Pyridine Compounds

Abstract

To provide a pyridine compound having a high crystallization temperature that contributes to formation of an organic electroluminescent element exhibiting characteristics of a long life, luminous efficiency and drive voltage at high levels and to provide a material for an organic electroluminescent element, an electron transport material for an organic electroluminescent element and an organic electroluminescent element each including the pyridine compound.SOLUTION: A pyridine compound has a specific partial structure represented by a formula (Q-1), (Q-2) or (Q-3) and a 1,3,5-triazyl group.SELECTED DRAWING: Figure 2

Description

[Technical field]

[0001] The present invention relates to a pyridine compound, a material for an organic electroluminescent device, an electron transport material for an organic electroluminescent device, and an organic electroluminescent device. [Background technology]

[0002] Organic electroluminescent devices have started to be put to practical use, mainly for small mobile applications. However, to further expand their applications, performance improvement is essential, and materials with low driving voltage, high luminous efficiency, and long life characteristics are required. In addition, materials used in organic electroluminescent devices often have a problem with crystallization when made into thin films, so materials with high crystallization temperatures are required. Patent Document 1 discloses a pyridine compound having 1,3,5-triazine as a partial structure, which is a material for an organic electroluminescent device having a long life and excellent luminescent properties. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2007-314503 A Summary of the Invention [Problem to be solved by the invention]

[0004] In order to expand the applications and the environments in which the device can be used, it is necessary to improve three characteristics, i.e., driving voltage, luminous efficiency, and life characteristics. However, the pyridine compound disclosed in Patent Document 1 does not sufficiently satisfy these requirements, and there is a demand for a compound that achieves the above three characteristics at an even higher level.

[0005] Therefore, one aspect of the present invention is directed to providing a pyridine compound having a high crystallization temperature that contributes to the formation of an organic electroluminescent device exhibiting high levels of driving voltage characteristics, long life characteristics, and luminous efficiency characteristics, as well as a material for an organic electroluminescent device containing the pyridine compound and an electron transport material for an organic electroluminescent device. Furthermore, still another aspect of the present invention is directed to providing an organic electroluminescent device that has a low driving voltage, high luminous efficiency, and long life characteristics, and can be used in various applications or under various environments. [Means for solving the problem]

[0006] A pyridine compound according to one embodiment of the present invention is a pyridine compound having a partial structure represented by formula (Q-1), (Q-2) or (Q-3) and a 1,3,5-triazyl group:

[0007] [ka]

[0008] During the ceremony, L 1 and L 2 are each independently Single bond, A divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or represents a divalent heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element; Ar 1 and Ar 2 are each independently Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms, composed of C, H and a Group 16 element; L 1 When is a single bond, Ar 1 is an aromatic hydrocarbon group having 6 to 18 carbon atoms; L 2 When is a single bond, Ar 2is an aromatic hydrocarbon group having 6 to 18 carbon atoms; X 1 , X 2 and X 3 one of which is a nitrogen atom and the others are CH; X 4 , X 5 and X 6 one of which is a nitrogen atom and the others are CH; X 7 , X 8 and X 9 one of which is a nitrogen atom and the others are CH; X 4 and X 5 one of which is a nitrogen atom and the others are CH; L 1 , L 2 , Ar 1 , Ar 2 may each independently be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

[0009] A pyridine compound according to one embodiment of the present invention is a pyridine compound represented by formula (1):

[0010] [ka]

[0011] During the ceremony, Ar 3 teeth, Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms, composed of C, H and a Group 16 element; Ar 4 teeth, Hydrogen atom, Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms, composed of C, H and a Group 16 element; L 3 teeth, Single bond, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, A divalent heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings and consisting of C, H and N, or represents a divalent heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element; L 4 represents a trivalent or tetravalent aromatic hydrocarbon group having 6 to 18 carbon atoms; a represents 0, 1 or 2: b stands for 1, 2 or 3: a+b is 3; n represents 1 or 2; When n is 2, two L 4 and Ar 4 may be different from each other; m represents 1 or 2; When m is 2, two Q's may be different from each other; When a is 2, two Ar 3 may be different from each other; When b is 2 or more, multiple L 3 , L 4 , Ar 4 , Q, m and n may be different from each other; Q is a substituent represented by formula (Q-1), (Q-2) or (Q-3):

[0012] [ka]

[0013] During the ceremony, L 1 and L 2 are each independently Single bond, A divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or represents a divalent heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element; Ar 1 and Ar 2 are each independently Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms, composed of C, H and a Group 16 element; L 1 When is a single bond, Ar 1 is an aromatic hydrocarbon group having 6 to 18 carbon atoms; L 2 When is a single bond, Ar 2 is an aromatic hydrocarbon group having 6 to 18 carbon atoms; X 1 , X 2 and X 3 one of which is a nitrogen atom and the others are CH; X 4 , X 5 and X 6 one of which is a nitrogen atom and the others are CH; X 7 , X 8 and X 9 one of which is a nitrogen atom and the others are CH; L 1 , L 2 , L 3 , L 4 , Ar 1 , Ar 2 , Ar 3 and Ar 4 may each independently be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

[0014] A material for an organic electroluminescent device according to another embodiment of the present invention contains the above pyridine compound.

[0015] An organic electroluminescent device according to still another embodiment of the present invention contains the above pyridine compound. Effect of the Invention

[0016] According to one aspect of the present invention, it is possible to provide a pyridine compound having a high crystallization temperature that contributes to the formation of an organic electroluminescent device exhibiting high levels of driving voltage characteristics, luminous efficiency characteristics, and long life characteristics. According to another aspect of the present invention, it is possible to provide a material for an organic electroluminescent device containing the pyridine compound, and an electron transport material for an organic electroluminescent device. Furthermore, according to yet another aspect of the present invention, it is possible to provide an organic electroluminescent device that exhibits low driving voltage, high luminous efficiency, and long life characteristics and can be used for various applications. [Brief description of the drawings]

[0017] [Figure 1] 1 is a schematic cross-sectional view showing an example of a layered configuration of an organic electroluminescent device according to one embodiment of the present disclosure. [Diagram 2] FIG. 2 is a schematic cross-sectional view showing another example of a laminate configuration of an organic electroluminescent device according to an embodiment of the present disclosure (configuration of device example 1). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0018] The pyridine compounds according to each aspect of the present invention will be described in detail below.

[0019] A pyridine compound according to one embodiment of the present invention is a pyridine compound having a partial structure represented by formula (Q-1), (Q-2) or (Q-3) and a 1,3,5-triazyl group:

[0020] [ka]

[0021] During the ceremony, L 1 and L 2 are each independently Single bond, A divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or represents a divalent heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element; Ar 1 and Ar 2 are each independently Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms, composed of C, H and a Group 16 element; L 1 When is a single bond, Ar 1 is an aromatic hydrocarbon group having 6 to 18 carbon atoms; L 2 When is a single bond, Ar 2 is an aromatic hydrocarbon group having 6 to 18 carbon atoms; X 1 , X 2 and X 3 one of which is a nitrogen atom and the others are CH; X 4 , X 5 and X 6 one of which is a nitrogen atom and the others are CH; X 7 , X 8 and X 9 one of which is a nitrogen atom and the others are CH; L 1 , L 2 , Ar 1 , Ar 2 may each independently be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

[0022] Further, a pyridine compound according to another embodiment of the present invention is a pyridine compound represented by formula (1):

[0023] [ka]

[0024] During the ceremony, Ar 3 teeth, Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms, composed of C, H and a Group 16 element; Ar 4 teeth, Hydrogen atoms, Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms, composed of C, H and a Group 16 element; L 3 teeth, Single bond, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, A divalent heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings and consisting of C, H and N, or represents a divalent heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element; L 4 represents a trivalent or tetravalent aromatic hydrocarbon group having 6 to 18 carbon atoms; a represents 0, 1 or 2: b stands for 1, 2 or 3: a+b is 3; n represents 1 or 2; When n is 2, two L 4 and Ar 4 may be different from each other; m represents 1 or 2; When m is 2, two Q's may be different from each other; When a is 2, two Ar 3 may be different from each other; When b is 2 or more, multiple L 3 , L 4 , Ar 4, Q, m and n may be different from each other; Q is a substituent represented by formula (Q-1), (Q-2) or (Q-3):

[0025] [ka]

[0026] During the ceremony, L 1 and L 2 are each independently Single bond, A divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or represents a divalent heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element; Ar 1 and Ar 2 are each independently Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms, composed of C, H and a Group 16 element; L 1 When is a single bond, Ar 1 is an aromatic hydrocarbon group having 6 to 18 carbon atoms; L 2 When is a single bond, Ar 2 is an aromatic hydrocarbon group having 6 to 18 carbon atoms; X 1 , X 2 and X 3 one of which is a nitrogen atom and the others are CH; X 4 , X 5 and X 6 one of which is a nitrogen atom and the others are CH; X 7 , X 8 and X 9 one of which is a nitrogen atom and the others are CH; L 1 , L 2 , L3 , L 4 , Ar 1 , Ar 2 , Ar 3 and Ar 4 may each independently be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

[0027] The definitions of the substituents in the formulae (1), (Q-1), (Q-2) and (Q-3) and their preferred specific examples are as follows: In the following, the pyridine compound having the partial structure represented by the formula (Q-1), (Q-2) or (Q-3) and a 1,3,5-triazyl group, and the pyridine compound represented by the formula (1) may be collectively referred to as the pyridine compound (Q).

[0028] [Ar 1 and Ar 2 About Ar 1 and Ar 2 are each independently Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms, composed of C, H and a Group 16 element; Ar 1 and Ar 2 may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

[0029] In addition, 1 When is a single bond, Ar 1 is an aromatic hydrocarbon group having 6 to 18 carbon atoms. 2 When is a single bond, Ar 2 is an aromatic hydrocarbon group having 6 to 18 carbon atoms.

[0030] The pyridine compound (Q) has excellent electron transporting properties, and therefore is 1 and Ar 2 are each preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group. In terms of ease of synthesis, a phenyl group, a biphenylyl group, a naphthyl group, or a pyridylphenyl group is more preferable.

[0031] Ar 1 and Ar 2Examples of the aryl groups include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 3,5-dimethylphenyl group, a 2-(1-naphthyl)phenyl group, a 3-(1-naphthyl)phenyl group, a 4-(1-naphthyl)phenyl group, a 2-(2-naphthyl)phenyl group, a 3-(2-naphthyl)phenyl group, a 4-(2-naphthyl)phenyl group, a 2-cyanophenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, a 3,5-dicyanophenyl group, nophenyl group, 1-phenanthrenyl group, 2-phenanthrenyl group, 3-phenanthrenyl group, 4-phenanthrenyl group, 9-phenanthrenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9-fluorenyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 9,9-dimethylfluoren-1-yl group, 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, 1-triphenylenyl group, 2-triphenylenyl group, 1- pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 2-pyrazyl group, 6-methylpyridin-2-yl group, 3-methylpyridin-2-yl group, 4-methylpyridin-2-yl group, 5-methylpyridin-2-yl group, 2-methylpyridin-3-yl group, 4-methylpyridin-3-yl group, 5-methylpyridin-3-yl group, 6-methylpyridin-3-yl group, 2-methylpyridin-4-yl group, 3-methylpyridin-4-yl group, 2,6-dimethylpyridin-3-yl group, 2,4-dimethylpyridin-3-yl group, 2,5-dimethylpyridin-3-yl group, 6-phenylpyridin-2-yl group, 3-phenylpyridin-2-yl group, 4-phenylpyridin-2-yl group, 5-phenylpyridin-2-yl group, 2-phenylpyridin-3-yl group, 4-phenylpyridin-3-yl group, 5-phenylpyridin-3-yl group, 6-phenylpyridin-3-yl group, 2-phenylpyridin-4-yl group, 3-phenylpyridin-4-yl group, 2-quinolyl group,3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinazolyl group, 4-quinazolyl group, 5-quinazolyl group, 6-quinazolyl group, 7-quinazolyl group, 8-quinazolyl group, benzo[h]quinolin-2-yl group, benzo[h]quinolin-3-yl group, benzo[h]quinolin-4-yl group, benzo[h]quinolin-5-yl group, benzo[h]quinolin-2-yl group, ]quinolin-6-yl group, benzo[h]quinolin-7-yl group, benzo[h]quinolin-8-yl group, benzo[h]quinolin-9-yl group, benzo[h]quinolin-10-yl group, phenanthridin-1-yl group, benzo[c]quinolin-2-yl group, benzo[c]quinolin-3-yl group, benzo[c]quinolin-4-yl group, benzo[c]quinolin-6-yl group, benzo[c]quinolin-7-yl group, benzo[c]quinolin-8-yl group, benzo[c]quinolin-9-yl group, benzo[c]quinolin-10-yl group, benzo[f]quinolin-1- yl group, benzo[f]quinolin-2-yl group, benzo[f]quinolin-3-yl group, benzo[f]quinolin-5-yl group, benzo[f]quinolin-6-yl group, benzo[f]quinolin-7-yl group, benzo[f]quinolin-8-yl group, benzo[f]quinolin-9-yl group, benzo[f]quinolin-10-yl group, acridine-1-yl group, acridine-2-yl group, acridine-3-yl group, acridine-4-yl group, acridine-9-yl group, phenazin-1-yl group, phenazin-2-yl group, azatriphenylenyl group, azapyrenyl group, diphenyl ether group, azatriphenylenyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 2-benzothiophenyl group, 3-benzothiophenyl group, 4-benzothiophenyl group, 5-benzothiophenyl group, 6-benzothiophenyl group, 7-benzothiophenyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group,4-dibenzothiophenyl group, etc.

[0032] [Ar 3 About Ar 3 teeth, Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or It represents a heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element. Ar 3 may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

[0033] The pyridine compound (Q) has excellent electron transporting properties, and therefore is 3 is preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group. In terms of ease of synthesis, a phenyl group or a biphenylyl group is more preferred.

[0034] Ar 3Examples of the aryl groups include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 3,5-dimethylphenyl group, a 2-(1-naphthyl)phenyl group, a 3-(1-naphthyl)phenyl group, a 4-(1-naphthyl)phenyl group, a 2-(2-naphthyl)phenyl group, a 3-(2-naphthyl)phenyl group, a 4-(2-naphthyl)phenyl group, a 2-cyanophenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, a 3,5-dicyanophenyl group, nophenyl group, 1-phenanthrenyl group, 2-phenanthrenyl group, 3-phenanthrenyl group, 4-phenanthrenyl group, 9-phenanthrenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9-fluorenyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 9,9-dimethylfluoren-1-yl group, 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, 1-triphenylenyl group, 2-triphenylenyl group, 1- pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 2-pyrazyl group, 6-methylpyridin-2-yl group, 3-methylpyridin-2-yl group, 4-methylpyridin-2-yl group, 5-methylpyridin-2-yl group, 2-methylpyridin-3-yl group, 4-methylpyridin-3-yl group, 5-methylpyridin-3-yl group, 6-methylpyridin-3-yl group, 2-methylpyridin-4-yl group, 3-methylpyridin-4-yl group, 2,6-dimethylpyridin-3-yl group, 2,4-dimethylpyridin-3-yl group, 2,5-dimethylpyridin-3-yl group, 6-phenylpyridin-2-yl group, 3-phenylpyridin-2-yl group, 4-phenylpyridin-2-yl group, 5-phenylpyridin-2-yl group, 2-phenylpyridin-3-yl group, 4-phenylpyridin-3-yl group, 5-phenylpyridin-3-yl group, 6-phenylpyridin-3-yl group, 2-phenylpyridin-4-yl group, 3-phenylpyridin-4-yl group, 2-quinolyl group,3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinazolyl group, 4-quinazolyl group, 5-quinazolyl group, 6-quinazolyl group, 7-quinazolyl group, 8-quinazolyl group, benzo[h]quinolin-2-yl group, benzo[h]quinolin-3-yl group, benzo[h]quinolin-4-yl group, benzo[h]quinolin-5-yl group, benzo[h]quinolin-2-yl group, ]quinolin-6-yl group, benzo[h]quinolin-7-yl group, benzo[h]quinolin-8-yl group, benzo[h]quinolin-9-yl group, benzo[h]quinolin-10-yl group, phenanthridin-1-yl group, benzo[c]quinolin-2-yl group, benzo[c]quinolin-3-yl group, benzo[c]quinolin-4-yl group, benzo[c]quinolin-6-yl group, benzo[c]quinolin-7-yl group, benzo[c]quinolin-8-yl group, benzo[c]quinolin-9-yl group, benzo[c]quinolin-10-yl group, benzo[f]quinolin-1- yl group, benzo[f]quinolin-2-yl group, benzo[f]quinolin-3-yl group, benzo[f]quinolin-5-yl group, benzo[f]quinolin-6-yl group, benzo[f]quinolin-7-yl group, benzo[f]quinolin-8-yl group, benzo[f]quinolin-9-yl group, benzo[f]quinolin-10-yl group, acridine-1-yl group, acridine-2-yl group, acridine-3-yl group, acridine-4-yl group, acridine-9-yl group, phenazin-1-yl group, phenazin-2-yl group, azatriphenylenyl group, azapyrenyl group, diphenyl ether group, azatriphenylenyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 2-benzothiophenyl group, 3-benzothiophenyl group, 4-benzothiophenyl group, 5-benzothiophenyl group, 6-benzothiophenyl group, 7-benzothiophenyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group,4-dibenzothiophenyl group, etc.

[0035] [Ar 4 About Ar 4 teeth, Hydrogen atom, Aromatic hydrocarbon groups having 6 to 18 carbon atoms, A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, consisting of C, H and N, or It represents a heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element. Ar 4 may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

[0036] The pyridine compound (Q) has excellent electron transporting properties, and therefore is 4 is preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group. From the viewpoint of ease of synthesis, a hydrogen atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, an anthryl group, a fluoranthenyl group, a pyrenyl group, or a triphenylenyl group is more preferred. 4 is particularly preferably a hydrogen atom.

[0037] Ar 4Examples of the aryl group include a hydrogen atom, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 3,5-dimethylphenyl group, a 2-(1-naphthyl)phenyl group, a 3-(1-naphthyl)phenyl group, a 4-(1-naphthyl)phenyl group, a 2-(2-naphthyl)phenyl group, a 3-(2-naphthyl)phenyl group, a 4-(2-naphthyl)phenyl group, a 2-cyanophenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, a 3 ,5-dicyanophenyl group, 1-phenanthrenyl group, 2-phenanthrenyl group, 3-phenanthrenyl group, 4-phenanthrenyl group, 9-phenanthrenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9-fluorenyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 9,9-dimethylfluoren-1-yl group, 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, 1-triphenylenyl group, 2-triphenylenyl group nyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 2-pyrazyl group, 6-methylpyridin-2-yl group, 3-methylpyridin-2-yl group, 4-methylpyridin-2-yl group, 5-methylpyridin-2-yl group, 2-methylpyridin-3-yl group, 4-methylpyridin-3-yl group, 5-methylpyridin-3-yl group, 6-methylpyridin-3-yl group, 2-methylpyridine -4-yl group, 3-methylpyridin-4-yl group, 2,6-dimethylpyridin-3-yl group, 2,4-dimethylpyridin-3-yl group, 2,5-dimethylpyridin-3-yl group, 6-phenylpyridin-2-yl group, 3-phenylpyridin-2-yl group, 4-phenylpyridin-2-yl group, 5-phenylpyridin-2-yl group, 2-phenylpyridin-3-yl group, 4-phenylpyridin-3-yl group, 5-phenylpyridin-3-yl group, 6-phenylpyridin-3-yl group, 2-phenylpyridin-4-yl group, 3-phenylpyridin-4-yl group,2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinazolyl group, 4-quinazolyl group, 5-quinazolyl group, 6-quinazolyl group, 7-quinazolyl group, 8-quinazolyl group, benzo[h]quinolin-2-yl group, benzo[h]quinolin-3-yl group, benzo[h]quinolin-4-yl group, benzo[h]quinolin-5-yl group , benzo[h]quinolin-6-yl group, benzo[h]quinolin-7-yl group, benzo[h]quinolin-8-yl group, benzo[h]quinolin-9-yl group, benzo[h]quinolin-10-yl group, phenanthridine-1-yl group, benzo[c]quinolin-2-yl group, benzo[c]quinolin-3-yl group, benzo[c]quinolin-4-yl group, benzo[c]quinolin-6-yl group, benzo[c]quinolin-7-yl group, benzo[c]quinolin-8-yl group, benzo[c]quinolin-9-yl group, benzo[c]quinolin-10-yl group, benzo[f]quinolin benzo[f]quinolin-1-yl group, benzo[f]quinolin-2-yl group, benzo[f]quinolin-3-yl group, benzo[f]quinolin-5-yl group, benzo[f]quinolin-6-yl group, benzo[f]quinolin-7-yl group, benzo[f]quinolin-8-yl group, benzo[f]quinolin-9-yl group, benzo[f]quinolin-10-yl group, acridine-1-yl group, acridine-2-yl group, acridine-3-yl group, acridine-4-yl group, acridine-9-yl group, phenazin-1-yl group, phenazin-2-yl group, azatriphenylenyl group, azapyrenyl group , diazatriphenylenyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 2-benzothiophenyl group, 3-benzothiophenyl group, 4-benzothiophenyl group, 5-benzothiophenyl group, 6-benzothiophenyl group, 7-benzothiophenyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group,4-dibenzothiophenyl group, etc.

[0038] [L 1 and L 2 About L 1 and L 2 are each independently Single bond, A divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or It represents a divalent heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element. L 1 and L 2 may each independently be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

[0039] The pyridine compound (Q) has excellent electron transporting properties, 1 and L 2 However, each independently, A single bond, or A divalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group is preferred. In terms of ease of synthesis, a single bond, a phenylene group, a naphthylene group, a phenanthrylene group, an anthrylene group, a triphenylene group, a fluoranthenylene group, or a pyrenylene group is more preferred.

[0040] L 1 and L 2Examples of the alkyl group include a single bond, a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a 1,2-naphthylene group, a 1,3-naphthylene group, a 1,4-naphthylene group, a 1,5-naphthylene group, a 1,2-phenanthrylene group, a 1,3-phenanthrylene group, a 1,4-phenanthrylene group, a 1,5-phenanthrylene group, a 1,6-phenanthrylene group, a 1,7-phenanthrylene group, a 1,8-phenanthrylene group, a 1,9-phenanthrylene group, a 1,10-phenanthrylene group, a 2,3-phenanthrylene group, a 2,4-phenanthrylene group, and a 2,5-phenanthrylene group. group, a 2,6-phenanthrylene group, a 2,7-phenanthrylene group, a 2,8-phenanthrylene group, a 2,9-phenanthrylene group, a 2,10-phenanthrylene group, a 3,4-phenanthrylene group, a 3,5-phenanthrylene group, a 3,6-phenanthrylene group, a 3,7-phenanthrylene group, a 3,8-phenanthrylene group, a 3,9-phenanthrylene group, a 3,10-phenanthrylene group, a 4,5-phenanthrylene group, a 4,6-phenanthrylene group, a 4,7-phenanthrylene group, a 4,8-phenanthrylene group, a 4,9-phenanthrylene group, a 4,10-phenanthrylene group, 1,2-anthrylene group, 1,3-anthrylene group, 1,4-anthrylene group, 1,5-anthrylene group, 1,6-anthrylene group, 1,7-anthrylene group, 1,8-anthrylene group, 1,9-anthrylene group, 1,10-anthrylene group, 2,3-anthrylene group, 2,4-anthrylene group, 2,5-anthrylene group, 2,6-anthrylene group, 2,7-anthrylene group, 2,8-anthrylene group, 2,9-anthrylene group, 2,10-anthrylene group, 9,10-anthrylene group, 1,2-pyrenylene group, 1,3-pyrenylene group, 1,4-pyrenylene group a pyrenylene group, a 1,5-pyrenylene group, a 1,6-pyrenylene group, a 1,7-pyrenylene group, a 1,8-pyrenylene group, a 1,9-pyrenylene group, a 1,10-pyrenylene group, a 2,4-pyrenylene group, a 2,5-pyrenylene group, a 2,6-pyrenylene group, a 2,7-pyrenylene group, a 2,8-pyrenylene group, a 2,9-pyrenylene group, a 2,10-pyrenylene group, a 4,5-pyrenylene group, a 4,6-pyrenylene group, a 4,7-pyrenylene group, a 4,8-pyrenylene group, a 4,9-pyrenylene group, a 4,10-pyrenylene group, a 1,2-triphenylene group, a 1,3-triphenylene group, a 1,4-triphenylene group, a 1,5-triphenylene group, a 1,6-triphenylene group, a 1,7-triphenylene group, a 1,8-triphenylene group, a 1,9-triphenylene group, a 1,10-triphenylene group, a 1,11-triphenylene group, a 1,12-triphenylene group, a 2,3-triphenylene group, a 2,5-triphenylene group, a 2,6-triphenylene group, a 2,7-triphenylene group, a 2,10-triphenylene group, a 2,11-triphenylene group, a 1,2-fluoranthenylene group, a 1,3-fluoranthenylene group, a 1,4-fluoranthenylene group, a 1,5-fluoranthenylene group, a 1,6-fluoranthenylene group, a 1,7-fluoranthenylene group, a 1,8-fluoranthenylene group, a 1,9-fluoranthenylene group, a 1,10-fluoranthenylene group, a 2,3-fluoranthenylene group, a 2,4-fluoranthenylene group, a 2,5-fluoranthenylene group, a 2,7-fluoranthenylene group, a 2,8-fluoranthenylene group, a 2,9-fluoranthenylene group, a 2,10-fluoranthenylene group, a 3,4-fluoranthenylene group, a 3,7-fluoranthenylene group, a 3,8-fluoranthenylene group, a 3,8-fluoranthenylene group, a 3,9-fluoranthenylene group, 3,10-fluoranthenylene group, 7,8-fluoranthenylene group, 7,9-fluoranthenylene group, 7,10-fluoranthenylene group, 8,9-fluoranthenylene group, 8,10-fluoranthenylene group, 2,3-benzofuranylene group, 2,4-benzofuranylene group, 2,5-benzofuranylene group, 2,6-benzofuranylene group, 2,7-benzofuranylene group, 3,4-benzofuranylene group, 3,5-benzofuranylene group, 3,6-benzofuranylene group, 3,7-benzofuranylene group, 4,5-benzofuranylene group, 4 ,6-benzofuranylene group, 4,7-benzofuranylene group, 5,6-benzofuranylene group, 5,7-benzofuranylene group, 6,7-benzofuranylene group, 2,3-benzothiophenylene group, 2,4-benzothiophenylene group, 2,5-benzothiophenylene group, 2,6-benzothiophenylene group, 2,7-benzothiophenylene group, 3,4-benzothiophenylene group, 3,5-benzothiophenylene group, 3,6-benzothiophenylene group, 3,7-benzothiophenylene group, 4,5-benzothiophenylene group, 4,6-benzothiophenylene group, 4,7 -benzothiophenylene group, 5,6-benzothiophenylene group, 5,7-benzothiophenylene group, 6,7-benzothiophenylene group, 1,2-dibenzofuranylene group, 1,3-dibenzofuranylene group, 1,4-dibenzofuranylene group, 1,6-dibenzofuranylene group, 1,7-dibenzofuranylene group, 1,8-dibenzofuranylene group, 1,9-dibenzofuranylene group, 2,3-dibenzofuranylene group, 2,4-dibenzofuranylene group, 2,6-dibenzofuranylene group, 2,7-dibenzofuranylene group, 2,8-dibenzofuranylene group, 2,9-dibenzofuranylene group, a dibenzofuranylene group, a 3,4-dibenzofuranylene group, a 3,6-dibenzofuranylene group, a 3,7-dibenzofuranylene group, a 3,8-dibenzofuranylene group, a 3,9-dibenzofuranylene group, a 4,6-dibenzofuranylene group, a 4,7-dibenzofuranylene group, a 4,8-dibenzofuranylene group, a 4,9-dibenzofuranylene group, a 1,2-dibenzothiophenylene group, a 1,3-dibenzothiophenylene group, a 1,4-dibenzothiophenylene group, a 1,6-dibenzothiophenylene group, a 1,7-dibenzothiophenylene group, a 1,8-dibenzothiophenylene group, a 1,Examples of the dibenzothiophenylene group include 9-dibenzothiophenylene group, 2,3-dibenzothiophenylene group, 2,4-dibenzothiophenylene group, 2,6-dibenzothiophenylene group, 2,7-dibenzothiophenylene group, 2,8-dibenzothiophenylene group, 2,9-dibenzothiophenylene group, 3,4-dibenzothiophenylene group, 3,6-dibenzothiophenylene group, 3,7-dibenzothiophenylene group, 3,8-dibenzothiophenylene group, 3,9-dibenzothiophenylene group, 4,6-dibenzothiophenylene group, 4,7-dibenzothiophenylene group, 4,8-dibenzothiophenylene group, and 4,9-dibenzothiophenylene group. These groups may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

[0041] [L 3 About L 3 teeth, Single bond, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, A divalent heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings and consisting of C, H and N, or It represents a divalent heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element.

[0042] L 3 may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group. The pyridine compound (Q) has excellent electron transporting properties, 3 is preferably a phenylene group.

[0043] L 3Examples of the alkyl group include a single bond, a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a 1,2-naphthylene group, a 1,3-naphthylene group, a 1,4-naphthylene group, a 1,5-naphthylene group, a 1,2-phenanthrylene group, a 1,3-phenanthrylene group, a 1,4-phenanthrylene group, a 1,5-phenanthrylene group, a 1,6-phenanthrylene group, a 1,7-phenanthrylene group, a 1,8-phenanthrylene group, a 1,9-phenanthrylene group, a 1,10-phenanthrylene group, a 2,3-phenanthrylene group, a 2,4-phenanthrylene group, a 2,5 -phenanthrylene group, 2,6-phenanthrylene group, 2,7-phenanthrylene group, 2,8-phenanthrylene group, 2,9-phenanthrylene group, 2,10-phenanthrylene group, 3,4-phenanthrylene group, 3,5-phenanthrylene group, 3,6-phenanthrylene group, 3,7-phenanthrylene group, 3,8-phenanthrylene group, 3,9-phenanthrylene group, 3,10-phenanthrylene group, 4,5-phenanthrylene group, 4,6-phenanthrylene group, 4,7-phenanthrylene group, 4,8-phenanthrylene group, 4,9-phenanthrylene group a 4,10-phenanthrylene group, a 1,2-anthrylene group, a 1,3-anthrylene group, a 1,4-anthrylene group, a 1,5-anthrylene group, a 1,6-anthrylene group, a 1,7-anthrylene group, a 1,8-anthrylene group, a 1,9-anthrylene group, a 1,10-anthrylene group, a 2,3-anthrylene group, a 2,4-anthrylene group, a 2,5-anthrylene group, a 2,6-anthrylene group, a 2,7-anthrylene group, a 2,8-anthrylene group, a 2,9-anthrylene group, a 2,10-anthrylene group, a 9,10-anthrylene group, a 1,2-pyrenylene group, 1,3-pyrenylene group, 1,4-pyrenylene group, 1,5-pyrenylene group, 1,6-pyrenylene group, 1,7-pyrenylene group, 1,8-pyrenylene group, 1,9-pyrenylene group, 1,10-pyrenylene group, 2,4-pyrenylene group, 2,5-pyrenylene group, 2,6-pyrenylene group, 2,7-pyrenylene group, 2,8-pyrenylene group, 2,9-pyrenylene group, 2,10-pyrenylene group, 4,5-pyrenylene group, 4,6-pyrenylene group, 4,7-pyrenylene group, 4,8-pyrenylene group, 4,9-pyrenylene group, 4,10-pyrenylene group, 1,2-triphenylene group, 1,3-triphenylene group, 1,4-triphenylene group, 1,5-triphenylene group, 1,6-triphenylene group, 1,7-triphenylene group, 1,8-triphenylene group, 1,9-triphenylene group, 1,10-triphenylene group, 1,11-triphenylene group, 1,12-triphenylene group, 2,3-triphenylene group, 2,5-triphenylene group, 2,6-triphenylene group, 2,7-triphenylene group, 2,10-triphenylene group, 2,11-triphenylene group, 1,2-fluoranthenylene group, 1,3-fluoranthenylene group, 1,4-fluoranthenylene group, Lanthanylene group, 1,5-fluoranthenylene group, 1,6-fluoranthenylene group, 1,7-fluoranthenylene group, 1,8-fluoranthenylene group, 1,9-fluoranthenylene group, 1,10-fluoranthenylene group, 2,3-fluoranthenylene group, 2,4-fluoranthenylene group, 2,5-fluoranthenylene group, 2,7-fluoranthenylene group, 2,8-fluoranthenylene group, 2,9-fluoranthenylene group, 2,10-fluoranthenylene group, 3,4-fluoranthenylene group, 3,7-fluoranthenylene group, 3,8-fluoranthenylene group, 3,8-fluoranthenylene group, 3,9-fluoranthenylene group, 3,10-fluoranthenylene group, 7,8-fluoranthenylene group, 7,9-fluoranthenylene group, 7,10-fluoranthenylene group, 8,9-fluoranthenylene group, 8,10-fluoranthenylene group, 2,3-benzofuranylene group, 2,4-benzofuranylene group, 2,5-benzofuranylene group, 2,6-benzofuranylene group, 2,7-benzofuranylene group, 3,4-benzofuranylene group, 3,5-benzofuranylene group, 3,6-benzofuranylene group, 3,7-benzofuranylene group benzothiophenylene group, 4,5-benzofuranylene group, 4,6-benzofuranylene group, 4,7-benzofuranylene group, 5,6-benzofuranylene group, 5,7-benzofuranylene group, 6,7-benzofuranylene group, 2,3-benzothiophenylene group, 2,4-benzothiophenylene group, 2,5-benzothiophenylene group, 2,6-benzothiophenylene group, 2,7-benzothiophenylene group, 3,4-benzothiophenylene group, 3,5-benzothiophenylene group, 3,6-benzothiophenylene group, 3,7-benzothiophenylene group, 4,5-benzothiophenylene group, 4,6-benzothiophenylene group, 4,7-benzothiophenylene group, 5,6-benzothiophenylene group, 5,7-benzothiophenylene group, 6,7-benzothiophenylene group, 1,2-dibenzofuranylene group, 1,3-dibenzofuranylene group, 1,4-dibenzofuranylene group, 1,6-dibenzofuranylene group, 1,7-dibenzofuranylene group, 1,8-dibenzofuranylene group, 1,9-dibenzofuranylene group, 2,3-dibenzofuranylene group, 2,4-dibenzofuranylene group, 2, 6-dibenzofuranylene group, 2,7-dibenzofuranylene group, 2,8-dibenzofuranylene group, 2,9-dibenzofuranylene group, 3,4-dibenzofuranylene group, 3,6-dibenzofuranylene group, 3,7-dibenzofuranylene group, 3,8-dibenzofuranylene group, 3,9-dibenzofuranylene group, 4,6-dibenzofuranylene group, 4,7-dibenzofuranylene group, 4,8-dibenzofuranylene group, 4,9-dibenzofuranylene group, 1,2-dibenzothiophenylene group, 1,3-di Benzothiophenylene group, 1,4-dibenzothiophenylene group, 1,6-dibenzothiophenylene group, 1,7-dibenzothiophenylene group, 1,8-dibenzothiophenylene group, 1,9-dibenzothiophenylene group, 2,3-dibenzothiophenylene group, 2,4-dibenzothiophenylene group, 2,6-dibenzothiophenylene group, 2,7-dibenzothiophenylene group, 2,8-dibenzothiophenylene group, 2,9-dibenzothiophenylene group, 3,4-dibenzothiophenylene group , 3,6-dibenzothiophenylene group, 3,7-dibenzothiophenylene group, 3,8-dibenzothiophenylene group, 3,9-dibenzothiophenylene group, 4,6-dibenzothiophenylene group, 4,7-dibenzothiophenylene group, 4,8-dibenzothiophenylene group, 4,9-dibenzothiophenylene group, and the like, and these groups may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

[0044] [L 4 About L 4 represents a trivalent or tetravalent aromatic hydrocarbon group having 6 to 18 carbon atoms. L4 It may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group and a methyl group.

[0045] L 4 Examples of the pyridine compound (Q) include a benzenetriyl group, a naphthalenetriyl group, a phenanthrenetriyl group, an anthracenetriyl group, a triphenylenetriyl group, a fluoranthenetriyl group, a pyrenetriyl group, and the like. 4 is preferably a benzenetriyl group.

[0046] [X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 and X 9 About X 1 , X 2 and X 3 Of these, one is a nitrogen atom and the others are CH. X 4 , X 5 and X 6 Of these, one is a nitrogen atom and the others are CH. X 7 , X 8 and X 9 Of these, one is a nitrogen atom and the others are CH.

[0047] [Regarding a and b] a represents 0, 1 or 2. b represents 1, 2 or 3. a+b is 3. When a is 2, two Ar 3 may be different from each other. When b is 2 or more, multiple L 3 , L 4 , Ar 4 , Q, m and n may be different from each other. In terms of ease of synthesis of the pyridine compound (Q), it is preferable that a is 2.

[0048] [About n] n represents 1 or 2. When n is 2, two L 4 and Ar 4 may be different from each other. In terms of ease of synthesis of the pyridine compound (Q), n is preferably 1.

[0049] [About m] m represents 1 or 2; When m is 2, two Q's may be different from each other; From the viewpoint of ease of synthesis of the pyridine compound (Q), it is preferable that m is 1.

[0050] [About Q] Q is a substituent represented by formula (Q-1), (Q-2) or (Q-3).

[0051] [Specific structural examples of pyridine compounds (Q)] The pyridine compound (Q) is a pyridine compound having a partial structure represented by the formula (Q-1), (Q-2) or (Q-3) and a 1,3,5-triazyl group. Examples of the partial structure represented by formula (Q-1), (Q-2) or (Q-3) include the following (B-1) to (B-207), but the present invention is not limited to these.

[0052] [ka]

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[0075] Examples of the 1,3,5-triazyl group to which the pyridine skeleton exemplified in (B-1) to (B-207) is bonded include the following (T-1) to (T-122), but the present invention is not limited thereto. In addition, Q described in the following (T-1) to (T-122) is any one of the above formulas (Q-1), (Q-2) and (Q-3).

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] [ka]

[0080] [ka]

[0081] [ka]

[0082] Specific examples of the pyridine compound (Q) include the following (A-1) to (A-190), but the present invention is not limited to these.

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[0105] As the pyridine compound (Q), the compounds represented by A-57, A-58, A-60, A-66, A-67, A-69, A-76, A-84, A-85, A-90 and A-117 are preferred because they have good performance as an electron transport material in an organic electroluminescent device.

[0106] Next, a method for producing the pyridine compound (Q) will be described. The pyridine compound (Q) can be produced by the methods shown in the following synthetic pathways (i) to (v).

[0107] [ka]

[0108] [ka]

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[0111] [ka]

[0112] In formulas (2) to (12), Ar 1 , Ar 2 , Ar 3 , Ar 4 , L 1 , L 2 , L 3 , L 4 The definitions of m, n, a and b are the same as those of Ar in formulas (1), (Q-1), (Q-2) and (Q-3), respectively. 1 , Ar 2 , Ar 3 , Ar 4, L 1 , L 2 , L 3 , L 4 , m, n, a and b are the same as defined above; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 each independently represents a halogen atom; R 1 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group; B(OR 1 )2 of 2 R 1 may be the same or different; Two ORs 1 The group and the boron atom may together form a ring.

[0113] Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom or a bromine atom is preferred in terms of the yield of the pyridine compound (Q).

[0114] B(OR 1 )2, for example, B(OH)2, B(OMe)2, B(O i Examples include B(Pr), B(OBu), and B(OPh). Note that Me is a methyl group. i Pr represents an isopropyl group, Bu represents a butyl group, and Ph represents a phenyl group.

[0115] Two ORs 1 When the group and the boron atom are combined to form a ring, B(OR 1 Examples of 2 include the following groups (I) to (VI), with the group (II) being preferred in terms of good yield.

[0116] [ka]

[0117] The coupling reactions in the synthetic routes (i) to (v) are methods in which an aryl halide compound represented by formula (2), (4), (5), (7), (8) or (10) is reacted with a boron compound represented by formula (3), (6), (9), (11) or (12) in the presence of a palladium catalyst and a base, and general reaction conditions for the Suzuki-Miyaura reaction can be applied.

[0118] The boron compound can be produced, for example, according to the method disclosed in The Journal of Organic Chemistry, Vol. 60, p. 7508, 1995 or The Journal of Organic Chemistry, Vol. 65, p. 164, 2000.

[0119] The halogenated aryl compound (2), (4), (5), (7), (8) or (10) can be produced, for example, according to Journal of the American Chemical Society, vol. 74, p. 6289, 1952 or Synlett, p. 808, 2002. Commercially available products may also be used. The halogenated aryl compound is preferably used in an amount of 0.5 to 3.0 molar equivalents relative to the boron compound in terms of good reaction yield.

[0120] The boronation reaction in the synthetic routes (i) to (v) is a method of reacting an aryl halide compound represented by formula (2), (5), (7), (8) or (10) with a boron reagent (e.g., pinacolatoborane, bis-pinacolatodiboron, etc.) in the presence of a palladium catalyst and a base to produce a boron compound represented by formula (3), (6), (9), (11) or (12). These boron compounds can be produced, for example, according to the method disclosed in The Journal of Organic Chemistry, Vol. 60, p. 7508, 1995 or Tetrahedron Letters, Vol. 38, p. 3447, 1997.

[0121] Examples of the palladium catalyst used in the above-mentioned coupling reaction and boronization reaction include palladium salts such as palladium chloride, palladium acetate, palladium trifluoroacetate, and palladium nitrate. In addition, complex compounds such as π-allylpalladium chloride dimer, palladium acetylacetonate, tris(dibenzylideneacetone)dipalladium, bis(dibenzylideneacetone)palladium, dichlorobis(acetonitrile)palladium, and dichlorobis(benzonitrile)palladium; and palladium complexes having tertiary phosphines as ligands such as dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium, dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium, bis(tri-tert-butylphosphine)palladium, bis(tricyclohexylphosphine)palladium, and dichlorobis(tricyclohexylphosphine)palladium; These can also be prepared in the reaction system by adding a tertiary phosphine to a palladium salt or complex compound.

[0122] Examples of tertiary phosphines include triphenylphosphine, trimethylphosphine, tributylphosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(diphenylphosphino)-2'-(N,N-dimethylamino)biphenyl, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, bis(diphenylphosphine), 1,2-bis(diphenylphosphino)methane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1'-bis(diphenylphosphino)ferrocene, tri(2-furyl)phosphine, tri(o-tolyl)phosphine, tris(2,5-xylyl)phosphine, (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, and the like.

[0123] Among these, palladium complexes having a tertiary phosphine as a ligand are preferred in terms of good yield, and palladium complexes having 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl or tricyclohexylphosphine as a ligand are more preferred.

[0124] The molar ratio of the tertiary phosphine to the palladium salt or complex compound is preferably in the range of 1:10 to 10:1, and more preferably in the range of 1:2 to 3:1 in terms of good yield. There is no limitation on the amount of the palladium catalyst used in the above-mentioned coupling reaction and boronation reaction, but in terms of good yield, the molar equivalent of the palladium catalyst is preferably in the range of 0.005 to 0.5 molar equivalent to the boron compound.

[0125] Examples of the base used in the above-mentioned coupling reaction and boronization reaction include metal hydroxide salts such as sodium hydroxide, potassium hydroxide, and calcium hydroxide, metal carbonate salts such as sodium carbonate, potassium carbonate, lithium carbonate, and cesium carbonate, metal acetate salts such as potassium acetate and sodium acetate, metal phosphate salts such as potassium phosphate and sodium phosphate, metal fluoride salts such as sodium fluoride, potassium fluoride, and cesium fluoride, and metal alkoxides such as sodium methoxide, potassium methoxide, sodium ethoxide, potassium isopropyl oxide, and potassium tert-butoxide, etc. Among them, metal carbonates or metal phosphates are preferred in terms of good reaction yield, and potassium carbonate or potassium phosphate is more preferred. There is no particular restriction on the amount of base used. In terms of good reaction yield, the molar ratio of the base to the boron compound is preferably in the range of 1:2 to 10:1, and more preferably in the range of 1:1 to 4:1.

[0126] The aforementioned coupling reaction and boronation reaction can be carried out in a solvent. Examples of the solvent include ethers such as water, diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and tetralin; carbonates such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate; ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, and γ-butyl acetate. esters such as .-lactones; amides such as N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP); ureas such as N,N,N',N'-tetramethylurea (TMU) and N,N'-dimethylpropyleneurea (DMPU); alcohols such as dimethylsulfoxide (DMSO), methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol; and the like. These may be used alone or in any ratio. There is no particular limit to the amount of solvent used. Among these, water, ethers, amides, alcohols, and mixed solvents thereof are preferred in terms of good reaction yield, and a mixed solvent of THF and water, or a mixed solvent of toluene and butanol is more preferred.

[0127] The above-mentioned coupling reaction and boronation reaction can be carried out at a temperature appropriately selected from 0°C to 200°C, and is preferably carried out at a temperature appropriately selected from 60°C to 160°C in terms of good reaction yield.

[0128] After completion of the above-mentioned coupling reaction and boronization reaction, the target product can be obtained by appropriately combining general purification treatments such as recrystallization, column chromatography, sublimation purification, and preparative HPLC as necessary.

[0129] The pyridine compound can be used, for example, in organic electronic devices such as organic electroluminescent devices and photoelectric devices.

[0130] <Materials for organic electroluminescence devices> The material for organic electroluminescent devices according to one aspect of the present invention contains a pyridine compound (Q). The pyridine compound (Q) can be used, for example, as an electron transport material for organic electroluminescence devices. The material for organic electroluminescence devices containing the pyridine compound (Q) has a long life, exhibits high luminous efficiency and low voltage characteristics, and contributes to the preparation of organic electroluminescence devices that can be used for various purposes or under various environments.

[0131] <Organic electroluminescent device> An organic electroluminescent device including a pyridine compound according to one embodiment of the present invention (hereinafter, may be simply referred to as an organic electroluminescent device) will be described below.

[0132] The organic electroluminescent device according to one aspect of the present invention contains a pyridine compound (Q). The configuration of the organic electroluminescent device is not particularly limited, but examples thereof include the following configurations (i) to (v). (i): Anode / Emitting layer / Cathode (ii): anode / hole transport layer / light emitting layer / cathode (iii): anode / light-emitting layer / electron transport layer / cathode (iv): anode / hole transport layer / light emitting layer / electron transport layer / cathode (v): anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0133] The pyridine compound (Q) may be contained in any of the above layers, but is preferably contained in one or more layers selected from the group consisting of the light-emitting layer and the layer between the light-emitting layer and the cathode, in terms of excellent light-emitting properties of the organic electroluminescent device. Therefore, in the case of the structures shown in (i) to (v) above, the pyridine compound (Q) is preferably contained in one or more layers selected from the group consisting of the light-emitting layer, the electron transport layer, and the electron injection layer.

[0134] Hereinafter, an organic electroluminescent device according to one embodiment of the present invention will be described in more detail with reference to FIG. 1, taking the above configuration (v) as an example.

[0135] 1 has a so-called bottom-emission type element configuration, the organic electroluminescent element according to one embodiment of the present invention is not limited to the bottom-emission type element configuration. That is, the organic electroluminescent element according to one embodiment of the present invention may have another known element configuration, such as a top-emission type.

[0136] FIG. 1 is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescent device according to one embodiment of the present invention.

[0137] The organic electroluminescent device 100 includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8 in this order. However, some of these layers may be omitted, or other layers may be added. For example, a hole blocking layer may be provided between the light-emitting layer 5 and the electron transport layer 6, or the hole injection layer 3 may be omitted and the hole transport layer 4 may be provided directly on the anode 2. Alternatively, a single layer having the functions of the multiple layers, such as an electron injection / transport layer having the functions of both the electron injection layer and the electron transport layer in a single layer, may be provided instead of the multiple layers. Furthermore, for example, the single-layer hole transport layer 4 and the single-layer electron transport layer 6 may each be made up of multiple layers.

[0138] <Layer Containing Pyridine Compound (Q)> 1, the organic electroluminescent device 100 contains the pyridine compound (Q) in one or more layers selected from the group consisting of the light-emitting layer 5, the electron transport layer 6, and the electron injection layer 7. In particular, it is preferable that the electron transport layer 6 contains the pyridine compound (Q). The pyridine compound (Q) may be contained in multiple layers of the organic electroluminescent device. In the following, an organic electroluminescent device 100 in which the electron transport layer 6 contains a pyridine compound (Q) will be described.

[0139] [Substrate 1] The substrate 1 is not particularly limited, and examples thereof include a glass plate, a quartz plate, and a plastic plate. Examples of the substrate 1 include a glass plate, a quartz plate, a plastic plate, a plastic film, etc. Among these, a glass plate, a quartz plate, and a light-transmitting plastic film are preferable. Examples of light-transmitting plastic films include films made of polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), etc. In the case of a configuration in which light is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.

[0140] [Anode 2] An anode 2 is provided on the substrate 1 (on the hole injection layer 3 side). Examples of the anode material include metals, alloys, electrically conductive compounds, and mixtures thereof, each having a large work function (e.g., 4 eV or more). Specific examples of the anode material include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO2, and ZnO. In the case of an organic electroluminescent device in which light is extracted through the anode, the anode is formed of a conductive transparent material that is transparent or substantially transparent to the emitted light.

[0141] [Hole injection layer 3, hole transport layer 4] Between the anode 2 and a light-emitting layer 5 described below, a hole injection layer 3 and a hole transport layer 4 are provided in this order from the anode 2 side. The hole injection layer and the hole transport layer have the function of transporting holes injected from the anode to the light-emitting layer. By interposing this hole injection layer and hole transport layer between the anode and the light-emitting layer, a large number of holes can be injected into the light-emitting layer with a lower electric field. The hole injection layer and the hole transport layer also function as electron barrier layers. That is, the electrons injected from the cathode and transported to the light emitting layer from the electron injection layer and / or the electron transport layer are prevented from leaking to the hole injection layer and / or the hole transport layer due to the barrier of electrons present at the interface between the light emitting layer and the hole injection layer and / or the hole transport layer. As a result, the electrons are accumulated at the interface in the light emitting layer, which brings about effects such as improved light emitting efficiency, and an organic electroluminescent device with excellent light emitting performance is obtained.

[0142] The material for the hole injection layer and the hole transport layer has at least one of hole injection property, hole transport property, and electron barrier property. The material for the hole injection layer and the hole transport layer may be either an organic material or an inorganic material.

[0143] Specific examples of materials for the hole injection layer and the hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, conductive polymer oligomers (particularly thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, styrylamine compounds, etc. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred in terms of the good performance of the organic electroluminescent device, and aromatic tertiary amine compounds are particularly preferred.

[0144] Specific examples of aromatic tertiary amine compounds and styrylamine compounds include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'-bis(m-tolyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'- Examples of such compounds include di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)quadriphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), and 4,4',4''-tris[N-(m-tolyl)-N-phenylamino]triphenylamine (MTDATA).

[0145] Furthermore, inorganic compounds such as p-type Si and p-type SiC can also be given as examples of materials for the hole injection layer and the hole transport layer.

[0146] The hole injection layer and the hole transport layer may have a single structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions.

[0147] [Light-emitting layer 5] The light-emitting layer 5 is provided between the hole transport layer 4 and the electron transport layer 6 described below. Examples of materials for the light-emitting layer include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescent materials. In the light-emitting layer, electron-hole pairs are recombined, resulting in light emission. The light-emitting layer may consist of a single small molecule or single polymeric material, but more commonly consists of a host material doped with a guest compound. Emission comes primarily from the dopant and can be of any color.

[0148] Examples of the host material include compounds having a biphenylyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specifically, examples of the compound include DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene)-1,1'-biphenyl), TBADN (2-tertiarybutyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4'-bis(carbazol-9-yl)biphenyl), CDBP (4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl), 2-(9-phenylcarbazol-3-yl)-9-[4-(4-phenylphenylquinazolin-2-yl)carbazole, 9,10-bis(biphenyl)anthracene, and the like.

[0149] Examples of the fluorescent dopant include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compound, thiopyran compound, polymethine compound, pyrylium, thiapyrylium compound, fluorene derivative, periflanthene derivative, indenoperylene derivative, bis(azinyl)amine boron compound, bis(azinyl)methane compound, carbostyril compound, boron compound, cyclic amine compound, etc. The fluorescent dopant may be a combination of two or more selected from these.

[0150] Phosphorescent dopants include, for example, organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

[0151] Specific examples of fluorescent dopants and phosphorescent dopants include Alq3 (tris(8-hydroxyquinoline)aluminum), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III), Ir(PPy)3 (tris(2-phenylpyridine)iridium(III)), and FIrPic (bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III))).

[0152] In addition, the light-emitting material is not limited to being contained only in the light-emitting layer. For example, the light-emitting material may be contained in a layer adjacent to the light-emitting layer (hole transport layer 4 or electron transport layer 6). This can further increase the light-emitting efficiency of the organic electroluminescent device.

[0153] The light-emitting layer may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same composition or different compositions.

[0154] [Electron transport layer 6] An electron transport layer 6 is provided between the light emitting layer 5 and an electron injection layer 7 described below. The electron transport layer has a function of transporting electrons injected from the cathode to the light emitting layer. By interposing the electron transport layer between the cathode and the light emitting layer, electrons are injected into the light emitting layer at a lower electric field.

[0155] The electron transport layer preferably contains a pyridine compound (Q). In addition to the pyridine compound (Q), the electron transport layer may further contain one or more types selected from conventionally known electron transport materials.

[0156] When the pyridine compound (Q) is not contained in the electron transport layer but is contained in another layer, one or more types selected from conventionally known electron transport materials can be used as the electron transport material constituting the electron transport layer.

[0157] Examples of conventionally known electron transporting materials include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Examples of alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include 8-hydroxyquinolinato lithium (Liq), bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, and tris(8-hydroxyquinolinato). Examples of such compounds include gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolate)gallium, bis(2-methyl-8-quinolinato)-1-naphtholate aluminum, and bis(2-methyl-8-quinolinato)-2-naphtholate gallium. The electron transport layer may have a single layer structure made of one or more materials, or a laminate structure made of multiple layers of the same or different compositions.

[0158] In the organic electroluminescent device according to this embodiment, an electron injection layer may be provided for the purpose of improving the electron injection property and improving the device characteristics (for example, luminous efficiency, low-voltage driving, or high durability).

[0159] [Electron injection layer 7] Between the electron transport layer 6 and a cathode 8 described below, an electron injection layer 7 is provided. The electron injection layer has a function of transferring electrons injected from the cathode to the light-emitting layer. By interposing the electron injection layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field. Examples of materials for the electron injection layer include organic compounds such as fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthraquinodimethane, anthrone, etc. Examples of materials for the electron injection layer include inorganic compounds such as various oxides, fluorides, nitrides, and oxynitrides, such as SiO2, AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, LiF, C, and Yb.

[0160] [Cathode 8] A cathode 8 is provided on the electron injection layer 7 . In the case of an organic electroluminescent device in which only light emitted through the anode is extracted, the cathode can be made of any conductive material. Examples of materials for the cathode include metals with a low work function (hereinafter also referred to as electron-injecting metals), alloys, electrically conductive compounds, and mixtures thereof. Here, the metals with a low work function are, for example, metals with a work function of 4 eV or less. Specific examples of cathode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium / copper mixtures, magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al2O3) mixtures, indium, lithium / aluminum mixtures, rare earth metals, and the like. Among these, from the standpoint of electron injection ability and durability against oxidation, etc., mixtures of an electron injecting metal and a second metal which has a larger and more stable work function than the electron injecting metal, such as a magnesium / silver mixture, a magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al2O3) mixture, a lithium / aluminum mixture, etc., are preferred.

[0161] [How each layer is formed] Each layer except for the electrodes (anode, cathode) described above can be formed into a thin film by a known method such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, etc. The material of each layer may be used alone or, if necessary, together with a material such as a binder resin or a solvent. There are no particular limitations on the film thickness of each layer thus formed, and it can be appropriately selected depending on the situation, but it is usually in the range of 5 nm to 5 μm. The anode and cathode can be formed by forming a thin film of an electrode material by a method such as vapor deposition, sputtering, etc. A pattern may be formed through a mask having a desired shape during vapor deposition or sputtering, or a pattern having a desired shape may be formed by photolithography after forming a thin film by vapor deposition, sputtering, etc. The film thickness of the anode and cathode is preferably 1 μm or less, and more preferably 10 nm or more and 200 nm or less.

[0162] In addition, when forming a layer containing the pyridine compound (Q), it may be used in combination with the above-mentioned conventionally known electron transporting material. Therefore, for example, the pyridine compound (Q) and the conventionally known electron transporting material may be co-deposited, or a layer of the conventionally known electron transporting material may be laminated on the layer of the pyridine compound (Q).

[0163] The organic electroluminescent element may be used as a kind of lamp for illumination or exposure light source, or as a projection device for projecting an image onto a screen or the like, or as a display device for directly viewing still images or moving images. When using an organic electroluminescent element as a display device for playing moving images, the driving method may be a simple matrix (passive matrix) method or an active matrix method. In addition, a full-color display device can be produced by using two or more kinds of organic electroluminescent elements having different emission colors.

[0164] The pyridine compound according to one embodiment of the present invention can provide an organic electroluminescence device having significantly superior luminous efficiency and low voltage characteristics when used as an electron transport layer, compared with conventionally known pyridine compounds. Furthermore, the pyridine compound according to one embodiment of the present invention has high amorphousness and high film quality stability due to its steric hindrance skeleton. Therefore, effects such as improvement in driving stability and luminous efficiency of the organic electroluminescence device are expected. Furthermore, the pyridine compound according to one embodiment of the present invention has high chemical stability due to its characteristic skeleton, and can contribute to extending the life of the organic electroluminescence device. The pyridine compound according to one embodiment of the present invention can be used as an electron transport layer in an organic electroluminescence device to provide a pyridine compound capable of achieving low-voltage operation, high efficiency, and long life of the device at a high level. Furthermore, an organic electroluminescence device that can achieve low-voltage operation, high efficiency, and long life using the pyridine compound according to one embodiment of the present invention can be provided. EXAMPLES

[0165] The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited to these examples.

[0166] [ 1 H-NMR measurement] 1 For H-NMR measurements, a Bruker ASCEND HD (400 MHz; manufactured by BRUKER) was used. 1 H-NMR was measured using deuterated chloroform (CDCl3) as the measurement solvent and tetramethylsilane (TMS) as the internal standard. Commercially available reagents were used.

[0167] [DSC measurement (glass transition temperature, crystallization temperature)] The glass transition temperature, crystallization temperature, and melting point were measured using a DSC (Differential Scanning Calorimetry) device DSC7020 (Hitachi High-Tech Science Corp.) Aluminum oxide (Al2O3) was used as the reference in the DSC measurement, and the measurement was performed using 10 mg of the sample. As a pretreatment for the measurement, the sample was heated from 30°C to a temperature above the melting point at a rate of 10°C / min to melt the sample, and then rapidly cooled by contacting the sample with dry ice. The temperature of the pretreated sample was then increased from 30°C at a rate of 10°C / min to measure the glass transition temperature and crystallization temperature.

[0168] [Luminescence property measurement] The light emitting characteristics of the organic electroluminescent device were evaluated by applying a direct current to the device prepared in each Example (described later) in a 25° C. environment using a luminance meter BM-9 (manufactured by Topcon Technohouse Corporation).

[0169] Synthesis Example 1 [ka]

[0170] Under an argon atmosphere, 4,6-bis(4-biphenylyl)-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl-3-yl]-1,3,5-triazine (30.0 g, 52.5 mmol), 1-bromo-3-chlorobenzene (11.7 g, 63.0 mmol), and tetrakis(triphenylphosphine)palladium (2.98 g, 2.63 mmol) were suspended in THF (360 mL). 2.0 M potassium carbonate aqueous solution (75 mL) was added to the suspension, and the mixture was heated to reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture. The resulting solid was collected by filtration and washed with hexane to obtain the desired 4,6-bis(4-biphenylyl)-2-(3'-chloro-biphenyl-3-yl)-1,3,5-triazine (29.3 g, 51.5 mmol, 98%). 1HNMR(CDCl3)δ7.39-7.54(m,8H),7.64(dt,J=3.8,0.8Hz,1H),7.68(dd,J=7.8,7.7Hz,1H),7.70-7.75(m,5H ),7.79-7.85(m,5H),8.82(dt,J=7.8,1.1Hz,1H),8.87(ddd,J=8.4,1.6,1.2Hz,4H),8.97(t,J=1.6Hz,1H).

[0171] Synthesis Example 2 [ka]

[0172] Under an argon atmosphere, 4,6-bis(4-biphenylyl)-2-(3'-chloro-biphenyl-3-yl)-1,3,5-triazine (29.3g, 51.5mmol), bis(pinacolato)diboron (20.1g, 77mmol), palladium acetate (409mg, 1.8mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.7g, 3.6mmol) and potassium acetate (18.8g, 185mmol) were suspended in THF (360mL). After degassing by bubbling argon into the suspension, it was heated to reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture. The resulting solid was collected by filtration and recrystallized from chloroform / hexane to obtain the desired 4,6-bis(4-biphenylyl)-2-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3-yl]-1,3,5-triazine (16.1 g, 24.2 mmol, 48%). 1HNMR(CDCl3)δ1.39(s,12H),7.42(tt,J=7.9,1.5Hz,2H),7.48-7.59(m,5H),7.67(dd,J=8.4,8.2Hz,1H),7.73(d,J=8.3Hz,4H),7.83(d,J =8.4Hz,4H),7.85-7.91(m,3H),8.19(s,1H),8.78(dt,J=8.2,1.2Hz,1H).8.88(ddd,J=8.3,1.9,1.7Hz,4H),9.02(dd,J=1.1,1.0Hz,1H).

[0173] Synthesis Example 3 [ka]

[0174] Under an argon atmosphere, 4,6-bis(4-biphenylyl)-2-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3-yl]-1,3,5-triazine (6.60g, 9.80mmol), 2,3-diphenyl-5-chloropyridine (3.20g, 12.2mmol), palladium acetate (109mg, 0.50mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (480mg, 1.00mmol) were suspended in THF (100mL). 15mL of 2.0M potassium carbonate aqueous solution was added to this suspension and heated to reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture. The resulting solid was filtered and recrystallized from toluene to obtain the desired 4,6-bis(4-biphenylyl)-2-[3'-(5,6-diphenylpyridin-3-yl)-biphenyl-3-yl]-1,3,5-triazine (compound A-84) (3.98 g, 5.19 mmol, 53%). 1HNMR(CDCl3)δ7.26-7.31(m,8H),7.40-7.45(m,4H),7.51(td,J=8.4,1.4Hz,4H),7.67-7.75(m,7H),7.80-7.85(m,5H),7.91(d t,J=7.7,0.9Hz,1H),8.01(t,J=1.6Hz,1H),8.04(d,J=2.2Hz,1H),8.84-8.89(m,5H),9.04(d,2.2Hz,1H),9.06(t,1.6Hz,1H). Compound A-84 had a crystallization temperature of 189°C and a glass transition temperature of 121°C.

[0175] Synthesis Example 4 [ka]

[0176] Under an argon atmosphere, 4,6-bis(4-biphenylyl)-2-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3-yl]-1,3,5-triazine (6.00g, 9.05mmol), 3-chloro-2,6-diphenylpyridine (2.59g, 9.95mmol), palladium acetate (63mg, 0.27mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (262mg, 0.54mmol), 2M aqueous potassium phosphate (13.6mL, 27.2mmol) and THF (90mL) were added and heated under reflux overnight. After cooling, water and methanol were added to the reaction mixture, and the precipitated solid was filtered off. This solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred for 10 minutes, after which the activated carbon was filtered off. The filtrate was concentrated under reduced pressure, and the resulting solid was recrystallized from toluene to obtain the desired 2,4-bis(4-biphenylyl)-6-[3'-(2,6-diphenylpyridin-3-yl)-biphenyl-3-yl]-1,3,5-triazine (compound A-85) (yield: 3.40 g, 49%). 1HNMR(CDCl3)δ7.27-7.35(m,4H),7.39-7.46(m,3H),7.46-7.54(m,7H),7.56-7.63(m,5H),7.68-7.73(m,5H),7.80- 7.85(m,5H),7.92(d,J=7.6Hz,1H),8.18(d,8.0Hz,2H),8.76(d,J=8.0Hz,1H),8.87(d,J=8.8Hz,4H),8.92(brs,1H).

[0177] Synthesis Example 5 [ka]

[0178] Under an argon atmosphere, 4,6-bis(4-biphenylyl)-2-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3-yl]-1,3,5-triazine (8.00g, 12.15mmol), 3-bromo-5-chloro-2-phenylpyridine (3.56g, 13.3mmol), tetrakis(triphenylphosphine)palladium (418mg, 0.36mmol), 2.0M-tripotassium phosphate aqueous solution (18.0mL, 36.2mmol) and THF (120mL) were added and heated under reflux overnight. After cooling, water and methanol were added to the reaction mixture, and the precipitated solid was filtered off. This solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred for 10 minutes, after which the activated carbon was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane / chloroform = 1 / 1) and then recrystallized from toluene to obtain the desired 2,4-bis(4-biphenylyl)-6-[3'-(5-chloro-2-phenylpyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (yield: 5.32 g, 61%). 1HNMR(CDCl3)δ7.24(t,J=7.6Hz,1H),7.28-7.32(m,3H),7.40-7.48(m,5H),7.49-7.59(m,6H),7.62(t,J=7.6Hz,1H),7.69-7.74(m,5H), 7.84(d,8.8Hz,4H),7.87(d,J=2.4Hz,1H),8.69(d,J=2.4Hz,1H),8.77(td,J=1.4,7.8Hz,1H),8.87(d,8.4Hz,4H),8.90(t,J=1.6Hz,1H).

[0179] Synthesis Example 6 [ka]

[0180] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-[3'-(5-chloro-2-phenylpyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (5.32g, 6.94mmol), phenylboronic acid (2.79g, 10.4mmol), palladium acetate (53mg, 0.21mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (203mg, 0.43mmol), 2.0M potassium carbonate aqueous solution (10.0mL, 20.8mmol) and THF (70mL) were added and heated under reflux overnight. After cooling, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. This solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred for 10 minutes. The activated carbon was filtered off from the solution, the filtrate was concentrated under reduced pressure, and the resulting solid was recrystallized from toluene to obtain the desired 2,4-bis(4-biphenylyl)-6-[3'-(2,5-diphenylpyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (compound A-90) (yield: 4.58 g, 87%). 1HNMR(CDCl3)δ7.28-7.34(m,4H),7.37-7.46(m,3H),7.47-7.54(m,9H),7.61-7.63(m,2H),7.66(t,J=1.6Hz,1H),7.71(s,4H),7.7 3(s,3H),7.82(d,J=8.4Hz,4H),8.06(d,J=2.2Hz,1H),8.76-8.79(m,1H)8.87(d,J=8.4Hz,4H),8.93(s,1H),8.98(d,J=2.2Hz,1H).

[0181] Synthesis Example 7 [ka]

[0182] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-[3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (5.88g, 10.0mmol), 5-chloro-2,3-diphenylpyridine (2.93g, 11.0mmol), palladium acetate (72mg, 0.30mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (292mg, 0.60mmol), 2.0M-tripotassium phosphate aqueous solution (15.0mL, 30.0mmol) and THF (90mL) were added and heated under reflux overnight. After cooling, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. This solid was dissolved in chloroform, and activated carbon was added and stirred for 10 minutes. The activated carbon was filtered off from the solution, the filtrate was concentrated under reduced pressure, and then recrystallized from toluene to obtain the desired 2,4-bis(4-biphenylyl)-6-[3-(5,6-diphenylpyridin-3-yl)phenyl]-1,3,5-triazine (compound A-66) (yield: 5.01 g, 73%). 1HNMR(CDCl3)δ7.28-7.31(m,8H),7.40-7.47(m,4H),7.52(t,J=7.6Hz,4H),7.72-7.76(m,5H),7.8 3(d,J=6.8Hz,4H),7.92(d,J=8.0Hz,1H),8.08(d,2.4Hz,1H),8.88(d,J=8.8Hz,5H),9.12(m,2H). Compound A-66 had a crystallization temperature of 194°C and a glass transition temperature of 111°C.

[0183] Synthesis Example 8 [ka]

[0184] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (5.88g, 10.0mmol), 5-chloro-2,3-diphenylpyridine (2.93g, 11.0mmol), palladium acetate (72mg, 0.30mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (292mg, 0.60mmol), 2.0M-tripotassium phosphate aqueous solution (15.0mL, 30.0mmol) and THF (90mL) were added and heated under reflux overnight. After cooling, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. This solid was dissolved in toluene, activated carbon was added thereto, and the mixture was stirred for 10 minutes. The activated carbon was filtered off from the solution, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from toluene to obtain the desired 2,4-bis(4-biphenylyl)-6-[4-(5,6-diphenylpyridin-3-yl)phenyl]-1,3,5-triazine (compound A-57) (yield: 4.97 g, 72%). 1HNMR(CDCl3)δ7.28-7.31(m,5H),7.33-7.35(m,3H),7.41-7.45(m,4H),7.52(t,J=7.6Hz,4H),7.73(d,J=8.8Hz,4H),7.84(d, J=8.4Hz,4H),7.91(d,J=8.4Hz,2H),8.05(d,2.4Hz,1H),8.89(d,J=8.8Hz,4H),8.94(d,J=8.4Hz,2H),9.06(d,J=2.4Hz,1H). The resulting compound A-57 had a crystallization temperature of 228°C and a glass transition temperature of 121°C.

[0185] Synthesis Example 9 [ka]

[0186] Under an argon atmosphere, 2,5-dichloro-4-pyridylboronic acid (7.00 g, 36.5 mmol), iodobenzene (8.93 g, 43.7 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.747 g, 1.09 mmol), 2M aqueous sodium carbonate solution (55.0 mL, 109.4 mmol) and 1,4-dioxane (150 mL) were added and stirred at 110 ° C overnight. After cooling, the solvent was distilled off under reduced pressure, and the mixture was dissolved again in chloroform and washed with water. After distilling off the solvent under reduced pressure, the mixture was purified by silica gel column chromatography (hexane / chloroform = 2 / 1) to obtain the desired 2,5-dichloro-4-phenylpyridine (yield 6.31 g, 77%). 1 H-NMR(CDCl3)δ7.34(s,1H),7.45-7.52(m,5H),8.45(s,1H).

[0187] Synthesis Example 10 [ka]

[0188] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (10.0 g, 17.0 mmol), 2-bromo-3,5-dichloropyridine (4.64 g, 20.4 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.360 g, 0.51 mmol), 2M potassium carbonate aqueous solution (26.0 mL, 51.1 mmol) and tetrahydrofuran (170 mL) were added and heated under reflux overnight. After cooling, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The mixture was dissolved again in hot toluene and treated with activated carbon. The solvent in the filtrate was removed under reduced pressure, and the residue was recrystallized from toluene to obtain the desired 2,4-bis(4-biphenylyl)-6-[4-(3,5-dichloropyridin-2-yl)phenyl]-1,3,5-triazine (yield: 7.31 g, 71%). 1H-NMR(CDCl3)δ7.42(t,J=7.2Hz,2H),7.51(t,J=7.6Hz,4H),7.72(d,J=7.2Hz,4H),7.82(d,J=8.4Hz,4H),7.88(d,J=2.0Hz,1H),7.95(d,J=8.4Hz, 2H),8.62(d,J=2.0Hz,1H),8.87(d,8.4Hz,4H),8.91(d,J=8.4Hz,2H).

[0189] Synthesis Example 11 [ka]

[0190] 2,4-bis(4-biphenylyl)-6-[4-(5-chloro-4-phenylpyridin-2-yl)phenyl]-1,3,5-triazine was synthesized in the same manner as in Synthesis Example 10.

[0191] Synthesis Example 12 [ka]

[0192] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-[4-(5-chloro-4-phenylpyridin-2-yl)-phenyl]-1,3,5-triazine (9.8 g, 15 mmol), phenylboronic acid (2.2 g, 18 mmol), palladium acetate (0.12 g, 0.54 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.51 g, 1.09 mmol) were dissolved in THF (150 mL). 2M potassium carbonate aqueous solution (23 mL) was added thereto, and the mixture was heated to reflux at 80°C for 24 hours. After cooling, water and methanol were added to the reaction mixture. The precipitated solid was collected by filtration and recrystallized from toluene to obtain the desired 2,4-bis(4-biphenylyl)-6-[4-(4,5-diphenylpyridin-2-yl)phenyl]-1,3,5-triazine (compound A-55) (8.63 g, 12.5 mmol, 82%). 1 HNMR(CDCl3)δ7.21-7.35(m,10H),7.42(tt,J=7.3,2.0Hz,2H),7.51(t,J=8.0Hz,4H),7.73(d,J=7.1Hz,4H),7.84(d,J =8.4Hz,4H),7.92(s,1H),8.32(d,J=8.8Hz,2H),8.80(s,1H),8.89(dd,J=8.5,1.8Hz,4H),8.94(dd,J=8.4,1.7Hz,2H).

[0193] Synthesis Example 13 [ka]

[0194] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-[4-(3,5-dichloropyridin-2-yl)phenyl]-1,3,5-triazine (7.28 g, 12.0 mmol), phenylboronic acid (3.66 g, 30.0 mmol), palladium(II) acetate (0.084 g, 0.36 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.348 g, 0.72 mmol), 4M aqueous potassium phosphate (18.0 mL, 72.0 mmol) and tetrahydrofuran (120 mL) were added and heated under reflux overnight. After cooling, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The mixture was dissolved again in chloroform and treated with activated carbon. The solvent in the filtrate was removed under reduced pressure, and the residue was recrystallized from toluene to obtain the desired 2,4-bis(4-biphenylyl)-6-[4-(3,5-diphenylpyridin-2-yl)phenyl]-1,3,5-triazine (compound A-58) (yield: 5.81 g, 70%). 1 H-NMR(CDCl3)δ7.30-7.35(m,5H),7.40-7.55(m,9H),7.65(d,J=8.4Hz,2H),7.72(d,J=8.0Hz,6H),7.81(d ,J=8.4Hz,4H),7.99(d,J=2.0Hz,1H),8.72(d,J=8.4Hz,2H),8.84(d,J=8.4Hz,4H),9.00(d,J=2.0Hz,1H). The resulting compound A-58 had a crystallization temperature of 207°C and a glass transition temperature of 132°C.

[0195] Synthesis Example 14 [ka]

[0196] 2,5-Dichloro-4-(2-naphthyl)pyridine was synthesized in the same manner as in Synthesis Example 9.

[0197] Synthesis Example 15 [ka]

[0198] 2,4-Bis(4-biphenylyl)-6-{3-[5-chloro-3-(2-naphthyl)pyridin-2-yl]phenyl}-1,3,5-triazine was synthesized in the same manner as in Synthesis Example 11.

[0199] Synthesis Example 16 [ka]

[0200] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-{3-[5-chloro-3-(2-naphthyl)-pyridin-2-yl]-phenyl}-1,3,5-triazine (8.0 g, 11.5 mmol), phenylboronic acid (1.54 g, 12.6 mmol), palladium acetate (100 mg, 0.44 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (421 mg, 0.88 mmol) were suspended in THF (100 mL). After adding 2M potassium carbonate aqueous solution (35 mL) to this suspension, the mixture was heated to reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture. The precipitated solid was filtered and recrystallized from toluene to obtain the desired 2,4-bis(4-biphenylyl)-6-{3-[3-(2-naphthyl)-5-phenylpyridin-2-yl]phenyl}-1,3,5-triazine (compound A122) (5.81 g, 7.86 mmol, 68%). 1 HNMR(CDCl3)δ7.35(dd,J=8.6,1.7Hz,1H),7.40-7.57(m,12H),7.68-7.78(m,13H),7.88(d,8.4Hz,1H),8 .00(s,1H),8.13(d,J=2.0Hz,1H),8.69-8.74(m,5H),8.97(dd,J=1.6,1.5Hz,1H),9.06(d,J=2.2Hz,1H).

[0201] Synthesis Example 17 [ka]

[0202] 2,4-Bis(4-biphenylyl)-6-[4-(3,5-dichloropyridin-2-yl)phenyl]-1,3,5-triazine was synthesized in the same manner as in Synthesis Example 10.

[0203] Synthesis Example 18 [ka]

[0204] 2,4-bis(4-biphenylyl)-6-[3-(3,5-diphenylpyridin-2-yl)phenyl]-1,3,5-triazine (compound A-76) was synthesized in the same manner as in Synthesis Example 13. 1 HNMR(CDCl3)δ7.26-7.54(m,15H),7.70-7.74(m,7H),7.79(d,J=8.5Hz,4H),8.00(d,J=2.3Hz ,1H),8.72(dd,J=7.6,1.1Hz,1H),8.78(d,J=8.4Hz,4H),8.84(s,1H),9.00(d,J=2.3Hz,1H). The resulting compound A-76 had a crystallization temperature of 189°C and a glass transition temperature of 120°C.

[0205] Synthesis Example 19 [ka]

[0206] 2,4-Bis(4-biphenylyl)-6-[3-(2,6-diphenylpyridin-3-yl)phenyl]-1,3,5-triazine (compound A-69) was synthesized in the same manner as in Synthesis Example 8. 1HNMR(CDCl3) δ 7.23-7.31(m,3H), 7.39-7.52(m,11H), 7.58(dd,J=8.3Hz,1.7Hz,2H), 7.71(dd,J=8.6,1.2Hz,4H), 7.80(d,J=8.6Hz,4H), 7.86(d,J=8.1Hz,1H), 7.97(d,J=8.1Hz,1H), 8.12(dd,J=8.5,1.5Hz,2H), 8.70(d,J=7.58,1H), 8.73(s,1H), 8.80(d,J=8.6Hz,4H). The crystallization temperature of the obtained compound A-69 was 201°C, and the glass transition temperature was 124°C.

[0207] Synthesis Example 20 [ka]

[0208] 2,4-bis(4-biphenylyl)-6-[4-(2,6-diphenylpyridin-2-yl)phenyl]-1,3,5-triazine (compound A-60) was synthesized in the same manner as in Synthesis Example 7. 1 HNMR(CDCl3)δ7.27-7.29(m,3H),7.38-7.55(m,13H),7.70(dd,J=8.6,1.2Hz,4H),7.80(d,J=8.6Hz,4H),7.83(d ,J=8.0Hz,1H),7.89(d,J=8.0Hz,1H),8.17(dd,J=8.7,1.5Hz,2H),8.74(d,J=8.6Hz,2H),8.84(d,J=8.5Hz,4H). The resulting compound A-60 had a crystallization temperature of 232°C and a glass transition temperature of 139°C.

[0209] Synthesis Example 21 [ka]

[0210] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (19.0 g, 32.3 mmol), 1-bromo-3-chlorobenzene (4.37 g, 12.0 mmol), tetrakis(triphenylphosphine)palladium (747 mg, 0.64 mmol), 2.0 M-tripotassium phosphate aqueous solution (44.0 mL, 97.0 mmol) and THF (323 mL) were added and heated under reflux for 17 hours. After cooling, the precipitated solid was collected by filtration and washed repeatedly with methanol and water. Recrystallization from toluene gave 2,4-bis(4-biphenylyl)-6-(3'-chloro-biphenyl-4-yl)-1,3,5-triazine (yield: 11.2 g, 60%). 1 HNMR(CDCl3): δ7.39-7.49(m,4H),7.49-7.55(m,4H),7.58-7.63(m,1H),7.70-7.74(m,5H),7.77-7.86(m,6H),8.85-8.91(m,6H).

[0211] Synthesis Example 22 [ka]

[0212] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-(3'-chloro-biphenyl-4-yl)-1,3,5-triazine (9.00g, 15.7mmol), bis(pinacolato)diboron (4.79g, 18.9mmol), palladium acetate (71.0mg, 0.32mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.30g, 0.63mmol) and potassium acetate (4.63g, 47.2mmol) were suspended in THF (157mL) and heated under reflux for 17 hours. After cooling, the solution obtained by filtration was concentrated under reduced pressure to a liquid volume of 100mL, and the solid was precipitated by dropping it into 450mL of MeOH solution. After filtering, the solid was repeatedly washed with methanol and water to obtain 2,4-bis(4-biphenylyl)-6-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-yl]-1,3,5-triazine (yield: 8.83 g, 85%). 1 HNMR(CDCl3): δ1.39(s,12H),7.40-7.43(m,2H),7.49-7.54(m,5H),7.73(d,J=8.4,4H),7.80-7.89(m,8H),8.89(s,1H),8.81-8.91(m,6H).

[0213] Synthesis Example 23 [ka]

[0214] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-yl]-1,3,5-triazine (8.80g, 13.3mmol), 3-chloro-2,6-diphenylpyridine (4.07g, 15.9mmol), palladium acetate (60.0mg, 0.27mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.25g, 0.53mmol), 2.0M-tripotassium phosphate aqueous solution (40.0mL, 79.6mmol) and THF (265mL) were added and heated under reflux for 17 hours. After cooling, the precipitated solid was collected by filtration and washed repeatedly with methanol and water. The obtained solid was dissolved in chloroform, activated carbon was added thereto, and the mixture was stirred for 10 minutes. The activated carbon was filtered out from the solution, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from toluene to obtain 2,4-bis(4-biphenylyl)-6-{3'-(2,6-diphenyl-3-pyridinyl)biphenyl-4-yl}-1,3,5-triazine (compound A-172) (yield: 6.67 g, 66%). 1 HNMR(CDCl3):δ7.31-7.39(m,4H),7.40-7.48(m,4H),7.48-7.55(m,7H),7.55-7.67(m,5H),7.70-7.79(m ,4H),7.83-7.7.85(m,5H)7.9-7.95(m,1H),8.19(d,J=8.4,2H),8.81(d,J=8.4,2H),8.88(d,J=8.4,4H).

[0215] Synthesis Example 24 [ka]

[0216] 2,5-Dichloro-4-(1-naphthyl)pyridine was synthesized in the same manner as in Synthesis Example 9.

[0217] Synthesis Example 25 [ka]

[0218] 4,6-bis(4-biphenylyl)-2-{4-[5-chloro-2-(1-naphthyl)pyridin-3-yl]phenyl}-1,3,5-triazine was synthesized in the same manner as in Synthesis Example 11.

[0219] Synthesis Example 26 [ka]

[0220] 4,6-bis(4-biphenylyl)-2-{4-[2-(1-naphthyl)-5-phenylpyridin-2-yl]phenyl}-1,3,5-triazine (compound A-117) was synthesized in the same manner as in Synthesis Example 16. 1 HNMR(CDCl3): δ7.29-7.50(m,13H),7.54-7.57(m,2H),7.68(dd,J=8.3,1.6Hz,4H),7.75-7.78(m,6H),7.81(d,J=8.0 Hz,1H),7.83-7.86(m,2H),8.14(d,J=2.1Hz,1H),8.56(d,J=8.6Hz,2H),8.77(d,J=8.7Hz,4H),9.04(d,J=2.3Hz,1H). The resulting compound A-117 had no detectable crystallization temperature and a glass transition temperature of 151°C.

[0221] Synthesis Example 27 [ka]

[0222] Under an argon atmosphere, 2,4-bis(4-biphenylyl)-6-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (6.46g, 11.0mmol), 3-chloro-2,6-di(naphthalen-1-yl)pyridine (4.37g, 12.0mmol), palladium acetate (80mg, 0.36mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (343mg, 0.72mmol), 2.0M-tripotassium phosphate aqueous solution (18.0mL, 36.0mmol) and THF (120mL) were added and heated under reflux for 17 hours. After cooling, the solvent was distilled off, water was added to the reaction mixture, and the precipitated solid was collected by filtration and washed repeatedly with methanol and hexane. The obtained solid was dissolved in chloroform, activated carbon was added thereto, and the mixture was stirred for 10 minutes. The activated carbon was filtered out from the solution, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from toluene to obtain 2,4-bis(4-biphenylyl)-6-{4-[2,6-di(naphthalene-1-yl)pyridin-3-yl]phenyl}-1,3,5-triazine (compound A-140) (yield: 6.10 g, 70%). 1 HNMR(CDCl3)δ7.35-7.54(m,10H),7.50(brd,J=7.9Hz,4H),7.59(dd,J=8.1,7.2Hz,1H),7.71(brd,J=7.8Hz,4H),7.79(brd,J=8.5Hz,4H),7.79-7. 86(m,4H),7.91-7.93(m,2H),7.96(brd,J=9.1Hz,1H),8.12(d,J=8.0Hz,1 H),8.36(brd,J=9.1Hz,1H),8.58(d,J=8.5Hz,2H),8.80(d,J=8.5Hz,4H).

[0223] Reference example-1 [ka]

[0224] As a reference example, 2,4-bis(4-biphenylyl)-6-[4'-(4-pyridyl)biphenyl-4-yl]-1,3,5-triazine (compound ETL-1) was synthesized in the same manner as described in Example 22 of Japanese Patent No. 2007-314503. The crystallization temperature of the obtained compound ETL-1 was 174° C. The DSC measurement was carried out under the same conditions as in Synthesis Example-7.

[0225] From the above results, it was found that Compound A-66 and Compound A-57 obtained in this Synthesis Example have a higher crystallization temperature than the conventionally known pyridine compound obtained in Reference Example-1.

[0226] Next, the obtained compound was used to carry out element evaluation. Element Example 1 (see Figure 2) (Prepare 1 substrate and 2 anodes) A glass substrate with an indium tin oxide (ITO) transparent electrode, on which a 2 mm wide ITO film (thickness: 110 nm) was patterned in stripes, was prepared as the substrate 1 having an anode 2 on its surface. The substrate was then washed with isopropyl alcohol and then subjected to surface treatment by ozone ultraviolet cleaning.

[0227] (Preparation for vacuum deposition) After cleaning and surface treatment, each layer was deposited by vacuum deposition on the substrate by vacuum deposition, so that each layer was laminated. First, the glass substrate was placed in a vacuum deposition chamber and 1.0×10 -4 The pressure was reduced to 100 Pa. Then, each layer was formed according to the film formation conditions in the following order. Each organic material was formed by resistance heating.

[0228] (Fabrication of Hole Injection Layer 3) Sublimation purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were mixed in a ratio of 99:1 (mass ratio) to form a 10 nm film, producing hole injection 3. The film formation rate was 0.1 nm / sec.

[0229] (Preparation of First Hole Transport Layer 41) Sublimation purified N-[1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine was formed into a film of 85 nm at a rate of 0.2 nm / sec to prepare a first hole transport layer 41 .

[0230] (Preparation of second hole transport layer 42) Sublimation-purified N-phenyl-N-(9,9-diphenylfluoren-2-yl)-N-(1,1′-biphenyl-4-yl)amine was formed into a film of 5 nm at a rate of 0.15 nm / sec to prepare a second hole transport layer 42 .

[0231] (Fabrication of Light-Emitting Layer 5) Sublimation-purified 3-(10-phenyl-9-anthryl)-dibenzofuran and 2,7-bis[N,N-di-(4-tertbutylphenyl)]amino-bisbenzofurano-9,9'-spirofluorene were mixed in a ratio of 95:5 (mass ratio) to form a 20 nm film, thereby producing the light-emitting layer 5. The film formation rate was 0.1 nm / sec.

[0232] (Preparation of Hole Blocking Layer 9) Sublimation-purified 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine was deposited to a thickness of 6 nm at a rate of 0.05 nm / sec to form a hole blocking layer 9.

[0233] (Preparation of Electron Transport Layer 6) 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl]biphenyl-3-yl-1,3,5-triazine (compound A-84) synthesized in Synthesis Example-3 and 8-hydroxyquinolinolato lithium (hereinafter, Liq) were used in a ratio of 50:50 (mass ratio) to form a 25 nm film, to prepare an electron transport layer 6. The film formation speed was 0.15 nm / sec.

[0234] (Fabrication of Electron Injection Layer 7) Liq was deposited at a rate of 0.02 nm / sec to a thickness of 1 nm to form an electron injection layer 7 .

[0235] (Preparation of cathode 8) Finally, a metal mask was placed so as to be perpendicular to the ITO stripes (anode 2) on the substrate 1, and a cathode 8 was formed. The cathode had a two-layer structure in which silver / magnesium (mass ratio 1 / 10) and silver were formed in that order to thicknesses of 80 nm and 20 nm, respectively. The film formation rate of silver / magnesium was 0.5 nm / sec, and the film formation rate of silver was 0.2 nm / sec.

[0236] As a result, the light-emitting area of ​​4 mm2 shown in Figure 2 2 An organic electroluminescence device 100 was produced. The film thickness of each layer was measured using a stylus film thickness measuring instrument (DEKTAK, manufactured by Bruker).

[0237] Furthermore, this element was sealed in a nitrogen atmosphere glove box with oxygen and moisture concentrations of 1 ppm or less by sealing a glass sealing cap and the film-formed substrate (element) with bisphenol F type epoxy resin (manufactured by Nagase ChemteX Corporation).

[0238] Element Example 2 In the element example 1, instead of forming a 25 nm film (film formation speed 0.15 nm / sec) of 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl-]biphenyl-3-yl-1,3,5-triazine (compound A-84) and Liq in a ratio of 50:50 (mass ratio) in the electron transport layer 6, a 25 nm film (film formation speed 0.15 nm / sec) of 2,4-bis(1,1'-biphenyl-4-yl)-6-[3'-(2,4-diphenyl-3-pyridyl-1-yl)-1,1'-biphenyl-3-yl]-1,3,5-triazine (compound A-85) synthesized in Synthesis Example 4 and Liq in a ratio of 50:50 (mass ratio) was formed, except that an organic electroluminescent device was produced in the same manner as in the element example 1.

[0239] Element Example 3 In the element example 1, instead of forming a 25 nm film (film formation speed 0.15 nm / sec) of 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl-]biphenyl-3-yl-1,3,5-triazine (compound A-84) and Liq in a ratio of 50:50 (mass ratio) on the electron transport layer 6, a 25 nm film (film formation speed 0.15 nm / sec) of 2,4-bis(1,1'-biphenyl-4-yl)-6-[3'-(2,5-diphenyl-3-pyridyl-1-yl)-1,1'-biphenyl-3-yl]-1,3,5-triazine (compound A-90) synthesized in Synthesis Example 6 and Liq in a ratio of 50:50 (mass ratio) was formed, except that an organic electroluminescent device was produced in the same manner as in the element example 1.

[0240] Element Example 4 In the element example 1, instead of forming a 25 nm film (film formation speed 0.15 nm / sec) of 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl-]biphenyl-3-yl-1,3,5-triazine (compound A-84) and Liq in a ratio of 50:50 (mass ratio) on the electron transport layer 6, a 25 nm film (film formation speed 0.15 nm / sec) of 2,4-bis(1,1'-biphenyl-4-yl)-6-[3-(4,5-diphenyl-3-pyridyl-1-yl)-phenyl-1-yl]-1,3,5-triazine (compound A-66) synthesized in Synthesis Example 7 and Liq in a ratio of 50:50 (mass ratio) was formed, except that an organic electroluminescent device was produced in the same manner as in the element example 1.

[0241] Element Example 5 In the element example 1, instead of forming a 25 nm film (film formation speed 0.15 nm / sec) of 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl-]biphenyl-3-yl-1,3,5-triazine (compound A-84) and Liq in a ratio of 50:50 (mass ratio) on the electron transport layer 6, a 25 nm film (film formation speed 0.15 nm / sec) of 2,4-bis(1,1'-biphenyl-4-yl)-6-[4-(4,5-diphenyl-3-pyridyl-1-yl)-phenyl-1-yl]-1,3,5-triazine (compound A-57) synthesized in Synthesis Example 8 and Liq in a ratio of 50:50 (mass ratio) was formed, except that an organic electroluminescent device was produced in the same manner as in the element example 1.

[0242] Element Example 6 In the element example 1, instead of forming a 25 nm film (film formation speed 0.15 nm / sec) of 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl-]biphenyl-3-yl-1,3,5-triazine (compound A-84) and Liq in a ratio of 50:50 (mass ratio) in the electron transport layer 6, a 25 nm film (film formation speed 0.15 nm / sec) of 2,4-bis(4-biphenylyl)-6-[3-(3,5-diphenylpyridin-2-yl)phenyl]-1,3,5-triazine (compound A-76) synthesized in Synthesis Example 18 and Liq in a ratio of 50:50 (mass ratio) was formed, and an organic electroluminescent device was produced in the same manner as in the element example 1.

[0243] Element Example 7 In the element example 1, instead of forming a 25 nm film (film formation speed 0.15 nm / sec) of 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl-]biphenyl-3-yl-1,3,5-triazine (compound A-84) and Liq in a ratio of 50:50 (mass ratio) in the electron transport layer 6, a 25 nm film (film formation speed 0.15 nm / sec) of 2,4-bis(4-biphenylyl)-6-[4-(2,6-diphenylpyridin-2-yl)phenyl]-1,3,5-triazine (compound A-60) synthesized in Synthesis Example 20 and Liq in a ratio of 50:50 (mass ratio) was formed in the electron transport layer 6. An organic electroluminescent device was produced in the same manner as in the element example 1.

[0244] Element Example 8 In the element example 1, instead of forming a 25 nm film (film formation speed 0.15 nm / sec) of 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl-]biphenyl-3-yl-1,3,5-triazine (compound A-84) and Liq in a ratio of 50:50 (mass ratio) in the electron transport layer 6, a 25 nm film (film formation speed 0.15 nm / sec) of 2,4-bis(4-biphenylyl)-6-[4-(3,5-diphenylpyridin-2-yl)phenyl]-1,3,5-triazine (compound A-58) synthesized in Synthesis Example 13 and Liq in a ratio of 50:50 (mass ratio) was formed, and an organic electroluminescent device was produced in the same manner as in the element example 1.

[0245] Element Example 9 In the element example 1, instead of forming a 25 nm film (film formation speed 0.15 nm / sec) of 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl-]biphenyl-3-yl-1,3,5-triazine (compound A-84) and Liq in a ratio of 50:50 (mass ratio) in the electron transport layer 6, a 25 nm film (film formation speed 0.15 nm / sec) of 2,4-bis(4-biphenylyl)-6-[3-(2,6-diphenylpyridin-3-yl)phenyl]-1,3,5-triazine (compound A-69) synthesized in Synthesis Example 19 and Liq in a ratio of 50:50 (mass ratio) was formed, and an organic electroluminescent device was produced in the same manner as in the element example 1.

[0246] Element Example 10 In the element example 1, instead of forming a 25 nm film (film formation speed 0.15 nm / sec) of 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl-]biphenyl-3-yl-1,3,5-triazine (compound A-84) and Liq in a ratio of 50:50 (mass ratio) in the electron transport layer 6, a 25 nm film (film formation speed 0.15 nm / sec) of 4,6-bis(4-biphenylyl)-2-{4-[2-(1-naphthyl)-5-phenylpyridin-2-yl]phenyl}-1,3,5-triazine (compound A-117) synthesized in Synthesis Example 26 and Liq in a ratio of 50:50 (mass ratio) was formed, except that an organic electroluminescent device was produced in the same manner as in the element example 1.

[0247] Element reference example 1 An organic electroluminescent device was produced in the same manner as in Element Example-1, except that, instead of forming a 25 nm film (film formation rate of 0.15 nm / sec) of 4,6-bis(biphenyl)-2-[3'-(2,3-diphenyl)-pyridyl-5-yl-]biphenyl-3-yl-1,3,5-triazine (compound A-84) and Liq in a ratio of 50:50 (mass ratio) in the electron transport layer 6, a 25 nm film (film formation rate of 0.15 nm / sec) of ETL-1 synthesized in Reference Example-1 and Liq in a ratio of 50:50 (mass ratio) was formed.

[0248] A direct current was applied to the produced organic electroluminescent device, and the light-emitting characteristics were evaluated according to the method described in the above-mentioned measurement of light-emitting characteristics. The light emission characteristics are as follows: current density 10mA / cm 2 The voltage (V) and power efficiency (lm / A) were measured when current was applied, and the element lifespan during continuous lighting was measured. The element lifespan is measured when the initial luminance is 1000 cd / m 2 The luminance decay time was measured when the device was continuously lit when driven at 1000 Hz, and the luminance (cd / m 2 The time required for the capacitance to decrease by 5% was measured. The voltage (V), power efficiency (lm / A) and lifespan values ​​were expressed as relative values ​​with the value of Reference Example Element-1 taken as 100. The results are shown in Table 1.

[0249] [Table 1]

[0250] From Table 1, it was found that the organic electroluminescent device using the pyridine compound (Q) was highly superior in voltage, power efficiency and device life, as compared with the reference example. [Explanation of symbols]

[0251] 1. Substrate 2.Anode 3. Hole injection layer 4. Hole transport layer 5.Emitting layer 6.Electron transport layer 7.Electron injection layer 8.Cathode 9. Hole blocking layer 41. First hole transport layer 42. Second hole transport layer 100. Organic electroluminescent device

Claims

1. A pyridine compound represented by formula (1): 【Chemistry 1】 During the ceremony, Ar ３ teeth, an aromatic hydrocarbon group having 6 to 18 carbon atoms; A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element; Ar ４ teeth, Represents a hydrogen atom; L ３ teeth, represents a single bond, a 1,2-phenylene group, a 1,3-phenylene group, or a 1,4-phenylene group; L ４ represents a trivalent or tetravalent aromatic hydrocarbon group having 6 to 18 carbon atoms; a represents 0, 1 or 2: b represents 1, 2 or 3; a+b is 3; n represents 1 or 2; When n is 2, two L ４ may be different from each other; m represents 1 or 2; When m is 2, two Q's may be different from each other; When a is 2, two Ar ３ may be different from each other; When b is 2 or more, multiple L ３ , L ４ , Q, m and n may be different from each other; Q is a substituent represented by formula (Q-1), (Q-2) or (Q-3): 【Chemistry 2】 During the ceremony, L １ and L ２ are each independently Single bond, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or represents a divalent heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element; Ar １ and Ar ２ are each independently an aromatic hydrocarbon group having 6 to 18 carbon atoms; A heteroaromatic group having 4 to 17 carbon atoms and consisting of only 6-membered rings, C, H and N, or represents a heteroaromatic group having 8 to 16 carbon atoms and consisting of C, H and a Group 16 element; L １ is a single bond, Ar １ is an aromatic hydrocarbon group having 6 to 18 carbon atoms; L ２ is a single bond, Ar ２ is an aromatic hydrocarbon group having 6 to 18 carbon atoms; X １ , X ２ and X ３ one of which is a nitrogen atom and the others are C—H; X ４ , X ５ and X ６ one of which is a nitrogen atom and the others are C—H; X ７ , X ８ and X ９ one of which is a nitrogen atom and the others are C—H; L １ , L ２ , L ３ , L ４ , Ar １ , Ar ２ , and Ar ３ may each independently be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

2. The pyridine compound according to claim 1, wherein Q is a substituent represented by formula (Q-1) or (Q-3).

3. The pyridine compound according to claim 1, wherein Q is a substituent represented by formula (Q-2).

4. Ar ３ is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

5. L １ and L ２ However, each independently, A single bond, or The pyridine compound according to any one of claims 1 to 3, which is a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

6. L １ and L ２ The pyridine compound according to claim 1 , wherein each of the following is independently a single bond, a phenylene group, a naphthylene group, a phenanthrylene group, an anthrylene group, a triphenylene group, a fluoranthenylene group, or a pyrenylene group.

7. Ar １ and Ar ２ wherein each independently represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with one or more groups selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a cyano group, and a methyl group.

8. Ar １ and Ar ２ The pyridine compound according to any one of claims 1 to 4, wherein each of the is independently a phenyl group, a biphenylyl group, a naphthyl group or a pyridylphenyl group.

9. A material for an organic electroluminescent device, comprising the pyridine compound according to claim 1 .

10. An electron transport material for an organic electroluminescent device, comprising the pyridine compound according to claim 1 .

11. An organic electroluminescent device comprising the pyridine compound according to claim 1 .

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