of 2,6-dialkyl-substituted 10- (naphthalen-1-yl) anthracene-9-ylboronic acid

Dialkyl-substituted 9-bromo-10- (naphthalen-1-yl) anthracene prepared in Synthesis Example 16-1-c) instead of 9-bromo- (4 g, yield: 63%) was synthesized by using the same method except that bromo-10- (naphthalen-1-yl) anthracene was used.

Synthesis Example 16-2) Synthesis of 2-methyl-2H-1,2,3-benzotriazole-5-boronic acid

Scheme 16-2)

5-Bromo-2-methyl-2H-1,2,3-benzotriazole (8.5 g, 40 mmol) was dissolved in 650 mL of THF in a round bottom flask. The n-BuLi (30 mL) was added slowly while cooling to -78 ° C. After the addition, trimethylborate (5.9 g, 56 mmol) was added thereto at -78 ° C for about 1 hour. After stirring at -78 ° C for 1 hour, the mixture was stirred at room temperature for 2 hours, and 2N HCl was added to adjust the acidity. The product was extracted with EA, and the solvent was removed to obtain crystals with hexane to obtain the product. (5.5 g, yield 78%).

Synthesis Example 16-3) Synthesis of [Compound 16]

Amino-2-naphthol was used in place of 3-amino-2-naphthol used in Synthesis Example 10-2-a), the same procedure as Synthesis Example 10-2) was used, (2,6-bis (2-methylhexan-2-yl) -) - boronic acid prepared in the above Synthesis Example 16-1) instead of (10- (naphthalen- Boronic acid used in Synthesis Example 10-4) instead of 2-pyrimidinylboronic acid used in Synthesis Example 10-4), except that 2-methyl (2-methylpiperazin-1-yl) -2H-1,2,3-benzotriazole-5-boronic acid was used in place of the compound [16]. (3.0 g, 45% yield)

MS (MALDI-TOF): m / z 758 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

126.1, 132.3, 124.7, 125.1, 125.4, 126.1, 126.2, 127.2, 127.4, 127.7, 127.9, 128.1, 128.2, 128.8, 130.1, 131, 131.6, 132.7, 133.1, 133.6,134.1,134.2,136.5,136.6,136.7,138.1,144.3,145.5,147.3

[55C]

Synthesis Example 17. Synthesis of [Compound 17]

Amino-1-naphthol was used in place of 3-amino-2-naphthol used in Synthesis Example 10-2-a), the same procedure as Synthesis Example 10-2) was used, [Compound 17] was synthesized except that (1H-1,2,4-triazol-1-yl) boronic acid was used in place of 2-pyrimidinylboronic acid used in 4). (2.5 g, 40% yield)

MS (MALDI-TOF): m / z 498 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

128.4,

[36C]

Synthesis Example 18. Synthesis of [Compound 18]

The same procedure as in Synthesis Example 10-2) was used, except that 6-amino-1,2-naphthalenediol was used in place of 3-amino-2-naphthol in Synthesis Example 10-2-a) Example 10-4 was repeated except that (1,3,4-oxadiazol-2-yl) boronic acid was used in place of 2-pyrimidinylboronic acid in the synthesis of [Compound 18 ] Was synthesized. (2.8 g, 48% yield)

MS (MALDI-TOF): m / z 567 [M] ^&lt; ⁺ & gt ^; . _{^{13 C NMR (75MHz, CDCl 3}} ) δ:

125.1, 125.2, 125.6, 126.1, 126.2, 127.7, 128.1, 128.2, 128.8, 130.9, 132.1, 132.4, 132.7, 132.8, 133.1,

[38C]

Examples 1 to 18

Manufacture of organic light-emitting diodes

The ITO glass was patterned to have a light emitting area of 2 mm 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the base pressure was adjusted to 1 10 ^-7 torr. Then, an organic material was deposited on the ITO using DNTPD (700 ANGSTROM), NPD (300 ANGSTROM) (10 Å) and Al (1,000 Å) were selectively formed in the order of [Compound 5] (5 wt%) (250 Å) ), And measurements were made at 0.4 mA.

The structures of [Formula 4] and [Formula 5] and [Compounds 1] to [Compound 18] are as follows.

[Chemical Formula 4]

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

Example 19

Except that Liq (Lithium 8-hydroxy quinolate) corresponding to the compound [5] prepared by the present invention and the electron transport layer material conventionally used in the electron transport layer in the weight ratio of 50: 50 were mixed and used.

[Liq]

Example 20

Was prepared in the same manner as in Example 5, except that the following Formula 6 was used in place of Formula 5 used in the light emitting layer.

[Chemical Formula 6]

Example 21

Was prepared in the same manner as in Example 5 except that the following Formula 7 was used instead of Formula 5 used in the light emitting layer.

(7)

Comparative Example

The organic light emitting diode device for the comparative example was fabricated in the same manner except that Alq ₃ was used instead of the anthracene compound produced by the present invention in the electron transporting layer in the device structures of Examples 1 to 21 above.

[Alq ₃ ]

As shown in Table 1, the organic light emitting device including the anthracene derivative compound according to the present invention in the electron transport layer has improved electron transport ability compared with the organic light emitting device employing Alq _3, which is widely used as an electron transport layer material, Can be driven, and is excellent in light emission efficiency and can be utilized in an organic light emitting device.

Claims (14)

An anthracene derivative represented by the following formula (A) or (B).
[Chemical Formula A]

In the above formulas (A) and (B)
Y is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted group having 1 to 50 carbon atoms A substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms,
Z is the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms Lt; / RTI &gt;group;
m and m 'are integers of 1 to 8;
Each of X ₁ to X ₁₄ is the same or different and is independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 aryl A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroatom having O, N or S A heteroaryl group of a small number of 2 to 50, a cyano group, a nitro group, and any one selected from the group consisting of halogen group, may form a fused ring group of aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other;
In the above formula (A), X ₁ To X ₇ And at least one of X ₈ To X &lt; ₁₄ &gt; is a heteroaryl group having 2 to 20 carbon atoms each containing a nitrogen atom;
The 'substituted' in the above 'substituted or unsubstituted' means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , An alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 1 to 24 carbon atoms. The method according to claim 1,
When at least one of X ₁ to X ₇ in the above formula (A) and at least one of X ₈ to X ₁₄ in the formula (B) is a heteroaryl group having 2 to 20 carbon atoms each containing a nitrogen atom, said heteroaryl group is An anthracene derivative characterized by being any one substituent selected from Structural Formulas 1 to 6.
[Structural formula 1]

[Structural formula 2]

[Structural Formula 3]

[Structural Formula 4]

[Structural Formula 5]

[Structural Formula 6]

In Structural Formulas 1 to 6
T ₁ to T ₈ are the same or different and independently selected from the group consisting of C (R ₁₁ ), C (R ₁₁ ) (R ₁₂ ), N, N (R ₁₃ ), O and S;
Wherein R ₁ to R ₁₃ are the same or different from each other and independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a heteroaryl group having 2 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S,
In each of Structural Formulas ₁ to 6, one of R ₁ to R ₁₃ is a single bond forming a bond with the naphthyl group in Formulas A and B above. 3. The method of claim 2,
In the above formulas (A) and (B), Y and Z are the same or different, and independently of each other, hydrogen, deuterium; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 5 to 20 carbon atoms; , And m is an integer of 1 to 4. The anthracene derivative The method of claim 3,
In the above formula (A), the substituent X ₁ To X ₇ Is any one substituent selected from the structural formulas 1 to 6, and the substituent X ₈ To X &lt; ₁₄ &gt; are any one substituent selected from the structural formulas 1 to 6. [ 5. The method of claim 4,
Wherein each of the substituents in the above Structural Formulas 1 to 6 is substituted with 1 to 3 nitrogen atoms to an aromatic carbon position in the substituent to form a heteroaryl group. The method according to claim 1,
The X ₁ of formula [A] To X ₇ And at least one of substituent X ₈ of formula (B) To X &lt; ₁₄ &gt; are each any one of substituent groups 101 to 606 shown below.
[Substituent 101] [Substituent 102] [Substituent 103]

[Substituent group 104] [Substituent group 105] [Substituent group 106]

[Substituent group 107] [Substituent group 108] [Substituent group 109]

[Substituent group 110] [Substituent group 111] [Substituent group 112] [Substituent group 113]

[Substituent group 201] [Substituent group 202] [Substituent group 203]

[Substituent group 204] [Substituent group 205] [Substituent group 206]

[Substituent 207] [Substituent 208]

[Substituent group 301] [Substituent group 302] [Substituent group 303]

[Substituent group 304] [Substituent group 305] [Substituent group 306]

[Substituent group 307] [Substituent group 308]

[Substituent 401] [Substituent 402] [Substituent 403]

[Substituent group 404] [Substituent group 405] [Substituent group 406]

[Substituent group 407] [Substituent group 408] [Substituent group 409]

[Substituent group 410] [Substituent group 411] [Substituent group 412] [Substituent group 413]

[Substituent group 501] [Substituent group 502] [Substituent group 503]

[Substituent 601] [Substituent 602] [Substituent 603]

[Substituent 604] [Substituent 605] [Substituent 606]

Wherein R is the same or different and is independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, Or an unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted (having 6 to 60 carbon atoms) amino group, a di (substituted or unsubstituted) alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and each of May be fused to adjacent groups to form a ring,
n is an integer of 0 to 9,
When the substituent R is not bonded to the carbon of the aromatic ring in the heteroaryl group of the substituents 101 to 606, hydrogen is bonded,
One of the Rs is a single bond bonded to the naphthyl group of the formula (A). The method according to claim 6,
Only one of X ₁ to X ₇ in the above formula [A] is any one substituent selected from the above-mentioned substituents 101 to 606, and only one of the substituents X ₈ to X ₁₄ in the above-mentioned formula [B] And an anthracene derivative. A first electrode;
A second electrode facing the first electrode; And
And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one anthracene derivative selected from the group consisting of the compounds represented by any one of claims 1 to 7. 9. The method of claim 8,
Wherein the organic layer comprises at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer. 9. The method of claim 8,
Wherein the organic layer interposed between the first electrode and the second electrode comprises an electron transporting layer and a light emitting layer. 11. The method of claim 10,
The anthracene derivative is included in the electron transporting layer,
Wherein the light emitting layer comprises a host and a dopant. 12. The method of claim 11,
Wherein the electron transporting layer is a mixture of an anthracene derivative and an electron transporting compound different from the anthracene derivative. 13. The method of claim 12,
Wherein the electron transporting layer has a mixing ratio of the anthracene derivative and an electron transporting compound different from that of the anthracene derivative in the range of 10:90 to 90:10 by weight. 14. The method of claim 13,
Wherein the other electron-transporting compound is a compound represented by the following formula (C)
&Lt; RTI ID = 0.0 &

In the above formula (C)
Wherein M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom, and OA is a monovalent ligand capable of single bond or coordination bond with M,
O is oxygen,
A represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2 to C20 Substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, and substituted or unsubstituted hetero atoms having 2 to 50 carbon atoms having O, N or S, An aryl group,
M is 1 and n is 0 when M is a metal selected from an alkali metal,
M = 1, n = 1, or m = 2 and n = 0 when M is a metal selected from alkaline earth metals,
M is from 1 to 3 when M is boron or aluminum, and n is any of from 0 to 2, and m + n = 3;
M is from 1 to 3 when M is boron or aluminum, and n is any of from 0 to 2, and m + n = 3;
Y are each the same or different and independently selected from the following formulas [C1] to [C39].
[Structural formula C1] [Structural formula C2] [Structural formula C3]

[Structural formula C4] [Structural formula C5] [Structural formula C6]

[Structural formula C7] [Structural formula C8] [Structural formula C9] [Structural formula C10]

[Structural formula C11] [Structural formula C12] [Structural formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structural formula C17] [Structural formula C18] [Structural formula C19] [Structural formula C20]

[Structural formula C21] [Structural formula C22] [Structural formula C23]

[Structural formula C24] [Structural formula C25] [Structural formula C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structural formula C31] [Structural formula C32] [Structural formula C33]

[Structural formula C34] [Structural formula C35] [Structural formula C36]

[Structural formula C37] [Structural formula C38] [Structural formula C39]

In the above Structural Formula C1 to Structural Formula C39,
R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And adjacent substituents may be connected to alkylene or alkenylene to form a spiro ring or a fused ring.
Herein, the 'substitution' in the 'substituted or unsubstituted' refers to a substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, An aryl group, a heteroaryl group, germanium, phosphorus, and boron. The term &quot; substituted aryl group &quot;

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