JP7206816B2 - Cyclic azine compound, material for organic electroluminescence device, electron transport material for organic electroluminescence device, and organic electroluminescence device - Google Patents

Description

TECHNICAL FIELD The present invention relates to a cyclic azine compound, a material for organic electroluminescent devices, an electron-transporting material for organic electroluminescent devices, and an organic electroluminescent device.

Organic electroluminescence devices are used not only for small displays but also for large-sized televisions, lighting, and the like, and are being vigorously developed.
For example, Patent Document 1 discloses, as a material for an organic electroluminescent device, a cyclic azine compound having a specific substituent, which contributes to the provision of an organic electroluminescent device having excellent heat resistance, a low driving voltage, and a long life. there is
Patent Document 2 discloses a cyclic azine compound having a diarylpyridine structure.

JP 2011-063584 A WO2017/221974

In recent years, however, the demand for organic electroluminescence devices from the market has increased more and more, and materials that are excellent in all of current efficiency characteristics, drive voltage characteristics, and long life characteristics are in demand.
Here, although the organic electroluminescence device using the cyclic azine compound disclosed in Patent Document 1 exhibits excellent driving voltage characteristics, there is a demand for further improvements in device life and current efficiency.
In addition, although the organic electroluminescence device using the cyclic azine compound disclosed in Patent Document 2 exhibits better current efficiency and longer life than those of Patent Document 1, there is still room for further improvement in device life. It has been demanded. Especially in recent years, since the number of years of use of smartphones tends to increase, organic electroluminescent elements are required to be able to withstand long-term use. is extremely high.

One aspect of the present invention is directed to providing a cyclic azine compound, a material for an organic electroluminescence device, and an electron transport material for an organic electroluminescence device that are excellent in durability and current efficiency.
Another aspect of the present invention is directed to providing an organic electroluminescence device that is excellent in durability and current efficiency.

A cyclic azine compound according to one aspect of the present invention is represented by formula (1):

In formula (1),
Ar ¹ are the same as each other and represent a 2-biphenyl group, a 3-biphenyl group, or a 4-biphenyl group;
Ar ² and Ar ³ are each independently
A monocyclic ring that may be linked, a condensed ring that may be linked, or a structure in which these are linked,
(i) an aromatic hydrocarbon group having 6 to 24 carbon atoms,
(ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting only of a 6-membered ring, or
(iii) a heteroaromatic group having 3 to 25 carbon atoms composed of atoms selected from the group consisting of H, C, O, and S, or
(iv) represents a group composed of a combination of any two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ² and Ar ³ is 4 to 25;
one of Z ¹ and Z ² represents a nitrogen atom and the other represents C—H;
A forms a single bond with B ¹ or B ² ;
one of B ¹ and B ² forms a single bond with A and the other represents a hydrogen atom;
Each group represented by Ar ² and Ar ³ is each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and 1 It may have one or more groups selected from the group consisting of 4 to 4 alkoxy groups.

A material for an organic electroluminescence device according to another aspect of the present invention contains the cyclic azine compound.
An electron-transporting material for an organic electroluminescence device according to another aspect of the present invention contains the cyclic azine compound.
An organic electroluminescence device according to another aspect of the present invention contains the above cyclic azine compound.

According to one aspect of the present invention, it is possible to provide a cyclic azine compound, a material for an organic electroluminescence device, and an electron transport material for an organic electroluminescence device that are excellent in durability and current efficiency.
According to another aspect of the present invention, it is possible to provide an organic electroluminescence device excellent in durability and current efficiency.

1 is a schematic cross-sectional view showing an example of a lamination structure of an organic electroluminescence device containing a cyclic azine compound according to one embodiment of the present invention; FIG. 1 is a schematic cross-sectional view showing an example of a lamination structure of an organic electroluminescence device containing a cyclic azine compound according to one aspect of the present invention (Device Example-1). FIG.

The cyclic azine compound according to one embodiment of the present invention is described in detail below.

<Cyclic azine compound>
A cyclic azine compound according to one aspect of the present invention is represented by formula (1):

In formula (1),
Ar ¹ are the same as each other and represent a 2-biphenyl group, a 3-biphenyl group, or a 4-biphenyl group;
Ar ² and Ar ³ are each independently
A monocyclic ring that may be linked, a condensed ring that may be linked, or a structure in which these are linked,
(i) an aromatic hydrocarbon group having 6 to 24 carbon atoms,
(ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting only of a 6-membered ring, or
(iii) a heteroaromatic group having 3 to 25 carbon atoms composed of atoms selected from the group consisting of H, C, O, and S, or
(iv) represents a group composed of a combination of any two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ² and Ar ³ is 4 to 25;
one of Z ¹ and Z ² represents a nitrogen atom and the other represents C—H;
A forms a single bond with B ¹ or B ² ;
one of B ¹ and B ² forms a single bond with A and the other represents a hydrogen atom;
Each group represented by Ar ² and Ar ³ is each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and 1 It may have one or more groups selected from the group consisting of 4 to 4 alkoxy groups.

Hereinafter, the cyclic azine compound represented by formula (1) may be referred to as cyclic azine compound (1). Definitions of substituents in the cyclic azine compound (1) and preferred specific examples thereof are as follows.

[About Ar ¹ ]
In formula (1), Ar ¹ are the same and represent a 2-biphenyl group, a 3-biphenyl group, or a 4-biphenyl group.
Ar ¹ is more preferably a 4-biphenyl group from the viewpoint of excellent electron-transporting material properties.

[Regarding Ar ² and Ar ³ ]
In formula (1), Ar ² and Ar ³ are each independently
(i) an aromatic hydrocarbon group having 6 to 24 carbon atoms, which is a monocyclic ring that may be linked, a condensed ring that may be linked, or a structure in which these are linked;
(ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting only of a 6-membered ring, which is a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked;
(iii) composed of atoms selected from the atomic group consisting of H, C, O, and S, which is a single ring that may be linked, a condensed ring that may be linked, or a structure in which these are linked heteroaromatic group having 3 to 25 carbon atoms;
(iv) represents a group composed of any combination of two or more selected from the above (i) to (iii).
Each group (i) to (iv) represented by Ar ² and Ar ³ is each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, and 1 to 1 carbon atoms. 4 alkyl groups and alkoxy groups having 1 to 4 carbon atoms. Ar ² and Ar ³ more preferably have no substituents.

Examples of the aromatic hydrocarbon group (i) include, but are not limited to, phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, and triphenylenyl group. , a chrysenyl group, a perylenyl group, a fluoranthenyl group, an acenaphthyl group and the like are preferred examples. As described above, these substituents (aromatic hydrocarbon groups) are each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and one or more groups selected from the group consisting of alkoxy groups having 1 to 4 carbon atoms.

The nitrogen-containing heteroaromatic group (ii) is not particularly limited, but examples include pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, quinolyl group, isoquinolyl group, phenanthridyl group, and benzoquinolyl group. , an acridinyl group and the like are preferred examples. A heteroaromatic group containing a 5-membered ring (for example, a carbazolyl group) is not included in (ii) a nitrogen-containing heteroaromatic group, nor is it included in the cyclic azine compound represented by formula (1). Further, as described above, these substituents (nitrogen-containing heteroaromatic groups) are each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, or a It may have one or more groups selected from the group consisting of an alkyl group and an alkoxy group having 1 to 4 carbon atoms.

The heteroaromatic group (iii) is not particularly limited, but examples thereof include thienyl group, furyl group, bithienyl group, bifuryl group, benzothienyl group, benzofuryl group, dibenzothienyl group, dibenzofuryl group, and the like. is mentioned as a preferable example. As described above, these substituents (heteroaromatic groups) are each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, and an alkyl group having 1 to 4 carbon atoms. , and an alkoxy group having 1 to 4 carbon atoms.

The alkyl group having 1 to 4 carbon atoms in Ar ² and Ar ³ is not particularly limited, but examples include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, t-butyl Preferred examples include groups and the like.

The alkoxy group having 1 to 4 carbon atoms in Ar ² and Ar ³ is not particularly limited, but may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, t- Preferred examples include a butoxy group and the like.

Specific examples of the groups represented by Ar ² and Ar ³ are not particularly limited, but preferable examples include groups (1) to (44) shown below.

(1): phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, mesityl group, 2-ethylphenyl group, 3-ethyl phenyl group, 4-ethylphenyl group, 2,4-diethylphenyl group, 3,5-diethylphenyl group, 2-propylphenyl group, 3-propylphenyl group, 4-propylphenyl group, 2,4-dipropylphenyl group, 3,5-dipropylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2,4-diisopropylphenyl group, 3,5-diisopropylphenyl group, 2-butylphenyl group , 3-butylphenyl group, 4-butylphenyl group, 2,4-dibutylphenyl group, 3,5-dibutylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butyl phenyl group, 2,4-di-tert-butylphenyl group, 3,5-di-tert-butylphenyl group;

(2): biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl group, 4'-methyl biphenyl-4-yl group, 2,2'-dimethylbiphenyl-4-yl group, 6-methylbiphenyl-3-yl group, 5-methylbiphenyl-3-yl group, 2'-methylbiphenyl-3-yl group , 4'-methylbiphenyl-3-yl group, 6,2'-dimethylbiphenyl-3-yl group, 5-methylbiphenyl-2-yl group, 6-methylbiphenyl-2-yl group, 2'-methylbiphenyl -2-yl group, 4'-methylbiphenyl-2-yl group, 6,2'-dimethylbiphenyl-2-yl group, 3-ethylbiphenyl-4-yl group, 6-ethylbiphenyl-3-yl group, 5-ethylbiphenyl-2-yl group, 3-propylbiphenyl-4-yl group, 6-propylbiphenyl-3-yl group, 5-propylbiphenyl-2-yl group, 3-isopropylbiphenyl-4-yl group, 6-isopropylbiphenyl-3-yl group, 5-isopropylbiphenyl-2-yl group, 3-butylbiphenyl-4-yl group, 6-butylbiphenyl-3-yl group, 5-butylbiphenyl-2-yl group, 3-tert-butylbiphenyl-4-yl group, 4'-tert-butylbiphenyl-4-yl group, 6-tert-butylbiphenyl-3-yl group, 5-tert-butylbiphenyl-2-yl group.

(3): 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-methylpyridin-3-yl group, 2-methylpyridin-4-yl group, 2-methylpyridin-5-yl group, 2 -methylpyridin-6-yl group, 3-methylpyridin-2-yl group, 3-methylpyridin-4-yl group, 3-methylpyridin-5-yl group, 3-methylpyridin-6-yl group, 4 -methylpyridin-2-yl group, 4-methylpyridin-3-yl group, 2,6-dimethylpyridin-3-yl group, 2,6-dimethylpyridin-4-yl group, 3,6-dimethylpyridin- 2-yl group, 3,6-dimethylpyridin-4-yl group, 3,6-dimethylpyridin-5-yl group;

(4): 2-phenylpyridin-6-yl group, 3-phenylpyridin-6-yl group, 4-phenylpyridin-6-yl group, 5-phenylpyridin-6-yl group, 2-phenylpyridin-3 -yl group, 2-phenylpyridin-5-yl group, 3-phenylpyridin-5-yl group, 4-phenylpyridin-3-yl group, 3-phenylpyridin-4-yl group, 2-phenylpyridin-4 -yl group, 2-(2-pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 3-(3-pyridyl) ) phenyl group, 4-(3-pyridyl)phenyl group, 2-(4-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 2-(3-methyl -2-pyridyl)phenyl group, 3-(3-methyl-2-pyridyl)phenyl group, 4-(3-methyl-2-pyridyl)phenyl group, 2-(4-methyl-2-pyridyl)phenyl group, 3-(4-methyl-2-pyridyl)phenyl group, 4-(4-methyl-2-pyridyl)phenyl group, 2-(5-methyl-2-pyridyl)phenyl group, 3-(5-methyl-2 -pyridyl)phenyl group, 4-(5-methyl-2-pyridyl)phenyl group, 2-(6-methyl-2-pyridyl)phenyl group, 3-(6-methyl-2-pyridyl)phenyl group, 4- (6-methyl-2-pyridyl)phenyl group, 2-(2-methyl-3-pyridyl)phenyl group, 3-(2-methyl-3-pyridyl)phenyl group, 4-(2-methyl-3-pyridyl) ) phenyl group, 2-(4-methyl-3-pyridyl)phenyl group, 3-(4-methyl-3-pyridyl)phenyl group, 4-(4-methyl-3-pyridyl)phenyl group, 2-(5 -methyl-3-pyridyl)phenyl group, 3-(5-methyl-3-pyridyl)phenyl group, 4-(5-methyl-3-pyridyl)phenyl group, 2-(6-methyl-3-pyridyl)phenyl group, 3-(6-methyl-3-pyridyl)phenyl group, 4-(6-methyl-3-pyridyl)phenyl group, 2-(2-methyl-4-pyridyl)phenyl group, 3-(2-methyl -4-pyridyl)phenyl group, 4-(2-methyl-4-pyridyl)phenyl group, 2-(3-methyl-4-pyridyl)phenyl group, 3-(3-methyl-4-pyridyl)phenyl group, 4-(3-methyl-4-pyridyl)phenyl group, 2,6-diphenylpyridin-3-yl group, 2, 6-diphenylpyridin-4-yl group, 4,6-diphenylpyridin-2-yl group, 3,6-diphenylpyridin-4-yl group, 3,6-diphenylpyridin-5-yl group.

(5): 1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalene-2-yl group, 1-phenylnaphthalene-3-yl group, 1-phenylnaphthalene-4-yl group, 1-phenylnaphthalene-5 -yl group, 1-phenylnaphthalene-6-yl group, 1-phenylnaphthalene-7-yl group, 1-phenylnaphthalene-8-yl group, 2-phenylnaphthalene-1-yl group, 2-phenylnaphthalene-3 -yl group, 2-phenylnaphthalene-4-yl group, 2-phenylnaphthalene-5-yl group, 2-phenylnaphthalene-6-yl group, 2-phenylnaphthalene-7-yl group, 2-phenylnaphthalene-8 -yl group, 1-methylnaphthalene-4-yl group, 1-methylnaphthalene-5-yl group, 1-methylnaphthalene-6-yl group, 1-methylnaphthalene-7-yl group, 1-methylnaphthalene-8 -yl group, 2-methylnaphthalene-1-yl group, 2-methylnaphthalene-3-yl group, 2-methylnaphthalene-4-yl group, 2-methylnaphthalene-5-yl group, 2-methylnaphthalene-6 -yl group, 2-methylnaphthalene-7-yl group, 2-methylnaphthalene-8-yl group.

(6): 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-phenylphenanthren-2-yl group, 1-phenylphenanthren-3-yl group, 1 -phenylphenanthren-4-yl group, 1-phenylphenanthren-5-yl group, 1-phenylphenanthren-6-yl group, 1-phenylphenanthren-7-yl group, 1-phenylphenanthren-8-yl group, 1 -phenylphenanthren-9-yl group, 1-phenylphenanthren-10-yl group, 2-phenylphenanthren-1-yl group, 2-phenylphenanthren-3-yl group, 2-phenylphenanthren-4-yl group, 2 -phenylphenanthren-5-yl group, 2-phenylphenanthren-6-yl group, 2-phenylphenanthren-7-yl group, 2-phenylphenanthren-8-yl group, 2-phenylphenanthren-9-yl group, 2 -phenylphenanthren-10-yl group, 3-phenylphenanthren-1-yl group, 3-phenylphenanthren-2-yl group, 3-phenylphenanthren-4-yl group, 3-phenylphenanthren-5-yl group, 3 -phenylphenanthren-6-yl group, 3-phenylphenanthren-7-yl group, 3-phenylphenanthren-8-yl group, 3-phenylphenanthren-9-yl group, 3-phenylphenanthren-10-yl group, 4 -phenylphenanthren-1-yl group, 4-phenylphenanthren-2-yl group, 4-phenylphenanthren-3-yl group, 4-phenylphenanthren-5-yl group, 4-phenylphenanthren-6-yl group, 4 -phenylphenanthren-7-yl group, 4-phenylphenanthren-8-yl group, 4-phenylphenanthren-9-yl group, 4-phenylphenanthren-10-yl group, 1-methylphenanthren-2-yl group, 1 -methylphenanthren-3-yl group, 1-methylphenanthren-4-yl group, 1-methylphenanthren-5-yl group, 1-methylphenanthren-6-yl group, 1-methylphenanthren-7-yl group, 1 -methylphenanthren-8-yl group, 1-methylphenanthren-9-yl group, 1-methylphenanthren-10-yl group, 2-methylphenanthren-1-yl group, 2-methylphenanthren-3-yl group, 2 - methylphene Nanthren-4-yl group, 2-methylphenanthren-5-yl group, 2-methylphenanthren-6-yl group, 2-methylphenanthren-7-yl group, 2-methylphenanthren-8-yl group, 2-methyl phenanthren-9-yl group, 2-methylphenanthren-10-yl group, 3-methylphenanthren-1-yl group, 3-methylphenanthren-2-yl group, 3-methylphenanthren-4-yl group, 3-methyl phenanthren-5-yl group, 3-methylphenanthren-6-yl group, 3-methylphenanthren-7-yl group, 3-methylphenanthren-8-yl group, 3-methylphenanthren-9-yl group, 3-methyl phenanthren-10-yl group, 4-methylphenanthren-1-yl group, 4-methylphenanthren-2-yl group, 4-methylphenanthren-3-yl group, 4-methylphenanthren-5-yl group, 4-methyl phenanthren-6-yl group, 4-methylphenanthren-7-yl group, 4-methylphenanthren-8-yl group, 4-methylphenanthren-9-yl group, 4-methylphenanthren-10-yl group;

(7): 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenylanthracen-2-yl group, 1-phenylanthracen-3-yl group, 1-phenylanthracen-4-yl group, 1 -phenylanthracen-5-yl group, 1-phenylanthracen-6-yl group, 1-phenylanthracen-7-yl group, 1-phenylanthracen-8-yl group, 1-phenylanthracen-9-yl group, 1 -phenylanthracen-10-yl group, 2-phenylanthracen-1-yl group, 2-phenylanthracen-3-yl group, 2-phenylanthracen-4-yl group, 2-phenylanthracen-5-yl group, 2 -phenylanthracen-6-yl group, 2-phenylanthracen-7-yl group, 2-phenylanthracen-8-yl group, 2-phenylanthracen-9-yl group, 2-phenylanthracen-10-yl group, 9 -phenylanthracen-1-yl group, 9-phenylanthracen-2-yl group, 9-phenylanthracen-3-yl group, 9-phenylanthracen-4-yl group, 9-phenylanthracen-5-yl group, 9 -(2-pyridyl)-anthracen-10-yl group, 9-(3-pyridyl)-anthracen-10-yl group, 9-(4-pyridyl)-anthracen-10-yl group.

(8): 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 1-phenylpyren-2-yl group, 1-phenylpyren-3-yl group, 1-phenylpyren-4-yl group, 1 - phenylpyren-5-yl group, 1-phenylpyren-6-yl group, 1-phenylpyren-7-yl group, 1-phenylpyren-8-yl group, 1-phenylpyren-9-yl group, 1 - phenylpyren-10-yl group, 2-phenylpyren-1-yl group, 2-phenylpyren-3-yl group, 2-phenylpyren-4-yl group, 2-phenylpyren-5-yl group, 2 - phenylpyren-6-yl group, 2-phenylpyren-7-yl group, 2-phenylpyren-8-yl group, 2-phenylpyren-9-yl group, 2-phenylpyren-10-yl group, 9 -Phenylpyren-1-yl group, 9-phenylpyren-2-yl group, 9-phenylpyren-3-yl group, 9-phenylpyren-4-yl group, 9-phenylpyren-5-yl group, 9 -Phenylpyren-6-yl group, 9-phenylpyren-7-yl group, 9-phenylpyren-8-yl group, 9-phenylpyren-10-yl group, 1-methylpyren-2-yl group, 1- methylpyren-3-yl group, 1-methylpyren-4-yl group, 1-methylpyren-5-yl group, 1-methylpyren-6-yl group, 1-methylpyren-7-yl group, 1-methylpyren-8-yl group, 1-methylpyren-9-yl group, 1-methylpyren-10-yl group, 2-methylpyren-1-yl group, 2-methylpyren-3-yl group, 2-methylpyren-4-yl group, 2-methylpyrene -5-yl group, 2-methylpyren-6-yl group, 2-methylpyren-7-yl group, 2-methylpyren-8-yl group, 2-methylpyren-9-yl group, 2-methylpyren-10-yl group , 9-methylpyren-1-yl group, 9-methylpyren-2-yl group, 9-methylpyren-3-yl group, 9-methylpyren-4-yl group, 9-methylpyren-5-yl group, 9-methylpyren- 6-yl group, 9-methylpyren-7-yl group, 9-methylpyren-8-yl group, 9-methylpyren-10-yl group.

(9): fluoranthene-1-yl group, fluoranthene-1-yl group, fluoranthene-2-yl group, fluoranthene-3-yl group, fluoranthene-4-yl group, fluoranthene-5-yl group, fluoranthene-6- fluoranthene-7-yl group, fluoranthene-8-yl group, fluoranthene-9-yl group, fluoranthene-10-yl group;

(10): triphenylen-1-yl group, triphenylen-2-yl group, acenaphthylene-1-yl group, acenaphthylene-3-yl group, acenaphthylene-4-yl group, acenaphthylene-5-yl group, chrysene-1- yl group, chrysen-2-yl group, chrysen-5-yl group, chrysen-6-yl group;

(11): 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, quinoxalin-2-yl group, quinoxalin-5-yl group, quinoxalin-6-yl group, quinazolin-2-yl group, quinazolin-4-yl group, quinazolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-8-yl group, pyrazin-2-yl group, 5-methylpyrazine-2 -yl group, 5,6-diphenylpyrazin-2-yl group, pyrimidin-2-yl group, pyrimidin-4-yl group, pyrimidin-5-yl group, 2,4-diphenylpyrimidin-6-yl group, 4 , 6-diphenylpyrimidin-2-yl group, acridin-1-yl group, acridin-1-yl group, acridin-2-yl group, acridin-3-yl group, acridin-4-yl group, acridine-9- yl group, phenanthridin-1-yl group, phenanthridin-1-yl group, phenanthridin-2-yl group, phenanthridin-3-yl group, phenanthridin-4-yl group, phenanth lysin-6-yl group, phenanthridin-7-yl group, phenanthridin-8-yl group, phenanthridin-9-yl group, phenanthridin-10-yl group, phenazin-1-yl group, phenazin-2-yl 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]quinoline -10-yl group.

(12): 2-thienyl group, 3-thienyl group, 2-furyl group, 3-furyl group, benzothiophen-2-yl group, benzothiophen-3-yl group, benzothiophen-4-yl group, benzothiophene -5-yl group, benzothiophen-6-yl group, benzothiophen-7-yl group, benzofuran-2-yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group, benzofuran-6-yl group, benzofuran-7-yl group, dibenzothiophen-1-yl group, dibenzothiophen-2-yl group, dibenzothiophen-3-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, 3-methylthiophen-2-yl group, 4-methylthiophen-2-yl group, 5-methylthiophen-2-yl group, 2-methylthiophen-3-yl group, 4 -methylthiophen-3-yl group, 5-methylthiophen-3-yl group, 3-methylfuran-2-yl group, 4-methylfuran-2-yl group, 5-methylfuran-2-yl group, 2 -methylfuran-3-yl group, 4-methylfuran-3-yl group, 5-methylfuran-3-yl group.

(13): 3-methylbenzothiophen-2-yl group, 4-methylbenzothiophen-2-yl group, 5-methylbenzothiophen-2-yl group, 6-methylbenzothiophen-2-yl group, 7- methylbenzothiophen-2-yl group, 2-methylbenzothiophen-3-yl group, 4-methylbenzothiophen-3-yl group, 5-methylbenzothiophen-3-yl group, 6-methylbenzothiophene-3- yl group, 7-methylbenzothiophen-3-yl group, 2-methylbenzothiophen-4-yl group, 3-methylbenzothiophen-4-yl group, 5-methylbenzothiophen-4-yl group, 6-methyl benzothiophen-4-yl group, 7-methylbenzothiophen-4-yl group, 2-methylbenzothiophen-5-yl group, 3-methylbenzothiophen-5-yl group, 4-methylbenzothiophen-5-yl group, 6-methylbenzothiophen-5-yl group, 7-methylbenzothiophen-5-yl group, 2-methylbenzothiophen-6-yl group, 3-methylbenzothiophen-6-yl group, 4-methylbenzo thiophen-6-yl group, 5-methylbenzothiophen-6-yl group, 7-methylbenzothiophen-6-yl group, 2-methylbenzothiophen-7-yl group, 3-methylbenzothiophen-7-yl group , 4-methylbenzothiophen-7-yl group, 5-methylbenzothiophen-7-yl group, 6-methylbenzothiophen-7-yl group.

(14): 3-methylbenzofuran-2-yl group, 4-methylbenzofuran-2-yl group, 5-methylbenzofuran-2-yl group, 6-methylbenzofuran-2-yl group, 7-methylbenzofuran-2 -yl group, 2-methylbenzofuran-3-yl group, 4-methylbenzofuran-3-yl group, 5-methylbenzofuran-3-yl group, 6-methylbenzofuran-3-yl group, 7-methylbenzofuran-3 -yl group, 2-methylbenzofuran-4-yl group, 3-methylbenzofuran-4-yl group, 5-methylbenzofuran-4-yl group, 6-methylbenzofuran-4-yl group, 7-methylbenzofuran-4 -yl group, 2-methylbenzofuran-5-yl group, 3-methylbenzofuran-5-yl group, 4-methylbenzofuran-5-yl group, 6-methylbenzofuran-5-yl group, 7-methylbenzofuran-5 -yl group, 2-methylbenzofuran-6-yl group, 3-methylbenzofuran-6-yl group, 4-methylbenzofuran-6-yl group, 5-methylbenzofuran-6-yl group, 7-methylbenzofuran-6 -yl group, 2-methylbenzofuran-7-yl group, 3-methylbenzofuran-7-yl group, 4-methylbenzofuran-7-yl group, 5-methylbenzofuran-7-yl group, 6-methylbenzofuran-7 -yl group.

(15): 2-methyldibenzothiophen-1-yl group, 3-methyldibenzothiophen-1-yl group, 4-methyldibenzothiophen-1-yl group, 6-methyldibenzothiophen-1-yl group, 7- methyldibenzothiophen-1-yl group, 8-methyldibenzothiophen-1-yl group, 9-methyldibenzothiophen-1-yl group, 1-methyldibenzothiophen-2-yl group, 3-methyldibenzothiophene-2- yl group, 4-methyldibenzothiophen-2-yl group, 6-methyldibenzothiophen-2-yl group, 7-methyldibenzothiophen-2-yl group, 8-methyldibenzothiophen-2-yl group, 9-methyl Dibenzothiophen-2-yl group, 1-methyldibenzothiophen-3-yl group, 2-methyldibenzothiophen-3-yl group, 4-methyldibenzothiophen-3-yl group, 6-methyldibenzothiophen-3-yl 7-methyldibenzothiophen-3-yl group, 8-methyldibenzothiophen-3-yl group, 9-methyldibenzothiophen-3-yl group.

(16): 2-methyldibenzofuran-1-yl group, 3-methyldibenzofuran-1-yl group, 4-methyldibenzofuran-1-yl group, 6-methyldibenzofuran-1-yl group, 7-methyldibenzofuran-1 -yl group, 8-methyldibenzofuran-1-yl group, 9-methyldibenzofuran-1-yl group, 1-methyldibenzofuran-2-yl group, 3-methyldibenzofuran-2-yl group, 4-methyldibenzofuran-2 -yl group, 6-methyldibenzofuran-2-yl group, 7-methyldibenzofuran-2-yl group, 8-methyldibenzofuran-2-yl group, 9-methyldibenzofuran-2-yl group, 1-methyldibenzofuran-3 -yl group, 2-methyldibenzofuran-3-yl group, 4-methyldibenzofuran-3-yl group, 6-methyldibenzofuran-3-yl group, 7-methyldibenzofuran-3-yl group, 8-methyldibenzofuran-3 -yl group, 9-methyldibenzofuran-3-yl group.

(17): 3-phenylthiophen-2-yl group, 4-phenylthiophen-2-yl group, 5-phenylthiophen-2-yl group, 2-phenylthiophen-3-yl group, 4-phenylthiophene-3 -yl group, 5-phenylthiophen-3-yl group.

(18): 3-phenylfuran-2-yl group, 4-phenylfuran-2-yl group, 5-phenylfuran-2-yl group, 2-phenylfuran-3-yl group, 4-phenylfuran-3 -yl group, 5-phenylfuran-3-yl group.

(19): 3-phenylbenzothiophen-2-yl group, 4-phenylbenzothiophen-2-yl group, 5-phenylbenzothiophen-2-yl group, 6-phenylbenzothiophen-2-yl group, 7- Phenylbenzothiophen-2-yl group, 2-phenylbenzothiophen-3-yl group, 4-phenylbenzothiophen-3-yl group, 5-phenylbenzothiophen-3-yl group, 6-phenylbenzothiophene-3-yl group yl group, 7-phenylbenzothiophen-3-yl group, 2-phenylbenzothiophen-4-yl group, 3-phenylbenzothiophen-4-yl group, 5-phenylbenzothiophen-4-yl group, 6-phenyl benzothiophen-4-yl group, 7-phenylbenzothiophen-4-yl group, 2-phenylbenzothiophen-5-yl group, 3-phenylbenzothiophen-5-yl group, 4-phenylbenzothiophen-5-yl group, 6-phenylbenzothiophen-5-yl group, 7-phenylbenzothiophen-5-yl group, 2-phenylbenzothiophen-6-yl group, 3-phenylbenzothiophen-6-yl group, 4-phenylbenzo thiophen-6-yl group, 5-phenylbenzothiophen-6-yl group, 7-phenylbenzothiophen-6-yl group, 2-phenylbenzothiophen-7-yl group, 3-phenylbenzothiophen-7-yl group , 4-phenylbenzothiophen-7-yl group, 5-phenylbenzothiophen-7-yl group, 6-phenylbenzothiophen-7-yl group.

(20): 3-phenylbenzofuran-2-yl group, 4-phenylbenzofuran-2-yl group, 5-phenylbenzofuran-2-yl group, 6-phenylbenzofuran-2-yl group, 7-phenylbenzofuran-2 -yl group, 2-phenylbenzofuran-3-yl group, 4-phenylbenzofuran-3-yl group, 5-phenylbenzofuran-3-yl group, 6-phenylbenzofuran-3-yl group, 7-phenylbenzofuran-3 -yl group, 2-phenylbenzofuran-4-yl group, 3-phenylbenzofuran-4-yl group, 5-phenylbenzofuran-4-yl group, 6-phenylbenzofuran-4-yl group, 7-phenylbenzofuran-4 -yl group, 2-phenylbenzofuran-5-yl group, 3-phenylbenzofuran-5-yl group, 4-phenylbenzofuran-5-yl group, 6-phenylbenzofuran-5-yl group, 7-phenylbenzofuran-5 -yl group, 2-phenylbenzofuran-6-yl group, 3-phenylbenzofuran-6-yl group, 4-phenylbenzofuran-6-yl group, 5-phenylbenzofuran-6-yl group, 7-phenylbenzofuran-6 -yl group, 2-phenylbenzofuran-7-yl group, 3-phenylbenzofuran-7-yl group, 4-phenylbenzofuran-7-yl group, 5-phenylbenzofuran-7-yl group, 6-phenylbenzofuran-7 -yl group.

(21): 2-phenyldibenzothiophen-1-yl group, 3-phenyldibenzothiophen-1-yl group, 4-phenyldibenzothiophen-1-yl group, 6-phenyldibenzothiophen-1-yl group, 7- phenyldibenzothiophen-1-yl group, 8-phenyldibenzothiophen-1-yl group, 9-phenyldibenzothiophen-1-yl group, 1-phenyldibenzothiophen-2-yl group, 3-phenyldibenzothiophene-2- yl group, 4-phenyldibenzothiophen-2-yl group, 6-phenyldibenzothiophen-2-yl group, 7-phenyldibenzothiophen-2-yl group, 8-phenyldibenzothiophen-2-yl group, 9-phenyl Dibenzothiophen-2-yl group, 1-phenyldibenzothiophen-3-yl group, 2-phenyldibenzothiophen-3-yl group, 4-phenyldibenzothiophen-3-yl group, 6-phenyldibenzothiophen-3-yl 7-phenyldibenzothiophen-3-yl group, 8-phenyldibenzothiophen-3-yl group, 9-phenyldibenzothiophen-3-yl group.

(22): 2-phenyldibenzofuran-1-yl group, 3-phenyldibenzofuran-1-yl group, 4-phenyldibenzofuran-1-yl group, 6-phenyldibenzofuran-1-yl group, 7-phenyldibenzofuran-1 -yl group, 8-phenyldibenzofuran-1-yl group, 9-phenyldibenzofuran-1-yl group, 1-phenyldibenzofuran-2-yl group, 3-phenyldibenzofuran-2-yl group, 4-phenyldibenzofuran-2 -yl group, 6-phenyldibenzofuran-2-yl group, 7-phenyldibenzofuran-2-yl group, 8-phenyldibenzofuran-2-yl group, 9-phenyldibenzofuran-2-yl group, 1-phenyldibenzofuran-3 -yl group, 2-phenyldibenzofuran-3-yl group, 4-phenyldibenzofuran-3-yl group, 6-phenyldibenzofuran-3-yl group, 7-phenyldibenzofuran-3-yl group, 8-phenyldibenzofuran-3 -yl group, 9-phenyldibenzofuran-3-yl group.

(23): 3-(2-pyridyl)thiophen-2-yl group, 4-(2-pyridyl)thiophen-2-yl group, 5-(2-pyridyl)thiophen-2-yl group, 2-(2 -pyridyl)thiophen-3-yl group, 4-(2-pyridyl)thiophen-3-yl group, 5-(2-pyridyl)thiophen-3-yl group, 3-(2-pyridyl)furan-2-yl group, 4-(2-pyridyl)furan-2-yl group, 5-(2-pyridyl)furan-2-yl group, 2-(2-pyridyl)furan-3-yl group, 4-(2-pyridyl ) furan-3-yl group, 5-(2-pyridyl)furan-3-yl group.

(24): 3-(2-pyridyl)benzothiophen-2-yl group, 4-(2-pyridyl)benzothiophen-2-yl group, 5-(2-pyridyl)benzothiophen-2-yl group, 6 -(2-pyridyl)benzothiophen-2-yl group, 7-(2-pyridyl)benzothiophen-2-yl group, 2-(2-pyridyl)benzothiophen-3-yl group, 4-(2-pyridyl) ) benzothiophen-3-yl group, 5-(2-pyridyl)benzothiophen-3-yl group, 6-(2-pyridyl)benzothiophen-3-yl group, 7-(2-pyridyl)benzothiophene-3 -yl group, 2-(2-pyridyl)benzothiophen-4-yl group, 3-(2-pyridyl)benzothiophen-4-yl group, 5-(2-pyridyl)benzothiophen-4-yl group, 6 -(2-pyridyl)benzothiophen-4-yl group, 7-(2-pyridyl)benzothiophen-4-yl group, 2-(2-pyridyl)benzothiophen-5-yl group, 3-(2-pyridyl) ) benzothiophen-5-yl group, 4-(2-pyridyl)benzothiophen-5-yl group, 6-(2-pyridyl)benzothiophen-5-yl group, 7-(2-pyridyl)benzothiophene-5 -yl group, 2-(2-pyridyl)benzothiophen-6-yl group, 3-(2-pyridyl)benzothiophen-6-yl group, 4-(2-pyridyl)benzothiophen-6-yl group, 5 -(2-pyridyl)benzothiophen-6-yl group, 7-(2-pyridyl)benzothiophen-6-yl group, 2-(2-pyridyl)benzothiophen-7-yl group, 3-(2-pyridyl) ) benzothiophen-7-yl group, 4-(2-pyridyl)benzothiophen-7-yl group, 5-(2-pyridyl)benzothiophen-7-yl group, 6-(2-pyridyl)benzothiophene-7 -yl group.

(25): 3-(2-pyridyl)benzofuran-2-yl group, 4-(2-pyridyl)benzofuran-2-yl group, 5-(2-pyridyl)benzofuran-2-yl group, 6-(2 -pyridyl)benzofuran-2-yl group, 7-(2-pyridyl)benzofuran-2-yl group, 2-(2-pyridyl)benzofuran-3-yl group, 4-(2-pyridyl)benzofuran-3-yl group, 5-(2-pyridyl)benzofuran-3-yl group, 6-(2-pyridyl)benzofuran-3-yl group, 7-(2-pyridyl)benzofuran-3-yl group, 2-(2-pyridyl ) benzofuran-4-yl group, 3-(2-pyridyl)benzofuran-4-yl group, 5-(2-pyridyl)benzofuran-4-yl group, 6-(2-pyridyl)benzofuran-4-yl group, 7-(2-pyridyl)benzofuran-4-yl group, 2-(2-pyridyl)benzofuran-5-yl group, 3-(2-pyridyl)benzofuran-5-yl group, 4-(2-pyridyl)benzofuran -5-yl group, 6-(2-pyridyl)benzofuran-5-yl group, 7-(2-pyridyl)benzofuran-5-yl group, 2-(2-pyridyl)benzofuran-6-yl group, 3- (2-pyridyl)benzofuran-6-yl group, 4-(2-pyridyl)benzofuran-6-yl group, 5-(2-pyridyl)benzofuran-6-yl group, 7-(2-pyridyl)benzofuran-6 -yl group, 2-(2-pyridyl)benzofuran-7-yl group, 3-(2-pyridyl)benzofuran-7-yl group, 4-(2-pyridyl)benzofuran-7-yl group, 5-(2 -pyridyl)benzofuran-7-yl group, 6-(2-pyridyl)benzofuran-7-yl group.

(26): 2-(2-pyridyl)dibenzothiophen-1-yl group, 3-(2-pyridyl)dibenzothiophen-1-yl group, 4-(2-pyridyl)dibenzothiophen-1-yl group, 6 -(2-pyridyl) dibenzothiophen-1-yl group, 7-(2-pyridyl) dibenzothiophen-1-yl group, 8-(2-pyridyl) dibenzothiophen-1-yl group, 9-(2-pyridyl) ) dibenzothiophen-1-yl group, 1-(2-pyridyl) dibenzothiophen-2-yl group, 3-(2-pyridyl) dibenzothiophen-2-yl group, 4-(2-pyridyl) dibenzothiophene-2 -yl group, 6-(2-pyridyl)dibenzothiophen-2-yl group, 7-(2-pyridyl)dibenzothiophen-2-yl group, 8-(2-pyridyl)dibenzothiophen-2-yl group, 9 -(2-pyridyl) dibenzothiophen-2-yl group, 1-(2-pyridyl) dibenzothiophen-3-yl group, 2-(2-pyridyl) dibenzothiophen-3-yl group, 4-(2-pyridyl) ) dibenzothiophen-3-yl group, 6-(2-pyridyl) dibenzothiophen-3-yl group, 7-(2-pyridyl) dibenzothiophen-3-yl group, 8-(2-pyridyl) dibenzothiophene-3 -yl group, 9-(2-pyridyl)dibenzothiophen-3-yl group.

(27): 2-(2-pyridyl) dibenzofuran-1-yl group, 3-(2-pyridyl) dibenzofuran-1-yl group, 4-(2-pyridyl) dibenzofuran-1-yl group, 6-(2 -pyridyl)dibenzofuran-1-yl group, 7-(2-pyridyl)dibenzofuran-1-yl group, 8-(2-pyridyl)dibenzofuran-1-yl group, 9-(2-pyridyl)dibenzofuran-1-yl group, 1-(2-pyridyl) dibenzofuran-2-yl group, 3-(2-pyridyl) dibenzofuran-2-yl group, 4-(2-pyridyl) dibenzofuran-2-yl group, 6-(2-pyridyl ) dibenzofuran-2-yl group, 7-(2-pyridyl)dibenzofuran-2-yl group, 8-(2-pyridyl)dibenzofuran-2-yl group, 9-(2-pyridyl)dibenzofuran-2-yl group, 1-(2-pyridyl)dibenzofuran-3-yl group, 2-(2-pyridyl)dibenzofuran-3-yl group, 4-(2-pyridyl)dibenzofuran-3-yl group, 6-(2-pyridyl)dibenzofuran -3-yl group, 7-(2-pyridyl)dibenzofuran-3-yl group, 8-(2-pyridyl)dibenzofuran-3-yl group, 9-(2-pyridyl)dibenzofuran-3-yl group.

(28): 3-(3-pyridyl)thiophen-2-yl group, 4-(3-pyridyl)thiophen-2-yl group, 5-(3-pyridyl)thiophen-2-yl group, 2-(3 -pyridyl)thiophen-3-yl group, 4-(3-pyridyl)thiophen-3-yl group, 5-(3-pyridyl)thiophen-3-yl group.

(29): 3-(3-pyridyl) furan-2-yl group, 4-(3-pyridyl) furan-2-yl group, 5-(3-pyridyl) furan-2-yl group, 2-(3 -pyridyl)furan-3-yl group, 4-(3-pyridyl)furan-3-yl group, 5-(3-pyridyl)furan-3-yl group.

(30): 3-(3-pyridyl)benzothiophen-2-yl group, 4-(3-pyridyl)benzothiophen-2-yl group, 5-(3-pyridyl)benzothiophen-2-yl group, 6 -(3-pyridyl)benzothiophen-2-yl group, 7-(3-pyridyl)benzothiophen-2-yl group, 2-(3-pyridyl)benzothiophen-3-yl group, 4-(3-pyridyl) ) benzothiophen-3-yl group, 5-(3-pyridyl)benzothiophen-3-yl group, 6-(3-pyridyl)benzothiophen-3-yl group, 7-(3-pyridyl)benzothiophene-3 -yl group, 2-(3-pyridyl)benzothiophen-4-yl group, 3-(3-pyridyl)benzothiophen-4-yl group, 5-(3-pyridyl)benzothiophen-4-yl group, 6 -(3-pyridyl)benzothiophen-4-yl group, 7-(3-pyridyl)benzothiophen-4-yl group, 2-(3-pyridyl)benzothiophen-5-yl group, 3-(3-pyridyl) ) benzothiophen-5-yl group, 4-(3-pyridyl)benzothiophen-5-yl group, 6-(3-pyridyl)benzothiophen-5-yl group, 7-(3-pyridyl)benzothiophene-5 -yl group, 2-(3-pyridyl)benzothiophen-6-yl group, 3-(3-pyridyl)benzothiophen-6-yl group, 4-(3-pyridyl)benzothiophen-6-yl group, 5 -(3-pyridyl)benzothiophen-6-yl group, 7-(3-pyridyl)benzothiophen-6-yl group, 2-(3-pyridyl)benzothiophen-7-yl group, 3-(3-pyridyl) ) benzothiophen-7-yl group, 4-(3-pyridyl)benzothiophen-7-yl group, 5-(3-pyridyl)benzothiophen-7-yl group, 6-(3-pyridyl)benzothiophene-7 -yl group.

(31): 3-(3-pyridyl)benzofuran-2-yl group, 4-(3-pyridyl)benzofuran-2-yl group, 5-(3-pyridyl)benzofuran-2-yl group, 6-(3 -pyridyl)benzofuran-2-yl group, 7-(3-pyridyl)benzofuran-2-yl group, 2-(3-pyridyl)benzofuran-3-yl group, 4-(3-pyridyl)benzofuran-3-yl group, 5-(3-pyridyl)benzofuran-3-yl group, 6-(3-pyridyl)benzofuran-3-yl group, 7-(3-pyridyl)benzofuran-3-yl group, 2-(3-pyridyl ) benzofuran-4-yl group, 3-(3-pyridyl)benzofuran-4-yl group, 5-(3-pyridyl)benzofuran-4-yl group, 6-(3-pyridyl)benzofuran-4-yl group, 7-(3-pyridyl)benzofuran-4-yl group, 2-(3-pyridyl)benzofuran-5-yl group, 3-(3-pyridyl)benzofuran-5-yl group, 4-(3-pyridyl)benzofuran -5-yl group, 6-(3-pyridyl)benzofuran-5-yl group, 7-(3-pyridyl)benzofuran-5-yl group, 2-(3-pyridyl)benzofuran-6-yl group, 3- (3-pyridyl)benzofuran-6-yl group, 4-(3-pyridyl)benzofuran-6-yl group, 5-(3-pyridyl)benzofuran-6-yl group, 7-(3-pyridyl)benzofuran-6 -yl group, 2-(3-pyridyl)benzofuran-7-yl group, 3-(3-pyridyl)benzofuran-7-yl group, 4-(3-pyridyl)benzofuran-7-yl group, 5-(3 -pyridyl)benzofuran-7-yl group, 6-(3-pyridyl)benzofuran-7-yl group.

(32): 2-(3-pyridyl)dibenzothiophen-1-yl group, 3-(3-pyridyl)dibenzothiophen-1-yl group, 4-(3-pyridyl)dibenzothiophen-1-yl group, 6 -(3-pyridyl) dibenzothiophen-1-yl group, 7-(3-pyridyl) dibenzothiophen-1-yl group, 8-(3-pyridyl) dibenzothiophen-1-yl group, 9-(3-pyridyl ) dibenzothiophen-1-yl group, 1-(3-pyridyl) dibenzothiophen-2-yl group, 3-(3-pyridyl) dibenzothiophen-2-yl group, 4-(3-pyridyl) dibenzothiophene-2 -yl group, 6-(3-pyridyl)dibenzothiophen-2-yl group, 7-(3-pyridyl)dibenzothiophen-2-yl group, 8-(3-pyridyl)dibenzothiophen-2-yl group, 9 -(3-pyridyl) dibenzothiophen-2-yl group, 1-(3-pyridyl) dibenzothiophen-3-yl group, 2-(3-pyridyl) dibenzothiophen-3-yl group, 4-(3-pyridyl) ) dibenzothiophen-3-yl group, 6-(3-pyridyl) dibenzothiophen-3-yl group, 7-(3-pyridyl) dibenzothiophen-3-yl group, 8-(3-pyridyl) dibenzothiophene-3 -yl group, 9-(3-pyridyl)dibenzothiophen-3-yl group.

(33): 2-(3-pyridyl) dibenzofuran-1-yl group, 3-(3-pyridyl) dibenzofuran-1-yl group, 4-(3-pyridyl) dibenzofuran-1-yl group, 6-(3 -pyridyl)dibenzofuran-1-yl group, 7-(3-pyridyl)dibenzofuran-1-yl group, 8-(3-pyridyl)dibenzofuran-1-yl group, 9-(3-pyridyl)dibenzofuran-1-yl group, 1-(3-pyridyl) dibenzofuran-2-yl group, 3-(3-pyridyl) dibenzofuran-2-yl group, 4-(3-pyridyl) dibenzofuran-2-yl group, 6-(3-pyridyl ) dibenzofuran-2-yl group, 7-(3-pyridyl)dibenzofuran-2-yl group, 8-(3-pyridyl)dibenzofuran-2-yl group, 9-(3-pyridyl)dibenzofuran-2-yl group, 1-(3-pyridyl)dibenzofuran-3-yl group, 2-(3-pyridyl)dibenzofuran-3-yl group, 4-(3-pyridyl)dibenzofuran-3-yl group, 6-(3-pyridyl)dibenzofuran -3-yl group, 7-(3-pyridyl)dibenzofuran-3-yl group, 8-(3-pyridyl)dibenzofuran-3-yl group, 9-(3-pyridyl)dibenzofuran-3-yl group.

(34): 3-(4-pyridyl)thiophen-2-yl group, 4-(4-pyridyl)thiophen-2-yl group, 5-(4-pyridyl)thiophen-2-yl group, 2-(4 -pyridyl)thiophen-3-yl group, 4-(4-pyridyl)thiophen-3-yl group, 5-(4-pyridyl)thiophen-3-yl group.

(35): 3-(4-pyridyl)furan-2-yl group, 4-(4-pyridyl)furan-2-yl group, 5-(4-pyridyl)furan-2-yl group, 2-(4 -pyridyl)furan-3-yl group, 4-(4-pyridyl)furan-3-yl group, 5-(4-pyridyl)furan-3-yl group.

(36): 3-(4-pyridyl)benzothiophen-2-yl group, 4-(4-pyridyl)benzothiophen-2-yl group, 5-(4-pyridyl)benzothiophen-2-yl group, 6 -(4-pyridyl)benzothiophen-2-yl group, 7-(4-pyridyl)benzothiophen-2-yl group, 2-(4-pyridyl)benzothiophen-3-yl group, 4-(4-pyridyl) ) benzothiophen-3-yl group, 5-(4-pyridyl)benzothiophen-3-yl group, 6-(4-pyridyl)benzothiophen-3-yl group, 7-(4-pyridyl)benzothiophene-3 -yl group, 2-(4-pyridyl)benzothiophen-4-yl group, 3-(4-pyridyl)benzothiophen-4-yl group, 5-(4-pyridyl)benzothiophen-4-yl group, 6 -(4-pyridyl)benzothiophen-4-yl group, 7-(4-pyridyl)benzothiophen-4-yl group, 2-(4-pyridyl)benzothiophen-5-yl group, 3-(4-pyridyl) ) benzothiophen-5-yl group, 4-(4-pyridyl)benzothiophen-5-yl group, 6-(4-pyridyl)benzothiophen-5-yl group, 7-(4-pyridyl)benzothiophene-5 -yl group, 2-(4-pyridyl)benzothiophen-6-yl group, 3-(4-pyridyl)benzothiophen-6-yl group, 4-(4-pyridyl)benzothiophen-6-yl group, 5 -(4-pyridyl)benzothiophen-6-yl group, 7-(4-pyridyl)benzothiophen-6-yl group, 2-(4-pyridyl)benzothiophen-7-yl group, 3-(4-pyridyl) ) benzothiophen-7-yl group, 4-(4-pyridyl)benzothiophen-7-yl group, 5-(4-pyridyl)benzothiophen-7-yl group, 6-(4-pyridyl)benzothiophene-7 -yl group.

(37): 3-(4-pyridyl)benzofuran-2-yl group, 4-(4-pyridyl)benzofuran-2-yl group, 5-(4-pyridyl)benzofuran-2-yl group, 6-(4 -pyridyl)benzofuran-2-yl group, 7-(4-pyridyl)benzofuran-2-yl group, 2-(4-pyridyl)benzofuran-3-yl group, 4-(4-pyridyl)benzofuran-3-yl group, 5-(4-pyridyl)benzofuran-3-yl group, 6-(4-pyridyl)benzofuran-3-yl group, 7-(4-pyridyl)benzofuran-3-yl group, 2-(4-pyridyl ) benzofuran-4-yl group, 3-(4-pyridyl)benzofuran-4-yl group, 5-(4-pyridyl)benzofuran-4-yl group, 6-(4-pyridyl)benzofuran-4-yl group, 7-(4-pyridyl)benzofuran-4-yl group, 2-(4-pyridyl)benzofuran-5-yl group, 3-(4-pyridyl)benzofuran-5-yl group, 4-(4-pyridyl)benzofuran -5-yl group, 6-(4-pyridyl)benzofuran-5-yl group, 7-(4-pyridyl)benzofuran-5-yl group, 2-(4-pyridyl)benzofuran-6-yl group, 3- (4-pyridyl)benzofuran-6-yl group, 4-(4-pyridyl)benzofuran-6-yl group, 5-(4-pyridyl)benzofuran-6-yl group, 7-(4-pyridyl)benzofuran-6 -yl group, 2-(4-pyridyl)benzofuran-7-yl group, 3-(4-pyridyl)benzofuran-7-yl group, 4-(4-pyridyl)benzofuran-7-yl group, 5-(4 -pyridyl)benzofuran-7-yl group, 6-(4-pyridyl)benzofuran-7-yl group.

(38): 2-(4-pyridyl)dibenzothiophen-1-yl group, 3-(4-pyridyl)dibenzothiophen-1-yl group, 4-(4-pyridyl)dibenzothiophen-1-yl group, 6 -(4-pyridyl) dibenzothiophen-1-yl group, 7-(4-pyridyl) dibenzothiophen-1-yl group, 8-(4-pyridyl) dibenzothiophen-1-yl group, 9-(4-pyridyl ) dibenzothiophen-1-yl group, 1-(4-pyridyl) dibenzothiophen-2-yl group, 3-(4-pyridyl) dibenzothiophen-2-yl group, 4-(4-pyridyl) dibenzothiophene-2 -yl group, 6-(4-pyridyl)dibenzothiophen-2-yl group, 7-(4-pyridyl)dibenzothiophen-2-yl group, 8-(4-pyridyl)dibenzothiophen-2-yl group, 9 -(4-pyridyl) dibenzothiophen-2-yl group, 1-(4-pyridyl) dibenzothiophen-3-yl group, 2-(4-pyridyl) dibenzothiophen-3-yl group, 4-(4-pyridyl) ) dibenzothiophen-3-yl group, 6-(4-pyridyl) dibenzothiophen-3-yl group, 7-(4-pyridyl) dibenzothiophen-3-yl group, 8-(4-pyridyl) dibenzothiophene-3 -yl group, 9-(4-pyridyl)dibenzothiophen-3-yl group.

(39): 2-(4-pyridyl)dibenzofuran-1-yl group, 3-(4-pyridyl)dibenzofuran-1-yl group, 4-(4-pyridyl)dibenzofuran-1-yl group, 6-(4 -pyridyl)dibenzofuran-1-yl group, 7-(4-pyridyl)dibenzofuran-1-yl group, 8-(4-pyridyl)dibenzofuran-1-yl group, 9-(4-pyridyl)dibenzofuran-1-yl group, 1-(4-pyridyl) dibenzofuran-2-yl group, 3-(4-pyridyl) dibenzofuran-2-yl group, 4-(4-pyridyl) dibenzofuran-2-yl group, 6-(4-pyridyl ) dibenzofuran-2-yl group, 7-(4-pyridyl)dibenzofuran-2-yl group, 8-(4-pyridyl)dibenzofuran-2-yl group, 9-(4-pyridyl)dibenzofuran-2-yl group, 1-(4-pyridyl)dibenzofuran-3-yl group, 2-(4-pyridyl)dibenzofuran-3-yl group, 4-(4-pyridyl)dibenzofuran-3-yl group, 6-(4-pyridyl)dibenzofuran -3-yl group, 7-(4-pyridyl)dibenzofuran-3-yl group, 8-(4-pyridyl)dibenzofuran-3-yl group, 9-(4-pyridyl)dibenzofuran-3-yl group.

(40): 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl 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, 9,9-diphenylfluoren-1-yl group, 9,9-diphenylfluoren-2-yl group, 9,9- diphenylfluoren-3-yl group, 9,9-diphenylfluoren-4-yl group;

(41): 2-(1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 4-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl) ) phenyl group, 4-(2-naphthyl)phenyl group, 2-(9-phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(1-anthryl ) phenyl group, 3-(1-anthryl)phenyl group, 4-(1-anthryl)phenyl group, 2-(2-anthryl)phenyl group, 3-(2-anthryl)phenyl group, 4-(2-anthryl) ) phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 4-(9-anthryl)phenyl group, 2-(1-pyrenyl)phenyl group, 3-(1-pyrenyl ) phenyl group, 4-(1-pyrenyl)phenyl group, 2-(2-pyrenyl)phenyl group, 3-(2-pyrenyl)phenyl group, 4-(2-pyrenyl)phenyl group, 2-(2-fur olanthenyl)phenyl group, 3-(2-fluoranthenyl)phenyl group, 4-(2-fluoranthenyl)phenyl group, 2-(3-fluoranthenyl)phenyl group, 3-(3-fluoranthenyl) ) phenyl group, 4-(3-fluoranthenyl)phenyl group, 2-(7-fluoranthenyl)phenyl group, 3-(7-fluoranthenyl)phenyl group, 4-(7-fluoranthenyl)phenyl group, 2-(8-fluoranthenyl)phenyl group, 3-(8-fluoranthenyl)phenyl group, 4-(8-fluoranthenyl)phenyl group, 2-(1-triphenylenyl)phenyl group, 3- (1-triphenylenyl)phenyl group, 4-(1-triphenylenyl)phenyl group, 2-(2-triphenylenyl)phenyl group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group.

(42): 2-(2-quinolyl)phenyl group, 3-(2-quinolyl)phenyl group, 4-(2-quinolyl)phenyl group, 2-(3-quinolyl)phenyl group, 3-(3-quinolyl) ) phenyl group, 4-(3-quinolyl)phenyl group, 2-(4-quinolyl)phenyl group, 3-(4-quinolyl)phenyl group, 4-(4-quinolyl)phenyl group, 2-(5-quinolyl) ) phenyl group, 3-(5-quinolyl)phenyl group, 4-(5-quinolyl)phenyl group, 2-(6-quinolyl)phenyl group, 3-(6-quinolyl)phenyl group, 4-(6-quinolyl) ) phenyl group, 2-(7-quinolyl)phenyl group, 3-(7-quinolyl)phenyl group, 4-(7-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl) ) phenyl group, 4-(8-quinolyl)phenyl group, 2-(1-isoquinolyl)phenyl group, 3-(1-isoquinolyl)phenyl group, 4-(1-isoquinolyl)phenyl group, 2-(3-isoquinolyl) ) phenyl group, 3-(3-isoquinolyl)phenyl group, 4-(3-isoquinolyl)phenyl group, 2-(4-isoquinolyl)phenyl group, 3-(4-isoquinolyl)phenyl group, 4-(4-isoquinolyl) ) phenyl group, 2-(5-isoquinolyl)phenyl group, 3-(5-isoquinolyl)phenyl group, 4-(5-isoquinolyl)phenyl group, 2-(6-isoquinolyl)phenyl group, 3-(6-isoquinolyl) ) phenyl group, 4-(6-isoquinolyl)phenyl group, 2-(7-isoquinolyl)phenyl group, 3-(7-isoquinolyl)phenyl group, 4-(7-isoquinolyl)phenyl group, 2-(8-isoquinolyl) ) phenyl group, 3-(8-isoquinolyl)phenyl group, 4-(8-isoquinolyl)phenyl group.

(43): 2-(2-benzothienyl)phenyl group, 3-(2-benzothienyl)phenyl group, 4-(2-benzothienyl)phenyl group, 2-(3-benzothienyl)phenyl group, 3- (3-benzothienyl) phenyl group, 4-(3-benzothienyl) phenyl group, 2-(4-benzothienyl) phenyl group, 3-(4-benzothienyl) phenyl group, 4-(4-benzothienyl) Phenyl group, 2-(5-benzothienyl) phenyl group, 3-(5-benzothienyl) phenyl group, 4-(5-benzothienyl) phenyl group, 2-(6-benzothienyl) phenyl group, 3-( 6-benzothienyl)phenyl group, 4-(6-benzothienyl)phenyl group, 2-(7-benzothienyl)phenyl group, 3-(7-benzothienyl)phenyl group, 4-(7-benzothienyl)phenyl group, 2-(2-benzofuryl)phenyl group, 3-(2-benzofuryl)phenyl group, 4-(2-benzofuryl)phenyl group, 2-(3-benzofuryl)phenyl group, 3-(3-benzofuryl)phenyl group, 4-(3-benzofuryl)phenyl group, 2-(4-benzofuryl)phenyl group, 3-(4-benzofuryl)phenyl group, 4-(4-benzofuryl)phenyl group, 2-(5-benzofuryl)phenyl group, 3-(5-benzofuryl)phenyl group, 4-(5-benzofuryl)phenyl group, 2-(6-benzofuryl)phenyl group, 3-(6-benzofuryl)phenyl group, 4-(6-benzofuryl)phenyl 2-(7-benzofuryl)phenyl group, 3-(7-benzofuryl)phenyl group, 4-(7-benzofuryl)phenyl group.

(44): 2-(1-dibenzothienyl)phenyl group, 3-(1-dibenzothienyl)phenyl group, 4-(1-dibenzothienyl)phenyl group, 2-(2-dibenzothienyl)phenyl group, 3- (2-dibenzothienyl) phenyl group, 4-(2-dibenzothienyl) phenyl group, 2-(3-dibenzothienyl) phenyl group, 3-(3-dibenzothienyl) phenyl group, 4-(3-dibenzothienyl) Phenyl group, 2-(4-dibenzothienyl) phenyl group, 3-(4-dibenzothienyl) phenyl group, 4-(4-dibenzothienyl) phenyl group, 2-(1-dibenzofuryl) phenyl group, 3-( 1-dibenzofuryl)phenyl group, 4-(1-dibenzofuryl)phenyl group, 2-(2-dibenzofuryl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 2-(3-dibenzofuryl)phenyl group, 3-(3-dibenzofuryl)phenyl group, 4-(3-dibenzofuryl)phenyl group, 2-(4-dibenzofuryl)phenyl group, 3-(4 -dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group.

Among these substituents, phenyl group, p-tolyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 2-(2 -pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3 -pyridyl)phenyl group, 2-(4-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 2-(1-naphthyl)phenyl group, 3-(1 -naphthyl)phenyl group, 4-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 2-(9 -phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 4-(9 -anthryl)phenyl group, 2-(3-fluoranthenyl)phenyl group, 3-(3-fluoranthenyl)phenyl group, 4-(3-fluoranthenyl)phenyl group, 2-(2-triphenylenyl)phenyl group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group, 2-(3-quinolyl)phenyl group, 3-(3-quinolyl)phenyl group, 4-(3-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(2-dibenzothienyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 2-(4- dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 2-(2-dibenzofuryl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 2-(4-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 2-pyridyl group, 3 -pyridyl group, 4-pyridyl group, 1-naphthyl group, 2-naphthyl group, 3-quinolyl group, 4-quinolyl group, 8-quinolyl group, 3-isoquinolyl group, 2-ben zothienyl group, 2-benzofuryl group, 9-anthryl group, 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, 4-dibenzofuryl group, 3-fluoranthenyl group, 1 -pyrenyl group, 2-triphenylenyl group and the like are preferred. Further, among these substituents, phenyl group, p-tolyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3- (2-pyridyl) phenyl group, 4-(2-pyridyl) phenyl group, 3-(3-pyridyl) phenyl group, 4-(3-pyridyl) phenyl group, 3-(4-pyridyl) phenyl group, 4- (4-pyridyl) phenyl group, 2-(1-naphthyl) phenyl group, 3-(1-naphthyl) phenyl group, 2-(2-naphthyl) phenyl group, 3-(2-naphthyl) phenyl group, 4- (2-naphthyl) phenyl group, 3-(9-phenanthryl) phenyl group, 4-(9-phenanthryl) phenyl group, 2-(9-anthryl) phenyl group, 3-(9-anthryl) phenyl group, 3- (3-fluoranthenyl)phenyl group, 4-(3-fluoranthenyl)phenyl group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group, 3-(3-quinolyl)phenyl group, 4-(3-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4- dibenzothienyl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 1-naphthyl group, 2-naphthyl group, 3-quinolyl group, 8-quinolyl group, 2-benzothienyl group, 2-benzofuryl group, 9-anthryl group , 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group and 4-dibenzofuryl group are more preferred.

The total number of ring-constituting carbon atoms of the group represented by Ar ² and the total number of ring-constituting carbon atoms of the group represented by Ar ³ are both 4-25. The total number of ring-constituting carbon atoms of the group represented by Ar ² and the total number of ring-constituting carbon atoms of Ar ³ are both preferably 4-20.
When Ar ² and Ar ³ have a substituent, the number of carbon atoms of the substituent is not included in the total number of ring-constituting carbon atoms of the groups represented by Ar ² and Ar ³ . Therefore, for example, when the group represented by Ar ² is a diphenylfluorene group (having 25 ring-constituting carbon atoms) and the group represented by Ar ¹ has a phenyl group, the diphenylfluorene group having a phenyl group can The group +Ar ² ) will have 31 ring carbon atoms in total.

The sum of the total number of ring-constituting carbon atoms of Ar ² and the total number of ring-constituting carbon atoms of Ar ³ is preferably 8-32.

[Regarding Z ¹ and Z ² ]
One of Z ¹ and Z ² represents a nitrogen atom and the other represents C—H.

[Regarding A, B ¹ and B ² ]
A forms a single bond with B ¹ or B ² ;
one of B ¹ and B ² forms a single bond with A and the other represents a hydrogen atom;

When the cyclic azine compound (1) is used as a constituent component of an organic light emitting diode (OLED), effects such as high current efficiency and long life can be obtained. In particular, these effects are exhibited even more when the cyclic azine compound (1) is used as the electron transport layer.

[Specific examples of cyclic azine compound (1)]
Preferred compounds A-1 to A-405 are exemplified below as the cyclic azine compound represented by formula (1), but the cyclic azine compound is not limited to these compounds.

Applications of the cyclic azine compound (1) are described below.
<Material for Organic Electroluminescent Device, Electron Transport Material for Organic Electroluminescent Device>
Although the cyclic azine compound (1) is not particularly limited, it can be used, for example, as a material for organic electroluminescence devices. Moreover, the cyclic azine compound (1) can be used, for example, as an electron-transporting material for an organic electroluminescence device.
That is, the material for an organic electroluminescence device according to one aspect of the present invention contains the cyclic azine compound (1). Further, an electron transport material for an organic electroluminescent device according to one aspect of the present invention contains a cyclic azine compound (1). The organic electroluminescence device material and the electron transport material for organic electroluminescence device containing the cyclic azine compound (1) contribute to the production of an organic electroluminescence device excellent in durability and current efficiency.

<Organic electroluminescent device>
An organic electroluminescent device according to one aspect of the present invention contains a cyclic azine compound (1).
The structure of the organic electroluminescence device is not particularly limited, but includes, for example, the following structures (i) to (vi).
(i): anode/light 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 (vi): anode/hole injection layer/charge generation layer /hole transport layer/light emitting layer/electron transport layer/cathode

Hereinafter, the organic electroluminescence device according to one embodiment of the present invention will be described in more detail with reference to FIG. 1, taking the configuration (vi) above as an example. FIG. 1 is a schematic cross-sectional view showing an example of a lamination structure of an organic electroluminescence device containing a cyclic azine compound according to one embodiment of the present invention.
The organic electroluminescence element shown in FIG. 1 has a so-called bottom emission type element configuration, but the organic electroluminescence element according to one aspect of the present invention is limited to the bottom emission type element configuration. is not. That is, the organic electroluminescence element according to one aspect of the present invention may have a top emission type element configuration, or may have another known element configuration.

The organic electroluminescent device 100 comprises a substrate 1, an anode 2, a hole injection layer 3, a charge generation layer 4, a hole transport layer 5, a light emitting layer 6, an electron transport layer 7 and a cathode 8 in this order. However, some of these layers may be omitted, or conversely, other layers may be added. For example, an electron injection layer may be provided between the electron transport layer 7 and the cathode 8, the charge generation layer 4 may be omitted, and the hole transport layer 5 may be provided directly on the hole injection layer 3. good too. Further, a single layer having the functions of a plurality of layers, such as an electron injection/transport layer having both the function of an electron injection layer and the function of an electron transport layer in a single layer. It may be a configuration provided instead of. Further, for example, the single-layer hole transport layer 5 and the single-layer electron transport layer 7 may each consist of a plurality of layers.

[Layer containing cyclic azine compound represented by formula (1)]
The organic electroluminescent device contains the cyclic azine compound represented by the above formula (1) in one or more layers selected from the group consisting of the light-emitting layer and layers between the light-emitting layer and the cathode. Therefore, in the configuration example shown in FIG. 1, the organic electroluminescence device 100 contains the cyclic azine compound (1) in at least one layer selected from the group consisting of the light emitting layer 6 and the electron transport layer 7 . In particular, the electron transport layer 7 preferably contains the cyclic azine compound (1). The cyclic azine compound (1) may be contained in a plurality of layers included in the organic electroluminescent device, and when an electron injection layer is provided between the electron transport layer and the cathode, the electron injection layer is It may contain a cyclic azine compound (1).
In addition, the organic electroluminescence device 100 in which the electron transport layer 7 contains the cyclic azine compound (1) will be described below.

[Substrate 1]
The substrate is not particularly limited, and examples thereof include a glass plate, a quartz plate, a plastic plate and the like. Further, in the case of a configuration in which emitted light is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.

Examples of light-transmitting plastic films include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate ( PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.

[Anode 2]
An anode 2 is provided on the substrate 1 (on the hole injection layer 3 side).
For organic electroluminescent devices configured such that emitted light is extracted through the anode, the anode is formed of a material that is transparent or substantially transparent to the emitted light.

The transparent material used for the anode is not particularly limited, but examples include indium-tin oxide (ITO; Indium Tin Oxide), indium-zinc oxide (IZO; Indium Zinc Oxide), tin oxide, aluminum・Doped tin oxide, magnesium-indium oxide, nickel-tungsten oxide, other metal oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, metal sulfides such as zinc sulfide, etc. is mentioned.
In the case of an organic electroluminescence device configured to extract light only from the cathode side, the transmission characteristics of the anode are not important. Accordingly, examples of materials used for the anode in this case include gold, iridium, molybdenum, palladium, platinum, and the like.
A buffer layer (electrode interface layer) may be provided on the anode.

[Hole injection layer 3, hole transport layer 5]
A hole injection layer 3, a charge generation layer 4 described later, and a hole transport layer 5 are provided in this order from the anode 2 side between the anode 2 and a light emitting layer 6 described later.
The hole injection layer and the hole transport layer have a function of transferring holes injected from the anode to the light emitting layer, and the hole injection layer and the hole transport layer are interposed between the anode and the light emitting layer. As a result, more holes are injected into the light-emitting layer at a lower electric field.

Moreover, the hole injection layer and the hole transport layer also function as electron blocking layers. That is, electrons injected from the cathode and transported from the electron injection layer and/or the electron transport layer to the light-emitting layer are blocked by the electron barrier present at the interface between the light-emitting layer and the hole injection layer and/or the hole transport layer. , leakage into the hole injection layer and/or the hole transport layer is suppressed. As a result, the electrons are accumulated at the interface in the light-emitting layer, resulting in an effect such as an improvement in current efficiency, and an organic electroluminescence device with excellent light-emitting performance can be obtained.

Materials for the hole injection layer and the hole transport layer have at least one of hole injection properties, hole transport properties, and electron blocking properties. Materials for the hole injection layer and the hole transport layer may be either organic or inorganic.

Specific examples of materials for the hole injection layer and hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, and amino-substituted chalcone. derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (especially thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, styryl Examples include amine compounds. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred, and aromatic tertiary amine compounds are particularly preferred.

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(3-methylphenyl)-[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-tolyl aminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'-di(4-methoxyphenyl)-4,4'-diaminobiphenyl,N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino) quadri Phenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenyl amino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino ] biphenyl (NPD), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA) and the like.
Inorganic compounds such as p-type-Si and p-type-SiC can also be cited as examples of the material for the hole injection layer and the material for the hole transport layer.

The hole injection layer and the hole transport layer may have a single layer structure composed of one or more materials, or may have a laminated structure composed of multiple layers having the same composition or different compositions.

[Charge generation layer 4]
A charge generation layer 4 may be provided between the hole injection layer 3 and the hole transport layer 5 .
Materials for the charge generation layer are not particularly limited, but examples include dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT -CN).
The charge generation layer may have a single-layer structure composed of one or more materials, or may have a laminated structure composed of multiple layers having the same composition or different compositions.

[Light emitting layer 6]
A light-emitting layer 6 is provided between the hole-transporting layer 5 and an electron-transporting layer 7 to be described later.
Materials for the light-emitting layer include phosphorescent light-emitting materials, fluorescent light-emitting materials, and thermally activated delayed fluorescent light-emitting materials. In the light-emitting layer, electron-hole pairs recombine, resulting in light emission.

The emissive layer may consist of a single small molecule material or a single polymeric material, but more commonly consists of a host material doped with a guest compound. Emission comes primarily from dopants and can have any color.

Examples of host materials include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specifically, DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene) 1, 1′-biphenyl), TBADN (2-tert-butyl-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 can be mentioned.

Examples of fluorescent dopants include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium, thiapyrylium compounds, fluorene derivatives, periflanthene derivatives, and indenoperylenes. derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, carbostyril compounds, and the like. The fluorescent dopant may be a combination of two or more selected from these.

Examples of phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium and osmium.

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](acetylacetonato)iridium(III), Ir(PPy)3(tris(2-phenylpyridine)iridium(III)), and FIrPic (bis(3,5- difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium (III))) and the like.

Moreover, the luminescent material is not limited to being contained only in the luminescent layer. For example, the light-emitting material may be contained in a layer adjacent to the light-emitting layer (hole-transporting layer 5 or electron-transporting layer 7). This can further increase the current efficiency of the organic electroluminescence device.

The light-emitting layer may have a single-layer structure composed of one or more materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.

[Electron transport layer 7]
An electron transport layer 7 is provided between the light emitting layer 6 and a cathode 8 which will be described later.
The electron transport layer has a function of transmitting electrons injected from the cathode to the light emitting layer. By interposing an electron-transporting layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

As described above, the electron transport layer preferably contains the cyclic azine compound represented by the above formula (1).

The electron transport layer may further contain a conventionally known electron transport material in addition to the cyclic azine compound (1). Conventionally known electron transport materials include, for example, 8-hydroxyquinolinate lithium (Liq), bis(8-hydroxyquinolinate) zinc, bis(8-hydroxyquinolinate) copper, bis(8-hydroxyquinolinate), tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)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-cresolato)gallium, bis(2 -methyl-8-quinolinato)-1-naphtholatoaluminum, or bis(2-methyl-8-quinolinato)-2-naphtholatogallium, 2-[3-(9-phenanthrenyl)-5-(3-pyridinyl) phenyl]-4,6-diphenyl-1,3,5-triazine and 2-(4,''-di-2-pyridinyl[1,1':3',1''-terphenyl]-5- yl)-4,6-diphenyl-1,3,5-triazine, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10- phenanthroline), BAlq (bis(2-methyl-8-quinolinolato)-4-(phenylphenolato)aluminum), and bis(10-hydroxybenzo[h]quinolinato)beryllium).

The electron-transporting layer may have a single-layer structure composed of one or more materials, or may have a laminated structure composed of multiple layers having the same composition or different compositions.
When the electron-transporting layer has a two-layer structure in which the first electron-transporting layer is on the light-emitting layer side and the second electron-transporting layer is on the cathode side, the second electron-transporting layer preferably contains the cyclic azine compound (1).

[Cathode 8]
A cathode 8 is provided on the electron transport layer 7 .
In the case of an organic electroluminescence device configured so that only light emitted through the anode is taken out, the cathode can be made of any conductive material.
Cathode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium/copper mixtures, magnesium/silver mixtures, magnesium/aluminum mixtures, magnesium/indium mixtures, aluminum/aluminum oxide (Al ₂ O ₃ ) mixtures, indium. , lithium/aluminum mixtures, rare earth metals, and the like.
A buffer layer (electrode interface layer) may be provided on the cathode (electron transport layer side).

[Method of Forming Each Layer]
Each layer except for the electrodes (anode and cathode) described above can be formed by applying the material of each layer (with a material such as a binder resin and a solvent as necessary) by, for example, a vacuum deposition method, a spin coating method, a casting method, an LB ( It can be formed by thinning by a known method such as the Langmuir-Blodgett method.
The thickness of each layer thus formed is not particularly limited and can be appropriately selected depending on the situation, but is usually in the range of 5 nm to 5 μm.

The anode and cathode can be formed by thinning an electrode material by a method such as vapor deposition or sputtering. A pattern may be formed through a mask of a desired shape during vapor deposition or sputtering, or a pattern of a desired shape may be formed by photolithography after forming a thin film by vapor deposition, sputtering, or the like.

The film thickness of the anode and cathode is preferably 1 μm or less, more preferably 10 nm or more and 200 nm or less.

The organic electroluminescence element according to one aspect of the present invention may be used as a kind of lamp such as an illumination light source or an exposure light source, a type of projection device that projects an image, or a still image or a moving image that can be directly viewed. You may use it as a display apparatus (display) of the type to carry out. When used as a display device for reproducing moving images, the driving method may be either a simple matrix (passive matrix) method or an active matrix method. Further, by using two or more kinds of organic electroluminescence elements of this embodiment having different emission colors, a full-color display device can be produced.

The cyclic azine compound (1) according to one aspect of the present invention can be synthesized by appropriately combining known reactions (eg, Suzuki-Miyaura cross-coupling reaction, etc.).

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

¹ H-NMR measurement was performed using Gemini200 (manufactured by Varian).
The glass transition temperature was measured using DSC7020 (manufactured by Hitachi High-Tech Science).
The luminous properties of the organic electroluminescent device were evaluated by applying a direct current to the fabricated device at room temperature and using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse Co., Ltd.).

Synthetic Example-1

Under a nitrogen stream, 2-(3-chlorophenyl)-4,6-[(1,1′-biphenyl)-4-yl]-1,3,5-triazine (5.50 g, 11.09 mmol), 3- (2,6-diphenylpyridin-4-yl)phenylboronic acid (5.93 g, 16.88 mmol), palladium acetate (107.9 mg, 0.481 mmol), and 2-dicyclohexylphosphino-2′,4′, 6′-Triisopropylbiphenyl (420.1 mg, 0.881 mmol) was dissolved in tetrahydrofuran (225 mL). A 2M potassium carbonate aqueous solution (22 mL, 44 mmol) was added thereto, and the mixture was stirred at 75° C. for 70 hours. After allowing to cool to room temperature, the solvent was distilled off under reduced pressure, and the precipitated solid was separated by filtration. The obtained solid was washed with water (50 mL), ethanol (50 mL) and hexane (50 mL). This solid was dissolved in toluene (300 mL). Activated carbon was added to this solution and the mixture was stirred, filtered through celite, and the filtrate was concentrated under reduced pressure. This concentrate was recrystallized (toluene, twice) to give the desired 4,6-[(1,1′-biphenyl)-4-yl]-2-[3′-(2,6-diphenyl- A white solid of 4-pyridyl)-biphenyl-3-yl]-1,3,5-triazine (compound A-46) was obtained (5.31 g, 79% yield).

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.42 (t, J = 7.4 Hz, 4H), 7.48-7.53 (m, 8H), 7.70-7.76 (m , 6H), 7.80-7.84 (m, 5H), 7.88 (d, J = 7.8Hz, 1H), 7.95 (d, J = 7.8Hz, 1H), 8.02 (s, 2H), 8.12 (s, 1H), 8.23-8.26 (m, 4H), 8.85-8.90 (m, 5H), 9.11 (s, 1H).
The glass transition temperature of compound A-46 was 118°C.

Synthesis example-2

Experiment similar to Synthesis Example-1 except that 3-(2,6-diphenylpyridin-4-yl)phenylboronic acid was changed to 3-(4,6-diphenylpyridin-2-yl)phenylboronic acid Manipulation yields the desired 4,6-[(1,1′-biphenyl)-4-yl]-2-[3′-(2,6-diphenyl-4-pyridyl)-biphenyl-3-yl] A white solid of -1,3,5-triazine (compound A-1) was obtained (yield: 7.41 g, yield: 64%).
¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.54 (m, 12H), 7.68-7.75 (m, 6H), 7.79-7.81 (m, 6H ), 7.86 (d, J = 7.8 Hz, 1 H), 7.96 (d, J = 7.9 Hz, 1 H), 7.99 (d, J = 25 Hz, 2 H), 8.26 (t , J = 7.3 Hz, 3H), 8.58 (s, 1H), 8.84 (d, J = 7.8Hz, 1H), 8.89 (d, J = 8.4Hz, 4H), 9 .14(s, 1H).

Then, element evaluation was carried out using the obtained compound.

Device example-1 (see Fig. 2)
(Preparation of substrate 101 and anode 102)
As a substrate having an anode on its surface, a glass substrate with an ITO transparent electrode, in which an indium-tin oxide (ITO) film (thickness: 110 nm) with a width of 2 mm was patterned in stripes, was prepared. Then, after washing the substrate with isopropyl alcohol, the surface was treated by ozone ultraviolet washing.

(Preparation for vacuum deposition)
Each layer was vacuum-deposited on the surface-treated substrate after cleaning by a vacuum deposition method to laminate each layer.
First, the glass substrate was introduced into a vacuum deposition tank, and the pressure was reduced to 1.0×10 ⁻⁴ Pa. Then, each layer was produced in the following order according to the film forming conditions of each layer.

(Preparation of hole injection layer 103)
Sublimation purified N-[1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2 - amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were deposited at a rate of 0.15 nm/sec to form a film of 10 nm, forming a hole injection layer; 103 was made.

(Preparation of first hole transport layer 1051)
Sublimation purified N-[1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2 -Amine was deposited at a rate of 0.15 nm/sec to a thickness of 85 nm to prepare a first hole transport layer 1051 .

(Preparation of second hole transport layer 1052)
Sublimation-purified N-phenyl-N-(9,9-diphenylfluoren-2-yl)-N-(1,1′-biphenyl-4-yl)amine was deposited at a rate of 0.15 nm/sec to form a 5 nm film. , a second hole-transporting layer 1052 was fabricated.

(Production of light-emitting layer 106)
3-(10-phenyl-9-anthryl)-dibenzofuran and 2,7-bis[N,N-di-(4-tertbutylphenyl)]amino-bisbenzofurano-9,9′-spirofluorene purified by sublimation was deposited at a ratio of 95:5 (mass ratio) to a thickness of 20 nm to prepare the light-emitting layer 106 . The deposition rate was 0.18 nm/sec.

(Preparation of first electron transport layer 1071)
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 the first electron transport layer 1071 .

(Preparation of second electron transport layer 1072)
4,6-[(1,1′-biphenyl)-4-yl]-2-[3′-(2,6-diphenyl-4-pyridyl)-biphenyl-3-yl synthesized in Synthesis Example-1 ]-1,3,5-Triazine (Compound A-46) and Liq were deposited at a ratio of 50:50 (mass ratio) to a thickness of 25 nm to prepare a second electron transport layer 1072 . The deposition rate was 0.15 nm/sec.

(Preparation of cathode 108)
Finally, a metal mask was placed so as to be perpendicular to the ITO stripes on the substrate, and a cathode 108 was formed. The cathode was formed by depositing silver/magnesium (mass ratio 1/10) and silver in this order to 80 nm and 20 nm, respectively, to form a two-layer structure. The deposition rate of silver/magnesium was 0.5 nm/second, and the deposition rate of silver was 0.2 nm/second.

As described above, an organic electroluminescence device 100 having a light emitting area of 4 mm ² as shown in FIG. 2 was produced. Each film thickness was measured with a stylus film thickness meter (DEKTAK, manufactured by Bruker).

Further, this device was sealed in a nitrogen atmosphere glove box with an oxygen and water concentration of 1 ppm or less. Sealing was performed by using a bisphenol F-type epoxy resin (manufactured by Nagase ChemteX Corporation) between the glass sealing cap and the film formation substrate (element).

A direct current was applied to the organic electroluminescence device produced as described above, and the luminescence characteristics were evaluated using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse). As light emission characteristics, current efficiency (cd/A) was measured when a current density of 10 mA/cm ² was applied, and element life (h) during continuous lighting was measured. The device life (h) in Table 1 is measured by measuring the luminance decay time during continuous lighting when the manufactured device is driven at an initial luminance of 1000 cd/m ² , and until the luminance (cd/m ² ) decreases by 5%. was measured. The drive voltage, current efficiency, and device life are relative values with the result of device reference example 1 described later as a reference value (100). Table 1 shows the measurement results obtained.

Device example-2
In Element Example-2, 4,6-[(1,1'-biphenyl)-4-yl]-2-[3'-(4) synthesized in Synthesis Example-2 was used instead of Compound A-46. ,6-Diphenyl-2-pyridyl)-biphenyl-3-yl]-1,3,5-triazine (Compound A-1) was used, but in the same manner as in Device Example-1. made and evaluated. Table 1 shows the measurement results obtained.

Element reference example-1
In Element Example-1, 2-[5-(9-phenanthryl)-4′-(2-pyrimidyl) described in Patent Document 1 (JP-A-2011-063584) instead of compound A-46 An organic electroluminescence device was produced and evaluated in the same manner as in Device Example-1 except that biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (ETL-2) was used. . Table 1 shows the measurement results obtained.

The cyclic azine compound (1) according to one aspect of the present invention is extremely excellent in heat resistance of film quality, and by using the compound, it is possible to provide an organic electroluminescence device excellent in long life and current efficiency.
Moreover, the cyclic azine compound (1) according to one aspect of the present invention is used as an electron-transporting material for organic electroluminescence devices, which is excellent in low driving voltage. Furthermore, according to the cyclic azine compound (1), it is possible to provide an organic electroluminescence device with low power consumption.
In addition, the cyclic azine compound according to one aspect of the present invention has good thermal stability during sublimation purification, so that it is excellent in operability of sublimation purification, and provides a material with few impurities that cause deterioration of the organic electroluminescent device. can do. In addition, the cyclic azine compound according to one aspect of the present invention can provide a long-life organic electroluminescence device because the stability of the deposited film is excellent.
In addition, since the thin film made of the cyclic azine compound (1) according to one aspect of the present invention is excellent in electron-transporting ability, hole-blocking ability, redox resistance, water resistance, oxygen resistance, electron injection characteristics, etc., it is It is useful as a material for devices, and as an electron transport material, a hole block material, a light emitting host material, and the like. It is especially useful when used as an electron transport material.
Further, the cyclic azine compound (1) according to one aspect of the present invention has a wide bandgap and a high triplet excitation level. TADF) can be suitably used for an organic electroluminescence device.

Reference Signs List 1, 101 substrate 2, 102 anode 3, 103 hole injection layer
4 charge generation layer 5,105 hole transport layer 6,106 light emitting layer 7,107 electron transport layer 8,108 cathode 51,1051 first hole transport layer 52,1052 second hole transport layer 71,1071 first electron Transport layer 72, 1072 Second electron transport layer 100 Organic electroluminescence element

Claims (9)

A cyclic azine compound represented by formula (1):

In formula (1),
Ar ¹ are identical to each other and represent a 4-biphenyl group;
Ar ² and Ar ³ are each independently
A monocyclic ring that may be linked, a condensed ring that may be linked, or a structure in which these are linked,
(i) an aromatic hydrocarbon group having 6 to 24 carbon atoms,
(ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting only of a 6-membered ring, or
(iii) a heteroaromatic group having 3 to 25 carbon atoms composed of atoms selected from the group consisting of H, C, O, and S, or
(iv) represents a group composed of a combination of any two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ² and Ar ³ is 4 to 25;
one of Z ¹ and Z ² represents a nitrogen atom and the other represents C—H;
A forms a single bond with B ¹ or B ² ;
one of B ¹ and B ² forms a single bond with A and the other represents a hydrogen atom;
Each group represented by Ar ² and Ar ³ is each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and 1 It may have one or more groups selected from the group consisting of 4 to 4 alkoxy groups. ^2. The cyclic azine compound according to claim 1, wherein neither Ar2 nor ^Ar3 has a substituent. 3. The cyclic azine compound according to claim 1 , wherein the total number of ring-constituting carbon atoms of Ar ² and Ar ³ is 4-20. 4. The cyclic azine compound according to any one of claims 1 to 3 , wherein the sum of the total number of ring-constituting carbon atoms of Ar ² and the total number of ring-constituting carbon atoms of Ar ³ is 8-32. Ar ² and Ar ³ are phenyl, p-tolyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, 2-(2-pyridyl)phenyl, 3-( 2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 2-( 4-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 2-(1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 4-( 1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 2-(9-phenanthryl)phenyl group, 3-( 9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 4-(9-anthryl)phenyl group, 2-( 3-fluoranthenyl)phenyl group, 3-(3-fluoranthenyl)phenyl group, 4-(3-fluoranthenyl)phenyl group, 2-(2-triphenylenyl)phenyl group, 3-(2-triphenylenyl) phenyl group, 4-(2-triphenylenyl)phenyl group, 2-(3-quinolyl)phenyl group, 3-(3-quinolyl)phenyl group, 4-(3-quinolyl)phenyl group, 2-(8-quinolyl) phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl) Phenyl group, 2-(2-dibenzothienyl) phenyl group, 3-(2-dibenzothienyl) phenyl group, 4-(2-dibenzothienyl) phenyl group, 2-(4-dibenzothienyl) phenyl group, 3-( 4-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 2-(2-dibenzofuryl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 2-(4-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 1-naphthyl group, 2-naphthyl group, 3-quinolyl group, 4-quinolyl group, 8-quinolyl group, 3-isoquinolyl group, 2-benzothienyl group, 2-benzothyl group a lyl group, 9-anthryl group, 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, 4-dibenzofuryl group, 3-fluoranthenyl group, 1-pyrenyl group, or 2. The cyclic azine compound according to claim 1, which is a 2-triphenylenyl group. Ar ² and Ar ³ are phenyl, p-tolyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, 3-(2-pyridyl)phenyl, 4-( 2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 2-( 1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 3-( 9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 3-(3-fluoranthenyl)phenyl group, 4 -(3-fluoranthenyl)phenyl group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group, 3-(3-quinolyl)phenyl group, 4-(3-quinolyl)phenyl group , 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group , 3-(2-dibenzothienyl) phenyl group, 4-(2-dibenzothienyl) phenyl group, 3-(4-dibenzothienyl) phenyl group, 4-(4-dibenzothienyl) phenyl group, 3-(2- dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 2-pyridyl group, 3-pyridyl group, 4 -pyridyl group, 1-naphthyl group, 2-naphthyl group, 3-quinolyl group, 8-quinolyl group, 2-benzothienyl group, 2-benzofuryl group, 9-anthryl group, 9-phenanthryl group, 2-dibenzothienyl group , 2-dibenzofuryl group, 4-dibenzothienyl group, 4-dibenzofuryl group, the cyclic azine compound according to claim 1 . A material for an organic electroluminescence device comprising the cyclic azine compound according to any one of claims 1 to 6 . An electron transport material for an organic electroluminescence device, comprising the cyclic azine compound according to any one of claims 1 to 6 . An organic electroluminescence device comprising the cyclic azine compound according to any one of claims 1 to 6 .

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