JP2019099513A - Cyclic azine compound, organic electroluminescent element material and electron transport material for organic electroluminescent element - Google Patents

Abstract

To provide an electron transport material excellent in heat resistance, long life of an organic electroluminescent element, and low voltage driving or luminous efficiency.SOLUTION: The present invention provides a cyclic azine compound represented by formula (1) (Aris a phenyl group, a naphthyl group or the like; Aris a C6-24 aromatic hydrocarbon group or the like; A is a group having a diphenyl sulfone structure or dibenzothiophene dioxide structure; L-Lare a phenylene group, a naphthylene group or the like; m and n are an integer of 0-2; p is 1 or 2).SELECTED DRAWING: Figure 1

Description

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

Organic electroluminescent devices are used not only for small displays but also for applications such as large televisions and illuminations, and their development has been energetically 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 is excellent in heat resistance, decreases in driving voltage, and contributes to provision of a long-lived organic electroluminescent device. There is.

JP, 2011-063584, A

  However, the demand from the market for organic electroluminescent devices in recent years has become increasingly high, and materials excellent in any of the light emission efficiency characteristics, the drive voltage characteristics, and the long life characteristics are required.

  Here, although the organic electroluminescent device using the cyclic azine compound disclosed in Patent Document 1 exhibits excellent drive voltage characteristics, further improvement is required for the lifetime of the device and the light emission efficiency.

  An aspect of the present invention is to provide a cyclic azine compound excellent in durability and current efficiency, a material for an organic electroluminescent device, and an electron transport material for an organic electroluminescent device.

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

In general formula (1),
Each Ar ¹ independently represents a phenyl group, a naphthyl group or a pyridyl group;
Ar ² is
A single ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
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, which is composed of an atom selected from the group consisting of H, C, O, and S, or
Represents a hydrogen atom;
A represents a group represented by the general formula (2) or the general formula (3);

In the general formula (2) and the 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 a bonding position;
L ¹ represents a divalent or trivalent phenyl group, a naphthyl group, a 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 identical or different from each other;
When n is 2, two L ³ may be identical or different from each other;
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 methyl pyridyl group, a dimethyl pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms It may be done.

The material for an organic electroluminescent element according to another aspect of the present invention includes the cyclic azine compound represented by the above general formula (1).
The electron transport material for organic electroluminescent elements concerning the other aspect of this invention contains the cyclic azine compound shown by the said General formula (1).

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

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

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

In general formula (1),
Each Ar ¹ independently represents a phenyl group, a naphthyl group or a pyridyl group;
Ar ² is
A single ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
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, which is composed of an atom selected from the group consisting of H, C, O, and S, or
Represents a hydrogen atom;
A represents a group represented by the general formula (2) or the general formula (3);

In the general formula (2) and the 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 a bonding position;
L ¹ represents a divalent or trivalent phenyl group, a naphthyl group, a 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 identical or different from each other;
When n is 2, two L ³ may be identical or different from each other;
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 methyl pyridyl group, a dimethyl pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms It may be done.

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

[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 a fluorine atom, a methyl group or a phenyl group.
The fluorine atom-substituted phenyl group, naphthyl group or pyridyl group in Ar ¹ is not particularly limited, and examples thereof include fluorophenyl group, pentafluorophenyl group, difluorophenyl group, fluoronaphthyl group, Preferred examples include difluoronaphthyl group, fluoropyridyl group, difluoropyridyl group and the like.
The methyl group-substituted phenyl group, naphthyl group or pyridyl group in Ar ¹ is not particularly limited, and examples thereof include tolyl group, methylnaphthyl group, dimethylphenyl group, dimethylnaphthyl group and methylpyridyl group. Preferred examples include a group, a dimethyl pyridyl group and the like.
The phenyl group substituted by a phenyl group, a naphthyl group or a pyridyl group in 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. A group etc. are mentioned as a preferable example.

Ar ¹ is more preferably 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 identical to or different from one another.

Specific examples of Ar ¹ include, but are not particularly limited to, each independently, for example, phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3 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-phenylnaphthalen-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalene- 4-yl group, 1-phenylnaphthalen-5-yl group, 1-phenylnaphthalen-6-yl group, 1-phenylnaphthalen-7-yl group, 1-phenylnaphtha Ren-8-yl group, 2-phenylnaphthalen-1-yl group, 2-phenylnaphthalen-3-yl group, 2-phenylnaphthalen-4-yl group, 2-phenylnaphthalen-5-yl group, 2-phenyl Naphthalene-6-yl group, 2-phenylnaphthalen-7-yl group, 2-phenylnaphthalen-8-yl group, 1-methylnaphthalen-4-yl group, 1-methylnaphthalen-5-yl group, 1-methyl Naphthalene-6-yl group, 1-methylnaphthalen-7-yl group, 1-methylnaphthalen-8-yl group, 2-methylnaphthalen-1-yl group, 2-methylnaphthalen-3-yl group, 2-methyl Naphthalene-4-yl group, 2-methylnaphthalen-5-yl group, 2-methylnaphthalen-6-yl group, 2-methylnaphthalen-7-yl group, 2-methylnaphthalene- -Yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-methylpyridin-3-yl, 2-methylpyridin-4-yl, 2-methylpyridin-5-yl, 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-dimethylpyridine- 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 -Phenylpyridine-6-i 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 And 3-phenylpyridin-4-yl, 2-phenylpyridin-4-yl and the like are mentioned as preferable examples. Among these substituents, each independently a phenyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, a 2-naphthyl group, and a 2-naphthyl group in that they have excellent electron transporting material properties. The pyridyl group, 3-pyridyl group or 4-pyridyl group is more preferable.

[About Ar ² ]
Ar ² is
(I) an aromatic hydrocarbon group having 6 to 24 carbon atoms which is a single ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked;
(Ii) a single ring which may be linked, a condensed ring which may be linked, or a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting of only a 6-membered ring which is a structure in which these are linked;
(Iii) A single ring which may be linked, a condensed ring which may be linked, or an atom selected from the group consisting of H, C, O and S which is a structure in which these are linked A heteroaromatic group having 3 to 25 carbon atoms; or
(Iv) represents a hydrogen atom.
Each group of (i) to (iii) represented by Ar ² is a phenyl group, a tolyl group, a pyridyl group, a methyl pyridyl group, a dimethyl pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or a carbon number It may have 1 to 4 alkoxy groups.
p is 0 or 1.

  The aromatic hydrocarbon group of (i) is not particularly limited, and examples thereof include 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 etc. are mentioned as a preferable example. As described above, these substituents (aromatic hydrocarbon groups) are a phenyl group, a tolyl group, a pyridyl group, a methyl pyridyl group, a dimethyl pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or carbon It may be substituted by the alkoxy group of the number 1-4.

  The nitrogen-containing heteroaromatic group of (ii) is not particularly limited. For example, pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, quinolyl group, isoquinolyl group, phenanthridyl group, benzoquinolyl group And acridinyl group etc. are mentioned as a preferable example. In addition, heteroaromatic groups (for example, carbazolyl group etc.) containing a 5-membered ring are not contained in (ii) nitrogen-containing heteroaromatic groups, and are not contained in the cyclic amine compound shown by General formula (1). In addition, as described above, these substituents (nitrogen-containing heteroaromatic group) are a phenyl group, a tolyl group, a pyridyl group, a methyl pyridyl group, a dimethyl pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or It may be substituted by a C1-C4 alkoxy group.

  The heteroaromatic group of (iii) 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. Is a preferred example. As described above, these substituents (heteroaromatic groups) may be a phenyl group, a tolyl group, a pyridyl group, a methyl pyridyl group, a dimethyl pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or a carbon number It may be substituted by 1 to 4 alkoxy groups.

The alkyl group having 1 to 4 carbon atoms in Ar ² is not particularly limited, and preferred examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group and a t-butyl group. An example is given.

The alkoxy group having 1 to 4 carbon atoms in Ar ² is not particularly limited, and examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group and a t-butoxy group. Preferred examples are given.

Ar ² is preferably a group selected from any of (i) to (iii) which does not have a substituent, or (iv) a hydrogen atom, and does not have a substituent because the glass transition temperature is high. It is more preferable that it is a group selected from any of (i) to (iii).

Specifically, Ar ² is a hydrogen atom; a phenyl group, a tolyl group, a pyridyl group, a methyl pyridyl group, a dimethyl pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms Phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, benzofluorenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, chrysenyl, acenaphthyl, pyrimidyl, which may be substituted. Among them, pyrazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuryl group, benzothienyl group, dibenzofuryl group and dibenzothienyl group are preferable, and among them, ones other than hydrogen atom are preferable. Ar ² represents phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, benzofluorenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, pyrimidyl, pyrazyl, pyridyl, quinolyl More preferably, it is 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, is not particularly limited, for example, groups such as shown below (1) to (41) are preferred examples.

  (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 group 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 6-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-dimethylpyridine- 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-phenylpyridine-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 group -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) group ) 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- (4-methyl-2-pyridyl) phenyl group) 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- (5-methyl-3-pyridyl) phenyl group) 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, 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 -Phenylphenanthrene-4-yl group, 1-phenylphenanthrene-5-yl group, 1-phenylphenanthrene-6-yl group, 1-phenylphenanthrene-7-yl group, 1-phenylphenanthrene-8-yl group, 1 -Phenylphenanthrene-9-yl group, 1-phenylphenanthrene-10-yl group, 2-phenylphenanthrene-1-yl group, 2-phenylphenanthrene-3-yl group, 2-phenylphenanthrene-4-yl group, 2 -Phenylphenanthren-5-yl group, 2-phenylphenanthrene 6-yl group, 2-phenylphenanthrene-7-yl group, 2-phenylphenanthrene-8-yl group, 2-phenylphenanthrene-9-yl group, 2-phenylphenanthrene-10-yl group, 3-phenylphenanthrene- 1-yl group, 3-phenylphenanthrene-2-yl group, 3-phenylphenanthrene-4-yl group, 3-phenylphenanthrene-5-yl group, 3-phenylphenanthrene-6-yl group, 3-phenylphenanthrene- 7-yl group, 3-phenylphenanthrene-8-yl group, 3-phenylphenanthrene-9-yl group, 3-phenylphenanthrene-10-yl group, 4-phenylphenanthrene-1-yl group, 4-phenylphenanthrene- 2-yl group, 4-phenylphenanthren-3-yl group, 4-fe Ruphenanthrene-5-yl group, 4-phenylphenanthrene-6-yl group, 4-phenylphenanthrene-7-yl group, 4-phenylphenanthrene-8-yl group, 4-phenylphenanthrene-9-yl group, 4-phenylphenanthrene-9-yl group Phenylphenanthrene-10-yl group, 1-methylphenanthrene-2-yl group, 1-methylphenanthrene-3-yl group, 1-methylphenanthrene-4-yl group, 1-methylphenanthrene-5-yl group, 1-methylphenanthrene-4-yl group Methylphenanthrene-6-yl group, 1-methylphenanthrene-7-yl group, 1-methylphenanthrene-8-yl group, 1-methylphenanthrene-9-yl group, 1-methylphenanthrene-10-yl group, 2- Methylphenanthren-1-yl group, 2-methylphenanthren-3-yl group, 2-methylphen Nanthrene-4-yl group, 2-methylphenanthrene-5-yl group, 2-methylphenanthrene-6-yl group, 2-methylphenanthrene-7-yl group, 2-methylphenanthrene-8-yl group, 2-methylphenanthrene-8-yl group Phenanthrene-9-yl group, 2-methylphenanthrene-10-yl group, 3-methylphenanthrene-1-yl group, 3-methylphenanthrene-2-yl group, 3-methylphenanthrene-4-yl group, 3-methylphenanthrene Phenanthrene-5-yl group, 3-methylphenanthrene-6-yl group, 3-methylphenanthrene-7-yl group, 3-methylphenanthrene-8-yl group, 3-methylphenanthrene-9-yl group, 3-methyl Phenanthrene-10-yl group, 4-methylphenanthrene-1-yl group, 4-methylphenanthrene-2- Group, 4-methylphenanthrene-3-yl group, 4-methylphenanthrene-5-yl group, 4-methylphenanthrene-6-yl group, 4-methylphenanthrene-7-yl group, 4-methylphenanthrene-8- Group, 4-methylphenanthrene-9-yl group, 4-methylphenanthrene-10-yl group.

  (7): 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenylanthracene-2-yl group, 1-phenylanthracene-3-yl group, 1-phenylanthracene-4-yl group, 1 1-phenylanthracene-5-yl group, 1-phenylanthracene-6-yl group, 1-phenylanthracene-7-yl group, 1-phenylanthracene-8-yl group, 1-phenylanthracene-9-yl group, 1 -Phenylanthracene-10-yl group, 2-phenylanthracene-1-yl group, 2-phenylanthracene-3-yl group, 2-phenylanthracene-4-yl group, 2-phenylanthracene-5-yl group, 2 -Phenylanthracene-6-yl group, 2-phenylanthracene-7-yl group, 2-phenylanthracene-8-i Group, 2-phenylanthracene-9-yl group, 2-phenylanthracene-10-yl group, 9-phenylanthracene-1-yl group, 9-phenylanthracene-2-yl group, 9-phenylanthracene-3-yl group Group, 9-phenylanthracene-4-yl group, 9-phenylanthracene-5-yl group.

  (8): 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 1-phenylpyrene-2-yl group, 1-phenylpyrene-3-yl group, 1-phenylpyrene-4-yl group, 1 -Phenylpyren-5-yl group, 1-phenylpyrene-6-yl group, 1-phenylpyrene-7-yl group, 1-phenylpyren-8-yl group, 1-phenylpyren-9-yl group, 1 -Phenylpyrene-10-yl group, 2-phenylpyrene-1-yl group, 2-phenylpyrene-3-yl group, 2-phenylpyrene-4-yl group, 2-phenylpyren-5-yl group, 2 -Phenylpyrene-6-yl group, 2-phenylpyrene-7-yl group, 2-phenylpyrene-8-yl group, 2-phenylpyren-9-yl group, 2-phenylpyrene-10-yl group, 9 -Phenylpyrene-1-yl group 9-phenylpyrene-2-yl group, 9-phenylpyrene-3-yl group, 9-phenylpyrene-4-yl group, 9-phenylpyren-5-yl group, 9-phenylpyren-6-yl group, 9-phenylpyrene-7-yl group, 9-phenylpyrene-8-yl group, 9-phenylpyrene-10-yl group, 1-methylpyrene-2-yl group, 1-methylpyrene-3-yl group, 1- Methyl pyrene-4-yl group, 1-methyl pyren-5-yl group, 1-methyl pyren-6-yl group, 1-methyl pyren-7-yl group, 1-methyl pyren-8-yl group, 1-methyl pyren-9-yl group Group, 1-methylpyrene-10-yl group, 2-methylpyrene-1-yl group, 2-methylpyren-3-yl group, 2-methylpyren-4-yl group, 2-methylpyren-5-yl group, 2-methyl pyrene -6-yl group, 2-methylpyrene-7-yl group, 2-methylpyrene-8-yl group, 2-methylpyren-9-yl group, 2-methylpyrene-10-yl group, 9-methylpyrene-1-yl group 9-Methylpyrene-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-methylpyrene-8-yl group, 9-methylpyrene-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- Yl, fluoranthene-7-yl, fluoranthene-8-yl, fluoranthene-9-yl, fluoranthene-10-yl.

  (10): Triphenylene-1-yl group, triphenylene-2-yl group, acenaphthyl-1-yl group, acenaphthyl-3-yl group, acenaphthyl-4-yl group, acenaphthyl-5-yl group, chrysene-1-yl group 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, quinoxaline-2-yl group, quinoxaline-5-yl group, quinoxaline-6-yl group, quinazoline-2-yl group Group, quinazoline-4-yl group, quinazoline-5-yl group, quinazoline-6-yl group, quinazoline-7-yl group, quinazoline-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-dipheny group Pyrimidin-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, 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, phenanthridine-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] quinoline- 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 Phen-2-yl group, 2-methylthiophen-3-yl group, 4-methylthiophen-3-yl group, 5-methylthiophen-3-yl group, 3-methylfuran-2-yl group, 4-methylpheny 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-methylbenzothiophene-3- group , 7-methylbenzothiophen-3-yl, 2-methylbenzothiophen-4-yl, 3-methylbenzothiophen-4-yl, 5-methylbenzothiophen-4-yl, 6-methyl Benzothiophen-4-yl, 7-methylbenzothiophen-4-yl, 2-methylbenzothiophen-5-yl, 3-methylbenzo Ophen-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, 2-methylbenzofuran-4-yl, 3-methylbenzofuran-4-yl, 5-methylbenzofuran-4-yl, 6-methylbenzofuran-4-yl, 7-methylbenzofuran-4 -Yl, 2-methylbenzofuran-5-yl, 3-methylbenzofuran-5-yl, 4-methylbenzofuran-5-yl, 6-methyl 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-methyldibenzothiophene-2-one , 4-methyldibenzothiophen-2-yl, 6-methyldibenzothiophen-2-yl, 7-methyldibenzothiophen-2-yl, 8-methyldibenzothiophen-2-yl, 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, 6-methyldibenzofuran-2-yl, 7-methyldibenzofuran-2-yl, 8-methyldibenzofuran-2-yl, 9-methyldibenzofuran-2-yl, 1-methyldibenzofuran-3 -Yl group, 2-methyldibenzofuran-3-yl group, 4-methyldibenzofuran-3-yl group, 6-methyl group 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-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- , 7-phenylbenzothiophen-3-yl, 2-phenylbenzothiophen-4-yl, 3-phenylbenzothiophen-4-yl, 5-phenylbenzothiophen-4-yl, 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, 2-phenylbenzofuran-4-yl, 3-phenylbenzofuran-4-yl, 5-phenylbenzofuran-4-yl, 6-phenylbenzofuran-4-yl, 7-phenylbenzofuran-4 -Yl, 2-phenylbenzofuran-5-yl, 3-phenylbenzofuran-5-yl, 4-pheny 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- Phenyl dibenzo thiophen 1-yl group, 8-phenyl di benzo thiophen 1-1 -yl group, 9-phenyl di benzo thiophen 1-1-yl group, 1-phenyl dibenzo thiophen 2-yl group, 3-phenyl dibenzo thiophen 2-2 , 4-phenyldibenzothiophen-2-yl, 6-phenyldibenzothiophen-2-yl, 7-phenyldibenzothiophen-2-yl, 8-phenyldibenzothiophen-2-yl, 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 group, 7-phenyldibenzothiophen-3-yl group, 8-phenyldibenzothiophene group -3-yl group, 9-phenyl dibenzothiophen-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, 8-phenyldibenzofuran-1-yl, 9-phenyldibenzofuran-1-yl, 1-phenyldibenzofuran-2-yl, 3-phenyldibenzofuran-2-yl, 4-phenyldibenzofuran-2 -Yl, 6-phenyldibenzofuran-2-yl, 7-phenyldibenzofuran-2-yl, 8-phenyldibenzofuran-2-yl, 9-phenyldibenzofuran-2-yl, 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) group ) 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) group ) Benzothiophene-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) benzothiophene-6-yl group, 7- (2-pyridyl) benzothiophen-6-yl group, 2- (2-pyridyl) benzothiophen-7-yl group, 3- (2-pyridyl) bee 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 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 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) group ) 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 Dyl) 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) group 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) dibenzothiophene-2 -Yl group, 6- (2-pyridyl) dibenzothiophen-2-yl group, 7- (2-pyridyl) dibenzothiophen-2-yl group, 8- (2-pyridyl) dibenzothio group En-2-yl group, 9- (2-pyridyl) dibenzothiophen-2-yl group, 1- (2-pyridyl) dibenzothiophen-3-yl group, 2- (2-pyridyl) dibenzothiophene-3- -Yl, 4- (2-pyridyl) dibenzothiophen-3-yl, 6- (2-pyridyl) dibenzothiophen-3-yl, 7- (2-pyridyl) dibenzothiophen-3-yl, 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) group ) 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) group ) 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 -( -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) benzothiophene-6-yl group, 7- (3-pyridyl) benzothiophen-6-yl group, 2- (3-pyridyl) benzothiophen-7-yl group, 3- (3-pyridyl) bee 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 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 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) group ) 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 Dyl) 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) group 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) dibenzothiophene-2 -Yl, 6- (3-pyridyl) dibenzothiophen-2-yl, 7- (3-pyridyl) dibenzothiophen-2-yl, 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) dibenzothiophene-3- -Yl, 4- (3-pyridyl) dibenzothiophen-3-yl, 6- (3-pyridyl) dibenzothiophen-3-yl, 7- (3-pyridyl) dibenzothiophen-3-yl, 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) group ) 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 -( -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) benzothiophene-6-yl group, 7- (4-pyridyl) benzothiophen-6-yl group, 2- (4-pyridyl) benzothiophen-7-yl group, 3- (4-pyridyl) bee 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 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 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) group ) 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 Dyl) 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) group 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) dibenzothiophene-2 -Yl, 6- (4-pyridyl) dibenzothiophen-2-yl, 7- (4-pyridyl) dibenzothiophen-2-yl, 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) dibenzothiophene-3- -Yl, 4- (4-pyridyl) dibenzothiophen-3-yl, 6- (4-pyridyl) dibenzothiophen-3-yl, 7- (4-pyridyl) dibenzothiophen-3-yl, 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) group ) 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-phenylanthracene-9-yl group, 10- (2-pyridyl) -anthracene-9-yl group, 10- (3-pyridyl) ) -Anthracene-9-yl group, 10- (4-pyridyl) -anthracene-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, in terms of excellent electron transporting material properties. -(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-phenylpyridine-6 -Yl, 2,6-diphenylpyridin-4-yl, 4,6-diphenylpyridin-2-yl, 2-pyrimidyl, 2-pyrazyl, 1-naphthyl, 2-naphthyl, 3- Quinolyl , 4-quinolyl group, 3-isoquinolyl group, 2-benzothienyl group, 2-benzofuryl group, 2-fluorenyl group, 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-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, 3- The fluoranthenyl group, 1-pyrenyl group, 2-triphenylenyl group etc. are preferable.

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, 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-pyrazinyl 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, 9-phenanthryl group, 3-fluoranthenyl group, 1-pyrenyl group, or 2-triphenylenyl group More preferable.

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

In the general formula (2) and the general formula (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 a fluorine atom, a methyl group or a phenyl group.
Ar ³ is preferably a hydrogen atom in that it is easy to synthesize.
* Represents a bonding position.

[About L ¹ ]
L ¹ represents a divalent or trivalent phenyl group, a naphthyl group, a pyridyl group or a single bond. These groups may be substituted with a fluorine atom, a methyl group or a phenyl group.
Among these groups, L ¹ is preferably each independently a divalent or trivalent phenyl group, a pyridyl group, or a single bond from the viewpoint of easy availability of the raw material, and is preferably divalent or trivalent. More preferably, it is a phenyl group of or a single bond.

[About 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 a fluorine atom, a methyl group or a phenyl group.
Among these groups, L ² and L ³ are more preferably each independently a phenylene group, a naphthylene group, or a pyridylene group which does not have a substituent, in terms of easy availability of raw materials.
m and n represent 0, 1 or 2; When m is 2, two L ² may be identical or different from each other. When n is 2, two L ³ may be identical or different from each other.

When the cyclic azine compound (1) is used as part of the constituent components of an organic electroluminescent device (OLED; Organic Light Emitting Diode), effects such as higher luminous efficiency and longer lifetime can be obtained. In particular, when the cyclic azine compound (1) is used as the electron transport layer, these effects are more exhibited.
Among the compounds represented by the general formula (1), the following (A-1) to (A-728) can be exemplified as specific examples of particularly preferable compounds, but the cyclic azine compound according to one aspect of the present invention 1) is not limited to these.

  Hereinafter, applications of the cyclic azine compound (1) will be described.

<Material for organic electroluminescent device, electron transport material for organic electroluminescent device>
Although a cyclic azine compound (1) is not specifically limited, For example, it can be used as a material for organic electroluminescent elements. Moreover, cyclic azine compound (1) can be used as an electron transport material for organic electroluminescent elements, for example.
That is, the material for an organic electroluminescent element according to one aspect of the present invention contains a cyclic azine compound (1). The electron transport material for an organic electroluminescent device according to one aspect of the present invention includes a cyclic azine compound (1). The material for an organic electroluminescent device containing the cyclic azine compound (1) and the electron transporting material for an organic electroluminescent device contribute to the production of an organic electroluminescent device excellent in durability and current efficiency.

<Organic electroluminescent device>
The organic electroluminescent device according to one aspect of the present invention comprises a cyclic azine compound (1).
Although it does not specifically limit about the structure of an organic electroluminescent element, For example, the structure of (i)-(vi) shown below is mentioned.

(I): anode / light emitting layer / cathode
(Ii): anode / hole transport layer / light emitting layer / cathode
(Iii): anode / 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 electroluminescent device according to one aspect of the present invention will be described in more detail with reference to FIG. 1 by taking the configuration of (vi) as an example.
FIG. 1 is a schematic cross-sectional view showing an example of a laminated structure of an organic electroluminescent device containing a cyclic azine compound according to one embodiment of the present invention.

  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 is omitted, and the hole transport layer 5 is directly provided on the hole injection layer 3. It is also good. In addition, for example, a single layer having a combination of functions of a plurality of layers, such as an electron injection / transport layer having the function of the electron injection layer and the function of the electron transport layer in a single layer, It may be a configuration provided instead of Furthermore, for example, a single-layer hole transport layer 5 and a single-layer electron transport layer 7 may each be composed of a plurality of layers.

[Layer containing cyclic azine compound represented by general formula (1)]
The organic electroluminescent device contains the cyclic azine compound represented by the above general 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 includes the cyclic azine compound (1) in at least one layer selected from the group consisting of the light emitting layer 6 and the electron transporting layer 7. In particular, the electron transport layer 7 preferably contains a cyclic azine compound (1). The cyclic azine compound (1) may be contained in a plurality of layers provided in the organic electroluminescent device, and in the case where an electron injecting layer is provided between the electron transporting layer and the cathode, the electron injecting layer is The cyclic azine compound (1) may be included.
Hereinafter, the organic electroluminescent device 100 in which the electron transport layer 7 includes the cyclic azine compound (1) will be described.

[Substrate 1]
There is no limitation in particular as a board | substrate, For example, a glass plate, a quartz plate, a plastic plate etc. are mentioned. In addition, in the configuration in which light emission is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.

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

[Anode 2]
An anode 2 is provided on the substrate 1 (the hole injection layer 3 side).
In the case of an organic electroluminescent device configured to emit light through the anode, the anode is formed of a material that transmits or substantially transmits the light.

The transparent material used for the anode is not particularly limited. For example, 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 Can be mentioned.
In the case of an organic electroluminescent device configured to extract light only from the cathode side, the transmission characteristics of the anode are not important. Therefore, gold, iridium, molybdenum, palladium, platinum etc. are mentioned as an example of the material used for the anode in this case.

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

[Hole Injection Layer 3, Hole Transport Layer 5]
Between the anode 2 and a light emitting layer 6 described later, 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.

  The hole injecting layer and the hole transporting layer have a function of transferring holes injected from the anode to the light emitting layer, and the hole injecting layer and the hole transporting layer are interposed between the anode and the light emitting layer Thereby, more holes are injected into the light emitting layer at a lower electric field.

  The hole injection layer and the hole transport layer also function as an electron barrier layer. 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 due to the barrier of the electrons present at the interface between the light emitting layer and the hole injection layer and / or the hole transport layer Leakage to 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, and an effect such as improvement of the light emitting efficiency is brought about, and an organic electroluminescent device excellent in light emitting performance can be obtained.

  Materials of the hole injection layer and the hole transport layer are those having at least one of a hole injection property, a hole transport property, and an electron barrier property. The materials of 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 the hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone Derivative, oxazole derivative, styrylanthracene derivative, fluorenone derivative, hydrazone derivative, stilbene derivative, silazane derivative, aniline based copolymer, conductive polymer oligomer (especially thiophene oligomer), porphyrin compound, aromatic tertiary amine compound, styryl An amine compound etc. are mentioned. 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, 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) quadriphenyl N, N, N-tri (p-tolyl) amine, 4- (di-p-tolylamino) -4 '-[4- (di-p-tolylamino) styryl] stilbene, 4-N, N-diphenylamino -(2-Diphenylvinyl) benzene, 3-methoxy-4'-N, N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] And biphenyl (NPD), 4,4 ′, 4 ′ ′-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (MTDATA) and the like. .

  In addition, inorganic compounds such as p-type-Si and p-type-SiC can also be mentioned as an example 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 or two or more materials, or may have a laminated structure made of a plurality of 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.
The material of the charge generation layer is not particularly limited. For example, dipyrazino [2,3-f: 2 ′, 3′-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT -CN) is mentioned.

  The charge generation layer may have a single layer structure made of one or two or more materials, or may have a laminated structure made of a plurality of layers of 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.
As a material of the light emitting layer, a phosphorescent light emitting material, a fluorescent light emitting material, a thermally activated delayed fluorescent light emitting material can be mentioned. In the light emitting layer, electron-hole pairs recombine, resulting in light emission.
The light emitting layer may consist of a single low molecular weight material or a single polymer material, but more generally 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.

  As the fluorescent dopant, for example, anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylene pyran compound, thiopyran compound, polymethine compound, pyrilium, thiapyrilium compound, fluorene derivative, periflanthene derivative, indenoperylene Derivatives, bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, carbostyril compounds and the like can be mentioned. 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 Alq 3 (tris (8-hydroxyquinoline) aluminum), DPAVBi (4,4′-bis [4- (di-p-tolylamino) styryl] biphenyl), perylene, bis [4 2- (4-n-Hexylphenyl) quinoline] (acetylacetonate) iridium (III), Ir (PPy) 3 (tris (2-phenylpyridine) iridium (III)), and FIrPic (bis (3,5-) And difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III))) and the like.

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

  The light emitting layer may have a single layer structure made of one 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.

[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 transferring 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 with a lower electric field.

It is preferable that an electron carrying layer contains the cyclic azine compound represented by the said General formula (1) as mentioned above.
In addition to the cyclic azine compound (1), the electron transporting layer may further contain a conventionally known electron transporting material. Conventionally known electron transport materials include, for example, lithium 8-hydroxyquinolinate (Liq), bis (8-hydroxyquinolinate) zinc, bis (8-hydroxyquinolinate) copper, bis (8-hydroxyquinolinate) Nath) Manganese, tris (8-hydroxyquinolinate) aluminum, tris (2-methyl-8-hydroxyquinolinate) aluminum, tris (8-hydroxyquinolinate) gallium, bis (10-hydroxybenzo [h] Quinolinate) beryllium, bis (10-hydroxybenzo [h] quinolinate) zinc, bis (2-methyl-8-quinolinate) chlorogallium, bis (2-methyl-8-quinolinate) (o-cresolate) gallium, bis (2 -Methyl-8-quinolinate) -1-naphtholate aluminum, Or bis (2-methyl-8-quinolinate) -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-1,3,6 5-triazine, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2-methyl-8-) And quinolinolato) -4- (phenylphenolate) aluminum), and bis (10-hydroxybenzo [h] quinolinate) beryllium) and the like.

The electron transporting 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.
When the electron transport layer has a two-layer structure in which the light emitting layer side is a first electron transport layer and the cathode side is a second electron transport layer, the second electron transport layer preferably contains a cyclic azine compound (1).

[Cathode 8]
A cathode 8 is provided on the electron transport layer 7.
In the case of the organic electroluminescent element of the structure from which only the light emission which passed the anode is taken out, a cathode can be formed from arbitrary electroconductive materials.

Materials of 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]
Each layer other than the electrodes (anode, cathode) described above may be made of, for example, a vacuum deposition method, a spin coating method, a casting method, LB (the material of each layer (with a material such as a binder resin and a solvent as needed). It can be formed by thinning by a known method such as the Langmuir-Blodgett method). Although there is no restriction | limiting in particular about the film thickness of each layer, Usually, they are 5 nm-about 5 micrometers.

  There is no restriction | limiting in particular about the film thickness of each layer formed in this way, Although it can select suitably according to a condition, Usually, it is the range of 5 nm-5 micrometers.

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

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

  The organic electroluminescent device according to one aspect of the present invention may be used as a kind of lamp such as an illumination light or an exposure light source, a projection device of a type that projects an image, or direct visual recognition of a still image or a moving image. It may be used as a display of the following type. When used as a display device for moving image reproduction, either a simple matrix (passive matrix) method or an active matrix method may be used as a driving method. In addition, a full color display device can be manufactured by using two or more kinds of the organic electroluminescent elements of this embodiment having different luminescent 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 and the like).

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

¹ H-NMR measurement was performed using Gemini 200 (manufactured by Varian).

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

  Synthetic Example 1

  Under an argon stream, 4,6-diphenyl-2- [3- (9-phenanthryl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl]- 1,3,5-Triazine (6.00 g, 9.81 mmol), 4-chlorophenylphenyl sulfone (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). To this was added 2 M aqueous potassium carbonate solution (15.0 mL, 30.0 mmol) and 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 obtained concentrate, stirred at room temperature, and the precipitated solid was separated by filtration. The resulting solid was washed with water (30 mL), methanol (30 mL), hexane (30 mL). The 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 target liquid of 4,6-diphenyl-2- [5- (9-phenanthryl) -4'-phenylsulfinyl is obtained by purifying the solid obtained by drying this concentrated solution with recrystallization (toluene) once. White solid (yield 6.12 g, 89% yield) of biphenyl-3-yl] -1,3,5-triazine (compound A-5) was obtained.

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

Next, element evaluation will be described.
Structural formulas of compounds used for element evaluation and their abbreviations are shown below.

Element Example 1 (see FIG. 2)
(Preparation of substrate 1 and anode 2)
As a substrate having an anode on the surface, a glass substrate with an ITO transparent electrode in which an indium-tin oxide (ITO) film (film thickness 110 nm) having a width of 2 mm was patterned in a stripe was prepared. Subsequently, the substrate was washed with isopropyl alcohol and then subjected to surface treatment by ozone ultraviolet ray washing.

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

(Preparation of hole injection layer 3)
The sublimation purified HIL was deposited to 55 nm at a rate of 0.15 nm / sec to prepare a hole injection layer.

(Preparation of Charge Generating Layer 4)
A sublimation-purified HAT was deposited to a thickness of 5 nm at a rate of 0.05 nm / sec to prepare a charge generation 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 prepare a second hole transport layer.

(Preparation of light emitting layer 6)
EML-1 and EML-2 were deposited to a thickness of 25 nm at a ratio of 95: 5 (mass ratio) 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 produce a 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 (Compound A-5) Synthesized in Synthesis Example 1 And Liq were deposited to a thickness of 25 nm at a ratio of 50:50 (mass ratio) to form a second electron transport layer 71. The deposition rate was 0.15 nm / sec.

(Production of Cathode 8)
Finally, a metal mask was disposed to be orthogonal to the ITO stripes on the substrate, and a cathode 8 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 deposition rate of silver / magnesium was 0.5 nm / sec, and the deposition rate of silver was 0.2 nm / sec.

Thus, the organic electroluminescent device 100 with a light emitting area of 4 mm ² as shown in FIG. 2 was produced. In addition, each film thickness was measured by a stylus type film thickness measurement meter (DEKTAK, manufactured by Bruker).

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

A direct current was applied to the organic electroluminescent device produced as described above, and the luminescence characteristics were evaluated using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse Co., Ltd.). As light emission characteristics, current efficiency (cd / A) was measured when a current density of 10 mA / cm ² was passed, and device lifetime (h) at continuous lighting was measured. The device life (h) in Table 1 was measured by measuring the luminance decay time during continuous lighting when the manufactured device was driven at an initial luminance of 1000 cd / m ² , until the luminance (cd / m ² ) decreased by 15%. The time taken for the The voltage, current efficiency, and 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 Reference Example-1
In the element example-1, in place of the compound A-5, 2- [5- (9-phenanthryl) -3- (3-pyridyl) phenyl] -4,6-diphenyl-1 described in Patent Document 1 The organic electroluminescent element was produced and evaluated by the same method as element Example 1 except having used 3, and 3,5- triazine (ETL-2). 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 film quality, and by using the compound, an organic electroluminescent device excellent in long life and luminous efficiency can be provided.

  In addition, the cyclic azine compound (1) according to one aspect of the present invention is used as an electron transport material for an organic electroluminescent device which is excellent in low driving voltage. Furthermore, according to the cyclic azine compound (1), an organic electroluminescent device with low power consumption can be provided.

  In addition, the cyclic azine compound according to one aspect of the present invention has excellent thermal stability during sublimation purification, and is excellent in operability of sublimation purification, and provides a material with few impurities that cause deterioration of the organic electroluminescent device. can do. Moreover, since the cyclic azine compound concerning 1 aspect of this invention is excellent in the stability of a vapor deposition film, the long life organic electroluminescent element can be provided.

  In addition, the thin film formed of the cyclic azine compound (1) according to one aspect of the present invention is excellent in electron transportability, hole blocking ability, redox resistance, water resistance, oxygen resistance, electron injection characteristics, etc. It is useful as a material of the device, and useful as an electron transporting material, a hole blocking material, a light emitting host material, and the like. It is particularly useful when used as an electron transport material.

  In addition, since the cyclic azine compound (1) according to one aspect of the present invention has a wide band gap and a high triplet excitation level, it can be used not only for conventional fluorescent devices but also for phosphorescent devices and thermally activated delayed fluorescence ( It can use suitably for the organic electroluminescent element using TADF).

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 Electroluminescent Device

Claims (8)

Cyclic azine compounds represented by the general formula (1):

In general formula (1),
Each Ar ¹ independently represents a phenyl group, a naphthyl group or a pyridyl group;
Ar ² is
A single ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
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, which is composed of an atom selected from the group consisting of H, C, O, and S, or
Represents a hydrogen atom;
A represents a group represented by the general formula (2) or the general formula (3);

In the general formula (2) and the 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 a bonding position;
L ¹ represents a divalent or trivalent phenyl group, a naphthyl group, a 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 identical or different from each other;
When n is 2, two L ³ may be identical or different from each other;
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 methyl pyridyl group, a dimethyl pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms It may be done. The cyclic azine compound according to claim 1, wherein Ar ¹ is each independently a phenyl group, a naphthyl group, a biphenyl group or a pyridyl group. Ar ² is
A phenyl group, a tolyl group, a pyridyl group, a methyl pyridyl group, a dimethyl pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; , 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, benzofuryl group, benzothienyl group Group, dibenzofuryl group, dibenzothienyl group, or
The cyclic azine compound according to claim 1 or 2, which is a hydrogen atom. The cyclic azine compound according to any one of claims 1 to 3, wherein L ¹ is a divalent or trivalent phenyl group or a single bond. The cyclic azine compound according to any one of claims 1 to 4, wherein L ² and L ³ are each independently a phenylene group, a naphthylene group, or a pyridylene group having no substituent. Cyclic azine compound according to any one of claims 1 to 5 Ar ³ is a hydrogen atom.   The material for organic electroluminescent elements containing the cyclic azine compound shown by General formula (1) of any one of Claims 1-6.   The electron transport material for organic electroluminescent elements containing the cyclic azine compound shown by General formula (1) of any one of Claims 1-6.

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