JP2020094031A - Cyclic azine compound, material for organic electroluminescent element, electron transport material for organic electroluminescent element, and organic electroluminescent element - Google Patents

Abstract

To provide a cyclic azine compound having excellent current efficiency and a long service life.SOLUTION: A cyclic azine compound has a specific structure with an aromatic ring and a heterocycle bound to triazine.SELECTED DRAWING: Figure 1

Description

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

The organic electroluminescence device is used not only for a small display but also for a large-sized television, lighting, and the like, and its development has been vigorously carried out.
For example, Patent Document 1 discloses, as a material for an organic electroluminescent device, a cyclic azine compound having a specific substituent, which contributes to the provision of an organic electroluminescent device having excellent heat resistance, reduced driving voltage, and long life. There is.
Patent Document 2 discloses a cyclic azine compound having a diarylpyridine structure.

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

However, in recent years, the market demand for organic electroluminescent devices has increased more and more, and materials having excellent current efficiency characteristics, driving voltage characteristics, and long life characteristics are required.
Here, although the organic electroluminescent device using the cyclic azine compound disclosed in Patent Documents 1 and 2 exhibits excellent driving voltage characteristics, further improvement is required for the device life and current efficiency. ..

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

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

In formula (1),
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenyl group, or a naphthyl group;
X ^{1 to} X ⁵ each independently represent C—Ar ³ , C—R, or a nitrogen atom;
One or two of X ^{1 to} X ⁵ are nitrogen atoms;
One or 2 in X ¹ to X ⁵ is a C-Ar ^3;
Ar ³ is
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 24 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ³ is 4 to 25;
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
L ¹ represents a phenylene group or a single bond;
n ¹ represents 0, 1, or 2;
When only one of X ^{1 to} X ⁵ is C-Ar ³ and either one of X ¹ and X ⁵ is C-Ar ³ ,
L ¹ is a single bond,
n ¹ is 0 or 1;
When only one of X ^{1 to} X ⁵ is C-Ar ³ and any one of X ² , X ³ and X ⁴ is C-Ar ³ ,
L ¹ is a phenylene group or a single bond,
n ¹ is 0, 1, or 2;
When two of X ^{1 to} X ⁵ are C-Ar ³ ,
Of X ¹ , X ³ , and X ⁵ , one is a nitrogen atom and the other two are C—R,
X ² and X ⁴ are C—Ar ³ ;
L ¹ is a phenylene group or a single bond,
n ¹ is 1 or 2;
The two C—R and the two C—Ar ³ may be the same or different;
The groups represented by Ar ¹ , Ar ² and Ar ³ are each independently a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms. It may have one or more groups selected from the group consisting of a group and an alkoxy group having 1 to 4 carbon atoms.

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

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

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

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

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

In formula (1),
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenyl group, or a naphthyl group;
X ^{1 to} X ⁵ each independently represent C—Ar ³ , C—R, or a nitrogen atom;
One or two of X ^{1 to} X ⁵ are nitrogen atoms;
One or 2 in X ¹ to X ⁵ is a C-Ar ^3;
Ar ³ is
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 24 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ³ is 4 to 25;
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
L ¹ represents a phenylene group or a single bond;
n ¹ represents 0, 1, or 2;
When only one of X ^{1 to} X ⁵ is C-Ar ³ and either one of X ¹ and X ⁵ is C-Ar ³ ,
L ¹ is a single bond;
n ¹ is 0 or 1;
When only one of X ^{1 to} X ⁵ is C-Ar ³ and any one of X ² , X ³ and X ⁴ is C-Ar ³ ,
L ¹ is a phenylene group or a single bond,
n ¹ is 0, 1, or 2;
In the case where two of X ^{1 to} X ⁵ are C-Ar ³ ,
Of X ¹ , X ³ , and X ⁵ , one is a nitrogen atom and the other two are C—R,
X ² and X ⁴ are C—Ar ³ ;
L ¹ is a phenylene group or a single bond;
n ¹ is 1 or 2;
The two C—R and the two C—Ar ³ may be the same or different;
The groups represented by Ar ¹ , Ar ² and Ar ³ are each independently a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms. It may have one or more groups selected from the group consisting of a group and an alkoxy group having 1 to 4 carbon atoms.

The cyclic azine compound according to one aspect of the present invention is more preferably represented by formula (11) or formula (21):

In formula (11),
Ar ¹¹ and Ar ¹² each independently represent a phenyl group or a naphthyl group;
Ar ¹³ and Ar ¹⁴ are each independently
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 24 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ¹³ and Ar ¹⁴ is 4 to 25;
L ¹¹ represents a phenylene group or a single bond;
One of Z ¹¹ and Z ¹² represents a nitrogen atom, and the other represents C—H;
n ¹¹ is 1 or 2.
Each group represented by Ar ^{11 to} Ar ¹⁴ is independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. It may have one or more groups selected from the group consisting of 4 alkoxy groups.

Ar ¹¹ and Ar ¹² are each independently a phenyl group or a naphthyl group;
When each group represented by Ar ¹¹ and Ar ¹² is a phenyl group, the phenyl group may independently have a phenyl group.

In formula (21),
Ar ²¹ and Ar ²² each independently represent a phenyl group, a biphenyl group, or a naphthyl group;
X ^{21 to} X ²⁵ each independently represent C—Ar ²³ , C—R, or a nitrogen atom;
In X ^{21 to} X ²⁵ , one or two are nitrogen atoms;
Ar ²³ is
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 18 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ²³ is 4 to 25;
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
Only one of X ^{21 to} X ²⁵ is C-Ar ²³ ;
Among X ²¹ to X ^25, if either one of ^{X 21} and ^{X 25} are ^{C-Ar 23} is,
L ²¹ is a single bond,
n ²¹ is 0 or 1;
When any one of X ^{22 to} X ²⁴ is C—Ar ²³ among X ^{21 to} X ²⁵ ,
L ²¹ is a phenylene group or a single bond,
n ²¹ is 0, 1, or 2;
Each group represented by Ar ^{21 to} Ar ²³ may be independently substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group.

Hereinafter, the cyclic azine compound represented by formula (1), formula (11), or formula (21) may be referred to as cyclic azine compound (1), (11), or (21), respectively. The definition of the substituents in the cyclic azine compounds (1), (11), and (21), and preferable specific examples thereof are as follows.

[About Ar ¹ and Ar ² ]
In Formula (1), Ar ¹ and Ar ² each independently represent a phenyl group, a biphenyl group, or a naphthyl group. Each independently selected from the group consisting of a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. It may have one or more groups described above.
It is more preferable that Ar ¹ and Ar ² are each independently a phenyl group, a naphthyl group, or a phenyl group having a phenyl group (that is, a biphenyl group) in terms of excellent electron-transporting material properties.

[About X ^{1 to} X ⁵ , Ar ³ , and R]
X ^{1 to} X ⁵ each independently represent C—Ar ³ , C—R, or a nitrogen atom.
One or two of X ^{1 to} X ⁵ are nitrogen atoms.
One or two of X ^{1 to} X ⁵ are C-Ar ³ .

Ar ³ is
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 24 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii).
Each of the groups (i) to (iv) represented by Ar ³ is independently a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, and a carbon number of 1 to 4. May have one or more groups selected from the group consisting of an alkyl group and an alkoxy group having 1 to 4 carbon atoms. It is more preferable that Ar ³ has no substituent in terms of easy synthesis.

The aromatic hydrocarbon group (i) is not particularly limited, and examples thereof include phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, triphenylenyl group. , Chrysenyl group, perylenyl group, fluoranthenyl group, acenaphthyl group and the like are preferable examples. As described above, these substituents (aromatic hydrocarbon groups) are each independently a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, and a carbon number of 1 to 1. It may have one or more groups selected from the group consisting of a C4 alkyl group and a C1-4 alkoxy group.

The nitrogen-containing heteroaromatic group (ii) is not particularly limited, and examples thereof include pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, quinolyl group, isoquinolyl group, phenanthridyl group and benzoquinolyl group. , And acridinyl group are preferred examples. The heteroaromatic group containing a 5-membered ring (for example, a carbazolyl group) is not included in the nitrogen-containing heteroaromatic group (ii), and is not included in the cyclic azine compound represented by the formula (1). Further, as described above, these substituents (nitrogen-containing heteroaromatic group) are each independently a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, and a carbon number of 1 It may have one or more groups selected from the group consisting of an alkyl group having 4 to 4 and an alkoxy group having 1 to 4 carbon atoms.

The heteroaromatic group of (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. Are preferred examples. As described above, these substituents (heteroaromatic groups) are each independently a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, and a carbon number of 1 to 4 May have one or more groups selected from the group consisting of an alkyl group and an alkoxy group having 1 to 4 carbon atoms.

The alkyl group having 1 to 4 carbon atoms in Ar ³ is not particularly limited, but for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a t-butyl group and the like are preferable. Take as an example.

The alkoxy group having 1 to 4 carbon atoms in Ar ³ is not particularly limited, but includes a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a t-butoxy group, and the like. As a preferable example.

Specifically, Ar ³ is selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms. It may be substituted with one or more selected groups, phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, It is preferably a chrysenyl group, an acenaphthyl group, a pyrimidyl group, a pyrazyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group or a dibenzothienyl group. Ar ³ may have one or more groups selected from the group consisting of a phenyl group, a tolyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms, Phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, chrysenyl group, acenaphthyl group, benzofuryl group, benzothienyl group, dibenzofuryl group More preferably, it is a dibenzothienyl group.
In the formula (1), when two Ar ^{3 s} appear, the two Ar ^{3 s} may be the same or different from each other.

The total number of ring-constituting carbon atoms of the group represented by Ar ³ is 4 to 25 in all cases.
When Ar ³ has a substituent, the number of carbon atoms of the substituent is not included in the total number of ring-constituting carbon atoms of the group represented by Ar ³ . Therefore, for example, when the group represented by Ar ³ is a fluorene group (having 13 carbon atoms in the ring) and the group represented by Ar ³ has a phenyl group, the fluorene group having a phenyl group has these (substituent + Ar ³ ) Will have a total of 19 ring-constituting carbon atoms.
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[About L ¹ ]
L ¹ represents a phenylene group or a single bond.

[About n ¹ ]
n ¹ represents 0, 1, or 2.

From the viewpoint of easy availability of raw materials, it is preferable that only one of X ^{1 to} X ⁵ is a nitrogen atom.

When only one of X ^{1 to} X ⁵ is C-Ar ³ and either one of X ¹ and X ⁵ is C-Ar ³ ,
L ¹ is a single bond,
n ¹ is 0 or 1.
When only one of X ^{1 to} X ⁵ is C-Ar ³ and any one of X ² , X ³ and X ⁴ is C-Ar ³ ,
L ¹ is a phenylene group or a single bond,
n ¹ is 0, 1, or 2.
In the case where two of X ^{1 to} X ⁵ are C-Ar ³ ,
Of X ¹ , X ³ , and X ⁵ , one is a nitrogen atom and the other two are C—R,
X ² and X ⁴ are C—Ar ³ ;
L ¹ is a phenylene group or a single bond,
n ¹ is 1 or 2.
The two C—R and the two C—Ar ³ may be the same or different.

[About Ar ¹¹ and Ar ¹² ]
In formula (11), Ar ¹¹ and Ar ¹² each independently represent a phenyl group or a naphthyl group. One independently selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. It may have the above groups.
It is more preferable that Ar ¹¹ and Ar ¹² are each independently a phenyl group, a naphthyl group, or a phenyl group having a phenyl group (that is, a biphenyl group) in terms of excellent electron-transporting material properties.

[About Ar ¹³ and Ar ¹⁴ ]
In formula (11) and formula (1), Ar ¹³ and Ar ¹⁴ are each independently
(I) an aromatic hydrocarbon group having 6 to 24 carbon atoms, which has a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked;
(Ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms, which is composed of a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked, and which has only a 6-membered ring;
(Iii) composed of an atom selected from the group consisting of H, C, O, and S, which is a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked. A heteroaromatic group having 4 to 25 carbon atoms;
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii).
The groups (i) to (iv) represented by Ar ¹³ and Ar ¹⁴ are each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, and a carbon number of 1 to 1. It may have one or more groups selected from the group consisting of a C4 alkyl group and a C1-4 alkoxy group. It is more preferable that Ar ¹³ and Ar ¹⁴ have no substituent.

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

The nitrogen-containing heteroaromatic group (ii) is not particularly limited, and examples thereof include pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, quinolyl group, isoquinolyl group, phenanthridyl group and benzoquinolyl group. , And acridinyl group are preferred examples. Note that the heteroaromatic group containing a 5-membered ring (for example, a carbazolyl group) is not included in the (ii) nitrogen-containing heteroaromatic group, and is included in the cyclic azine compound represented by the formula (11) and the formula (1). Is not included. In addition, as described above, these substituents (nitrogen-containing heteroaromatic group) are each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, and a carbon number of 1 to 4 It may have one or more groups selected from the group consisting of an alkyl group and an alkoxy group having 1 to 4 carbon atoms.

The heteroaromatic group of (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. Are preferred examples. As described above, these substituents (heteroaromatic groups) are each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms. , And one or more groups selected from the group consisting of alkoxy groups having 1 to 4 carbon atoms.

The alkyl group having 1 to 4 carbon atoms in Ar ¹³ and Ar ¹⁴ is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and a t-butyl group. A group etc. are mentioned as a preferable example.

The alkoxy group having 1 to 4 carbon atoms in Ar ¹³ and Ar ¹⁴ is not particularly limited, but is a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a t- group. A butoxy group etc. are mentioned as a preferable example.

Specifically, Ar ¹³ and Ar ¹⁴ are each independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. 4, which may be substituted with one or more groups selected from the group consisting of alkoxy groups, phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, A fluoranthenyl group, triphenylenyl group, chrysenyl group, acenaphthyl group, pyrimidyl group, pyrazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuryl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group are preferable. Ar ¹³ and Ar ¹⁴ are 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. More preferably, it is a group, a quinolyl group, an isoquinolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a biphenyl group or a pyridylphenyl group.

Although the specific examples of the groups represented by Ar ¹³ and Ar ¹⁴ are not particularly limited, for example, the groups (1) to (44) shown below are preferable examples.

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

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

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

(4): 2-phenylpyridin-6-yl group, 3-phenylpyridin-6-yl group, 4-phenylpyridin-6-yl group, 5-phenylpyridin-6-yl group, 2-phenylpyridin-3 -Yl group, 2-phenylpyridin-5-yl group, 3-phenylpyridin-5-yl group, 4-phenylpyridin-3-yl group, 3-phenylpyridin-4-yl group, 2-phenylpyridin-4 -Yl group, 2-(2-pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 3-(3-pyridyl) ) Phenyl group, 4-(3-pyridyl)phenyl group, 2-(4-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 2-(3-methyl) -2-pyridyl)phenyl group, 3-(3-methyl-2-pyridyl)phenyl group, 4-(3-methyl-2-pyridyl)phenyl group, 2-(4-methyl-2-pyridyl)phenyl group, 3-(4-methyl-2-pyridyl)phenyl group, 4-(4-methyl-2-pyridyl)phenyl group, 2-(5-methyl-2-pyridyl)phenyl group, 3-(5-methyl-2) -Pyridyl)phenyl group, 4-(5-methyl-2-pyridyl)phenyl group, 2-(6-methyl-2-pyridyl)phenyl group, 3-(6-methyl-2-pyridyl)phenyl group, 4- (6-methyl-2-pyridyl)phenyl group, 2-(2-methyl-3-pyridyl)phenyl group, 3-(2-methyl-3-pyridyl)phenyl group, 4-(2-methyl-3-pyridyl) ) Phenyl group, 2-(4-methyl-3-pyridyl)phenyl group, 3-(4-methyl-3-pyridyl)phenyl group, 4-(4-methyl-3-pyridyl)phenyl group, 2-(5 -Methyl-3-pyridyl)phenyl group, 3-(5-methyl-3-pyridyl)phenyl group, 4-(5-methyl-3-pyridyl)phenyl group, 2-(6-methyl-3-pyridyl)phenyl Group, 3-(6-methyl-3-pyridyl)phenyl group, 4-(6-methyl-3-pyridyl)phenyl group, 2-(2-methyl-4-pyridyl)phenyl group, 3-(2-methyl) -4-pyridyl)phenyl group, 4-(2-methyl-4-pyridyl)phenyl group, 2-(3-methyl-4-pyridyl)phenyl group, 3-(3-methyl-4-pyridyl)phenyl group, 4-(3-methyl-4-pyridyl)phenyl group, 2,6-diphenylpyridin-3-yl group, 2, 6-diphenylpyridin-4-yl group, 4,6-diphenylpyridin-2-yl group, 3,6-diphenylpyridin-4-yl group, 3,6-diphenylpyridin-5-yl group.

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

(6): 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-phenylphenanthren-2-yl group, 1-phenylphenanthren-3-yl group, 1 -Phenylphenanthren-4-yl group, 1-phenylphenanthren-5-yl group, 1-phenylphenanthren-6-yl group, 1-phenylphenanthren-7-yl group, 1-phenylphenanthren-8-yl group, 1 -Phenylphenanthren-9-yl group, 1-phenylphenanthren-10-yl group, 2-phenylphenanthren-1-yl group, 2-phenylphenanthren-3-yl group, 2-phenylphenanthren-4-yl group, 2 -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 Phenanthrene-9-yl group, 2-methylphenanthren-10-yl group, 3-methylphenanthren-1-yl group, 3-methylphenanthren-2-yl group, 3-methylphenanthren-4-yl group, 3-methyl Phenanthren-5-yl group, 3-methylphenanthren-6-yl group, 3-methylphenanthren-7-yl group, 3-methylphenanthren-8-yl group, 3-methylphenanthren-9-yl group, 3-methyl Phenanthrene-10-yl group, 4-methylphenanthren-1-yl group, 4-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-phenylanthracene-7-yl group, 1-phenylanthracene-8-yl group, 1-phenylanthracene-9-yl group, 1 -Phenylanthracen-10-yl group, 2-phenylanthracen-1-yl group, 2-phenylanthracen-3-yl group, 2-phenylanthracen-4-yl group, 2-phenylanthracene-5-yl group, 2 -Phenylanthracen-6-yl group, 2-phenylanthracen-7-yl group, 2-phenylanthracene-8-yl group, 2-phenylanthracene-9-yl group, 2-phenylanthracene-10-yl group, 9 -Phenylanthracen-1-yl group, 9-phenylanthracen-2-yl group, 9-phenylanthracen-3-yl group, 9-phenylanthracen-4-yl group, 9-phenylanthracene-5-yl group, 9 A -(2-pyridyl)-anthracen-10-yl group, a 9-(3-pyridyl)-anthracen-10-yl group, a 9-(4-pyridyl)-anthracen-10-yl group.

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

(9): Fluoranthen-1-yl group, fluoranthen-1-yl group, fluoranthen-2-yl group, fluoranthen-3-yl group, fluoranthen-4-yl group, fluoranthen-5-yl group, fluoranthene-6- An yl group, a fluoranthen-7-yl group, a fluoranthen-8-yl group, a fluoranthen-9-yl group, a fluoranthen-10-yl group.

(10): triphenylen-1-yl group, triphenylen-2-yl group, acenaphthylene-1-yl group, acenaphthylene-3-yl group, acenaphthylene-4-yl group, acenaphthylene-5-yl group, chrysen-1- An yl group, a chrysen-2-yl group, a chrysen-5-yl group, a chrysen-6-yl group.

(11): 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4 -Isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, quinoxalin-2-yl group, quinoxalin-5-yl group, quinoxalin-6-yl group, quinazolin-2-yl group Group, quinazolin-4-yl group, quinazolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-8-yl group, pyrazin-2-yl group, 5-methylpyrazin-2 -Yl group, 5,6-diphenylpyrazin-2-yl group, pyrimidin-2-yl group, pyrimidin-4-yl group, pyrimidin-5-yl group, 2,4-diphenylpyrimidin-6-yl group, 4 ,6-Diphenylpyrimidin-2-yl group, acridin-1-yl group, acridine-1-yl group, acridine-2-yl group, acridine-3-yl group, acridine-4-yl group, acridine-9- Ile group, phenanthridin-1-yl group, phenanthridin-1-yl group, phenanthridin-2-yl group, phenanthridin-3-yl group, phenanthridin-4-yl group, phenanthate Lydin-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 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-methylbenzothiophen-3- Yl group, 7-methylbenzothiophen-3-yl group, 2-methylbenzothiophen-4-yl group, 3-methylbenzothiophen-4-yl group, 5-methylbenzothiophen-4-yl group, 6-methyl Benzothiophen-4-yl group, 7-methylbenzothiophen-4-yl group, 2-methylbenzothiophen-5-yl group, 3-methylbenzothiophen-5-yl group, 4-methylbenzothiophen-5-yl group 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-methyldibenzothiophen-2- Yl group, 4-methyldibenzothiophen-2-yl group, 6-methyldibenzothiophen-2-yl group, 7-methyldibenzothiophen-2-yl group, 8-methyldibenzothiophen-2-yl group, 9-methyl Dibenzothiophen-2-yl group, 1-methyldibenzothiophen-3-yl group, 2-methyldibenzothiophen-3-yl group, 4-methyldibenzothiophen-3-yl group, 6-methyldibenzothiophen-3-yl group Group, 7-methyldibenzothiophen-3-yl group, 8-methyldibenzothiophen-3-yl group, 9-methyldibenzothiophen-3-yl group.

(16): 2-methyldibenzofuran-1-yl group, 3-methyldibenzofuran-1-yl group, 4-methyldibenzofuran-1-yl group, 6-methyldibenzofuran-1-yl group, 7-methyldibenzofuran-1 -Yl group, 8-methyldibenzofuran-1-yl group, 9-methyldibenzofuran-1-yl group, 1-methyldibenzofuran-2-yl group, 3-methyldibenzofuran-2-yl group, 4-methyldibenzofuran-2 -Yl group, 6-methyldibenzofuran-2-yl group, 7-methyldibenzofuran-2-yl group, 8-methyldibenzofuran-2-yl group, 9-methyldibenzofuran-2-yl group, 1-methyldibenzofuran-3 -Yl group, 2-methyldibenzofuran-3-yl group, 4-methyldibenzofuran-3-yl group, 6-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-phenylthiophen-3 -Yl group, 5-phenylthiophen-3-yl group.

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

(19): 3-phenylbenzothiophen-2-yl group, 4-phenylbenzothiophen-2-yl group, 5-phenylbenzothiophen-2-yl group, 6-phenylbenzothiophen-2-yl group, 7- Phenylbenzothiophen-2-yl group, 2-phenylbenzothiophen-3-yl group, 4-phenylbenzothiophen-3-yl group, 5-phenylbenzothiophen-3-yl group, 6-phenylbenzothiophen-3- Yl group, 7-phenylbenzothiophen-3-yl group, 2-phenylbenzothiophen-4-yl group, 3-phenylbenzothiophen-4-yl group, 5-phenylbenzothiophen-4-yl group, 6-phenyl Benzothiophen-4-yl group, 7-phenylbenzothiophen-4-yl group, 2-phenylbenzothiophen-5-yl group, 3-phenylbenzothiophen-5-yl group, 4-phenylbenzothiophen-5-yl group 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-phenyldibenzothiophen-2- Group, 4-phenyldibenzothiophen-2-yl group, 6-phenyldibenzothiophen-2-yl group, 7-phenyldibenzothiophen-2-yl group, 8-phenyldibenzothiophen-2-yl group, 9-phenyl Dibenzothiophen-2-yl group, 1-phenyldibenzothiophen-3-yl group, 2-phenyldibenzothiophen-3-yl group, 4-phenyldibenzothiophen-3-yl group, 6-phenyldibenzothiophen-3-yl group Group, 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 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)benzothiophen-5 -Yl group, 2-(2-pyridyl)benzothiophen-6-yl group, 3-(2-pyridyl)benzothiophen-6-yl group, 4-(2-pyridyl)benzothiophen-6-yl group, 5 -(2-pyridyl)benzothiophen-6-yl group, 7-(2-pyridyl)benzothiophen-6-yl group, 2-(2-pyridyl)benzothiophen-7-yl group, 3-(2-pyridyl) ) Benzothiophen-7-yl group, 4-(2-pyridyl)benzothiophen-7-yl group, 5-(2-pyridyl)benzothiophen-7-yl group, 6-(2-pyridyl)benzothiophen-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 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)dibenzothiophen-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)dibenzothiophen-3 -Yl group, 9-(2-pyridyl)dibenzothiophen-3-yl group.

(27): 2-(2-pyridyl)dibenzofuran-1-yl group, 3-(2-pyridyl)dibenzofuran-1-yl group, 4-(2-pyridyl)dibenzofuran-1-yl group, 6-(2 -Pyridyl)dibenzofuran-1-yl group, 7-(2-pyridyl)dibenzofuran-1-yl group, 8-(2-pyridyl)dibenzofuran-1-yl group, 9-(2-pyridyl)dibenzofuran-1-yl group Group, 1-(2-pyridyl)dibenzofuran-2-yl group, 3-(2-pyridyl)dibenzofuran-2-yl group, 4-(2-pyridyl)dibenzofuran-2-yl group, 6-(2-pyridyl ) Dibenzofuran-2-yl group, 7-(2-pyridyl)dibenzofuran-2-yl group, 8-(2-pyridyl)dibenzofuran-2-yl group, 9-(2-pyridyl)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)benzothiophen-3 -Yl group, 2-(3-pyridyl)benzothiophen-4-yl group, 3-(3-pyridyl)benzothiophen-4-yl group, 5-(3-pyridyl)benzothiophen-4-yl group, 6 -(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)benzothiophen-5 -Yl group, 2-(3-pyridyl)benzothiophen-6-yl group, 3-(3-pyridyl)benzothiophen-6-yl group, 4-(3-pyridyl)benzothiophen-6-yl group, 5 -(3-pyridyl)benzothiophen-6-yl group, 7-(3-pyridyl)benzothiophen-6-yl group, 2-(3-pyridyl)benzothiophen-7-yl group, 3-(3-pyridyl ) Benzothiophen-7-yl group, 4-(3-pyridyl)benzothiophen-7-yl group, 5-(3-pyridyl)benzothiophen-7-yl group, 6-(3-pyridyl)benzothiophen-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 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)dibenzothiophen-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)dibenzothiophen-3 -Yl group, 9-(3-pyridyl)dibenzothiophen-3-yl group.

(33): 2-(3-pyridyl)dibenzofuran-1-yl group, 3-(3-pyridyl)dibenzofuran-1-yl group, 4-(3-pyridyl)dibenzofuran-1-yl group, 6-(3 -Pyridyl)dibenzofuran-1-yl group, 7-(3-pyridyl)dibenzofuran-1-yl group, 8-(3-pyridyl)dibenzofuran-1-yl group, 9-(3-pyridyl)dibenzofuran-1-yl group Group, 1-(3-pyridyl)dibenzofuran-2-yl group, 3-(3-pyridyl)dibenzofuran-2-yl group, 4-(3-pyridyl)dibenzofuran-2-yl group, 6-(3-pyridyl ) Dibenzofuran-2-yl group, 7-(3-pyridyl)dibenzofuran-2-yl group, 8-(3-pyridyl)dibenzofuran-2-yl group, 9-(3-pyridyl)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)benzothiophen-5 -Yl group, 2-(4-pyridyl)benzothiophen-6-yl group, 3-(4-pyridyl)benzothiophen-6-yl group, 4-(4-pyridyl)benzothiophen-6-yl group, 5 -(4-pyridyl)benzothiophen-6-yl group, 7-(4-pyridyl)benzothiophen-6-yl group, 2-(4-pyridyl)benzothiophen-7-yl group, 3-(4-pyridyl) ) Benzothiophen-7-yl group, 4-(4-pyridyl)benzothiophen-7-yl group, 5-(4-pyridyl)benzothiophen-7-yl group, 6-(4-pyridyl)benzothiophen-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 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)dibenzothiophen-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)dibenzothiophen-3 -Yl group, 9-(4-pyridyl)dibenzothiophen-3-yl group.

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

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

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

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

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

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

Among these substituents, a phenyl group, p-tolyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 2-(2 -Pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3 -Pyridyl)phenyl group, 2-(4-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 2-(1-naphthyl)phenyl group, 3-(1 -Naphthyl)phenyl group, 4-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 2-(9 -Phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 4-(9 -Anthryl)phenyl group, 2-(3-fluoranthenyl)phenyl group, 3-(3-fluoranthenyl)phenyl group, 4-(3-fluoranthenyl)phenyl group, 2-(2-triphenylenyl)phenyl Group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group, 2-(3-quinolyl)phenyl group, 3-(3-quinolyl)phenyl group, 4-(3-quinolyl)phenyl group Group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group Group, 4-(8-quinolyl)phenyl group, 2-(2-dibenzothienyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 2-(4- Dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 2-(2-dibenzofuryl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 2-(4-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 2-pyridyl group, 3 -Pyridyl group, 4-pyridyl group, 1-naphthyl group, 2-naphthyl group, 3-quinolyl group, 4-quinolyl group, 8-quinolyl group, 3-isoquinolyl group, 2-ben Zothienyl group, 2-benzofuryl group, 9-anthryl group, 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, 4-dibenzofuryl group, 3-fluoranthenyl group, 1 A -pyrenyl group, a 2-triphenylenyl group or the like is preferable. Further, among these substituents, phenyl group, p-tolyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3- (2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4- (4-pyridyl)phenyl group, 2-(1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4- (2-naphthyl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 3- (3-Fluoranthenyl)phenyl group, 4-(3-fluoranthenyl)phenyl group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group, 3-(3-quinolyl)phenyl Group, 4-(3-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group Group, 4-(8-quinolyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4- Dibenzothienyl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 1-naphthyl group, 2-naphthyl group, 3-quinolyl group, 8-quinolyl group, 2-benzothienyl group, 2-benzofuryl group, 9-anthryl group , 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, and 4-dibenzofuryl group are more preferable.

The total number of ring-constituting carbon atoms of the group represented by Ar ¹³ and the total number of ring-constituting carbon atoms of the group represented by Ar ¹⁴ are each 4 to 25. Further, the total number of ring-constituting carbon atoms of the group represented by Ar ¹³ and the total number of ring-constituting carbon atoms of Ar ¹⁴ are each preferably 4 to 20.
When Ar ¹³ and Ar ¹⁴ have a substituent, the number of carbon atoms of the substituent is not included in the total number of ring-constituting carbon atoms of the groups represented by Ar ¹³ and Ar ¹⁴ . Therefore, for example, in the case of a diphenylfluorene group represented by Ar ¹³ (having 25 carbon atoms in the ring) and the group represented by Ar ¹³ has a phenyl group, the diphenylfluorene group having a phenyl group may have these (substituted The group +Ar ¹³ ) as a whole will have 31 ring-constituting carbon atoms.

The total of the total number of ring-constituting carbon atoms of Ar ¹³ and the total number of ring-constituting carbon atoms of Ar ¹⁴ is preferably 8 to 32.

[About Z ¹¹ and Z ¹² ]
One of Z ¹¹ and Z ¹² represents a nitrogen atom, and the other represents C—H.
[About L ¹¹ ]
L ¹¹ represents a phenylene group or a single bond. From the viewpoint of easy synthesis, L ¹¹ is preferably a single bond.
[About n ¹¹ ]
n ¹¹ represents 1 or 2. From the viewpoint of easy synthesis, n ¹¹ is preferably 1.

[About Ar ²¹ and Ar ²² ]
Ar ²¹ and Ar ²² each independently represent a phenyl group, a biphenyl group or a naphthyl group.
Each group represented by Ar ²¹ and Ar ²² may be independently substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group.

Specific examples of the groups represented by —Ar ²¹ and —Ar ²² include the groups (A) to (C) shown below as preferable examples.

(A): Phenyl group, p-methylphenyl group, m-methylphenyl group, o-methylphenyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, mesityl group.
(B): 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.
(C): 1-naphthyl group, 2-naphthyl 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.

Among these substituents, a phenyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, and a 2-naphthyl group in terms of excellent electron transporting material properties. Etc. are preferred.

Ar ²¹ and Ar ²² may be the same as or different from each other.
Ar ²¹ and Ar ²² are preferably the same as each other because they are easily produced.
When Ar ²¹ and Ar ²² are different, they have high solubility in an organic solvent, which is preferable.

[About Ar ²³ ]
Ar ²³ is a monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 18 carbon atoms;
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and 4 to 25 carbon atoms;
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from an atomic group consisting of H, C, O, and S;
(Iv) a group composed of any combination of two or more selected from the above (i) to (iii);
Represents.
Each of the groups (i) to (iv) represented by —Ar ²³ may be substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group.

The total number of ring-constituting carbon atoms of the group represented by Ar ²³ is 4 to 25 in all cases.
When Ar ²³ has a substituent, the number of carbon atoms of the substituent is not included in the total number of ring-constituting carbon atoms of the group represented by Ar ²³ . Therefore, for example, when the group represented by Ar ²³ is a diphenylfluorene group (having 25 carbon atoms in the ring) and the group represented by Ar ²³ has a phenyl group, the diphenylfluorene group having a phenyl group may be substituted by these (substituted The group +Ar ²³ ) as a whole will have 31 ring-constituting carbon atoms.

Examples of the aromatic hydrocarbon group (i) include phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, chrysenyl group, perylenyl group, and acenaphthyl group. Be done. In addition, as above-mentioned, these substituents (aromatic hydrocarbon group) may be substituted by the fluorine atom, the methyl group, or the phenyl group.

Examples of the (ii) heteroaromatic group include a thienyl group, a furyl group, a bithienyl group, a bifuryl group, a benzothienyl group, a benzofuryl group, a dibenzothienyl group, and a dibenzofuryl group. In addition, as above-mentioned, these substituents (aromatic hydrocarbon group) may be substituted by the fluorine atom, the methyl group, or the phenyl group.

When the cyclic azine compound (1) is used as a part of the constituent components of an organic light emitting device (OLED), high luminous efficiency and low voltage can be obtained. In particular, when the cyclic azine compound (1) is used as the electron transport layer, these effects are further exhibited.

Specific examples of the group represented by —Ar ²³ include groups (1) to (22) shown below as preferable examples.

(1): Phenyl group, p-methylphenyl group, m-methylphenyl group, o-methylphenyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, mesityl 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): 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-methylnaphthalen-7-yl group, 1-methylnaphthalene-8 -Yl group, 2-methylnaphthalen-1-yl group, 2-methylnaphthalen-3-yl group, 2-methylnaphthalen-4-yl group, 2-methylnaphthalen-5-yl group, 2-methylnaphthalene-6 -Yl group, 2-methylnaphthalen-7-yl group, 2-methylnaphthalen-8-yl group

(4): 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 Phenanthrene-9-yl group, 2-methylphenanthren-10-yl group, 3-methylphenanthren-1-yl group, 3-methylphenanthren-2-yl group, 3-methylphenanthren-4-yl group, 3-methyl Phenanthren-5-yl group, 3-methylphenanthren-6-yl group, 3-methylphenanthren-7-yl group, 3-methylphenanthren-8-yl group, 3-methylphenanthren-9-yl group, 3-methyl Phenanthrene-10-yl group, 4-methylphenanthren-1-yl group, 4-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

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

(6): 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 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-methylpyrene- 6-yl group, 9-methylpyren-7-yl group, 9-methylpyren-8-yl group, 9-methylpyren-10-yl group

(7): triphenylene-1-yl group, triphenylene-2-yl group, acenaphthylene-1-yl group, acenaphthylene-3-yl group, acenaphthylene-4-yl group, acenaphthylene-5-yl group, chrysen-1- Yl group, chrysen-2-yl group, chrysen-5-yl group, chrysen-6-yl group

(8): acenaphthylene-1-yl group, acenaphthylene-3-yl group, acenaphthylene-4-yl group, acenaphthylene-5-yl group, chrysen-1-yl group, chrysen-2-yl group, chrysen-5- Yl group, chrysene-6-yl group

(9): 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-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

(10): 3-methylbenzothiophen-2-yl group, 4-methylbenzothiophen-2-yl group, 5-methylbenzothiophen-2-yl group, 6-methylbenzothiophen-2-yl group, 7- Methylbenzothiophen-2-yl group, 2-methylbenzothiophen-3-yl group, 4-methylbenzothiophen-3-yl group, 5-methylbenzothiophen-3-yl group, 6-methylbenzothiophen-3- Yl group, 7-methylbenzothiophen-3-yl group, 2-methylbenzothiophen-4-yl group, 3-methylbenzothiophen-4-yl group, 5-methylbenzothiophen-4-yl group, 6-methyl Benzothiophen-4-yl group, 7-methylbenzothiophen-4-yl group, 2-methylbenzothiophen-5-yl group, 3-methylbenzothiophen-5-yl group, 4-methylbenzothiophen-5-yl group 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

(11): 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

(12): 2-methyldibenzothiophen-1-yl group, 3-methyldibenzothiophen-1-yl group, 4-methyldibenzothiophen-1-yl group, 6-methyldibenzothiophen-1-yl group, 7- Methyldibenzothiophen-1-yl group, 8-methyldibenzothiophen-1-yl group, 9-methyldibenzothiophen-1-yl group, 1-methyldibenzothiophen-2-yl group, 3-methyldibenzothiophen-2- Yl group, 4-methyldibenzothiophen-2-yl group, 6-methyldibenzothiophen-2-yl group, 7-methyldibenzothiophen-2-yl group, 8-methyldibenzothiophen-2-yl group, 9-methyl Dibenzothiophen-2-yl group, 1-methyldibenzothiophen-3-yl group, 2-methyldibenzothiophen-3-yl group, 4-methyldibenzothiophen-3-yl group, 6-methyldibenzothiophen-3-yl group Group, 7-methyldibenzothiophen-3-yl group, 8-methyldibenzothiophen-3-yl group, 9-methyldibenzothiophen-3-yl group

(13): 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

(14): 3-phenylthiophen-2-yl group, 4-phenylthiophen-2-yl group, 5-phenylthiophen-2-yl group, 2-phenylthiophen-3-yl group, 4-phenylthiophen-3 -Yl group, 5-phenylthiophen-3-yl group

(15): 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

(16): 3-phenylbenzothiophen-2-yl group, 4-phenylbenzothiophen-2-yl group, 5-phenylbenzothiophen-2-yl group, 6-phenylbenzothiophen-2-yl group, 7- Phenylbenzothiophen-2-yl group, 2-phenylbenzothiophen-3-yl group, 4-phenylbenzothiophen-3-yl group, 5-phenylbenzothiophen-3-yl group, 6-phenylbenzothiophen-3- Yl group, 7-phenylbenzothiophen-3-yl group, 2-phenylbenzothiophen-4-yl group, 3-phenylbenzothiophen-4-yl group, 5-phenylbenzothiophen-4-yl group, 6-phenyl Benzothiophen-4-yl group, 7-phenylbenzothiophen-4-yl group, 2-phenylbenzothiophen-5-yl group, 3-phenylbenzothiophen-5-yl group, 4-phenylbenzothiophen-5-yl group 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

(17): 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

(18): 2-phenyldibenzothiophen-1-yl group, 3-phenyldibenzothiophen-1-yl group, 4-phenyldibenzothiophen-1-yl group, 6-phenyldibenzothiophen-1-yl group, 7- Phenyldibenzothiophen-1-yl group, 8-phenyldibenzothiophen-1-yl group, 9-phenyldibenzothiophen-1-yl group, 1-phenyldibenzothiophen-2-yl group, 3-phenyldibenzothiophen-2- Group, 4-phenyldibenzothiophen-2-yl group, 6-phenyldibenzothiophen-2-yl group, 7-phenyldibenzothiophen-2-yl group, 8-phenyldibenzothiophen-2-yl group, 9-phenyl Dibenzothiophen-2-yl group, 1-phenyldibenzothiophen-3-yl group, 2-phenyldibenzothiophen-3-yl group, 4-phenyldibenzothiophen-3-yl group, 6-phenyldibenzothiophen-3-yl group Group, 7-phenyldibenzothiophen-3-yl group, 8-phenyldibenzothiophen-3-yl group, 9-phenyldibenzothiophen-3-yl group

(19): 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

(20): 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

(21): 2-(1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 4-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl) ) Phenyl group, 4-(2-naphthyl)phenyl group, 2-(9-phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(1-anthryl) ) Phenyl group, 3-(1-anthryl)phenyl group, 4-(1-anthryl)phenyl group, 2-(2-anthryl)phenyl group, 3-(2-anthryl)phenyl group, 4-(2-anthryl) ) Phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 4-(9-anthryl)phenyl group, 2-(1-pyrenyl)phenyl group, 3-(1-pyrenyl) ) Phenyl group, 4-(1-pyrenyl)phenyl group, 2-(2-pyrenyl)phenyl group, 3-(2-pyrenyl)phenyl group, 4-(2-pyrenyl)phenyl group

(22): 2-(1-dibenzothienyl)phenyl group, 3-(1-dibenzothienyl)phenyl group, 4-(1-dibenzothienyl)phenyl group, 2-(2-dibenzothienyl)phenyl group, 3- (2-Dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 2-(3-dibenzothienyl)phenyl group, 3-(3-dibenzothienyl)phenyl group, 4-(3-dibenzothienyl) Phenyl group, 2-(4-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 2-(1-dibenzofuryl)phenyl group, 3-( 1-dibenzofuryl)phenyl group, 4-(1-dibenzofuryl)phenyl group, 2-(2-dibenzofuryl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl Group, 2-(3-dibenzofuryl)phenyl group, 3-(3-dibenzofuryl)phenyl group, 4-(3-dibenzofuryl)phenyl group, 2-(4-dibenzofuryl)phenyl group, 3-(4 -Dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group

Ar ²³ represents a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group or a perylenyl group, which may be substituted with a fluorine atom, a methyl group or a phenyl group. More preferably, it is a chrysenyl group, an acenaphthyl group, a benzothienyl group, a dibenzofuryl group, or a dibenzothienyl group.

Ar ²³ is an unsubstituted phenyl group, biphenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, chrysenyl group, acenaphthyl group, in terms of easy synthesis. More preferably, it is a benzothienyl group, a dibenzofuryl group or a dibenzothienyl group.

Ar ²³ is an unsubstituted fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, chrysenyl group, acenaphthyl group, benzothienyl group, dibenzofuryl group, in terms of excellent heat resistance. Alternatively, a dibenzothienyl group is particularly preferable.

[About S ¹ ring]
X ^{21 to} X ²⁵ in the S ¹ ring each independently represent C—Ar ²³ , C—R, or a nitrogen atom.
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Only one of X ^{21 to} X ²⁵ is C-Ar ²³ .
One or two of X ^{21 to} X ²⁵ are nitrogen atoms.

[Regarding n ²¹ and L ²¹ ]
n ²¹ represents an integer of 0, 1, or 2.
L ²¹ is a phenylene group or a single bond.
Among X ²¹ to X ^25, if either one of ^{X 21} and ^{X 25} are ^{C-Ar 23} is,
L ²¹ is a single bond,
n ²¹ is 0 or 1.
When any one of X ^{22 to} X ²⁴ is C—Ar ²³ among X ^{21 to} X ²⁵ ,
L ²¹ is a phenylene group or a single bond,
n ²¹ is 0, 1, or 2.

From the viewpoint of easy synthesis, it is preferable that the S ¹ ring is a pyridylene group, a methylpyridylene group, a dimethylpyridylene group, or a pyrimidylene group.

Here, when the cyclic azine compound represented by the formula (22), which is one of the nitrogen atoms in ^X 21 ^{to X 25} in the ^{S 1} ring, cyclic azine compound (21) shown below formula (22) It is a cyclic azine compound represented by:

In the formula,
Ar ^{21 to} Ar ²³ , n ²¹ , L ²¹ and R have the same meanings as the cyclic azine compound (21);
Y ^{21 to} Y ²⁵ each independently represent C—Ar ²³ , C—R, or a nitrogen atom;
Only one of Y ^{21 to} Y ²⁵ is a nitrogen atom;
Only one of Y ^{21 to} Y ²⁵ is C-Ar ²³ ;
Of Y ²¹ to Y ^25, if either one of ^{Y 21} and ^{Y 25} are ^{C-Ar 23} is,
L ²¹ is a single bond,
n ²¹ is 0 or 1;
When any one of Y ^{22 to} Y ²⁴ is C—Ar ²³ among Y ^{21 to} Y ²⁵ ,
L ²¹ is a phenylene group or a single bond,
n ²¹ is 0, 1, or 2.

When expressed cyclic azine compounds herein are by the formula (23), a two are nitrogen atoms in ^X 21 ^{to X 25} in the ^{S 1} ring, cyclic azine compound (21) shown below formula (23) It is a cyclic azine compound represented by:

In the formula,
Ar ^{21 to} Ar ²³ , n ²¹ , L ²¹ and R have the same meanings as the cyclic azine compound (21);
Z ^{21 to} Z ²⁵ each independently represent C—Ar ²³ , C—R, or a nitrogen atom;
Two of Z ^{21 to} Z ²⁵ are nitrogen atoms;
Only one of Z ^{21 to} Z ²⁵ is C-Ar ²³ ;
When one of Z ²¹ and X ²⁵ is C—Ar ²³ among Z ^{21 to} Z ²⁵ ,
L ²¹ is a single bond,
n ²¹ is 0 or 1;
When any one of Z ^{22 to} Z ²⁴ is C—Ar ²³ among Z ^{21 to} Z ²⁵ ,
L ²¹ is a phenylene group or a single bond,
n ²¹ is 0, 1, or 2.

-Cyclic azine compound represented by formulas (24) to (27) The cyclic azine compound (21) is a cyclic azine compound represented by formula (24), (25), (26) or (27). Is more preferred:

In the formula,
Ar ^{21 to} Ar ²³ , n ²¹ , L ²¹ and R have the same meanings as the cyclic azine compound (21);
V's each independently represent C-R.
That is, the number of nitrogen atoms on the ring in the S ⁴ ring is 1.

-Cyclic azine compound represented by formulas (28) to (31) The cyclic azine compound (21) is a cyclic azine compound represented by formula (28), (29), (30) or (31). Is more preferred:

In the formula,
Ar ^{21 to} Ar ²³ , n ²¹ , L ²¹ and R have the same meanings as the cyclic azine compound (21);
W's each independently represent C—R.
That is, the number of nitrogen atoms on the ring in the S ⁵ ring is 1 or 2.

L ²¹ is preferably a single bond.

The cyclic azine compound (21) has a higher crystallization temperature than conventionally known compounds due to the contribution of the meta-substituted pyridyl group or the meta-substituted pyrimidyl group. As a result, the present inventors believe that the cyclic azine compound (21) has a high amorphous property when forming a thin film. When the cyclic azine compound (21) is used for the organic electroluminescent element, the high stability of the cyclic azine compound (21) results in improvement of driving stability of the organic electroluminescent element and improvement of luminous efficiency. The present inventors presume that the effect of is obtained.

When the cyclic azine compounds (1), (11), and (21) are used as a part of the constituent components of an organic light emitting device (OLED), high current efficiency, long life, and other effects can be obtained. can get. In particular, when the cyclic azine compounds (1), (11), and (21) are used as the electron transport layer, these effects are further exhibited.

[Specific Examples of Cyclic Azine Compounds (1), (11), and (21)]
Below, regarding the condensed ring compounds represented by the cyclic azine compounds (1), (11), and (21), preferable compounds are shown in Table 1-1 to Table 1-20, Tables 2-1 to 2-10, and Examples are shown in Tables 3-1 to 3-20 and 4-1 below, but the cyclic azine compounds (1), (11), and (21) are not limited to these compounds.

Table 2-1 to 2-10 has a backbone of listed in Table 1-1 to Table 1-20 (A1) ~ (H3) , and substituent group ^-Ar 3 the backbone has, -Ar ⁴ shows the compound of (Xm-n) which is the group shown in Tables 2-1 to 2-10.
Here, X represents an arbitrary alphabet selected from AH. m is an arbitrary integer of 1 to 48, and n is an arbitrary integer of 1 to 237. That is, the compound (Xm-n) refers to the compounds (A1-1) to (H3-237).
Therefore, for example, in the case of the compound (B1-50) in which X=B, m=1, and n=50, the compound has the skeleton (B1), the substituent —Ar ^{3 in} the skeleton is a phenyl group, and —Ar ⁴ represents the following compound in which p is a p-biphenyl group.

The compounds represented by (B1-1) to (B1-48), (B2-1) to (B2-48),... (B48-1) to (B48-48) are respectively The compound has the same structure as the corresponding skeleton (A1).
The compounds represented by (E1-1) to (E1-48), (E2-1) to (E2-48),... (E36-1) to (E36-48) correspond to each other. The same compound having the skeleton of (D1) is shown.
The compounds represented by (G2-1) to (G2-48) are the same as those having the corresponding skeleton of (G1).
The compounds represented by (H2-1) to (H2-48) are the same as those having the corresponding skeleton of (H1).

Table 4-1 has the skeletons (I1) to (I314) shown in Tables 3-1 to 3-20, and the substituent —Ar ²³ contained in the skeleton is shown in Table 4-1. The compound of formula (Ip-q), which is the indicated group, is shown.
Here, p is an arbitrary integer of 1 to 314, and q is an arbitrary integer of 1 to 12. That is, the compound (Ip-q) refers to the compounds (I1-1) to (I314-12).
Therefore, for example, in the case of the compound (I3-3) in which p=3 and q=3, the following compound having the skeleton (I4) and the substituent-Ar ^{23 in} the skeleton being a 9-phenanthryl group Is shown.

Hereinafter, applications of the cyclic azine compounds (1), (11), and (21) will be described.
<Material for organic electroluminescent device, electron transport material for organic electroluminescent device>
The cyclic azine compounds (1), (11), and (21) are not particularly limited, but can be used, for example, as a material for an organic electroluminescence device. Further, the cyclic azine compounds (1), (11), and (21) can be used, for example, as an electron transport material for an organic electroluminescence device.
That is, the material for an organic electroluminescence device according to one aspect of the present invention includes the cyclic azine compounds (1), (11), and (21). Further, the electron transport material for an organic electroluminescence device according to one aspect of the present invention includes the cyclic azine compounds (1), (11), and (21). A material for an organic electroluminescent device and an electron transport material for an organic electroluminescent device containing the cyclic azine compounds (1), (11), and (21) contribute to the production of an organic electroluminescent device excellent in durability and current efficiency. It is a thing.

<Organic electroluminescent device>
An organic electroluminescent device according to one aspect of the present invention includes cyclic azine compounds (1), (11), and (21).
The structure of the organic electroluminescent element is not particularly limited, but examples thereof include the following structures (i) to (vi).
(I): Anode/light emitting layer/cathode (ii): Anode/hole transporting layer/light emitting layer/cathode (iii): Anode/light emitting layer/electron transporting layer/cathode (iv): Anode/hole transporting layer/ Light emitting layer/electron transport layer/cathode (v): anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode (vi): anode/hole injection layer/charge generation layer /Hole transport layer/Light emitting layer/Electron transport layer/Cathode

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

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

[Layer containing cyclic azine compound represented by formula (11) and formula (1)]
The organic electroluminescent device contains a cyclic azine compound represented by the above formulas (11) and (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 a cathode. .. Therefore, in the configuration example shown in FIG. 1, in the organic electroluminescent device 100, at least one layer selected from the group consisting of the light emitting layer 6 and the electron transport layer 7 has the cyclic azine compound (1), (11), and (21). including. In particular, the electron transport layer 7 preferably contains the cyclic azine compounds (1), (11), and (21). The cyclic azine compounds (1), (11), and (21) may be contained in a plurality of layers included in the organic electroluminescent device, and an electron injection layer is provided between the electron transport layer and the cathode. If so, the electron injection layer may include the cyclic azine compounds (1), (11), and (21).
In addition, below, the organic electroluminescent element 100 in which the electron carrying layer 7 contains cyclic azine compound (1), (11), and (21) is demonstrated.

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

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

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

The transparent material used for the anode is not particularly limited, and examples thereof include indium-tin oxide (ITO), indium-zinc oxide (IZO), tin oxide, and aluminum. -Doped tin oxide, magnesium-indium oxide, nickel-tungsten oxide, other metal oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, and metal sulfides such as zinc sulfide. Is mentioned.
In the case of an organic electroluminescent device having a structure in which light is extracted only from the cathode side, the transmission characteristics of the anode are not important. Therefore, examples of the material used for the anode in this case include gold, iridium, molybdenum, palladium, platinum and the like.
A buffer layer (electrode interface layer) may be provided on the anode.

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

Further, the hole injection layer and the hole transport layer also function as a layer having an electron barrier property. That is, the electrons injected from the cathode and transported from the electron injection layer and/or the electron transport layer to the light emitting layer are blocked by the electron barrier existing at the interface between the light emitting layer and the hole injection layer and/or the hole transport layer. The leakage into the hole injection layer and/or the hole transport layer is suppressed. As a result, the electrons are accumulated at the interface in the light emitting layer, resulting in effects such as improvement in current efficiency, and an organic electroluminescent device having excellent light emitting performance can be obtained.

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

Specific examples of the material for the hole injection layer and the hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcones. Derivative, oxazole derivative, styrylanthracene derivative, fluorenone derivative, hydrazone derivative, stilbene derivative, silazane derivative, aniline copolymer, conductive polymer oligomer (particularly thiophene oligomer), porphyrin compound, aromatic tertiary amine compound, styryl Examples thereof include amine compounds. Among these, porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds are preferable, and aromatic tertiary amine compounds are particularly preferable.

Specific examples of the aromatic tertiary amine compound and the styrylamine compound include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl and N,N'-diphenyl-N,N'-. Bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis (4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolyl) Aminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'. -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 can be mentioned.
Inorganic compounds such as p-type-Si and p-type-SiC can also be given as examples of the material of the hole injection layer and the material of the hole transport layer.

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

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

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

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

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

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

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

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

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

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

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

As described above, the electron transport layer preferably contains the cyclic azine compound represented by the formula (11) and the formula (1).

In addition to the cyclic azine compounds (1), (11), and (21), the electron transport layer may further include a conventionally known electron transport material. Known electron transport materials include, for example, lithium 8-hydroxyquinolinato (Liq), bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinate). Nato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolate)gallium, bis(2 -Methyl-8-quinolinato)-1-naphtholate aluminum, or bis(2-methyl-8-quinolinato)-2-naphtholate gallium, 2-[3-(9-phenanthrenyl)-5-(3-pyridinyl) Phenyl]-4,6-diphenyl-1,3,5-triazine, and 2-(4"-di-2-pyridinyl[1,1':3',1"-terphenyl]-5- Yl)-4,6-diphenyl-1,3,5-triazine, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-). Phenanthroline), BAlq (bis(2-methyl-8-quinolinolato)-4-(phenylphenolato)aluminum), and bis(10-hydroxybenzo[h]quinolinato)beryllium).

The electron transport layer may have a single-layer structure composed of one or more materials, or a laminated structure composed of a plurality of layers having the same composition or different compositions.
When the electron transport layer has a two-layer structure in which the light emitting layer side is the first electron transport layer and the cathode side is the second electron transport layer, the second electron transport layer is the cyclic azine compound (1), (11), and It is preferable to include (21).

[Cathode 8]
A cathode 8 is provided on the electron transport layer 7.
In the case of an organic electroluminescence device having a structure in which only the light emission that has passed through the anode is taken out, the cathode can be formed of any conductive material.
Examples of materials for the cathode include sodium, sodium-potassium alloy, magnesium, lithium, magnesium/copper mixture, magnesium/silver mixture, magnesium/aluminum mixture, magnesium/indium mixture, aluminum/aluminum oxide (Al ₂ O ₃ ) mixture, indium. , Lithium/aluminum mixtures, rare earth metals and the like.
A buffer layer (electrode interface layer) may be provided on the cathode (electron transport layer side).

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

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

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

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

The cyclic azine compounds (1), (11), and (21) according to one embodiment of the present invention can be synthesized by appropriately combining known reactions (for example, Suzuki-Miyaura cross coupling reaction). is there.

Hereinafter, the present invention will be described in more detail based on Examples, but the present invention should not be construed as being limited to these Examples.

¹ H-NMR measurement was performed using Gemini200 (manufactured by Varian).
The FDMS measurement was performed using M-80B manufactured by Hitachi Ltd.
The glass transition temperature was measured using DSC7020 (manufactured by Hitachi High-Tech Science Co., Ltd.).
The emission characteristics of the organic electroluminescent device were evaluated by applying a direct current to the prepared device at room temperature and using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse).

Synthesis Example-1

2-{4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]}-4,6-diphenyl-1,3,5-under an argon stream. Triazine (5.00 g, 11.49 mmol), 2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine (5.84 g, 12.63 mmol). , And tetrakis(triphenylphosphine)palladium (0.40 g, 0.345 mmol) were dissolved in tetrahydrofuran (100 mL). To this, a 2 M aqueous potassium carbonate solution (18 mL, 36 mmol) was added, and the mixture was stirred at 75° C. for 26 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL), ethanol (50 mL), hexane (50 mL). This solid was suspended in toluene (250 mL), stirred at 125° C., and then left to cool. The precipitated solid was filtered off and the obtained solid was dissolved in 500 mL of toluene. Activated carbon was added to the solution and the mixture was stirred, filtered through Celite, and the filtrate was concentrated under reduced pressure. The concentrate is dried to dryness to give the desired 2-(3′-{6-[(1,1′-biphenyl)-4-yl]-4-phenylpyridin-2-yl}-1,1′. A white solid (yield 6.46 g, 81%) of -biphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (Compound B1-50) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39 (t, J=7.2 Hz, 1 H), 7.47-7.53 (m, 3 H), 7.55-7.72 (m , 11H), 7.77-7.82 (m, 5H), 7.94 (d, J=8.5Hz, 2H), 8.00 (s, 2H), 8.26 (d, J=7). .6 Hz, 1 H), 8.33 (d, J=8.7 Hz, 2 H), 8.57 (s, 1 H), 8.81-8.84 (m, 4 H), 8.91 (d, J). = 8.6 Hz, 2H).
The glass transition temperature of the compound B1-50 was 116°C.

Synthesis Example-2

2-[(1,1′-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was converted into 2-(3-bromophenyl)-6-(4-chlorophenyl)-4. The same experimental procedure as in Synthesis Example-1 was carried out except that -phenylpyridine was used to obtain the target 2-{3'-[6-(4-chlorophenyl)-4-phenylpyridyl-2-yl]-1. , 1'-biphenyl-4-yl}-4,6-diphenyl-1,3,5-triazine was obtained as a white solid (yield 6.00 g, yield 92%).

Under a nitrogen stream, 4,6-diphenyl-2-{3'-[6-(4-chlorophenyl)-4-phenylpyridyl-2-yl]-biphenyl-4-yl}-1,3,5-triazine( 6.00g, 9.25 mmol), 3- pyridylboronic acid (1.3726g, 11.10 mmol), 0.05M of _Pd (OAc) 2 / Xphos THF solution _4.7ml, K 2 CO ₃ aqueous solution 17 mL, THF (100 mL) was added, and the mixture was stirred at 70°C for 1 day. After the reaction, the mixture was allowed to cool to room temperature, and the precipitated solid was collected by filtration. The obtained solid is recrystallized (toluene/hexane) and recrystallized (chlorobenzene/hexane) to give the desired 2-(3′-{4-phenyl-6-[4-(3-pyridyl)phenyl]pyridyl. 2-yl}-1,1'-biphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (Compound B1-75) as a white solid (yield 2.67 g, 42%). ) Got.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.41 (dd, 1H), 7.69-7.51 (m, 10H), 7.82-7.77 (m, 5H), 7. 94 (dd, 2H), 7.98 (dt, 1H), 8.00 (dd, 2H), 8.25 (d, 1H), 8.37 (d, 2H), 8.56 (t, 1H ), 8.63 (dd, 1H), 8.81 (dd, 4H), 8.91 (d, 2H), 8.96 (d, 1H).
The glass transition temperature of the compound B1-75 was 120°C.

Synthesis Example-3

2-[(1,1′-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was converted into 4-(3-bromophenyl)-2-(1-naphthyl)-6. The same experimental procedure as in Synthesis Example-1 was carried out except that -phenylpyridine was used to obtain the desired 2-{3'-[2-(1-naphthyl)-6-phenylpyridyl-4-yl]-1. , 1'-biphenyl-4-yl}-4,6-diphenyl-1,3,5-triazine (C1-57) was obtained as a white solid (yield 4.4 g, 53%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.47-7.62 (m, 5H), 7.66-7.76 (m, 8H), 7.88 (d, J=7.2Hz). , 1H), 7.97 (d, J=8.0 Hz, 1H), 8.05-8.13 (m, 4H), 8.16 (d, J=8.6 Hz, 2H), 8.28. −8.34 (m, 3H), 8.43 (s, 1H), 8.47 (s, 1H), 8.77 (d, J=6.9 Hz, 4H), 8.86 (d, J) = 8.6 Hz, 2H).
The glass transition temperature of the compound C1-57 was 114°C.

Synthesis Example-4

2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was converted into 2-(3-bromophenyl)-4-(1-naphthyl)-6. The same experimental procedure as in Synthesis Example-1 was performed except that -phenylpyridine was used to obtain the desired 2-{3'-[4-(1-naphthyl)-6-phenylpyridyl-2-yl]-1. , 1'-biphenyl-4-yl}-4,6-diphenyl-1,3,5-triazine (A1-57) was obtained as a white solid (5.2 g, 73% yield).

< ¹ >H-NMR(CDCl3)(delta)(ppm):7.74-7.72(m,14H),7.73(d,J=8.1Hz,1H),7.83-7.87(m,). 4H), 7.91(d, J=7.8Hz, 3H), 8.16-8.20(m, 3H), 8.50(s, 1H), 8.74(d, J=6. 4Hz, 4H), 8.82 (d, J=8.5Hz, 2H).
The glass transition temperature of the compound A1-57 was 116°C.

Synthesis Example-5

2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was converted into 2-[(1,1'-biphenyl)-4-yl]-4. The same experimental procedure as in Synthesis Example-1 was carried out except that it was changed to -(3-bromophenyl)-2-phenylpyridine to give the desired 2-(3'-{6-phenyl-2-[(1, 1'-biphenyl)-4-yl]pyridin-2-yl}-1,1'-biphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (C1-50) white solid (Yield 3.0 g, yield 69%) was obtained.

¹ H-NMR (CDCL3) δ (ppm): 7.39 (t, J=7.3 Hz, 1 H), 7.46-7.71 (m, 14 H), 7.76-7.85 (m, 4H), 7.91(d, J=8.4Hz, 2H), 8.01(d, J=12.5Hz, 2H), 8.07(s, 1H), 8.26(d, J= 7.2 Hz, 2 H), 8.33 (d, J=8.4 Hz, 2 H), 8.82 (d, J=6.5 Hz, 4 H), 8.91 (d, J=8.3 Hz, 2 H) ).

Synthesis Example-6

2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was converted into 2-[(1,1'-biphenyl)-4-yl]-4. Changed to -(4-bromophenyl)-6-phenyl-1,3,5-triazine to give 2-{4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2 -Yl)phenyl]}-4,6-diphenyl-1,3,5-triazine was replaced with 3-(2,6-diphenyl-4-pyridyl)phenylboronic acid in the same manner as in Synthesis Example-1. The desired 2-(3′-(2,6-diphenylpyridin-4-yl)-1,1′-biphenyl-4-yl)-4-(1,1′-biphenyl) A white solid (yield 22.2 g, yield 74%) of -6-phenyl-1,3,5-triazine (C2-1) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.41-7.56 (m, 9H), 7.59-7.74 (m, 6H), 7.79-7.84 (m, 4H). ), 7.90 (d, J=8.3 Hz, 2H), 7.98 (s, 2H), 8.06 (s, 1H), 8.25 (d, J=7.5 Hz, 4H), 8.23 (d, J=6.5 Hz, 2H), 8.87-8.93 (m, 4H).
The glass transition temperature of the compound C2-1 was 121°C.

Synthesis Example-7

2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was converted into 2-[(1,1'-biphenyl)-4-yl]-4. Changed to -(4-bromophenyl)-6-phenyl-1,3,5-triazine to give 2-{4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2 -Yl)phenyl]}-4,6-diphenyl-1,3,5-triazine was replaced with 3-(4,6-diphenyl-2-pyridyl)phenylboronic acid in the same manner as in Synthesis Example-1. The desired 2-(3′-(4,6-diphenylpyridin-2-yl}-1,1′-biphenyl-4-yl)-4-(1,1′-biphenyl) A white solid of -6-phenyl-1,3,5-triazine (A2-1) (amount 5.39 g, yield 55%) was obtained.

¹ H-NMR (CDCl 3) δ (ppm): 7.43-7.71 (m, 13 H), 7.76 (d, J=7.2 Hz, 2 H), 7.80-7.87 (m, 5H), 7.95-8.01 (m, 4H), 8.27 (d, J = 8.1Hz, 3H), 8.57 (s, 1H), 8.86 (d, J = 8. 1 Hz, 2H), 8.91 (d, J=8.6 Hz, 2H), 8.94 (d, J=8.6 Hz, 2H).

Synthesis Example-8

2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was converted into 4-(4-bromophenyl)-2,6-diphenyl-1,3. , 5-triazine, 2-{4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]}-4,6-diphenyl-1, 3,5-triazine was added to 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3′-(2,6-diphenylpyridin-4-yl)- The same experimental procedure as in Synthesis Example 1 was performed except that 1,1′-biphenyl was used to obtain the desired 2-[(3″-(2,6-diphenylpyridin-4-yl)-1, 1′:3′:1″-terphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (F13-1) white solid (13.5 g, 76% yield) Got

¹ H-NMR (CDCl 3) δ (ppm): 7.43-7.81 (m, 18H), 7.89 (d, 8.4 Hz, 2H), 7.97 (s, 2H), 8.00. (D, 13.2Hz, 2H), 8.23 (d, 7.1Hz, 4H), 8.81 (d, 6.5Hz, 4H), 8.89 (d, 8.6Hz, 2H).

Synthesis Example-9

2-[(1,1′-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was converted into 2-(3″′-chloro-1,1′:4′, 1″:3″,1′″-quaterphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine, 2-{4-[(4,4, 5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]}-4,6-diphenyl-1,3,5-triazine was added to 3-(2,6-diphenyl-4-pyridyl ) By the same experimental procedure as in Synthesis Example-1 except that phenylboronic acid was used, the desired 2-[(3'''-(2,6-diphenylpyridin-4-yl)-1,1 was obtained. White solid of':4',1'':3'',1'''-quaterphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (G3-1) (yield (4.2 g, 79% yield) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.44-7.73 (m, 16H), 7.76-7.89 (m, 8H), 7.95 (s, 1H), 7. 97(s, 2H), 8.01(s, 1H), 8.23(d, J=7.1Hz, 4H), 8.81(d, J=6.4Hz, 4H), 8.88( d, J=8.6 Hz, 2H).

Synthesis example-1

2-[3′-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl-4-yl}]-4 under a stream of argon , 6-diphenyl-1,3,5-triazine (2.05 g, 4.0 mmol), 2-bromo-6-chloropyridine (2.31 g, 12.0 mmol), and tetrakis(triphenylphosphine)palladium (0. 0.139 g, 0.12 mmol) was dissolved in tetrahydrofuran (20 mL). To this, a 2 M aqueous potassium carbonate solution (6 mL, 12 mmol) was added, and the mixture was stirred at 75° C. for 4 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL), methanol (50 mL), hexane (50 mL). This solid was suspended in toluene (50 mL), stirred at 120° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (5 mL) and methanol (50 mL) to obtain the desired 4,6-diphenyl-2-[3'-(2-chloropyridin-6-yl)-1, A white solid of 1'-biphenyl-4-yl]-1,3,5-triazine (amount 1.35 g, yield 68%) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.88 (d, J=8.0 Hz, 2H), 8.81 (dd, J ₁ =8.0 Hz, J ₂ =1.6 Hz, 4H) , 8.34 (t, J=1.6 Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.88 (d, J=8.0 Hz, 2H), 7.77− 7.75 (m, 2H), 7.64-7.58 (m, 9H)

Synthesis Example-10

4,6-diphenyl-2-[3'-(2-chloropyridin-6-yl)-1,1'-biphenyl-4-yl]-1,3 obtained in Synthesis Example-1 under an argon stream. 5-triazine (1.35 g, 2.7 mmol), 9-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenanthrene (2.37 g, 8.2 mmol), palladium acetate (6. 11 mg, 0.03 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (38.9 mg, 0.08 mmol; X-Phos) were dissolved in tetrahydrofuran (14 mL). To this, a 2 M aqueous solution of tripotassium phosphate (4 mL, 8.1 mmol) was added, and the mixture was stirred at 75° C. for 3 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL), methanol (50 mL), hexane (50 mL). This solid was suspended in toluene (80 mL), stirred at 120° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (5 mL) and methanol (50 mL) to give the desired 4,6-diphenyl-2-[3'-{2-(9-phenanthryl)pyridin-6-yl. }-1,1'-Biphenyl-4-yl]-1,3,5-triazine (Compound I171-3) was obtained as a white solid (amount 1.58 g, yield 91%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.86 (d, J=8.7 Hz, 2 H), 8.83-8.79 (m, 5 H), 8.77 (d, J=8). .7 Hz, 1 H), 8.47 (s, 1 H), 8.28 (d, J=8.4 Hz, 1 H), 8.18 (d, J=7.8 Hz, 1 H), 8.00-7 .91 (m, 4H), 7.89 (d, J=8.1 Hz, 2H), 7.77 (d, J=7.7 Hz, 1H), 7.74-7.57 (m, 12H)
The glass transition temperature of compound I171-3 was 118 degreeC.

Synthesis example-2

2-[3′-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl-4-yl}]-4 under a stream of argon , 6-diphenyl-1,3,5-triazine (12.79 g, 25.0 mmol), 4-bromo-2-chloropyridine (14.43 g, 75.0 mmol), and tetrakis(triphenylphosphine)palladium(0. 0.867 g, 0.75 mmol) was dissolved in tetrahydrofuran (125 mL). To this, a 2M aqueous potassium carbonate solution (37.5 mL, 75 mmol) was added, and the mixture was stirred at 75° C. for 13 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (200 mL), methanol (100 mL), and hexane (100 mL). This solid was suspended in toluene (550 mL), stirred at 120° C., and allowed to cool. The precipitated solid was filtered off and washed with toluene (20 mL) and methanol (100 mL) to obtain the target 4,6-diphenyl-2-[3′-(2-chloropyridin-4-yl)-1, A white solid of 1'-biphenyl-4-yl]-1,3,5-triazine was obtained (11.6 g, 93% yield).

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.89 (dd, J ₁ =6.4 Hz, J ₂ =1.6 Hz, 2H), 8.83-8.80 (m, 4H), 8 .49 (d, J=2.4 Hz, 1H), 7.53 (t, J=1.6 Hz, 1H), 7.84 (dd, J ₁ =6.4 Hz, J ₂ =1.6 Hz, 2H ), 7.80 (dt, J ₁ =6.4 Hz, J ₂ =1.6 Hz, 1H), 7.65-7.59 (m, 9H), 7.53 (dd, J ₁ =4.8 Hz). , J ₂ =1.6Hz, 1H)

Synthesis Example-11

4,6-diphenyl-2-[3′-(2-chloropyridin-4-yl)-1,1′-biphenyl-4-yl]-1,3, obtained in Synthesis Example-2, under an argon stream. 5-triazine (6.21 g, 12.5 mmol), 9-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenanthrene (10.9 g, 37.5 mmol), palladium acetate (28. 06 mg, 0.13 mmol) and X-Phos (178.77 mg, 0.38 mmol) were dissolved in tetrahydrofuran (160 mL). To this, a 2M aqueous solution of tripotassium phosphate (19 mL, 37.5 mmol) was added, and the mixture was stirred at 75°C for 3 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (200 mL), methanol (200 mL), and hexane (200 mL). This solid was suspended in toluene (1000 mL), stirred at 120° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (30 mL) and methanol (200 mL) to obtain the target 4,6-diphenyl-2-[3'-{2-(9-phenanthryl)pyridin-4-yl. } White solid (yield 6.92 g, 86.7%) of 1,1'-biphenyl-4-yl]-1,3,5-triazine (Compound I179-3) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.93 (d, J=6.4 Hz, 1 H), 8.88 (dd, J ₁ =6.4 Hz, J ₂ =1.6 Hz, 2H) , 8.81-8.79(m, 6H), 8.76(d, J=8.0Hz, 1H), 8.18(d, J=6.4Hz, 1H), 8.04(t, J=1.6 Hz, 1H), 7.98-7.96 (m, 4H), 7.87 (d, J=8.0 Hz, 2H), 7.82-7.77 (m, 2H), 7.66-7.59 (m, 10H)
Compound I179-3 had a glass transition temperature of 120°C, a crystallization temperature of 182°C, and a melting point of 246°C.

Synthesis example-3

Under a stream of argon, 2-bromo-4-chloropyridine (0.679 g, 3.53 mmol), 5,5-dimethyl-2-(9-phenanthrenyl)-1,3,2-dioxaborilane (1.02 g, 3. 53 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.122 g, 0.106 mmol) were dissolved in tetrahydrofuran (30 mL). A 2.0 M potassium carbonate aqueous solution (5.3 mL, 10.6 mmol) was added thereto, and the mixture was stirred at 65° C. for 24 hours. After allowing to cool to room temperature, the mixture was separated with water and methylene chloride. The obtained organic layer was concentrated to dryness to obtain a target yellowish white solid of 4-chloro-2-(9-phenanthrenyl)pyridine (yield 0.978 g, yield 96%).

Synthesis Example-12

2-[3′-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl-4-yl}]-4 under a stream of argon ,6-Diphenyl-1,3,5-triazine (1.25 g, 2.98 mmol), 3-chloro-5-(9-phenanthrenyl)pyridine (0.949 g, 3.28 mmol) obtained in Synthesis Example-3. , Palladium acetate (20.0 mg, 89.1 μmol), and X-Phos (85.1 mg, 0.179 mmol) were dissolved in tetrahydrofuran (30 mL). A 2.0 M tripotassium phosphate aqueous solution (4.5 mL, 8.93 mmol) was added thereto, and the mixture was stirred at 50° C. for 3 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water and methanol. This solid was suspended in toluene (250 mL), stirred at 125° C., and then left to cool. By recrystallizing the obtained solid by toluene, the target 4,6-diphenyl-2-[3'-{5-(9-phenanthrenyl)pyridin-3-yl}-1,1'-biphenyl-4 was obtained. -Yl]-1,3,5-triazine (Compound I187-3) was obtained as a white solid (amount 1.37 g, yield 72%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 9.06 (d, J=2.3 Hz, 1 H), 8.88 (d, J=8.7 Hz, 2 H), 8.85 (d, J =1.8 Hz, 1H), 8.81-8.76 (m, 5H), 8.18 (d, J=2.3 Hz, 1H), 7.99 (s, 1H), 7.94( dd, J=12.1, 7.5 Hz, 2H), 7.87 (d, J=8.7 Hz, 2H), 7.80-7.71 (m, 5H), 7.69-7. 58 (m, 10H).
The glass transition temperature of compound I187-3 was 124 degreeC.

Synthesis Example-13

Under an argon stream, 2-{3-(trifluoromethanesulfonyloxy)phenyl}-4,6-bis([1,1′-biphenyl]-4-yl)triazine (4.00 g, 6.56 mmol), 3 -(Phenanthrene-9-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (3.25 g, 8.53 mmol), palladium acetate (0 0.04 g, 0.16 mmol) and X-Phos (0.16 g, 0.33 mmol) were dissolved in tetrahydrofuran (50 mL). To this, a 4M aqueous solution of tripotassium phosphate (2.5 mL, 9.97 mmol) was added, and the mixture was stirred at 65° C. for 4 hours. Water (50 ml) was added, the mixture was allowed to cool to room temperature, and the precipitated solid was filtered off. The obtained solid was washed with water (50 mL) and ethanol (50 mL). This solid was suspended in ethyl acetate (50 mL), stirred at 75° C., and allowed to cool. The precipitated solid was filtered off, the obtained solid was dissolved in 300 mL of chlorobenzene, the insoluble matter was filtered off, and the filtrate was evaporated under reduced pressure. Ethanol (50 ml) was added, and the precipitated solid was filtered off by stirring, and the obtained solid was washed with hexane. It was again dissolved in chlorobenzene (300 ml), activated carbon was added to the solution and the mixture was stirred, then filtered through a Kiriyama funnel lined with silica gel and celite, and the filtrate was evaporated under reduced pressure. The concentrate was dried to dryness to give the desired 4,6-bis[(1,1′-biphenyl)-4-yl]-2-{[5-(phenanthren-9-yl)pyridin-3-yl. ]-Phenyl-3-yl}-1,3,5-triazine (Compound I27-3) was obtained as a white solid (yield 1.7 g, yield 36%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 9.17-9.10 (m, 2H), 8.92-8.82 (m, 7H), 8.78 (d, J=8.6Hz). , 1H), 8.26 (m, 1H), 8.03-7.92 (m, 3H), 7.85-7.79 (m, 5H), 7.79-7.61 (m, 9H). ), 7.51 (t, J=7.2 Hz, 4H), 7.42 (t, J=7.6 Hz, 2H).
Compound I27-3 had a glass transition temperature of 136°C, a crystallization temperature of 201°C, and a melting point of 255°C.

Synthesis example-4

Under an argon stream, 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine( 7.50 g, 17.2 mmol), 2-chloro-4-iodo-3-methylpyridine (4.80 g, 19.0 mmol), and tetrakis(triphenylphosphine)palladium (0.597 g, 0.52 mmol) in tetrahydrofuran. It was dissolved in (250 mL). A 2 M potassium carbonate aqueous solution (25.8 mL, 52 mmol) was added thereto, and the mixture was stirred at 70° C. for 10 hours. After allowing to cool to room temperature, the mixture was separated with water and methylene chloride. The obtained organic layer was concentrated to dryness to give a yellow solid. This solid was suspended in toluene (10 mL), stirred at 120° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (5 mL) and ethanol (10 mL) to give the desired 2-[3-(2-chloro-3-methylpyridin-4-yl)phenyl]-4,6. A yellow solid of diphenyl-1,3,5-triazine (amount 2.8 g, yield 37%) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.87-8.70 (m, 6H), 8.34 (d, J=4.8 Hz, 1H), 7.72-7.53 (m , 9H), 2.41 (s, 3H)

Synthesis Example-14

2-[3-(2-chloro-3-methylpyridin-4-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (2.75 g) obtained in Synthesis Example-4 under an argon stream. , 6.32 mmol), 9-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenanthrene (2.20 g, 7.59 mmol), tetrakis(triphenylphosphine)palladium (219.2 mg, 0.19 mmol) was dissolved in tetrahydrofuran (65 mL). To this, a 2 M aqueous potassium carbonate solution (9.5 mL, 21.6 mmol) was added, and the mixture was stirred at 70° C. for 13 hours. After allowing to cool to room temperature, water (300 mL) was added, and the precipitated solid was filtered off. The obtained solid was washed with water (100 mL) and ethanol (200 mL). This solid was suspended in toluene (100 mL), stirred at 120° C., and allowed to cool. The precipitated solid was separated by filtration, and washed with toluene (10 mL) and ethanol (50 mL) to obtain the target 2,4-diphenyl-6-[3-(3-methyl-2-phenanthrenylpyridine-4. A white solid (yield 2.56 g, yield 70.2%) of -yl)phenyl]-1,3,5-triazine (Compound I141-3) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.87-8.77 (m, 8H), 8.75 (d, J=4.4 Hz, 1H), 7.95 (d, J=8). 9.9 Hz, 1 H), 7.85 (s, 1 H), 7.56-7.73 (m, 13 H), 7.44 (d, J=5.6 Hz, 1 H), 2.12 (s, 3 H). )
Compound I141-3 had a glass transition temperature of 134°C, a crystallization temperature of 215°C, and a melting point of 268°C.

Synthesis Example-5

Under a stream of argon, 3-bromo-6-hydroxy-2-methylpyridine (5.23 g, 27.8 mmol), 5,5-dimethyl-2-phenanthrenyl-1,3,2-dioxaborinane (9.69 g, 33. 4 mmol), palladium acetate (187 mg, 0.83 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (385 mg, 1.67 mmol; S-Phos) were suspended in tetrahydrofuran (93 mL) and 3M- Aqueous potassium phosphate solution (28 mL) was added. The mixture was stirred at 80° C. for 21 hours, allowed to cool to room temperature, and chloroform and water were added to the reaction mixture. After separating the organic layer, the aqueous layer was extracted twice with chloroform. The organic layers were combined and dried over sodium sulfate, the solid was filtered off, and the low boiling fraction was distilled off under reduced pressure. The obtained crude product was purified by silica gel chromatography (eluent: hexane/ethyl acetate) to obtain 6-hydroxy-2-methyl-3-phenanthrenylpyridine (yield 3.58 g, yield 45). %).

¹ H-NMR (CDCl ₃ ) δ (ppm): 12.63 (s, 1 H), 8.80 (d, J=8.2 Hz, 1 H), 8.74 (d, J=8.2 Hz, 1 H). ), 7.91 (dd, J=7.8 Hz, 1.3 Hz, 1 H), 7.74-7.63 (m, 5 H), 7.59 (ddd, J=8.2 Hz, 6.9 Hz, 1.2Hz, 1H), 7.46(d, J=9.2Hz, 1H), 6.59(d, J=9.2Hz, 1H), 2.21(s, 3H)

Synthesis Example-6

Under an argon stream, 6-hydroxy-2-methyl-3-phenanthrenylpyridine (1.91 g, 6.7 mmol) obtained in Synthesis Example-5 was dissolved in dichloromethane (54 mL), and pyridine (0.81 mL, 10.1 mmol) was added. After cooling the mixture to 0° C., trifluoromethanesulfonic anhydride (1.65 mL, 10.1 mmol; Tf ₂ O) was added. The mixture was warmed to room temperature and stirred for 16 hours, then chloroform and water were added to the reaction mixture. After separating the organic layer, the aqueous layer was extracted twice with chloroform. The organic layers were combined and dried over sodium sulfate, the solid was filtered off, and the low boiling fraction was distilled off under reduced pressure. The obtained crude product was purified by silica gel chromatography to obtain {3-(9-phenanthrenyl)-2-methylpyridin-6-yl}triflomethanesulfonate (2.77 g, 99%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.81 (d, J=8.3 Hz, 1 H), 8.76 (d, J=8.2 Hz, 1 H), 7.91 (dd, J). =7.8 Hz, 1.2 Hz, 1H), 7.81 (d, J=8.1 Hz, 1H), 7.76-7.69 (m, 2H), 7.67 (ddd, J=7. 4 Hz, 7.4 Hz, 1.2 Hz, 1 H), 7.62 (s, 1 H), 7.56 (ddd, J=8.2 Hz, 7.0 Hz, 1.2 Hz, 1 H), 7.38 (d , J=8.2 Hz, 1H), 7.16 (d, J=8.2 Hz, 1H), 2.30 (s, 3H)

Synthesis Example-15

Under an argon stream, {3-(9-phenanthrenyl)-2-methylpyridin-6-yl}trifuromethanesulfonate obtained in Synthesis Example-6, 2-[3-(4,4,5,5-tetramethyl- 1,3,2-Dioxaborolan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (2.77 g, 6.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (193 mg). , 0.18 mmol) was suspended in tetrahydrofuran (28 mL). A 2.0 M potassium carbonate aqueous solution (25 mL) was added thereto, and the mixture was stirred at 80° C. for about 14 hours. After cooling to room temperature, the solvent was removed under reduced pressure, and water and methanol were added. The precipitated solid was filtered off and washed with water (50 mL) and methanol (50 mL). The obtained solid was dissolved in toluene (200 mL). Activated carbon was added to this solution, and the mixture was stirred, filtered through Celite, and the filtrate was concentrated under reduced pressure. By recrystallizing the obtained crude product from toluene, 2,4-diphenyl-6-[3-(2-methyl-3-phenanthrenylpyridin-6-yl)phenyl]-1 of the desired product was obtained. , 3,5-triazine (Compound I153-3) was obtained (1.87 g, 58%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 9.45 (t, J=1.6 Hz, 1 H), 8.88 (ddd, J=7.8, Hz, 1.4 Hz, 1.4 Hz, 1H), 8.86-8.81 (m, 5H), 8.79 (d, J=8.0Hz, 1H), 8.44 (ddd, J=7.8Hz, 1.8Hz, 1.2Hz) , 1H), 7.94 (dd, J=7.8Hz, 1.3Hz, 1H), 7.93 (d, J=7.8Hz, 1H), 7.80 (d, J=7.8Hz, 1H), 7.78-7.55 (m, 13H), 2.46 (s, 3H)
The glass transition temperature of compound I153-3 was 122 degreeC.

Synthesis Example-16

Under an argon stream, 2-{3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-3-yl}-4, 6-bis[(1,1′-biphenyl)-4-yl]-1,3,5-triazine (4.20 g, 6.33 mmol), 5-chloro-2-(naphthylene-1-yl)pyridine( 1.82 g, 7.60 mmol), palladium acetate (0.03 g, 0.13 mmol) and X-Phos (0.12 g, 0.25 mmol) were dissolved in tetrahydrofuran (70 mL). To this, a 2 M aqueous solution of tripotassium phosphate (9.5 mL, 18.9 mmol) was added, and the mixture was stirred at 65° C. for 24 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL) and ethanol (50 mL). This solid was suspended in ethyl acetate (50 mL), stirred at 75° C., and allowed to cool. The deposited solid was separated by filtration, suspended in toluene (1000 mL), stirred at 110° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (5 mL) and ethanol (10 mL) to give the desired 4,6-bis[(1,1′-biphenyl)-4-yl]-2-{3′. A white solid of -[2-(naphthylene-1-yl)pyridin-4-yl][1,1'-biphenyl]-3-yl}-1,3,5-triazine (Compound I273-2) (yield 2 0.8 g, yield 59%) was obtained.

_{^{1 H-NMR (CDCl 3)}} δ (ppm): 9.12-9.11 (m, 1H), 9.11 (t, J = 1.7Hz, 1H), 8.93-8.87 (m , 5H), 8.25-8.22 (m, 1H), 8.18 (dd, J=8.1, 2.3Hz, 1H), 8.06 (t, J=2.0Hz, 1H). , 7.98-7.95 (m, 3H), 7.89-7.85 (m, 5H), 7.80-7.71 (m, 9H), 7.62 (dd, J=8. 3, 7.0 Hz, 1H), 7.54 (d, J=2.6 Hz, 2H), 7.53-7.51 (m, 4H), 7.47-7.42 (m, 2H).

Synthesis Example-17

2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane under an argon stream. 2-yl)[1,1′-biphenyl]-3-yl}-1,3,5-triazine (3.00 g, 5.11 mmol), 5-chloro-2-(naphthylene-1-yl)pyridine (1.47 g, 6.13 mmol), palladium acetate (0.023 g, 0.10 mmol) and X-Phos (0.097 g, 0.20 mmol) were dissolved in tetrahydrofuran (51 mL). To this, a 2 M aqueous solution of tripotassium phosphate (7.7 mL, 15.3 mmol) was added, and the mixture was stirred at 65° C. for 23 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL) and ethanol (50 mL). This solid was suspended in toluene (300 mL), stirred at 110° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to give the desired 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3'-[2- (Naphthylene-1-yl)pyridin-4-yl][1,1′-biphenyl]-3-yl}-1,3,5-triazine (Compound I272-2) as a white solid (yield 1.7 g, yield Rate of 53%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 9.12-9.11 (m, 1H), 9.11 (t, J=1.8 Hz, 1H), 8.91-8.84 (m , 5H), 8.25-8.22 (m, 1H), 8.17 (dd, J=8.7, 2.8Hz, 1H), 8.06 (t, J=1.8Hz, 1H). , 7.98-7.94 (m, 3H), 7.87-7.84 (m, 3H), 7.80-7.71 (m, 7H), 7.66-7.60 (m, 4H), 7.55-7.50 (m, 4H), 7.47-7.42 (m, 1H).

Synthesis Example-7

2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane under an argon stream. -2-yl)phenyl}-1,3,5-triazine (3.00 g, 5.87 mmol), 2-bromo-6-chloropyridine (1.35 g, 7.04 mmol), tetrakis(triphenylphosphine)palladium (0) (136 mg, 0.12 mmol) was suspended in tetrahydrofuran (59 mL). A 2.0 M potassium carbonate aqueous solution was added thereto, and the mixture was stirred at 65°C for 17 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL) and ethanol (50 mL). This solid was suspended in toluene (120 mL), stirred at 110° C., and allowed to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to give 2-[(1,1′-biphenyl)-4-yl]-4-phenyl-6-{3-(2-chloropidine-6). A white solid of (-yl)phenyl}-1,3,5-triazine (yield 1.9 g, yield 66%) was obtained.

Synthesis Example-18

2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3-(2-chloropydin-6-yl)phenyl}-1 obtained in Synthesis Example-7 under an argon stream. , 3,5-triazine (1.9 g, 3.88 mmol), 5,5-dimethyl-2-phenanthrenyl-1,3,2-dioxaborinane (1.46 g, 5.05 mmol), palladium acetate (0.017 g, 0.078 mmol) and X-Phos (0.074 g, 0.16 mmol) were dissolved in tetrahydrofuran (74 mL). A 2.0 M potassium carbonate aqueous solution (5.8 mL, 11.7 mmol) was added thereto, and the mixture was stirred at 65° C. for 23 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL) and ethanol (50 mL). This solid was suspended in toluene (250 mL), stirred at 110° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to give the desired 2-[(1,1′-biphenyl)-4-yl]-4-phenyl-6-{ [2-(phenanthrene- A white solid (yield 0.9 g, yield 38%) of 9-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I2-3) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 9.57 (t, J=1.8 Hz, 1 H), 8.91-8.79 (m, 8 H), 8.46 (d, J=7). 0.7 Hz, 1H), 8.40 (d, J=9.2 Hz, 1H), 8.06 (t, J=4.7 Hz, 3H), 8.02 (d, J=8.2 Hz, 1H) , 7.83 (d, J=8.9 Hz, 2H), 7.76-7.53 (m, 12H), 7.46 (t, J=6.9 Hz, 1H).

Synthesis Example-19

2-{3-(trifluoromethanesulfonyloxy)phenyl}-4,6-bis([1,1'-biphenyl]-4-yl)triazine (4.00 g, 6.56 mmol), 2 under an argon stream. -(Phenanthrene-9-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (3.0 g, 7.88 mmol), palladium acetate (0 0.029 g, 0.131 mmol) and X-Phos (0.125 g, 0.26 mmol) were dissolved in tetrahydrofuran (120 mL). A 2.0 M potassium carbonate aqueous solution (9.9 mL, 11.7 mmol) was added thereto, and the mixture was stirred at 65° C. for 20 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL) and ethanol (50 mL). This solid was suspended in toluene (1450 mL), stirred at 110° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to give the desired 2,4-bis[(1,1′-biphenyl)-4-yl]-6-{ [2-(phenanthrene-9. -Yl) Pyrimidin-5-yl]-phenyl-3-yl}-1,3,5-triazine (Compound I131-3) was obtained as a white solid (yield 2.4 g, 51%).
FDMS: 715

Synthesis Example-8

2,4-bis[(1,1′-biphenyl)-4-yl]-6-{3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-under an argon stream. 2-yl)phenyl}-1,3,5-triazine (15.0 g, 25.5 mmol), 2-bromo-6-chloropyridine (14.7 g, 76.6 mmol), tetrakis(triphenylphosphine)palladium( 0) (885 mg, 0.77 mmol) was suspended in tetrahydrofuran (260 mL). A 4 M tripotassium phosphate aqueous solution (19.2 mL, 76.6 mmol) was added thereto, and the mixture was stirred at 65° C. for 17 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL) and ethanol (150 mL). This solid was suspended in toluene (140 mL), stirred at 110° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to give 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{3-(2-chloropydin-6-. A white solid of (yl)phenyl}-1,3,5-triazine (yield 12.1 g, yield 83%) was obtained.

Synthesis Example-20

2,4-bis[(1,1'-biphenyl)-4-yl]-6-{3-(2-chloropydin-6-yl)phenyl}-1, obtained in Synthesis Example-8, under an argon stream. 3,5-triazine (12.0 g, 20.9 mmol), 5,5-dimethyl-2-phenanthrenyl-1,3,2-dioxaborinane (7.90 g, 27.2 mmol), palladium acetate (0.094 g, 0) .42 mmol) and X-Phos (0.399 g, 0.84 mmol) were dissolved in tetrahydrofuran (250 mL). To this, a 4 M aqueous solution of tripotassium phosphate (15.7 mL, 62.8 mmol) was added, and the mixture was stirred at 65°C for 6 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (150 mL) and ethanol (10 mL). This solid was suspended in toluene (800 mL), stirred at 110° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to give the desired 2,4-bis[(1,1′-biphenyl)-4-yl]-6-{ [2-(phenanthrene-9. -Yl)Pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I3-3) was obtained as a white solid (yield 9.9 g, 66%).

FDMS: 714
The glass transition temperature of compound I3-3 was 120 degreeC.

Synthesis Example-21

2,4-bis[(1,1'-biphenyl)-4-yl]-6-{3-(2-chloropydin-6-yl)phenyl}-1, obtained in Synthesis Example-8, under an argon stream. 3,5-Triazine (3.0 g, 5.24 mmol), dibenzofuran-4-boronic acid (1.22 g, 5.77 mmol), palladium acetate (0.024 g, 0.10 mmol) and X-Phos (0.100 g). , 0.210 mmol) was dissolved in tetrahydrofuran (50 mL). To this, a 4 M aqueous solution of tripotassium phosphate (3.93 mL, 15.7 mmol) was added, and the mixture was stirred at 65°C for 12 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (150 mL) and ethanol (10 mL). This solid was suspended in toluene (600 mL), stirred at 110° C., and allowed to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to give the target 2,4-bis[(1,1′-biphenyl)-4-yl]-6-{[2-(dibenzofuran-4. -Yl)Pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I3-5) was obtained as a white solid (amount 2.4 g, yield 65%).
FDMS: 705

Synthesis Example-22

2,4-bis[(1,1'-biphenyl)-4-yl]-6-{3-(2-chloropydin-6-yl)phenyl}-1, obtained in Synthesis Example-8, under an argon stream. 3,5-Triazine (3.0 g, 5.24 mmol), dibentiofene-4-boronic acid (1.55 g, 6.82 mmol), palladium acetate (0.024 g, 0.10 mmol) and X-Phos(0. .100 g, 0.210 mmol) was dissolved in tetrahydrofuran (50 mL). To this, a 4 M tripotassium phosphate aqueous solution (3.93 mL, 15.7 mmol) was added, and the mixture was stirred at 65°C for 20 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (150 mL) and ethanol (10 mL). This solid was suspended in toluene (900 mL), stirred at 110° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to give the target 2,4-bis[(1,1′-biphenyl)-4-yl]-6-{[2-(dibenzothiophene- 4-yl)Pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I3-5) was obtained as a white solid (2.5 g, 66% yield).
FDMS: 721

Synthesis Example-23

2,4-di-(naphthyl-2-yl)-6-{3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl} under argon flow -1,3,5-triazine (2.50 g, 4.67 mmol), 3-chloro-2-(anthracen-9-yl)pyridine (1.49 g, 5.13 mmol), palladium acetate (0.021 g, 0) 0.093 mmol) and X-Phos (0.089 g, 0.187 mmol) were dissolved in tetrahydrofuran (47 mL). To this, a 4 M tripotassium phosphate aqueous solution (3.50 mL, 14.0 mmol) was added, and the mixture was stirred at 65°C for 18 hours. After allowing to cool to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (100 mL) and ethanol (10 mL). This solid was suspended in toluene (400 mL), stirred at 110° C., and then left to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to give the desired 2-{[2-(anthracen-9-yl)pyridin-3-yl]phenyl-3-yl}-4,6- A white solid of di-(naphthyl-2-yl)-1,3,5-triazine (Compound I85-4) (1.2 g, 39% yield) was obtained.
FDMS: 663

Compared with ETL-3 and ETL-4 described in Patent Document 2 (see below), the cyclic azine compound according to one embodiment of the present invention has a high crystallization temperature or has a crystallization peak. Is not detected, and it is understood that it is difficult to crystallize and has high amorphousness.

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

Element Example-1 (see FIG. 2)
(Preparation of substrate 101 and anode 102)
As a substrate having an anode on its surface, a glass substrate with an ITO transparent electrode in which a 2 mm wide indium-tin oxide (ITO) film (film thickness 110 nm) was patterned in a stripe shape was prepared. Next, this substrate was washed with isopropyl alcohol and then surface-treated by ozone ultraviolet ray cleaning.

(Preparation for vacuum deposition)
Each layer was vacuum-deposited by a vacuum vapor deposition method on the substrate subjected to the surface treatment after washing to form each layer in a laminated manner.
First, the glass substrate was introduced into a vacuum vapor deposition tank, and the pressure was reduced to 1.0×10 ⁻⁴ Pa. Then, the respective layers were formed in the following order according to the film forming conditions of each layer.

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

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

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

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

(Production of First Electron Transport Layer 1071)
Sublimated and purified 2-[3′-(9,9-dimethyl-9H-fluoren-2-yl)[1,1′-biphenyl]-3-yl]-4,6-diphenyl-1,3,5- Triazine was deposited to a thickness of 6 nm at a rate of 0.05 nm/sec to form a first electron transport layer 1071.

(Production of Second Electron Transport Layer 1072)
4,6-diphenyl-2-(3'-{4-phenyl-6-[(1,1'-biphenyl)-4-yl]pyridin-2-yl}-biphenyl- synthesized in Synthesis Example-1 4-yl)-1,3,5-triazine (Compound B1-50) and Liq were formed into a 25 nm film at a ratio of 50:50 (mass ratio) to prepare a second electron transport layer 1072. The film formation rate was 0.15 nm/sec.

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

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

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

A direct current was applied to the organic electroluminescence device produced as described above, and the emission characteristics were evaluated using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse). As the emission characteristics, the current efficiency (cd/A) when a current density of 10 mA/cm ² was passed was measured, and the device life (h) during continuous lighting was measured. Incidentally, Table 3 of the device lifetime (h) measures the luminance decay time at the time of continuous lighting when driving was prepared device at an initial luminance 1000 cd / ^{m 2,} to the luminance (cd / ^{m 2)} is reduced 5% The time required for the measurement was measured. The driving voltage, the current efficiency, and the device life are relative values with the result in the device reference example 1 described later as a reference value (100). Table 3 shows the obtained measurement results.

Element Example-2
2-(3′-{4-phenyl-6-[4-(3-pyridyl)phenyl]pyridyl-2-yl synthesized in Synthesis Example-2 in place of Compound B1-50 in Device Example-1. }-1,1′-Biphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (Compound B1-75) was used in the same manner as in Example 1 except that the organic electric field was used. A light emitting device was produced and evaluated. Table 6 shows the obtained measurement results.

Device Example-3
2-{3′-[2-(1-naphthyl)-6-phenylpyridyl-4-yl]-1,1 synthesized in Synthesis Example-3 in place of Compound B1-50 in Device Example-1 An organic electroluminescent device was produced in the same manner as in Example 1 except that'-biphenyl-4-yl}-4,6-diphenyl-1,3,5-triazine (C1-57) was used. evaluated. Table 6 shows the obtained measurement results.

Device Example-4
2-{3′-[4-(1-naphthyl)-6-phenylpyridyl-2-yl]-1,1 synthesized in Synthesis Example-4 instead of Compound B1-50 in Device Example-1 An organic electroluminescent device was prepared by the same method as in Example 1 except that'-biphenyl-4-yl}-4,6-diphenyl-1,3,5-triazine (A1-57) was used, evaluated. Table 6 shows the obtained measurement results.

Element Example-5
2-(3′-{6-phenyl-2-[(1,1′-biphenyl)-4-yl]pyridine synthesized in Synthesis Example-5 instead of Compound B1-50 in Device Example-1. 2-yl}-1,1'-biphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (C1-50) except that the same method as in Example 1 was used. An organic electroluminescence device was prepared by using and evaluated. Table 6 shows the obtained measurement results.

Element Example-6
2-(3′-(2,6-diphenylpyridin-4-yl)-1,1′-biphenyl-4-synthesized in Synthesis Example-6 in place of Compound B1-50 in Device Example-1. Example 3 An organic electroluminescent device was prepared in the same manner as in Example 1 except that (i)-4-(1,1′-biphenyl)-6-phenyl-1,3,5-triazine (C2-1) was used. It was produced and evaluated, and the measurement results obtained are shown in Table 6.

Element Example-7
2-(3′-(4,6-diphenylpyridin-2-yl)-1,1′-biphenyl-4-synthesized in Synthesis Example-7 in place of Compound B1-50 in Device Example-1. Example 1 An organic electroluminescent device was prepared in the same manner as in Example 1 except that (yl)-4-(1,1′-biphenyl)-6-phenyl-1,3,5-triazine (A2-1) was used. It was produced and evaluated, and the measurement results obtained are shown in Table 6.

Element Example-8
2-[(3″-(2,6-diphenylpyridin-4-yl)-1,1′:3′ synthesized in Synthesis Example-8 instead of Compound B1-50 in Device Example-1. 1″-terphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (F13-1), except that the organic electroluminescence device was manufactured in the same manner as in the device example-1. Was prepared and evaluated. Table 6 shows the obtained measurement results.
Element Example-9
2-[(3′″-(2,6-diphenylpyridin-4-yl)-1,1′:4 synthesized in Synthesis Example-9 instead of Compound B1-50 in Device Example-1. Device implementation except that',1'':3'',1'''-quaterphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (G3-1) was used. An organic electroluminescence device was prepared and evaluated in the same manner as in Example-1. Table 6 shows the obtained measurement results.

Element reference example-1
2-[5-(9-phenanthryl)-4'-(2-pyrimidyl)biphenyl-3-yl described in JP 2011-063584 A instead of the compound B1-50 in Device Example-1. ] An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example-1 except that 4,6-diphenyl-1,3,5-triazine (ETL-2) was used. Table 6 shows the obtained measurement results.

Device Example 10
4,6-Diphenyl-2-[3′-{2-(9-phenanthryl)pyridin-6-yl}-synthesized in Synthesis Example-10 in place of Compound B1-50 in Device Example-1. 1,1′-biphenyl-4-yl]-1,3,5-triazine (Compound I171-3) was used, and an organic electroluminescent device was prepared and evaluated in the same manner as in Device Example-1. .. Table 7 shows the obtained measurement results.

Element Example-11
In Device Example-1, 4,6-diphenyl-2-[3'-{2-(9-phenanthryl)pyridin-4-yl}1 synthesized in Synthesis Example-11 was used instead of Compound B-50. , 1′-Biphenyl-4-yl]-1,3,5-triazine (Compound I179-3) was used, and an organic electroluminescent device was prepared and evaluated in the same manner as in Device Example-1. Table 7 shows the obtained measurement results.

Element Example-12
In Element Example-1, 4,6-diphenyl-2-[3'-{5-(9-phenanthrenyl)pyridin-3-yl}- synthesized in Synthesis Example-12 was used instead of Compound B-50. 1,1′-biphenyl-4-yl]-1,3,5-triazine (Compound I187-3) was used, and an organic electroluminescent device was prepared and evaluated in the same manner as in Device Example-1. .. Table 7 shows the obtained measurement results.

Element Example-13
In Device Example-1, instead of the compound B-50, 4,6-bis[(1,1'-biphenyl)-4-yl]-2-[{5-( synthesized in Synthesis Example-13 was used. Phenanthrene-9-yl)pyridin-3-yl}-phenyl-3-yl)}-1,3,5-triazine (Compound I127-3) was used in the same manner as in Example 1, except that the compound was used. An electroluminescent device was produced and evaluated. Table 7 shows the obtained measurement results.

Element Example-14
2,4-diphenyl-6-[3-(3-methyl-2-phenanthrenylpyridin-4-yl) synthesized in Synthesis Example-14 in place of Compound B-50 in Device Example-1. ) Phenyl]-1,3,5-triazine (Compound I141-3) was used, and an organic electroluminescent device was prepared and evaluated in the same manner as in Device Example-1. Table 7 shows the obtained measurement results.

Device Example-15
In Device Example-1, 2,4-diphenyl-6-[3-(2-methyl-3-phenanthrenylpyridin-6-yl) synthesized in Synthesis Example-15 was used instead of Compound B-50. ) Phenyl]-1,3,5-triazine (Compound I153-3) was used, and an organic electroluminescent device was prepared and evaluated in the same manner as in Device Example-1. Table 7 shows the obtained measurement results.

Element Example-16
In Device Example-1, instead of the compound B-50, 4,6-bis[(1,1'-biphenyl)-4-yl]-2-{3'-[synthesized in Synthesis Example-16 was used. Device implementation except that 2-(naphthylene-1-yl)pyridin-4-yl][1,1′-biphenyl]-3-yl}-1,3,5-triazine (Compound I273-2) was used. An organic electroluminescence device was prepared and evaluated in the same manner as in Example-1. Table 7 shows the obtained measurement results.

Element Example-17
2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3'- synthesized in Synthesis Example-17 in place of Compound B-50 in Device Example-1. A device other than using [2-(naphthylene-1-yl)pyridin-4-yl][1,1′-biphenyl]-3-yl}-1,3,5-triazine (Compound I272-2). An organic electroluminescence device was prepared and evaluated by the same method as in Example-1. Table 7 shows the obtained measurement results.

Element Example-18
In Device Example-1, instead of Compound B-50, 2-[(1,1′-biphenyl)-4-yl]-4-phenyl-6-{ [2- An organic electric field was produced in the same manner as in Example 1 except that (phenanthrene-9-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I2-3) was used. A light emitting device was produced and evaluated. Table 7 shows the obtained measurement results.

Element Example-19
In Element Example-1, 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{[2-( was synthesized in Synthesis Example-19 instead of Compound B-50. Phenanthrene-9-yl)pyrimidin-5-yl]-phenyl-3-yl}-1,3,5-triazine (Compound I131-3) was used in the same manner as in Example 1 except that the organic electric field was used. A light emitting device was produced and evaluated. Table 7 shows the obtained measurement results.

Element Example-20
2,4-Bis[(1,1′-biphenyl)-4-yl]-6-{ [2-(Synthesis Example 20 was replaced with Compound B-50 in Element Example-1. Organic electroluminescence was performed in the same manner as in Example 1 except that phenanthrene-9-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I3-3) was used. A device was prepared and evaluated. Table 7 shows the obtained measurement results.

Element Example-21
In Device Example-1, 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{[2-( was synthesized in Synthesis Example-21 instead of the compound B-50. Organic electroluminescence was performed in the same manner as in Example 1 except that dibenzofuran-4-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I3-5) was used. A device was prepared and evaluated. Table 7 shows the obtained measurement results.

Element Example-22
2,4-Bis[(1,1′-biphenyl)-4-yl]-6-{ [2-(Synthesis Example 22 instead of Compound B-50 in Device Example-1) Dibenzothiophen-4-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I3-6) was used in the same manner as in Example 1 except that the organic electric field was used. A light emitting device was produced and evaluated. Table 7 shows the obtained measurement results.

Element Example-23
In Device Example-1, instead of Compound B-50, 2-{[2-(anthracen-9-yl)pyridin-3-yl]phenyl-3-yl}-4 synthesized in Synthesis Example-23. , 6-Di-(naphthyl-2-yl)-1,3,5-triazine (Compound I85-4) was used, and an organic electroluminescent device was prepared and evaluated in the same manner as in Device Example-1. did. Table 7 shows the obtained measurement results.

Element reference example-2
2,4-bis[(1,1'-biphenyl)-4-yl]-6-[4'-(3 described in Patent Document 2 instead of Compound B-50 in Device Example-1. -Pyridyl)1,1'-biphenyl-4-yl]-1,3,5-triazine (ETL-3) was used to produce an organic electroluminescent device by the same method as in Device Example-1. evaluated. Table 2 shows the obtained measurement results.

Element reference example-3
2,4-bis[(1,1'-biphenyl)-4-yl]-6-[4'-(4 described in Patent Document 2 in place of the compound B-50 in Device Example-1. -Pyridyl)1,1'-biphenyl-4-yl]-1,3,5-triazine (ETL-4) was used to produce an organic electroluminescence device by the same method as in Device Example-1. evaluated. Table 2 shows the obtained measurement results.

The cyclic azine compounds (1), (11), and (21) according to one embodiment of the present invention have extremely excellent heat resistance of the film quality, and by using the compound, an organic electroluminescence device excellent in long life and current efficiency can be obtained. Can be provided.
Further, the cyclic azine compounds (1), (11), and (21) according to one embodiment of the present invention are used as an electron transport material for an organic electroluminescence device which is excellent in low driving voltage. Furthermore, the cyclic azine compounds (1), (11), and (21) can provide an organic electroluminescence device with low power consumption.
In addition, the cyclic azine compound according to one embodiment of the present invention provides a material that has excellent operability in sublimation purification because it has good thermal stability during sublimation purification, and has few impurities that cause element deterioration of the organic electroluminescent element. can do. In addition, the cyclic azine compound according to one embodiment of the present invention is excellent in stability of a deposited film, and thus can provide an organic electroluminescence device having a long life.
Further, the thin film comprising the cyclic azine compound (1), (11), and (21) according to one embodiment of the present invention has an electron transporting ability, a hole blocking ability, a redox resistance, water resistance, oxygen resistance, and electron injection. Since it has excellent characteristics and the like, it is useful as a material for an organic electroluminescence device, and is also useful as an electron transport material, a hole blocking material, a light emitting host material and the like. It is especially useful when used as an electron transport material.
In addition, the cyclic azine compounds (1), (11), and (21) according to one embodiment of the present invention have wide band gaps and high triplet excitation levels, and therefore, not only conventional fluorescent device applications, It can be suitably used for a phosphorescent device and an organic electroluminescent device utilizing thermally activated delayed fluorescence (TADF).

1,101 Substrate 2,102 Anode 3,103 Hole injection layer
4 Charge Generation Layer 5,105 Hole Transport Layer 6,106 Light Emitting Layer 7,107 Electron Transport Layer 8,108 Cathode 51,1051 First Hole Transport Layer 52,1052 Second Hole Transport Layer 71,1071 First Electron Transport layer 72,1072 Second electron transport layer
100 organic electroluminescent device

Claims (22)

The cyclic azine compound represented by the formula (1):

In formula (1),
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenyl group, or a naphthyl group;
X ^{1 to} X ⁵ each independently represent C—Ar ³ , C—R, or a nitrogen atom;
One or two of X ^{1 to} X ⁵ are nitrogen atoms;
One or 2 in X ¹ to X ⁵ is a C-Ar ^3;
Ar ³ is
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 24 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ³ is 4 to 25;
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
L ¹ represents a phenylene group or a single bond;
n ¹ represents 0, 1, or 2;
When only one of X ^{1 to} X ⁵ is C-Ar ³ and either one of X ¹ and X ⁵ is C-Ar ³ ,
L ¹ is a single bond,
n ¹ is 0 or 1;
When only one of X ^{1 to} X ⁵ is C-Ar ³ and any one of X ² , X ³ and X ⁴ is C-Ar ³ ,
L ¹ is a phenylene group or a single bond,
n ¹ is 0, 1, or 2;
In the case where two of X ^{1 to} X ⁵ are C-Ar ³ ,
Of X ¹ , X ³ , and X ⁵ , one is a nitrogen atom and the other two are C—R,
X ² and X ⁴ are C—Ar ³ ;
L ¹ is a phenylene group or a single bond,
n ¹ is 1 or 2;
The two C—R and the two C—Ar ³ may be the same or different;
The groups represented by Ar ¹ , Ar ² and Ar ³ are each independently a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms. It may have one or more groups selected from the group consisting of a group and an alkoxy group having 1 to 4 carbon atoms. The compound according to claim 1, wherein only one of X ^{1 to} X ⁵ is a nitrogen atom. Ar ³ is one selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. It may have the above groups, phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, chrysenyl group, acenaphthyl group The cyclic azine compound according to claim 1 or 2, which is a group, a pyrimidyl group, a pyrazyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, or a dibenzothienyl group. The cyclic azine compound represented by the formula (11):

In formula (11),
Ar ¹¹ and Ar ¹² each independently represent a phenyl group or a naphthyl group;
Ar ¹³ and Ar ¹⁴ are each independently
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 24 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ¹³ and Ar ¹⁴ is 4 to 25;
L ¹¹ represents a phenylene group or a single bond;
One of Z ¹¹ and Z ¹² represents a nitrogen atom, and the other represents C—H;
n ¹¹ is 1 or 2.
Each group represented by Ar ^{11 to} Ar ¹⁴ is independently a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. It may have one or more groups selected from the group consisting of 4 alkoxy groups. Ar ¹¹ and Ar ¹² are each independently a phenyl group or a naphthyl group;
The cyclic azine compound according to claim 4, wherein when each group represented by Ar ¹¹ and Ar ¹² is a phenyl group, the phenyl group may independently have a phenyl group. The cyclic azine compound according to claim 4 or 5, wherein neither Ar ¹³ nor Ar ¹⁴ has a substituent. The cyclic azine compound according to any one of claims 5 to 6, wherein the total number of ring-constituting carbon atoms of Ar ¹³ and Ar ¹⁴ is 4 to 20, respectively. The cyclic azine compound according to any one of claims 4 to 7, wherein the total of the total number of ring-constituting carbon atoms of Ar ¹³ and the total number of ring-constituting carbon atoms of Ar ¹⁴ is 8 to 32. Ar ¹³ and Ar ¹⁴ are each independently a phenyl group, p-tolyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-(2-pyridyl)phenyl group. , 4-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group , 2-(1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group , 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 3-(3-fluoranthenyl) Phenyl group, 4-(3-fluoranthenyl)phenyl group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group, 3-(3-quinolyl)phenyl group, 4-(3- (Quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8- Quinolyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 3 -(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 2-pyridyl group, 3- Pyridyl group, 4-pyridyl group, 1-naphthyl group, 2-naphthyl group, 3-quinolyl group, 8-quinolyl group, 2-benzothienyl group, 2-benzofuryl group, 9-anthryl group, 9-phenanthryl group, 2 The cyclic azine compound according to any one of claims 4 to 8, which is a -dibenzothienyl group, a 2-dibenzofuryl group, a 4-dibenzothienyl group, or a 4-dibenzofuryl group. The cyclic azine compound according to any one of claims 4 to 9, wherein n ¹¹ is 1. The cyclic azine compound according to claim 4, wherein L ¹¹ is a single bond. The cyclic azine compound represented by the formula (21):

In formula (21),
Ar ²¹ and Ar ²² each independently represent a phenyl group, a biphenyl group, or a naphthyl group;
X ^{21 to} X ²⁵ each independently represent C—Ar ²³ , C—R, or a nitrogen atom;
In X ^{21 to} X ²⁵ , one or two are nitrogen atoms;
Ar ²³ is
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 18 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ²³ is 4 to 25;
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
Only one of X ^{21 to} X ²⁵ is C-Ar ²³ ;
Among X ²¹ to X ^25, if either one of ^{X 21} and ^{X 25} are ^{C-Ar 23} is,
L ²¹ is a single bond,
n ²¹ is 0 or 1;
When any one of X ^{22 to} X ²⁴ is C—Ar ²³ among X ^{21 to} X ²⁵ ,
L ²¹ is a phenylene group or a single bond,
n ²¹ is 0, 1, or 2;
Each group represented by Ar ^{21 to} Ar ²³ may be independently substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group. The cyclic azine compound according to claim 12, which is represented by formula (22):

In formula (22),
Ar ²¹ and Ar ²² each independently represent a phenyl group, a biphenyl group, or a naphthyl group;
Y ^{21 to} Y ²⁵ each independently represent C—Ar ²³ , C—R, or a nitrogen atom;
Only one of Y ^{21 to} Y ²⁵ is a nitrogen atom;
Ar ²³ is
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 18 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ²³ is 4 to 25;
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
Only one of Y ^{21 to} Y ²⁵ is C-Ar ²³ ;
Of Y ²¹ to Y ^25, if either one of ^{Y 21} and ^{Y 25} are ^{C-Ar 23} is,
L ²¹ is a single bond,
n ²¹ is 0 or 1;
When any one of Y ^{22 to} Y ²⁴ is C—Ar ²³ among Y ^{21 to} Y ²⁵ ,
L ²¹ is a phenylene group or a single bond,
n ²¹ is 0, 1, or 2;
Each group represented by Ar ^{21 to} Ar ²³ may be independently substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group. The cyclic azine compound according to claim 12, which is represented by the formula (23):

In formula (23),
Ar ²¹ and Ar ²² each independently represent a phenyl group, a biphenyl group, or a naphthyl group;
Z ^{21 to} Z ²⁵ each independently represent C—Ar ²³ , C—R, or a nitrogen atom;
Two of Z ^{21 to} Z ²⁵ are nitrogen atoms;
Ar ²³ is
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 18 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ²³ is 4 to 25;
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
Only one of Z ^{21 to} Z ²⁵ is C-Ar ²³ ;
When one of Z ²¹ and X ²⁵ is C—Ar ²³ among Z ^{21 to} Z ²⁵ ,
L ²¹ is a single bond,
n ²¹ is 0 or 1;
When any one of Z ^{22 to} Z ²⁴ is C—Ar ²³ in Z ^{21 to} X ²⁵ ,
L ²¹ is a phenylene group or a single bond,
n ²¹ is 0, 1, or 2;
Each group represented by Ar ^{21 to} Ar ²³ may be independently substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group. The cyclic azine compound according to claim 12, which is represented by formula (24), (25), (26) or (27):

In the formula,
Ar ²¹ and Ar ²² each independently represent a phenyl group, a biphenyl group or a naphthyl group;
Ar ²³ is
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 18 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ²³ is 4 to 25;
V each independently represents C—R;
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
L ²¹ is a phenylene group or a single bond;
n ²¹ is an integer of 0, 1 or 2.
Each group represented by Ar ^{21 to} Ar ²³ may be independently substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group. The cyclic azine compound according to claim 12, which is represented by formula (28), (29), (30) or (31):

In the formula,
Ar ²¹ and Ar ²² each independently represent a phenyl group, a biphenyl group or a naphthyl group;
Ar ²³ is
A monocycle which may be linked, a condensed ring which may be linked, or a structure in which these are linked,
(I) an aromatic hydrocarbon group having 6 to 18 carbon atoms,
(Ii) a nitrogen-containing heteroaromatic group having only 4 to 6 carbon atoms and having 4 to 25 carbon atoms, or
(Iii) a heteroaromatic group having 4 to 25 carbon atoms, which is composed of atoms selected from the atomic group consisting of H, C, O, and S, or
(Iv) represents a group composed of any combination of two or more selected from the above (i) to (iii);
The total number of ring-constituting carbon atoms of Ar ²³ is 4 to 25;
W's each independently represent C—R;
R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
L ²¹ is a phenylene group or a single bond;
n ²¹ is an integer of 0, 1 or 2.
Each group represented by Ar ^{21 to} Ar ²³ may be independently substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group. The cyclic azine compound according to any one of claims 12 to 16, wherein Ar ²¹ and Ar ²² are the same as each other. The cyclic azine compound according to any one of claims 12 to 16, wherein Ar ²¹ and Ar ²² are different from each other. The cyclic azine compound according to any one of claims 12 to 18, wherein L ²¹ is a single bond. Ar ²³ is a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a perylenyl group, which may be substituted with a fluorine atom, a methyl group or a phenyl group. The cyclic azine compound according to any one of claims 12 to 19, which is a chrysenyl group, an acenaphthyl group, a benzothienyl group, a dibenzofuryl group, or a dibenzothienyl group. A material for an organic electroluminescence device, which comprises the cyclic azine compound according to any one of claims 1 to 20. An organic electroluminescent device comprising the cyclic azine compound according to claim 1.

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