JP2020070262A - Cyclic azine compound, organic electroluminescent element material, electron transport material for organic electroluminescent element, and organic electroluminescent element - Google Patents

Abstract

To provide a cyclic azine compound having excellent heat resistance and current efficiency.SOLUTION: The present invention relates to a cyclic azine compound represented by a compound obtained by the following formula. The compound is a cyclic azine compound having excellent durability and current efficiency, which can provide an organic electroluminescent element material and an electron transport material for an organic electroluminescent element.SELECTED DRAWING: Figure 1

Description

  The present invention relates to a cyclic azine compound, a material for an organic electroluminescence device, an electron transport material for an organic electroluminescence device, and an organic electroluminescence device.

The organic electroluminescence device is used not only for a small display but also for a large-sized television, lighting, and the like, and its development has been vigorously carried out.
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, reduced driving voltage, and long life. There is.
Patent Document 2 discloses a cyclic azine compound having a diarylpyridine structure.

JP, 2011-063584, A International Publication No. 2017/221974

However, in recent years, the market demand for organic electroluminescent devices has increased more and more, and materials having excellent current efficiency characteristics, driving voltage characteristics, and long life characteristics are required.
Here, although the organic electroluminescent device using the cyclic azine compound disclosed in Patent Document 1 exhibits excellent driving voltage characteristics, further improvement is required in the device life and current efficiency.
Further, although the organic electroluminescent device using the cyclic azine compound disclosed in Patent Document 2 exhibits current efficiency and long life superior to those of Patent Document 1, the life of the device is further improved. It has been demanded. In particular, in recent years, since the years of use of smartphones have tended to increase, organic electroluminescent elements are required to withstand long-term use, and are increasingly used in televisions and lighting, and their life expectancy is required. Is extremely high.

One aspect of the present invention is directed to providing a cyclic azine compound, a material for an organic electroluminescent device, and an electron transport material for an organic electroluminescent device, which are excellent in durability and current efficiency.
Further, another aspect of the present invention is directed to providing an organic electroluminescent device having excellent durability and current efficiency.

  A cyclic azine compound according to one embodiment 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 monocycle which may be linked, a condensed ring which 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 only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 3 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of 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 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 a carbon number of 1 It may have one or more groups selected from the group consisting of alkoxy groups of 4 to 4.

A material for an organic electroluminescence device according to another aspect of the present invention contains the above cyclic azine compound.
An electron transport material for an organic electroluminescence device according to another aspect of the present invention contains the above cyclic azine compound.
An organic electroluminescent device according to another aspect of the present invention includes the 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 electroluminescent device, and an electron transport material for an organic electroluminescent device, which are excellent in durability and current efficiency.
According to another aspect of the present invention, it is possible to provide an organic electroluminescent element having excellent durability and current efficiency.

It is a schematic sectional drawing which shows an example of the laminated constitution of the organic electroluminescent element containing the cyclic azine compound concerning 1 aspect of this invention. It is a schematic sectional drawing which shows an example (element example-1) of the laminated constitution of the organic electroluminescent element containing the cyclic azine compound concerning 1 aspect of this invention.

  Hereinafter, the cyclic azine compound according to one embodiment of the present invention will be described in detail.

<Cyclic azine compound>
A cyclic azine compound according to one embodiment 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 monocycle which may be linked, a condensed ring which 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 only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 3 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of 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 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 a carbon number of 1 It may have one or more groups selected from the group consisting of alkoxy groups of 4 to 4.

  Hereinafter, the cyclic azine compound represented by the formula (1) may be referred to as a cyclic azine compound (1). The definition of the substituent in the cyclic azine compound (1) and its preferred specific examples are as follows.

[About Ar 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 ¹ is more preferably a 4-biphenyl group in terms of excellent electron transporting material properties.

[About 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 has a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked;
(Ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms, which is a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these rings are linked and which has only a 6-membered ring and has 4 to 25 carbon atoms;
(Iii) composed of an atom selected from the group consisting of H, C, O, and S, which is a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked. A 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).
The groups (i) to (iv) represented by Ar ² and Ar ³ are each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, and a carbon number of 1 to 1. It may have one or more groups selected from the group consisting of a C4 alkyl group and a C1-4 alkoxy group. It is more preferable that Ar ² and Ar ³ have no substituent.

  The aromatic hydrocarbon group (i) is not particularly limited, but examples thereof include phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, triphenylenyl group. , Chrysenyl group, perylenyl group, fluoranthenyl group, acenaphthyl group and the like are preferable 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. It may have one or more groups selected from the group consisting of a group and an alkoxy group having 1 to 4 carbon atoms.

  The nitrogen-containing heteroaromatic group (ii) is not particularly limited, but examples thereof include pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, quinolyl group, isoquinolyl group, phenanthridyl group, and benzoquinolyl group. , And acridinyl group are preferred examples. Note that the heteroaromatic group containing a 5-membered ring (for example, a carbazolyl group) is not included in the nitrogen-containing heteroaromatic group (ii) and is not included in the cyclic azine compound represented by the formula (1). Further, as described above, these substituents (nitrogen-containing heteroaromatic group) are each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, and a carbon number of 1 to 4 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 (iii) heteroaromatic group is not particularly limited, and examples thereof include thienyl group, furyl group, bithienyl group, bifuryl group, benzothienyl group, benzofuryl group, dibenzothienyl group, dibenzofuryl group and the like. Are preferred examples. 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, 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 alkyl group having 1 to 4 carbon atoms in Ar ² and Ar ³ is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and a t-butyl group. A group etc. are mentioned as a preferable example.

The alkoxy group having 1 to 4 carbon atoms in Ar ² and Ar ³ is not particularly limited, but methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, t- A butoxy group etc. are mentioned as a preferable example.

Specific examples of the groups represented by Ar ² and Ar ³ are not particularly limited, but preferable examples include the 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 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-te t- butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl 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-d Rubiphenyl-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) fe 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-phenylnaphthalen-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalen-4-yl group, 1-phenylnaphthalene-5 -Yl group, 1-phenylnaphthalen-6-yl group, 1-phenylnaphthalen-7-yl group, 1-phenylnaphthalen-8-yl group, 2-phenylnaphthalen-1-yl group, 2-phenylnaphthalene-3 -Yl group, 2-phenylnaphthalen-4-yl group, 2-phenylnaphthalen-5-yl group, 2-phenylnaphthalen-6-yl group, 2-phenylnaphthalen-7-yl group, 2-phenylnaphthalene-8 -Yl group, 1-methylnaphthalen-4-yl group, 1-methylnaphthalen-5-yl group, 1-methylnaphthalen-6-yl group, 1-methylnaphthalene 7-yl group, 1-methylnaphthalen-8-yl group, 2-methylnaphthalen-1-yl group, 2-methylnaphthalen-3-yl group, 2-methylnaphthalen-4-yl group, 2-methylnaphthalene- 5-yl group, 2-methylnaphthalen-6-yl group, 2-methylnaphthalen-7-yl group, 2-methylnaphthalen-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 -Phenylphenanthrene-5-yl group, 2-phenylphenanthrene 6-yl group, 2-phenylphenanthrene-7-yl group, 2-phenylphenanthren-8-yl group, 2-phenylphenanthren-9-yl group, 2-phenylphenanthren-10-yl group, 3-phenylphenanthrene- 1-yl group, 3-phenylphenanthren-2-yl group, 3-phenylphenanthren-4-yl group, 3-phenylphenanthren-5-yl group, 3-phenylphenanthren-6-yl group, 3-phenylphenanthrene- 7-yl group, 3-phenylphenanthren-8-yl group, 3-phenylphenanthren-9-yl group, 3-phenylphenanthren-10-yl group, 4-phenylphenanthren-1-yl group, 4-phenylphenanthrene- 2-yl group, 4-phenylphenanthren-3-yl group, 4-phen Ruphenanthren-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-methylphen 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 Phenanthrene-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 Phenanthrene-10-yl group, 4-methylphenanthren-1-yl group, 4-methylphenanthrene-2- Group, 4-methylphenanthren-3-yl group, 4-methylphenanthren-5-yl group, 4-methylphenanthren-6-yl group, 4-methylphenanthren-7-yl group, 4-methylphenanthrene-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-phenylanthracene-4-yl group, 1 -Phenylanthracen-5-yl group, 1-phenylanthracen-6-yl group, 1-phenylanthracene-7-yl group, 1-phenylanthracene-8-yl group, 1-phenylanthracene-9-yl group, 1 -Phenylanthracen-10-yl group, 2-phenylanthracen-1-yl group, 2-phenylanthracen-3-yl group, 2-phenylanthracen-4-yl group, 2-phenylanthracene-5-yl group, 2 -Phenylanthracen-6-yl group, 2-phenylanthracen-7-yl group, 2-phenylanthracene-8-i Group, 2-phenylanthracen-9-yl group, 2-phenylanthracen-10-yl group, 9-phenylanthracen-1-yl group, 9-phenylanthracene-2-yl group, 9-phenylanthracene-3-yl group Group, 9-phenylanthracen-4-yl group, 9-phenylanthracen-5-yl group, 9- (2-pyridyl) -anthracen-10-yl group, 9- (3-pyridyl) -anthracene-10-yl group 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-methylpyren-5-yl group, 2-methylpyrene -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-methylpyrene- 7-yl group, 9-methylpyren-8-yl group, 9-methylpyren-10-yl group.

(9): Fluoranthen-1-yl group, fluoranthen-1-yl group, fluoranthen-2-yl group, fluoranthen-3-yl group, fluoranthen-4-yl group, fluoranthen-5-yl group, fluoranthene-6- An yl group, a fluoranthen-7-yl group, a fluoranthen-8-yl group, a fluoranthen-9-yl group, a fluoranthen-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, chrysen-1- An yl group, a chrysen-2-yl group, a chrysen-5-yl group, a 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 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-methylpyrazin-2 -Yl group, 5,6-diphenylpyrazin-2-yl group, pyrimidin-2-yl group, pyrimidin-4-yl group, pyrimidin-5-yl group, 2,4-diphenyl Pyrimidin-6-yl group, 4,6-diphenylpyrimidin-2-yl group, acridin-1-yl group, acridin-1-yl group, acridine-2-yl group, acridine-3-yl group, acridine-4 -Yl group, acridine-9-yl group, phenanthridin-1-yl group, phenanthridin-1-yl group, phenanthridin-2-yl group, phenanthridin-3-yl group, phenanthridine -4-yl group, phenanthridin-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, Zo [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.

(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 Group, dibenzofuran-3-yl group, 3-methylthiophen-2-yl group, 4-methylthiophen-2-yl group, 5-methylthio group Fen-2-yl group, 2-methylthiophen-3-yl group, 4-methylthiophen-3-yl group, 5-methylthiophen-3-yl group, 3-methylfuran-2-yl group, 4-methyl Furan-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-methylbenzothiophen-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-methylbenzo Ofen-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-methylbenzothiophen-6-yl group, 5-methylbenzothiophen-6-yl group, 7-methylbenzothiophen-6-yl group, 2-methylbenzothiophene -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-methyl group Benzofuran-5-yl group, 7-methylbenzofuran-5-yl group, 2-methylbenzofuran-6-yl group, 3-methylbenzofuran-6-yl group, 4-methylbenzofuran-6-yl group, 5-methyl Benzofuran-6-yl group, 7-methylbenzofuran-6-yl group, 2-methylbenzofuran-7-yl group, 3-methylbenzofuran-7-yl group, 4-methylbenzofuran-7-yl group, 5-methyl Benzofuran-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-methyldibenzothiophen-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-methyldibenzothiophene -3-yl group, 4-methyldibenzothiophen-3-yl group, 6-methyldibenzothiophen-3-yl group, 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-methyl Benzofuran-3-yl group, 7-methyl-dibenzofuran-3-yl group, 8-methyl-dibenzofuran-3-yl group, 9-methyl-dibenzofuran-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-phenylthiophen-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-phenylbenzothiophen-3- 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-phenylbenzothiophene -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-phenylbenzothiophen-6-yl group, 5-phenylbenzothiophen-6-yl group, 7-phenylbenzothiophene- 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-phenyl group Benzofuran-5-yl group, 6-phenylbenzofuran-5-yl group, 7-phenylbenzofuran-5-yl group, 2-phenylbenzofuran-6-yl group, 3-phenylbenzofuran-6-yl group, 4-phenyl Benzofuran-6-yl group, 5-phenylbenzofuran-6-yl group, 7-phenylbenzofuran-6-yl group, 2-phenylbenzofuran-7-yl group, 3-phenylbenzofuran-7-yl group, 4-phenyl Benzofuran-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-phenyldibenzothiophen-2- 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 , 2-phenyldibenzothiophen-3-yl group, 4-phenyldibenzothiophen-3-yl group, 6-phenyldibenzothiophen-3-yl group, 7-phenyldibenzothiophen-3-yl group, 8-phenyldibenzothiophene -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-phenyldibe Zofran 3-yl group, 6-phenyl-dibenzofuran-3-yl group, 7-phenyl-dibenzofuran-3-yl group, 8-phenyl-dibenzofuran-3-yl group, 9-phenyl-dibenzofuran-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 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 -( -Pyridyl) benzothiophen-4-yl group, 7- (2-pyridyl) benzothiophen-4-yl group, 2- (2-pyridyl) benzothiophen-5-yl group, 3- (2-pyridyl) benzothiophene -5-yl group, 4- (2-pyridyl) benzothiophen-5-yl group, 6- (2-pyridyl) benzothiophen-5-yl group, 7- (2-pyridyl) benzothiophen-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) be Zothiophen-7-yl group, 4- (2-pyridyl) benzothiophen-7-yl group, 5- (2-pyridyl) benzothiophen-7-yl group, 6- (2-pyridyl) benzothiophen-7-yl group Basis.

(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 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-pi Dil) 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- - 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) dibenzothiophen-2 -Yl group, 6- (2-pyridyl) dibenzothiophen-2-yl group, 7- (2-pyridyl) dibenzothiophen-2-yl group, 8- (2-pyridyl) dibenzothio En-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) dibenzothiophen-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 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) dibenzofura -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) benzothiophen-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 -( -Pyridyl) benzothiophen-4-yl group, 7- (3-pyridyl) benzothiophen-4-yl group, 2- (3-pyridyl) benzothiophen-5-yl group, 3- (3-pyridyl) benzothiophene -5-yl group, 4- (3-pyridyl) benzothiophen-5-yl group, 6- (3-pyridyl) benzothiophen-5-yl group, 7- (3-pyridyl) benzothiophen-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) be Zothiophen-7-yl group, 4- (3-pyridyl) benzothiophen-7-yl group, 5- (3-pyridyl) benzothiophen-7-yl group, 6- (3-pyridyl) benzothiophen-7-yl group Basis.

(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 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-pi Dil) 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- - 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) dibenzothiophen-2 -Yl group, 6- (3-pyridyl) dibenzothiophen-2-yl group, 7- (3-pyridyl) dibenzothiophen-2-yl group, 8- (3-pyridyl) dibenzothio En-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) dibenzothiophen-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 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) dibenzofura -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 -( -Pyridyl) benzothiophen-4-yl group, 7- (4-pyridyl) benzothiophen-4-yl group, 2- (4-pyridyl) benzothiophen-5-yl group, 3- (4-pyridyl) benzothiophene -5-yl group, 4- (4-pyridyl) benzothiophen-5-yl group, 6- (4-pyridyl) benzothiophen-5-yl group, 7- (4-pyridyl) benzothiophen-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) be Zothiophen-7-yl group, 4- (4-pyridyl) benzothiophen-7-yl group, 5- (4-pyridyl) benzothiophen-7-yl group, 6- (4-pyridyl) benzothiophen-7-yl group Basis.

(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 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-pi Dil) 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- - 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) dibenzothiophen-2 -Yl group, 6- (4-pyridyl) dibenzothiophen-2-yl group, 7- (4-pyridyl) dibenzothiophen-2-yl group, 8- (4-pyridyl) dibenzothio En-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) dibenzothiophen-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 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) dibenzofura -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-pi) Nyl) phenyl group, 4- (1-pyrenyl) phenyl group, 2- (2-pyrenyl) phenyl group, 3- (2-pyrenyl) phenyl group, 4- (2-pyrenyl) phenyl group, 2- (2- Fluoranthenyl) phenyl group, 3- (2-fluoranthenyl) phenyl group, 4- (2-fluoranthenyl) phenyl group, 2- (3-fluoranthenyl) phenyl group, 3- (3-fluorane) Phenyl) 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, 4- (1-triphenylenyl) phenyl group, 2- (2-triphenylenyl) phenyl, 3- (2-triphenylenyl) phenyl, 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-quinoli ) 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- Nzothienyl) 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 group, 2- (7-benzofuryl) phenyl group, 3- (7-benzofuryl) phenyl group, 4- (7-benzofuryl) furan 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, a 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 , 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 A -pyrenyl group, a 2-triphenylenyl group or the like is preferable. 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- Ruoranthenyl) 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-dibenzo) Ryl) 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 preferable.

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 each 4 to 25. Further, 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 each preferably 4 to 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 carbon atoms in the ring) and the group represented by Ar ¹ has a phenyl group, the diphenylfluorene group having a phenyl group may be replaced by these (substituted The group + Ar ² ) as a whole will have 31 ring-constituting carbon atoms.

The total 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 to 32.

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

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

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

The use of the cyclic azine compound (1) will be described below.
<Material for organic electroluminescent device, electron transport material for organic electroluminescent device>
The cyclic azine compound (1) is not particularly limited, but can be used, for example, as a material for an organic electroluminescence device. Further, the cyclic azine compound (1) can be used, for example, as an electron transport material for an organic electroluminescence device.
That is, the material for organic electroluminescent elements according to one aspect of the present invention contains the cyclic azine compound (1). Further, the electron transport material for an organic electroluminescence device according to one aspect of the present invention contains the cyclic azine compound (1). The material for an organic electroluminescent device and the electron transport material for an organic electroluminescent device containing the cyclic azine compound (1) contribute to the production of an organic electroluminescent device excellent in durability and current efficiency.

<Organic electroluminescent device>
An organic electroluminescent device according to one aspect of the present invention includes a cyclic azine compound (1).
The structure of the organic electroluminescent element is not particularly limited, but examples thereof include the following structures (i) to (vi).
(I): Anode / light emitting layer / cathode (ii): Anode / hole transporting layer / light emitting layer / cathode (iii): Anode / light emitting layer / electron transporting layer / cathode (iv): Anode / hole transporting 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 electroluminescent element according to one embodiment of the present invention will be described in more detail with reference to FIG. 1 by taking the configuration of (vi) above as an example. FIG. 1 is a schematic cross-sectional view showing an example of a laminated structure of an organic electroluminescence device containing a cyclic azine compound according to one embodiment of the present invention.
Note that the organic electroluminescent element shown in FIG. 1 has a so-called bottom emission type element structure, but the organic electroluminescent element according to one embodiment of the present invention is limited to the bottom emission type element structure. is not. That is, the organic electroluminescent element according to one aspect of the present invention may have a top emission type element configuration or any other known element configuration.

  The organic electroluminescent device 100 includes 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, and 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 directly provided on the hole injection layer 3. Good. In addition, a single layer having the functions of a plurality of layers, such as an electron injecting / transporting layer having both the function of the electron injection layer and the function of the electron transport layer in a single layer, is used as the plurality of layers. 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 be composed 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 a light emitting layer and a layer between the light emitting layer and the cathode. Therefore, in the configuration example shown in FIG. 1, the organic electroluminescent 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. When the electron injection layer is provided between the electron transport layer and the cathode, the electron injection layer is The cyclic azine compound (1) may be contained.
In addition, below, the organic electroluminescent element 100 in which the electron carrying layer 7 contains the cyclic azine compound (1) is demonstrated.

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

  Examples of the light-transmissive plastic film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), polyether imide, polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate ( PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.

[Anode 2]
The anode 2 is provided on the substrate 1 (on the side of the hole injection layer 3).
In the case of an organic electroluminescent device having a structure in which emitted light is extracted through the anode, the anode is formed of a material that allows the emitted light to pass through or substantially allows the emitted light to pass therethrough.

The transparent material used for the anode is not particularly limited, and examples thereof include indium-tin oxide (ITO), indium-zinc oxide (IZO), tin oxide, and 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, and metal sulfides such as zinc sulfide. Is mentioned.
In the case of an organic electroluminescent device having a structure in which light is extracted only from the cathode side, the transmission characteristics of the anode are not important. Therefore, examples of the material 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 between the anode 2 and a light emitting layer 6 described below from the anode 2 side.
The hole injection layer and the hole transport layer have a function of transmitting the 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, many holes are injected into the light emitting layer at a lower electric field.

  Further, the hole injection layer and the hole transport layer also function as a layer having an electron barrier property. That is, the 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 existing at the interface between the light emitting layer and the hole injection layer and / or the hole transport layer. The 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 effects such as improved current efficiency, and an organic electroluminescent device having excellent light emitting performance can be obtained.

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

  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 chalcones Derivative, oxazole derivative, styrylanthracene derivative, fluorenone derivative, hydrazone derivative, stilbene derivative, silazane derivative, aniline copolymer, conductive polymer oligomer (particularly thiophene oligomer), porphyrin compound, aromatic tertiary amine compound, styryl Examples thereof include amine compounds. Among these, porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds are preferable, and aromatic tertiary amine compounds are particularly preferable.

Specific examples of the aromatic tertiary amine compound and the styrylamine compound include N, N, N ', N'-tetraphenyl-4,4'-diaminophenyl and 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 '. -Ji (4-Metoki Phenyl) -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-diphenyl) Vinyl) 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 can be mentioned.
Inorganic compounds such as p-type-Si and p-type-SiC can also be given as examples of the material of the hole injection layer and the material of the hole transport layer.

  The hole injection layer and the hole transport layer may have a single-layer structure made of one kind or two or more kinds of materials, or may have a laminated structure made of a plurality of layers having the same composition or different compositions.

[Charge generation layer 4]
The charge generation layer 4 may be provided between the hole injection layer 3 and the hole transport layer 5.
The material of the charge generation layer is not particularly limited, but for example, 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 two or more materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.

[Light emitting layer 6]
A light emitting layer 6 is provided between the hole transport layer 5 and an electron transport layer 7 described later.
Examples of the material of the light emitting layer include a phosphorescent light emitting material, a fluorescent light emitting material, and a heat-activated delayed fluorescent light emitting material. In the light emitting layer, electron-hole pairs are recombined, and as a result, light emission occurs.

  The emissive layer may consist of a single low molecular weight material or a single polymeric material, but more commonly it consists of a host material doped with a guest compound. The emission mainly originates from the dopant and can have any color.

  Examples of the host material 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 the fluorescent dopant include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compound, thiopyran compound, polymethine compound, pyrylium, thiapyrylium compound, fluorene derivative, perifuranten derivative, indenoperylene. Examples thereof include derivatives, bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, and carbostyryl compounds. The fluorescent dopant may be a combination of two or more selected from these.

  Examples of the phosphorescent dopant include organic metal complexes of transition metals such as iridium, platinum, palladium and osmium.

  Specific examples of the fluorescent dopant and the phosphorescent dopant 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.

  Further, 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 (hole transport layer 5 or electron transport layer 7) adjacent to the light emitting layer. This can further increase the current efficiency of the organic electroluminescent device.

  The light emitting layer may have a single-layer structure made of one or more kinds of materials, or a laminated structure made 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 described later.
The electron transport layer has a function of transmitting 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.

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

  In addition to the cyclic azine compound (1), the electron transport layer may further include a conventionally known electron transport material. Examples of conventionally known electron transport materials include lithium 8-hydroxyquinolinato (Liq), bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, and bis (8-hydroxyquinolinate). Nato) manganese, 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-cresolate) gallium, bis (2) -Methyl-8-quinolinato) -1-naphtholate aluminum, Or bis (2-methyl-8-quinolinato) -2-naphtholate gallium, 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- (Quinolinolate) -4- (phenylphenolate) aluminum), bis (10-hydroxybenzo [h] quinolinato) beryllium) and the like.

The electron transport layer may have a single-layer structure composed of one or more materials, or a laminated structure composed of a plurality of layers having the same composition or different compositions.
When the electron transport layer has a two-layer structure in which the light emitting layer side is the first electron transport layer and the cathode side is the second electron transport layer, the second electron transport 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 having a structure in which only the light emission that has passed through the anode is taken out, the cathode can be formed of any conductive material.
Examples of materials for the cathode include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) mixture, 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]
For each layer except the electrodes (anode, cathode) described above, the material of each layer (with a material such as a binder resin and a solvent, if necessary), for example, a vacuum deposition method, a spin coating method, a casting method, an LB ( It can be formed by thinning the film by a known method such as Langmuir-Blodgett method).
The thickness of each layer thus formed is not particularly limited and may be appropriately selected depending on the situation, but is usually in the range of 5 nm to 5 μm.

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

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

  The organic electroluminescent element according to one embodiment of the present invention may be used as a kind of lamp for lighting or as an exposure light source, or may be a projection device of a type for projecting an image, or to directly view a still image or a moving image. You may use as a display device (display) of the type. When used as a display device for moving image reproduction, either a simple matrix (passive matrix) system or an active matrix system may be used as a drive system. In addition, a full-color display device can be manufactured by using two or more kinds of organic electroluminescent elements of this embodiment having different emission colors.

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

  Hereinafter, the present invention will be described in more detail based on Examples, but the present invention should not be construed as being limited to 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 Co., Ltd.).
The emission characteristics of the organic electroluminescent device were evaluated by applying a direct current to the prepared device at room temperature and using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse).

  Synthesis 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). To this, a 2 M aqueous potassium carbonate solution (22 mL, 44 mmol) was added, 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 filtered off. The obtained solid was washed with water (50 mL), ethanol (50 mL), 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. By recrystallizing this concentrated solution (toluene, twice), the target 4,6-[(1,1'-biphenyl) -4-yl] -2- [3 '-(2,6-diphenyl- 4-Pyridyl) -biphenyl-3-yl] -1,3,5-triazine (Compound A-46) was obtained as a white solid (5.31 g, 79% yield).

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.42 (t, J = 7.4 Hz, 4 H), 7.48-7.53 (m, 8 H), 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 degreeC.

Synthesis Example-2

An 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. Perform the operation to obtain 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) (7.41 g, 64% yield) was obtained.
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 = 7.8Hz, 1H), 7.96 (d, J = 7.9Hz, 1H), 7.99 (d, J = 25Hz, 2H), 8.26 (t). , J = 7.3 Hz, 3 H), 8.58 (s, 1 H), 8.84 (d, J = 7.8 Hz, 1 H), 8.89 (d, J = 8.4 Hz, 4 H), 9 .14 (s, 1H).

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

Element 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 a 2 mm wide indium-tin oxide (ITO) film (film thickness 110 nm) was patterned in a stripe shape was prepared. Next, this substrate was washed with isopropyl alcohol and then surface-treated by ozone ultraviolet ray cleaning.

(Preparation for vacuum deposition)
Each layer was vacuum-deposited by a vacuum vapor deposition method on the substrate subjected to the surface treatment after washing to form each layer in a laminated manner.
First, the glass substrate was introduced into a vacuum vapor deposition tank, and the pressure was reduced to 1.0 × 10 ⁻⁴ Pa. Then, the respective layers were formed 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 formed into a 10 nm film at a rate of 0.15 nm / sec to form a hole injection layer. 103 was produced.

(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 to a thickness of 85 nm at a rate of 0.15 nm / sec to form a first hole transport layer 1051.

(Production of Second Hole Transport Layer 1052)
Sublimation-purified N-phenyl-N- (9,9-diphenylfluoren-2-yl) -N- (1,1'-biphenyl-4-yl) amine was formed into a 5 nm film at a rate of 0.15 nm / sec. A second hole transport layer 1052 was prepared.

(Production of Light-Emitting Layer 106)
Sublimation-purified 3- (10-phenyl-9-anthryl) -dibenzofuran and 2,7-bis [N, N-di- (4-tertbutylphenyl)] amino-bisbenzofurano-9,9'-spirofluorene Was formed into a 20 nm film at a ratio of 95: 5 (mass ratio) to form a light emitting layer 106. The film formation rate was 0.18 nm / sec.

(Production of First Electron Transport Layer 1071)
Sublimated and 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 first electron transport layer 1071.

(Production 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 formed into a film with a thickness of 50:50 (mass ratio) at a thickness of 25 nm to form a second electron transport layer 1072. The film formation rate was 0.15 nm / sec.

(Production of cathode 108)
Finally, a metal mask was arranged so as to be perpendicular to the ITO stripe on the substrate, and the cathode 108 was formed. The cathode was formed into a two-layer structure by depositing silver / magnesium (mass ratio 1/10) and silver in this order at 80 nm and 20 nm, respectively. The silver / magnesium film formation rate was 0.5 nm / sec, and the silver film formation rate was 0.2 nm / sec.

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

  Further, this element was sealed in a nitrogen atmosphere glove box having oxygen and water concentrations of 1 ppm or less. The sealing was performed by using a bisphenol F type epoxy resin (manufactured by Nagase Chemtex) for the glass sealing cap and the film-forming substrate (element).

A direct current was applied to the organic electroluminescence device produced as described above, and the emission characteristics were evaluated using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse). As the emission characteristics, the current efficiency (cd / A) when a current density of 10 mA / cm ² was passed was measured, and the device life (h) during continuous lighting was measured. Incidentally, Table 1 of element lifetime (h) measures the luminance decay time at the time of continuous lighting when driving was prepared device at an initial luminance 1000 cd / ^{m 2,} to the luminance (cd / ^{m 2)} is reduced 5% The time required for the measurement was measured. The driving voltage, the current efficiency, and the device life are relative values with the result in the device reference example 1 described later as a reference value (100). The obtained measurement results are shown in Table 1.

Element Example-2
In Device Example-2, instead of Compound A-46, 4,6-[(1,1'-biphenyl) -4-yl] -2- [3 '-(4 was synthesized in Synthesis Example-2. , 6-Diphenyl-2-pyridyl) -biphenyl-3-yl] -1,3,5-triazine (Compound A-1) was used, except that an organic electroluminescent device was prepared in the same manner as in Example 1. It was prepared and evaluated. The obtained measurement results are shown in Table 1.

Element reference example-1
In Device Example-1, 2- [5- (9-phenanthryl) -4 '-(2-pyrimidyl) described in Patent Document 1 (JP 2011-063584 A) instead of Compound A-46. Biphenyl-3-yl] -4,6-diphenyl-1,3,5-triazine (ETL-2) was used, and an organic electroluminescent device was prepared and evaluated in the same manner as in Device Example-1. .. The obtained measurement results are shown in Table 1.

The cyclic azine compound (1) according to one aspect of the present invention is extremely excellent in heat resistance of the film quality, and by using the compound, it is possible to provide an organic electroluminescent device having long life and excellent current efficiency.
Further, the cyclic azine compound (1) according to one aspect of the present invention is used as an electron transport material for an organic electroluminescence device which is excellent in low driving voltage. Furthermore, the cyclic azine compound (1) can provide an organic electroluminescent device with low power consumption.
In addition, the cyclic azine compound according to one embodiment of the present invention provides a material that has excellent operability in sublimation purification because it has good thermal stability during sublimation purification, and has few impurities that cause element deterioration of the organic electroluminescent element. can do. In addition, the cyclic azine compound according to one embodiment of the present invention is excellent in stability of a deposited film, and thus can provide an organic electroluminescence device having a long life.
In addition, the thin film made of the cyclic azine compound (1) according to one embodiment 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 useful as a material for devices, and is also useful as an electron transport material, a hole blocking 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 embodiment of the present invention has a wide band gap and a high triplet excitation level, so that it can be used not only for conventional fluorescent devices but also for phosphorescent devices and thermally activated delayed fluorescence ( It can be suitably used for an organic electroluminescence device using TADF).

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 electroluminescent device

Claims (10)

The cyclic azine compound represented by the 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 monocycle which may be linked, a condensed ring which 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 only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 3 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of 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 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 a carbon number of 1 It may have one or more groups selected from the group consisting of alkoxy groups of 4 to 4. The cyclic azine compound according to claim 1, wherein Ar ¹ is a 4-biphenyl group. The cyclic azine compound according to claim 1, wherein neither Ar ² nor Ar ³ has a substituent. The cyclic azine compound according to any one of claims 1 to ³ , wherein the total number of ring-constituting carbon atoms of Ar ² and Ar ³ is 4 to 20, respectively. The cyclic azine compound according to any one of claims 1 to 4, wherein the total 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 to 32. Ar ² and Ar ³ are 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-fluorane Phenyl) 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-benzofuryl group 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 or 2, which is a triphenylenyl group. Ar ² and Ar ³ are 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 -The cyclic azine compound according to claim 1 or 2, which is a dibenzothienyl group, a 2-dibenzofuryl group, a 4-dibenzothienyl group, or a 4-dibenzofuryl group.   A material for an organic electroluminescent device, which comprises the cyclic azine compound according to claim 1.   An electron transport material for an organic electroluminescence device, comprising the cyclic azine compound according to claim 1.   An organic electroluminescent device comprising the cyclic azine compound according to claim 1.

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