JP7159550B2 - Cyclic azine compound, material for organic electroluminescence device and electron transport material for organic electroluminescence device - Google Patents

Description

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

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

JP 2011-063584 A

In recent years, however, the demand for organic electroluminescence devices from the market has increased more and more, and materials that are excellent in all of luminous efficiency characteristics, drive voltage characteristics, and long life characteristics are in demand.

Here, although the organic electroluminescence device using the cyclic azine compound disclosed in Patent Document 1 exhibits excellent driving voltage characteristics, there is a demand for further improvements in device life and luminous efficiency.

An object of one aspect of the present invention is to provide a cyclic azine compound, a material for an organic electroluminescence device, and an electron-transporting material for an organic electroluminescence device, which are excellent in durability and current efficiency.

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

In general formula (1),
each Ar ¹ independently represents a phenyl group, a naphthyl group, or a pyridyl group;
^Ar2 is
A monocyclic ring that may be linked, a condensed ring that may be linked, or a structure in which these are linked,
an aromatic hydrocarbon group having 6 to 24 carbon atoms,
a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting only of a 6-membered ring, or
a heteroaromatic group having 3 to 25 carbon atoms composed of atoms selected from the group consisting of H, C, O, and S, or
represents a hydrogen atom;
A represents a group represented by general formula (2) or general formula (3);

In general formula (2) and general formula (3),
Ar ³ represents a phenyl group, a naphthyl group, a phenanthryl group, a fluoranthenyl group, a pyridyl group, a quinolyl group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms;
* represents the binding position;
L ¹ represents a divalent or trivalent phenyl group, naphthyl group, pyridyl group, or a single bond;
L ² and L ³ each independently represent a phenylene group, a naphthylene group, or a pyridylene group;
p is 0 or 1;
m and n each independently represent 0, 1, or 2;
when m is 2, two L ² may be the same or different;
when n is 2, the two ^L3s may be the same or different;
each group represented by Ar ¹ , Ar ³ , L ¹ , L ² and L ³ may be substituted with a fluorine atom, a methyl group or a phenyl group;
Each group represented by Ar ² is substituted with 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, or an alkoxy group having 1 to 4 carbon atoms. may have been

A material for an organic electroluminescence device according to another aspect of the present invention contains a cyclic azine compound represented by the general formula (1).
An electron-transporting material for an organic electroluminescence device according to still another aspect of the present invention contains a cyclic azine compound represented by the general formula (1).

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

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

The cyclic azine compound according to one embodiment of the present invention is described in detail below.
<Cyclic azine compound>
A cyclic amine compound according to one aspect of the present invention is represented by general formula (1):

In general formula (1),
each Ar ¹ independently represents a phenyl group, a naphthyl group, or a pyridyl group;
^Ar2 is
A monocyclic ring that may be linked, a condensed ring that may be linked, or a structure in which these are linked,
an aromatic hydrocarbon group having 6 to 24 carbon atoms,
a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting only of a 6-membered ring, or
a heteroaromatic group having 3 to 25 carbon atoms composed of atoms selected from the group consisting of H, C, O, and S, or
represents a hydrogen atom;
A represents a group represented by general formula (2) or general formula (3);

In general formula (2) and general formula (3),
Ar ³ represents a phenyl group, a naphthyl group, a phenanthryl group, a fluoranthenyl group, a pyridyl group, a quinolyl group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms;
* represents the binding position;
L ¹ represents a divalent or trivalent phenyl group, naphthyl group, pyridyl group, or a single bond;
L ² and L ³ each independently represent a phenylene group, a naphthylene group, or a pyridylene group;
p is 0 or 1;
m and n each independently represent 0, 1, or 2;
when m is 2, two L ² may be the same or different;
when n is 2, the two ^L3s may be the same or different;
each group represented by Ar ¹ , Ar ³ , L ¹ , L ² and L ³ may be substituted with a fluorine atom, a methyl group or a phenyl group;
Each group represented by Ar ² is substituted with 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, or an alkoxy group having 1 to 4 carbon atoms. may have been

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

[About Ar ¹ ]
In formula (1), each Ar ¹ independently represents a phenyl group, a naphthyl group, or a pyridyl group. These groups may be substituted with fluorine atoms, methyl groups, or phenyl groups.
The fluorine-substituted phenyl group, naphthyl group, or pyridyl group for Ar ¹ is not particularly limited, and examples thereof include a fluorophenyl group, a pentafluorophenyl group, a difluorophenyl group, a fluoronaphthyl group, Preferred examples include a difluoronaphthyl group, a fluoropyridyl group, a difluoropyridyl group, and the like.
The methyl-substituted phenyl group, naphthyl group, or pyridyl group for Ar ¹ is not particularly limited, and examples thereof include tolyl, methylnaphthyl, dimethylphenyl, dimethylnaphthyl, and methylpyridyl. Preferable examples include a group, a dimethylpyridyl group, and the like.
The phenyl group, naphthyl group, or pyridyl group substituted with a phenyl group for Ar ¹ is not particularly limited, and examples thereof include a biphenyl group, a phenylnaphthyl group, a terphenyl group, a diphenylnaphthyl group, and a phenylpyridyl group. Preferred examples include groups and the like.

Ar ¹ is more preferably each independently a phenyl group, a naphthyl group, a biphenyl group, or a pyridyl group in terms of excellent electron-transporting material properties.
Two Ar ¹ 's may be the same or different.

Specific examples of Ar ¹ are not particularly limited. ,5-dimethylphenyl group, mesityl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,4-difluorophenyl group, 3,5-difluorophenyl group, biphenyl-2-yl group , biphenyl-3-yl group, biphenyl-4-yl group, 1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalene-2-yl group, 1-phenylnaphthalene-3-yl group, 1-phenylnaphthalene- 4-yl group, 1-phenylnaphthalene-5-yl group, 1-phenylnaphthalene-6-yl group, 1-phenylnaphthalene-7-yl group, 1-phenylnaphthalene-8-yl group, 2-phenylnaphthalene- 1-yl group, 2-phenylnaphthalene-3-yl group, 2-phenylnaphthalene-4-yl group, 2-phenylnaphthalene-5-yl group, 2-phenylnaphthalene-6-yl group, 2-phenylnaphthalene- 7-yl group, 2-phenylnaphthalene-8-yl group, 1-methylnaphthalene-4-yl group, 1-methylnaphthalene-5-yl group, 1-methylnaphthalene-6-yl group, 1-methylnaphthalene- 7-yl group, 1-methylnaphthalene-8-yl group, 2-methylnaphthalene-1-yl group, 2-methylnaphthalene-3-yl group, 2-methylnaphthalene-4-yl group, 2-methylnaphthalene- 5-yl group, 2-methylnaphthalene-6-yl group, 2-methylnaphthalene-7-yl group, 2-methylnaphthalene-8-yl group, 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, 2-phenylpyridin-6-yl group, 3-phenylpyridin-6-yl group, 4-phenylpyridin-6-y group, 5-phenylpyridin-6-yl group, 2-phenylpyridin-3-yl group, 2-phenylpyridin-5-yl group, 3-phenylpyridin-5-yl group, 4-phenylpyridin-3- Preferable examples include an yl group, a 3-phenylpyridin-4-yl group, a 2-phenylpyridin-4-yl group and the like. Among these substituents, phenyl group, biphenyl-3-yl group, biphenyl-4-yl group, 1-naphthyl group, 2-naphthyl group, 2- A pyridyl group, a 3-pyridyl group, or a 4-pyridyl group is more preferred.

[About ^Ar2 ]
^Ar2 is
(i) an aromatic hydrocarbon group having 6 to 24 carbon atoms, which is a monocyclic ring that may be linked, a condensed ring that may be linked, or a structure in which these are linked;
(ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting only of a 6-membered ring, which is a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked;
(iii) composed of atoms selected from the atomic group consisting of H, C, O, and S, which is a single ring that may be linked, a condensed ring that may be linked, or a structure in which these are linked a heteroaromatic group having 3 to 25 carbon atoms; or
(iv) represents a hydrogen atom;
Each group (i) to (iii) represented by Ar ² is 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, or a It may have 1 to 4 alkoxy groups.
p is 0 or 1;

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

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

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

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

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

Ar ² is preferably a group selected from any one of (i) to (iii) having no substituents, or (iv) a hydrogen atom, which has a high glass transition temperature and has no substituents A group selected from any one of (i) to (iii) is more preferable.

Specifically, Ar ² is a hydrogen atom; 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, or an alkoxy group having 1 to 4 carbon atoms. optionally substituted phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, chrysenyl group, acenaphthyl group, pyrimidyl group , a pyrazyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, and a dibenzothienyl group; and among these, groups other than hydrogen atoms are preferred. Ar ² is a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyrimidyl group, pyrazyl group, pyridyl group, quinolyl group , an isoquinolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a biphenyl group, or a pyridylphenyl group.

Specific examples of the group represented by -L ² _m -Ar ² _p are not particularly limited, but preferable examples include groups (1) to (41) shown below.

(1): hydrogen atom, 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-ethylphenyl group, 4-ethylphenyl group, 2,4-diethylphenyl group, 3,5-diethylphenyl group, 2-propylphenyl group, 3-propylphenyl group, 4-propylphenyl group, 2,4- Dipropylphenyl group, 3,5-dipropylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2,4-diisopropylphenyl group, 3,5-diisopropylphenyl group, 2- Butylphenyl group, 3-butylphenyl group, 4-butylphenyl group, 2,4-dibutylphenyl group, 3,5-dibutylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4- tert-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-ethylbiphenyl-2-yl group, 3-propylbiphenyl-4-yl group, 6-propylbiphenyl-3-yl group, 5-propylbiphenyl-2-yl group, 3-isopropylbiphenyl-4-yl group, 6-isopropylbiphenyl-3-yl group, 5-isopropylbiphenyl-2-yl group, 3-butylbiphenyl-4-yl group, 6-butylbiphenyl-3-yl group, 5-butylbiphenyl-2-yl group, 3-tert-butylbiphenyl-4-yl group, 4'-tert-butylbiphenyl-4-yl group, 6-tert-butylbiphenyl-3-yl group, 5-tert-butylbiphenyl-2-yl group.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(41): 1-anthryl group, 2-anthryl group, 9-anthryl group, 10-phenylanthracen-9-yl group, 10-(2-pyridyl)-anthracen-9-yl group, 10-(3-pyridyl )-anthracen-9-yl group, 10-(4-pyridyl)-anthracen-9-yl group.

Among these substituents, a hydrogen atom, a phenyl group, a p-tolyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 3 -(2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 2-pyridyl group, 3-pyridyl group, 4 -pyridyl group, 2-phenylpyridin-6-yl group, 2-phenylpyridin-5-yl group, 2-phenylpyridin-4-yl group, 3-phenylpyridin-5-yl group, 3-phenylpyridin-6 -yl group, 2,6-diphenylpyridin-4-yl group, 4,6-diphenylpyridin-2-yl group, 2-pyrimidyl group, 2-pyrazyl group, 1-naphthyl group, 2-naphthyl group, 3- quinolyl group, 4-quinolyl group, 3-isoquinolyl group, 2-benzothienyl group, 2-benzofuryl group, 2-fluorenyl group, 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluorene-3- yl group, 9,9-dimethylfluoren-4-yl group, 9,9-diphenylfluoren-2-yl group, 9,9-diphenylfluoren-3-yl group, 9,9-diphenylfluoren-4-yl group , 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, 4-dibenzofuryl group, A 3-fluoranthenyl group, a 1-pyrenyl group, a 2-triphenylenyl group, and the like are preferred.

Among these substituents, Ar ² is a hydrogen atom, a phenyl group, a p-tolyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 3-(2- pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-phenylpyridin-6-yl group, 2-phenylpyridin-5-yl group, 2-phenylpyridin-4-yl group, 3-phenylpyridin-5-yl group, 3-phenylpyridin-6-yl group, 2,6-diphenylpyridin-4-yl group, 4,6-diphenylpyridin-2-yl group, 2-pyrimidyl group, 2-pyrazyl group, 1-naphthyl group, 2-naphthyl group, 3-quinolyl group, 4 -quinolyl group, 3-isoquinolyl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 9-phenanthryl group, 3-fluoranthenyl group, 1-pyrenyl group, or 2-triphenylenyl groups are more preferred.

[About A]
A represents a group represented by the following general formula (2) or general formula (3). However, * represents a binding position.

In general formulas (2) and (3), Ar ³ is a phenyl group, a naphthyl group, a phenanthryl group, a fluoranthenyl group, a pyridyl group, a quinolyl group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms. represents These groups may be substituted with fluorine atoms, methyl groups, or phenyl groups.
Ar ³ is preferably a hydrogen atom for ease of synthesis.
* represents a binding position.

[About ^L1 ]
L ¹ represents a divalent or trivalent phenyl group, naphthyl group, pyridyl group, or single bond. These groups may be substituted with fluorine atoms, methyl groups, or phenyl groups.
Among these groups, L ¹ is preferably each independently a divalent or trivalent phenyl group, a pyridyl group, or a single bond, in terms of easy availability of raw materials. or a single bond.

[Regarding L ² and L ³ ]
L ² and L ³ each independently represent a phenylene group, a naphthylene group, or a pyridylene group. These groups may be substituted with fluorine atoms, methyl groups, or phenyl groups.
Among these groups, L ² and L ³ are more preferably each independently a phenylene group, a naphthylene group, or a pyridylene group having no substituents, from the viewpoint of easy availability of raw materials.
m and n represent 0, 1, or 2; When m is ² , two L2's may be the same or different. When n is ² , two L3's may be the same or different.

When the cyclic azine compound (1) is used as a component of an organic light emitting diode (OLED), effects such as high luminous efficiency and long life can be obtained. In particular, these effects are exhibited even more when the cyclic azine compound (1) is used as the electron transport layer.
Among the compounds represented by the general formula (1), specific examples of particularly preferred compounds include the following (A-1) to (A-728). The cyclic azine compound ( 1) is not limited to these.

Applications of the cyclic azine compound (1) are described below.

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

<Organic electroluminescent device>
An organic electroluminescent device according to one aspect of the present invention contains a cyclic azine compound (1).
The structure of the organic electroluminescence device is not particularly limited, but includes, for example, the following structures (i) to (vi).

(i): anode/light-emitting layer/cathode
(ii): anode/hole transport layer/light-emitting layer/cathode
(iii): anode/light emitting layer/electron transport layer/cathode
(iv): anode/hole-transport layer/light-emitting layer/electron-transport layer/cathode
(v): anode/hole-injection layer/hole-transport layer/light-emitting layer/electron-transport layer/electron-injection layer/cathode
(vi): anode/hole injection layer/charge generation layer/hole transport layer/light emitting layer/electron transport layer/cathode.

Hereinafter, the organic electroluminescence device according to one embodiment of the present invention will be described in more detail with reference to FIG. 1, taking the configuration (vi) above as an example.
FIG. 1 is a schematic cross-sectional view showing an example of a lamination structure of an organic electroluminescence device containing a cyclic azine compound according to one embodiment of the present invention.

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

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

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

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

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

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

A buffer layer (electrode interface layer) may be provided on the anode.

[Hole injection layer 3, hole transport layer 5]
A hole injection layer 3, a charge generation layer 4 described later, and a hole transport layer 5 are provided in this order from the anode 2 side between the anode 2 and a light emitting layer 6 described later.

The hole injection layer and the hole transport layer have a function of transferring holes injected from the anode to the light emitting layer, and the hole injection layer and the hole transport layer are interposed between the anode and the light emitting layer. As a result, more holes are injected into the light-emitting layer at a lower electric field.

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

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

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

Specific examples of aromatic tertiary amine compounds and styrylamine compounds include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'- Bis(3-methylphenyl)-[1,1′-biphenyl]-4,4′-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis (4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolyl aminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N' -di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino) quadri Phenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenyl amino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino ] biphenyl (NPD), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA) and the like.

Inorganic compounds such as p-type-Si and p-type-SiC can also be cited as examples of the material for the hole injection layer and the material for the hole transport layer.

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

[Charge generation layer 4]
A charge generation layer 4 may be provided between the hole injection layer 3 and the hole transport layer 5 .
Materials for the charge generation layer are not particularly limited, but examples include dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT -CN).

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

[Light emitting layer 6]
A light-emitting layer 6 is provided between the hole-transporting layer 5 and an electron-transporting layer 7 to be described later.
Materials for the light-emitting layer include phosphorescent light-emitting materials, fluorescent light-emitting materials, and thermally activated delayed fluorescent light-emitting materials. In the light-emitting layer, electron-hole pairs recombine, resulting in light emission.
The emissive layer may consist of a single small molecule material or a single polymeric material, but more commonly consists of a host material doped with a guest compound. Emission comes primarily from dopants and can have any color.

Examples of host materials include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specifically, DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene) 1, 1′-biphenyl), TBADN (2-tert-butyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4′-bis (carbazol-9-yl)biphenyl), CDBP (4,4′-bis(carbazol-9-yl)-2,2′-dimethylbiphenyl), 2-(9-phenylcarbazol-3-yl)-9- [4-(4-phenylphenylquinazolin-2-yl)carbazole, 9,10-bis(biphenyl)anthracene and the like can be mentioned.

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

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

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

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

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

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

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

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

[Cathode 8]
A cathode 8 is provided on the electron transport layer 7 .
In the case of an organic electroluminescence device configured so that only light emitted through the anode is taken out, the cathode can be made of any conductive material.

Cathode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium/copper mixtures, magnesium/silver mixtures, magnesium/aluminum mixtures, magnesium/indium mixtures, aluminum/aluminum oxide (Al ₂ O ₃ ) mixtures, indium. , lithium/aluminum mixtures, rare earth metals, and the like.

A buffer layer (electrode interface layer) may be provided on the cathode (electron transport layer side).

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

The thickness of each layer thus formed is not particularly limited and can be appropriately selected depending on the situation, but is usually in the range of 5 nm to 5 μm.

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

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

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

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

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

¹ H-NMR measurement was performed using Gemini200 (manufactured by Varian).

The luminous properties of the organic electroluminescent device were evaluated by applying a direct current to the fabricated device at room temperature and using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse Co., Ltd.).

Synthetic Example-1

4,6-diphenyl-2-[3-(9-phenanthryl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]- under an argon stream 1,3,5-triazine (6.00 g, 9.81 mmol), 4-chlorophenylphenylsulfone (3.67 g, 14.5 mmol), palladium acetate (35.7 mg, 0.159 mmol), and 2-dicyclohexylphosphino -2',4',6'-Triisopropylbiphenyl (148.1 mg, 0.310 mmol) was dissolved in tetrahydrofuran (100 mL). A 2M potassium carbonate aqueous solution (15.0 mL, 30.0 mmol) was added thereto, and the mixture was stirred at 75° C. for 26 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. Water (50 mL) and methanol (50 mL) were added to the resulting concentrate, the mixture was stirred at room temperature, and the precipitated solid was filtered off. The obtained solid was washed with water (30 mL), methanol (30 mL) and hexane (30 mL). This solid was dissolved in toluene (250 mL), silica gel was added, and the mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The solid obtained by drying the concentrate was purified once by recrystallization (toluene) to give the target 4,6-diphenyl-2-[5-(9-phenanthryl)-4′-phenylsulfinyl. A white solid of biphenyl-3-yl]-1,3,5-triazine (compound A-5) was obtained (6.12 g, 89% yield).

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.45-7.69 (m, 13H), 7.78 (s, 1H), 7.87-7.92 (m, 5H), 7. 96 (d, J = 5.0 Hz, 2H), 8.04 (d, J = 8.8 Hz, 2H), 8.68-8.73 (m, 5H), 8.8 (d, J = 8 .3Hz, 1H), 8.91 (s, 1H), 9.00 (s, 1H).

Next, device evaluation will be described.
The structural formulas and abbreviations of the compounds used for element evaluation are shown below.

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

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

(Preparation of hole injection layer 3)
A 55 nm film of HIL purified by sublimation was formed at a rate of 0.15 nm/sec to prepare a hole injection layer.

(Preparation of charge generation layer 4)
A 5 nm film of HAT purified by sublimation was formed at a rate of 0.05 nm/sec to prepare a charge generating layer.

(Preparation of first hole transport layer 51)
HTL-1 was deposited to a thickness of 10 nm at a rate of 0.15 nm/sec to prepare a first hole transport layer.

(Preparation of second hole transport layer 52)
HTL-2 was deposited to a thickness of 10 nm at a rate of 0.15 nm/sec to form a second hole transport layer.

(Preparation of light-emitting layer 6)
EML-1 and EML-2 were deposited at a ratio of 95:5 (mass ratio) to a thickness of 25 nm to prepare a light-emitting layer. The deposition rate was 0.18 nm/sec.

(Preparation of first electron transport layer 71)
ETL-1 was deposited to a thickness of 5 nm at a rate of 0.15 nm/sec to prepare the first electron transport layer 7 .

(Preparation of second electron transport layer 72)
4,6-diphenyl-2-[5-(9-phenanthryl)-4′-phenylsulfinylbiphenyl-3-yl]-1,3,5-triazine synthesized in Synthesis Example-1 (Compound A-5) and Liq at a ratio of 50:50 (mass ratio) to form a film of 25 nm to form the second electron transport layer 71 . The deposition rate was 0.15 nm/sec.

(Preparation of cathode 8)
Finally, a metal mask was arranged so as to be perpendicular to the ITO stripes on the substrate, and a cathode 8 was formed. The cathode was formed by depositing silver/magnesium (mass ratio 1/10) and silver in this order to 80 nm and 20 nm, respectively, to form a two-layer structure. The deposition rate of silver/magnesium was 0.5 nm/second, and the deposition rate of silver was 0.2 nm/second.

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

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

A direct current was applied to the organic electroluminescence device produced as described above, and the luminescence characteristics were evaluated using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse). As light emission characteristics, current efficiency (cd/A) was measured when a current density of 10 mA/cm ² was applied, and element life (h) during continuous lighting was measured. The device life (h) in Table 1 is obtained by measuring the luminance decay time during continuous lighting when the manufactured device is driven at an initial luminance of 1000 cd/m ² , and until the luminance (cd/m ² ) decreases by 15%. was measured. The voltage, current efficiency, and device life are relative values with the result of device reference example 1 described later as a reference value (100). Table 1 shows the measurement results obtained.

Element reference example-1
2-[5-(9-phenanthryl)-3-(3-pyridyl)phenyl]-4,6-diphenyl-1 described in Patent Document 1 in place of compound A-5 in Element Example-1 ,3,5-triazine (ETL-2) was used, but an organic electroluminescence device was produced and evaluated in the same manner as in Device Example-1. Table 1 shows the measurement results obtained.

The cyclic azine compound (1) according to one aspect of the present invention is extremely excellent in heat resistance of film quality, and by using the compound, it is possible to provide an organic electroluminescence device excellent in long life and luminous efficiency.

Moreover, the cyclic azine compound (1) according to one aspect of the present invention is used as an electron-transporting material for organic electroluminescence devices, which is excellent in low driving voltage. Furthermore, according to the cyclic azine compound (1), it is possible to provide an organic electroluminescence device with low power consumption.

In addition, the cyclic azine compound according to one aspect of the present invention has good thermal stability during sublimation purification, so that it is excellent in operability of sublimation purification, and provides a material with few impurities that cause deterioration of the organic electroluminescent device. can do. In addition, the cyclic azine compound according to one aspect of the present invention can provide a long-life organic electroluminescence device because the stability of the deposited film is excellent.

In addition, the thin film made of the cyclic azine compound (1) according to one aspect of the present invention is excellent in electron-transporting ability, hole-blocking ability, redox resistance, water resistance, oxygen resistance, electron-injecting properties, and the like. It is useful as a material for devices, and as an electron transport material, a hole block material, a light emitting host material, and the like. It is especially useful when used as an electron transport material.

Further, the cyclic azine compound (1) according to one aspect of the present invention has a wide bandgap and a high triplet excitation level. TADF) can be suitably used for an organic electroluminescence device.

REFERENCE SIGNS LIST 1 substrate 2 anode 3 hole injection layer 4 charge generation layer 5 hole transport layer 6 light emitting layer 7 electron transport layer 8 cathode 51 first hole transport layer 52 second hole transport layer 71 first electron transport layer 72 second Electron transport layer 100 Organic electroluminescence device

Claims (3)

A cyclic azine compound represented by the general formula (1):

In general formula (1),
each Ar ¹ independently represents a phenyl group or a biphenyl group;
^Ar2 is
phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyrimidyl group, pyrazyl group, pyridyl group, quinolyl group, isoquinolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, or a hydrogen atom;
A represents a group represented by general formula (2) or general formula (3);

In general formula (2) and general formula (3),
Ar ³ represents a hydrogen atom;
* represents the binding position;
L ¹ represents a trivalent phenyl group or a single bond;
L ² and L ³ each independently represent an unsubstituted phenylene group or pyridylene group;
p is 0 or 1;
m and n each independently represent 0 or 1 ; A material for an organic electroluminescence device, comprising the cyclic azine compound represented by the general formula (1) according to claim 1 . An electron-transporting material for an organic electroluminescence device, comprising the cyclic azine compound represented by the general formula (1) according to claim 1 .

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