KR20160117492A - Triazine compound and method for producing same - Google Patents

Abstract

(일반식 (1) 중, 2개의 Ar⁴는 동일하고, 수소 원자 등을 나타낸다. Ar¹ 및 Ar²는, 각각 독립적으로, 탄소수 6 내지 18의 단환, 연결 또는 축환 방향족 탄화수소기 등을 나타낸다. Ar³은, 탄소수 6 내지 18의 단환, 연결 또는 축환 방향족 탄화수소기 등을 나타낸다. Z¹ 및 Z² 중 어느 한쪽이 질소 원자를 나타내고, 또 한쪽은 C-H를 나타낸다.)An object of the present invention is to provide an electron transporting material which is excellent in heat resistance and has a long life or an excellent luminous efficiency of an organic electroluminescent device. A triazine compound represented by the following general formula (1), and an organic electroluminescent device comprising the same.

(In the general formula (1), two Ar ^{4 s} are the same and represent a hydrogen atom, etc. Ar ¹ and Ar ² each independently represent a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms. Ar ³ represents a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms, either of Z ¹ and Z ² represents a nitrogen atom, and the other represents CH.

Description

[0001] TRIAZINE COMPOUND AND METHOD FOR PRODUCING SAME [0002]

TECHNICAL FIELD The present invention relates to a triazine compound, a production method thereof, and an organic electroluminescent device containing the same. More particularly, the present invention relates to a triazine compound useful as a material for an organic electroluminescence device, which is characterized by a structure in which a triaryl skeleton is combined with a diarylpyridyl group, and a process for producing the triazine compound. And an organic electroluminescent device having a high efficiency, a low voltage and a high durability.

The organic electroluminescent device has a basic constitution in which a light emitting layer containing a light emitting material is disposed between a hole transporting layer and an electron transporting layer and an anode and a cathode are provided on the outer side thereof. By the recombination of holes and electrons injected into the light emitting layer (Fluorescence or phosphorescence) when excitons generated by excitons are inactivated, and they are used in applications such as large-sized televisions and lighting as well as small-sized displays. The hole transporting layer may be divided into a hole transporting layer and a hole injecting layer, the light emitting layer may be divided into an electron blocking layer, a light emitting layer and a hole blocking layer, and the electron transporting layer may be divided into an electron transporting layer and an electron injecting layer. As the carrier transporting layer (electron transporting layer or hole transporting layer) of the organic electroluminescent device, a co-evaporated film doped with a metal, an organic metal compound or other organic compound may be used.

The conventional organic electroluminescent device has a driving voltage higher than that of the inorganic light emitting diode, low emission luminance and low luminous efficiency, and remarkably low device lifetime. Although recent organic electroluminescent devices have been gradually improved, a more excellent material is demanded in terms of light emitting efficiency, driving voltage characteristics, and longevity. In addition, high heat resistance may be required depending on the application, such as in-vehicle use, and a high glass transition temperature (Tg) of the material is required.

As the electron transporting material excellent in long life reputation for the organic electroluminescent device, the triazine compound disclosed in Patent Document 1 or 2 can be exemplified. However, further improvement has been required in view of the Tg of the material and the voltage, lifetime, and luminous efficiency of the organic electroluminescent device using the material.

JP 2011-063584 A JP 2008-280330 A

An object of the present invention is to provide an electron transporting material excellent in heat resistance and excellent in longevity, low voltage driving property, or light emitting efficiency of an organic electroluminescent device.

DISCLOSURE OF THE INVENTION The present inventors have intensively studied to solve the above problems, and as a result, they have found that a triazine compound having a diarylpyridyl group bonded thereto (hereinafter, also referred to as "triazine compound (1) The present inventors have found that the organic electroluminescent device used as a transport material has a lower voltage, a longer life, or a higher luminous efficiency compared to the case of using a conventionally known material, thereby completing the present invention.

That is, the present invention exists in the following [1] to [21].

[1] A triazine compound represented by the following general formula (1).

[2] The triazine compound according to [1], which is represented by the following general formula (1) 'or (1)'.

[3] The triazine compound according to [1] or [2], wherein Ar ⁴ is a phenyl group, a methyl group or a hydrogen atom.

[4] The triazine compound according to any one of [1] to [3], wherein Ar ⁴ is a hydrogen atom.

[5] The compound according to [1], wherein each of Ar ¹ and Ar ² is independently a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms (the group is selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, Or a pyridyl group.) The triazine compound according to any one of [1] to [4].

[6] The compound according to any one of [1] to [5], wherein Ar ¹ and Ar ² are each independently a phenyl group, a naphthyl group or a phenanthryl group (these groups may be substituted with a fluorine atom, a methyl group, a phenyl group or a pyridyl group) A triazine compound according to any one of claims 1 to 3.

[7] The triazine compound according to any one of [1] to [6], wherein Ar ¹ and Ar ² are each independently a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group.

[8] The triazine compound according to any one of [1] to [7], wherein Ar ¹ and Ar ² are phenyl groups.

[9] A compound according to any one of [1] to [7], wherein Ar ³ is a monocyclic or a condensed nitrogen-containing compound having 3 to 13 carbon atoms consisting of a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms (the group may be substituted with a phenyl group or a pyridyl group) The triazine compound according to any one of [1] to [8], which is an aromatic hydrocarbon group (the group may be substituted with a phenyl group, a biphenyl group or a naphthyl group).

[10] A compound according to any one of [1] to [10], wherein Ar ³ is a phenyl group, a naphthyl group or a biphenyl group (these groups may be substituted with a phenyl group or a pyridyl group) or a monocyclic or a cyclic nitrogen- Or a naphthyl group), which is a triazine compound according to any one of [1] to [9].

[11] A compound according to any one of [1] to [11], wherein Ar ³ is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridylphenyl group, a pyridyl group, a pyrazyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, The triazine compound according to any one of [1] to [10], which is a compound represented by any one of [1] to [10], which is a phenylpyridyl group, a phenylpyridyl group, a biphenylpyrazyl group, a phenylpyrimidyl group, a biphenylpyrimidyl group, a phenylquinolyl group, a biphenylquinolyl group or a phenylisoquinolyl group compound.

[12] The compound according to any one of [1] to [11], wherein Ar ³ is a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a phenylpyridyl group, a pyrazyl group, a pyrimidyl group, a quinolyl group or an isoquinolyl group Azine compound.

[13] A process for producing a compound represented by the general formula (2) described below, a compound represented by the general formula (3) and a compound represented by the general formula (4) described below in the presence of a base or in the absence of a base, The method for producing a triazine compound according to any one of [1] to [12], wherein the triazine compound is subjected to a coupling reaction either sequentially or simultaneously in the presence of a base.

[14] The compound represented by the general formula (5) described later and the compound represented by the general formula (6) described below are subjected to a coupling reaction in the presence of a base or in the absence of a base in the presence of a palladium catalyst A method for producing a triazine compound according to any one of [1] to [12], which comprises the steps of:

[15] The compound represented by the general formula (7) described below and the compound represented by the general formula (8) described below are subjected to a coupling reaction in the presence of a base or in the absence of a base in the presence of a palladium catalyst A method for producing a triazine compound according to any one of [1] to [12], which comprises the steps of:

[16] The production method described in [13], [14] or [15], wherein the palladium catalyst is a palladium catalyst having a tertiary phosphine as a ligand.

[17] The process according to [13], wherein the palladium catalyst is palladium catalyst having triphenylphosphine or 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl as a ligand. 14], [15] or [16].

[18] A compound represented by the following general formula (9).

[19] The compound according to [14], which is represented by the following general formula (5).

[20] An organic electroluminescent device characterized by containing a triazine compound according to any one of [1] to [12].

[21] The organic electroluminescent device according to [20], wherein the electron transport layer contains a triazine compound.

According to the present invention, it is possible to provide an organic electroluminescent device which can provide a triazine compound having excellent heat resistance and is excellent in low voltage, long life or luminous efficiency.

Hereinafter, the present invention will be described in detail.

The triazine compound of the present invention is represented by the following general formula (1) (hereinafter also referred to as triazine compound (1)):

(In the general formula (1)

The two Ar ⁴ are the same and represent a hydrogen atom, a fluorine atom, a methyl group, a methoxy group or a phenyl group.

Ar ¹ and Ar ² each independently represent a monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms which is composed of a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms or a 6-membered ring, , A fluorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, or a pyridyl group).

Ar ³ represents a monocyclic, fused or cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms (the group may be substituted by a fluorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, or a pyridyl group) A monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms (the group is selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a pyridyl group, a phenyl group, a naphthyl group, Or may be substituted with a halogen atom).

Provided that ^{one of} Z ¹ and Z ² represents a nitrogen atom and the other represents CH.

The present invention also relates to a triazine compound (1), a production method thereof, an organic electroluminescent device containing it, and a production intermediate useful for producing a triazine compound represented by the general formula (1) 5) or (9)).

The substituents in the triazine compound (1) of the present invention are each defined as follows.

In the general formula (1), two Ar ⁴ represent the same substituent.

Ar ⁴ represents a hydrogen atom, a fluorine atom, a methyl group, a methoxy group or a phenyl group. Of these, a hydrogen atom, a methyl group or a phenyl group is preferable from the viewpoint of excellent electron transporting material characteristics, and a hydrogen atom is more preferable because of easy synthesis.

Ar ¹ and Ar ² each independently represent a monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms which is composed of a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms or a 6-membered ring (these groups are fluorine, An alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, or a pyridyl group).

Ar ¹ and Ar ² may be the same or different.

The monocyclic, bicyclic or tricyclic aromatic hydrocarbon group having 6 to 18 carbon atoms in Ar ¹ and Ar ² is not particularly limited and examples thereof include a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, A phenanthrenyl group, a phenrenyl group, a chrysenyl group, a fluoranthenyl group, an acenaphthylenyl group, a fluorenyl group or a benzofluorenyl group.

The monocyclic or cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms and composed of only a 6-membered ring in Ar ¹ and Ar ² is not particularly limited, but may be a pyridyl group, a pyrazyl group, a pyrimidyl group, a pyridazyl group, a tri Preferred examples thereof include an alkoxy group, an alkoxy group, an alkoxy group, an alkoxy group, an alkoxy group, an alkoxy group, an alkoxy group, an alkoxy group,

The alkyl group having 1 to 4 carbon atoms in Ar ¹ and Ar ² is not particularly limited and preferable examples thereof include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group and t-butyl group have.

The alkoxy group having 1 to 4 carbon atoms in Ar ¹ and Ar ² is not particularly limited, but methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group or t- And the like can be mentioned as preferable examples.

The monocyclic, bicyclic or cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms and substituted with a fluorine atom in Ar ¹ and Ar ² is not particularly limited, and examples thereof include a fluorophenyl group, a pentafluorophenyl group, a difluorobiphenyl group, A fluorophenanthryl group, a difluorophenanthryl group, a fluoroanthryl group, a difluoroanthryl group, a fluoropyranyl group, a difluoropyranyl group, a fluorotrienyl group, a fluoropyranyl group, A trifluoromethanesulfonyl group, a fluorenylsulfonyl group, a fluorenylsulfonyl group, a fluorenyl group, a fluorenyl group, a fluorenyl group, a fluorenyl group, a fluorenyl group, a trifluoromethanesulfonyl group, a phenylenelyl group, a difluorotriphenylenyl group, a fluorochrysinyl group, a difluorochrysenyl group, An acenaphthyl group and the like can be mentioned as preferable examples.

The monocyclic, linking or cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms and substituted with an alkyl group having 1 to 4 carbon atoms in Ar ¹ and Ar ² is not particularly limited and examples thereof include a methylphenyl group, a methylbiphenyl group, a methylnaphthyl group, A methylpentanyl group, a methylphenanthryl group, a methyl anthryl group, a methylpyranyl group, a methyltriphenylenyl group, a methylcyclenyl group, a methylfluorenenyl group, a methylenacenaphthylenyl group, a dimethylphenyl group, a dimethylbiphenyl group, a dimethylnaphthyl group , A dimethylphenanthryl group, a dimethyl anthryl group, a dimethylpyranyl group, a dimethyltriphenylenyl group, a dimethylcyclenyl group, a dimethylfluorenanthienyl group, a dimethylacenaphthylenyl group, a dimethylfluorenyl group Or a dimethylbenzofluorenyl group and the like can be mentioned as preferable examples.

The monocyclic, bicyclic or tricyclic aromatic hydrocarbon group having 6 to 18 carbon atoms substituted with an alkoxy group having 1 to 4 carbon atoms in Ar ¹ and Ar ² is not particularly limited, but methoxyphenyl group, methoxybiphenyl group, methoxy A naphthyl group, a methoxyphenanthryl group, a methoxyanthryl group, a methoxypyrenyl group, a methoxy triphenylenyl group, a methoxycyclenyl group, a methoxyfluoranthienyl group, a methoxyacenaphthylenyl group, a dimethoxyphenyl group , A dimethoxybiphenyl group, a dimethoxynaphthyl group, a dimethoxyphenanthryl group, a dimethoxyanthryl group, a dimethoxypyranyl group, a dimethoxy triphenylrenyl group, a dimethoxycychenecyl group, a dimethoxy A dimethoxyacenaphthylenyl group, a dimethoxyfluorenyl group or a dimethoxybenzofluorenyl group, and the like can be mentioned as preferable examples.

The monocyclic, bicyclic or cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms substituted with a phenyl group in Ar ¹ and Ar ² is not particularly limited, but a phenylnaphthyl group, a phenylphenanthryl group, an anthryl group, a phenylpyranyl group , Phenyltriphenylenyl group, phenylcyclenyl group, phenylfluorenanthienyl group, phenylacenaphthylenyl group, diphenylphenyl group, diphenylbiphenyl group, diphenylnaphthyl group, diphenylphenanthryl group, anthryl group, diphenyl Preferred examples thereof include a pyrenyl group, a diphenyltriphenylenyl group, a diphenylcyclenyl group, a diphenylfluoranthanyl group, a diphenylacenaphthylenyl group, a diphenylfluorenyl group or a diphenylbenzofluorenyl group and the like .

The monocyclic, bicyclic or tricyclic aromatic hydrocarbon group having 6 to 18 carbon atoms substituted with a pyridyl group in Ar ¹ and Ar ² is not particularly limited, and examples thereof include a pyridylphenyl group, a pyridylbiphenyl group, a pyridylnaphthyl group, A pyridylphenyl group, a pyridylphenanthryl group, an anthryl group, an pyridylpyranyl group, a pyridyl triphenylenyl group, a pyridylcyclenyl group, a pyridyl fluoranthienyl group, a pyridylacenaphthylenyl group, A thiadiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridyl group, a pyridyl group, a pyridyl group, a pyridyl group, a pyridyl group, a pyrimidyl group, A pyridyl acenaphthyl group, a dipyridyl fluorenyl group or a dipyridyl benzofluorenyl group, and the like.

The monocyclic or cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms and substituted with a fluorine atom in Ar ¹ and Ar ² is not particularly limited, and examples thereof include a fluoropyridyl group, a fluoropyridyl group, a fluoropyrimidyl group, Preferable examples include fluoropyridyl group, fluorotriacyl group, fluoroquinolyl group, fluoro isoquinolyl group, fluorophenanthridyl group, fluorobenzoquinolyl group and fluoroacridyl group .

The monocyclic or cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms and substituted with an alkyl group having 1 to 4 carbon atoms in Ar ¹ and Ar ² is not particularly limited and examples thereof include a methylpyridyl group, Methylpyrrolidyl group, methylpyridazyl group, methyltriazyl group, methylquinolyl group, methylisoquinolyl group, methylphenanthryl group, methylbenzoquinolyl group or methylacryidyl group.

The monocyclic or cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms which is substituted with an alkoxy group having 1 to 4 carbon atoms in Ar ¹ and Ar ² 2 is not particularly limited and examples thereof include a methoxypyridyl group, A methoxypyridazinyl group, a methoxypyridazyl group, a methoxy triacyl group, a methoxyquinolyl group, a methoxy isoquinolyl group, a methoxyphenanthryl group, a methoxybenzoquinolyl group or a methoxyacridyl group are preferably used For example.

The monocyclic or cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms substituted with a phenyl group in Ar ¹ and Ar ² 2 is not particularly limited, but a phenylpyridyl group, a phenylpyrazyl group, a phenylpyrimidyl group, Preferable examples include a polyvalent group, a phenyltriazyl group, a phenylquinolyl group, a phenylisoquinolyl group, a phenylphenanthryl group, a phenylbenzoquinolyl group or a phenylacryl group.

The monocyclic or cyclic nitrogen-containing aromatic hydrocarbon group of 3 to 13 carbon atoms substituted with a pyridyl group in Ar ¹ and Ar ² is not particularly limited, but a bipyridyl group, a pyridylpyrazyl group, a pyridylpyrimidyl group, Preferable examples thereof include pyridylpyridazyl, pyridyltriazyl, pyridylquinolyl, pyridyl isoquinolyl, pyridylphenanthryl, pyridylbenzoquinolyl and pyridylcaridyl groups.

Each of Ar ¹ and Ar ² is independently a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms (this group is a fluorine atom, an alkyl group having 1 to 4 carbon atoms, A phenyl group or a pyridyl group), and each independently represents a phenyl group, a naphthyl group or a phenanthryl group (these groups may be substituted with a fluorine atom, a methyl group, a phenyl group or a pyridyl group) ), More preferably independently of each other, a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group.

Specific examples of Ar ¹ and Ar ² include, but are not limited to, phenyl, p-tolyl, m-tolyl, o-tolyl, 2,4- Ethylphenyl, 4-ethylphenyl, 2,4-diethylphenyl, 3,5-diethylphenyl, 2-propylphenyl, 3-propylphenyl, 4-propylphenyl, 2,4 Isopropylphenyl group, 2,4-diisopropylphenyl group, 3,5-diisopropylphenyl group, 2-isopropylphenyl group, 2-isopropylphenyl group, Butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2-tert-butylphenyl group, 3- Butylphenyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 3-methylbiphenyl- 4-yl group, 2'-methylbiphenyl-4-yl group, 4'- Yl group, 5-methylbiphenyl-4-yl group, 2, 4'- Methyl biphenyl-3-yl group, 6'-dimethylbiphenyl-3-yl group, 2 ', 4' , A 6'-trimethylbiphenyl-3-yl group, a 5-methylbiphenyl-2-yl group, a 6-methylbiphenyl- Methylbiphenyl-4-yl group, 4'-methylbiphenyl-4-yl group, Ethyl biphenyl-4-yl group, 2 ', 4', 6'-triethylbiphenyl-4-yl group, Yl group, 4'-ethylbiphenyl-2-yl group, 2 ', 4', 6'-triethylbiphenyl- Biphenyl-4-yl group, 2 ', 4', 6'-tripropylbiphenyl-4-yl group, 6-propylbiphenyl- -Yl group, a 5-propylbiphenyl-2-yl group, a 4'-propylbiphenyl-2-yl group, a 2 ' Isopropyl biphenyl-4-yl group, 4'-isopropyl biphenyl-4-yl group, 2'- Isopropylbiphenyl-2-yl group, 2 ', 4', 6'-triisopropylbiphenyl-2-yl group, 3'- Butylbiphenyl-4-yl group, 4'-butylbiphenyl-4-yl group, 2 ', 4', 6'- Butylbiphenyl-2-yl group, 2 ', 4', 6'-tributylbiphenyl-2-yl group, 3- tert-butylbiphenyl-4-yl group, 4'-tert-butylbiphenyl-4-yl group, 2 ', 4', 6'- 3-yl group, 4'-tert-butylbiphenyl-3-yl group, 5-tert- A biphenyl-2-yl group, a 4'-tert-butylbiphenyl-2-yl group, a 2'or 4'6'- Yl group, a 2-methylpyridin-6-yl group, a 3-methylpyridin-2-yl group, a 2-methylpyridin- , A 3-methylpyridin-4-yl group, a 3-methylpyridin-5-yl group, Dimethylpyridin-4-yl group, 3,6-dimethylpyridin-3-yl group, 2,6-dimethylpyridin- Yl group, a 2-phenylpyridin-6-yl group, a 3-phenylpyridin-6-yl group, , 2-phenylpyridin-4-yl group, 2-phenylpyridin-4-yl group, 2-phenylpyridin-5-yl group, (2-pyridyl) phenyl group, 3- (2-pyridyl) phenyl group, 4- (4-pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 2- Phenyl naphthalene-4-yl group, a 1-phenylnaphthalen-5-yl group, a 1-phenylnaphthalen-5-yl group, Phenyl naphthalene-1-yl group, a 2-phenylnaphthalene-3-yl group, a 2-phenylnaphthalene-4-yl group, 2-phenylnaphthalen-4-yl group, 1-methylnaphthalen-4-yl group, 1-methylnaphthalen-4-yl group, Methylnaphthalen-1-yl group, 2-methylnaphthalen-3-yl group, 2-methylnaphthalen-1-yl group, Methylnaphthalen-4-yl group, 2-methylnaphthalen-5-yl group, 2-methylnaphthalen-6-yl group, 2- Reel, two-ply Phenanthren-3-yl group, a 1-phenylphenanthrene-4-yl group, a 1-phenylphenanthrene-2-yl group, , A 1-phenylphenanthrene-5-yl group, a 1-phenylphenanthrene-6-yl group, a 1-phenylphenanthrene-7-yl group, a 1-phenylphenanthrene- , 2-phenylphenanthrene-1-yl group, 2-phenylphenanthrene-3-yl group, 2-phenylphenanthrene-4-yl group, 2-phenylphenanthrene- , A 2-phenylphenanthrene-6-yl group, a 2-phenylphenanthrene-7-yl group, a 2-phenylphenanthrene-8-yl group, a 2-phenylphenanthrene- , 3-phenylphenanthrene-1-yl group, 3-phenylphenanthrene-2-yl group, 3-phenylphenanthrene- Yl group, 3-phenylphenanthrene-10-yl group, 4-phenylphenanthrene-1-yl group, , 4-phenylphenanthrene-2-yl group, 4-phenylphenanthrene-3-yl , A 4-phenylphenanthrene-5-yl group, a 4-phenylphenanthrene-6-yl group, a 4-phenylphenanthrene- Methylphenanthrene-3-yl group, 1-methylphenanthrene-4-yl group, 1-methylphenanthrene-5-yl group , 1-methylphenanthren-6-yl group, 1-methylphenanthren-7-yl group, 1-methylphenanthrene-8-yl group, , 2-methylphenanthrene-1-yl group, 2-methylphenanthrene-3-yl group, 2-methylphenanthrene- , 2-methylphenanthrene-10-yl group, 3-methylphenanthrene-1-yl group, 2-methylphenanthrene- , 3-methylphenanthrene-2-yl group, 3-methylphenanthrene-4-yl group, 3-methylphenanthrene- , 3-methylphenanthrene-8-yl group, 3-methylphenanthrene-9-yl group, 3- Methylphenanthrene-2-yl group, 4-methylphenanthrene-3-yl group, 4-methylphenanthrene-5-yl group, 4- Methylphenanthrene-9-yl group, 4-methylphenanthrene-10-yl group, 1- (4-methylphenanthren- 1-phenylanthracene-4-yl group, 1-phenylanthracene-5-yl group, 1-phenylanthracene-5-yl group, 1-phenylanthracene-9-yl group, 1-phenylanthracene-10-yl group, 2-phenylanthracene-1-yl group, A 2-phenylanthracene-6-yl group, a 2-phenylanthracene-7-yl group, a 2- A phenanthracene-1-yl group, a 9-phenylanthracene-2-yl group, a 9-phenylanthracene-9-yl group, A phenyl group, a 2-pyridyl group, a 1-phenylpyran-2-yl group, a 1-phenylpyranyl group, Yl group, a 1-phenylpyran-7-yl group, a 1-phenylpyran-8-yl group, 1-yl group, 2-phenylpyran-3-yl group, 2-phenylpyran-4-yl group, 2-phenylpyran-10-yl group, Yl group, a 2-phenylpyran-9-yl group, a 2-phenylpyran-10-yl group, A 9-phenylpyran-5-yl group, a 9-phenylpyran-2-yl group, Yl group, a 1-methylpyran-2-yl group, a 1-methylpyran-3-yl group, a 1-methylpyran- Methylpyran-7-yl group, 1-methylpyran-8-yl group, 1-methylpyran-9-yl group, - diary, 1 Methylpyran-1-yl group, 2-methylpyran-5-yl group, 2-methylpyran-1-yl group, Yl group, a 2-methylpyran-10-yl group, a 9-methylpyran-1-yl group, a 9- Methylpyran-4-yl group, 9-methylpyran-5-yl group, 9-methylpyran-6-yl group, Yl group, a fluoranthene-1-yl group, a fluoranthene-2-yl group, a fluoranthene-1-yl group, A fluoranthene-6-yl group, a fluoranthene-7-yl group, a fluoranthene-8-yl group, a fluoranthene-9-yl group, An acenaphthylene-1-yl group, an acenaphthylene-3-yl group, an acenaphthylene-4-yl group, an acenaphthylene-1-yl group, Yl group, a chrysene-1-yl group, a chrysene-2-yl group, a chrysene- 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, l-quinolyl group, 1- Isoquinolyl group, 8-isoquinolyl group, quinoxaline group, 5-isoquinolyl group, 6-isoquinolyl group, A quinazolin-4-yl group, a quinazolin-5-yl group, a quinazolin-6-yl group, a quinazolin-7-yl group, A pyrimidin-2-yl group, a pyrimidin-4-yl group, a pyrimidin-5-yl group, an acridine-1-yl group, an acridine- An acridine-4-yl group, an acridine-9-yl group, a phenanthridin-1-yl group, a phenanthridin-1-yl group , A phenanthridin-6-yl group, a phenanthridin-7-yl group, a phenanthridin-8-yl group, a phenanthridin-4-yl group, 9-yl group, phenanthridin-10-yl group, Benzo [h] quinolin-4-yl group, benzo [h] quinolin-2-yl group, benzo [h] quinolin- Yl group, benzo [h] quinolin-6-yl group, benzo [h] quinolin-7-yl group, benzo [h] 10-diol, and the like can be mentioned as preferable examples. Among these substituents, a phenyl group, a p-tolyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 3- (2-pyridyl) (3-pyridyl) phenyl group, a 2-pyridyl group, a 3-pyridyl group, a 2-phenylpyridin-6-yl group, 2-naphthyl group, a 1-phenanthryl group, a 2-phenanthryl group, a 2-phenanthryl group, a 3-phenylpyridin- Phenanthryl group or 9-phenanthryl group is preferable, and a phenyl group, p-tolyl group, biphenyl-3-yl group, biphenyl-4-yl group, 1-naphthyl group or 9-phenanthryl group is more preferable.

Ar ³ represents a monocyclic, fused or cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms (the group may be substituted by a fluorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, or a pyridyl group) A monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms (the group is selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a pyridyl group, a phenyl group, a naphthyl group, Or may be substituted with a halogen atom).

"Monocyclic ring having 6 to 18, connection or chukhwan aromatic hydrocarbon group" represented in Ar ^3, "C 1 -C 4 alkyl group", the number of carbon atoms that is composed only of "alkoxy group having 1 to 4 carbon atoms", "6-membered ring from 3 to Quot; monocyclic, fused or cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms substituted with a fluorine atom ", monocyclic ring having 6 to 18 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, Linking or condensed aromatic hydrocarbon group having 6 to 18 carbon atoms substituted with a phenyl group "," monocyclic, linking or condensed aromatic hydrocarbon group having 6 to 18 carbon atoms substituted with an alkoxy group having 1 to 4 carbon atoms "," monocyclic, Quot ;, " monocyclic, fused or condensed aromatic hydrocarbon group having 6 to 18 carbon atoms substituted with pyridyl group "," monocyclic ring having 3 to 13 carbon atoms substituted with fluorine atom, Quot; is a monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms "," a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms substituted with an alkoxy group having 1 to 4 carbon atoms A monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group substituted with a phenyl group, "and a" monocyclic ring having 3 to 13 carbon atoms substituted with a pyridyl group, or a cyclic nitrogen-containing aromatic hydrocarbon group substituted with a pyridyl group " As the aromatic hydrocarbon group ", substituents such as those exemplified for Ar ¹ or Ar ² can be exemplified.

Examples of the monocyclic or cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms composed of only 6-membered rings substituted with a biphenyl group in Ar ³ include biphenylpyridyl group, biphenylpyrazyl group, biphenylpyrimidyl group, Preferable examples include a polysulfide, a biphenyltriazole, a biphenylquinolyl group, a biphenylisoquinolyl group, a biphenylphenanthryl group, a biphenylbenzoquinolyl group, and a biphenylacridyl group.

The monocyclic or cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms and composed of only 6-membered rings substituted with a naphthyl group in Ar ³ is not particularly limited, but a naphthylpyridyl group, a naphthylpyridyl group, Naphthyltriazinyl group or naphthylquinolyl group may be mentioned as preferred examples.

Ar ³ has 3 to 13 carbon atoms which is composed of a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms (the group may be substituted with a phenyl group or a pyridyl group) or a 6-membered ring only in view of excellent electron- (The group may be substituted with a phenyl group, a biphenyl group, or a naphthyl group), and a phenyl group, a naphthyl group, or a biphenyl group (these groups are substituted with a phenyl group or a pyridyl group) Or a monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 9 carbon atoms (the group may be substituted with a phenyl group, a biphenyl group or a naphthyl group), more preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group , A pyridylphenyl group, a pyridyl group, a pyrazyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, a phenylpyridyl group, More preferably a phenyl group, a biphenyl group, a naphthyl group, a phenyl group, a biphenyl group, a biphenyl group, a biphenyl group, a thienyl group, , A pyridyl group, a phenylpyridyl group, a pyrazyl group, a pyrimidyl group, a quinolyl group or an isoquinolyl group.

Specific examples of Ar ³ include, but are not limited to, a phenyl group, a p-tolyl group, an m-tolyl group, an o-tolyl group, a 2,4-dimethylphenyl group, Ethylphenyl group, 4-ethylphenyl group, 2,4-diethylphenyl group, 3,5-diethylphenyl group, 2-propylphenyl group, 3-propylphenyl group, Isopropylphenyl group, a 2,4-diisopropylphenyl group, a 3,5-diisopropylphenyl group, a 2-butylphenyl group, a 2-methylphenyl group, Butylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, Di-tert-butylphenyl group, 3,5-di-tert-butylphenyl group, biphenyl-2-yl group, biphenyl- , 2'-methylbiphenyl-4-yl group, 4'-methylbai Methylbiphenyl-3-yl group, a 5'-methylbiphenyl-4-yl group, a 2'- Methyl biphenyl-3-yl group, 2'-methylbiphenyl-3-yl group, 4'- Methylbiphenyl-2-yl group, 2'-methylbiphenyl-2-yl group, 4'-methylbiphenyl-2-yl group, 2-yl group, 6,2'-dimethylbiphenyl-2-yl group, 2 ', 4', 6'-trimethylbiphenyl- Ethyl biphenyl-3-yl group, 4'-ethylbiphenyl-3-yl group, 5-ethylbiphenyl-4-yl group, Yl group, 4'-ethylbiphenyl-2-yl group, 2 ', 4', 6'-triethylbiphenyl- Propylbiphenyl-3-yl group, a 4'-propylbiphenyl-3-yl group, a 4'- Isopropylbiphenyl-4-yl group, 3-isopropylbiphenyl-4-yl group, Isopropylbiphenyl-3-yl group, 4'-isopropylbiphenyl-4-yl group, 2'4 ', 6'-triisopropylbiphenyl- Isopropylbiphenyl-2-yl group, 3'-yl group, 5'-isopropylbiphenyl-2-yl group, 4'- 4-yl group, 4'-butylbiphenyl-4-yl group, 2 ', 4', 6'-tributylbiphenyl- 2-yl group, 3-tert-butyl-2-yl group, 4'-yl group, 4'-tert-butylbiphenyl-4-yl group, 2'4'6'-tri-tert- -Yl group, 4'-tert-butylbiphenyl-3-yl group, 5-tert- 2-yl group, 2'-tri-butylbiphenyl-2-yl group, 2-pyridyl group, 3-pyridyl group, Yl group, a 2-methylpyridin-6-yl group, a 3-methylpyridin-2-yl group, a 2-methylpyridin- Methylpyridin-2-yl group, a 4-methylpyridin-3-yl group, a 2,6-di 3-yl group, 3,6-dimethylpyridin-4-yl group, 3,6-dimethylpyridin-4-yl group, Yl group, a 2-phenylpyridin-6-yl group, a 3-phenylpyridin-6-yl group, 2-phenylpyridin-4-yl group, 2-phenylpyridin-5-yl group, (2-pyridyl) phenyl group, 3- (2-pyridyl) phenyl group, 4- (4-pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 2- A naphthyl group, a 2-naphthyl group, a 1-phenylnaphthalen-2-yl group, a 1-phenylnaphthalen-3-yl group, a 1-phenylnaphthalen- 1-yl group, 2-phenylnaphthalen-3-yl group, 2-phenylnaphthalen-4-yl group, 2-phenylnaphthalen- Phenylnaphthalen-4-yl group, 1-methylnaphthalene-5-yl group, 2-phenylnaphthalen-6-yl group, 2- Methyl naphthalene-1-yl group, 2-methylnaphthalen-3-yl group, 2-methyl naphthalene-2-yl group, A naphthalene-4-yl group, a 2-methylnaphthalen-5-yl group, a 2-methylnaphthalen-6-yl group, Phenantholyl , 1-phenylphenanthrene-3-yl group, 1-phenylphenanthrene-4-yl group, 1-phenylphenanthrene-2-yl group, A 1-phenylphenanthrene-9-yl group, a 1-phenylphenanthrene-9-yl group, a 1-phenylphenanthrene-6-yl group, A 2-phenylphenanthrene-4-yl group, a 2-phenylphenanthrene-5-yl group, a 2-phenylphenanthrene- 2-phenylphenanthren-9-yl group, 2-phenylphenanthrene-10-yl group, 3-phenylphenanthrene-6-yl group, 3-phenylphenanthrene-5-yl group, 3-phenylphenanthrene-6-yl group, 3-phenylphenanthrene-2-yl group, Yl group, 3-phenylphenanthrene-10-yl group, 4-phenylphenanthrene-1-yl group, 4-phenylphenanthrene- Phenylphenanthrene-2-yl group, 4-phenylphenanthrene-3-yl group, 4- Phenanthren-9-yl group, 4-phenylphenanthrene-9-yl group, 4-phenylphenanthrene-6-yl group, Methylphenanthrene-3-yl group, 1-methylphenanthrene-4-yl group, 1-methylphenanthrene-5-yl group, 1-methyl Yl group, 1-methylphenanthrene-10-yl group, 1-methylphenanthrene-10-yl group, 2-methyl Methylphenanthrene-4-yl group, 2-methylphenanthrene-5-yl group, 2-methylphenanthrene-6-yl group, 2-methyl Methylphenanthrene-10-yl group, a 3-methylphenanthrene-1-yl group, a 3-methylphenanthrene-9-yl group, Methylphenanthren-5-yl group, 3-methylphenanthren-6-yl group, 3-methylphenanthren-7-yl group, 3-methyl A phenanthren-8-yl group, a 3-methylphenanthrene-9-yl group, And n is an integer of 1 to 4, and n is an integer of 0 to 3. The term " naphthylthien-2-yl group " Yl group, 4-methylphenanthrene-10-yl group, 4-methylphenanthrene-8-yl group, 4-methylphenanthrene- 1-phenylanthracene-4-yl group, 1-phenylanthracene-5-yl group, 1- 1-phenylanthracene-10-yl group, 2-phenylanthracene-10-yl group, 2-phenylanthracene- A phenanthracene-6-yl group, a 2-phenylanthracene-7-yl group, a 2-phenylthiophenanthracene-5-yl group, Anthracene-8-yl group, 2-phenylanthracene-9-yl group, 2-phenylanthracene-10-yl group, , A 9-phenylanthracene-4-yl group, a 9-phenylanthracene-5-yl group, a 1-pyrenyl group, Yl group, a 1-phenylpyran-8-yl group, a 1-phenylpyran-4-yl group, Yl group, a 2-phenylpyran-4-yl group, a 2-phenylpyran-5-yl group, Yl group, 2-phenylpyrylene-10-yl group, 9-phenylpyrene-9-yl group, Yl group, a 9-phenylpyran-5-yl group, a 9-phenylpyran-6-yl group, Methylpyran-2-yl group, a 1-methylpyran-3-yl group, a 1-methylpyran-8-yl group, Methylpyran-8-yl group, 1-methylpyran-9-yl group, 1-methylpyran-6-yl group, -methyl Yl group, 2-methylpyrylene-5-yl group, 2-methylpyrylene-6-yl group, Methylpyran-9-yl group, a 9-methylpyran-1-yl group, a 9-methylpyran-8-yl group, Yl group, a 9-methylpyrylene-6-yl group, a 9-methylpyrrene-7-yl group, Yl group, a fluoranthene-1-yl group, a fluoranthene-2-yl group, a fluoranthene-3-yl group, Yl group, fluoranthen-5-yl group, fluoranthene-6-yl group, fluoranthen-7-yl group, fluoranthene-8-yl group, fluoranthene- An acenaphthylene-1-yl group, an acenaphthylene-4-yl group, an acenaphthylene-1-yl group, Yl group, a chrysene-1-yl group, a chrysene-2-yl group, a chrysene-5-yl group, A 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group, Isoquinolyl group, 8-isoquinolyl group, quinoxalin-2-yl group, 4-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, A quinazolin-5-yl group, a quinazolin-6-yl group, a quinazolin-6-yl group, a quinazolin- A pyrimidin-2-yl group, a pyrimidin-4-yl group, a pyrimidin-5-yl group, an acridine-1-yl group, an acridine- An acridine-2-yl group, an acridine-3-yl group, an acridine-4-yl group, an acridine-9-yl group, a phenanthridin- A phenanthridin-6-yl group, a phenanthridin-7-yl group, a phenanthridin-8-yl group, a phenanthridin-4-yl group, A 9-yl group, a phenanthridine-10-yl group, Yl group, benzo [h] quinolin-2-yl group, benzo [h] quinolin-3-yl group, benzo [h] Yl group, benzo [h] quinolin-6-yl group, benzo [h] quinolin-7-yl group, benzo [h] quinolin- (Biphenyl-4-yl) pyridin-4-yl group, 2- (biphenyl-4-yl) pyridin- Yl group, 2- (biphenyl-3-yl) pyridin-5-yl group, 2- (Biphenyl-4-yl) pyridin-5-yl group, 3- (biphenyl- Yl) pyridin-2-yl group, 4- (biphenyl-3-yl) pyridin- (Biphenyl-4-yl) pyrimidin-2-yl group, 2- (biphenyl- Yl) pyrimidin-2-yl group, 4- (biphenyl-4-yl) (Biphenyl-3-yl) pyrimidin-2-yl group, 2- (biphenyl- (Biphenyl-3-yl) pyrimidin-5-yl group, 4- Yl group or a 2- (biphenyl-3-yl) pyrazin-5-yl group, 6- (1-naphthyl) pyridine- (1-naphthyl) pyridin-2-yl group, 5- (1-naphthyl) pyridin- (2-naphthyl) pyridin-3-yl group, 6- (2-naphthyl) pyridin- A 5- (2-naphthyl) pyridin-1-yl group, or a 5- (2-naphthyl) Naphthyl) pyrazin-1-yl group, and the like. Among these substituents, preferred are a phenyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 2-pyridyl group, a 3-pyridyl group, (3-pyridyl) phenyl group, a 2-pyridyl group, a 3-pyridyl group, a 2-phenylpyridine-6 3-phenylpyridin-6-yl group, 1-naphthyl group, 2-naphthyl group, 2-naphthyl group, 2-phenylpyridin-4-yl group, Quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-quinolyl group, 3-quinolyl group, 4-quinolyl group, Isoquinolyl group, 8-isoquinolyl group, 2-phenanthrityl group, or 6- (4-isoquinolyl group, 2-naphthyl) pyridin-3-yl group is more preferable and a phenyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 2-pyridyl group, a 3-pyridyl group, 1-iso Quinolyl group, more preferably a 3-isoquinolyl group, or 4-isoquinolyl.

Provided that either one of Z ¹ and Z ² represents a nitrogen atom and the other represents CH.

When this compound is used as a part of the constituent components of the organic electroluminescent device, effects such as high luminous efficiency, long life, and low voltage can be obtained. Particularly, this effect is remarkable when used as an electron transporting layer.

The compound represented by the general formula (1) is more preferably represented by the following general formula (1) 'or (1)' in view of excellent properties as an electron transporting material.

(In the general formulas (1) 'and (1)', Ar ¹ , Ar ² , Ar ³ and two Ar ⁴ , Z ¹ and Z ² have the same meanings as in the general formula (1).)

Specific examples of the particularly preferable compound of the compound represented by the general formula (1) include the following (A-1) to (A-288), but the present invention is not limited thereto.

Next, the production method of the present invention will be described.

The triazine compound (1) of the present invention can be prepared by reacting the triazine compound (1) in the presence of a base or in the absence of a base in the presence of a palladium catalyst,

(In the reaction formula (1), Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Z ¹ and Z ² each represent the same substituent as described above, and Y ¹ and Y ² each independently represent a leaving group described below. M ¹ and M ² each independently represent a substituent described later.)

Reaction formula (2)

(In the reaction formula (2), Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Z ¹ and Z ² each represent a substituent as defined above.) Y ¹ and Y ² each independently represent a leaving group described below. M ¹ and M ² each independently represent a substituent described later.)

Reaction formula (3)

(In the formula (3), Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Z ¹ and Z ^{2 each} represent a substituent as described above, Y ³ represents a leaving group described later, and M ³ represents a substituent .),

Or (4)

(In the formula (4), Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Z ¹ and Z ^{2 each} represent a substituent as described above, Y ⁴ represents a leaving group to be described later, and M ⁴ represents a substituent .)

As shown in FIG.

Hereinafter, the compound represented by the general formula (2) is referred to as the compound (2). The same applies to the compounds (3) to (10).

M ¹ , M ² , M ³ and M ⁴ each independently represent ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ . However, R ¹ and R ² are, each independently, a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group or a phenyl group of 4 from having 1, R ⁴ is a 4-from a hydrogen atom, a C 1 An alkyl group or a phenyl group, and two R ⁴ groups of B (OR ⁴ ) ₂ may be the same or different. The two R ⁴ may be monosubstituted to form a ring including an oxygen atom and a boron atom.

Examples of ZnR ¹ and MgR ² include ZnCl ² , ZnBr, ZnI, MgCl 2, MgBr, and MgI.

Examples of Sn (R ³ ) ₃ include Sn (Me) ₃ and Sn (Bu) ₃ .

Examples of B (OR ⁴ ) ₂ include B (OH) ₂ , B (OMe) ₂ , B (OiPr) ₂ and B (OBu) ₂ . Examples of B (OR ⁴ ) _{2 in} the case where two R ⁴ are combined to form a ring including an oxygen atom and a boron atom include the groups represented by the following (C-1) to (C-6) And the group represented by (C-2) is preferred in view of good yield.

The compound (3) used in the reaction formula (1) or the reaction formula (2) is, for example, a compound represented by the formulas [0105] to [0121] of JP 2005-268199, Can be produced by combining the methods disclosed in publications [0061] to [0076] of JP-A No. 2001-335516 or [0047] to [0082] of JP-A No. 2001-335516. As the compound (3), the following (B-1) to (B-18) can be exemplified, but the present invention is not limited thereto.

The compound (4) used in Reaction Scheme (1) or Reaction Scheme (2) can be synthesized by a method disclosed in, for example, JP-A-2008-280330 [0061] to [0076] Can be produced by using the method disclosed in JP-A-2001-335516 and the method disclosed in JP-A-2001-335516. M ² in the compound (4) may be the same as the substituent described above for M ¹ . As the compound (4), the following (D-1) to (D-20) can be exemplified, but the present invention is not limited thereto.

The compound (6) used in the reaction formula (3) can be exemplified by a skeleton in which M ² of the compound (4) is substituted with Y ³ .

The compound (8) used in the reaction formula (4) can be exemplified by a skeleton wherein M ¹ of the compound (3) is substituted with Y ⁴ .

The Y ³ of the compound (6) and the Y ⁴ of the compound (8) each independently represent a leaving group and are not particularly limited. Examples thereof include a chlorine atom, a bromine atom, an iodine atom or a triflate, . Of these, a bromine atom or a chlorine atom is preferable in that the reaction yield is good. However, it may be preferable to use a triplate from the availability of the raw material.

Y ¹ and Y ² in the compound (2) each independently represent a leaving group, and the leaving group is not particularly limited, and examples thereof include a chlorine atom, a bromine atom, an iodine atom or a triflate. Of these, a bromine atom or a chlorine atom is preferable in that the reaction yield is good. Further, in order to improve the selectivity of the reaction, it is more preferable that Y ¹ and Y ² have other leaving groups.

Next, the reaction formula (1) will be described. "Process 1" is a process for obtaining a compound (9) as a synthetic intermediate by reacting a compound (2) with a compound (3) in the presence or absence of a base in the presence of a palladium catalyst, By applying the reaction conditions of a typical coupling reaction such as a Suzuki-Miyaura reaction, a Negishi reaction, a Tamao-Kumada reaction, and a Stille reaction, The desired product can be obtained in a satisfactory yield.

Examples of the palladium catalyst that can be used in "Step 1" include palladium chloride, palladium acetate, palladium trifluoroacetate, and palladium nitrate. (Triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium and dichloro (1, 2-diisopropylbenzene) palladium, , 1'-bis (diphenylphosphino) ferrocene) palladium, and the like. Among these, a palladium complex having a tertiary phosphine as a ligand is more preferable in view of a good reaction yield, and a palladium complex having triphenylphosphine as a ligand is particularly preferable because it is easy to obtain and the reaction yield is good.

The palladium complex having a tertiary phosphine as a ligand can be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or a complex compound. Examples of usable tertiary phosphines include triphenylphosphine, trimethylphosphine, tributylphosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, (Diphenylphosphino) -2'- (N, N-dimethylamino) biphenyl, 2- (di-tert-butyl Bis (diphenylphosphino) ethane, 1,3-bis (diphenylphosphino) biphenyl, bis (diphenylphosphino) ) Propane, 1,4-bis (diphenylphosphino) butane, 1,1'-bis (diphenylphosphino) ferrocene, tri (2-furyl) phosphine, tri Bis (diphenylphosphino) -1,1'-binaphthyl, 2-dicyclohexylphosphino-2 ', 4' 6'-triisopropylbiphenyl, and the like. 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl or triphenylphosphine is preferred because it is readily available and has a good reaction yield. The molar ratio of the tertiary phosphine to the palladium salt or complex is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 in terms of good reaction yield.

Examples of the base which can be used in "Process 1" include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, potassium phosphate, sodium phosphate, sodium fluoride, potassium fluoride and cesium fluoride And potassium carbonate is preferable in that the yield is good. The molar ratio of the base to the compound (3) is preferably from 1: 2 to 10: 1, more preferably from 1: 1 to 3: 1 in terms of good yield.

The molar ratio of the compound (2) to the compound (3) used in the " process 1 " is preferably 1: 2 to 5: 1, and more preferably 1: 2 to 2: 1.

As a solvent which can be used in the " Process 1 ", water, dimethylsulfoxide, dimethylformamide, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, toluene, benzene, diethylether, Or xylene, and these may be used in appropriate combination. It is preferable to use dioxane or a mixed solvent of THF and water in view of good yield.

&Quot; Process 1 " can be carried out at a temperature appropriately selected from 0 ° C to 150 ° C, and more preferably at 50 ° C to 100 ° C from the viewpoint of good yield.

Compound (9) is obtained by carrying out usual treatment after the termination of " process 1 ". If necessary, it may be purified by recrystallization, column chromatography or sublimation. Is a method for obtaining triazine compound (1) of the present invention by reacting compound (9) with compound (4) optionally in the presence of a base in the presence of a palladium catalyst, and the Suzuki- By applying the reaction conditions of a typical coupling reaction such as a Urea reaction, a Negishi reaction, a Tamao-Kumar reaction, and a Stille reaction, the desired product can be obtained in a satisfactory yield. &Quot; Process 2 " can be selected from reaction conditions similar to those described in " Process 1 ". However, the reaction conditions need not be the same as those in " Process 1 ". The triazine compound (1) can also be synthesized by adding the compound (4) to the reaction system of the "Step 1" without isolating the compound (9) as a synthetic intermediate. After completion of the " process 2 ", it may be purified by recrystallization, column chromatography or sublimation, if necessary.

Next, the reaction formula (2) will be described. "Step 3" is a method of reacting compound (2) with compound (4) optionally in the presence of a base in the presence of a palladium catalyst to obtain compound (10) as a synthetic intermediate, and Suzuki-Miyaura reaction By applying the reaction conditions of a typical coupling reaction such as reaction, Negishi reaction, Tamao-Kumar reaction, Stille reaction and the like, the desired product can be obtained in good yield. &Quot; Process 3 " can select reaction conditions such as those exemplified in " Process 1 ". However, the reaction conditions need not be the same as those in " Process 1 ". After completion of the " process 3 ", it may be purified by recrystallization, column chromatography or sublimation, if necessary. "Step 4" is a method for obtaining the triazine compound (1) of the present invention by reacting the compound (10) with the compound (3) in the presence of a base optionally in the presence of a palladium catalyst, By applying the reaction conditions of a typical coupling reaction such as a Urea reaction, a Negishi reaction, a Tamao-Kumar reaction, and a Stille reaction, the desired product can be obtained in a satisfactory yield. The " process 4 " can select the reaction conditions similar to the conditions shown in " process 1 ". However, the reaction conditions need not be the same as those in " Process 1 ". Alternatively, the triazine compound (1) may be synthesized by adding the compound (3) to the reaction system of the "Step 3" without isolating the compound (10) as a synthetic intermediate. After completion of the " Step 4 ", it may be purified by recrystallization, column chromatography or sublimation, if necessary.

Next, the reaction formula (3) will be described. The compound (5) used in the " Step 5 " can be synthesized from the compound (9) by using a reaction for synthesizing a general organometallic compound (for example, Angew.Chem.Int. Ed. 2007, 46, 5359-5363) Can be synthesized. Is a method for obtaining triazine compound (1) of the present invention by reacting compound (5) with compound (6) optionally in the presence of a base in the presence of a palladium catalyst, and the Suzuki- By applying the reaction conditions of a typical coupling reaction such as a Urea reaction, a Negishi reaction, a Tamao-Kumar reaction, and a Stille reaction, the desired product can be obtained in a satisfactory yield.

Examples of the palladium catalyst that can be used in " Step 5 " include palladium catalysts similar to those shown in " Step 1 ". Among them, a palladium complex having a tertiary phosphine as a ligand is more preferable from the viewpoint of a good reaction yield, and a palladium complex having triphenylphosphine as a ligand is particularly preferable in view of easy availability and good reaction yield .

The palladium complex having a tertiary phosphine as a ligand can be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or a complex compound. As the tertiary phosphine which can be used at this time, there is a tertiary phosphine similar to that shown in " Process 1 ". 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl or triphenylphosphine is preferred because it is readily available and has a good reaction yield. The molar ratio of the tertiary phosphine to the palladium salt or complex is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 in terms of good reaction yield. The base usable in " Step 5 " includes bases similar to those shown in " Step 1 ". The molar ratio of the base to the compound (5) is preferably from 1: 2 to 10: 1, more preferably from 1: 1 to 3: 1 in terms of good yield. The molar ratio of the compound (5) to the compound (6) used in " Step 5 " is preferably 1: 5 to 2: 1 and more preferably 1: 1 to 1: 3 in view of good yield. As the solvent which can be used in " Process 5 ", the same solvents as those shown in " Process 1 " can be mentioned. It is preferable to use dioxane or a mixed solvent of THF and water in view of good yield. &Quot; Step 5 " can be conducted at a temperature appropriately selected from 0 DEG C to 150 DEG C, and more preferably from 50 DEG C to 100 DEG C from the viewpoint of good yield. After completion of " Step 5 ", purification may be carried out by recrystallization, column chromatography or sublimation, if necessary.

Next, the reaction formula (4) will be described. Compound (7) used in " Step 6 " can be synthesized from compound (10) using a reaction for synthesizing a general organometallic compound (for example, Angew.Chem.Int. Ed. 2007, 46, 5359-5363) Can be synthesized. "Step 6" is a method for obtaining the triazine compound (1) of the present invention by reacting the compound (7) with the compound (8) in the presence of a base optionally in the presence of a palladium catalyst, By applying the reaction conditions of a typical coupling reaction such as a Urea reaction, a Negishi reaction, a Tamao-Kumar reaction, and a Stille reaction, the desired product can be obtained in a satisfactory yield. In " Process 6 ", reaction conditions similar to those shown in " Process 5 " can be selected. However, it need not be a reaction condition such as " Step 5 ". After completion of " Step 6 ", it may be purified by recrystallization, column chromatography or sublimation, if necessary.

The triazine compound (1) of the present invention is effective when used as a part of constituent components of an organic electroluminescent device. Particularly, when used as an electron transporting layer, effects such as long lifetime, high efficiency, and low voltage can be obtained as compared with conventional devices. When the triazine compound (1) of the present invention is used as a material for an organic electroluminescence device, it can also be used as a co-deposition film with any organic metal species, organic compound or inorganic compound.

The method for producing the thin film for an organic electroluminescence device comprising the triazine compound (1) of the present invention is not particularly limited, but it is possible to form a film by a vacuum vapor deposition method. The film formation by the vacuum vapor deposition method can be performed by using a general-purpose vacuum vapor deposition apparatus. The degree of vacuum of the vacuum chamber at the time of forming the film by the vacuum vapor deposition method may be appropriately selected depending on the tact time and manufacturing cost of the organic electroluminescent device, Is preferably about 1 x 10 < ^-2 > Pa to 1 x 10 < ^-5 > Pa. The deposition rate depends on the thickness of the film to be formed, but is preferably 0.005 to 1.0 nm / second. Since the solubility of the triazine compound (1) of the present invention is high in chloroform, dichloromethane, 1,2-dichloroethane, chlorobenzene, toluene, ethyl acetate or tetrahydrofuran, A spin coating method, an ink jet method, a casting method, a dipping method, or the like.

BRIEF DESCRIPTION OF THE DRAWINGS Fig.

1 is a cross-sectional view of an organic electroluminescent device manufactured in an embodiment (device evaluation).

[ Example ]

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

Synthesis Example 1

(14.8 g, 34.9 mmol), 4- (2-pyridyl) -1,3,5-triazin- Phenylboronic acid (9.04 g, 45.4 mmol) and tetrakis triphenylphosphine palladium (808 mg, 0.699 mmol) were suspended in tetrahydrofuran (250 mL) and heated to 60 < 0 > C. A 10% aqueous solution of NaOH (40 ml, 105 mmol) was slowly added dropwise thereto, followed by stirring for 3 hours. After cooling to room temperature, water (90 ml) was added to the reaction mixture, and the precipitate was collected by filtration. The resultant precipitate was purified by recrystallization with toluene to obtain the desired product, 2- [5-chloro-4 '- (2-pyridyl) biphenyl-3-yl] -Triazine as a white solid (yield 15.4 g, yield 88.5%).

¹ H-NMR (CDCl ₃ ): 7.27 (ddd, J = 5.7 Hz, 4.6 Hz, 2.3 Hz, 1H), 7.56-7.65 (m, 6H), 7.77-7.85 = 8.6 Hz, 2H), 8.72-8.74 (m, 2H), 8.77 (dd, J = 8.2 Hz, 1.4 Hz, 4H), 8.92 (t, J = 1.6 Hz, 1H).

Synthesis Example 2

To a solution of 2- [5-chloro-4 '- (2-pyridyl) biphenyl-3-yl] -4,6-diphenyl-1,3,5-triazine (6.86 g, 13.8 mmol ), Bis (pinacolato) diboron (5.26g, 20.7mmol), potassium acetate (4.06g, 41.4mmol), palladium acetate (31.0mg, 0.138mmol), 2-dicyclohexylphosphino- ', 4', 6'-triisopropylbiphenyl (131.5 mg, 0.276 mmol) was suspended in 1,4-dioxane (20 ml), and the mixture was heated to 100 ° C and stirred for 4 hours. Next, 200 ml of chloroform and 50 ml of water were added to the reaction solution and shaken, and only the organic layer was taken out. Next, magnesium sulfate was added to the organic layer, followed by dehydration and filtration. The low boiling point component of the obtained organic layer was distilled off and dissolved in 100 ml of chloroform. 700 ml of hexane was added thereto, and the mixture was stirred for 1 hour. The resultant precipitate was filtered to obtain the desired 4,6-diphenyl-2- [4 '- (2-pyridyl) -5- Yl) biphenyl-3-yl] -1,3,5-triazine (8.10 g, yield 99.7%) was obtained as a white solid .

_{^{1 H-NMR (CDCl 3)}} : 1.43 (s, 12H), 7.23-7.27 (m, 1H), 7.56-7.64 (m, 6H), 7.78 (ddd, J = 7.8Hz, 7.8Hz, 1.8Hz, 1H J = 8.5 Hz, 2H), 8.14 (d, J = 8.5 Hz, 2H), 8.33 (dd, J = 1.9 Hz, 1.1 Hz, 1H), 8.73 (ddd, J = 4.8Hz, 1.7Hz, 1.1Hz, 1H), 8.81 (dd, J = 7.8Hz, 1.6Hz, 4H), 9.12-9.14 (m, 2H).

Synthesis Example 3

(9.93 g, 34.6 mmol), 4'-bromochalcone (14.4 g, 51.8 mmol) and ammonium acetate (53.5 g, 691 mmol) were added to a solution of acetic acid ) And dimethylformamide (500 ml), and the mixture was stirred at 150 占 폚 for 19 hours. After cooling to room temperature, water (500 ml) was added to the reaction mixture, and the precipitate was collected by filtration. The precipitate obtained by filtration was washed with methanol to obtain an objective off-white powder of 2- (4-bromophenyl) -4,6-diphenylpyridine (yield: 10.4 g, yield 77.7%).

_{^{1 H-NMR (CDCl 3)}} ; 2H), 7.52-7.44 (m, 6H), 7.17 (d, 2H), 8.07 (d, 2H), 7.88 .

Example-1

Under argon stream, 4,6-diphenyl-2- [4 '- (2-pyridyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Yl) -1,3,5-triazine (4.00 g, 6.80 mmol) and 2- (4-bromophenyl) -4,6-diphenylpyridine (3.15 g, 8.15 2, 4 ', 6'-triisopropylbiphenyl (129.6 mg, 0.271 mmol) and potassium carbonate (2.44 g, g, 17.7 mmol) was suspended in a mixed solvent of tetrahydrofuran (75 ml) and water (17 ml), heated to 70 占 폚 and stirred for 19 hours. After cooling to room temperature, water (100 ml) was added to the reaction mixture, and the precipitate was collected by filtration. The resulting precipitate was purified by recrystallization with toluene and silica gel chromatography (developing solvent: a mixed solvent of chloroform and hexane 2: 1) to obtain the desired product, 4,6-diphenyl-2- [4- Yl) -1,3,5-triazine (compound A (1-tert-Butylpyridin-2-yl) -127) as a white solid (yield 3.35 g, yield 64.2%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.26 (ddd, J = 6.0Hz, 4.8Hz, 1.4Hz, 1H), 7.44-7.65 (m, 12H), 7.78 (d, J = 6.9Hz, 2H ), 7.80 (dd, J = 7.3 Hz, 1.8 Hz, 1H), 7.83 (d, J = 7.8 Hz, 1H), 7.92-7.99 J = 8.5 Hz, 2H), 8.24 (dd, J = 8.4 Hz, 1.4 Hz, 2H), 8.40 , 1.0 Hz, 1H), 8.81 (dd, J = 8.1 Hz, 1.9 Hz, 4H), 9.06 (dt, J = 6.3 Hz, 1.6 Hz, 2H).

The Tg of the obtained Compound A-127 was 134 占 폚.

Synthesis Example 4

(25.0 g, 59.1 mmol) and 3-pyridine boronic acid (12.0 g, 59.1 mmol) were added to a solution of 2- , Tetrakis triphenylphosphine palladium (2.05 g, 1.77 mmol) and potassium carbonate (24.5 g, 177 mmol) were dissolved in a mixed solvent of tetrahydrofuran (500 ml) and water (177 ml) Suspended, heated to 70 캜 and stirred for 18 hours. Next, the reaction solvent was distilled off, and chloroform and water were added and dissolved again. Only the organic layer was taken out, magnesium sulfate was added, dehydrated, and then filtered. The off-white solid obtained by distilling off the low-boiling point component of the obtained organic layer was purified by recrystallization with toluene to obtain the objective 2- [5-chloro-3- (3-pyridyl) phenyl] 1,3,5-triazine as an off-white solid (yield 22.6 g, yield 90.9%).

¹ H-NMR (CDCl ₃ ): 7.45 (dd, J = 7.6 Hz, 4.8 Hz, 1H), 7.56-7.65 = 7.9 Hz, 1H), 8.68 (dd, J = 4.8 Hz, 1.6 Hz, 1H), 8.74-8.76 (m, 1H), 8.76 (d, J = 6.5 Hz, 4H), 8.86 8.99 (d, J = 2.2 Hz, 1 H).

Synthesis Example 5

A solution of 2- [5-chloro-3- (3-pyridyl) phenyl] -4,6-diphenyl-1,3,5-triazine (10.0 g, 23.8 mmol), bis 2-dicyclohexylphosphino-2 ', 4 ', 6 ', 6,7-dimethoxybenzoic acid (1.0 g, 35.7 mmol), potassium acetate (7.01 g, 71.4 mmol), palladium acetate '-Triisopropylbiphenyl (227 mg, 0.476 mmol) was suspended in 1,4-dioxane (400 ml), and the mixture was heated to 100 ° C and stirred for 18 hours. Next, 500 ml of chloroform and 100 ml of water were added to the reaction solution and shaken, and only the organic layer was taken out. The organic layer was dehydrated by adding magnesium sulfate and filtered. The low boiling point component of the obtained organic layer was distilled off, and then dissolved in 150 ml of chloroform. 1000 ml of hexane was added thereto and the mixture was stirred for 1 hour and the resultant precipitate was collected by filtration to obtain the desired 4,6-diphenyl-2- [3- (3-pyridyl) -5- 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] -1,3,5-triazine as a white solid (9.58 g, yield 78.6%).

¹ H-NMR (CDCl ₃ )? (Ppm): 1.42 (s, 12H), 7.43 (ddd, J = 7.8Hz, 4.8Hz, 0.7Hz, 1H), 7.56-7.64 J = 7.8 Hz, 2.3 Hz, 1.6 Hz, 1H), 8.23 (dd, J = 2.1 Hz, 1.0 Hz, 1H), 8.65 (dd, J = 4.9 Hz, 1.6 Hz, 1H) = 8.0 Hz, 1.4 Hz, 4H), 9.04 (dd, J = 2.5 Hz, 0.8 Hz, 1H), 9.08 (t, J = 1.9 Hz, 1H), 9.16 ).

Example-2

To a solution of 4,6-diphenyl-2- [3- (3-pyridyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Phenyl) -1,3,5-triazine (3.00 g, 5.85 mmol), 2- (4-bromophenyl) -4,6-diphenylpyridine (2.71 g, 7.03 mmol) 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl (55.8 mg, 0.117 mmol) and potassium carbonate (2.10 g, 15.2 mmol) Was suspended in a mixed solvent of tetrahydrofuran (35 ml) and water (15 ml), and the mixture was heated to 70 캜 and stirred for 20 hours. After cooling to room temperature, water (50 ml) was added to the reaction mixture, and the precipitate was collected by filtration. The obtained precipitate was purified by recrystallization with silica gel chromatography (developing solvent: chloroform) and toluene to obtain the desired product, 4,6-diphenyl-2- [4 '- (4,6- (Yield: 2.66 g, yield 65.8%) of 5- (3-pyridyl) -biphenyl-3-yl] -1,3,5-triazine (Compound A-37).

¹ H-NMR (CDCl ₃ )? (Ppm): 7.46-7.67 (m, 13H), 7.80 (dd, J = 8.3 Hz, 1.4 Hz, 2H) (t, J = 1.8 Hz, 1H), 8.12 (ddd, J = 7.2 Hz, 2.3 Hz, 1.7 Hz, 1H) J = 8.3 Hz, 1.3 Hz, 2H), 8.42 (d, J = 8.5 Hz, 2H), 8.72 (dd, J = 4.8 Hz, 1.6 Hz, 1H), 8.82 = 8.2 Hz, 1.4 Hz, 4H), 9.01 (t, J = 1.6 Hz, 1H), 9.11 (d, J = 2.2 Hz, 1H), 9.12 (t, J = 5.0 Hz, 1H).

The Tg of the obtained Compound A-37 was 122 占 폚.

Synthesis Example 6

(70.0 g, 0.166 mol) and 9-phenanthreneboronic acid (38.6 g, 0.166 mol) in a stream of argon were added to a solution of 2- (3-bromo-5-chlorophenyl) , 0.174 mol) and tetrakis (triphenylphosphine) palladium (3.83 g, 3.31 mmol) were suspended in tetrahydrofuran (1000 ml) and added dropwise to 4.0 M aqueous sodium hydroxide solution (124 ml, 0.497 mol). The resulting mixture was stirred at 70 占 폚 for 24 hours. After cooling, water (550 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. (Toluene), a white solid of the reaction intermediate 2- [3-chloro-5- (9-phenanthryl) phenyl] -4,6-diphenyl-1,3,5-triazine (yield 78.9 g , Yield: 92%).

Synthesis Example-7

2- (3-chloro-5- (9-phenanthryl) phenyl] -4,6-diphenyl-1,3,5-triazine (5.20 g, 10 mmol) , Bispinacolato diboron (3.81 g, 15 mmol), palladium acetate (22.5 mg, 0.10 mmol), 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl And potassium acetate (2.95 g, 30 mmol) were suspended in 1,4-dioxane (200 ml), and the mixture was stirred at 100 ° C for 4 hours. After cooling, the precipitated component was removed by filtration. Chloroform (200 ml) and water (100 ml) were added and stirred, followed by separation of the aqueous layer and the organic layer. Further, the aqueous layer was extracted three times with chloroform (50 ml) and combined with the organic layer. From the organic layer, the low boiling point component was concentrated under reduced pressure, dried and solidified to obtain a crude product. Hexane was added thereto, and the mixture was stirred and cooled while being cooled to 0 deg. C, and the obtained solid was collected by filtration. The resulting solid was dried under reduced pressure to give 2- [3 - {(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl} ) Phenyl] -4,6-diphenyl-1,3,5-triazine (yield 6.07 g, yield 99%).

¹ H-NMR (CDCl ₃ )? (Ppm): 1.43 (s, 12H), 7.51-7.75 (m, 10H), 7.82 ), 8.75-8.81 (m, 5H), 8.83 (brd, J = 8.2 Hz, 1H), 9.01 (brs, 1H), 9.24 (brs, 1H).

Example-3

A solution of 2- [3 - {(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl} -5- (9 (1.58 g, 2.59 mmol), 2- (4-bromophenyl) -4,6-diphenylpyridine (1.00 g, 2.59 mmol), tetrakis triphenylphosphine palladium (89.8 mg, 0.078 mmol), 10% aqueous NaOH solution (2.25 g, 7.77 mmol) and tetrahydrofuran And the mixture was stirred at 70 ° C for 2 hours. After cooling to room temperature, water (50 ml) was added to the reaction mixture, and the precipitate was collected by filtration. The precipitate obtained by filtration was washed successively with pure water, methanol and hexane to obtain a gray powder. The obtained gray powder was purified by recrystallization with toluene to obtain 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) -5- (9-phenanthryl) Phenyl-3-yl] -1,3,5-triazine (Compound A-165) (yield 1.53 g, yield 74.6%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.43-7.62 (m, 13H), 7.66 (t, J = 7.2Hz, 1H), 7.72 (t, J = 7.8Hz, 2H), 7.77 (dd, J = 8.5 Hz, 1.4 Hz, 2H), 7.91 (d, J = 7.4 Hz, 2H), 7.98 (d, J = 8.2 Hz, 4H), 8.04 (dd, J = 8.3 Hz, 1.0 Hz, 1H) J = 8.0 Hz, 1H), 8.23 (dd, J = 8.2 Hz, 1.4 Hz, 2H), 8.38 (d, J = 8.6 Hz, 2H), 8.78 J = 8.0 Hz, 1H), 8.94 (t, J = 1.6 Hz, 1H), 9.19 (t, 1.7 Hz, 1H).

The Tg of the obtained Compound A-165 was 152 占 폚.

Synthesis Example-8

2- (4-bromophenyl) -4,6-diphenylpyridine (15 g, 38.8 mmol) obtained in Synthetic Example 3 was dissolved in tetrahydrofuran (195 ml) under an argon stream, Lt; / RTI > To the obtained solution, 1.64M n-butyllithium / hexane solution (25.9 ml, 42.7 mmol) was slowly added dropwise, followed by stirring for 0.5 hours. To the obtained solution, triisopropyl borate (11.7 ml, 50.5 mmol) was slowly added dropwise and the mixture was stirred for 1 hour. The resulting solution was warmed to room temperature and stirred for 18 hours. To the obtained solution, 1.5 M aqueous sodium hydroxide (68 ml, 101 mmol) was added and stirred, and the precipitate was filtered off. The precipitate was washed with water and hexane and then dried in vacuo to obtain 4- (4,6-diphenylpyridin-2-yl) phenylboronic acid as a target intermediate (12.8 g, yield 93.7%).

Synthesis Example-9

2- (3-bromo-5-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (10.0 g, 23.73 mmol) (10.0 g, 28.5 mmol), tetrakis (triphenylphosphine) palladium (823 mg, 0.711 mmol) and potassium carbonate (9.84 g, 71.2 mmol) was suspended in a mixed solvent of tetrahydrofuran (261 ml) and water (71 ml). The resulting mixture was stirred at 70 占 폚 for 23 hours. After cooling, water (500 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the desired intermediate 2- [5-chloro-4 '- (4,6-diphenylpyridin-2- 1,3,5-triazine as an off-white solid (yield 13.7 g, yield 89.1%).

¹ H-NMR (CDCl ₃ )? (Ppm): 7,44-7.65 (m, 12H), 7.77 (dd, J = 8.4 Hz, 1.4 Hz, 2H), 7.85-7.88 (dd, J = 1.4 Hz, 1H), 7.97 (d, J = 1.4 Hz, 1H), 8.23 (brd, J = 7.2 Hz, 2H), 8.38 J = 2.0Hz, 1.5Hz, 1H), 8.79 (dd, J = 8.0Hz, 1.8Hz, 4H), 8.95 (t, J = 1.6Hz, 1H).

Synthesis Example-10

(12.0 g, 28.3 mmol) and phenylboronic acid (4.5 g, 36.8 mmol) were added to a solution of 2- (3-bromo-5-chlorophenyl) m mol) was suspended in 1,2-dimethoxyethane (120 ml), and 10% aqueous NaOH solution (34.0 g, 85.1 mmol) was added dropwise thereto over 3 minutes. Tetrakis triphenylphosphine palladium (655 mg, 0.56 mmol) was added to the resulting mixture, and the mixture was stirred at 80 占 폚 for 14 hours. After cooling to room temperature, water (150 ml) was added to the reaction mixture, and the precipitate was collected by filtration. The resulting solid was washed with water, methanol, and hexane. The solid was recrystallized (toluene) to obtain a white solid of the objective product, 2- (5-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (yield 11.5 g, yield 96 %).

Example-4

2- (5-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (1.5 g, 3.57 mmol) obtained in Synthesis Example-10, 4- (4,6-diphenylpyridin-2-yl) phenylboronic acid (1.63 g, 4.64 mmol), palladium acetate (16.0 mg, 0.07 mmol), 2- dicyclohexylphosphino- (68.1 mg, 0.142 mmol) and potassium carbonate (1.48 g, 10.7 mmol) were added to a mixture of tetrahydrofuran (50 ml) and water (10 ml) And suspended in a solvent. The resulting mixture was stirred at 70 占 폚 for 19 hours. After cooling, water (50 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the objective product, 4,6-diphenyl-2- [4- (4,6-diphenylpyridin- -5'-yl] -1,3,5-triazine (A-1) as a white solid (yield: 2.22 g, yield 90.1%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.43-7.64 (m, 15H), 7.78 (dd, J = 8.5Hz, 1.5Hz, 2H), 7.82 (dd, J = 8.2Hz, 1.3Hz, 2H J = 8.7 Hz, 1.4 Hz, 2H), 8.11 (t, J = 1.8 Hz, 1H), 8.24 (dd, J = 8.4 Hz, (D, J = 7.9 Hz, 1.5 Hz, 4H), 8.99 (t, J = 1.6 Hz, 1H), 9.05 J = 1.6 Hz, 1H).

The Tg of the obtained compound A-1 was 117 占 폚.

Synthesis Example-11

2- (3-bromo-5-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (8.46 g, 20.0 mmol) and 4-biphenylboronic acid g, 22.0 mmol) and tetrakis triphenylphosphine palladium (462 mg, 0.40 mmol) were suspended in tetrahydrofuran (100 ml), and 4N NaOH aqueous solution (15.0 ml, 60 mmol) Lt; / RTI > The resulting mixture was stirred at 75 占 폚 for 16 hours. After cooling to room temperature, water (150 ml) was added to the reaction mixture, and the precipitate was collected by filtration. The resulting solid was washed with water, methanol, and hexane. The solids were recrystallized (toluene) to give the desired product 2- (5-chloro-1,1 ': 4', 1 "-terphenyl- Azine as a white solid (yield 9.48 g, yield 95.6%).

Example 5

(5-chloro-1,1 ': 4', 1 "-terphenyl-3-yl) -4,6-diphenyl-1,3,5-tri Azine (1.5 g, 3.02 mmol), 4- (4,6-diphenylpyridin-2-yl) phenylboronic acid (1.27 g, 3.63 mmol) obtained in Synthesis Example-8, palladium acetate (13.6 mg, 2, 4 ', 6'-triisopropylbiphenyl (57.6 mg, 0.120 mmol) and potassium carbonate (1.25 g, 9.07 mmol) were dissolved in tetrahydrofuran (50 ml) and water (9 ml) .The obtained mixture was stirred for 19 hours at 70 DEG C. After cooling, water (50 ml) was added, the precipitated solid was filtered off, The resulting solid was recrystallized (toluene) to obtain the desired product, 4,6-diphenyl-2- [4- (4,6-diphenylpyridin-2-yl) (Yield 2.16 g, yield 93.0%) of 3 ', 1 ": 4", 1 "' -tetraphenyl-5'- yl] -1,3,5- .

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.38 (t, J = 7.4Hz, 1H), 7.44-7.65 (m, 14H), 7.70 (dd, J = 8.3Hz, 1.3Hz, 2H), 7.77 J = 8.6 Hz, 2H), 7.99 (d, J = 8.4 Hz, 2H), 7.92 (d, J = (T, J = 1.7 Hz, 1H), 8.24 (dd, J = 8.4 Hz, 1.5 Hz, 2H), 8.40 = 8.2 Hz, 1.5 Hz, 4H), 9.05 (d, J = 9.2 Hz, 2H).

The obtained Compound A-109 had a Tg of 129 占 폚.

Synthesis Example-12

(7.26 g, 26.1 mmol) and ammonium acetate (32.3 g, 420 mmol) were dissolved in acetic acid (250 ml) and a solution of diisobutylaluminum bromide Methyl formamide (250 ml), and the mixture was stirred at 150 占 폚 for 23 hours. After cooling to room temperature, water (500 ml) was added to the reaction mixture, and the precipitate was collected by filtration. The precipitate obtained by filtration was washed with methanol to obtain an objective off-white powder of the objective 4- (4-bromophenyl) -2,6-diphenylpyridine (yield: 1.14 g, yield: 35.2%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.44 (t, J = 7.5Hz, 2H), 7.51 (m, J = 7.5Hz, 4H), 7.60 (d, J = 8.6Hz, 2H), 7.65 (d, J = 8.8 Hz, 2H), 7.83 (s, 2H), 8.18 (dd, J = 8.5 Hz, 1.5 Hz, 4H).

Synthesis Example-13

4- (4-bromophenyl) -2,6-diphenylpyridine (4.9 g, 12.7 mmol) obtained in Synthesis Example-12 was dissolved in tetrahydrofuran (64 ml) under an argon stream, Lt; / RTI > To the obtained solution, 1.65M n-butyllithium / hexane solution (8.45 ml, 14.0 mmol) was slowly added dropwise, followed by stirring for 0.5 hours. To the obtained solution, triisopropyl borate (3.80 ml, 16.5 mmol) was slowly added dropwise and the mixture was stirred for 1 hour. The resulting solution was warmed to room temperature and stirred for 17 hours. To the obtained solution, 1.5 M aqueous sodium hydroxide (45 ml, 33.0 mmol) was added and stirred, and the precipitate was filtered off. The precipitate was washed with water and hexane and then dried in vacuo to obtain 4- (2,6-diphenylpyridin-4-yl) phenylboronic acid as a target intermediate (3.70 g, yield 83.0%).

Example-6

Under argon stream, a solution of 2- [5-chloro-4 '- (2-pyridyl) biphenyl-3-yl] -4,6-diphenyl-1,3,5-triazine 1.56 g, 3.02 mmol), 4- (2,6-diphenylpyridin-4-yl) phenylboronic acid (1.27 g, 3.62 mmol) obtained in Synthesis Example-13, and palladium acetate (13.6 mg, 0.060 mmol ), Potassium carbonate (1.25 g, 9.05 mmol) and 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl (57.5 mg, 0.12 mmol) were dissolved in tetrahydrofuran Ml) and water (9 ml). The resulting mixture was stirred at 70 占 폚 for 21 hours. After cooling, water (50 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the desired product, 4,6-diphenyl-2- [4- (2,6-diphenylpyridin- : An off-white solid (yield 1.26 g, yield 54.4%) of 3 ', 1 "-terphenyl-5'- yl] -1,3,5-triazine (A-136) was obtained.

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.25-7.29 (m, 1H), 7.45 (t, J = 7.6Hz, 2H), 7.50-7.55 (m, 4H), 7.57-7.63 (m, 6H ), 7.80 (t, J = 8.3 Hz, 1H), 7.84 (brd, J = 7.8 Hz, 1H), 7.94 (dd, J = 8.3 Hz, 2.1 Hz, 4H), 7.97-8.00 8.14 (d, J = 8.3 Hz, 1.4 Hz, 4H), 8.74 (ddd, J = 4.8 Hz, 1.8 Hz, 1.1 Hz, 1H), 8.81 (dd, J = 8.1 Hz, 1.9 Hz, 4H), 9.06 (dt, J = 7.7 Hz, 1.8 Hz, 2H).

The Tg of the obtained Compound A-136 was 134 占 폚.

Example-7

2- [5-chloro-4 '- (4,6-diphenylpyridin-2-yl) biphenyl-3-yl] -4,6-diphenyl- (1.50 g, 2.31 mmol), 3-quinolinic acid (480 mg, 2.77 mmol), 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl To a mixture of phenyl (44.0 mg, 0.092 mmol), palladium acetate (10.4 mg, 0.046 mmol) and potassium carbonate (958 mg, 6.93 mmol) in tetrahydrofuran (60 mL) and water (7 mL) Lt; / RTI > The resulting mixture was stirred at 70 占 폚 for 17 hours. After cooling, water (70 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the desired product, 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) -5- (3-quinolyl) 3-yl] -1,3,5-triazine (A-180) as an off-white solid (yield 1.35 g, yield 78.6%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.44-7.66 (m, 13H), 7.76 (dd, J = 8.2Hz, 1.4Hz, 1H), 7.78 (dd, J = 7.1Hz, 1.4Hz, 2H ), 7.93 (d, J = 1.4 Hz, 1H), 7.97-8.00 (m, 4H), 8.20-8.25 (m, 4H), 8.42 (Dt, J = 6.8 Hz, 1.7 Hz, 2H), 9.43 (d, J = 2.2 Hz, 1H), 8.82 (dd, J = 8.1 Hz, 1.9 Hz, 4H), 9.13

The Tg of the obtained Compound A-180 was 128 占 폚.

Example-8

2- [5-chloro-4 '- (4,6-diphenylpyridin-2-yl) biphenyl-3-yl] -4,6-diphenyl- (300 mg, 0.46 mmol), potassium carbonate (141 mg, 0.55 mmol) and 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane -2-yl) ISOquinoline (141.5 mg, 0.554 mmol) was suspended in a mixed solvent of tetrahydrofuran (8 ml) and water (1 ml) and heated to 70 占 폚. To the obtained mixture, palladium acetate (2.07 mg, 0.0092 mmol) and 2-dicyclohexylphosphino-2 ', 4', 6'- triisopropylbiphenyl (8.80 mg, 0.018 mmol) ), And the mixture was stirred at 70 占 폚 for 24 hours. After cooling, water (10 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the objective product, 4,6-diphenyl-2- [4 '- (4,6- diphenylpyridin- Yl] -1,3,5-triazine (A-173) as a white solid (Yield 309 mg, yield 90.0%).

¹ H-NMR (CDCl ₃ )? (Ppm): 7.45-7.61 (m, 12H), 7.68-7.79 (m, 4H), 7.92 J = 7.8 Hz, 1H), 8.23 (dd, J = 8.8 Hz, 1.4 Hz, 1H), 8.05 (brd, J = 6.8 Hz, (D, J = 8.4 Hz, 1.6 Hz, 4H), 8.91 (t, J = 1.6 Hz, 1H), 9.19 (t, J = 1.7 Hz, 1H), 9.36 (brs, 1H).

The Tg of the obtained Compound A-173 was 137 占 폚.

Example-9

2- [5-chloro-4 '- (4,6-diphenylpyridin-2-yl) biphenyl-3-yl] -4,6-diphenyl- (952 mg, 6.93 mmol) and 4- (3-pyridyl) phenylboronic acid (552 mg, 2.77 mmol) were dissolved in tetrahydrofuran (30 ml) and water (6 ml) and heated to 70 ° C. To the obtained mixture, palladium acetate (10.4 mg, 0.046 mmol) and 2-dicyclohexylphosphino-2 ', 4', 6'- triisopropylbiphenyl (44.0 mg, 0.092 mmol) ), And the mixture was stirred at 70 占 폚 for 18 hours. After cooling, water (30 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the desired product, 4,6-diphenyl-2- [4- (4,6-diphenylpyridin-2-yl) : An off-white solid (1.64 g, yield 92.4%) of 3 ', 1 "-terphenyl-5'-yl] -1,3,5-triazine (A-145) was obtained.

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.41 (ddd, J = 7.6Hz, 4.8Hz, 0.8Hz, 1H), 7.44-7.65 (m, 12H), 7.78 (d, J = 8.5Hz, 4H ), 7.92-7.99 (m, 7H), 8.15 (t, J = 1.7 Hz, 1H), 8.24 (dd, J = 8.3 Hz, 1.4 Hz, 2H) 8.63 (dd, J = 4.7 Hz, 1.6 Hz, 1H), 8.81 (dd, J = 8.0 Hz, 1.9 Hz, 4H) = 1.6 Hz, 1H), 9.08 (t, J = 1.6 Hz, 1H).

The obtained Compound A-145 had a Tg of 133 캜.

Example-10

2- [5-chloro-4 '- (4,6-diphenylpyridin-2-yl) biphenyl-3-yl] -4,6-diphenyl- 2-naphthaleneboronic acid (63.6 mg, 0.37 mmol), potassium carbonate (128 mg, 0.92 mmol), palladium acetate (1.38 mg, 0.0061 mmol) (5.87 mg, 0.012 mmol) was added to a mixed solvent of tetrahydrofuran (5 mL) and water (1 mL), and the mixture was stirred at room temperature for 2 hours. Lt; / RTI > The resulting mixture was stirred at 70 占 폚 for 21 hours. After cooling, water (5 ml) was added, and the precipitated solid was separated by filtration, and the solid was washed with water, methanol and hexane to obtain 4,6-diphenyl-2- [4 ' Yl) -1,3,5-triazine (A-164) as a white solid (Yield: 224.8 mg, yield 98.5 %).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.45-7.65 (m, 14H), 7.78 (dd, J = 8.3Hz, 1.6Hz, 2H), 7.91-8.04 (m, 8H), 8.23-8.26 ( m, 4H), 8.41 (d, J = 8.5 Hz, 2H), 8.82 (dd, J = 8.2 Hz, 2.1 Hz, 4H), 9.09 (dt, J = 6.1 Hz, 1.4 Hz, 2H).

The obtained Compound A-164 had a Tg of 122 占 폚.

Synthesis Example-14

(3.00 g, 7.10 mmol) and 1-naphthaleneboronic acid (1.46 g, 7.10 mmol) were added to a solution of 2- , Potassium carbonate (2.94 g, 21.3 mmol) and tetrakis (triphenylphosphine) palladium (246 mg, 0.21 mmol) were suspended in tetrahydrofuran (60 ml) Lt; / RTI > After cooling, water (100 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting crude product was purified by silica gel column chromatography (eluent: chloroform) and recrystallization (toluene) to obtain 2- [3-chloro-5- (1- Diphenyl-l, 3,5-triazine (yield: 2.88 g, yield 86.5%).

¹ H-NMR (CDCl ₃ )? (Ppm): 7.48-7.64 (m, 10H), 7.73 (dd, J = 2.1 Hz, 1.6 Hz, 1H), 7.91 (brd, J = 8.6 Hz, 1H) (brd, J = 4.0 Hz, 1H), 7.98 (brd, J = 3.6 Hz, 1H), 8.74-8.78 (m, 5H), 8.83 (dd, J = 2.3 Hz, 1.6 Hz, 1H).

Example-11

2- [3-chloro-5- (1-naphthyl) phenyl] -4,6-diphenyl-1,3,5-triazine obtained in Synthesis Example-14 (1.30 g, 2.77 mmol ), 4- (4,6-diphenylpyridin-2-yl) phenylboronic acid (1.17 g, 3.32 mmol) obtained in Synthesis Example-8, palladium acetate (12.4 mg, 0.055 mmol) (52.7 mg, 0.11 mmol) and potassium carbonate (1.15 g, 8.30 mmol) were dissolved in tetrahydrofuran (60 ml) and water (8 ml) Ml). The resulting mixture was stirred at 70 占 폚 for 22 hours. After cooling, water (50 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the desired product, 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) -5- (1-naphthyl) 3-yl] -1,3,5-triazine (A-163) (yield 1.81 g, yield 88.1%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.45-7.60 (m, 16H), 7.79 (brd, J = 6.8Hz, 2H), 7.93 (d, J = 1.4Hz, 1H), 7.97-8.07 ( J = 8.8 Hz, 2H), 8.80 (d, J = 8.5 Hz, 2H) 1.7 Hz, 1 H), 9.18 (t, J = 1.8 Hz, 1 H).

The Tg of the obtained Compound A-163 was 134 占 폚.

Example-12

2- [5-chloro-3- (3-pyridyl) phenyl] -4,6-diphenyl-1,3,5-triazine obtained in Synthetic Example 4 (1.30 g, 3.09 mmol ), 4- (2,6-diphenylpyridin-4-yl) phenylboronic acid (1.30 g, 3.71 mmol) obtained in Synthesis Example-13, palladium acetate (13.9 mg, 0.061 mmol) (58.9 mg, 0.12 mmol) and potassium carbonate (1.28 g, 9.27 mmol) were dissolved in tetrahydrofuran (45 ml) and water (9 ml) Ml). The resulting mixture was stirred at 70 占 폚 for 21 hours. After cooling, water (50 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the desired product, 4,6-diphenyl-2- [4 '- (2,6-diphenylpyridin-4-yl) -5- (3-pyridyl) 3-yl] -1,3,5-triazine (A-46) (yield 1.70 g, yield 79.4%).

¹ H-NMR (CDCl ₃ )? (Ppm): 7.46-7.57 (m, 7H), 7.59-7.68 (m, 6H), 7.95-7.99 (m, 4H), 8.00 J = 7.7 Hz, 1H), 8.13 (ddd, J = 7.8 Hz, 2.3 Hz, 1.6 Hz, 1H), 8.25 (dd, J = 8.6 Hz, 1.4 Hz, , 1.4 Hz, 1H), 8.82 (dd, J = 8.2 Hz, 2.0 Hz, 4H), 9.03 (t, J = 1.6 Hz, 1H), 9.11 (t, J = 1.6 Hz, 2H).

The Tg of the obtained Compound A-46 was 123 占 폚.

Example-13

2- (5-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (1.30 g, 3.10 mmol) obtained in Synthesis Example-10, (1.30 g, 3.72 mmol), palladium acetate (13.9 mg, 0.061 mmol), and 2-dicyclohexylphosphino- A mixture of 2 ', 4', 6'-triisopropylbiphenyl (59.0 mg, 0.12 mmol) and potassium carbonate (1.28 g, 9.29 mmol) in tetrahydrofuran (45 mL) And suspended in a solvent. The resulting mixture was stirred at 70 占 폚 for 22 hours. After cooling, water (50 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to give the desired product, 4,6-diphenyl-2- [4- (2,6-diphenylpyridin-4-yl) -1,1 ': 3' Yl] -1,3,5-triazine (A-10) (yield 1.55 g, yield 72.7%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.46-7.67 (m, 15H), 7.84 (dd, J = 8.2Hz, 1.4Hz, 2H), 7.94-7.98 (m, 4H), 8.00 (s, J = 7.9 Hz, 1.9 Hz, 4H), 9.03 (t, J), 8.25 (dd, J = = 1.4 Hz, 1H), 9.06 (t, J = 1.7 Hz, 1H).

The Tg of the obtained Compound A-10 was 121 占 폚.

Example-14

(5-chloro-1,1 ': 4', 1 "-terphenyl-3-yl) -4,6-diphenyl-1,3,5-tri Azine (1.30 g, 2.62 mmol), 4- (2,6-diphenylpyridin-4-yl) phenylboronic acid (1.10 g, 3.15 mmol) obtained in Synthesis Example-13, palladium acetate (11.8 mg, dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl (50.0 mg, 0.10 mmol) and potassium carbonate (1.09 g, 7.86 mmol) were dissolved in tetrahydrofuran (35 ml) and water (7 ml) .The obtained mixture was stirred for 23 hours at 70 DEG C. After cooling, water (50 ml) was added, the precipitated solid was filtered off, The resulting solid was recrystallized (toluene) to obtain the desired product, 4,6-diphenyl-2- [4- (2,6-diphenylpyridin-4-yl) (Yield 1.75 g, yield 86.8%) of 3 ', 1 ": 4", 1 "' -tetraphenyl-5'- yl] -1,3,5- .

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.41 (t, J = 7.5Hz, 1H), 7.46-7.67 (m, 14H), 7.72 (dd, J = 8.3Hz, 1.4Hz, 2H), 7.81 (d, J = 8.5 Hz, 2H), 7.91-8.00 (m, 8H), 8.16 (t, J = 1.8 Hz, 1H), 8.25 (dd, J = 8.6 Hz, 1.4 Hz, 4H), 8.83 , J = 8.1 Hz, 1.9 Hz, 4H), 9.07 (ddd, J = 4.9 Hz, 1.8 Hz, 1.7 Hz, 2H).

The Tg of the obtained Compound A-118 was 131 占 폚.

Synthesis Example-15

2- (3-bromo-5-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (5.00 g, 11.8 mmol) (6.25 g, 17.7 mmol), tetrakis (triphenylphosphine) palladium (410 mg, 0.354 mmol) and potassium carbonate (4.90 g, 35.5 mmol) was suspended in a mixed solvent of tetrahydrofuran (240 ml) and water (35 ml). The resulting mixture was stirred at 70 占 폚 for 20 hours. After cooling, water (200 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the desired intermediate 2- [5-chloro-4 '- (2,6-diphenylpyridin-4-yl) biphenyl- An off-white solid of 1,3,5-triazine (yield 4.17 g, yield 54.2%) was obtained.

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.46-7.67 (m, 12H), 7.88-7.95 (m, 5H), 7.98 (s, 2H), 8.25 (brd, J = 7.4Hz, 4H), 8.77 (brt, J = 1.8 Hz, 1H), 8.80 (dd, J = 8.1 Hz, 1.5 Hz, 4H), 8.95 (brt, J = 1.7 Hz, 1H).

Example-15

4-yl) biphenyl-3-yl] -4,6-diphenyl-1, 2-dicarboxylic acid obtained in Synthesis Example- (75 mg) was added to a solution of 3,5-triazine (1.50 g, 2.31 mmol), potassium carbonate (958 mg, 6.93 mmol) and 4-pyridineboronic acid (340 mg, 2.77 mmol) in tetrahydrofuran (6 ml), and the temperature was raised to 70 占 폚. Next, to the resulting mixture was added a solution of tetra (2-pyridyl) -1,3-dioxolane in the presence of palladium acetate (10.4 mg, 0.046 mmol) and 2-dicyclohexylphosphino-2 ', 4' (25 ml), and the mixture was stirred at 70 占 폚 for 19 hours. After cooling, water (100 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the desired product, 4,6-diphenyl-2- [4 '- (2,6-diphenylpyridin- 3-yl] -1,3,5-triazine (A-64) as a white solid (Yield 1.09 g, yield 68.2%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.48 (t, J = 7.2Hz, 2H), 7.55 (t, J = 7.6Hz, 4H), 7.60-7.68 (m, 6H), 7.76 (d, (D, J = 8.5 Hz, 1.4 Hz, 4H), 8.80 (s, 2H), 8.14 -8.84 (m, 6H), 9.06 (t, J = 1.8 Hz, 1H), 9.14 (t, J = 1.7 Hz, 1H).

The obtained Compound A-64 had a Tg of 130 캜.

Example-16

4-yl) biphenyl-3-yl] -4,6-diphenyl-1, 2-dicarboxylic acid obtained in Synthesis Example- (1.50 g, 2.31 mmol), potassium carbonate (958 mg, 6.93 mmol) and 6-phenyl-3- (4,4,5,5-tetramethyl- 2-yl) pyridine (780 mg, 2.77 mmol) was suspended in a mixed solvent of tetrahydrofuran (75 ml) and water (6 ml) and the temperature was raised to 70 ° C. Next, to the resulting mixture was added a solution of tetra (2-pyridyl) -1,3-dioxolane in the presence of palladium acetate (10.4 mg, 0.046 mmol) and 2-dicyclohexylphosphino-2 ', 4' (25 ml) was added, and the mixture was stirred at 70 占 폚 for 21 hours. After cooling, water (100 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the desired product, 4,6-diphenyl-2- [4 '- (2,6- diphenylpyridin- -Biphenyl-3-yl] -1,3,5-triazine (A-225) as an off-white solid (yield: 1.46 g, yield 82.3%).

¹ H-NMR (CDCl ₃ )? (Ppm): 7.46-7.50 (m, 3H), 7.52-7.57 (m, 6H), 7.59-7.68 (m, 6H), 7.94-8.00 (dd, J = 8.4 Hz, 1.4 Hz, 2H), 8.15 (t, J = 1.8 Hz, 1H), 8.21 (dd, J = 8.5 Hz, 2.5 Hz, 1H) (Dd, J = 8.1 Hz, 1.5 Hz, 4H), 9.10 (dt, J = 6.91 Hz, 1.7 Hz, 2H), 9.20 (brd, J = 2.2 Hz, 1H).

The obtained Compound A-225 had a Tg of 135 占 폚.

Example-17

2- [5-chloro-4 '- (4,6-diphenylpyridin-2-yl) biphenyl-3-yl] -4,6-diphenyl- (1.50 g, 2.31 mmol), potassium carbonate (958 mg, 6.93 mmol) and 6-phenyl-3- (4,4,5,5-tetramethyl- Dioxaborolan-2-yl) pyridine (780 mg, 2.77 mmol) was suspended in a mixed solvent of tetrahydrofuran (36 mL) and water (6 mL) and the temperature was raised to 70 ° C. Next, to the resulting mixture was added a solution of tetra (2-pyridyl) -1,3-dioxolane in the presence of palladium acetate (10.4 mg, 0.046 mmol) and 2-dicyclohexylphosphino-2 ', 4' A solution of hydrofuran (15 ml) was added, and the mixture was stirred at 70 占 폚 for 19 hours. After cooling, water (100 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to obtain the desired product, 4,6-diphenyl-2- [4 '- (2,4-diphenylpyridin-6-yl) -5- -Biphenyl-3-yl] -1,3,5-triazine (A-226) as an off-white solid (yield 1.60 g, yield 90.2%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.45-7.67 (m, 15H), 7.80 (dd, J = 8.3Hz, 1.4Hz, 2H), 7.95 (brd, J = 8.1Hz, 1H), 7.95 (dd, J = 8.7 Hz, 1.6 Hz, 2H), 8.01 (d, J = 1.3 Hz, 1H) 8.24 (dd, J = 8.6 Hz, 1.5 Hz, 2H), 8.43 (d, J = 8.5 Hz, 1H) , 2H), 8.83 (dd, J = 8.0 Hz, 1.8 Hz, 4H), 9.08 (t, J = 1.7 Hz, 1H), 9.13 (t, J = 1.7 Hz, 1H), 9.21 Hz, 1H).

The Tg of the obtained Compound A-226 was 133 占 폚.

Synthesis Example-16

2- [5-chloro-4 '- (4,6-diphenylpyridin-2-yl) biphenyl-3-yl] -4,6-diphenyl- (5.00 g, 7.70 mmol), bispinacolato diboron (2.35 g, 9.24 mmol), palladium acetate (34.6 mg, 0.15 mmol), 2-dicyclohexylphosphino- (147 mg, 0.31 mmol) and potassium acetate (2.27 g, 23.1 mmol) were suspended in 1,4-dioxane (200 ml) Lt; / RTI > After cooling, chloroform (200 ml) and water (100 ml) were added and stirred, and then the aqueous layer and the organic layer were separated. Further, the aqueous layer was extracted three times with chloroform (50 ml) and combined with the organic layer. The low boiling point component was distilled off under reduced pressure from the organic layer to obtain a dried solid. Hexane was added to the dried solid and stirred, followed by filtration to obtain a solid. The resulting solid was dried under reduced pressure to give 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) -5- (4,4,5,5- Yl)] biphenyl-3-yl] -1,3,5-triazine (yield 5.22 g, yield 91.5%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 1.45 (s, 12H), 7.46-7.66 (m, 12H), 7.80 (dd, J = 8.3Hz, 1.4Hz, 2H), 7.93-7.99 (m, 4H), 8.25 (dd, J = 8.4 Hz, 1.4 Hz, 2H), 8.37-8.39 (m, 3H), 8.84 (dd, J = 7.8Hz, 1.5Hz, 4H), 9.15 (brt, J = 1.9 Hz, 1 H).

Example -18

(4,4-diphenylpyridin-2-yl) -5- (4,4,5,5-tetramethyl- Yl] -1,3,5-triazine (2.00 g, 2.70 mmol), 2-bromopyrimidine (0.52 g, , Tetrakis triphenylphosphine palladium (93.6 mg, 0.081 mmol) and potassium carbonate (1.12 g, 8.10 mmol) were dissolved in a mixed solvent of tetrahydrofuran (64 ml) and water (8 ml) ≪ / RTI > The resulting mixture was stirred at 70 占 폚 for 20 hours. After cooling, water (50 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The obtained solid was purified by silica gel column chromatography (developing solvent: chloroform) and recrystallization (toluene) to obtain the desired product, 4,6-diphenyl-2- [4 '- (4,6- (Yield 0.54 g, yield 28.9%) of 5- (2-pyrimidyl) -biphenyl-3-yl] -1,3,5-triazine (A-73).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.32 (t, J = 5.1Hz, 1H), 7.48-7.66 (m, 13H), 7.81 (brd, J = 7.0Hz, 2H), 7.94 (d, J = 8.4 Hz, 2H), 8.26 (brd, J = 7.3 Hz, 2H), 8.41 (d, J = J = 1.8 Hz, 2H), 8.85-8.88 (m, 4H), 8.96 (d, J = 4.9 Hz, 2H), 9.05 .

The obtained Compound A-73 had a Tg of 133 캜.

Example-19

(4,4-diphenylpyridin-2-yl) -5- (4,4,5,5-tetramethyl- Yl] -1,3,5-triazine (2.00 g, 2.70 mmol), 2-chloropyrazine (0.29 mL, 3.24 2, 4 ', 6'-triisopropylbiphenyl (51.5 mg, 0.11 mmol) and potassium carbonate (1.12 mg, g, 8.10 mmol) was suspended in a mixed solvent of tetrahydrofuran (64 ml) and water (8 ml). The resulting mixture was stirred at 70 占 폚 for 21 hours. After cooling, water (50 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The obtained solid was purified by silica gel column chromatography (developing solvent: chloroform) and recrystallization (toluene) to obtain the desired product, 4,6-diphenyl-2- [4 '- (4,6- Yl) -1,3,5-triazine (A-91) as a white solid (Yield 1.06 g, yield 56.9%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.46-7.68 (m, 12H), 7.80 (dd, J = 8.5Hz, 1.5Hz, 2H), 7.95 (d, J = 1.6Hz, 1H), 8.00 J = 8.5 Hz, 1.3 Hz, 2H), 8.43 (d, J = 8.4 Hz, 2H), 8.64-8.65 (m, 2H), 8.78 (dd, J = (D, J = 8.0 Hz, 2.0 Hz, 4H), 9.20 (t, J = 1.8 Hz, 1H), 9.34 (d, J = 1.3 Hz, 1H), 9.40 t, J = 1.7 Hz, 1H).

The obtained Compound A-91 had a Tg of 124 占 폚.

Synthesis Example -17

(10.0 g, 34.8 mmol), phenacylpyridinium bromide (13.6 g, 48.8 mmol) and ammonium acetate (40.3 g, 522 mmol) were dissolved in a mixture of acetic acid Was dissolved in a mixed solvent of dimethylformamide (100 ml), and the mixture was stirred at 150 占 폚 for 48 hours. After cooling to room temperature, water (300 ml) and methanol (200 ml) were added to the reaction mixture, and the precipitate was collected by filtration. The precipitate obtained by filtration was washed with methanol to obtain an objective off-white powder of the objective 2- (3-bromophenyl) -4,6-diphenylpyridine (yield 11.1 g, yield 97.2%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.35 (brt, J = 8.0Hz, 1H), 7.43-7.57 (m, 7H), 7.73 (brd, J = 8.3Hz, 2H), 7.84 (brs, 1H), 7.90 (brs, 1H), 8.11 (brd, J = 8.0 Hz, 1H), 8.17 (brd, J = 8.1 Hz, 2H), 8.35 (brs, 1H).

Synthesis Example-18

2- (3-bromophenyl) -4,6-diphenylpyridine (5.0 g, 15.3 mmol) obtained in Synthesis Example 17 was dissolved in tetrahydrofuran (20 ml) under an argon stream, Lt; / RTI > 1.55M n-butyllithium / hexane solution (10.9 ml, 16.9 mmol) was slowly added dropwise to the obtained solution, followed by stirring for 1 hour. To the obtained solution, triisopropyl borate (4.60 ml, 19.9 mmol) was slowly added dropwise and stirred for 1 hour. The resulting solution was warmed to room temperature and stirred for 6 hours. Next, 1.5M sodium hydroxide aqueous solution (26.6 mL, 39.9 mmol) was added to the obtained solution and stirred, and then the aqueous layer was removed. The organic layer obtained by the extraction was dried and solidified to obtain 3- (4,6-diphenylpyridin-2-yl) phenylboronic acid as a target intermediate (3.38 g, yield 62.8%).

Example-20

2- (5-Chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (500 mg, 1.19 mmol) obtained in Synthesis Example-10, 3- (4,6-diphenylpyridin-2-yl) phenylboronic acid (502 mg, 1.43 mmol), palladium acetate (5.34 mg, 0.0238 mmol), and 2-dicyclohexylphosphino -2, 4 ', 6'-triisopropylbiphenyl (22.7 mg, 0.0476 mmol) was suspended in tetrahydrofuran (20 ml), and 2M potassium carbonate (1.79 ml, 3.57 mmol) Respectively. The resulting mixture was stirred at 70 占 폚 for 24 hours. After cooling, the mixture was concentrated to dryness, and the resulting solid was washed with water, methanol, and hexane. The resulting solid was recrystallized (toluene) to obtain the objective product, 4,6-diphenyl-2- [3- (4,6-diphenylpyridin-2-yl) -1,1 ': 3' Yl] -1,3,5-triazine (A-241) (yield 800 mg, yield 97.0%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.41-7.61 (m, 15H), 7.69 (t, J = 7.6Hz, 1H), 7.77 (brd, J = 7.0Hz, 2H), 7.82 (brd. J = 7.2 Hz, 2H), 7.87 (brd, J = 7.5 Hz, 1H), 7.94 (d, J = 1.1 Hz, 1H) J = 7.9 Hz, 1H), 8.55 (brs, 1H), 8.80 (dd, J = 8.3 Hz, 1.7 Hz, 4H ), 9.00 (t, J = 1.7 Hz, 1H), 9.06 (t, J = 1.7 Hz, 1H).

Reference Example 1

(1-naphthyl) -6- [4,4 "-bis (2-pyridyl) - [1,1: 3 ' , 1 "] - terphenyl-5 ' -yl] -1,3,5-triazine as a result, the Tg was 104 deg.

Reference Example-2

Diphenyl-1,3,5-triazine (1.50 g, 3.86 mmol), 4- (4,6-diphenylpyridin-2 (1.63 g, 4.64 mmol), tetrakis triphenylphosphine palladium (134 mg, 1.16 mmol) and potassium carbonate (1.60 g, 11.6 mmol) were dissolved in tetrahydrofuran (83 ml) And water (11 ml). The resulting mixture was stirred at 70 占 폚 for 25 hours. After cooling, water (100 ml) was added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane. The resulting solid was recrystallized (toluene) to give the objective product, 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) -Triazine (ETL-2) as an off-white solid (yield 1.79 g, yield 99.2%).

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 7.43-7.64 (m, 12H), 7.68 (t, J = 8.1Hz, 1H), 7.78 (dd, J = 8.5Hz, 1.5Hz, 2H), 7.89 (D, J = 8.6 Hz, 1.4 Hz, 2H), 8.37 (d, J = 8.5 Hz, 2H), 8.77-8.82 (m, 5H), 9.08 (t, J = 1.6 Hz, 1H).

The obtained compound ETL-2 had a Tg of 102 占 폚.

Next, device evaluation will be described.

Structural formulas and abbreviations of the compounds used for device evaluation are shown below.

In addition, all of the above-mentioned compounds were subjected to sublimation purification and used for device evaluation.

Element Reference Example 1-1

On the substrate, a glass substrate with an ITO transparent electrode, in which indium tin oxide (ITO) having a width of 2 mm (thickness: 110 nm) was patterned in a stripe shape was used. The substrate was washed with isopropyl alcohol, and then subjected to surface treatment by ozone ultraviolet cleaning. Vacuum deposition of each layer was carried out on the cleaned substrate by a vacuum vapor deposition method, and an organic electroluminescent device having a light emitting area of 4 mm 2 as shown in Fig. 1 was produced in a sectional view. Each of the organic materials was formed by a resistance heating method.

First, an electric glass substrate was introduced into a vacuum vapor deposition vessel, and the pressure was reduced to 1.0 x 100 <" ⁴ > Pa.

Thereafter, a hole injection layer 2, a charge generation layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 5, and an electron transport layer 6 are formed as an organic compound layer on the ITO transparent electrode- (6), and the cathode layer (7) were laminated in this order.

As the hole injecting layer 2, a sublimed and purified HIL was formed at 65 nm at a rate of 0.15 nm / sec.

As the charge generating layer 3, 5 nm of sublimed and purified HAT was deposited at a rate of 0.05 nm / sec.

As the hole transport layer 4, 10 nm of HTL was formed at a rate of 0.15 nm / sec.

As the light emitting layer 5, 25 nm of EML-1 and EML-2 were formed in a ratio of 95: 5 (film formation rate: 0.18 nm / second).

As the electron transport layer 6, 2- [5- (9-phenanthryl) -4 '- (2-pyrimidyl) biphenyl- 6-diphenyl-1,3,5-triazine (ETL-1) and Liq in a ratio of 50: 50 (weight ratio) were formed at a film thickness of 30 nm (film formation rate: 0.15 nm / sec).

Finally, a metal mask was disposed so as to be in direct contact with the ITO stripe, and the cathode layer 7 was formed. The cathode layer 7 was formed into a film of 80 nm (film formation rate 0.5 nm / sec) and 20 nm (film formation rate 0.2 nm / sec) respectively in this order of silver / magnesium Layer structure.

Each film thickness was measured with a stylus type film thickness meter (DEKTAK).

The device was also sealed in a nitrogen atmosphere glove box with oxygen and moisture concentration of 1 ppm or less. As the sealing, a sealing cap made of glass and an epoxy type ultraviolet curing resin (manufactured by Nagase Chemtech Co., Ltd.) were used.

A direct current was applied to the thus fabricated organic electroluminescent device and the luminescent characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON Corporation. The voltage (V) and the current efficiency (cd / A) at the time when the current density was 10 mA / cm 2 were measured as the light emitting characteristics and the device lifetime (h) at the time of continuous lighting was measured. The device lifetime h in Table 1 was obtained by measuring the luminance decay time during continuous lighting when the manufactured device was driven at an initial luminance of 800 cd / m 2 and when the luminance (cd / m 2) was reduced by 20% And the time required for the measurement was measured. The device lifetime was defined as a reference value (100) for the lifetime (h) of the device in Reference Example 1-1 of this device. The results are shown in Table 1.

Element Reference Example 1-2

In the same manner as in Reference Example 1-1 except that 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) -biphenyl -3-yl] -1,3,5-triazine (ETL-2) was used as the organic EL device, and an organic EL device was prepared and evaluated. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Example 1-1

In the same manner as in Example 1-1 except that 4,6-diphenyl-2- [4- (4,6-diphenylpyridin-2-yl) -4 " (Compound A-127) was used in place of (2-pyridyl) -1,1 ': 3', 1 '' - terphenyl-5'- 1, an organic electroluminescent device was fabricated and evaluated. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Example 1-2

In the same manner as in Example 1-1 except that 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) An organic electroluminescent device was prepared in the same manner as in Reference Example 1-1 except that (3-pyridyl) -biphenyl-3-yl] -1,3,5-triazine (Compound A-37) , Respectively. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Embodiment 1-3

In the element reference example 1-1, 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) -5- An organic electroluminescent device was fabricated in the same manner as in Reference Example 1-1 except for using (9-phenanthryl) -biphenyl-3-yl] -1,3,5-triazine (Compound A-165) , Respectively. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Embodiments 1-4

In the device Reference Example 1-1, the same procedure as in Example 1 was repeated except that 4,6-diphenyl-2- [4- (4,6-diphenylpyridin-2-yl) -1,1 Except that an organic electroluminescent device was used in the same manner as in Reference Example 1-1 except that the organic electroluminescent device was used, except that the organic electroluminescent device was used in place of the organic electroluminescent device ': 3', 1 "-terphenyl-5'-yl] -1,3,5-triazine (Compound A- The results are shown in Table 1. The lifetime of the device is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1.

Device Embodiments 1-5

In the same manner as in Example 1-1 except that 4,6-diphenyl-2- [4- (4,6-diphenylpyridin-2-yl) -1,1 (Compound A-109) were used in the same manner as in Reference Example 1-1 except that 1 ': 3', 1 ": 4", 1 "'-tetraphenyl-5'-yl] -1,3,5- The results are shown in Table 1. The device lifetime was measured by measuring the lifetime (h) of the device and setting the lifetime of the device in Reference Example 1-1 to 100 As a relative value.

Device Example 1-6

In the same manner as in Example 1-1 except that 4,6-diphenyl-2- [4- (2,6-diphenylpyridin-4-yl) -4 " (Compound A-136) was used in place of (2-pyridyl) -1,1 ': 3', 1 '' - terphenyl-5'- 1, an organic electroluminescent device was fabricated and evaluated. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Example 1-7

In the same manner as in Example 1-1 except that 4,6-diphenyl-2- [4- (4,6-diphenylpyridin-2-yl) -4 " (Compound A-145) was used in place of 1- (3-pyridyl) -1,1 ': 3', 1 '' - terphenyl-5'- 1, an organic electroluminescent device was fabricated and evaluated. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Examples 1-8

In the same manner as in Example 1-1, except that 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) (Compound A-164) was used in place of the compound (A-164) used in Reference Example 1-1, an organic electroluminescent device was prepared , Respectively. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Example 1-9

In the same manner as in Example 1-1 except that 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) -5- (Compound A-163) was used in place of the compound (A-163) used in Reference Example 1-1, an organic electroluminescent device was prepared , Respectively. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Embodiment 1-10

In the device Reference Example 1-1, the same procedure as in Example 1-1 was repeated except that 4,6-diphenyl-2- [4- (2,6-diphenylpyridin-4-yl) (Compound A-118) was obtained in the same manner as in Reference Example 1-1, except that 1 ': 3', 1 ": 4" The results are shown in Table 1. The device lifetime was measured by measuring the lifetime (h) of the device and setting the lifetime of the device in Reference Example 1-1 to 100 As a relative value.

Device Example 1-11

In the same manner as in Example 1-1, except that 4,6-diphenyl-2- [4 '- (2,6-diphenylpyridin-4-yl) (Compound A-225) was used in place of the compound (A-225) used in Reference Example 1-1 except for using 2-phenyl-2- The device was fabricated and evaluated. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Example 1-12

In the same manner as in Reference Example 1-1 except that ETL-1 was used instead of 4,6-diphenyl-2- [4 '- (2,4-diphenylpyridin-6-yl) (Compound A-226) was used in place of the compound (A-226) used in Reference Example 1-1, the organic electroluminescence The device was fabricated and evaluated. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Example 1-13

In the same manner as in Example 1-1 except that 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2-yl) (Compound A-73) was used in place of the compound (A-73) used in Reference Example 1-1, an organic electroluminescent device was prepared , Respectively. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Device Example 1-14

In the same manner as in Reference Example 1-1 except that ETL-1 was replaced with 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridin-2- (Compound A-91) was used in place of the compound (A-91) used in Reference Example 1-1, an organic electroluminescent device was prepared , Respectively. The results are shown in Table 1. The device lifetime is represented by a relative value obtained by measuring the lifetime (h) of the device and the lifetime of the device in Reference Example 1-1 from 100.

Element Reference Example 2-1

An organic electroluminescent device was fabricated and evaluated in the same manner as in Reference Example 1-1 except that the electron transport layer 6 was made to have a thickness of 30 nm using only ETL-1 in Reference Example 1-1 . The results are shown in Table 2.

The device lifetime h in Table 2 was obtained by measuring the luminance decay time at the time of continuous lighting when the manufactured device was driven at an initial luminance of 800 cd / m 2, and until the luminance (cd / m 2) The time spent was measured. The device life span was the reference value (100) as the device lifetime (h) in Reference Example 2-1 of this device.

Device Embodiment 2-1

In the same manner as in Reference Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4- (4,6-diphenylpyridine- Yl) -1,3,5-triazine (Compound A-127) was reacted with (2-pyridyl) An organic electroluminescent device was fabricated and evaluated in the same manner as in Reference Example 2-1. The results are shown in Table 2.

Device Example 2-2

In the same manner as in Reference Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridine 2-yl) -5- (3-pyridyl) -biphenyl-3-yl] -1,3,5-triazine (Compound A-37) , An organic electroluminescent device was fabricated and evaluated. The results are shown in Table 2.

Device Embodiment 2-3

In the same manner as in Reference Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4- (4,6-diphenylpyridine- 2-yl) -1,1 ': 3', 1 "-terphenyl-5'-yl] -1,3,5-triazine (Compound A- An organic electroluminescent device was fabricated and evaluated in the same manner. The results are shown in Table 2.

Device Example 2-4

In the same manner as in Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4- (4,6-diphenylpyridine- (Compound A-109) was used instead of 2-amino-2-thiophene-2-yl) -1,1 ': 3', 1 " An organic electroluminescent device was fabricated and evaluated in the same manner as in Reference Example 2-1. The results are shown in Table 2.

Device Example 2-5

In the same manner as in Reference Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4- (2,6-diphenylpyridine- Yl) -1,3,5-triazine (Compound A-136) was reacted with 4-chloro- An organic electroluminescent device was fabricated and evaluated in the same manner as in Reference Example 2-1. The results are shown in Table 2.

Device Example 2-6

In the same manner as in Reference Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4- (4,6-diphenylpyridine- Yl) -1,3,5-triazine (Compound A-145) was reacted with 4-chloro- An organic electroluminescent device was fabricated and evaluated in the same manner as in Reference Example 2-1. The results are shown in Table 2.

Device Example 2-7

In the same manner as in Reference Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridine 2-yl) -5- (2-naphthyl) -biphenyl-3-yl] -1,3,5-triazine (Compound A-164) , An organic electroluminescent device was fabricated and evaluated. The results are shown in Table 2.

Device Example 2-8

In the same manner as in Reference Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridine 2-yl) -5- (1-naphthyl) -biphenyl-3-yl] -1,3,5-triazine (Compound A-163) , An organic electroluminescent device was fabricated and evaluated. The results are shown in Table 2.

Device Example 2-9

In the same manner as in Reference Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4- (2,6-diphenylpyridine- 4-yl) -1,1 ': 3', 1 ": 4", 1 "'-tetraphenyl-5'- yl] -1,3,5- triazine (Compound A- An organic electroluminescent device was fabricated and evaluated in the same manner as in Reference Example 2-1. The results are shown in Table 2.

Device Example 2-10

In the same manner as in Reference Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4 '- (2,6-diphenylpyridine (Compound A-225) was used in place of 2- (4-fluorophenyl) -5- 1, an organic electroluminescent device was fabricated and evaluated. The results are shown in Table 2.

Element Embodiments 2-11

In the same manner as in Reference Reference Example 2-1, except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4 '- (2,4-diphenylpyridine (Compound A-226) was used in place of 2- (2-phenylpyridin-5-yl) 1, an organic electroluminescent device was fabricated and evaluated. The results are shown in Table 2.

Device Examples 2-12

In the same manner as in Reference Reference Example 2-1 except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridine 2-yl) -5- (2-pyrimidyl) -biphenyl-3-yl] -1,3,5-triazine (Compound A-73) , An organic electroluminescent device was fabricated and evaluated. The results are shown in Table 2.

Device Example 2-13

In the same manner as in Reference Reference Example 2-1 except that ETL-1 used in the electron transport layer 6 was replaced with 4,6-diphenyl-2- [4 '- (4,6-diphenylpyridine Yl] -1,3,5-triazine (Compound A-91) was used in place of 2- , An organic electroluminescent device was fabricated and evaluated. The results are shown in Table 2.

While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.

The contents of the specification, claims, drawings and summary of Japanese Patent Application No. 2014-32254 filed on February 21, 2014 and Japanese Patent Application No. 2014-264073 filed on December 26, 2014 are hereby incorporated by reference herein. Quot ;, which is incorporated herein by reference in its entirety.

The triazine compound (1) of the present invention is excellent in heat resistance and can provide an organic electroluminescent device excellent in longevity and luminescence efficiency by using the compound.

In addition, the triazine compound (1) of the present invention is used as an electron transporting material for an organic electroluminescence device having a low driving voltage. Further, according to the present invention, an organic electroluminescent device having excellent power consumption can be provided.

In addition, the triazine compound of the present invention has a good thermal stability at the time of sublimation purification, so that it is possible to provide a material which is excellent in operability of a sublimation purification and has few impurities that cause element deterioration of the organic electroluminescence device. In addition, the triazine compound of the present invention is excellent in stability of a vapor deposition film, and thus can provide an organic electroluminescent device with a long life.

Further, the thin film made of the triazine compound (1) of the present invention is excellent as an electron transporting ability, a hole blocking ability, an oxidation-reduction resistance, a water resistance, an acid firing and an electron injection property, , Particularly, an electron transporting material, a hole blocking material, a light emitting host material, and the like. Further, since the triazine compound (1) of the present invention is a wide band gap compound, it can be suitably used for a conventional phosphorescent device as well as a conventional phosphorescent device.

The compound represented by the general formula (5) or (9) and the method for producing the triazine compound represented by the general formula (1) using the triazine compound represented by the general formula (1) In order to efficiently provide the information to the user.

1: Glass substrate with ITO transparent electrode
2: Hole injection layer
3: charge generation layer
4: hole transport layer
5: light emitting layer
6: electron transport layer
7: cathode layer

Claims (21)

A triazine compound represented by the following general formula (1):

In the general formula (1)
Two Ar ^{4 s} are the same and represent a hydrogen atom, a fluorine atom, a methyl group, a methoxy group or a phenyl group;
Ar ¹ and Ar ² each independently represent a monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms which is composed of a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms or a 6-membered ring, , A fluorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, or a pyridyl group;
Ar ³ represents a monocyclic, fused or cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms (the group may be substituted by a fluorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, or a pyridyl group) A monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms (the group is selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a pyridyl group, a phenyl group, a naphthyl group, Which may be optionally substituted;
Provided that either one of Z ¹ and Z ² represents a nitrogen atom and the other represents CH. The triazine compound according to claim 1, which is represented by the general formula (1) 'or (1) ":

Among the general formulas (1) 'and (1)',
Two Ar ⁴ are identical, and means the same as Claim 1 and;
Ar ¹ , Ar ² , Ar ³ , Z ¹ and Z ² have the same meanings as in claim 1. 3. The triazine compound according to claim 1 or 2, wherein Ar < ⁴ > is a phenyl group, a methyl group or a hydrogen atom. 3. The triazine compound according to claim 1 or 2, wherein Ar < ⁴ > is a hydrogen atom. The compound according to Claim 1 or 2, wherein Ar ¹ and Ar ² each independently represent a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms (the group includes a fluorine atom, an alkyl group having 1 to 4 carbon atoms, Or an alkoxy group of 1 to 4 carbon atoms, a phenyl group, or a pyridyl group). 3. The compound according to claim 1 or 2, wherein Ar ¹ and Ar ² each independently represent a phenyl group, a naphthyl group or a phenanthryl group (these groups may be substituted with a fluorine atom, a methyl group, a phenyl group or a pyridyl group) Triazine compound. 3. The triazine compound according to claim 1 or 2, wherein Ar ¹ and Ar ² are each independently a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group. 3. The triazine compound according to claim 1 or 2, wherein Ar < ^{1 >} and Ar < ² > ^3. The compound according to claim 1 or 2, wherein Ar ³ is a C3-C18 monocyclic, bicyclic or tricyclic aromatic hydrocarbon group (said group may be substituted with a phenyl group or a pyridyl group) Triazine ring or thiazole ring-containing nitrogen-containing aromatic hydrocarbon group (said group may be substituted with a phenyl group, a biphenyl group or a naphthyl group). ^3. The compound according to claim 1 or 2, wherein Ar ³ is a phenyl group, a naphthyl group or a biphenyl group (these groups may be substituted with a phenyl group or a pyridyl group), a monocyclic or a condensed ring nitrogenous aromatic hydrocarbon group having 3 to 9 carbon atoms And the corresponding group may be substituted with a phenyl group, a biphenyl group or a naphthyl group). The compound according to Claim 1 or 2, wherein Ar ³ is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridylphenyl group, a pyridyl group, a pyrazyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, Wherein the triazine compound is a thiazine compound, wherein the triazine compound is a thiazine compound, a thiadiazole compound, a thiadiazole compound, a thiophene compound, a thiadiazole compound, ^3. The triazine compound according to claim 1 or 2, wherein Ar ³ is phenyl, biphenyl, naphthyl, pyridyl, phenylpyridyl, pyrazyl, pyrimidyl, quinolyl or isoquinolyl. A process for producing a triazine compound according to claim 1,
A process for the preparation of a compound represented by the general formula (2) below, a compound represented by the following general formula (3) and a general formula (4) in the presence of a base or in the absence of a base in the presence of a palladium catalyst, And at the same time a coupling reaction is carried out.

Of the general formulas (1), (2), (3) and (4)
Two Ar ⁴ are identical, and means the same as Claim 1 and;
Ar ¹ , Ar ² , Ar ³ , Z ¹ and Z ² have the same meanings as in claim 1;
Y ¹ and Y ² each independently represent a leaving group;
M ¹ and M ² each independently represent ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ ;
However, R ¹ and R ² are, each independently, a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group or a phenyl group of 4 from having 1, R ⁴ is a 4-from a hydrogen atom, a C 1 An alkyl group or a phenyl group, two R ^{4 s} of B (OR ⁴ ) ₂ may be the same or different and two R ^{4 s} may be integral to form a ring including an oxygen atom and a boron atom. A process for producing a triazine compound according to claim 1,
Characterized in that the compound represented by the following general formula (5) and the compound represented by the following general formula (6) are subjected to a coupling reaction in the presence of a base or in the absence of a base in the presence of a palladium catalyst. Method of preparing triazine compound:

Of the general formulas (1), (5) and (6)
Two Ar ⁴ are identical, and means the same as Claim 1 and;
Ar ¹ , Ar ² , Ar ³ , Z ¹ and Z ² have the same meanings as in claim 1;
Y ³ represents a leaving group;
M ³ represents ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ ;
R ¹ and R ² each independently represent a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, R ⁴ represents a hydrogen atom, , Two R ⁴ groups of B (OR ⁴ ) ₂ may be the same or different and two R ⁴ groups may be combined to form a ring including an oxygen atom and a boron atom . A process for producing a triazine compound according to claim 1,
A process for producing a compound represented by the following general formula (7) and a compound represented by the following general formula (8) in the presence of a base or in the absence of a base in the presence of a palladium catalyst, Method of preparing triazine compound:

Among the general formulas (1), (7) and (8)
Two Ar ⁴ are identical, and means the same as Claim 1 and;
Ar ¹ , Ar ² , Ar ³ , Z ¹ and Z ² have the same meanings as in claim 1;
M ⁴ represents ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ ;
However, R ¹ and R ² are, each independently, a chlorine atom, a bromine atom or an iodine atom, R ³ is, shows a 4 alkyl group or a phenyl group from C 1, R ⁴ is 4 from a hydrogen atom, a C 1 , Two R ⁴ groups of B (OR ⁴ ) ₂ may be the same or different and two R ⁴ groups may be combined to form a ring including an oxygen atom and a boron atom ;
Y ⁴ represents a leaving group. 16. The process for producing a triazine compound according to any one of claims 13 to 15, wherein the palladium catalyst is a palladium catalyst having a tertiary phosphine as a ligand. 16. The process according to any one of claims 13 to 15, wherein the palladium catalyst is selected from the group consisting of palladium (II) palladium (II) having triphenylphosphine or 2-dicyclohexylphosphino-2 ', 4', 6'- triisopropylbiphenyl as ligands Wherein the catalyst is a triazine compound. A compound represented by the following general formula (9):

In the general formula (9)
Two Ar ⁴ are the same and represent a hydrogen atom, a fluorine atom, a methyl group, a methoxy group or a phenyl group;
Ar ¹ and Ar ² each independently represent a monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms which is composed of a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms or a 6-membered ring, , A fluorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, or a pyridyl group;
Provided that either one of Z ¹ and Z ² represents a nitrogen atom and the other represents CH;
Y ² represents a leaving group. The compound according to claim 14 represented by the following formula (5):

In the general formula (5)
Two Ar ⁴ are the same and represent a hydrogen atom, a fluorine atom, a methyl group, a methoxy group or a phenyl group;
Ar ¹ and Ar ² each independently represent a monocyclic or a cyclic nitrogen-containing aromatic hydrocarbon group having 3 to 13 carbon atoms which is composed of a monocyclic, a linking or a cyclic aromatic hydrocarbon group having 6 to 18 carbon atoms or a 6-membered ring (these groups are fluorine, An alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, or a pyridyl group);
Provided that either one of Z ¹ and Z ² represents a nitrogen atom and the other represents CH;
M ³ represents ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ ;
R ¹ and R ² each independently represent a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, R ⁴ represents a hydrogen atom, , And two R ⁴ groups of B (OR ⁴ ) ₂ may be the same or different. The two R ⁴ may be monosubstituted to form a ring including an oxygen atom and a boron atom. An organic electroluminescent device comprising the triazine compound according to claim 1. 21. The organic electroluminescent device according to claim 20, wherein the electron transport layer contains a triazine compound.

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