JP6977325B2 - Triazine compounds, their manufacturing methods, and organic electroluminescent devices containing them as constituents. - Google Patents

Description

The present invention relates to a triazine compound, a method for producing the same, and an organic electroluminescent device containing the triazine compound. More specifically, the present invention relates to a triazine compound useful as a material for an organic electric field light emitting device, which is characterized by a structure in which a diarylpyridyl group is combined with a triazine skeleton via a meta bond or an ortho bond, and a method for producing the triazine compound. It relates to a highly efficient, low voltage and highly durable organic triazine light emitting element, which is characterized by being used in at least one layer.

The organic electroluminescent element has a basic configuration in which a light emitting layer containing a light emitting material is sandwiched between a hole transport layer and an electron transport layer, and an anode and a cathode are attached to the outside thereof, and holes injected into the light emitting layer are formed. It is a light emitting element that utilizes the emission of light (fluorescence or phosphorescence) when the exciter generated by the recombination of electrons is deactivated, and is already used not only for small displays but also for large televisions and lighting. .. The hole transport layer is a hole transport layer and a hole injection layer, the light emitting layer is an electron block layer, a light emitting layer and a hole block layer, and the electron transport layer is an electron transport layer and an electron injection layer. It may be divided and configured. Further, as the carrier transport layer (electron transport layer or hole transport layer) of the organic electroluminescent element, a co-deposited film doped with a metal, an organic metal compound or another organic compound may be used.

Conventional organic electroluminescent devices have a higher drive voltage, lower light emission luminance and light emission efficiency, and significantly lower device life than inorganic light emitting diodes, and have not been put into practical use. Although recent organic electroluminescent devices have been gradually improved, more excellent materials are required in terms of luminous efficiency characteristics, drive voltage characteristics, and long life characteristics. Further, high heat resistance may be required depending on the application such as in-vehicle application, and the material is required to have a high glass transition temperature (Tg).

Examples of the electron transport material having excellent long life for an organic electroluminescent device include a triazine compound disclosed in Patent Document 1. However, further improvements have been required in terms of voltage, life and luminous efficiency of the organic electroluminescent device using the material.

Patent Document 2 discloses a triazine compound having a diarylpyridyl group and the like. The compound is excellent in terms of increasing the luminous efficiency of the organic electroluminescent element, but further improvement in luminous efficiency has been required.

Japanese Unexamined Patent Publication No. 2011-063584 WO2016 / 002864 Gazette

An object of the present invention is to provide an electron transport material having excellent heat resistance of a film material and excellent low voltage driveability, luminous efficiency or long life of an organic electroluminescent element.

As a result of diligent studies to solve the above problems, the present inventors have conducted a triazine compound in which a diarylpyridyl group and a triazine site are bonded via a meta-bond or an ortho-bond (hereinafter, also referred to as "triazine compound (1)"). The heat resistance of the film quality is high, and the organic electric field light emitting element using the compound as an electron transport material has a lower voltage, higher light emission efficiency, or longer life than when a conventionally known material is used. We found that and came to complete the invention of the present application.

That is, the present invention has the general formula (1).

(In general formula (1),
Ar ¹ is phenyl, or naphthyl group (these groups, a fluorine atom, a methyl group, or may be substituted by a phenyl group) represent the two Ar ¹ are identical.
Ar ² , Ar ³ , Ar ⁵ , and Ar ⁶ each independently have (a) a monocyclic or fused aromatic hydrocarbon group having 6 to 24 carbon atoms, and (b) 3 carbon atoms consisting only of a 6-membered ring. Monocyclic or fused ring heteroaromatic group with 3 to 25 carbon atoms composed of atoms selected from the atomic group consisting of a monocyclic or condensed ring nitrogen-containing heteroaromatic group of ~ 25, (c) H, C, O, and S. The aromatic group (the group represented by the (a), (b), and (c) is a phenyl group, a trill group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an aromatic group. It may have an alkoxy group having 1 to 4 carbon atoms), or represents a single bond.
Ar ⁴ and Ar ⁷ are independently composed of (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, and (b) a monocyclic ring having 3 to 25 carbon atoms consisting of only a 6-membered ring. A condensate nitrogen-containing heteroaromatic group or (c) a monocyclic or condensate heteroaromatic group having 3 to 25 carbon atoms composed of atoms selected from the atomic group consisting of H, C, O, and S (the said. The groups represented by (a), (b), and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). ..
The total number of ring-constituting carbon atoms of Ar ² , Ar ³ , and Ar ⁴ and the total number of ring-constituting carbon atoms of Ar ⁵ , Ar ⁶ , and Ar ⁷ are all 5 to 25.
A represents a single bond.
B ¹ and B ² represent a single bond or a hydrogen atom. However, ^{either B 1} or B ² represents a single bond to form a single bond with A, and the other represents a hydrogen atom.
Z ¹ and Z ² each independently represent a nitrogen atom or CH. However, ^{either Z 1} or Z ² represents a nitrogen atom, and the other represents CH. )
It relates to a triazine compound represented by (1), a method for producing the same, and an organic electroluminescent device using the same.

According to the present invention, it is possible to provide a triazine compound having excellent heat resistance of a film quality, and to provide an organic electroluminescent element having excellent low voltage, luminous efficiency, or long life.

Hereinafter, the present invention will be described in detail.

The present invention relates to the above-mentioned triazine compound (1), a method for producing the same, and a material for an organic electroluminescent device using the material.

The substituents in the triazine compound (1) of the present invention are defined as follows.

In formula (1), Ar ¹ is a phenyl group, or naphthyl group (these groups, a fluorine atom, a methyl group, or may be substituted by a phenyl group) represent the two Ar ¹ are identical ..

The ^{phenyl group or naphthyl group substituted with a fluorine atom in Ar 1} is not particularly limited, but a fluorophenyl group, a pentafluorophenyl group, a difluorophenyl group, a fluoronaphthyl group, a difluoronaphthyl group and the like can be used. A preferred example is given.

The ^{phenyl group or naphthyl group substituted with a methyl group in Ar 1} is not particularly limited, and examples thereof include a tolyl group, a methylnaphthyl group, a dimethylphenyl group, and a dimethylnaphthyl group.

The ^{phenyl group or naphthyl group substituted with a phenyl group in Ar 1} is not particularly limited, and examples thereof include a biphenyl group, a phenylnaphthyl group, a terphenyl group, and a diphenylnaphthyl group.

Ar ¹ is more preferably a phenyl group, a tolyl group, a naphthyl group, or a biphenyl group in that it is excellent in electron transporting material properties, and further preferably a phenyl group in that it is easy to synthesize.

Specific examples of Ar ¹ are not particularly limited, but are phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, and the like. Mesityl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,4-difluorophenyl group, 3,5-difluorophenyl group, biphenyl-2-yl group, biphenyl-3-yl group , Biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl group, 4'-methylbiphenyl-4-yl group, 2,2'-dimethylbiphenyl-4- Il group, 2', 4', 6'-trimethylbiphenyl-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, 2', 4', 6'-trimethylbiphenyl-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, 2', 4', 6'-trimethylbiphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalen-2-yl group, 1-phenylnaphthalene-3-yl group, 1-phenylnaphthalene-4 -Il group, 1-Phenylnaphthalen-5-Il group, 1-Phenylnaphthalen-6-Il group, 1-Phenylnaphthalen-7-Il group, 1-Phenylnaphthalen-8-Il group, 2-Phenylnaphthalen-1 -Il group, 2-Phenylnaphthalen-3-yl group, 2-Phenylnaphthalene-4-Il group, 2-Phenylnaphthalen-5-Il group, 2-Phenylnaphthalen-6-Il group, 2-Phenylnaphthalene-7 -Il group, 2-Phenylnaphthalen-8-Il group, 1-Methylnaphthalen-4-Il group, 1-Methylnaphthalen-5-Il group, 1-Methylnaphthalen-6-Il group, 1-Methylnaphthalen-7 -Il group, 1-methylnaphthalen-8-yl group, 2-methylnaphthalen-1-yl group, 2-methylnaphthalen-3-yl group, 2-methylnaphthalen-4-yl group, 2-methylnaphthalen-5 -Il group, 2-methylnaphthalen-6-yl group, 2-methylnaphthalen-7-yl group, 2-methylnaphthalen-8-yl group, etc. are preferable. A good example is. Among these substituents, a phenyl group, a p-tolyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, or a 2-naphthyl group are excellent in terms of excellent electron transporting material properties. Preferably, a phenyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, or a 2-naphthyl group is more preferable.

Ar ² , Ar ³ , Ar ⁵ , and Ar ⁶ each independently have (a) a monocyclic or fused aromatic hydrocarbon group having 6 to 24 carbon atoms, and (b) 3 carbon atoms consisting only of a 6-membered ring. Monocyclic or fused ring heteroaromatic group with 3 to 25 carbon atoms composed of atoms selected from the atomic group consisting of a monocyclic or condensed ring nitrogen-containing heteroaromatic group of ~ 25, (c) H, C, O, and S. The aromatic group (the group represented by the (a), (b), and (c) is a phenyl group, a trill group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an aromatic group. It may have an alkoxy group having 1 to 4 carbon atoms), or represents a single bond.

Ar ² , Ar ³ , Ar ⁵ , and Ar ⁶ may be the same or different.

The ^{(a) monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms in Ar 2} , Ar ³ , Ar ⁵ , and Ar ⁶ is not particularly limited, but a phenyl group, a naphthyl group, and the like. Preferred examples include a phenanthryl group, an anthryl group, a pyrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, an acenaphthyl group, a fluorenyl group, a benzofluorenyl group and the like. As described above, these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. You may.

The monocyclic or condensed ring-containing nitrogen-containing heteroaromatic group having (b) 6-membered rings and having only 6-membered rings in ^{Ar 2} , Ar ³ , Ar ⁵ , and Ar ^{6 is not particularly limited.} , Pyridyl group, Pyrazine group, Pyrimidyl group, Pyridadyl group, Triazyl group, Kinolyl group, Isoquinolyl group, Phenantridyl group, Benzoquinolyl group, Acridinyl group and the like are preferable examples. The carbazolyl group is a heteroaromatic group containing a 5-membered ring, and is not included in a monocyclic or condensed ring-containing nitrogen-containing heteroaromatic group having only a 6-membered ring of the present invention and having 3 to 25 carbon atoms. Further, as described above, these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. You may.

A monocyclic or condensed ring heteroaromatic having 3 to 25 carbon atoms composed of atoms selected from the atomic group consisting of (c) H, C, O, and S in Ar ² , Ar ³ , Ar ⁵ , and Ar ^6. The group group is not particularly limited, and preferred examples include a thienyl group, a frill group, a bitienyl group, a bifuryl group, a benzothienyl group, a benzofuryl group, a dibenzothienyl group, a dibenzofuryl group and the like. As described above, these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. You may.

The alkyl group having 1 to 4 carbon atoms in Ar ² , Ar ³ , Ar ⁵ , and Ar ⁶ is not particularly limited, but is a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and the like. Alternatively, a t-butyl group or the like is given as a preferable example.

The alkoxy group having 1 to 4 carbon atoms in Ar ² , Ar ³ , Ar ⁵ , and Ar ⁶ is not particularly limited, but is methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-. A butoxy group, a t-butoxy group and the like are preferable examples.

Ar ⁴ and Ar ⁷ are independently composed of (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, and (b) a monocyclic ring having 3 to 25 carbon atoms consisting of only a 6-membered ring. A condensate nitrogen-containing heteroaromatic group or (c) a monocyclic or condensate heteroaromatic group having 3 to 25 carbon atoms composed of atoms selected from the atomic group consisting of H, C, O, and S (the said. The groups represented by (a), (b), and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). ..

In Ar ⁴ and Ar ⁷ , (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, and (b) a monocyclic or condensed ring containing nitrogen having 3 to 25 carbon atoms consisting of only a 6-membered ring. A monocyclic or condensed ring heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from an atomic group consisting of a heteroaromatic group (c) H, C, O, and S, having 1 to 4 carbon atoms. The constituent requirements of the alkyl group and the alkoxy group having 1 to 4 carbon atoms are synonymous with ^{Ar 2} , Ar ³ , Ar ⁵ , and Ar ^6.

From the above, the ^{group represented by −Ar 2} −Ar ³ −Ar ⁴ and the group represented by −Ar ⁵ −Ar ⁶ −Ar ⁷ are not particularly limited, but for example, in particular. For example, but not limited to, phenyl group, biphenyl group, terphenyl group, naphthylphenyl group, phenanthrylphenyl group, anthrylphenyl group, pyrenylphenyl group, triphenylphenyl group, chrysenylphenyl group, Fluolanthenylphenyl group, acenaphtylphenyl group, fluorenylphenyl group, naphthylbiphenyl group, naphthyl group, phenylnaphthyl group, biphenylnaphthyl group, phenanthrylnaphthyl group, anthrylnaphthyl group, phenanthryl group, phenylphenanthryl Group, naphthylphenanthryl group, anthryl group, phenylanthryl group, naphthyl anthryl group, pyrenyl group, phenylpyrenyl group, triphenylenyl group, phenyltriphenylenyl group, chrysenyl group, phenylcrisenyl group, fluoranthenyl Phenylfluoranthenyl group, acenaphtyl group, phenylacenaphthyl group, fluorenyl group, phenylfluorenyl group, benzofluorenyl group, fluorophenyl group, pentafluorophenyl group, fluorobiphenyl group, fluoroterphenyl group, fluoro Naftylphenyl group, naphthylfluorophenyl group, fluorophenanthrylphenyl group, phenanthrylfluorophenyl group, fluoroanthrylphenyl group, anthrylfluorophenyl group, fluoropyrenylphenyl group, pyrenylfluorophenyl group, fluorotriphenyl Phenyl group, triphenylfluorophenyl group, fluorocrisenylphenyl group, chrysenylfluorophenyl group, fluorofluoranthenylphenyl group, fluoranthenfluorophenyl group, fluoroacenaphtylphenyl group, acenaphtylfluorophenyl group, fluoro Fluolenylphenyl group, fluorenylfluorophenyl group, fluoronaphthylbiphenyl group, naphthylfluorobiphenyl group, fluoronaphthyl group, fluorophenylnaphthyl group, phenylfluoronaphthyl group, fluorobiphenylnaphthyl group, biphenylfluoronaphthyl group, fluorophenan Trillnaphthyl group, phenanthrylfluoronaphthyl group, fluoroanthrylnaphthyl group, anthrylfluoronaphthyl group, fluorophenanthril group, fluorophenylphenant Lil group, phenylfluorophenanthryl group, fluoronaphthylphenanthryl group, naphthylfluorophenanthryl group, fluoroanthryl group, fluorophenylanthryl group, phenylfluoroanthryl group, fluoronaphthyl anthryl group, naphthylfluoroan Trill group, fluoropyrenyl group, fluorophenylpyrenyl group, phenylfluoropyrenyl group, fluorotriphenylenyl group, fluorophenyltriphenylenyl group, phenylfluorotriphenylenyl group, fluorocrisenyl group, fluorophenylcrisenyl group , Phenylfluoroclysenyl group, Fluorofluoranthenyl group, Fluorophenylfluoranthenyl group, Phenylfluorofluoranthenyl group, Fluoroacenaphthyl group, Fluorphenylacenaphthyl group, Phenylfluoroacenaphthyl group, Fluorofluorenyl group , Fluorophenylfluorenyl group, phenylfluorofluorenyl group, fluorobenzofluorenyl group, pyridyl group, pyrazil group, pyrimidyl group, pyridadyl group, triazil group, quinolyl group, isoquinolyl group, phenanthridyl group, benzoquinolyl group , Acridinyl group, pyridylphenyl group, pyrazilphenyl group, pyrimidylphenyl group, pyridadylphenyl group, triazilphenyl group, quinolylphenyl group, isoquinolylphenyl group, phenanthridylphenyl group, benzoquinolyl Phenyl group, acridinylphenyl group, (phenylpyridyl) phenyl group, (naphthylpyridyl) phenyl group, pyridylbiphenyl group, pyrazilbiphenyl group, pyrimidylbiphenyl group, pyridadylbiphenyl group, triazilbiphenyl group, quino Lilbiphenyl group, isoquinolylbiphenyl group, phenanthridylbiphenyl group, benzoquinolylbiphenyl group, acridinylbiphenyl group, pyridylterphenyl group, pyrazilterphenyl group, pyrimidylterphenyl group, pyridazylterphenyl group Group, Triazyl terphenyl group, Pyridyl naphthyl group, Pyrazyl naphthyl group, Pyrimidyl naphthyl group, Pyridazyl naphthyl group, Triazyl naphthyl group, Kinolyl naphthyl group, Isoquinolyl naphthyl group, Phenantridyl naphthyl group, Benzo Kinolylnaphthyl group, acridinylnaphthyl group, phenylpyridyl group, biphenylpyridyl group, naphthylpyridyl group, phenanthrylpyridyl group, anthrylpyridyl group, pyrenylpyridyl group, triphenyle Nylpyridyl group, chrysenylpyridyl group, fluoranthenylpyridyl group, acenaphthylpyridyl group, fluorenylpyridyl group, thienyl group, frill group, bitienyl group, bifuryl group, benzothienyl group, benzofuryl group, dibenzothienyl group, dibenzo Frill group, thienylphenyl group, frillphenyl group, bitienylphenyl group, bifurylphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, thienylbiphenyl group, frillbiphenyl group, benzo Thienylbiphenyl group, benzofurylbiphenyl group, dibenzothienylbiphenyl group, dibenzofurylbiphenyl group, thienylnaphthyl group, frillnaphthyl group, benzothienylnaphthyl group, benzofurylnaphthyl group, dibenzothienylnaphthyl group, dibenzofurylnaphthyl group, phenylthienyl group , Phenylfuryl group, biphenylthienyl group, biphenylfuryl group, naphthylthienyl group, naphthylfuryl group, phenanthrylthionyl group, phenanthrylfuryl group, anthrylthionyl group, anthrylfuryl group, pyrenylthionyl group, pyrenylfuryl group, trife Nirenyl thienyl group, triphenylenyl frill group, chrysenyl thienyl group, chrysenyl frill group, fluoranthenyl thienyl group, fluoranthenyl frill group, acenafutyl thienyl group, acenaphtyl frill group, fluorenyl thienyl group, or full Preferable examples include the olenylfuryl group.

In addition, Ar ² , Ar ³ , Ar ⁵ , and Ar ⁶ are independently (a) monocyclic or condensed aromatic hydrocarbon groups having 6 to 24 carbon atoms in that they are excellent in electron transporting material properties. , (B') composed of a monocyclic or condensed ring-containing nitrogen-containing heteroaromatic group consisting of only a 6-membered ring and having 3 to 11 carbon atoms, and (c) an atom selected from an atomic group consisting of H, C, O, and S. The monocyclic or condensed ring heteroaromatic group having 3 to 25 carbon atoms (the groups represented by the (a), (b'), and (c) are a phenyl group, a trill group, a pyridyl group, and a methylpyridyl. It may have a group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or is preferably a single bond, and for Ar ⁴ and Ar ⁷ . Independently, (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, and (b') a monocyclic or condensed ring nitrogen-containing hetero having 3 to 11 carbon atoms consisting of only a 6-membered ring. An aromatic group or a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the atomic group consisting of (c) H, C, O, and S (the (a), The group represented by b') and (c) is preferably a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).

In the description of the preferred range, it is composed of (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, and (c) an atom selected from the atomic group consisting of H, C, O, and S. A monocyclic or condensed ring heteroaromatic group having 3 to 25 carbon atoms, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms have the same meanings as described above.

The monocyclic or condensed ring nitrogen-containing heteroaromatic group having only the (b') 6-membered ring and having only the (b') 6-membered ring in the preferred range is not particularly limited, but is a pyridyl group or a pyrazil group. , Pyrimidyl group, pyridadyl group, triazil group, quinolyl group, isoquinolyl group and the like are preferable examples. The carbazolyl group is a heteroaromatic group having 12 carbon atoms, and is not included in the monocyclic or condensed ring nitrogen-containing heteroaromatic group having only 6-membered rings of the present invention and having 3 to 11 carbon atoms. Further, as described above, these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. You may.

Ar ² , Ar ³ , Ar ⁵ , and Ar ⁶ are independently phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, respectively, in that they have excellent electron transporting material properties. Pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, triazil group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group benzofuranyl group, benzothienyl group, dibenzofuranyl group or dibenzothienyl group (these). The group may have a phenyl group, a trill group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond. More preferably, Ar ⁴ and Ar ⁷ are independently phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group and fluorane. Tenyl group, triphenylenyl group, triazil group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (these groups are fluorine atom, carbon). It may have an alkyl group having 1 to 4 or an alkoxy group having 1 to 4 carbon atoms).

In addition, Ar ² , Ar ³ , Ar ⁵ , and Ar ⁶ are independently phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, and pyrenyl group because they are easy to synthesize. Group, perylenyl group, fluoranthenyl group, triphenylenyl group, triazil group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (these groups) May have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar ⁴ and Ar ⁷ Independently, each of them has a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a peryleneyl group, a fluoranthenyl group, a triphenylenyl group, a triazyl group, a pyrimidyl group and a piperazyl group. , Pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (these groups are a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms). It may have an alkoxy group of).

Further, the ^{group represented by −Ar 2} −Ar ³ −Ar ⁴ and the group represented by −Ar ⁵ −Ar ⁶ −Ar ⁷ are independently phenyl in terms of excellent electron transporting material properties. Group, biphenyl group, naphthylphenyl group, phenanthrylphenyl group, fluoranthenylphenyl group, pyridylphenyl group, pyrimidylphenyl group, quinolylphenyl group, thienylphenyl group, frillphenyl group, benzothienylphenyl group, benzo Frillphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, benzothienyl More preferably, it is a group, a benzofuryl group, a phenanthryl group, an anthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group), and each of them independently. Phenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimi Being a zirdibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, phenanthryl group, dibenzothienyl group, or dibenzofuryl group (these groups may be substituted with a methyl group). Is even more preferable.

Further, the ^{groups represented by −Ar 2} −Ar ³ −Ar ⁴ and the groups represented by −Ar ⁵ −Ar ⁶ −Ar ⁷ are easy to synthesize and have high heat resistance of the film quality. Either of the groups represented by −Ar ² −Ar ³ −Ar ⁴ or the groups represented by −Ar ⁵ −Ar ⁶ −Ar ⁷ is a phenyl group, a biphenyl group, a naphthylphenyl group, or a phenanthrylphenyl. Group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, A bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group), and the other is a phenyl group, a biphenyl group, It is more preferably a pyridyl group or a naphthyl group (these groups may be substituted with a methyl group), and a group represented by ^{−Ar 2} −Ar ³ −Ar ^{4 or −Ar 5} −Ar. ^6- Ar ⁷ is one of the groups represented by phenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group. , Pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, phenanthryl group, dibenzothienyl group, or dibenzofuryl group (these groups) May be substituted with a methyl group), and the other is more preferably a phenyl group or a naphthyl group.

-Ar ² -Ar ³ -Ar ⁴ Group represented by, and -Ar ⁵ -Ar ⁶ -Ar ⁷ The specific example of the group represented by is not particularly limited, but is, for example, a phenyl group, a p-tolyl group, an m-tolyl group, an o-tolyl group, a 2,4-dimethylphenyl group, 3,5. -Dimethylphenyl group, mesityl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,4-diethylphenyl group, 3,5-diethylphenyl group, 2-propylphenyl group, 3- Propylphenyl group, 4-propylphenyl group, 2,4-dipropylphenyl group, 3,5-dipropylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2,4- Diisopropylphenyl group, 3,5-diisopropylphenyl group, 2-butylphenyl group, 3-butylphenyl group, 4-butylphenyl group, 2,4-dibutylphenyl group, 3,5-dibutylphenyl group, 2-tert- Butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2,4-di-tert-butylphenyl group, 3,5-di-tert-butylphenyl group, biphenyl-2-yl group , Biphenyl-3-yl group, biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl group, 4'-methylbiphenyl-4-yl group, 2,2 '-Dimethylbiphenyl-4-yl group, 2', 4', 6'-trimethylbiphenyl-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, 2', 4', 6'-trimethylbiphenyl-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 -Il group, 2', 4', 6'-trimethylbiphenyl-2-yl group, 3-ethylbiphenyl-4-yl group, 4'-ethylbiphenyl-4-yl group, 2', 4', 6' -Triethylbiphenyl-4-yl group, 6-ethylbiphenyl-3-yl group, 4'-ethylbiphenyl-3-yl group, 5-ethylbiphenyl-2-yl group, 4'-ethylbiphenyl-2-yl group , 2', 4', 6'-triethylbiphenyl-2-yl group, 3-propylbiphenyl-4-yl group, 4'-propylbiff Enyl-4-yl group, 2', 4', 6'-tripropylbiphenyl-4-yl group, 6-propylbiphenyl-3-yl group, 4'-propylbiphenyl-3-yl group, 5-propylbiphenyl -2-yl group, 4'-propylbiphenyl-2-yl group, 2', 4', 6'-tripropylbiphenyl-2-yl group, 3-isopropylbiphenyl-4-yl group, 4'-isopropylbiphenyl -4-yl group, 2', 4', 6'-triisopropylbiphenyl-4-yl group, 6-isopropylbiphenyl-3-yl group, 4'-isopropylbiphenyl-3-yl group, 5-isopropylbiphenyl- 2-Il group, 4'-isopropylbiphenyl-2-yl group, 2', 4', 6'-triisopropylbiphenyl-2-yl group, 3-butylbiphenyl-4-yl group, 4'-butylbiphenyl- 4-yl group, 2', 4', 6'-tributylbiphenyl-4-yl group, 6-butylbiphenyl-3-yl group, 4'-butylbiphenyl-3-yl group, 5-butylbiphenyl-2- Il group, 4'-butylbiphenyl-2-yl group, 2', 4', 6'-tributylbiphenyl-2-yl group, 3-tert-butylbiphenyl-4-yl group, 4'-tert-butylbiphenyl -4-yl group, 2', 4', 6'-tritert-butylbiphenyl-4-yl group, 6-tert-butylbiphenyl-3-yl group, 4'-tert-butylbiphenyl-3-yl group , 5-tert-butylbiphenyl-2-yl group, 4'-tert-butylbiphenyl-2-yl group, 2', 4', 6'-tritert-butylbiphenyl-2-yl group, 2-pyridyl group , 3-Pyridyl Group, 4-Pyridyl Group, 2-Methylpyridine-3-yl Group, 2-Methylpyridine-4-yl Group, 2-Methylpyridine-5-Il Group, 2-Methylpyridine-6-Il Group , 3-Methylpyridine-2-yl group, 3-methylpyridine-4-yl group, 3-methylpyridine-5-yl group, 3-methylpyridine-6-yl group, 4-methylpyridine-2-yl group , 4-Methylpyridine-3-yl group, 2,6-dimethylpyridine-3-yl group, 2,6-dimethylpyridine-4-yl group, 3,6-dimethylpyridine-2-yl group, 3,6 -Dimethylpyridine-4-yl group, 3,6-dimethylpyridine-5-yl group, 2-phenylpyridine-6-yl group, 3-phenylpyridine-6-yl group, 4-phenylpyridine-6-i Lu group, 5-phenylpyridine-6-yl group, 2-phenylpyridine-3-yl group, 2-phenylpyridine-5-yl group, 3-phenylpyridine-5-yl group, 4-phenylpyridine-3- Il group, 3-phenylpyridine-4-yl group, 2-phenylpyridine-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- (2,4-dimethyl-3-pyridyl) phenyl group, 3- (2,4-dimethyl-3-pyridyl) phenyl group, 4- (2,4-dimethyl) -3-Pyridyl) phenyl group, 2- (3,5-dimethyl-4-pyridyl) phenyl group, 3- (3,5-dimethyl-4-pyridyl) phenyl group, 4- (3,5-dimethyl-4) -Phenyl) phenyl group, 2- (3-phenyl-2-pyridyl) phenyl group, 3- (3-phenyl-2-pyridyl) phenyl group, 4- (3-Phenyl-2-pyridyl) phenyl group, 2- (4-phenyl-2-pyridyl) phenyl group, 3- (4-phenyl-2-pyridyl) phenyl group, 4- (4-phenyl-2) -Phenyl) phenyl group, 2- (5-phenyl-2-pyridyl) phenyl group, 3- (5-phenyl-2-pyridyl) phenyl group, 4- (5-phenyl-2-pyridyl) phenyl group, 2- (6-Phenyl-2-pyridyl) phenyl group, 3- (6-phenyl-2-pyridyl) phenyl group, 4- (6-phenyl-2-pyridyl) phenyl group, 2- (2-phenyl-2-pyridyl) ) Phenyl group, 3- (2-phenyl-3-pyridyl) phenyl group, 4- (2-phenyl-3-pyridyl) phenyl group, 2- (4-phenyl-3-pyridyl) phenyl group, 3- (4) -Phenyl-3-pyridyl) phenyl group, 4- (4-phenyl-3-pyridyl) phenyl group, 2- (5-phenyl-3-pyridyl) phenyl group, 3- (5-phenyl-3-pyridyl) phenyl Group, 4- (5-phenyl-3-pyridyl) phenyl group, 2- (6-phenyl-3-pyridyl) phenyl group, 3- (6-phenyl-3-pyridyl) phenyl group, 4- (6-phenyl) -3-Pyridyl) phenyl group, 2- (2-phenyl-4-pyridyl) phenyl group, 3- (2-phenyl-4-pyridyl) phenyl group, 4- (2-phenyl-4-pyridyl) phenyl group, 2- (3-Phenyl-4-pyridyl) phenyl group, 3- (3-phenyl-4-pyridyl) phenyl group, 4- (3-phenyl-4-pyridyl) phenyl group, 2- (2,4-diphenyl) -3-Pyridyl) Phenyl Group, 3- (2,4-Diphenyl-3-Pyridyl) Phenyl Group, 4- (2,4-Diphenyl-3-Pyridyl) Phenyl Group, 2- (3,5-Diphenyl-4) -Pyridyl) phenyl group, 3- (3,5-diphenyl-4-pyridyl) phenyl group, 4- (3,5-diphenyl-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- (1-phenanthril) phenyl group, 3- (1-phenanthril) phenyl group, 4- (1-phenanthril) phenyl group, 2- (2-phenanthril) phenyl group, 3- (2-Phenyl) phenyl group, 4- (2-Phenyl) phenyl group, 2- (3-Phenyl) phenyl group, 3- (3-Phenyl) phenyl group, 4- (3-Phenyl) phenyl group, 2- (4-Phenyl) phenyl group, 3- (4-Phenyl) phenyl group, 4- (4-Fenantril) phenyl group, 2- (9-Phenyl) phenyl group, 3- (9-Phenyl) phenyl group, 4- (9-Phenantril) 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- (4-Pyrenyl) Phenyl Group, 3- (4-Pyrenyl) Phenyl Group, 4- (4-Pyrenyl) Phenyl Group, 2- (Fluorenten-1-yl) Phenyl Group, 3- (Fluorenten-1-yl) phenyl group, 4- (Fluorenten-1-yl) phenyl group, 2- (Fluorenten-2-yl) phenyl group, 3- (Fluorenten-2-yl) phenyl group, 4- (Fluorenten-2-yl) Phenyl Group, 2- (Fluorenten-3-yl) Phenyl Group, 3- (Fluorenten-3-yl) Phenyl Group, 4- (Fluorenten-3-yl) Phenyl Group, 2- (Fluorenten-4-yl) Phenyl Group, 3- (Fluorenten-4-yl) Phenyl Group, 4- (Fluorenten-4-yl) Phenyl Group, 2- (Fluorenten-5-Il) Phenyl Group, 3- (Fluorenten) -5-yl) Phenyl group, 4- (Fluorenten-5-a) Le) Phenyl group, 2- (triphenylene-1-yl) phenyl group, 3- (triphenylene-1-yl) phenyl group, 4- (triphenylene-1-yl) phenyl group, 2- (triphenylene-2-yl) Phenyl group, 3- (triphenylene-2-yl) phenyl group, 4- (triphenylene-2-yl) phenyl group, 2- (crisen-1-yl) phenyl group, 3- (crisen-1-yl) phenyl group , 4- (Crycene-1-yl) phenyl group, 2- (Crycene-2-yl) phenyl group, 3- (Crycene-2-yl) phenyl group, 4- (Crycene-2-yl) phenyl group, 2 -(Crycene-3-yl) phenyl group, 3- (Crycene-3-yl) phenyl group, 4- (Crycene-3-yl) phenyl group, 2- (Crycene-4-yl) phenyl group, 3- ( Chrysen-4-yl) phenyl group, 4- (chrysen-4-yl) phenyl group, 2- (chrysen-5-yl) phenyl group, 3- (chrysen-5-yl) phenyl group, 4- (chrysen-) 5-Il) Phenyl Group, 2- (Crycene-6-Il) Phenyl Group, 3- (Crycene-6-Il) Phenyl Group, 4- (Crycene-6-Il) Phenyl Group, 2- (Acenaphthylene-1-) Ill) Phenyl Group, 3- (Acenaphthylene-1-yl) Phenyl Group, 4- (Asenafutilen-1-yl) Phenyl Group, 2- (Asenafutilen-3-yl) Phenyl Group, 3- (Asenafutilen-3-yl) Phenyl group, 4- (acenaphtylene-3-yl) phenyl group, 2- (acenaphtylene-4-yl) phenyl group, 3- (acenaphtylene-4-yl) phenyl group, 4- (acenaphtylene-4-yl) phenyl group , 2- (Acenaphthylene-5-yl) phenyl group, 3- (Acenaphthylene-5-yl) phenyl group, 4- (Asenafutilene-5-yl) phenyl group,
2- (Fluoren-1-yl) Phenyl Group, 3- (Fluoren-1-yl) Phenyl Group, 4- (Fluoren-1-yl) Phenyl Group, 2- (Fluoren-2-yl) Phenyl Group, 3- (Fluoren-2-yl) Phenyl Group, 4- (Fluoren-2-yl) Phenyl Group, 2- (Fluoren-3-yl) Phenyl Group, 3- (Fluoren-3-yl) Phenyl Group, 4- (Fluoren-2-yl) -3-yl) phenyl group, 2- (fluoren-4-yl) phenyl group, 3- (fluoren-4-yl) phenyl group, 4- (fluoren-4-yl) phenyl group, 2- (pyrimidine-2) -Il) Phenyl group, 3- (Pyrimidine-2-yl) phenyl group, 4- (Pyrimidine-2-yl) phenyl group, 2- (Pyrimidine-4-yl) phenyl group, 3- (Pyrimidine-4-yl) ) Phenyl group, 4- (pyrimidine-4-yl) phenyl group, 2- (pyrimidine-5-yl) phenyl group, 3- (pyrimidine-5-yl) phenyl group, 4- (pyrimidine-5-yl) phenyl Group, 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- (2-isoquinolyl) phenyl group, 3- (2-isoquinolyl) phenyl group, 4- (2-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-isoquinoli) Le) 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, 2- (phenanthridin-2-yl) phenyl group, 3- (phenanthridin-2-yl) Phenyl group, 4- (phenanthridin-2-yl) phenyl group, 2- (phenanthridin-3-yl) phenyl group, 3- (phenanthridin-3-yl) phenyl group, 4- (phenant) Phenyl-3-yl) phenyl group, 2- (phenanthridin-4-yl) phenyl group, 3- (phenanthridin-4-yl) phenyl group, 4- (phenanthridin-4-yl) phenyl group , 2- (Phenyltridin-5-yl) phenyl group, 3- (Phenantridin-5-yl) phenyl group, 4- (Phenyltridin-5-yl) phenyl group, 2- (Phenantridin-) 6-yl) phenyl group, 3- (phenanthridin-6-yl) phenyl group, 4- (phenanthridin-6-yl) phenyl group, 2- (phenanthridin-7-yl) phenyl group, 3 -(Phenyltridin-7-yl) phenyl group, 4- (phenanthridin-7-yl) phenyl group, 2- (phenanthridin-8-yl) phenyl group, 3- (phenanthridin-8-) Ill) Phenyl Group, 4- (Phenyltridin-8-Il) Phenyl Group, 2- (Phenantridin-9-Il) Phenyl Group, 3- (Phenantridin-9-Il) Phenyl Group, 4- ( Phenyltridin-9-yl) Phenyl group, 2- (Phenantridin-10-yl) phenyl group, 3- (Phenantridin-10-yl) phenyl group, 4- (Phenantridin-10-yl) Phenyl group,
2- (Benzo [h] quinoline-2-yl) phenyl group, 3- (benzo [h] quinoline-2-yl) phenyl group, 4- (benzo [h] quinoline-2-yl) phenyl group, 2- (Benzo [h] quinoline-3-yl) phenyl group, 3- (benzo [h] quinoline-3-yl) phenyl group, 4- (benzo [h] quinoline-3-yl) phenyl group, 2- (benzo [H] Quinoline-4-yl) phenyl group, 3- (benzo [h] quinoline-4-yl) phenyl group, 4- (benzo [h] quinoline-4-yl) phenyl group, 2- (benzo [h] benzo [h] ] Quinoline-5-yl) phenyl group, 3- (benzo [h] quinoline-5-yl) phenyl group, 4- (benzo [h] quinoline-5-yl) phenyl group, 2- (benzo [h] quinoline -6-yl) phenyl group, 3- (benzo [h] quinoline-6-yl) phenyl group, 4- (benzo [h] quinoline-6-yl) phenyl group, 2- (benzo [h] quinoline-7 -Il) phenyl group, 3- (benzo [h] quinoline-7-yl) phenyl group, 4- (benzo [h] quinoline-7-yl) phenyl group, 2- (benzo [h] quinoline-8-yl) ) Phenyl group, 3- (benzo [h] quinoline-8-yl) phenyl group, 4- (benzo [h] quinoline-8-yl) phenyl group, 2- (benzo [h] quinoline-9-yl) phenyl Group, 3- (benzo [h] quinoline-9-yl) phenyl group, 4- (benzo [h] quinoline-9-yl) phenyl group, 2- (benzo [h] quinoline-10-yl) phenyl group, 3- (Benzo [h] quinoline-10-yl) phenyl group, 4- (benzo [h] quinoline-10-yl) phenyl group, 2- (acrindin-1-yl) phenyl group, 3- (acrindin-1) -Il) phenyl group, 4- (aclydin-1-yl) phenyl group, 2- (aclydin-2-yl) phenyl group, 3- (aclydin-2-yl) phenyl group, 4- (acridin-2-yl) ) Phenyl group, 2- (aclydin-3-yl) phenyl group, 3- (aclydin-3-yl) phenyl group, 4- (aclydin-3-yl) phenyl group, 2- (aclysin-4-yl) phenyl Group, 3- (aclydin-4-yl) phenyl group, 4- (aclydin-4-yl) phenyl group, 2- (aclydin-9-yl) phenyl group, 3- (aclysin-9-yl) phenyl group, 4- (acrindin-9-yl) phenyl group, 2- (2-thienyl) phenyl group, 3- (2-chi) Enyl) phenyl group, 4- (2-thienyl) phenyl group, 2- (3-thienyl) phenyl group, 3- (3-thienyl) phenyl group, 4- (3-thienyl) phenyl group, 2- (3-) Methylthiophen-2-yl) phenyl group, 3- (3-methylthiophen-2-yl) phenyl group, 4- (3-methylthiophen-2-yl) phenyl group, 2- (4-methylthiophen-2-yl) Phenyl group, 3- (4-methylthiophen-2-yl) phenyl group, 4- (4-methylthiophen-2-yl) phenyl group, 2- (5-methylthiophen-2-yl) phenyl group, 3- (5-Methylthiophen-2-yl) phenyl group, 4- (5-methylthiophen-2-yl) phenyl group, 2- (2-methylthiophen-3-yl) phenyl group, 3- (2-) Methylthiophene-3-yl) phenyl group, 4- (2-methylthiophen-3-yl) phenyl group, 2- (4-methylthiophen-3-yl) phenyl group, 3- (4-methylthiophen-3-yl) Phenyl group, 4- (4-methylthiophen-3-yl) phenyl group, 2- (5-methylthiophen-3-yl) phenyl group, 3- (5-methylthiophen-3-yl) phenyl group, 4- (5-Methylthiophen-3-yl) phenyl group, 2- (3-phenylthiophen-2-yl) phenyl group, 3- (3-phenylthiophen-2-yl) phenyl group, 4- (3- (3-) Phenylthiophen-2-yl) Phenyl group, 2- (4-phenylthiophen-2-yl) phenyl group, 3- (4-phenylthiophen-2-yl) phenyl group, 4- (4-phenylthiophen-2-yl) Phenyl group, 2- (5-phenylthiophen-2-yl) phenyl group, 3- (5-phenylthiophen-2-yl) phenyl group, 4- (5-phenylthiophen-2-yl) phenyl group, 2- (2-Phenylthiophen-3-yl) phenyl group, 3- (2-phenylthiophen-3-yl) phenyl group, 4- (2-phenylthiophen-3-yl) phenyl group, 2- (4- (4-yl) Phenylthiophene-3-yl) Phenyl group, 3- (4-phenylthiophen-3-yl) phenyl group, 4- (4-phenylthiophen-3-yl) phenyl group, 2- (5-phenylthiophen-3-yl) Phenyl group, 3- (5-phenylthiophen-3-yl) phenyl group, 4- (5-phenylthiophen-3-yl) phenyl group,
3- (2-Frill) Phenyl Group, 4- (2-Frill) Phenyl Group, 2- (3-Frill) Phenyl Group, 3- (3-Frill) Phenyl Group, 4- (3-Frill) Phenyl Group, 2- (3-Methylfuran-2-yl) phenyl group, 3- (3-methylfuran-2-yl) phenyl group, 4- (3-methylfuran-2-yl) phenyl group, 2- (4-) Methylfuran-2-yl) phenyl group, 3- (4-methylfuran-2-yl) phenyl group, 4- (4-methylfuran-2-yl) phenyl group, 2- (5-methylfuran-2-yl) Phenyl group, 3- (5-methylfuran-2-yl) phenyl group, 4- (5-methylfuran-2-yl) phenyl group, 2- (2-methylfuran-2-yl) phenyl group, 3- (2-Methylfuran-3-yl) phenyl group, 4- (2-methylfuran-3-yl) phenyl group, 2- (4-methylfuran-3-yl) phenyl group, 3- (4- (4-yl) Methylfuran-3-yl) phenyl group, 4- (4-methylfuran-3-yl) phenyl group, 2- (5-methylfuran-3-yl) phenyl group, 3- (5-methylfuran-3-yl) Phenyl group, 4- (5-methylfuran-3-yl) phenyl group, 2- (3-phenylfuran-2-yl) phenyl group, 3- (3-phenylfuran-2-yl) phenyl group, 4- (3-Phenylfuran-2-yl) phenyl group, 2- (4-phenylfuran-2-yl) phenyl group, 3- (4-phenylfuran-2-yl) phenyl group, 4- (4- (4-) Phenylfuran-2-yl) phenyl group, 2- (5-phenylfuran-2-yl) phenyl group, 3- (5-phenylfuran-2-yl) phenyl group, 4- (5-phenylfuran-2-yl) Phenyl group, 2- (2-phenylfuran-3-yl) phenyl group, 3- (2-phenylfuran-3-yl) phenyl group, 4- (2-phenylfuran-3-yl) phenyl group, 2- (4-Phenylfuran-3-yl) phenyl group, 3- (4-phenylfuran-3-yl) phenyl group, 4- (4-phenylfuran-3-yl) phenyl group, 2- (5-) Phenylfuran-3-yl) phenyl group, 3- (5-phenylfuran-3-yl) phenyl group, 4- (5-phenylfuran-3-yl) phenyl group, 2- (2-benzo [b] thienyl ) Phenyl group, 3- (2-benzo [b] thienyl) phenyl group, 4- (2-benzo [b] thienyl) phenyl group, 2- (3-benzo [b] thie Nyl) phenyl group, 3- (3-benzo [b] thienyl) phenyl group, 4- (3-benzo [b] thienyl) phenyl group, 2- (4-benzo [b] thienyl) phenyl group, 3- ( 4-Benzo [b] thienyl) phenyl group, 4- (4-benzo [b] thienyl) phenyl group, 2- (5-benzo [b] thienyl) phenyl group, 3- (5-benzo [b] thienyl) Phenyl group, 4- (5-benzo [b] thienyl) phenyl group, 2- (6-benzo [b] thienyl) phenyl group, 3- (6-benzo [b] thienyl) phenyl group, 4- (6- (6-) Benzo [b] thienyl) phenyl group, 2- (7-benzo [b] thienyl) phenyl group, 3- (7-benzo [b] thienyl) phenyl group, 4- (7-benzo [b] thienyl) phenyl group , 2- (2-benzo [b] frill) phenyl group, 3- (2-benzo [b] frill) phenyl group, 4- (2-benzo [b] frill) phenyl group, 2- (3-benzo [b] frill) b] Frill) phenyl group, 3- (3-benzo [b] frill) phenyl group, 4- (3-benzo [b] frill) phenyl group, 2- (4-benzo [b] frill) phenyl group, 3 -(4-Benzo [b] frill) phenyl group, 4- (4-benzo [b] frill) phenyl group, 2- (5-benzo [b] frill) phenyl group, 3- (5-benzo [b] Frill) phenyl group, 4- (5-benzo [b] frill) phenyl group, 2- (6-benzo [b] frill) phenyl group, 3- (6-benzo [b] frill) phenyl group, 4- ( 6-Benzo [b] frill) phenyl group, 2- (7-benzo [b] frill) phenyl group, 3- (7-benzo [b] frill) phenyl group, 4- (7-benzo [b] frill) Phenyl group, 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-diben) Zofryl) 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,
3- (2-pyridyl) biphenyl-4-yl group, 2'-(2-pyridyl) biphenyl-4-yl group, 4'-(2-pyridyl) biphenyl-4-yl group, 2,2'-di (2-Pyridyl) biphenyl-4-yl group, 2', 4', 6'-tri (2-pyridyl) biphenyl-4-yl group, 6- (2-pyridyl) biphenyl-3-yl group, 5- (2-Pyridyl) biphenyl-3-yl group, 2'-(2-pyridyl) biphenyl-3-yl group, 4'-(2-pyridyl) biphenyl-3-yl group, 6,2'-di (2'-di (2) -Pyridyl) biphenyl-3-yl group, 5- (2-pyridyl) biphenyl-2-yl group, 6- (2-pyridyl) biphenyl-2-yl group, 2'-(2-pyridyl) biphenyl-2- Il group, 4'-(2-pyridyl) biphenyl-2-yl group, 6,2'-di (2-pyridyl) biphenyl-2-yl group, 3- (3-pyridyl) biphenyl-4-yl group, 2'-(3-pyridyl) biphenyl-4-yl group, 4'-(3-pyridyl) biphenyl-4-yl group, 2,2'-di (3-pyridyl) biphenyl-4-yl group, 2' , 4', 6'-tri (3-pyridyl) biphenyl-4-yl group, 6- (3-pyridyl) biphenyl-3-yl group, 5- (3-pyridyl) biphenyl-3-yl group, 2' -(3-Pyridyl) biphenyl-3-yl group, 4'-(3-pyridyl) biphenyl-3-yl group, 6,2'-di (3-pyridyl) biphenyl-3-yl group, 5- (3) -Pyridyl) biphenyl-2-yl group, 6- (3-pyridyl) biphenyl-2-yl group, 2'-(3-pyridyl) biphenyl-2-yl group, 4'-(3-pyridyl) biphenyl-2 -Il group, 6,2'-di (3-pyridyl) biphenyl-2-yl group, 3- (4-pyridyl) biphenyl-4-yl group, 2'-(4-pyridyl) biphenyl-4-yl group 4,'-(4-pyridyl) biphenyl-4-yl group, 2,2'-di (4-pyridyl) biphenyl-4-yl group, 2', 4', 6'-tri (4-pyridyl) biphenyl -4-yl group, 6- (4-pyridyl) biphenyl-3-yl group, 5- (4-pyridyl) biphenyl-3-yl group, 2'-(4-pyridyl) biphenyl-3-yl group, 4 '-(4-Pyridyl) biphenyl-3-yl group, 6,2'-di (4-pyridyl) biphenyl-3-yl group, 5- (4-pyridyl) biphenyl-2-yl group, 6- (4) -Pyridyl) biphenyl-2-yl group, 2 '-(4-Pyridyl) biphenyl-2-yl group, 4'-(4-pyridyl) biphenyl-2-yl group, 6,2'-di (4-pyridyl) biphenyl-2-yl group, 3- ( 1-naphthyl) biphenyl-4-yl group, 2'-(1-naphthyl) biphenyl-4-yl group, 4'-(1-naphthyl) biphenyl-4-yl group, 2,2'-di (1-) Naftyl) biphenyl-4-yl group, 2', 4', 6'-tri (1-naphthyl) biphenyl-4-yl group, 6- (1-naphthyl) biphenyl-3-yl group, 5- (1-) Naftyl) Biphenyl-3-yl group, 2'-(1-naphthyl) biphenyl-3-yl group, 4'-(1-naphthyl) biphenyl-3-yl group, 6,2'-di (1-naphthyl) Biphenyl-3-yl group, 5- (1-naphthyl) biphenyl-2-yl group, 6- (1-naphthyl) biphenyl-2-yl group, 2'-(1-naphthyl) biphenyl-2-yl group, 4'-(1-naphthyl) biphenyl-2-yl group, 6,2'-di (1-naphthyl) biphenyl-2-yl group, 3- (2-naphthyl) biphenyl-4-yl group, 2'- (2-naphthyl) biphenyl-4-yl group, 4'-(2-naphthyl) biphenyl-4-yl group, 2,2'-di (2-naphthyl) biphenyl-4-yl group, 2', 4' , 6'-tri (2-naphthyl) biphenyl-4-yl group, 6- (2-naphthyl) biphenyl-3-yl group, 5- (2-naphthyl) biphenyl-3-yl group, 2'-(2'-(2) -Naphthyl) biphenyl-3-yl group, 4'-(2-naphthyl) biphenyl-3-yl group, 6,2'-di (2-naphthyl) biphenyl-3-yl group, 5- (2-naphthyl) Biphenyl-2-yl group, 6- (2-naphthyl) biphenyl-2-yl group, 2'-(2-naphthyl) biphenyl-2-yl group, 4'-(2-naphthyl) biphenyl-2-yl group , 6,2'-di (2-naphthyl) biphenyl-2-yl group,
1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalene-2-yl group, 1-phenylnaphthalene-3-yl group, 1-phenylnaphthalene-4-yl group, 1-phenylnaphthalene-5-yl group, 1-Phenanthrene-6-yl group, 1-Phenanthrene-7-yl group, 1-Phenanthrene-8-yl group, 2-Phenanthrene-1-yl group, 2-Phenanthrene-3-yl group, 2-Phenanthrene-4-yl group, 2-Phenanthrene-5-yl group, 2-Phenanthrene-6-yl group, 2-Phenanthrene-7-yl group, 2-Phenanthrene-8-yl group, 1-Methylnaphthrene-4-yl group, 1-methylnaphthrene-5-yl group, 1-methylnaphthrene-6-yl group, 1-methylnaphthrene-7-yl group, 1-methylnaphthrene-8-yl group, 2-Methylnaphthrene-1-yl group, 2-methylnaphthrene-3-yl group, 2-methylnaphthrene-4-yl group, 2-methylnaphthrene-5-yl group, 2-methylnaphthrene-6-yl group, 2-Methylnaphthrene-7-yl group, 2-methylnaphthrene-8-yl group, 1-phenanthrene group, 2-phenanthrene group, 3-phenanthrene group, 4-phenanthrene group, 9-phenanthrene group, 1-phenylphenanthrene- 2-yl group, 1-phenylphenanthrene-3-yl group, 1-phenylphenanthrene-4-yl group, 1-phenylphenanthrene-5-yl group, 1-phenylphenanthrene-6-yl group, 1-phenylphenanthrene- 7-yl group, 1-phenylphenanthrene-8-yl group, 1-phenylphenanthrene-9-yl group, 1-phenylphenanthrene-10-yl group, 2-phenylphenanthrene-1-yl group, 2-phenylphenanthrene- 3-yl group, 2-phenylphenanthrene-4-yl group, 2-phenylphenanthrene-5-yl group, 2-phenylphenanthrene-6-yl group, 2-phenylphenanthrene-7-yl group, 2-phenylphenanthrene- 8-yl group, 2-phenylphenanthrene-9-yl group, 2-phenylphenanthrene-10-yl group, 3-phenylphenanthrene-1-yl group, 3-phenylphenanthrene-2-yl group, 3-phenylphenanthrene- 4-yl group, 3-phenylphenanthrene-5-yl group, 3-phenylphenanthrene-6-yl group, 3-phenylphenanth Ren-7-yl group, 3-phenylphenanthrene-8-yl group, 3-phenylphenanthrene-9-yl group, 3-phenylphenanthrene-10-yl group, 4-phenylphenanthrene-1-yl group, 4-phenyl Phenanthrene-2-yl group, 4-phenylphenanthrene-3-yl group, 4-phenylphenanthrene-5-yl group, 4-phenylphenanthrene-6-yl group, 4-phenylphenanthrene-7-yl group, 4-phenyl Phenanthrene-8-yl group, 4-phenylphenanthrene-9-yl group, 4-phenylphenanthrene-10-yl group, 1-methylphenanthrene-2-yl group, 1-methylphenanthrene-3-yl group, 1-methyl Phenanthrene-4-yl group, 1-methylphenanthrene-5-yl group, 1-methylphenanthrene-6-yl group, 1-methylphenanthrene-7-yl group, 1-methylphenanthrene-8-yl group, 1-methyl Phenanthrene-9-yl group, 1-methylphenanthrene-10-yl group, 2-methylphenanthrene-1-yl group, 2-methylphenanthrene-3-yl group, 2-methylphenanthrene-4-yl group, 2-methyl Phenanthrene-5-yl group, 2-methylphenanthrene-6-yl group, 2-methylphenanthrene-7-yl group, 2-methylphenanthrene-8-yl group, 2-methylphenanthrene-9-yl group, 2-methyl Phenanthrene-10-yl group, 3-methylphenanthrene-1-yl group, 3-methylphenanthrene-2-yl group, 3-methylphenanthrene-4-yl group, 3-methylphenanthrene-5-yl group, 3-methyl Phenanthrene-6-yl group, 3-methylphenanthrene-7-yl group, 3-methylphenanthrene-8-yl group, 3-methylphenanthrene-9-yl group, 3-methylphenanthrene-10-yl group, 4-methyl Phenanthrene-1-yl group, 4-methylphenanthrene-2-yl group, 4-methylphenanthrene-3-yl group, 4-methylphenanthrene-5-yl group, 4-methylphenanthrene-6-yl group, 4-methyl Phenanthrene-7-yl group, 4-methylphenanthrene-8-yl group, 4-methylphenanthrene-9-yl group, 4-methylphenanthrene-10-yl group,
1-Anthryl group, 2-Anthryl group, 9-Anthryl group, 1-Phenylanthracen-2-yl group, 1-Phenylanthracen-3-yl group, 1-Phenylanthracene-4-yl group, 1-Phenylanthracene- 5-Il Group, 1-Phenylanthracen-6-Il Group, 1-Phenylanthracen-7-Il Group, 1-Phenylanthracen-8-Il Group, 1-Phenylanthracen-9-Il Group, 1-Phenylanthracen- 10-Il group, 2-Phenylanthracene-1-yl group, 2-Phenylanthracen-3-yl group, 2-Phenylanthracen-4-yl group, 2-Phenylanthracen-5-yl group, 2-Phenylanthracen- 6-Il Group, 2-Phenylanthracen-7-Il Group, 2-Phenylanthracen-8-Il Group, 2-Phenylanthracen-9-Il Group, 2-Phenylanthracen-10-Il Group, 9-Phenylanthracen- 1-yl group, 9-phenylanthracene-2-yl group, 9-phenylanthracene-3-yl group, 9-phenylanthracene-4-yl group, 9-phenylanthracene-5-yl group, 1-pyrenyl group, 2-Pyrenyl group, 4-Pyrenyl group, 1-Phenylpyrene-2-yl group, 1-Phenylpyrene-3-yl group, 1-Phenylpyrene-4-yl group, 1-Phenylpyrene-5-yl group, 1-Phenylpyrene-6-yl group, 1-Phenylpyrene-7-yl group, 1-Phenylpyrene-8-yl group, 1-Phenylpyrene-9-yl group, 1-Phenylpyrene-10-yl group, 2-Phenylpyrene-1-yl group, 2-Phenylpyrene-3-yl group, 2-Phenylpyrene-4-yl group, 2-Phenylpyrene-5-yl group, 2-Phenylpyrene-6-yl group, 2-Phenylpyrene-7-yl group, 2-Phenylpyrene-8-yl group, 2-Phenylpyrene-9-yl group, 2-Phenylpyrene-10-yl group, 9-Phenylpyrene-1-yl group, 9-Phenylpyrene-2-yl group, 9-Phenylpyrene-3-yl group, 9-Phenylpyrene-4-yl group, 9-Phenylpyrene-5-yl group, 9-Phenylpyrene-6-yl group, 9-Phenylpyrene-7-yl group, 9-Phenylpyrene-8-yl group, 9-Phenylpyrene-10-yl group, 1-methylpyrene-2-yl group, 1-methylpyrene-3-yl group, 1- Methylpyrene-4-yl group, 1-methylpyrene-5-yl group, 1-methylpyrene-6-yl group, 1-Methylpyrene-7-yl group, 1-methylpyrene-8-yl group, 1-methylpyrene-9-yl group, 1-methylpyrene-10-yl group, 2-methylpyrene-1-yl group, 2-methylpyrene-3 -Il group, 2-methylpyrene-4-yl group, 2-methylpyrene-5-yl group, 2-methylpyrene-6-yl group, 2-methylpyrene-7-yl group, 2-methylpyrene-8-yl group, 2 -Methylpyrene-9-yl group, 2-methylpyrene-10-yl group, 9-methylpyrene-1-yl group, 9-methylpyrene-2-yl group, 9-methylpyrene-3-yl group, 9-methylpyrene-4- Il group, 9-methylpyrene-5-yl group, 9-methylpyrene-6-yl group, 9-methylpyrene-7-yl group, 9-methylpyrene-8-yl group, 9-methylpyrene-10-yl group, fluoranthene- 1-yl group, fluoranthene-1-yl group, fluoranthene-2-yl group, fluoranthene-3-yl group, fluoranthene-4-yl group, fluoranthene-5-yl group, fluoranthene-6-yl group, fluoranthene-7 -Il group, fluoranthene-8-yl group, fluoranthene-9-yl group, fluoranthene-10-yl group, triphenylene-1-yl group, triphenylene-2-yl group, acenaphtylene-1-yl group, acenaphtylene-3-3 Il group, acetylene-4-yl group, acetylene-5-yl group, chrysen-1-yl group, chrysen-2-yl group, chrysen-5-yl group, chrysen-6-yl group, 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, quinazoline-2-yl group, quinazoline-4-yl group, Fluoranthene-5-yl group, quinazoline-6-yl group, quinazoline-7-yl group, quinazoline-8-yl group, fluoranthene-2-yl group, fluoranthene-2-yl group, pyrimidine-4-yl group, pyrimidine -5-Il group, Fluorin-1-yl group, Acrydin-1-yl group, Acrydin-2-yl group, Acrydin-3-yl group, Acrydin-4-yl group, Acrydin-9-yl group,
Phenantridin-1-yl group, phenanthridin-1-yl group, phenanthridin-2-yl group, phenanthridin-3-yl group, phenanthridin-4-yl group, phenanthridin-6 -Il group, phenanthridin-7-yl group, phenanthridin-8-yl group, phenanthridin-9-yl group, phenanthridin-10-yl group, phenazine-1-yl group, phenazine-2 -Il group, benzo [h] quinoline-2-yl group, benzo [h] quinoline-3-yl group, benzo [h] quinoline-4-yl group, benzo [h] quinoline-5-yl group, benzo [ h] quinoline-6-yl group, benzo [h] quinoline-7-yl group, benzo [h] quinoline-8-yl group, benzo [h] quinoline-9-yl group, benzo [h] quinoline-10- Il group, 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-Il group, Benzothiophen-7-Il group, Dibenzothiophen-1-yl group, Dibenzothiophen-2-yl group, Dibenzothiophen-3-yl group, Dibenzofuran-1-yl group, Dibenzofuran-2-yl group , Dibenzofuran-3-yl group, 3-methylthiophen-2-yl group, 4-methylthiophen-2-yl group, 5-methylthiophen-2-yl group, 2-methylthiophen-3-yl group, 4- Methylthiophene-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, 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-methylbenzothiophene- 3-yl group, 5-methylbenzothiophen-3-yl group, 6-methylbenzothiophen-3-yl group, 7-methylbenzothiophene En-3-yl group, 2-methylbenzothiophen-4-yl group, 3-methylbenzothiophen-4-yl group, 5-methylbenzothiophen-4-yl group, 6-methylbenzothiophen-4-yl group Group, 7-Methylbenzothiophen-4-yl group, 2-methylbenzothiophen-5-yl group, 3-methylbenzothiophen-5-yl group, 4-methylbenzothiophen-5-yl group, 6-methylbenzo Thiophen-5-yl group, 7-methylbenzothiophen-5-yl group, 2-methylbenzothiophen-6-yl group, 3-methylbenzothiophen-6-yl group, 4-methylbenzothiophen-6-yl group , 5-Methylbenzothiophene-6-yl group, 7-methylbenzothiophen-6-yl group, 2-methylbenzothiophen-7-yl group, 3-methylbenzothiophen-7-yl group, 4-methylbenzothiophene -7-Il group, 5-Methylbenzothiophene-7-Il group, 6-Methylbenzothiophene-7-Il group, 3-Methylbenzothiophene-2-yl group, 4-Methylbenzothiophene-2-yl group, 5-Il group 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-yl Methylbenzofuran-7-yl group, 5-methylbenzothiophen-7-yl group, 6-methylbenzothiophen-7-yl group, 2-methyldibenzothiophen-1-yl group, 3-methyldibenzothiophen-1-yl group, 4-Methyldibenzo Thiophen-1-yl group, 6-methyldibenzothiophene-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-methyldibenzothiophene -2-yl group, 8-methyldibenzothiophen-2-yl group, 9-methyldibenzothiophen-2-yl group, 1-methyldibenzothiophen-3-yl group, 2-methyldibenzothiophen-3-yl group, 4-Methyldibenzothiophene-3-yl group, 6-methyldibenzothiophene-3-yl group, 7-methyldibenzothiophene-3-yl group, 8-methyldibenzothiophene-3-yl group, 9-methyldibenzothiophene- 3-Il group, 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-Il 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, 3-phenylthiophen-2-yl group, 4-phenylthiophen-2-yl group, 5-phenylthiophen-2-yl group, 2-phenylthiophene- 3-Il group, 4-phenylthiophene-3-yl group, 5-phenylthiophene-3-yl group, 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, 3-phenylbe Nzothiophen-2-yl group, 4-phenylbenzothiophen-2-yl group, 5-phenylbenzothiophen-2-yl group, 6-phenylbenzothiophen-2-yl group, 7-phenylbenzothiophen-2-yl group , 2-Phenylbenzothiophene-3-yl group, 4-phenylbenzothiophene-3-yl group, 5-phenylbenzothiophene-3-yl group, 6-phenylbenzothiophene-3-yl group, 7-phenylbenzothiophene -3-yl group, 2-phenylbenzothiophene-4-yl group, 3-phenylbenzothiophene-4-yl group, 5-phenylbenzothiophene-4-yl group, 6-phenylbenzothiophene-4-yl group, 7-Phenylbenzothiophene-4-yl group, 2-phenylbenzothiophene-5-yl group, 3-phenylbenzothiophene-5-yl group, 4-phenylbenzothiophene-5-yl group, 6-phenylbenzothiophene- 5-yl group, 7-phenylbenzothiophene-5-yl group, 2-phenylbenzothiophen-6-yl group, 3-phenylbenzothiophen-6-yl group, 4-phenylbenzothiophen-6-yl group, 5 -Phenylbenzothiophene-6-yl group, 7-phenylbenzothiophene-6-yl group, 2-phenylbenzothiophene-7-yl group, 3-phenylbenzothiophene-7-yl group, 4-phenylbenzothiophen-7 -Il group, 5-phenylbenzothiophene-7-yl group, 6-phenylbenzothiophene-7-yl group, 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-a Lu group, 2-phenylbenzofuran-6-yl group, 3-phenylbenzofuran-6-yl group, 4-phenylbenzofuran-6-yl group, 5-phenylbenzofuran-6-yl group, 7-phenylbenzofuran-6- Il group, 2-phenylbenzofuran-7-yl group, 3-phenylbenzofuran-7-yl group, 4-phenylbenzofuran-7-yl group, 5-phenylbenzofuran-7-yl group, 6-phenylbenzofuran-7- Il group, 2-phenyldibenzothiophene-1-yl group, 3-phenyldibenzothiophen-1-yl group, 4-phenyldibenzothiophen-1-yl group, 6-phenyldibenzothiophen-1-yl group, 7-phenyl Dibenzothiophene-1-yl group, 8-phenyldibenzothiophen-1-yl group, 9-phenyldibenzothiophen-1-yl group, 1-phenyldibenzothiophen-2-yl group, 3-phenyldibenzothiophen-2-yl group Group, 4-phenyldibenzothiophen-2-yl group, 6-phenyldibenzothiophen-2-yl group, 7-phenyldibenzothiophen-2-yl group, 8-phenyldibenzothiophen-2-yl group, 9-phenyldibenzo Thiophen-2-yl group, 1-phenyldibenzothiophen-3-yl group, 2-phenyldibenzothiophen-3-yl group, 4-phenyldibenzothiophen-3-yl group, 6-phenyldibenzothiophen-3-yl group , 7-Phenyldibenzothiophen-3-yl group, 8-phenyldibenzothiophen-3-yl group, 9-phenyldibenzothiophen-3-yl group,
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, 3- (2-pyridyl) thiophen-2-yl group, 4- (2-pyridyl) thiophen-2-yl group, 5- (2-pyridyl) thiophen-2-yl group 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) ) Phenyl-2-yl group, 4- (2-pyridyl) furan-2-yl group, 5- (2-pyridyl) furan-2-yl group, 2- (2-pyridyl) furan-3-yl group, 4- (2-pyridyl) furan-3-yl group, 5- (2-pyridyl) furan-3-yl group, 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 Il 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) benzothiophen-3-yl group, 2- (2-pyridyl) benzothiophen-4-yl group, 3- (2-pyridyl) Phenyl-4-yl group, 5- (2-pyridyl) benzothiophen-4-yl group, 6- ( 2-Pyridyl) benzothiophene-4-yl group, 7- (2-pyridyl) benzothiophene-4-yl group, 2- (2-pyridyl) benzothiophene-5-yl group, 3- (2-pyridyl) benzo Thiophen-5-yl group, 4- (2-pyridyl) benzothiophene-5-yl group, 6- (2-pyridyl) benzothiophene-5-yl group, 7- (2-pyridyl) benzothiophen-5-yl group Group, 2- (2-pyridyl) benzothiophene-6-yl group, 3- (2-pyridyl) benzothiophene-6-yl group, 4- (2-pyridyl) benzothiophene-6-yl group, 5-( 2-pyridyl) benzothiophene-6-yl group, 7- (2-pyridyl) benzothiophene-6-yl group, 2- (2-pyridyl) benzothiophene-7-yl group, 3- (2-pyridyl) benzo Thiophen-7-yl group, 4- (2-pyridyl) benzothiophene-7-yl group, 5- (2-pyridyl) benzothiophene-7-yl group, 6- (2-pyridyl) benzothiophen-7-yl group Group, 3- (2-pyridyl) benzofuran-2-yl group, 4- (2-pyridyl) benzofuran-2-yl group, 5- (2-pyridyl) benzofuran-2-yl group, 6- (2-pyridyl) ) Benzofuran-2-yl group, 7- (2-pyridyl) benzofuran-2-yl group, 2- (2-pyridyl) benzofuran-3-yl group, 4- (2-pyridyl) benzofuran-3-yl group, 5- (2-pyridyl) benzofuran-3-yl group, 6- (2-pyridyl) benzofuran-3-yl group, 7- (2-pyridyl) benzofuran-3-yl group, 2- (2-pyridyl) benzofuran -4-yl group, 3- (2-pyridyl) benzofuran-4-yl group, 5- (2-pyridyl) benzofuran-4-yl group, 6- (2-pyridyl) benzofuran-4-yl group, 7- (2-Pyridyl) benzofuran-4-yl group, 2- (2-pyridyl) benzofuran-5-yl group, 3- (2-pyridyl) benzofuran-5-yl group, 4- (2-pyridyl) benzofuran-5 -Il 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 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- Il group, 6- (2-pyridyl) benzofuran-7-yl group, 2- (2-pyridyl) dibenzothiophene-1-yl group, 3- (2-pyridyl) dibenzothiophene-1-yl group, 4- ( 2-Pyridyl) dibenzothiophene-1-yl group, 6- (2-pyridyl) dibenzothiophene-1-yl group, 7- (2-pyridyl) dibenzothiophene-1-yl group, 8- (2-pyridyl) dibenzo Thiophen-1-yl group, 9- (2-pyridyl) dibenzothiophene-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) dibenzothiophene-3-yl group, 2- (2-pyridyl) dibenzo Thiophen-3-yl group, 4- (2-pyridyl) dibenzothiophene-3-yl group, 6- (2-pyridyl) dibenzothiophene-3-yl group, 7- (2-pyridyl) dibenzothiophen-3-yl group Group, 8- (2-pyridyl) dibenzothiophene-3-yl group, 9- (2-pyridyl) dibenzothiophene-3-yl group,
2- (2-Pyridyl) dibenzofuran-1-yl group, 3- (2-pyridyl) dibenzofuran-1-yl group, 4- (2-pyridyl) dibenzofuran-1-yl group, 6- (2-pyridyl) dibenzofuran -1-yl group, 7- (2-pyridyl) dibenzofuran-1-yl group, 8- (2-pyridyl) dibenzofuran-1-yl group, 9- (2-pyridyl) dibenzofuran-1-yl group, 1- (2-Pyridyl) dibenzofuran-2-yl group, 3- (2-pyridyl) dibenzofuran-2-yl group, 4- (2-pyridyl) dibenzofuran-2-yl group, 6- (2-pyridyl) dibenzofuran-2 -Il 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 Group, 7- (2-pyridyl) dibenzofuran-3-yl group, 8- (2-pyridyl) dibenzofuran-3-yl group, 9- (2-pyridyl) dibenzofuran-3-yl group, 3- (3-pyridyl) ) Thiofen-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, 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, 3- (3-pyridyl) benzothiophen-2-yl group, 4- (3-pyridyl) benzothiophen-2-yl group, 5- (3-pyridyl) benzo Thiophen-2-yl group, 6- (3-pyridyl) benzothiofen-2-yl group, 7- (3-pyridyl) benzothiofen-2-yl group, 2- (3-pyridyl) benzothiophen-3-yl Group, 4- (3-pyridyl) benzothiophen-3-yl group, 5- (3-pyridyl) benzothiophen-3-yl group, 6- (3-pyridyl) benzothiophen-3-yl group, 7- ( 3-Pyridyl) Benzothiophene- 3-yl group, 2- (3-pyridyl) benzothiophene-4-yl group, 3- (3-pyridyl) benzothiophen-4-yl group, 5- (3-pyridyl) benzothiophen-4-yl group, 6- (3-pyridyl) benzothiophene-4-yl group, 7- (3-pyridyl) benzothiophene-4-yl group, 2- (3-pyridyl) benzothiophene-5-yl group, 3- (3- (3-pyridyl) benzothiophene-4-yl group Pyridyl) benzothiophene-5-yl group, 4- (3-pyridyl) benzothiophene-5-yl group, 6- (3-pyridyl) benzothiophene-5-yl group, 7- (3-pyridyl) benzothiophene- 5-yl group, 2- (3-pyridyl) benzothiophene-6-yl group, 3- (3-pyridyl) benzothiophen-6-yl group, 4- (3-pyridyl) benzothiophen-6-yl group, 5- (3-pyridyl) benzothiophene-6-yl group, 7- (3-pyridyl) benzothiophene-6-yl group, 2- (3-pyridyl) benzothiophene-7-yl group, 3- (3- (3-pyridyl) benzothiophene-6-yl group Pyridyl) benzothiophene-7-yl group, 4- (3-pyridyl) benzothiophene-7-yl group, 5- (3-pyridyl) benzothiophene-7-yl group, 6- (3-pyridyl) benzothiophene- 7-yl group, 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 Il 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) 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) be Nzofran-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, 2- (3-pyridyl) dibenzothiophene-1-yl group, 3- (3-pyridyl) dibenzothiophene-1-yl group, 4 -(3-Pyridyl) dibenzothiophene-1-yl group, 6- (3-pyridyl) dibenzothiophene-1-yl group, 7- (3-pyridyl) dibenzothiophene-1-yl group, 8- (3-pyridyl) ) Dibenzothiophene-1-yl group, 9- (3-pyridyl) dibenzothiophene-1-yl group, 1- (3-pyridyl) dibenzothiophen-2-yl group, 3- (3-pyridyl) dibenzothiophene-2 -Il 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) dibenzothiophene-3-yl group, 2- (3-pyridyl) ) Dibenzothiophene-3-yl group, 4- (3-pyridyl) dibenzothiophene-3-yl group, 6- (3-pyridyl) dibenzothiophene-3-yl group, 7- (3-pyridyl) dibenzothiophene-3 -Il group, 8- (3-pyridyl) dibenzothiophene-3-yl group, 9- (3-pyridyl) dibenzothiophene-3-yl group, 2- (3-pyridyl) dibenzothiophene-1-yl group, 3-yl group (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 -Il group, 8- (3-pyridyl) dibenzofuran-1-yl group, 9- (3-pyridyl) dibenzofuran-1-yl group, 1- (3-pyridyl) dibenzofuran-2-yl group, 3- (3) -Pyridyl) dibenzofuran-2-yl group, 4- (3-pyridyl) dibenzofuran-2-yl group, 6- (3-pyridyl) dibenzofuran- 2-yl group, 7- (3-pyridyl) dibenzofuran-2-yl group, 8- (3-pyridyl) dibenzofuran-2-yl group, 9- (3-pyridyl) dibenzofuran-2-yl group, 1-( 3-Pyridyl) dibenzofuran-3-yl group, 2- (3-pyridyl) dibenzofuran-3-yl group, 4- (3-pyridyl) dibenzofuran-3-yl group, 6- (3-pyridyl) dibenzofuran-3-yl group Il group, 7- (3-pyridyl) dibenzofuran-3-yl group, 8- (3-pyridyl) dibenzofuran-3-yl group, 9- (3-pyridyl) dibenzofuran-3-yl group, 3- (4- (4-pyridyl) dibenzofuran-3-yl group 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,
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, 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) benzothiophene-3 -Il group, 6- (4-pyridyl) benzothiophene-3-yl group, 7- (4-pyridyl) benzothiophen-3-yl group, 2- (4-pyridyl) benzothiophen-4-yl group, 3 -(4-Pyridyl) benzothiophene-4-yl group, 5- (4-pyridyl) benzothiophene-4-yl group, 6- (4-pyridyl) benzothiophene-4-yl group, 7- (4-pyridyl) ) Benzothiophene-4-yl group, 2- (4-pyridyl) benzothiophene-5-yl group, 3- (4-pyridyl) benzothiophene-5-yl group, 4- (4-pyridyl) benzothiophene-5 -Il group, 6- (4-pyridyl) benzothiophene-5-yl group, 7- (4-pyridyl) benzothiophen-5-yl group, 2- (4-pyridyl) benzothiophene-6-yl group, 3 -(4-Pyridyl) benzothiophene-6-yl group, 4- (4-pyridyl) benzothiophene-6-yl group, 5- (4-pyridyl) benzothiophene-6-yl group, 7- (4-pyridyl) ) Benzothiophene-6-yl group, 2- (4-pyridyl) benzothiophen-7-yl group, 3- (4-pyridyl) benzothiophen-7-yl group, 4- (4-pyridyl) benzothiophene-7 -Il group, 5- (4-pyridyl) benzothiophene-7-yl group, 6- (4-pyridyl) benzothiophen-7-yl group, 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 -Il group, 2- (4-pyridyl) benzofra N-3-yl group, 4- (4-pyridyl) benzofuran-3-yl group, 5- (4-pyridyl) benzofuran-3-yl group, 6- (4-pyridyl) benzofuran-3-yl group, 7 -(4-Pyridyl) benzofuran-3-yl group, 2- (4-pyridyl) benzofuran-4-yl group, 3- (4-pyridyl) benzofuran-4-yl group, 5- (4-pyridyl) benzofuran- 4-yl group, 6- (4-pyridyl) benzofuran-4-yl group, 7- (4-pyridyl) benzofuran-4-yl group, 2- (4-pyridyl) benzofuran-5-yl group, 3-( 4-Pyridyl) benzofuran-5-yl group, 4- (4-pyridyl) benzofuran-5-yl group, 6- (4-pyridyl) benzofuran-5-yl group, 7- (4-pyridyl) benzofuran-5-yl group Il 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) 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, 2- (4-pyridyl) Dibenzothiophene-1-yl group, 3- (4-pyridyl) dibenzothiophene-1-yl group, 4- (4-pyridyl) dibenzothiophene-1-yl group, 6- (4-pyridyl) dibenzothiophene-1- Il group, 7- (4-pyridyl) dibenzothiophene-1-yl group, 8- (4-pyridyl) dibenzothiophene-1-yl group, 9- (4-pyridyl) dibenzothiophene-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 Il group, 1- (4-pyridyl) dibenzothiophene-3-yl group, 2- (4-pyridyl) dibenzothiophene-3-yl group, 4- (4-pyridyl) dibenzothiophen-3-yl Group, 6- (4-pyridyl) dibenzothiophene-3-yl group, 7- (4-pyridyl) dibenzothiophene-3-yl group, 8- (4-pyridyl) dibenzothiophene-3-yl group, 9- ( 4-pyridyl) dibenzothiophene-3-yl group,
2- (4-Pyridyl) dibenzofuran-1-yl group, 3- (4-pyridyl) dibenzofuran-1-yl group, 4- (4-pyridyl) dibenzofuran-1-yl group, 6- (4-pyridyl) dibenzofuran -1-yl group, 7- (4-pyridyl) dibenzofuran-1-yl group, 8- (4-pyridyl) dibenzofuran-1-yl group, 9- (4-pyridyl) dibenzofuran-1-yl group, 1- (4-Pyridyl) dibenzofuran-2-yl group, 3- (4-pyridyl) dibenzofuran-2-yl group, 4- (4-pyridyl) dibenzofuran-2-yl group, 6- (4-pyridyl) dibenzofuran-2 -Il 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 Group, 7- (4-pyridyl) dibenzofuran-3-yl group, 8- (4-pyridyl) dibenzofuran-3-yl group, 9- (4-pyridyl) dibenzofuran-3-yl group, 2- {8-( 2-Pyridyl) dibenzofuran-2-yl} phenyl group, 3-{8- (2-pyridyl) dibenzofuran-2-yl} phenyl group, 4-{8- (2-pyridyl) dibenzofuran-2-yl} phenyl group , 2- {8- (3-pyridyl) dibenzofuran-2-yl} phenyl group, 3- {8- (3-pyridyl) dibenzofuran-2-yl} phenyl group, 4- {8- (3-pyridyl) dibenzofuran -2-yl} phenyl group, 2-{8- (4-pyridyl) dibenzofuran-2-yl} phenyl group, 3-{8- (4-pyridyl) dibenzofuran-2-yl} phenyl group, 4-{8 -(4-Pyridyl) dibenzofuran-2-yl} phenyl group, 2- {8- (3-methyl-2-pyridyl) dibenzofuran-2-yl} phenyl group, 3- {8- (3-methyl-2-pyridyl) phenyl group Pyridyl) dibenzofuran-2-yl} phenyl group, 4- {8- (3-methyl-2-pyridyl) dibenzofuran-2-yl} phenyl group, 2- {8- (2-methyl-3-pyridyl) dibenzofuran- 2-yl} phenyl group, 3- {8- (2-methyl-3-pyridyl) dibenzofuran-2-yl} phenyl group, 4- {8- (2-methyl-3-pyridyl) ) Dibenzofuran-2-yl} phenyl group, 2- {8- (3-methyl-4-pyridyl) dibenzofuran-2-yl} phenyl group, 3- {8- (3-methyl-4-pyridyl) dibenzofuran-2 -Phenyl group, 4- {8- (3-methyl-4-pyridyl) dibenzofuran-2-yl} phenyl group, 2- {8- (2,6-dimethyl-3-pyridyl) dibenzofuran-2-yl } Phenyl group, 3-{8- (2,6-dimethyl-3-pyridyl) dibenzofuran-2-yl} Phenyl group, 4-{8- (2,6-dimethyl-3-pyridyl) dibenzofuran-2-yl } Phenyl group, 2- {8- (2-pyrimidyl) dibenzofuran-2-yl} phenyl group, 3-{8- (2-pyrimidyl) dibenzofuran-2-yl} phenyl group, 4- {8- (2-) Pyrimidyl) dibenzofuran-2-yl} phenyl group, 2- {8- (5-pyrimidyl) dibenzofuran-2-yl} phenyl group, 3-{8- (5-pyrimidyl) dibenzofuran-2-yl} phenyl group, 4 -{8- (5-pyrimidyl) dibenzofuran-2-yl} phenyl group, etc. are preferred examples. Of these substituents, phenyl group, p-tolyl group, biphenyl-3-yl group, biphenyl-4-yl group, 3- (1-naphthyl) phenyl group, 3 -(2-naphthyl) phenyl group, 4- (1-naphthyl) phenyl group, 4- (2-naphthyl) phenyl group, 3- (9-phenanthryl) phenyl group, 4- (9-phenanthryl) phenyl group, 3 -(Fluorenten-3-yl) phenyl group, 4- (fluoranthen-3-yl) phenyl group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 3- (3-pyridyl) Phenyl group, 4- (3-pyridyl) phenyl group, 3- (2-quinolyl) phenyl group, 4- (2-quinolyl) phenyl group, 3- (3-quinolyl) phenyl group, 4- (3-quinolyl) Phenyl group, 3- (5-methylthiophen-2-yl) phenyl group, 4- (5-methylthiophen-2-yl) phenyl group, 3- (5-methylfuran-2-yl) phenyl group, 4- (5-Methylfuran-2-yl) phenyl group, 3- (2-benzothienyl) phenyl group, 4- (2-benzothienyl) phenyl group, 3- (2-benzofuryl) phenyl group, 4- (2-) Phenyl benzofuryl) 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-phenylpyridine-6- Il group, 2-Phenylpyridine-5-Il group, 2-Phenylpyridine-4-Il group, 3-Phenylpyridine-5-Il group, 3-Phenylpyridine-6-Il group, 5-Phenylthiophene-2- Il group, 5-phenylfuran-2-yl group, 1-naphthyl group, 2-naphthyl group, 2-benzothienyl group, 2-benzofuryl group, 1-phenanthril group, 2-phenanthril group, 3-phenanthril group, 9 -Phenyl trill group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, 4-dibenzofuryl group, 2- {8- (3-methyl-2-pyridyl) dibenzofuran-2-yl} phenyl group , 3- {8- (3-Methyl-2-pyridyl) dibenzofuran-2-yl} phenyl group, 2- {8- (2,6-dimethyl) -3-Pyridyl) dibenzofuran-2-yl} phenyl group, 3-{8- (2,6-dimethyl-3-pyridyl) dibenzofuran-2-yl} phenyl group, 2-{8- (2-pyrimidyl) dibenzofuran -2-yl} phenyl group or 3- {8- (2-pyrimidyl) dibenzofuran-2-yl} phenyl group is preferable, and phenyl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-( 1-naphthyl) phenyl group, 3- (2-naphthyl) phenyl group, 4- (1-naphthyl) phenyl group, 4- (2-naphthyl) phenyl group, 3- (9-phenanthryl) phenyl group, 4- ( 9-Phenyl tril) phenyl group, 3- (fluorenten-3-yl) phenyl group, 4- (fluoranthen-3-yl) phenyl group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group , 3- (3-pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 3- (2-quinolyl) phenyl group, 4- (2-quinolyl) phenyl group, 3- (3-quinolyl) phenyl group , 4- (3-quinolyl) phenyl group, 3- (2-benzothienyl) phenyl group, 4- (2-benzothienyl) phenyl group, 3- (2-benzofuryl) phenyl group, 4- (2-benzofuryl) 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, 1-naphthyl group, 2-naphthyl group , 9-Phenyltril group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, 4-dibenzofuryl group and the like are more preferable.

A represents a single bond.

B ¹ and B ² represent a single bond or a hydrogen atom. However, ^{either B 1} or B ² represents a single bond to form a single bond with A, and the other represents a hydrogen atom.

One of Z ¹ and Z ² represents a nitrogen atom, and the other represents CH.

The compound represented by the general formula (1) can also be expressed as a compound represented by the general formula (1a) or (1b) as follows.

(In the general formulas (1a) and (1b), Ar ¹ Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ , Z ¹ , and Z ² are synonymous with the general formula (1). .)
In the general formulas (1a) and (1b), the preferable range of each definition is the same as that in the general formula (1).

When the triazine compound (1) of the present invention is used as a part of the constituent components of the organic electroluminescent element, effects such as high luminous efficiency, long life, and low voltage can be obtained. In particular, this effect is remarkable when used as an electron transport layer.

Among the compounds represented by the general formula (1), the following (A-1) to (A-960) can be exemplified as specific examples of particularly preferable compounds, but the present invention is not limited thereto. ..

Hereinafter, a method of using the triazine compound (1) will be described.

In a broad sense, the light emitting layer in an organic electroluminescent device refers to a layer that emits light when an electric current is passed through an electrode consisting of a cathode and an anode. Specifically, it refers to a layer containing a fluorescent compound that emits light when an electric current is passed through an electrode consisting of a cathode and an anode. Usually, an organic electroluminescent device has a structure in which a light emitting layer is sandwiched between a pair of electrodes.

The organic electroluminescent element of the present invention has a hole transport layer, an electron transport layer, an anode buffer layer, a cathode buffer layer and the like in addition to a light emitting layer, if necessary, and has a structure sandwiched between a cathode and an anode. Specifically, the structure shown below can be mentioned.
(I) anode / light emitting layer / cathode (ii) anode / hole transport layer / light emitting layer / cathode (iii) anode / light emitting layer / electron transport layer / cathode (iv) anode / hole transport layer / light emitting layer / electron Transport layer / cathode (v) anode / anode buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode buffer layer / cathode A conventionally known light emitting material is used for the light emitting layer in the organic electroluminescent element of the present invention. be able to. As a method for forming the light emitting layer, there is a method for forming a thin film by a known method such as a thin film deposition method, a spin coating method, a casting method, or an LB method.

Further, this light emitting layer can be obtained by dissolving a light emitting material together with a binder such as a resin in a solvent to form a solution, and then applying this to a thin film by a spin coating method or the like.

The film thickness of the light emitting 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.

Next, other layers such as a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer that are combined with a light emitting layer to form an organic electroluminescent device will be described.

The hole injection layer and the hole transport layer have a function of transmitting 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 electrons injected from the cathode and transported from the electron injection layer and / or the electron transport layer to the light emitting layer are holes due to the electron barrier existing at the interface between the light emitting layer and the hole injection layer or the hole transport layer. The element is accumulated at the interface in the light emitting layer without leaking to the injection layer or the hole transport layer, and is an element having excellent light emitting performance such as improved light emitting efficiency.

The hole injection material and the hole transport material have any of hole injection or transport and electron barrier properties, and may be either an organic substance or an inorganic substance. Examples of the hole injecting material and the hole transporting material include triazole derivative, oxadiazole derivative, imidazole derivative, polyarylalkane derivative, pyrazoline derivative and pyrazolone derivative, phenylenediamine derivative, arylamine derivative, amino-substituted calcon derivative and oxazole. Examples thereof include derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilben derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, especially thiophene oligomers. As the hole injecting material and the hole transporting material, the above-mentioned ones can be used, but porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, particularly aromatic tertiary amine compounds may be used. preferable.

Typical examples of the above aromatic tertiary amine compound and styrylamine compound are N, N, N', N'-tetraphenyl-4,4'-diaminophenyl, N, N'-diphenyl-N, N'. -Bis (3-methylphenyl)-[1,1'-biphenyl] -4,4'-diamine (TPD), 2,2-bis (4-di-p-tolylaminophenyl) propane, 1,1- Bis (4-di-p-tolylaminophenyl) cyclohexane, N, N, N', N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis (4-di-p-) Trillaminophenyl) -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) Audriphenyl, N, N, N-tri (p-tolyl) amine, 4- (di-p-tolylamino) -4'-[4- (di-p-tolylamino) styryl] Stilben, 4-N, N- Diphenylamino- (2-diphenylvinyl) benzene, 3-methoxy-4'-N, N-diphenylaminostillbenzene, N-phenylcarbazole, 4,4'-bis [N- (1-naphthyl) -N-phenyl Examples thereof include amino] biphenyl (NPD), 4,4', 4''-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (MTDATA).

Inorganic compounds such as p-type-Si and p-type-SiC can also be used as hole injection materials and hole transport materials. The hole injection layer and the hole transport layer are formed by thinning the hole injection material and the hole transport material by a known method such as a vacuum vapor deposition method, a spin coating method, a casting method, or an LB method. Can be formed. The film thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually about 5 nm to 5 μm. The hole injection layer and the hole transport layer may have a one-layer structure composed of one or more of the above materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.

In the organic electroluminescent device of the present invention, the electron transport layer contains the triazine compound represented by the above general formula (1).

The electron transport layer can be formed by forming a triazine compound represented by the general formula (1) into a film by a known thin film forming method such as a vacuum vapor deposition method, a spin coating method, a casting method, or an LB method. can. The film thickness of the electron transport layer is not particularly limited, but is usually selected in the range of 5 nm to 5 μm. Further, the electron transport layer may contain a triazine compound represented by the general formula (1) and may contain a conventionally known electron transport material, or may have a one-layer structure including one or more kinds. Alternatively, it may have a laminated structure composed of a plurality of layers having the same composition or a different composition.

Further, in the present invention, the light emitting material is not limited to the light emitting layer, and one kind may be contained in the hole transport layer or the electron transport layer adjacent to the light emitting layer, whereby the organic electroluminescent element may be further contained. The luminous efficiency of the

The substrate preferably used for the organic electroluminescent device of the present invention is not particularly limited in the types such as glass and plastic, and is not particularly limited as long as it is transparent. Examples of the substrate preferably used for the organic electroluminescent element of the present invention include glass, quartz, and a light-transmitting plastic film.

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

A suitable example for manufacturing the organic electroluminescent device of the present invention will be described. As an example, a method for manufacturing an organic electroluminescent device including the anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode will be described.

First, a thin film made of a desired electrode substance, for example, an anode substance, is formed on a suitable substrate by a method such as thin film deposition or sputtering so as to have a film thickness in the range of 1 μm or less, preferably 10 to 200 nm. Make an anode. Next, a thin film composed of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer / electron injection layer, which are element materials, is formed on this.

A buffer layer (electrode interface layer) may be present between the anode and the light emitting layer or the hole injection layer, and between the cathode and the light emitting layer or the electron injection layer.

Further, in addition to the above basic constituent layer, a layer having other functions may be laminated, if necessary, and a functional layer such as a hole block layer or an electron block layer may be provided.

Next, the electrode of the organic electroluminescent device of the present invention will be described. As the anode in the organic electroluminescent element, a metal having a large work function (4 eV or more), an alloy, an electrically conductive compound, or a mixture thereof as an electrode material is preferably used. Specific examples of such an electrode material include metals such as Au and conductive transparent materials such as _{CuI, indium tin oxide (ITO), SnO 2, and ZnO.}

The anode may form a thin film of these electrode materials by a method such as thin film deposition or sputtering to form a pattern having a desired shape by a photolithography method, or a pattern may be formed through a mask having a desired shape during vapor deposition or sputtering. May be formed.

On the other hand, as the cathode, a metal having a small work function (4 eV or less) (referred to as an electron-injectable metal), an alloy, an electrically conductive compound, or a mixture thereof as an electrode material is preferably used. Specific examples of such electrode materials 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 ) Examples include mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like. Among these, from the viewpoint of electron injectability and durability against oxidation, a mixture of an electron injectable metal and a second metal which is a stable metal having a larger work function value than this, for example, magnesium / silver mixture, magnesium. / Aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) mixture, lithium / aluminum mixture and the like are suitable. The cathode can be produced by forming a thin film of these electrode materials by a method such as thin film deposition or sputtering.

As described above, a thin film made of a desired electrode material, for example, an anode material, is formed on a suitable substrate by a method such as thin film deposition or sputtering so as to have a film thickness in the range of 1 μm or less, preferably 10 to 200 nm. After forming an anode, each layer thin film composed of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer / electron injection layer is formed on the anode as described above, and then for a cathode. A thin film made of a material is formed to have a thickness of 1 μm or less, preferably in the range of 50 to 200 nm, by a method such as vapor deposition or sputtering, and a cathode is provided to obtain a desired organic electric field light emitting element.

The organic electroluminescent element of the present invention may be used as a kind of lamp such as for lighting or an exposure light source, a projection device of a type for projecting an image, or a display of a type for directly visually recognizing a still image or a moving image. It may be used as a device (display). When used as a display device for video reproduction, the drive method may be either a simple matrix (passive matrix) method or an active matrix method. Further, a full-color display device can be manufactured by using two or more kinds of organic electroluminescent devices of the present invention having different emission colors.

It is sectional drawing of the single layer element produced in an Example.

1. 1. Glass substrate with ITO transparent electrode 2. Hole injection layer 3. Charge generation layer 4. Hole transport layer 5. Light emitting layer 6. Electron transport layer 7. Cathode layer Next, the manufacturing method of the present invention will be described.

The triazine compound (1) of the present invention has the following reaction formula (1) in the presence or absence of a base and in the presence of a palladium catalyst.

(In the reaction formula (1), Ar ¹ , Ar ² , Ar ³ , Z ¹ , and Z ² represent the same substituents as described above. Y represents a leaving group described later. M ¹ and M ² represent a leaving group described later. Represents a substituent to be used.),
Reaction equation (2)

(In the reaction formula (2), Ar ¹ , Ar ² , Ar ³ , Z ¹ , and Z ² represent the same substituents as described above. Y ¹ and Y ² represent a leaving group described later. M represents a leaving group described later. Represents a substituent to be used.)
It can be manufactured by the method indicated by.

Hereinafter, the compound represented by the general formula (2) will be referred to as compound (2). The same applies to compound (3) to compound (5). The definitions of these compounds will be described below.

Y represents a leaving group and is not particularly limited, and examples thereof include a chlorine atom, a bromine atom, an iodine atom and a triflate. Of these, a bromine atom or a chlorine atom is preferable because the reaction yield is good. However, it may be preferable to use triflate because of the availability of raw materials.

Regarding Y ¹ and Y ^{2 , either Y 1} or Y ^{2 has} the same meaning as Y, and the other represents a hydrogen atom.

M independently represents ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ . However, R ¹ and R ² independently represent a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group or a phenyl group having 1 to 4 ^{carbon atoms, and R 4} represents a hydrogen atom and 1 carbon atom. It represents an alkyl group or a phenyl group 4, B ^(oR ₄₎ 2 two ^{R 4} ₂ may be the same or different. Further, two R ⁴ may form a ring containing an oxygen atom and a boron atom together.

Examples of ZnR ¹ and MgR ² include ZnCl, ZnBr, ZnI, MgCl, MgBr, MgI and the like.

Examples of Sn (R ³ ) ₃ include Sn (Me) ₃ , Sn (Bu) _{3, and the like.}

Examples of B (OR ⁴ ) ₂ include B (OH) ₂ , B (OMe) ₂ , B (O ⁱ Pr) ₂ , B (OBu) _{2, and the like.} Further, ^{as an example of B (OR 4} ) ₂ ^{in the case where two R 4s} are integrated to form a ring containing an oxygen atom and a boron atom, the following (C-1) to (C-6) are used. The group shown in (C-2) is desirable because the group shown can be exemplified and the yield is good.

Regarding M ¹ and M ^{2 , either M 1} or M ^{2 has} the same meaning as M, and the other represents a hydrogen atom.

The compound (3) used in the reaction formula (1) is, for example, JP-A-2005-268199 [0105] to [0121], JP-A-2008-280330 [0061] to [0076], or JP-A-2001-. It can be produced by combining the methods disclosed in Japanese Patent Publication No. 335516 [0047] to [0087]. Examples of the compound (3) include the following (B-1) to (B-56), but the present invention is not limited thereto.

The compound (5) used in the reaction formula (2) represents a compound in which M ¹ and M ² of the compound (3) are replaced with ^{Y 1} and Y ² , respectively. Specific examples of the compound (5) include those in which M is replaced with Y in (B-1) to (B-56) above, but the present invention is not limited thereto. The definitions of M ¹ , M ² , Y ¹ , Y ² , M, and Y are as described above.
Can be exemplified.

Subsequently, the reaction formula (1) will be described. "Step 1" is a method for obtaining the triazine compound (1) of the present invention by reacting the compound (2) with the compound (3) in the presence or absence of a base or in the presence of a palladium catalyst. By applying the reaction conditions of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, and Stille reaction, the desired product can be obtained in good yield.

Examples of the palladium catalyst that can be used in "Step 1" include salts of palladium chloride, palladium acetate, palladium trifluoroacetate, and palladium nitrate. In addition, π-allyl palladium chloride dimer, palladium acetylacetonato, tris (dibenzylideneacetone) dipalladium, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium and dichloro (1,1'-bis (diphenylphos)). A complex compound such as fino) ferrocene) palladium can be exemplified. Among them, the palladium complex having a tertiary phosphine as a ligand is more preferable in that the reaction yield is good, and the palladium complex having triphenylphosphine as a ligand is more preferable in that the reaction yield is good. Especially preferable.

A palladium complex having a tertiary phosphine as a ligand can also be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or a complex compound. Examples of the tertiary phosphine that can be used at this time include triphenylphosphine, trimethylphosphine, tributylphosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5. -Bis (diphenylphosphine) xanthene, 2- (diphenylphosphine) -2'-(N, N-dimethylamino) biphenyl, 2- (di-tert-butylphosphine) biphenyl, 2- (dicyclohexylphosphine) Biphenyl, bis (diphenylphosphino) methane, 1,2-bis (diphenylphosphino) ethane, 1,3-bis (diphenylphosphino) propane, 1,4-bis (diphenylphosphino) butane, 1,1' -Bis (diphenylphosphino) ferrocene, tri (2-furyl) phosphine, tri (o-tolyl) phosphine, tris (2,5-kisilyl) phosphine, (±) -2,2'-bis (diphenylphosphine) Examples thereof include -1,1'-binaphthyl, 2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl and the like. 2-Dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl or triphenylphosphine is preferable because it is easily available and the reaction yield is good. The molar ratio of the tertiary phosphine to the palladium salt or the complex compound is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 in terms of good reaction yield.

Examples of the bases that can be used in "Step 1" include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, potassium phosphate, sodium phosphate, sodium fluoride, potassium fluoride, and foot. Potassium carbonate can be exemplified, and potassium carbonate is desirable in terms of good yield. The molar ratio of the base to the compound (3) is preferably 1: 2 to 10: 1, and more preferably 1: 1 to 3: 1 in terms of good yield.

The molar ratio of the compound (2) to the compound (3) used in "Step 1" is preferably 1: 2 to 5: 1, and more preferably 1: 2 to 2: 1 in terms of good yield.

Examples of the solvent that can be used in "Step 1" include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, toluene, benzene, diethyl ether, ethanol, methanol, xylene and the like. It may be used in an appropriate combination. It is desirable to use dioxane or a mixed solvent of tetrahydrofuran and water in terms of good yield.

"Step 1" can be carried out at a temperature appropriately selected from 0 ° C. to 150 ° C., and is more preferably carried out at 50 ° C. to 100 ° C. in terms of good yield.

Compound (1) can be obtained by subjecting it to a normal treatment after the completion of "step 1". If necessary, it may be purified by recrystallization, column chromatography, sublimation or the like.
"Step 2" is a method for obtaining the triazine compound (1) of the present invention by reacting the compound (4) with the compound (5) in the presence or absence of a base or in the presence of a palladium catalyst. By applying the reaction conditions of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, and Stille reaction, the desired product can be obtained in good yield. In "step 2", among the conditions mentioned in "step 1", the condition in which the compound (2) is replaced with the compound (5) and the compound (3) is replaced with the compound (4) can be applied. However, the reaction conditions do not have to be the same as in "Step 1". After the completion of "Step 2", purification may be performed by recrystallization, column chromatography, sublimation or the like, if necessary.

The triazine compound (1) of the present invention is suitably used as a material for an organic electroluminescent device.

Further, the triazine compound (1) of the present invention is suitably used as an electron transport material or an electron injection material for an organic electroluminescent device.

The triazine compound (1) of the present invention is effective when used as a component of an organic electroluminescent device. In particular, when used as an electron transport layer, effects such as longer life, higher efficiency, and lower voltage can be obtained as compared with conventional devices. Further, when the triazine compound (1) of the present invention is used as a material for an organic electric field light emitting element, it can also be used as a co-deposited film with an arbitrary organometallic species, an organic compound or an inorganic compound.

The method for producing a thin film for an organic electroluminescent device made of the triazine compound (1) of the present invention is not particularly limited, but a film formation by a vacuum vapor deposition method is possible. The film formation by the vacuum vapor deposition method can be performed by using a general-purpose vacuum vapor deposition apparatus. The degree of vacuum in the vacuum chamber when forming a film by the vacuum vapor deposition method is generally used for diffusion pumps, turbo molecular pumps, cryopumps, etc., considering the manufacturing tact time and manufacturing cost of manufacturing organic electric field light emitting elements. preferably ^{1 × 10 -2 ~1 × 10 -5} ~1 × 10 -6 about Pa that can be reached by, more preferably from 1 × ¹⁰ -3 ~10 -6 Pa. The vapor deposition rate is preferably 0.005 to 1.0 nm / sec, more preferably 0.01 to 1 nm / sec, depending on the thickness of the film to be formed. Further, since the triazine compound (1) of the present invention has high solubility in chloroform, dichloromethane, 1,2-dichloroethane, chlorobenzene, toluene, ethyl acetate, tetrahydrofuran-, etc., a spin coat method using a general-purpose device, Chloroform can also be formed by an inkjet method, a casting method, a dip method, or the like.

Typical structures of the organic electroluminescent device to which the effect of the present invention can be obtained include a substrate, an anode, a hole injection layer, a hole transport layer light emitting layer, an electron transport layer, and a cathode.

The anode and cathode of the organic electroluminescent device are connected to a power source via an electrical conductor. By applying an electric potential between the anode and the cathode, the organic electroluminescent device operates. Holes are injected into the organic electroluminescent device from the anode, and electrons are injected into the organic electroluminescent device at the cathode.

The organic electroluminescent device is typically overlaid on the substrate and the anode or cathode can be in contact with the substrate. The electrodes that come into contact with the substrate are called lower electrodes for convenience. Generally, the lower electrode is an anode, but the organic electroluminescent device of the present invention is not limited to such a form. The substrate may be light transmissive or opaque, depending on the intended emission direction. The light transmission characteristics are desirable for viewing electroluminescence emission through the substrate. Clear glass or plastic is commonly employed as such a substrate. The substrate may have a composite structure including multiple material layers.

If electroluminescence emission is seen through the anode, the anode should pass or substantially pass the emission. Common transparent anode materials used in the present invention are indium-tin oxide (ITO), indium-zinc oxide (IZO), or tin oxide, but other metal oxides such as, for example. Aluminum or indium-doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide is also useful. In addition to these oxides, metal nitrides such as gallium nitride, metal seleniums such as zinc selenide, or metal sulfides such as zinc sulfide can be used as anodes. The anode can be modified with plasma-deposited fluorocarbons. For applications where electroluminescence emission is seen only through the cathode, the transmission properties of the anode are not important and any transparent, opaque or reflective conductive material can be used. Examples of conductors for this application include gold, iridium, molybdenum, palladium and platinum.

A hole injection layer can be provided between the anode and the hole transport layer. The hole injection material can help improve the film-forming properties of the subsequent organic layer and facilitate the injection of holes into the hole transport layer. Examples of materials suitable for use in the hole infusion layer include porphyrin compounds, plasma-deposited fluorocarbon polymers, and amines with aromatic rings such as biphenyl and carbazole groups, such as m-MTDATA (4,4'). , 4''-Tris [(3-methylphenyl) phenylamino] triphenylamine), 2T-NATA (4,4', 4''-Tris [(N-naphthalen-2-yl) -N-phenylamino) ] Triphenylamine), triphenylamine, tritrilamine, trildiphenylamine, N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine, N, N, N'N'-tetrakis (4-methylphenyl) -1,1'-biphenyl-4,4'-diamine, MeO-TPD (N, N, N'N'-tetrakis (4-methoxyphenyl) ) -1,1'-biphenyl-4,4'-diamine), N, N'-diphenyl-N, N'-dinaphthyl-1,1'-biphenyl-4,4'-diamine, N, N'- Bis (methylphenyl) -N, N'-bis (4-normalbutylphenyl) phenanthrene-9,10-diamine, or N, N'-diphenyl-N, N'-bis (9-phenylcarbazole-3-yl) ) -1,1'-biphenyl-4,4'-diamine and the like.

The hole transport layer of the organic electroluminescent device preferably contains one or more hole transport compounds, such as an aromatic tertiary amine. Aromatic tertiary amines mean that they are compounds containing one or more trivalent nitrogen atoms, which trivalent nitrogen atoms are bonded only to carbon atoms, and one or more of these carbon atoms are attached. It forms an aromatic ring. Specifically, the aromatic tertiary amine may be an arylamine, for example, a monoarylamine, a diarylamine, a triarylamine, or a high molecular weight arylamine.

As the hole transport material, an aromatic tertiary amine having one or more amine groups can be used. In addition, polymer hole transport materials can be used. For example, poly (N-vinylcarbazole) (PVK), polythiophene, polypyrrole, polyaniline and the like can be used. For example, NPD (N, N'-bis (naphthalene-1-yl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine), α-NPD (N, N'-diamine) (1-naphthyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine), TPBi (1,3,5-tris (1-phenyl-1H-benzimidazol-2-yl) ) Benzene), TPD (N, N'-bis (3-methylphenyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine) and the like.

Dipyrazino [2,3-f: 2', 3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile as a charge generation layer between the hole injection layer and the hole transport layer A layer containing (HAT-CN) may be provided.

The light emitting layer of the organic electroluminescent device contains a phosphorescent material or a fluorescent material, in which case light emission occurs as a result of the recombination of electron-hole pairs in this region. The light emitting layer may consist of a single material containing both small molecules and polymers, but more generally it consists of a host material doped with a guest compound, in which case the light emission is predominantly from the dopant. It arises and can have any color.

Examples of the host material of the light emitting layer include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthryl group. For example, DPVBi (4,4'-bis (2,2-diphenylvinyl) -1,1'-biphenyl), BCzVBi (4,4'-bis (9-ethyl-3-carbazobinylene) 1,1'-biphenyl. ), TBADN (2-talshalbutyl-9,10-di (2-naphthyl) anthracene), ADN (9,10-di (2-naphthyl) anthracene), CBP (4,4'-bis (carbazole-9) -Il) biphenyl), CDBP (4,4'-bis (carbazole-9-yl) -2,2'-dimethylbiphenyl), 9,10-bis (biphenyl) anthracene and the like.

The host material in the light emitting layer may be an electron transport material as defined below, a hole transport material as defined above, another material that supports hole-electron recombination, or a combination of these materials.

Examples of useful fluorescent dopants include anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine and quinacridone, dicyanomethylenepyrine compounds, thiopyran compounds, polymethine compounds, pyrylium, or thiapyrylium compounds, fluorene derivatives, perifuranthene derivatives, indeno. Examples thereof include perylene derivatives, bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, and carbostylyl compounds.

Examples of useful phosphorescent dopants include organic metal complexes of transition metals of iridium, platinum, palladium or osmium.

Examples of dopants are Alq ₃ (tris (8-hydroxyquinoline) aluminum), DPAVBi (4,4'-bis [4- (di-para-tolylamino) styryl] biphenyl), perylene, Ir (PPy) ₃ ( Examples thereof include tris (2-phenylpyridine) iridium (III), FlrPic (bis (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III)), and the like.

The thin film-forming material used to form the electron transport layer of the organic electroluminescent element of the present invention is the triazine compound (1) of the present invention. The electron transport layer may contain other electron transport materials, and examples of the electron transport materials include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Desirable alkali metal complexes, alkaline earth metal complexes, earth metal complexes include, for example, 8-hydroxyquinolinate lithium (Liq), bis (8-hydroxyquinolinate) zinc, bis (8-hydroxyquinolinate). Copper, bis (8-hydroxyquinolinate) manganese, tris (8-hydroxyquinolinate) aluminum, tris (2-methyl-8-hydroxyquinolinate) aluminum, tris (8-hydroxyquinolinate) gallium, Bis (10-hydroxybenzo [h] quinolinate) berylium, bis (10-hydroxybenzo [h] quinolinate) zinc, bis (2-methyl-8-quinolinate) chlorogallium, bis (2-methyl-8-quinolinate) ( Examples thereof include o-cresolate) gallium, bis (2-methyl-8-quinolinate) -1-naphtholate aluminum, and bis (2-methyl-8-quinolinate) -2-naphtholate gallium.

A hole blocking layer may be provided between the light emitting layer and the electron transport layer for the purpose of improving the carrier balance. Desirable compounds for the hole blocking layer are BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphenyl (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2). −Methyl-8-quinolinolate) -4- (phenylphenanthroline) aluminum), bis (10-hydroxybenzo [h] quinolinate) beryllium) and the like.

In the organic electroluminescent element of the present invention, an electron injection layer may be provided for the purpose of improving the electron injection property and the element characteristics (for example, luminous efficiency, low voltage drive, or high durability).

Desirable compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fleolenilidenemethane, anthraquinodimethane, or anthron. And so on. Also, metal complexes and the alkali metal oxides noted above, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth _{halides, SiO X, AlO X, SiN} X, SiON, Inorganic compounds such as various oxides, nitrides, and oxide nitrides such as AlON, GeO _X , LiO _X , LiON, TiO _X , TiON, TaO _X , TaON, TaN _{X, and C can also be used.}

The cathode used in the present invention can be formed from almost any conductive material if the emission is only seen through the anode. Desirable cathode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium / copper mixtures, magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al ₂ O ₃ ) mixtures, indium. , Lithium / aluminum mixture, rare earth metals and the like.

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

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

The emission characteristics of the organic electroluminescent element were evaluated using a luminance meter of LUMINANCEMEMETER (BM-9) (manufactured by TOPCON) by applying a direct current to the manufactured element at room temperature.

Example-1

3- (4,6-diphenylpyridin-2-yl) phenylboronic acid (1.09 g, 3.09 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3, under an argon stream 5-Triazine (1.00 g, 2.58 mmol) and tetrakis (triphenylphosphine) palladium (96 mg, 0.077 mmol) were suspended in tetrahydrofuran (50 mL). To this was added a 2 M aqueous potassium carbonate solution (4.0 mL, 8.00 mmol), and the mixture was stirred at 75 ° C. for 31 hours. After allowing to cool to room temperature, the reaction solution was concentrated under reduced pressure. Water (50 mL), methanol (50 mL), tetrahydrofuran (10 mL), and hexane (50 mL) were added to the obtained slurry, and the mixture was stirred at 75 ° C., and the precipitated solid was filtered off. The obtained solid was washed with water (50 mL), methanol (50 mL) and hexane (50 mL). The solid was dissolved in ethyl acetate (200 mL), filtered through cerite, and the filtrate was concentrated under reduced pressure. The solid obtained by drying this concentrate is purified by recrystallization (ethyl acetate) to purify the desired 4,6-diphenyl-2- [3'-(4,6-diphenylpyridine-2-yl). ) -Biphenyl-3-yl] -1,3,5-triazine (Compound A-1) was obtained as a white solid (yield 0.95 g, yield 60%).

^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.35-7.57 (m, 12H), 7.63 (dd, J = 16,8.0Hz, 2H), 7.72 (d, J) = 7.6Hz, 2H), 7.77 (d, J = 7.7Hz, 1H), 7.88-7.90 (m, 2H), 7.94 (s, 1H), 8.16-8 .21 (m, 3H), 8.48 (s, 1H), 8.73-8.76 (m, 5H), 9.04 (s, 1H).
Example-2

2- (2-bromophenyl) -4,6-diphenylpyridine (1.00 g, 2.59 mmol), 2- [3-{(4,4,5,5-tetramethyl-1,3) under argon airflow. , 2-Dioxaborolan-2-yl) phenyl}] -4,6-diphenyl-1,3,5-triazine (1.47 g, 3.38 mmol), and tetrakis (triphenylphosphine) palladium (0.121 g, 0). .105 mmol) was suspended in tetrahydrofuran (26 mL). To this was added a 2 M aqueous potassium carbonate solution (3.9 mL, 7.80 mmol), and the mixture was stirred at 75 ° C. for 49 hours. After allowing to cool to room temperature, the reaction solution was concentrated under reduced pressure. Methanol (30 mL) and ethyl acetate (5 mL) were added to the obtained concentrate, and the mixture was stirred at 78 ° C., and the precipitated solid was filtered off. The obtained solid was washed with water (30 mL), methanol (30 mL) and hexane (30 mL). This solid was dissolved in ethyl acetate (200 mL), 10 mg of activated carbon was added, the mixture was filtered through cerite, and the filtrate was concentrated under reduced pressure. Hexane (30 mL) and ethyl acetate (5 mL) were added to the obtained concentrate, and the mixture was stirred at 70 ° C. and the precipitated solid was filtered off. The obtained solid was purified by silica gel column chromatography (chloroform: hexane) to obtain the desired 4,6-diphenyl-2- [2'-(4,6-diphenylpyridine-2-yl) -biphenyl-3. -Il] -1,3,5-triazine (Compound A-421) was obtained as a white solid (yield 1.52 g, yield 76%).

^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.24-7.34 (m, 9H), 7.38 (t, J = 7.3Hz, 4H), 7.44-7.54 (m) , 6H), 7.58 (m, 1H), 7.64 (s, 1H), 7.81 (m, 2H), 7.91 (m, 1H), 8.61 (d, J = 8. 1Hz, 4H), 8.63-8.66 (m, 1H), 8.68 (m, 1H).
Example-3

1.00 g of 3- (4,6-diphenylpyridine-2-yl) phenylboronic acid was changed to 1.26 g of 3- [4- (4-dibenzofuryl) -6-phenylpyridine-2-yl] phenylboronic acid. 4,6-diphenyl-2-{3'-[4- (4-dibenzofuryl) -6-phenylpyridin-2-yl] -biphenyl-3-yl} in the same manner as in Example-1 except that A white solid (yield 68%) of -1,3,5-triazine (Compound A-41) was obtained.
The Tg of the obtained compound was 116 ° C.

^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.32 (t, J = 7.5Hz, 1H), 7.37-7.58 (m, 12H), 7.64 (t, J = 7) 9.9Hz, 2H), 7.74 (d, J = 7.6Hz, 1H), 7.79 (d, J = 7.6Hz, 1H), 7.90 (d, J = 7.7Hz, 1H) , 7.95 (d, J = 7.5Hz, 1H), 7.99 (d, J = 7.6Hz, 1H), 8.22-8.27 (m, 5H), 8.54 (s,, 1H), 8.72-8.76 (m, 5H), 9.05 (s, 1H).
Example-4

Performed except that 1.00 g of 2- (2-bromophenyl) -4,6-diphenylpyridine was changed to 1.23 g of 2- (2-bromophenyl) -4- (4-dibenzofuryl) -6-phenylpyridine. Similar to Example-2, 4,6-diphenyl-2-{2'-[4- (4-dibenzofuryl) -6-phenylpyridin-2-yl] -biphenyl-3-yl} -1,3 , 5-Triazine (Compound A-461) was obtained as a white solid (yield 72%).
^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.21-7.36 (m, 11H), 7.42-7.47 (m, 4H), 7.50-7.56 (m, 3H) ), 7.59-7.63 (m, 2H), 7.81-7.85 (m, 4H), 7.91-7.96 (m, 1H), 8.06 (s, 1H), 8.59 (d, J = 6.8Hz, 4H), 8.63 (d, J = 7.8Hz, 1H), 8.74 (s, 1H).
Example-5

Performed except that 1.00 g of 2- (2-bromophenyl) -4,6-diphenylpyridine was changed to 1.23 g of 2- (2-bromophenyl) -4- (2-dibenzofuryl) -6-phenylpyridine. Similar to Example-2, 4,6-diphenyl-2-{2'-[4- (2-dibenzofuryl) -6-phenylpyridin-2-yl] -biphenyl-3-yl} -1,3 , 5-Triazine (Compound A-467) was obtained as a white solid (yield 53%).
^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.04 (t, J = 7.6Hz, 1H), 7.28-7.63 (m, 20H), 7.72 (s, 1H), 7.76 (d, J = 7.8Hz, 1H), 7.93 (d, J = 6.2Hz, 2H), 7.99-8.03 (m, 1H), 8.63 (d, J) = 6.9Hz, 4H), 8.77-8.80 (m, 2H).
Example-6

Under a nitrogen stream, 4- (2-bromophenyl) -2- (4-biphenyl) -6-phenylpyridine (3.0 g, 6.49 mmol), 2- [3-{(4,4,5,5-) Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}] -4,6-diphenyl-1,3,5-triazine (3.00 g, 6.49 mmol), palladium acetate (29.1 mg, 0) .130 mmol) and 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl (124 mg, 0.260 mmol) were suspended in toluene (50 mL). A 4.0 M aqueous sodium hydroxide solution (4.87 mL, 19.5 mmol) was added thereto, and the mixture was stirred at 100 ° C. for 4 hours. After allowing to cool to room temperature, the reaction solution was concentrated under reduced pressure. Water (30 mL) and methanol (60 mL) were added to the obtained concentrate, and the precipitated solid was filtered off. By purifying the obtained solid by silica gel column chromatography (chloroform / hexane), the desired 2- {2'-[2- (4-biphenyl) -6-phenylpyridine-4-yl] -biphenyl-3 -Il} -4,6-diphenyl-1,3,5-triazine (Compound A-754) was obtained as a white solid (yield 4.14 g, yield 92%).
^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.33-7.68 (m, 24H), 7.96 (d, J = 7.8Hz, 2H), 8.01 (d, J = 8) .4Hz, 2H), 8.69 (d, J = 7.2Hz, 5H), 8.78 (s, 1H).
Example-7

Under a nitrogen stream, 4- (3-bromophenyl) -2- (4-biphenyl) -6-phenylpyridine (3.0 g, 6.49 mmol), 2- [3-{(4,4,5,5-) Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}] -4,6-diphenyl-1,3,5-triazine (3.00 g, 6.49 mmol), palladium acetate (29.1 mg, 0) .130 mmol) and 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl (124 mg, 0.260 mmol) were suspended in toluene (50 mL). A 4.0 M aqueous sodium hydroxide solution (4.87 mL, 19.5 mmol) was added thereto, and the mixture was stirred at 100 ° C. for 2 hours. After allowing to cool to room temperature, the reaction solution was concentrated under reduced pressure. Water (30 mL) and methanol (60 mL) were added to the obtained concentrate, and the precipitated solid was filtered off. By purifying the obtained solid by silica gel column chromatography (chloroform / hexane), the desired 2- {3'-[2- (4-biphenyl) -6-phenylpyridine-4-yl] -biphenyl-3 -Il} -4,6-diphenyl-1,3,5-triazine (Compound A-334) was obtained as a white solid (yield 3.87 g, yield 86%).
The Tg of the obtained compound was 107 ° C.
^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.39 (d, J = 7.2Hz, 1H), 7.46-7.62 (m, 11H), 7.67-7.77 (m) , 6H), 7.83 (d, J =, 8.1Hz, 1H), 7.87 (d, J = 7.8Hz, 1H), 7.93 (d, J = 7.5Hz, 1H), 8.01 (s, 1H), 8.05 (s, 1H), 8.11 (s, 1H), 8.26 (d, J = 8.1Hz, 2H), 8.33 (d, J = 7.8Hz, 2H), 8.79-8.85 (m, 5H), 9.09 (s, 1H).
Example-8

1.00 g of 2- (2-bromophenyl) -4,6-diphenylpyridine was changed to 1.26 g of 2- (3-bromophenyl) -4- (1-naphthyl) -6- (2-naphthyl) pyridine. 4,6-Diphenyl-2-{3'-[4- (1-naphthyl) -6- (2-naphthyl) pyridin-2-yl] -biphenyl-3-yl, except for Example-2. Il} -1,3,5-triazine (Compound A-7) was obtained as a white solid (yield 47%).
^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.55 (m, 12H), 7.64 (dd, J = 7.4Hz, 2H), 7.80 (d, J = 7) .3Hz, 2H), 7.87-7.96 (m, 7H), 7.99 (s, 1H), 8.24 (d, J = 8.0Hz, 1H), 8.37 (d, J) = 8.4Hz, 1H), 8.51 (s, 1H), 8.61 (s, 1H), 8.71-8.74 (m, 5H), 9.04 (s, 1H).
Synthesis Example-1

1.00 g of 3- (4,6-diphenylpyridine-2-yl) phenylboronic acid was changed to 1.09 g of 3- [4- (3-chlorophenyl) -6-phenylpyridine-2-yl] phenylboronic acid. 4,6-Diphenyl-2-{3'-[4- (3-chlorophenyl) -6-phenylpyridin-2-yl] -biphenyl-3-yl} -1 in the same manner as in Example-1 except. , 3,5-Triazine white solid (77% yield) was obtained.

^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.35-7.66 (m, 14H), 7.69 (m, 1H), 7.77 (d, J = 7.6Hz, 1H), 7.83 (s, 1H), 7.87-7.90 (m, 2H), 8.15-8.20 (m, 3H), 8.47 (s, 1H), 8.72-8. 76 (m, 5H), 9.02 (s, 1H).
Example-9

Under an argon stream, 4,6-diphenyl-2-{3'-[4- (3-chlorophenyl) -6-phenylpyridin-2-yl] -biphenyl-3-yl} -1,3,5-triazine ( 1.00 g, 1.54 mmol), 3-pyridineboronic acid (0.52 g, 4.23 mmol), palladium acetate (14.8 mg, 0.066 mmol), and 2-dicyclohexylphosphino-2', 4', 6 '-Triisopropylbiphenyl (61.8 mg, 0.130 mmol) was suspended in tetrahydrofuran (70 mL) and stirred at 75 ° C. for 48 hours. After allowing to cool to room temperature, the reaction solution was concentrated under reduced pressure. Water (50 mL) and methanol (10 mL) were added to the obtained slurry, and the precipitated solid was filtered off and washed with water (30 mL), methanol (30 mL), and hexane (30 mL). The obtained solid was purified by silica gel column chromatography (chloroform) to obtain the desired 4,6-diphenyl-2- (3'-{4- [3- (3-pyridyl) phenyl] -6-phenylpyridine. A white solid (yield 0.90 g, yield 84%) of -2-yl} -biphenyl-3-yl) -1,3,5-triazine (Compound A-96) was obtained.

^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.33-7.62 (m, 14H), 7.74 (t, J = 6.2Hz, 2H), 7.85-7.92 (m) , 5H), 8.17 (d, J = 7.7Hz, 3H), 8.47 (s, 1H), 8.56 (d, J = 4.2Hz, 1H), 8.70 (d, J) = 7.5Hz, 5H), 8.86 (s, 1H), 9.00 (s, 1H).
Example-10

4,6-diphenyl-2- (3'-{4- [3- (3'-{4- [3- (3'-{4- [3- (3'-{4- [3- ( 4-Pyridyl) phenyl] -6-phenylpyridin-2-yl} -biphenyl-3-yl) -1,3,5-triazine (Compound A-932) was obtained as a white solid (yield 23%).

^{1 1} H-NMR (CDCl ₃ ) δ (ppm): 7.36-7.54 (m, 9H), 7.62 (t, J = 7.9Hz, 2H), 7.70 (t, J = 7) .5Hz, 1H), 7.76 (d, J = 7.8Hz, 2H), 7.85 (m, 2H), 7.90-7.94 (m, 2H), 7.99-8.08 (M, 3H), 8.17 (t, J = 8.4Hz, 3H), 8.44 (s, 1H), 8.68-8.74 (m, 7H), 8.99 (s, 1H) ).

4,6-diphenyl-2- [4'-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl] -1,3,5-triazine (ETL-) described in WO2016 / 002864. 3. Compared with compound A-721) of Patent Document 2, it can be seen that the cyclic azine compound of the present invention has a high triplet excitation level.

Next, element evaluation will be described.

The structural formulas and abbreviations of the compounds used for device evaluation are shown below.

Element Example 1
As the substrate, a glass substrate with an ITO transparent electrode in which a 2 mm wide indium tin oxide (ITO) film (thickness 110 nm) was patterned in a stripe shape was used. This substrate was washed with isopropyl alcohol and then surface-treated by ozone ultraviolet washing. A substrate after cleaning and vacuum deposition of each layer in the vacuum deposition method to produce a light-emitting area 4 mm ² The organic electroluminescent device as shown in the sectional view of FIG. 1. Each organic material was formed into a film by a resistance heating method.

First, the glass substrate was introduced into the vacuum vapor deposition tank, and the pressure was reduced to ^{1.0 × 10 -4 Pa.}

After that, the hole injection layer 2, the charge generation layer 3, the hole transport layer 4, the light emitting layer 5, the electron transport layer 6, and the cathode layer are formed as organic compound layers on the glass substrate with the ITO transparent electrode shown in FIG. 7 were laminated in this order, and all of them were formed by vacuum vapor deposition.

As the hole injection layer 2, sublimated and purified HIL was formed into a 65 nm film at a rate of 0.15 nm / sec.

As the charge generation layer 3, a sublimated and purified HAT was formed into a 5 nm film at a rate of 0.05 nm / sec.

As the hole transport layer 4, HTL was formed into a 10 nm film at a rate of 0.15 nm / sec.

As the light emitting layer 5, EML-1 and EML-2 were formed into a film at a ratio of 95: 5 at a ratio of 25 nm (film formation rate 0.18 nm / sec).

As the electron transport layer 6, 4,6-diphenyl-2- [3'-(4,6-diphenylpyridine-2-yl) -biphenyl-3-yl] -1,3, which was synthesized in Example-1 5-Triazine (Compound A-1) and Liq were formed at a ratio of 50:50 (weight ratio) at 30 nm (deposition rate 0.15 nm / sec).

Finally, a metal mask was arranged so as to be orthogonal to the ITO stripe, and the cathode layer 7 was formed into a film. The cathode layer 7 deposits silver / magnesium (weight ratio 1/10) and silver in this order at 80 nm (deposition rate 0.5 nm / sec) and 20 nm (deposition rate 0.2 nm / sec), respectively. It has a two-layer structure.

Each film thickness was measured with a stylus type film thickness measuring meter (DEKTAK).

Further, this device was sealed in a nitrogen atmosphere glove box having an oxygen and water concentration of 1 ppm or less. For sealing, a glass sealing cap and the film-forming substrate epoxy type ultraviolet curable resin (manufactured by Nagase ChemteX Corporation) were used.

A direct current was applied to the organic electroluminescent device manufactured as described above, and the light emission characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON. As the light emission characteristics, the voltage (V) and the current efficiency (cd / A) when a current density of 10 mA / cm ² was passed were measured, and the element life (h) at the time of continuous lighting was measured. Incidentally, Table 2 of element lifetime (h) measures the luminance decay time at the time of continuous lighting when driving was prepared device at an initial luminance 800 cd / ^{m 2,} to the luminance (cd / ^{m 2)} is reduced by 10% The time required for was measured. The element life is shown as a relative value with the element life (h) in the element reference example 1 described later as a reference value (100). The results are shown in Table 2.

Element Example 2
In the element Example 1, 4,6-diphenyl-2- [2'-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl synthesized in Example-2 instead of compound A-1 ] -1,3,5-Triazine (Compound A-421) was used, but an organic electric field light emitting device was prepared and evaluated by the same method as in Device Example 1. The results are shown in Table 2. The element life was expressed as a relative value with the element life of the element reference example 1 as 100 after measuring the element life (h).

Element reference example 1
In Device Example 1, 2- [5- (9-phenanthril) -4'-(2-pyrimidyl) biphenyl-3-yl] -4 described in JP-A-2011-063584 instead of compound A-2. , 6-Diphenyl-1,3,5-triazine (ETL-1) was used, but an organic electroluminescent device was produced and evaluated by the same method as in Device Example 1. The results are shown in Table 2. Regarding the element life, after measuring the element life (h), the element life of this element reference example 1 was set as a reference value (100).

Element Example 3
As the substrate, a glass substrate with an ITO transparent electrode in which a 2 mm wide indium tin oxide (ITO) film (thickness 110 nm) was patterned in a stripe shape was used. This substrate was washed with isopropyl alcohol and then surface-treated by ozone ultraviolet washing. Each layer was vacuum-deposited on the washed substrate by a vacuum-film deposition method ^{to prepare a 2} organic electroluminescent device having a light emitting area of 4 mm. Each organic material was formed into a film by a resistance heating method.

First, the glass substrate was introduced into the vacuum vapor deposition tank, and the pressure was reduced to ^{1.0 × 10 -4 Pa.}

After that, as an organic compound layer on a glass substrate with an ITO transparent electrode, a hole injection layer, a charge generation layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a first electron transport layer, and a second electron The transport layer and the cathode layer were laminated in this order, and both were formed by vacuum vapor deposition.

As the hole injection layer, sublimated and purified HIL was formed into a 55 nm film at a rate of 0.15 nm / sec.

As the charge generation layer, a sublimated and purified HAT was formed into a 5 nm film at a rate of 0.05 nm / sec.

As the first hole transport layer, HTL was formed at a rate of 0.15 nm / sec to 10 nm.

As the second hole transport layer, HTL-2 was formed into a 10 nm film at a rate of 0.15 nm / sec.

As the light emitting layer, EML-3 and EML-4 were formed into a film at a ratio of 95: 5 at a ratio of 25 nm (film formation rate 0.18 nm / sec).

As the first electron transport layer, ETL-2 was formed into a 5 nm film at a rate of 0.15 nm / sec.

As the second electron transport layer, 4,6-diphenyl-2- {3'-[4- (4-dibenzofuryl) -6-phenylpyridin-2-yl] -biphenyl-3 synthesized in Example-3. -Il} -1,3,5-triazine (Compound A-41) and Liq were deposited at a ratio of 50:50 (weight ratio) at 25 nm (deposition rate 0.15 nm / sec).

Finally, a metal mask was arranged so as to be orthogonal to the ITO stripe, and the cathode layer 19 was formed into a film.

In the cathode layer, silver / magnesium (weight ratio 1/10) and silver are deposited in this order at 80 nm (deposition rate 0.5 nm / sec) and 20 nm (deposition rate 0.2 nm / sec), respectively. It has a two-layer structure.

Each film thickness was measured with a stylus type film thickness measuring meter (DEKTAK).

Further, this device was sealed in a nitrogen atmosphere glove box having an oxygen and water concentration of 1 ppm or less. For sealing, a glass sealing cap and the film-forming substrate epoxy type ultraviolet curable resin (manufactured by Nagase ChemteX Corporation) were used.

A direct current was applied to the organic electroluminescent device manufactured as described above, and the light emission characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON. As the light emission characteristics, the voltage (V) and the current efficiency (cd / A) when a current density of 10 mA / cm ² was passed were measured, and the element life (h) at the time of continuous lighting was measured. The element life (h) in Table 1 measures the luminance decay time during continuous lighting when the ^{manufactured element is driven at an initial luminance of 1000 cd / m 2 , until the luminance (cd / m 2} ) is reduced by 10%. The time required for was measured. The voltage, current efficiency, and element life are shown as relative values using the result in element reference example 2 described later as a reference value (100). The results are shown in Table 3.

Element Example 4
In the element Example 3, 4,6-diphenyl-2- [2'-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl synthesized in Example-2 instead of compound A-41. ] -1,3,5-Triazine (Compound A-421) was used, but an organic electric field light emitting device was prepared and evaluated by the same method as in Device Example 3. The results are shown in Table 3. The element life was expressed as a relative value with the element life of the element reference example 2 as 100 after measuring the element life (h).

Element reference example 2
In Device Example 3, 2- [5- (9-phenanthril) -4'-(2-pyrimidyl) biphenyl-3-yl] -4 described in JP-A-2011-063584 instead of compound A-41. , 6-Diphenyl-1,3,5-triazine (ETL-1) was used, but an organic electroluminescent device was prepared and evaluated by the same method as in Device Example 3. The results are shown in Table 3. Regarding the element life, after measuring the element life (h), the element life of this element reference example 2 was set as a reference value (100).

The triazine compound (1) of the present invention has excellent heat resistance of the film quality, and by using the compound, an organic electroluminescent element having excellent long life and luminous efficiency can be provided.

Further, the triazine compound (1) of the present invention is used as an electron transport material for an organic electroluminescent device having an excellent low driving voltage. Further, according to the present invention, it is possible to provide an organic electroluminescent device having excellent power consumption.

Further, the triazine compound of the present invention is excellent in operability of sublimation purification because it has good thermal stability during sublimation purification, and can provide a material having few impurities which causes deterioration of the organic electroluminescent element. Further, the triazine compound of the present invention can provide an organic electroluminescent device having a long life because the vapor deposition film is excellent in stability.

Further, the thin film made of the triazine compound (1) of the present invention is useful as a material for an organic electroluminescent element because it is excellent in electron transport ability, hole blocking ability, redox resistance, water resistance, oxygen resistance, electron injection characteristics and the like. It is useful as an electron transport material, a hole block material, a light emitting host material, and the like. It is especially useful when used with electron transport materials. Further, since the triazine compound (1) of the present invention is a wide bandgap compound, it can be suitably used not only for conventional fluorescent device applications but also for phosphorescent devices.

Claims (18)

A triazine compound represented by the general formula (1).

(In general formula (1),
Ar ¹ is phenyl, or naphthyl group (these groups, a fluorine atom, a methyl group, or may be substituted by a phenyl group) represent the two Ar ¹ are identical.
Ar ^2, and A r ⁵ are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, a fluoranthenyl group, triphenylenyl group, triazyl , Pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group (these groups are phenyl group, trill group, pyridyl group, methylpyridyl group, It may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms) , or represents a single bond.
Ar ³ and Ar ⁶ represent a single bond.
Ar ⁴ and Ar ⁷ independently have a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a peryleneyl group, a fluoranthenyl group, a triphenylenyl group and a triazil group. Pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (these groups are a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms. It may have an alkoxy group having 1 to 4 carbon atoms) .
Ar ^2, the total number of ring-constituting carbon atoms及beauty Ar ^4, and Ar ^5, the total number of ring-constituting carbon atoms及beauty Ar ⁷ are all 5-25.
A represents a single bond.
B ¹ and B ² represent a single bond or a hydrogen atom. However, ^{either B 1} or B ² represents a single bond to form a single bond with A, and the other represents a hydrogen atom.
Z ¹ and Z ² each independently represent a nitrogen atom or CH. However, ^{either Z 1} or Z ² represents a nitrogen atom, and the other represents CH. )
However, triazine compounds represented by the following formulas are excluded.

A triazine compound represented by the general formula (1).

(In general formula (1),
Ar ¹ Represents a phenyl group, a naphthyl group, or a biphenyl group, and two Ars ¹ Are the same.
Ar ² , And Ar ⁵ Independently, (a) a single ring or a condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, and (b) a monocyclic or condensed ring nitrogen-containing heteroaromatic aromatic group having only a 6-membered ring and having 3 to 25 carbon atoms. Represents a monocyclic or condensate heteroaromatic group having 3 to 25 carbon atoms, or a single bond, which is composed of an atom selected from the group of atoms consisting of a group group, (c) H, C, O, and S.
Ar ³ , And Ar ⁶ Represents a single bond.
Ar ⁴ , And Ar ⁷ Independently, (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, and (b) a monocyclic or condensed ring nitrogen-containing heteroaromatic group having only a 6-membered ring and having 3 to 25 carbon atoms. It represents a group group or a monocyclic or condensed ring heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the atomic group consisting of (c) H, C, O, and S.
Ar ² , And Ar ⁴ Total number of ring-constituting carbon atoms, and Ar ⁵ , And Ar ⁷ The total number of ring-constituting carbon atoms in each is 5 to 25.
A represents a single bond.
B ¹ And B ² Represents a single bond or a hydrogen atom. However, B ¹ Or B ² One of them represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.
Z ¹ And Z ² Independently represent a nitrogen atom or CH. However, Z ¹ Or Z ² One of them represents a nitrogen atom and the other represents CH. )
However, triazine compounds represented by the following formulas are excluded.

Ar ¹ is a phenyl group, or represents a biphenyl group, a triazine compound according to claim 2 two Ar ¹ are identical. The triazine compound according to claim 2 , wherein Ar ¹ is a phenyl group. Ar ² and ^{Ar 5} are independently composed of (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, and (b') a single ring having 3 to 11 carbon atoms having only a 6-membered ring. Ring or condensate nitrogen-containing heteroaromatic group, (c) monocyclic or condensate heteroaromatic group having 3 to 25 carbon atoms composed of atoms selected from the atomic group consisting of H, C, O, and S. Alternatively, it is a single bond, and Ar ⁴ and Ar ⁷ each independently consist of (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, and (b') a 6-membered ring. A monocyclic or hydrocarbon-containing heteroaromatic group having 3 to 11 carbon atoms, or (c) a monocyclic ring having 3 to 25 carbon atoms composed of atoms selected from the atomic group consisting of H, C, O, and S. Alternatively, the triazine compound according to any one of claims 2 to 4, which is a condensed ring heteroaromatic group. Ar ^2, and A r ^5, each independently, a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, a fluoranthenyl group, triphenylenyl group, triazyl , Pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, or single bond, and Ar ⁴ and Ar ⁷ are independent of each other. Phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, peryleneyl group, fluoranthenyl group, triphenylenyl group, triazil group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl. The triazine compound according to any one of claims 2 to 4, which is a group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group. Ar ^2, and A r ^5, each independently, a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, a fluoranthenyl group, triphenylenyl group, triazyl , Pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, or single bond, and Ar ⁴ and Ar ⁷ are independent of each other. Phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, peryleneyl group, fluoranthenyl group, triphenylenyl group, triazil group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl. The triazine compound according to any one of claims 1 to 4, wherein the group is a group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group. -Ar ² -A r ^4, a group represented by and ^-Ar is 5 -A group represented by ^{r 7,} each independently, a phenyl group, a biphenyl group, naphthyl phenyl group, phenanthryl phenyl group, fluoran Tenylphenyl group, pyridylphenyl group, pyrimidylphenyl group, quinolylphenyl group, thienylphenyl group, frillphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienyl Phenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl group, or dibenzo The triazine compound according to any one of claims 1 to 4, which is a frill group. A group represented by -Ar ² -A r ^4, and groups represented by ^-Ar 5 -A ^{r 7} are each independently a phenyl group, a biphenyl group, naphthyl phenyl group, phenanthryl phenyl, pyridylphenyl Group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl The triazine compound according to any one of claims 1 to 4, which is a group, a phenylantril group, a dibenzothienyl group, or a dibenzofuryl group. -Ar ² -A r ^4, a group represented by or ^-Ar 5 -A ^r either of the groups represented by ⁷ is a phenyl group, a biphenyl group, naphthyl phenyl group, phenanthryl phenyl, pyridylphenyl Group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl A group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group), and the other is a phenyl group, a biphenyl group, a pyridyl group, or a group. The triazine compound according to any one of claims 1 to 4, which is a naphthyl group. -Ar ² -A r ^4, a group represented by or ^-Ar 5 -A ^r either of the groups represented by ⁷ is a phenyl group, a biphenyl group, naphthyl phenyl group, phenanthryl phenyl, pyridylphenyl Group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl The triazine compound according to any one of claims 1 to 4, wherein the group is a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group, and the other is a phenyl group or a naphthyl group. A triazine compound represented by the general formula (1).

(In general formula (1),
Ar ¹ Represents a phenyl group or a biphenyl group, and two Ars ¹ Are the same,
Ar ³ , And Ar ⁶ Represents a single bond
-Ar ² -Ar ⁴ Group represented by, or -Ar ⁵ -Ar ⁷ One of the groups represented by is phenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienyl. Phenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, phenanthryl group, dibenzothienyl group, or dibenzofuryl group, the other is a phenyl group. , Or a naphthyl group.
A represents a single bond.
B ¹ And B ² Represents a single bond or a hydrogen atom. However, B ¹ Or B ² One of them represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.
Z ¹ And Z ² Independently represent a nitrogen atom or CH. However, Z ¹ Or Z ² One of them represents a nitrogen atom and the other represents CH. )
However, triazine compounds represented by the following formulas are excluded.

A triazine compound represented by the general formula (1).

(In general formula (1),
Ar ¹ Represents a phenyl group
Ar ³ , And Ar ⁶ Represents a single bond
-Ar ² -Ar ⁴ Group represented by, or -Ar ⁵ -Ar ⁷ One of the groups represented by is phenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienyl. Phenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, phenanthryl group, dibenzothienyl group, or dibenzofuryl group, the other is a phenyl group. , Or a naphthyl group.
A represents a single bond.
B ¹ And B ² Represents a single bond or a hydrogen atom. However, B ¹ Or B ² One of them represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.
Z ¹ And Z ² Independently represent a nitrogen atom or CH. However, Z ¹ Or Z ² One of them represents a nitrogen atom and the other represents CH. )
However, triazine compounds represented by the following formulas are excluded.

A triazine compound represented by the general formula (1).

(In general formula (1),
Ar ¹ Represents a phenyl group
Ar ² , And Ar ⁵ Represents a single bond or a phenylene group
Ar ³ , And Ar ⁶ Represents a single bond
Ar ⁴ , And Ar ⁷ Represents a phenyl group, a pyridyl group, a naphthyl group, or a dibenzofuryl group.
A represents a single bond.
B ¹ And B ² Represents a single bond or a hydrogen atom. However, B ¹ Or B ² One of them represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.
Z ¹ And Z ² Independently represent a nitrogen atom or CH. However, Z ¹ Or Z ² One of them represents a nitrogen atom and the other represents CH. )
However, triazine compounds represented by the following formulas are excluded.

A triazine compound represented by the general formula (1).

(In general formula (1),
Ar ¹ Represents a phenyl group or a biphenyl group, and two Ars ¹ Are the same,
Ar ² Represents a single bond or a phenylene group
Ar ³ , Ar ⁵ , And Ar ⁶ Represents a single bond
Ar ⁴ , And Ar ⁷ Represents a phenyl group, a pyridyl group, a naphthyl group, or a dibenzofuryl group.
A represents a single bond.
B ¹ And B ² Represents a single bond or a hydrogen atom. However, B ¹ Or B ² One of them represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.
Z ¹ And Z ² Independently represent a nitrogen atom or CH. However, Z ¹ Or Z ² One of them represents a nitrogen atom and the other represents CH. )
However, triazine compounds represented by the following formulas are excluded.

The method for producing a triazine compound according to any one of claims 1 to 15.
Producing how features and to belt triazine compound utilizing coupling reaction. Triazine compound according to any one of claims 1 to 15, an organic electroluminescent device timber fees. Triazine compound according to any one of claims 1 to 15, an electron-transporting materials for organic electroluminescent devices.

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