JP6500644B2 - Triazine compound, method for producing the same, and use thereof - Google Patents

Description

  The present invention relates to a triazine compound, a method for producing the same, and an organic electroluminescent device containing the same. More specifically, the present invention relates to a triazine compound useful as a material for an organic electroluminescent device characterized by a structure in which a diaryl pyridyl group is combined with a triazine skeleton, and a method for producing the same, using the triazine compound in at least one layer of an organic compound layer The present invention relates to a high efficiency, low voltage and high durability organic electroluminescent device.

  The organic electroluminescent device has a light emitting layer containing a light emitting material sandwiched between a hole transporting layer and an electron transporting layer, and further has an anode and a cathode attached to the outside as a basic configuration, and holes injected into the light emitting layer And light emitting elements that use light emission (fluorescence or phosphorescence) when excitons generated by electron recombination are deactivated (fluorescence or phosphorescence), and are already used for applications such as large televisions and lighting as well as small displays . 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. There are also cases where it is divided. In addition, as a carrier transport layer (electron transport layer or hole transport layer) of the organic electroluminescent device, a co-evaporated film doped with a metal, an organic metal compound or another organic compound may be used.

  Conventional organic electroluminescent devices have a higher driving voltage than inorganic light emitting diodes, low light emission luminance and luminous efficiency, extremely low device lifetimes, and have not been put into practical use. Although recent organic electroluminescent devices have been gradually improved, more excellent materials are required in light emission efficiency characteristics, drive voltage characteristics and long life characteristics. Furthermore, depending on applications such as in-vehicle applications, high heat resistance may be required, and materials are required to have a high glass transition temperature (Tg).

  As an electron transport material which is excellent in the long life property for organic electroluminescent elements, the triazine compound disclosed by patent document 1 is mentioned. However, further improvement has been required in terms of voltage, lifetime and luminous efficiency of organic electroluminescent devices using the materials.

  Patent Document 2 discloses a triazine compound represented by Compound 4-12. The compound is excellent in enhancing the light emission efficiency of the organic electroluminescent device, but further improvement of the light emission efficiency has been desired.

JP, 2011-063584, A KR10-2013-0128322

  An object of the present invention is to provide an electron transporting material which is excellent in heat resistance of film quality and excellent in long life, low voltage drivability or luminous efficiency of an organic electroluminescent device.

  The inventors of the present invention conducted intensive studies to solve the above problems, and as a result, the heat resistance of the film quality of a triazine compound to which a diaryl pyridyl group to be described later is bonded is high, and organic electroluminescence using the compound as an electron transport material It has been found that the device can achieve lower voltage, longer lifetime, or higher luminous efficiency as compared with the case of using a conventionally known material, and the present invention has been completed.

  That is, the present invention provides the following general formula (11)

(In the general formula (11),
Ar ¹ each independently represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group).
Ar ² and Ar ³ each independently represent an aromatic hydrocarbon group which may be linked and / or fused with 6 to 24 carbon atoms, a 3 to 25 carbon linkage composed only of 6-membered rings, and And / or a nitrogen-containing heteroaromatic group which may be fused, or a linked and / or fused ring having 3 to 25 carbon atoms which is composed of an atom selected from the group consisting of H, C, O, and S A heteroaromatic group which may be substituted (these groups may be substituted with a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).
Each of R ⁵ , R ⁶ and R ⁷ independently represents an alkyl group having 1 to 4 carbon atoms. p represents 0, 1, 2, 3 or 4; When p is 2, 3 or 4, R ⁵ may be different from each other. q represents 0, 1, 2, 3 or 4; When q is 2, 3 or 4, R ⁶ may be different from each other. r represents 0, 1 or 2; When r is 2, two R ⁷ may be different from each other.
Z ¹ and Z ² each independently represent a nitrogen atom or C—H. However, either ^one of Z ¹ or Z ² represents a nitrogen atom, and the other represents C—H. )
Or a triazine compound (hereinafter also referred to as a triazine compound (11)), preferably a compound represented by the following general formula (1):

(In the general formula (1),
Ar ¹ each independently represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group).
Ar ² is an aromatic hydrocarbon group which may be linked and / or fused, having 6 to 24 carbon atoms, and has a carbon number of 3 to 25 composed of only a 6-membered ring and / or fused Or a heteroaromatic group having 3 to 25 carbon atoms which may be linked and / or condensed, which is composed of an atom selected from the group consisting of H, C, O, and S. A group (these groups may be substituted with a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).
Ar ³ is a C 10-24 linked and / or fused aromatic hydrocarbon group, a C 3-25 linked and / or fused ring composed of only six-membered rings, Or a heteroaromatic group having 3 to 25 carbon atoms which may be linked and / or condensed, which is composed of an atom selected from the group consisting of H, C, O, and S. A group (these groups may be substituted with a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).
Z ¹ and Z ² each independently represent a nitrogen atom or C—H. However, either ^one of Z ¹ or Z ² represents a nitrogen atom, and the other represents C—H. )
The present invention relates to a triazine compound (hereinafter, also referred to as triazine compound (1)), a method for producing the compound, and a material for an organic electroluminescent device using the compound.

  Hereinafter, the present invention will be described in detail.

  The present invention relates to providing the above-mentioned triazine compound (11) or (1), a method for producing them, and a material for an organic electroluminescent device containing the compound.

  Substituents in the triazine compounds (11) and (1) of the present invention are defined as follows.

In the general formulas (11) and (1), Ar ¹ each independently represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group). .

The phenyl group substituted by a fluorine atom in Ar ¹ or the naphthyl group is not particularly limited, but fluorophenyl group, pentafluorophenyl group, difluorophenyl group, fluoronaphthyl group, difluoronaphthyl group, etc. Preferred examples are given.

The methyl group-substituted phenyl group or naphthyl group in Ar ¹ is not particularly limited, but preferred examples thereof include a tolyl group, a methylnaphthyl group, a dimethylphenyl group, and a dimethylnaphthyl group.

The phenyl group substituted by a phenyl group or a naphthyl group in Ar ¹ is not particularly limited, but a biphenyl group, a phenylnaphthyl group, a terphenyl group, a diphenylnaphthyl group and the like are mentioned as preferable examples.

Ar ¹ is more preferably independently a phenyl group, a naphthyl group or a biphenyl group from the viewpoint of excellent electron transporting material properties, and is more preferably a phenyl group from the viewpoint of easy synthesis.

Specific examples of Ar ¹ include, but are not limited to, phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, Mesityl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,4-difluorophenyl group, 3,5-difluorophenyl group, biphenyl-
2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 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- 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 ′, '-Trimethylbiphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalen-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalen-4-yl group, 1-phenylnaphthalen-5-yl group, 1-phenylnaphthalen-6-yl group, 1-phenylnaphthalen-7-yl group, 1-phenylnaphthalen-8-yl group, 2-phenylnaphthalen-1-yl group, 2-phenylnaphthalen-3-yl group, 2-phenylnaphthalen-4-yl group, 2-phenylnaphthalen-5-yl group, 2-phenylnaphthalen-6-yl group, 2-phenylnaphthalen-7-yl group, 2-phenylnaphthalen-8-yl group, 1-methylnaphthalen-4-yl group, 1-methylnaphthalen-5-yl group, 1-methylnaphthalene-6 1-methylnaphthalen-7-yl group, 1-methylnaphthalen-8-yl group, 2-methylnaphthalen-1-yl group, 2-methylnaphthalen-3-yl group, 2-methylnaphthalene-4-yl group And 2-methylnaphthalen-6-yl group, 2-methylnaphthalen-7-yl group, 2-methylnaphthalen-7-yl group, and 2-methylnaphthalen-8-yl group are preferred examples. . 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 is preferable in that it has 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.

In formulas (11) and (1), ^one of Z ¹ and Z ² represents a nitrogen atom, and the other represents C—H.

In General Formula (11), Ar ² and Ar ³ each independently represent an aromatic hydrocarbon group which may be linked and / or fused with 6 to 24 carbon atoms, or a carbon consisting of only a 6-membered ring A carbon number of 3 to 25 composed of an atom selected from the group consisting of a nitrogen-containing heteroaromatic group which may be linked and / or fused and a number 3 to 25 or H, C, O and S Heteroaromatic groups which may be linked and / or fused (these groups may be substituted with a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms) Represents

In the general formula (11), Ar ² and Ar ³ may be the same or different.

The aromatic hydrocarbon group which may be linked and / or fused and having 6 to 24 carbon atoms in Ar ² and Ar ³ is not particularly limited, and a phenyl group, a biphenyl group, a terphenyl group, Quaternary phenyl, naphthylphenyl, phenanthrylphenyl, anthrylphenyl, pyrenylphenyl, triphenylphenyl, chrysenylphenyl, fluoranthenylphenyl, acenaphthylphenyl, fluorenylphenyl Group, naphthyl biphenyl group, naphthyl group, phenyl naphthyl group, biphenyl naphthyl group, phenanthryl naphthyl group, anthryl naphthyl group, phenanthryl group, phenyl phenanthryl group, naphthyl phenanthryl group, anthryl group, phenyl anthryl group , Naphthyl anthryl group, pyrenyl group Phenylpyrenyl group, triphenylenyl group, phenyltriphenylenyl group, chrysenyl group, phenylchrysenyl group, fluoranthenyl group, phenylfluoranthenyl group, acenaphthyl group, phenylacenaphthyl group, fluorenyl group, phenylfluorenyl group Or a benzofluorenyl group etc. is mentioned as a preferable example. These substituents may be substituted by a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

The nitrogen-containing heteroaromatic group which may be linked and / or fused and having 3 to 25 carbon atoms and which is composed of only a 6-membered ring in Ar ² and Ar ³ is not particularly limited, but is pyridyl Group, pyrazyl group, pyrimidyl group, pyridazyl group, triazyl group, quinolyl group, isoquinolyl group, phenanthridyl group, benzoquinolyl group, acridinyl group, pyridylphenyl group, pyrazylphenyl group, pyrimidylphenyl group, pyridazylphenyl group Group, triazyl phenyl group, quinolyl phenyl group, isoquinolyl phenyl group, phenanthridyl phenyl group, benzoquinolyl phenyl group, acridinyl phenyl group, (phenyl pyridyl) phenyl group, (naphthyl pyridyl) phenyl group, Pyridyl biphenyl group, pyrazyl biphenyl group, pyrimidyl biphenyl group, Dazyl biphenyl group, triazyl biphenyl group, quinolyl biphenyl group, isoquinolyl biphenyl group, phenanthridyl biphenyl group, benzoquinolyl biphenyl group, acridinyl biphenyl group, pyridyl terphenyl group, pyrazyl terphenyl group, Pyrimidyl terphenyl group, pyridazir terphenyl group, triazyl terphenyl group, pyridylnaphthyl group, pyrazyl naphthyl group, pyrimidyl naphthyl group, pyridazyl naphthyl group, triazyl naphthyl group, quinolyl naphthyl group, isoquino Lylnaphthyl group, phenanthridyl naphthyl group, benzoquinolyl naphthyl group, acridinyl naphthyl group, phenyl pyridyl group, biphenyl pyridyl group, naphthyl pyridyl group, phenanthryl pyridyl group, anthryl pyridyl group, pyrenyl pyridyl group, triflic Preferred examples include a phenenyl pyridyl group, a chrysenyl pyridyl group, a fluoranthenyl pyridyl group, an acenaphthyl pyridyl group, a fluorenyl pyridyl group and the like. These substituents may be substituted by a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

As the heteroaromatic group which may be linked and / or fused, having 3 to 25 carbon atoms, which is composed of an atom selected from the group consisting of H, C, O, and S in Ar ² and Ar ³ , Although not particularly limited, thienyl group, furyl group, bithienyl group, bifuryl group, benzothienyl group, benzofuryl group, dibenzothienyl group, dibenzofuryl group, thienylphenyl group, furylphenyl group, bithienylphenyl group, biphenyl Furylphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, thienylbiphenyl group, furylbiphenyl group, benzothienylbiphenyl group, benzofurylbiphenyl group, dibenzothienylbiphenyl group, dibenzofurylbiphenyl group Group, thienylnaphthyl group, Lylnaphthyl group, benzothienylnaphthyl group, benzofurylnaphthyl group, dibenzothienylnaphthyl group, dibenzofurylnaphthyl group, phenylthienyl group, phenylfuryl group, biphenylthienyl group, biphenylfuryl group, naphthylthienyl group, naphthylfuryl group, phenanthryl group Thienyl group, phenanthryl furyl group, anthryl thienyl group, anthryl furyl group, pyrenyl thienyl group, pyrenyl furyl group, triphenylenyl thienyl group, triphenylenyl furyl group, chrysenyl thienyl group, chrysenyl furyl group, fluoranthenyl thienyl Preferred examples include a group, a fluoranthenylfuryl group, an acenaphthylthienyl group, an acenaphthylfuryl group, a fluorenylthienyl group, or a fluorenylfuryl group. These substituents may be substituted by a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

The alkyl group having 1 to 4 carbon atoms in Ar ² and Ar ³ is not particularly limited, but methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, t-butyl group etc. are preferable. An example is given.

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

The fluorine atom-substituted monocyclic or condensed aromatic hydrocarbon group having 6 to 18 carbon atoms in Ar ² and Ar ³ is not particularly limited, and a fluorophenyl group, a pentafluorophenyl group, Fluorobiphenyl group, fluoroterphenyl group, fluoroquaternary phenyl group, fluoronaphthylphenyl group, naphthylfluorophenyl group, fluorophenanthrylphenyl group, phenanthrylfluorophenyl group, fluoroanthrylphenyl group, anthryl fluorophenyl group, Fluoropyrenylphenyl group, pyrenyl fluorophenyl group, fluorotriphenylphenyl group, triphenylfluorophenyl group, fluorochrysenylphenyl group, chrysenyl fluorophenyl group, fluorofluoranthenylphenyl group, fluoro N-fluorophenyl group, fluoroacenaphthylphenyl group, acenaphthyl fluorophenyl group, fluorofluorenylphenyl group, fluorenyl fluorophenyl group, fluoronaphthylbiphenyl group, naphthylfluorobiphenyl group, fluoronaphthyl group, fluorophenyl naphthyl group, Phenyl fluoronaphthyl group, fluorobiphenyl naphthyl group, biphenyl fluoronaphthyl group, fluorophenanthrylnaphthyl group, phenanthryl fluoronaphthyl group, fluoroanthrylnaphthyl group, anthryl fluoronaphthyl group, fluorophenanthryl group, fluorophenyl phenyl group Nantolyl group, phenylfluorophenanthryl group, fluoronaphthylphenanthryl group, naphthylfluorophenanthryl group, fluoroanthryl group, full Orophenylanthryl group, phenyl fluoroanthryl group, fluoronaphthyl anthryl group, naphthyl fluoro anthryl group, fluoro pyrenyl group, fluoro phenyl pyrenyl group, phenyl fluoro pyrenyl group, fluoro triphenylenyl group, fluoro phenyl triphenylenyl Group, phenyl fluoro triphenyl group, fluoro chrysenyl group, fluoro phenyl chrysenyl group, phenyl fluoro chrysenyl group, fluoro fluoranthenyl group, fluoro phenyl fluoranthenyl group, phenyl fluoro fluoranthenyl group, fluoro Acenaphthyl group, fluorophenylacenaphthyl group, phenylfluoroacenaphthyl group, fluorofluorenyl group, fluorophenylfluorenyl group, phenylfluorofluorenyl group or fluoroben Fluorenyl group and the like as a preferable example.

Ar ² and Ar ³ are each independently composed of only an aromatic hydrocarbon group having 6 to 24 carbon atoms which may be linked and / or fused, and a 6-membered ring, from the viewpoint of excellent electron transporting material properties The carbon number 3 composed of an atom selected from the group consisting of a nitrogen-containing heteroaromatic group which may be linked and / or a condensed 3 to 25 carbon atoms, or H, C, O, and S It is preferable that they are heteroaromatic groups (these groups may be substituted by a C1-C4 alkyl group) which may be linked and / or fused 25 to 25.

  Specifically, each of them is independently phenyl, biphenyl, naphthylphenyl, phenanthrylphenyl, fluoranthenylphenyl, pyridylphenyl, quinolylphenyl, thienylphenyl, furylphenyl, benzothienyl Phenyl group, benzofuryl phenyl group, dibenzothienyl phenyl group, dibenzofuryl phenyl group, naphthyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl group, or dibenzofuryl group (these groups are fluorine atoms Or optionally substituted with a methyl group).

Ar ² and Ar ³ each further independently represent an aromatic hydrocarbon group which may be linked and / or fused with 6 to 24 carbon atoms, or 3 to 25 carbon atoms composed of only a 6-membered ring A nitrogen-containing heteroaromatic group which may be linked and / or fused, or a C3-C25 linkage and / or condensation composed of an atom selected from the group consisting of H, C, O, and S More preferably, it is a heteroaromatic group which may be cyclic.

Specifically, each of them is independently phenyl, biphenyl, naphthylphenyl, phenanthrylphenyl, fluoranthenylphenyl, pyridylphenyl, quinolylphenyl, thienylphenyl, furylphenyl, benzothienyl Phenyl, benzofurylphenyl, dibenzothienylphenyl, dibenzofurylphenyl, naphthyl, benzothienyl, benzofuryl, phenanthryl, anthryl, dibenzothienyl or dibenzofuryl is more preferable, and phenyl is more preferable. More preferably, they are a group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a pyridylphenyl group, a dibenzothienylphenyl group, a dibenzofurylphenyl group, a naphthyl group or a phenanthryl group.

Ar ² And Ar ³ As specific examples of is not particularly limited, phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, mesityl group , 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,4-diethylphenyl, 3,5-diethylphenyl, 2-propylphenyl, 3-propylphenyl, 4-propyl Phenyl, 2,4-dipropylphenyl, 3,5-dipropylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 2,4-diisopropylphenyl, 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'- bird Tylbiphenyl-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, 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'-propylbiphenyl-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, 6-isopropylbiphenyl-3-yl, 4'-isopropylbiphenyl-3-yl, 5-isopropylbiphenyl-2-yl, 4'-isopropylbiphenyl-2-yl, 2 ', 4 ', 6'-triisopropylbiphenyl-2-yl group, 3-butylbiphenyl-4-yl group, 4'-butylbiphenyl-4-yl group, 2', 4 ', 6'-tributylbiphenyl-4- Group, 6-butylbiphenyl-3-yl group, 4'-butylbiphenyl-3-yl group, 5-butylbiphenyl-2-yl 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-butyl group Biphenyl-4-yl group, 6-tert-butylbiphenyl-3-yl group, 4′-tert-butylbiphenyl-3-yl group, 5-tert-butylbiphenyl-2-yl group, 4′-tert-butyl group Biphenyl-2-yl group
, 2 ', 4', 6'- tri tert- butyl biphenyl -2- yl group, 2- pyridyl group, 3- pyridyl group, 4- pyridyl group, 2- methyl pyridin 3- yl group, 2- methyl pyridine 4-yl group, 2-methylpyridin-5-yl group, 2-methylpyridin-6-yl group, 3-methylpyridin-2-yl group, 3-methylpyridin-4-yl group, 3-methylpyridine -5-yl group, 3-methylpyridin-6-yl group, 4-methylpyridin-2-yl group, 4-methylpyridin-3-yl group, 2,6-dimethylpyridin-3-yl group, 2 ,, 6-dimethylpyridin-4-yl group, 3,6-dimethylpyridin-2-yl group, 3,6-dimethylpyridin-4-yl group, 3,6-dimethylpyridin-5-yl group, 2-phenylpyridine -6-yl group, 3-phenylpi Gin-6-yl group, 4-phenylpyridin-6-yl group, 5-phenylpyridin-6-yl group, 2-phenylpyridin-3-yl group, 2-phenylpyridin-5-yl group, 3-phenyl Pyridin-5-yl group, 4-phenylpyridin-3-yl group, 3-phenylpyridin-4-yl group, 2-phenylpyridin-4-yl group, 2- (2-pyridyl) phenyl group, 3- ( 2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 2- (3-pyridyl) phenyl group, 3- (3-pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 2- (2- (3-pyridyl) phenyl group) 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-phenyl group 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) group ) 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-) 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- (2,2, 4-dimethyl-3-pyridyl) phenyl group, -(2,4-dimethyl-3-pyridyl) phenyl group, 2- (3,5-dimethyl-4-pyridyl) phenyl group, 3- (3,5-dimethyl-4-pyridyl) phenyl group, 4- (4- 3,5-Dimethyl-4-pyridyl) phenyl, 2- (3-phenyl-2-pyridyl) phenyl, 3- (3-phenyl-2-pyridyl) phenyl, 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-pyridyl) phenyl group, 2- (4- (4-phenyl-2-pyridyl) phenyl group) 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- (3 -Phenyl-2-pyridyl) phenyl group, 4- (6-phenyl-2-pyridyl) phenyl group, 2- (2-phenyl-3-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) group -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) group -
Lysyl) 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-phenyl) group 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-phenanthryl) phenyl group, 3- (1-phenanthryl) phenyl group, 4- (1-) Phenanthryl) phenyl group, 2- (2-phenanthryl) phenyl group, 3- (2-phenanthryl) phenyl group, 4- (2-phenanthryl) phenyl group, 2- (3-phenanthryl) phenyl group, 3- (3- (3-phenethyl) phenyl group Phenanthryl) phenyl group, 4- (3-phenanthryl) phenyl group, 2- (4-phenanthryl) phenyl group, 3- (4-phenanthryl) phenyl group, 4- (4-phenanthryl) phenyl group, 2- (9-) Phenanthryl) phenyl group, 3- (9-phenanthryl) phenyl group, 4- (9-phenanthryl) phenyl group, 2- (1 Anthryl) phenyl group, 3- (1-anthryl) phenyl group, 4- (1-anthryl) phenyl group, 2- (2-anthryl) phenyl group, 3- (2-anthryl) phenyl group, 4- (2- (2-anthryl) phenyl group) 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- (1-pyrenyl) phenyl group 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-pyrene) phenyl group Pyrenyl) phenyl group, 3- (4-pyrenyl) phenyl group, 4- (4-pyrenyl) phenyl group, 2- (fluoranten-1-yl) phenyl group, 3- (fluoranten-1-yl) pheny Group, 4- (fluoranthene-1-yl) phenyl group, 2- (fluoranthene-2-yl) phenyl group, 3- (fluoranthene-2-yl) phenyl group, 4- (fluoranthene-2-yl) phenyl group , 2- (fluoranthene-3-yl) phenyl group, 3- (fluoranthene-3-yl) phenyl group, 4- (fluoranthene-3-yl) phenyl group, 2- (fluoranthene-4-yl) phenyl group, 3 -(Fluoranthene-4-yl) phenyl group, 4- (fluoranthene-4-yl) phenyl group, 2- (fluoranthene-5-yl) phenyl group, 3- (fluoranthene-5-yl) phenyl group, 4- (fluoranthene-5-yl) phenyl group Fluoranthen-5-yl) phenyl group, 2- (triphenylene-1-yl) phenyl group, 3- (triphenylene-1-yl) phenyl group, -(Triphenylene-1-yl) phenyl group, 2- (triphenylene-2-yl) phenyl group, 3- (triphenylene-2-yl) phenyl group, 4- (triphenylene-2-yl) phenyl group, 2- ( Chrysen-1-yl) phenyl group, 3- (chrysen-1-yl) phenyl group, 4- (chrysen-1-yl) phenyl group, 2- (chrysen-2-yl) phenyl group, 3- (chrysene- 2-yl) phenyl group, 4- (chrysen-2-yl) phenyl group, 2- (chrysen-3-yl) phenyl group, 3- (chrysen-3-yl) phenyl group, 4- (chrysene-3-yl) Yl) phenyl group, 2- (chrysen-4-yl) phenyl group, 3- (chrysen-4-yl) phenyl group, 4- (chrysen-4-yl) phenyl group, 2- (chrysen-5-yl) Phenyl , 3- (chrysen-5-yl) phenyl group, 4- (chrysen-5-yl) phenyl group, 2- (chrysen-6-yl) phenyl group, 3- (chrysen-6-yl) phenyl group, 4 -(Chrysen-6-yl) phenyl group, 2- (acenaphthylene-1-yl) phenyl group, 3- (acenaphthylene-1-yl) phenyl group, 4- (acenaphthylene-1-yl) phenyl group, 2- (acenaphtylene-1-yl) phenyl group Acenaphthyl-3-yl) phenyl, 3- (acenaphthyl-3-yl) phenyl, 4- (acenaphthyl-3-yl) phenyl, 2- (acenaphthyl-4-yl) phenyl, 3- (acenaphthylene-) 4-yl) phenyl, 4- (acenaphthyl-4-phenyl) phenyl, 2- (acenaphthyl-5-yl) phenyl, 3- (acenaphthyl-5-yl) phenyl
-Phenyl group, 4- (acenaphthyl-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-3-yl) phenyl group, 2- (fluoren-4-yl) phenyl group, 3- (fluoren-4-yl) phenyl group, 4- (fluoren-4-yl) phenyl group Fluoren-4-yl) phenyl group, 2- (pyrimidin-2-yl) phenyl group, 3- (pyrimidin-2-yl) phenyl group, 4- (pyrimidin-2-yl) phenyl group, 2- (pyrimidin-2-yl) phenyl group; 4- (pyrimidin-4-yl) phenyl, 4- (pyrimidin-4-yl) phenyl, 2- (pyrimidin-5-yl) phenyl, 3- (pyrimidin-) 5-yl) phenyl group, 4- (pyrimidin-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) f 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 Isoquinolyl) phenyl group, 4- (4-isoquinolyl) phenyl group, 2- (5-isoquinolyl) phenyl group, 3- (5-isoquinolyl) phenyl group, 4- (5-isoquinolyl) phenyl group , 2- (6-isoquinolyl) phenyl group, 3- (6-isoquinolyl) phenyl group, 4- (6-isoquinolyl) phenyl group, 2- (7-isoquinolyl) phenyl group, 3- (7-isoquinolyl) phenyl group , 4- (7-isoquinolyl) phenyl group, 2- (8-isoquinolyl) phenyl group, 3- (8-isoquinolyl) phenyl group, 4- (8-isoquinolyl) phenyl group, 2- (phenanthridine-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- (phenanthridin-3-yl) phenyl group, 2- (phenanthridin-4-yl) phenyl group, 3- (phenanthridine) group -4-yl) phenyl group, 4- (phenanthridin-4-yl) phenyl group, 2- (phenanthridin-5-yl) phenyl group, 3- (phenanthridin-5-yl) phenyl group 4- (phenanthridin-5-yl) phenyl group, 2- (phenanthridine-6-yl) phenyl group, 3- (phenanthridin-6-yl) phenyl group, 4- (phenanthridine- 6-yl) phenyl group, 2- (phenanthridin-7-yl) phenyl group, 3- (phenanthridin-7-yl) phenyl group, 4- (phenanthridin-7-yl) phenyl group, 2 -(Phenanthridin-8-yl) phenyl group, 3- (phenanthridin-8-yl) phenyl group, 4- (phenanthridin-8-yl) phenyl group, 2- (phenanthridine-9-) Il) Pheny Group, 3- (phenanthridin-9-yl) phenyl group, 4- (phenanthridin-9-yl) phenyl group, 2- (phenanthridin-10-yl) phenyl group, 3- (phenanthridine) -10-yl) phenyl group, 4- (phenanthridin-10-yl) phenyl group, "" 2- (benzo [h] quinolin-2-yl) phenyl group, 3- (benzo [h] quinoline-2 -Yl) phenyl group, 4- (benzo [h] quinolin-2-yl) phenyl group, 2- (benzo [h] quinolin-3-yl) phenyl group, 3- (benzo [h] quinolin-3-yl ) Phenyl group, 4- (benzo [h] quinolin-3-yl) phenyl group, 2- (benzo [h] quinolin-4-yl) phenyl group, 3- (benzo [h] quinolin-4-yl) phenyl Group, 4- (benzo [h] quino
Phosphor-4-yl) phenyl group, 2- (benzo [h] quinolin-5-yl) phenyl group, 3- (benzo [h] quinolin-5-yl) phenyl group, 4- (benzo [h] quinoline- 5-yl) phenyl group, 2- (benzo [h] quinolin-6-yl) phenyl group, 3- (benzo [h] quinolin-6-yl) phenyl group, 4- (benzo [h] quinoline-6-4 Yl) phenyl group, 2- (benzo [h] quinolin-7-yl) phenyl group, 3- (benzo [h] quinolin-7-yl) phenyl group, 4- (benzo [h] quinolin-7-yl) group Phenyl group, 2- (benzo [h] quinolin-8-yl) phenyl group, 3- (benzo [h] quinolin-8-yl) phenyl group, 4- (benzo [h] quinolin-8-yl) phenyl group , 2- (benzo [h] quinolin-9-yl) Henyl group, 3- (benzo [h] quinolin-9-yl) phenyl group, 4- (benzo [h] quinolin-9-yl) phenyl group, 2- (benzo [h] quinolin-10-yl) phenyl group , 3- (benzo [h] quinolin-10-yl) phenyl group, 4- (benzo [h] quinolin-10-yl) phenyl group, 2- (acridin-1-yl) phenyl group, 3- (acridine- 1-yl) phenyl group, 4- (acridin-1-yl) phenyl group, 2- (acridin-2-yl) phenyl group, 3- (acridin-2-yl) phenyl group, 4- (acridin-2-yl group) ) Phenyl group, 2- (acridin-3-yl) phenyl group, 3- (acridin-3-yl) phenyl group, 4- (acridin-3-yl) phenyl group, 2- (acridin-4-yl) group Phenyl group 3- (acridin-4-yl) phenyl group, 4- (acridin-4-yl) phenyl group, 2- (acridin-9-yl) phenyl group, 3- (acridin-9-yl) phenyl group, 4- (acridin-9-yl) phenyl group (Acridin-9-yl) phenyl group, 2- (2-thienyl) phenyl group, 3- (2-thienyl) 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- (4-methylthiophen-2-yl) phenyl group Methylthiofe -2-yl) phenyl group, 2- (5-methylthiophen-2-yl) phenyl group, 3- (5-methylthiophen-2-yl) phenyl group, 4- (5-methylthiophen-2-yl) group ) Phenyl group, 2- (2-methylthiophen-3-yl) phenyl group, 3- (2-methylthiophen-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-methylthiophene) group Thiophene-3-yl) phenyl group, 3- (5-methylthiophen-3-yl) phenyl group, 4- (5-methylthiophen-3-yl) phenyl group, 2- (3-phenylthiophen-2-yl) group ) -Phenyl group, 3- (3-phenylthiophen-2-yl) phenyl group, 4- (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-phenylthiophene) -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-phenylthiophen-3-yl) phenyl group, 3- (4-phenylthiophene-) -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-furyl) phenyl group, 4- (2-furyl) phenyl group, 2- (3-furyl) phenyl group, 3- (3) -Furyl) phenyl group, 4- (3-furyl) 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-methyl) phenyl group
Tyrfuran-2-yl) phenyl group, 3- (5-methylfuran-2-yl) phenyl group, 4- (5-methylfuran-2-yl) phenyl group, 2- (2-methylfuran-3-yl group) ) 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-Methylfuran-3-yl) phenyl, 4- (4-methylfuran-3-yl) phenyl, 2- (5-methylfuran-3-yl) phenyl, 3- (5-methyl) Furan-3-yl) phenyl group, 4- (5-methylfuran-3-yl) phenyl group, 2- (3-phenylfuran-2-yl) phenyl group, 3- (3-phenylfuran-2-yl group ) Phenyl group, 4- (3-phenylfuran-2-) Y) phenyl group, 2- (4-phenylfuran-2-yl) phenyl group, 3- (4-phenylfuran-2-yl) phenyl group, 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- (2-phenylfuran-2-yl) phenyl group) Phenylfuran-3-yl) phenyl group, 3- (2-phenylfuran-3-yl) phenyl group, 4- (2-phenylfuran-3-yl) phenyl group, 2- (4-phenylfuran-3-) ) 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] thienyl) 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- (4-benzo [b] thienyl) phenyl group (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 group ) Phenyl group, 3- (6-benzo [b] thi) 4- (6-benzo [b] thienyl) phenyl group, 2- (7-benzo [b] thienyl) phenyl group, 3- (7-benzo [b] thienyl) phenyl group, 4- (7) 7-benzo [b] thienyl) phenyl group, 2- (2-benzo [b] furyl) phenyl group, 3- (2-benzo [b] furyl) phenyl group, 4- (2-benzo [b] furyl) Phenyl group, 2- (3-benzo [b] furyl) phenyl group, 3- (3-benzo [b] furyl) phenyl group, 4- (3-benzo [b] furyl) phenyl group, 2- (4-) Benzo [b] furyl) phenyl group, 3- (4-benzo [b] furyl) phenyl group, 4- (4-benzo [b] furyl) phenyl group, 2- (5-benzo [b] furyl) phenyl group , 3- (5-benzo [b] furyl) phenyl group, 4- (5 Benzo [b] furyl) phenyl group, 2- (6-benzo [b] furyl) phenyl group, 3- (6-benzo [b] furyl) phenyl group, 4- (6-benzo [b] furyl) phenyl group , 2- (7-benzo [b] furyl) phenyl group, 3- (7-benzo [b] furyl) phenyl group, 4- (7-benzo [b] furyl) 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-dibenzothienyl) phenyl group, 2- (3-dibenzothienyl) phenyl group, 3- (3-dibenzothienyl) phenyl group, 4- (3-dibenzothienyl) phenyl group, 2- (4-dibenzothienyl) phenyl group 4- (4-dibenzothienyl) phenyl group, 4- (4-dibenzothienyl) phenyl group, 2- (1-dibenzofuryl) phenyl group, 3- (1-dibenzofuryl) phenyl group, 4 -(1-Dibenzofuryl) phenyl group, 2- (2-dibenzofuryl) phenyl group, 3- (2-dibenzofuryl) phenyl group, 4- (2-dibenzofuryl) phenyl group, 2- (3-dibenzofuryl) ) Phenyl group, 3- (3-dibenzofuryl) phenyl group, 4- (3-dibenzofuryl) phenyl group, 2- (4-dibenzofuryl) phenyl group, 3- (4-dibenzofuryl) phenyl group, 4- (4) (4-dibenzofuryl) phenyl group, 3- (2-pyridyl) biphenyl-4-yl group, 2 '-(2-pyridyl) biphenyl-4-yl group, 4'-(2-pyridyl) group
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-pyridyl) biphenyl-3-yl group, 5- (2-pyridyl) biphenyl-2-yl group, 6- (2-pyridyl) biphenyl-2-yl group 2 ′-(2-pyridyl) biphenyl-2-yl 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- -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 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-yl 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) group ) 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 Group, 6,2′-di (4-pyridyl) biphenyl-2-yl group, 3- (1-naphth) B) biphenyl-4-yl group, 2 ′-(1-naphthyl) biphenyl-4-yl group, 4 ′-(1-naphthyl) biphenyl-4-yl group, 2,2′-di (1-naphthyl) group Biphenyl-4-yl group, 2 ′, 4 ′, 6′-tri (1-naphthyl) biphenyl-4-yl group, 6- (1-naphthyl) biphenyl-3-yl group, 5- (1-naphthyl) group 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) bipheny L-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-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-phenylnaphthalen-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalene 4-yl group, 1-phenylnaphthalen-5-yl group, 1-phenylnaphthalen-6-yl group, 1-phenylnaphthalen-7-yl group, 1-phenylnaphthalen-8-yl group, 2-phenylnaphthalene -1-yl group, 2-phenylnaphthalen-3-yl group, 2-phenylnaphthalen-4-yl group, 2-phenylnaphthalen-5-yl group, 2-phenylnaphthalen-6-yl group, 2-phenylnaphthalene -7-yl group, 2-phenylnaphthalen-8-yl group, 1-methyl group
2-methylnaphthalen-4-yl group, 1-methylnaphthalen-5-yl group, 1-methylnaphthalen-6-yl group, 1-methylnaphthalen-7-yl group, 1-methylnaphthalen-8-yl group, 2- Methyl naphthalen-1-yl group, 2-methyl naphthalen-3-yl group, 2-methyl naphthalen-4-yl group, 2-methyl naphthalen-5-yl group, 2-methyl naphthalen-6-yl group, 2- Methyl naphthalene-7-yl group, 2-methyl naphthalene-8-yl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-phenyl phenanthrene-2- 1-phenylphenanthren-3-yl group, 1-phenylphenanthrene-4-yl group, 1-phenylphenanthrene-5-i group 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 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 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 Group, 3-phenylphenanthrene-2-yl group, 3-phenylphen And 4-phenylphenanthrene-5-yl group, 3-phenylphenanthrene-6-yl group, 3-phenylphenanthrene-7-yl group, 3-phenylphenanthrene-8-yl group, 3-phenyl group Phenanthrene-9-yl group, 3-phenylphenanthrene-10-yl group, 4-phenylphenanthrene-1-yl group, 4-phenylphenanthrene-2-yl group, 4-phenylphenanthrene-3-yl group, 4-phenyl Phenanthrene-5-yl group, 4-phenylphenanthrene-6-yl group, 4-phenylphenanthrene-7-yl group, 4-phenylphenanthrene-8-yl group, 4-phenylphenanthrene-9-yl group, 4-phenyl group Phenanthrene-10-yl group, 1-methylphenanthrene-2-yl group, 1 -Methylphenanthrene-3-yl group, 1-methylphenanthrene-4-yl group, 1-methylphenanthrene-5-yl group, 1-methylphenanthrene-6-yl group, 1-methylphenanthrene-7-yl group, 1 -Methylphenanthrene-8-yl group, 1-methylphenanthrene-9-yl group, 1-methylphenanthrene-10-yl group, 2-methylphenanthren-1-yl group, 2-methylphenanthrene-3-yl group, 2 -Methylphenanthrene-4-yl group, 2-methylphenanthrene-5-yl group, 2-methylphenanthrene-6-yl group, 2-methylphenanthrene-7-yl group, 2-methylphenanthrene-8-yl group, 2 -Methylphenanthrene-9-yl group, 2-methylphenanthrene-10-yl group, 3-methylphenan Ren-1-yl group, 3-methylphenanthrene-2-yl group, 3-methylphenanthrene-4-yl group, 3-methylphenanthrene-5-yl group, 3-methylphenanthren-6-yl group, 3-methyl Phenanthrene-7-yl group, 3-methylphenanthrene-8-yl group, 3-methylphenanthrene-9-yl group, 3-methylphenanthrene-10-yl group, 4-methylphenanthrene-1-yl group, 4-methyl Phenanthrene-2-yl group, 4-methylphenanthrene-3-yl group, 4-methylphenanthrene-5-yl group, 4-methylphenanthrene-6-yl group, 4-methylphenanthrene-7-yl group, 4-methylphenanthrene-7-yl group Phenanthrene-8-yl group, 4-methylphenanthrene-9-yl group, 4-methylphenanthrene-10-yl group , 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenylanthracene-2-yl group, 1-phenylanthracene-3-yl group, 1-phenylanthracene-4-yl group, 1-phenylanthracene -5-yl group, 1-phenylanthracene-6-yl group, 1-phenylanthracene-7-yl group, 1-phenylanthracene-8-yl group, 1-phenylanthracene-9-yl group, 1-phenylanthracene -10-yl group, 2-phenylanthracene-1-yl group, 2-phenylanthracene-3-yl group, 2-phenylanthracene-4-yl group, 2-phenylanthracene-5-yl group, 2-phenylanthracene -6-yl group, 2-phenylanthracene-7-yl group, 2-phenylanthracene-8-yl group,
2-phenylanthracene-9-yl group, 2-phenylanthracene-10-yl group, 9-phenylanthracene-1-yl group, 9-phenylanthracene-2-yl group, 9-phenylanthracene-3-yl group, 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-phenylpyren-5-yl group, 1-phenylpyrene-6-yl group, 1-phenylpyrene-7-yl group, 1-phenylpyrene- 8-yl group, 1-phenylpyren-9-yl group, 1-phenylpyrene-10-yl group, 2-phenylpyren-1-yl group, 2-phenylpyren-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-phenylpyren-5-yl group, 9-phenylpyren-6-yl group, 9-phenylpyrene-7-yl group, 9-phenylpyren-8-yl group 9-phenylpyrene-10-yl group, 1-methylpyrene-2-yl group, 1-methylpyren-3-yl group, 1-methylpyrene-4-yl group, 1-methylpyren-5-yl group, 1-methylpyrene -6-yl 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-yl group, 2-methylpyrene-4-yl group, 2-methylpyren-5-yl group, 2-methylpyren-6-yl group, 2-methylpyrene-7-yl group, 2-methylpyren-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 -Yl group, 9-methyl pyren-5-yl group, 9-methyl pyren-6-yl group, 9-methyl pyren-7-yl group, 9-methyl pyren-8-yl group, 9-methyl pyren-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-yl group, fluoranthene-8-yl group, fluoranthene-9-yl group, fluoranthene-10-yl group, triphenylene-1-yl group, triphenylene-2-yl group, acenaphthylene-1-yl group, acenaphthylene -3-yl group, acenaphthyl-4-yl group, acenaphthyl-5-yl group, chrysene-1-yl group, chrysene-2-yl group, chrysene-5-yl group, chrysene-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, quinoxaline-2-yl group, quinoxaline-5-yl group Group, quinoxalin-6-yl group, quinazoline-2-yl group, quinazoline-4-yl group, quinazoline-5-yl group, quinazoline-6-yl group, quinazoline-7-yl group, quinazoline-8-yl group , Pyrazin-2-yl group, pyrimidin-2-yl group, pyrimidin-4-yl group, pyrimidin-5-yl group, acridin-1-yl group, acridin-1-yl group, acridin-2-yl group, Acridin-3-yl group, acridin-4-yl group, acridin-9-yl group, phenanthridin-1-yl group, phenanthridine-1-one Group, phenanthridin-2-yl group, phenanthridin-3-yl group, phenanthridin-4-yl group, phenanthridin-6-yl group, phenanthridin-7-yl group, phenant A lysine-8-yl group, a phenanthridin-9-yl group, a phenanthridine-10-yl group, a phenazin-1-yl group, a phenazin-2-yl group, a benzo [h] quinolin-2-yl group, Benzo [h] quinolin-3-yl group, benzo [h] quinolin-4-yl group, benzo [h] quinolin-5-yl group, benzo [h] quinolin-6-yl group, benzo [h] quinoline- 7-yl group, benzo [h] quinolin-8-yl group, benzo [h] quinolin-9-yl group, benzo [h] quinolin-10-yl group, 2-thienyl group, 3-thienyl group, 2- Furyl group, 3-furyl group,
Nzthiothiophen-2-yl group, benzothiophen-3-yl group, benzothiophen-4-yl group, benzothiophen-5-yl group, benzothiophen-6-yl group, benzothiophen-7-yl group, benzofuran-2 -Yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group, benzofuran-6-yl group, benzofuran-7-yl group, dibenzothiophen-1-yl group, dibenzothiophene- 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-methylthiophene-2 -Yl, 5-methylthiophen-2-yl, 2-methylthiophen-3-yl, 4-methylthione -3-yl group, 5-methylthiophen-3-yl group, 3-methylfuran-2-yl group, 4-methylfuran-2-yl group, 5-methylfuran-2-yl group, 2-methyl group Furan-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-methylbenzothiophen-3-yl group, 2-methylbenzothiophen-4-yl group Group, 3-methylbenzothiophen-4-yl group, 5-methylbenzothiophen-4-yl group, 6-methylbenzothiophen-4-yl group, 7-methylbenzothiophen-4-yl group, 2-methylbenzo group Thiophene-5-yl group, 3-methylbenzothiophen-5-yl group, 4-methylbenzothiophen-5-yl group, 6-methylbenzothiophen-5-yl group, 7-methylbenzothiophen-5-yl group , 2-methylbenzothiophen-6-yl group, 3-methylbenzothiophen-6-yl group, 4-methylbenzothiophen-6-yl group, 5-methylbenzothiophen-6-yl group, 7-methylbenzothiophene -6-yl group, 2-methylbenzothiophen-7-yl group, 3-methylbenzothiophen-7-yl group, 4-methylbenzothione En-7-yl group, 5-methylbenzothiophen-7-yl group, 6-methylbenzothiophen-7-yl group, 3-methylbenzofuran-2-yl group, 4-methylbenzofuran-2-yl group, 5-methylbenzofuran-2-yl group, 6-methylbenzofuran-2-yl group, 7-methylbenzofuran-2-yl group, 2-methylbenzofuran-3-yl group, 4-methylbenzofuran-3-yl group, 5-methylbenzofuran-3-yl group, 6-methylbenzofuran-3-yl group, 7-methylbenzofuran-3-yl group, 2-methylbenzofuran-4-yl group, 3-methylbenzofuran-4-yl group, 5-methylbenzofuran-4-yl group, 6-methylbenzofuran-4-yl group, 7-methylbenzofuran-4-yl group, 2-methylbenzofuran-5-yl group 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- group Group, 3-methylbenzofuran-7-yl group, 4-methylbenzofuran-7-yl group, 5-methylbenzofuran-7-yl group, 6-methylbenzofuran-7-yl group, 2-methyldibenzothiophene-1 -Yl group, 3-methyldibenzothiophen-1-yl group, 4-methyldibenzothiophen-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-methyldibenzothiophen-2-yl group, 8-methyldibenzothiophene-2 -Yl group, 9-methyldibenzothiophen-2-yl group, 1-methyldibenzothiophen-3-yl group, 2-methyldibenzothiophen-3-yl group, 4-methyldibenzothiophen-3-yl group, 6- Methyldibenzothiophen-3-yl group, 7-methyldibenzothiophen-3-yl group, 8-methyldibenzothione
En-3-yl group, 9-methyldibenzothiophen-3-yl 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-yl group, 2-methyldibenzofuran-3-yl group 4-methyldibenzofuran-3-yl group, 6-methyldibenzofuran-3-yl group, 7-methyldibenzofuran-3-yl group, 8-methyldibenzofuran-3-yl group, 9-methyldibenzofuran-3-yl group, 3-phenylthiophen-2-yl group, 4-phenylthiophen-2-yl group, 5-phenylthiophen-2-yl group, 2-phenylthiophen-3-yl group, 4-phenylthiophen-3-yl group, 5-phenylthiophen-3-yl group, 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-phenylbenzothiophen-2-yl group, 4-phenylbenzothione -2-yl group, 5-phenylbenzothiophen-2-yl group, 6-phenylbenzothiophen-2-yl group, 7-phenylbenzothiophen-2-yl group, 2-phenylbenzothiophen-3-yl group , 4-phenylbenzothiophen-3-yl group, 5-phenylbenzothiophen-3-yl group, 6-phenylbenzothiophen-3-yl group, 7-phenylbenzothiophen-3-yl group, 2-phenylbenzothiophene -4-yl group, 3-phenylbenzothiophen-4-yl group, 5-phenylbenzothiophen-4-yl group, 6-phenylbenzothiophen-4-yl group, 7-phenylbenzothiophen-4-yl group, 2-phenylbenzothiophen-5-yl group, 3-phenylbenzothiophen-5-yl group, 4-phenylbenzothi group Ophen-5-yl group, 6-phenylbenzothiophen-5-yl group, 7-phenylbenzothiophen-5-yl group, 2-phenylbenzothiophen-6-yl group, 3-phenylbenzothiophen-6-yl group , 4-phenylbenzothiophen-6-yl group, 5-phenylbenzothiophen-6-yl group, 7-phenylbenzothiophen-6-yl group, 2-phenylbenzothiophen-7-yl group, 3-phenylbenzothiophene -7-yl group, 4-phenylbenzothiophen-7-yl group, 5-phenylbenzothiophen-7-yl group, 6-phenylbenzothiophen-7-yl group, 3-phenylbenzofuran-2-yl group, 4 -Phenylbenzofuran-2-yl group, 5-phenylbenzofuran-2-yl group, 6-phenylbenzofuran- -Yl group, 7-phenylbenzofuran-2-yl group, 2-phenylbenzofuran-3-yl group, 4-phenylbenzofuran-3-yl group, 5-phenylbenzofuran-3-yl group, 6-phenylbenzofuran-3 -Yl group, 7-phenylbenzofuran-3-yl group, 2-phenylbenzofuran-4-yl group, 3-phenylbenzofuran-4-yl group, 5-phenylbenzofuran-4-yl group, 6-phenylbenzofuran-4 -Yl group, 7-phenylbenzofuran-4-yl group, 2-phenylbenzofuran-5-yl group, 3-phenylbenzofuran-5-yl group, 4-phenylbenzofuran-5-yl group, 6-phenylbenzofuran-5 -Yl group, 7-phenylbenzofuran-5-yl group, 2-phenylbenzofuran-6-yl group, 3-phenyl group 3-benzoyl benzofuran-6-yl group, 4-phenylbenzofuran-6-yl group, 5-phenylbenzofuran-6-yl group, 7-phenylbenzofuran-6-yl group, 2-phenylbenzofuran-7-yl group, 3- Phenylbenzofuran-7-yl group, 4-phenylbenzofuran-7-yl group, 5-phenylbenzofuran-7-yl group, 6-phenylbenzofuran-7-yl group, 2-phenyldibenzothiophen-1-yl group, 3 -Phenyldibenzothiophen-1-yl group, 4-phenyldibenzothiophen-1-yl group, 6-phenyldibenzothiophen-1-yl group, 7-phenyldibenzothiophen-1-yl group, 8-phenyldibenzothiophene-1 -Yl group, 9-phenyldibenzothiophen-1-yl group, 1-phenyldibenzothiof
En-2-yl group, 3-phenyldibenzothiophen-2-yl group, 4-phenyldibenzothiophen-2-yl group, 6-phenyldibenzothiophen-2-yl group, 7-phenyldibenzothiophen-2-yl group Group, 8-phenyldibenzothiophen-2-yl group, 9-phenyldibenzothiophen-2-yl group, 1-phenyldibenzothiophen-3-yl group, 2-phenyldibenzothiophen-3-yl group, 4-phenyldibenzo group Thiophene-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-phenyldibenzofu group -3-yl group, 8-phenyldibenzofuran-3-yl group, 9-phenyldibenzofuran-3-yl group, 3- (2-pyridyl) thiophen-2-yl group, 4- (2-pyridyl) thiophene- 2-yl group, 5- (2-pyridyl) thiophen-2-yl group, 2- (2-pyridyl) thiophen-3-yl group, 4- (2-pyridyl) thiophen-3-yl group, 5- (2-) 2-pyridyl) thiophen-3-yl group, 3- (2-pyridyl) furan-2-yl group, 4- (2-pyridyl) furan-2-yl group, 5- (2-pyridyl) furan-2-group -Yl, 2- (2-pyridyl) furan-3-yl, 4- (2-pyridyl) furan-3-yl, 5- (2-pyridyl) furan-3-yl, 3- (2- Pyridyl) benzothiophen-2-yl group, 4- (2-pyridin) Y) benzothiophen-2-yl group, 5- (2-pyridyl) benzothiophen-2-yl group, 6- (2-pyridyl) benzothiophen-2-yl group, 7- (2-pyridyl) benzothiophene- 2-yl group, 2- (2-pyridyl) benzothiophen-3-yl group, 4- (2-pyridyl) benzothiophen-3-yl group, 5- (2-pyridyl) benzothiophen-3-yl group, 6- (2-pyridyl) benzothiophen-3-yl group, 7- (2-pyridyl) benzothiophen-3-yl group, 2- (2-pyridyl) benzothiophen-4-yl group, 3- (2- Pyridyl) benzothiophen-4-yl group, 5- (2-pyridyl) benzothiophen-4-yl group, 6- (2-pyridyl) benzothiophen-4-yl group, 7- (2-pyridyl) benzothione And 4- (2-pyridyl) benzothiophen-5-yl group, 3- (2-pyridyl) benzothiophen-5-yl group, 4- (2-pyridyl) benzothiophen-5-yl group. Group, 6- (2-pyridyl) benzothiophen-5-yl group, 7- (2-pyridyl) benzothiophen-5-yl group, 2- (2-pyridyl) benzothiophen-6-yl group, 3- ( 2-pyridyl) benzothiophen-6-yl group, 4- (2-pyridyl) benzothiophen-6-yl group, 5- (2-pyridyl) benzothiophen-6-yl group, 7- (2-pyridyl) benzo group Thiophene-6-yl group, 2- (2-pyridyl) benzothiophen-7-yl group, 3- (2-pyridyl) benzothiophen-7-yl group, 4- (2-pyridyl) benzothiophen-7-yl group Group 5- (2-pyridyl) benzothiophen-7-yl group, 6- (2-pyridyl) benzothiophen-7-yl group, 3- (2-pyridyl) benzofuran-2-yl group, 4- (2-pyridyl) group ) 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-Pili
Dyl) benzofuran-4-yl group, 6- (2-pyridyl) benzofuran-4-yl group, 7- (2-pyridyl) benzofuran-4-yl group, 2- (2-pyridyl) benzofuran-5-yl group , 3- (2-pyridyl) benzofuran-5-yl group, 4- (2-pyridyl) benzofuran-5-yl group, 6- (2-pyridyl) benzofuran-5-yl group, 7- (2-pyridyl) group Benzofuran-5-yl group, 2- (2-pyridyl) benzofuran-6-yl group, 3- (2-pyridyl) benzofuran-6-yl group, 4- (2-pyridyl) benzofuran-6-yl group, 5 -(2-pyridyl) benzofuran-6-yl group, 7- (2-pyridyl) benzofuran-6-yl group, 2- (2-pyridyl) benzofuran-7-yl group, 3- (2-pyridyl) benzofuran- 7 -Yl, 4- (2-pyridyl) benzofuran-7-yl, 5- (2-pyridyl) benzofuran-7-yl, 6- (2-pyridyl) benzofuran-7-yl, 2- (2- Pyridyl) dibenzothiophen-1-yl group, 3- (2-pyridyl) dibenzothiophen-1-yl group, 4- (2-pyridyl) dibenzothiophen-1-yl group, 6- (2-pyridyl) dibenzothiophene- 1-yl group, 7- (2-pyridyl) dibenzothiophen-1-yl group, 8- (2-pyridyl) dibenzothiophen-1-yl group, 9- (2-pyridyl) dibenzothiophen-1-yl group, 1- (2-pyridyl) dibenzothiophen-2-yl group, 3- (2-pyridyl) dibenzothiophen-2-yl group, 4- (2-pyridyl) dibenzothiophen-2-yl group 6- (2-pyridyl) dibenzothiophen-2-yl group, 7- (2-pyridyl) dibenzothiophen-2-yl group, 8- (2-pyridyl) dibenzothiophen-2-yl group, 9- (2-) Pyridyl) dibenzothiophen-2-yl group, 1- (2-pyridyl) dibenzothiophen-3-yl group, 2- (2-pyridyl) dibenzothiophen-3-yl group, 4- (2-pyridyl) dibenzothiophene- 3-yl group, 6- (2-pyridyl) dibenzothiophen-3-yl group, 7- (2-pyridyl) dibenzothiophen-3-yl group, 8- (2-pyridyl) dibenzothiophen-3-yl group, 9- (2-pyridyl) dibenzothiophen-3-yl group, 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) group Dibenzofuran-1-yl group, 9- (2-pyridyl) dibenzofuran-1-yl group, 1- (2-pyridyl) dibenzofuran-2-yl group, 3- (2-pyridyl) dibenzofuran-2-yl group, 4 -(2-pyridyl) dibenzofuran-2-yl group, 6- (2-pyridyl) dibenzofuran-2-yl group, 7- (2-pyridyl) dibenzofuran-2-yl group, 8- (2-pyridyl) dibenzofuran- 2-yl group, 9- (2-pyridyl) dibenzofuran-2-yl group, 1- (2-pyridyl) dibenzofuran-3-yl group, 2- (2-pyridyl) dibenzofuran-3- Group, 4- (2-pyridyl) dibenzofuran-3-yl group, 6- (2-pyridyl) dibenzofuran-3-yl group, 7- (2-pyridyl) dibenzofuran-3-yl group, 8- (2- (2-pyridyl) dibenzofuran-3-yl group) Pyridyl) dibenzofuran-3-yl group, 9- (2-pyridyl) dibenzofuran-3-yl group, 3- (3-pyridyl) thiophen-2-yl group, 4- (3-pyridyl) thiophen-2-yl group , 5- (3-pyridyl) thiophen-2-yl group, 2- (3-pyridyl) thiophen-3-yl group, 4- (3-pyridyl) thiophen-3-yl group, 5- (3-pyridyl) group Thiophene-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-i Group, 4- (3-pyridyl) furan-3-yl group, 5- (3-pyridyl) furan-3-yl group, 3- (3-pyridyl) benzothiophen-2-yl group, 4- (3- (3-pyridyl) benzothiophen-2-yl group Pyridyl) benzothiophen-2-yl group, 5- (3-pyridyl) benzothiophen-2-yl group, 6- (3-pyridyl) benzothiophen-2-yl group, 7- (3-pyridyl) benzothiophene- 2-yl group, 2- (3-pyridyl) benzothiophen-3-yl group, 4- (3-pyridyl) benzothiophen-3-yl group, 5- (3-pyridyl) benzothiophen-3-yl group, 6- (3-pyridyl) benzothiophen-3-yl group, 7- (3-pyridyl) benzothiophen-3-yl group, 2- (3-pyridyl) benzothiophen-4-yl group, 3- (3- (3-pyridyl) benzothiophen-4-yl group Pyridyl) benzothiof
En-4-yl group, 5- (3-pyridyl) benzothiophen-4-yl group, 6- (3-pyridyl) benzothiophen-4-yl group, 7- (3-pyridyl) benzothiophene-4- Group, 2- (3-pyridyl) benzothiophen-5-yl group, 3- (3-pyridyl) benzothiophen-5-yl group, 4- (3-pyridyl) benzothiophen-5-yl group, 6- (3-pyridyl) benzothiophen-5-yl group, 7- (3-pyridyl) benzothiophen-5-yl group, 2- (3-pyridyl) benzothiophen-6-yl group, 3- (3-pyridyl) group Benzothiophene-6-yl group, 4- (3-pyridyl) benzothiophen-6-yl group, 5- (3-pyridyl) benzothiophen-6-yl group, 7- (3-pyridyl) benzothiophene 6- Group 2- (3-pyridyl) benzothiophen-7-yl group, 3- (3-pyridyl) benzothiophen-7-yl group, 4- (3-pyridyl) benzothiophen-7-yl group, 5- (3- (3-pyridyl) benzothiophene-7-yl group Pyridyl) benzothiophen-7-yl group, 6- (3-pyridyl) benzothiophen-7-yl group, 3- (3-pyridyl) benzofuran-2-yl group, 4- (3-pyridyl) benzofuran-2-one -Yl, 5- (3-pyridyl) benzofuran-2-yl, 6- (3-pyridyl) benzofuran-2-yl, 7- (3-pyridyl) benzofuran-2-yl, 2- (3- (3-pyridyl) benzofuran-2-yl Pyridyl) benzofuran-3-yl group, 4- (3-pyridyl) benzofuran-3-yl group, 5- (3-pyridyl) benzofuran-3-yl group, 6- (3-pyridyl) benzofuran-3-yl group , -(3-Pyridyl) benzofuran-3-yl group, 2- (3-pyridyl) benzofuran-4-yl group, 3- (3-pyridyl) benzofuran-4-yl group, 5- (3-pyridyl) benzofuran- 4-yl group, 6- (3-pyridyl) benzofuran-4-yl group, 7- (3-pyridyl) benzofuran-4-yl group, 2- (3-pyridyl) benzofuran-5-yl group, 3- ( 3-pyridyl) benzofuran-5-yl group, 4- (3-pyridyl) benzofuran-5-yl group, 6- (3-pyridyl) benzofuran-5-yl group, 7- (3-pyridyl) benzofuran-5-one -Yl, 2- (3-pyridyl) benzofuran-6-yl, 3- (3-pyridyl) benzofuran-6-yl, 4- (3-pyridyl) benzofuran-6-yl, 5- (3- (3-pyridyl) benzofuran-6-yl Pyridyl) ben Zofuran-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) dibenzothiophen-1-yl group, 4- (3-pyridyl) dibenzothiophen-1-yl group, 6- (3-pyridyl) dibenzothiophen-1-yl group 7- (3-pyridyl) dibenzothiophen-1-yl group, 8- (3-pyridyl) dibenzothiophen-1-yl group, 9- (3-pyridyl) dibenzothiophen-1-yl group, 1- 3-pyridyl) dibenzothiophen-2-yl group, 3- (3-pyridyl) dibenzothiophen-2-yl group, 4- (3-pyridyl) dibenzothiophen-2-yl group, 6- (3-pyridyl) dibenzo group Thiophene-2-yl group, 7- (3-pyridyl) dibenzothiophen-2-yl group, 8- (3-pyridyl) dibenzothiophen-2-yl group, 9- (3-pyridyl) dibenzothiophen-2-yl group Group, 1- (3-pyridyl) dibenzothiophen-3-yl group, 2- (3-pyridyl) dibenzothiophen-3-yl group, 4- (3-pyridyl) dibenzothiophen-3-yl group, 6- ( 3-pyridyl) dibenzothiophen-3-yl group, 7- (3-pyridyl) dibenzothiophen-3-yl group, 8- (3-pyridyl) dibenzothiophen-3-i group Group, 9- (3-pyridyl) dibenzothiophen-3-yl group, 2- (3-pyridyl) dibenzofuran-1-yl group, 3- (3-pyridyl) dibenzofuran-1-yl group, 4- (3- (3-pyridyl) dibenzofuran-1-yl group Pyridyl) dibenzofuran-1-yl group, 6- (3-pyridyl) dibenzofuran-1-yl group, 7- (3-pyridyl) dibenzofuran-1-yl group, 8- (3-pyridyl) dibenzofuran-1-yl group 9- (3-pyridyl) dibenzofuran-1-yl group, 1- (3-pyridyl) dibenzofuran-2-yl group, 3- (3-pyridyl) dibenzofuran-2-yl group, 4- (3-pyridyl) group Dibenzofuran-2-yl group, 6- (3-pyridyl) dibenzofuran-2-yl group, 7- (3-pyridyl) dibenzofuran-2-yl group, 8- (3-pyridyl) dibenzofuran
-2-yl group, 9- (3-pyridyl) dibenzofuran-2-yl group, 1- (3-pyridyl) dibenzofuran-3-yl group, 2- (3-pyridyl) dibenzofuran-3-yl group, 4- (3-pyridyl) dibenzofuran-3-yl group, 6- (3-pyridyl) dibenzofuran-3-yl group, 7- (3-pyridyl) dibenzofuran-3-yl group, 8- (3-pyridyl) dibenzofuran-3 -Yl, 9- (3-pyridyl) dibenzofuran-3-yl, 3- (4-pyridyl) thiophen-2-yl, 4- (4-pyridyl) thiophen-2-yl, 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 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, 4- (4-pyridyl) furan-3-yl, 5- (4-pyridyl) furan-3-yl, 3- (4-pyridyl) benzothiophen-2-yl, 4- (4 -Pyridyl) benzothiophen-2-yl group, 5- (4-pyridyl) benzothiophen-2-yl group, 6- (4-pyridyl) benzothiophen-2-yl group, 7- (4-pyridyl) benzothiophene -2-yl group, 2- (4-pyridyl) benzothiophen-3-yl group, 4- (4-pyridyl) benzothiophen-3-yl group, 5- (4-pyridyl) benzothiophen-3-yl group , 6- (4-pyridyl) benzothio En-3-yl group, 7- (4-pyridyl) benzothiophen-3-yl group, 2- (4-pyridyl) benzothiophen-4-yl group, 3- (4-pyridyl) benzothiophene-4- -Yl, 5- (4-pyridyl) benzothiophen-4-yl, 6- (4-pyridyl) benzothiophen-4-yl, 7- (4-pyridyl) benzothiophen-4-yl, 2- (4-pyridyl) benzothiophen-5-yl group, 3- (4-pyridyl) benzothiophen-5-yl group, 4- (4-pyridyl) benzothiophen-5-yl group, 6- (4-pyridyl) Benzothiophen-5-yl group, 7- (4-pyridyl) benzothiophen-5-yl group, 2- (4-pyridyl) benzothiophen-6-yl group, 3- (4-pyridyl) benzothiophene-6- Group 4- (4-pyridyl) benzothiophen-6-yl group, 5- (4-pyridyl) benzothiophen-6-yl group, 7- (4-pyridyl) benzothiophen-6-yl group, 2- (4 -Pyridyl) benzothiophen-7-yl group, 3- (4-pyridyl) benzothiophen-7-yl group, 4- (4-pyridyl) benzothiophen-7-yl group, 5- (4-pyridyl) 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-yl group, 2- (4-pyridyl) benzofuran- -Yl, 4- (4-pyridyl) benzofuran-3-yl, 5- (4-pyridyl) benzofuran-3-yl, 6- (4-pyridyl) benzofuran-3-yl, 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 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) group ) Benzofuran-5-yl group, 4- (4-pyridyl) benzofuran-5-yl group, 6- (4-pyridyl) benzofuran-5-yl group, 7- (4-pyridyl) benzofuran-5-yl group, 2- (4-) Lysyl) benzofuran-6-yl group, 3- (4-pyridyl) benzofuran-6-yl group, 4- (4-pyridyl) benzofuran-6-yl group, 5- (4-pyridyl) benzofuran-6-yl group 7- (4-pyridyl) benzofuran-6-yl group, 2- (4-pyridyl) benzofuran-7-yl group, 3- (4-pyridyl) benzofuran-7-yl group, 4- (4-pyridyl) group Benzofuran-7-yl group, 5- (4-pyridyl) benzofuran-7-yl group, 6- (4-pyridyl) benzofuran-7-yl group, 2- (4-pyridyl) dibenzothiophen-1-yl group, 3- (4-pyridyl) dibenzothiophen-1-yl group, 4- (4-pyridyl) dibenzothiophen-1-yl group, 6- (4-pyridyl) dibenzothiophen-1-yl group, 7- (4- (4-pyridyl) dibenzothiophen-1-yl group)
Pyridyl) dibenzothiophen-1-yl group, 8- (4-pyridyl) dibenzothiophen-1-yl group, 9- (4-pyridyl) dibenzothiophen-1-yl group, 1- (4-pyridyl) dibenzothiophene- 2-yl group, 3- (4-pyridyl) dibenzothiophen-2-yl group, 4- (4-pyridyl) dibenzothiophen-2-yl group, 6- (4-pyridyl) dibenzothiophen-2-yl group, 7- (4-pyridyl) dibenzothiophen-2-yl group, 8- (4-pyridyl) dibenzothiophen-2-yl group, 9- (4-pyridyl) dibenzothiophen-2-yl group, 1- (4-pyridyl) dibenzothiophen-2-yl group Pyridyl) dibenzothiophen-3-yl group, 2- (4-pyridyl) dibenzothiophen-3-yl group, 4- (4-pyridyl) dibenzothiophen-3-yl group, -(4-pyridyl) dibenzothiophen-3-yl group, 7- (4-pyridyl) dibenzothiophen-3-yl group, 8- (4-pyridyl) dibenzothiophen-3-yl group, 9- (4-pyridyl) ) Dibenzothiophen-3-yl group, 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) diben Furan-2-yl group, 6- (4-pyridyl) dibenzofuran-2-yl group, 7- (4-pyridyl) dibenzofuran-2-yl group, 8- (4-pyridyl) dibenzofuran-2-yl group, 9 -(4-pyridyl) dibenzofuran-2-yl group, 1- (4-pyridyl) dibenzofuran-3-yl group, 2- (4-pyridyl) dibenzofuran-3-yl group, 4- (4-pyridyl) dibenzofuran- 3-yl group, 6- (4-pyridyl) dibenzofuran-3-yl group, 7- (4-pyridyl) dibenzofuran-3-yl group, 8- (4-pyridyl) dibenzofuran-3-yl group, 9- ( A 4-pyridyl) dibenzofuran-3-yl group etc. are mentioned as a preferable example. Among these substituents, a 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 -(Fluoranthene-3-yl) phenyl group, 4- (fluoranthene-3-yl) phenyl group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 3- (3-pyridyl) Phenyl, 4- (3-pyridyl) phenyl, 3- (2-quinolyl) phenyl, 4- (2-quinolyl) phenyl, 3- (3-quinolyl) phenyl, 4- (3-quinolyl) The 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-benzofuryl) phenyl group 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- -Phenylpyridin-6-yl group, 2-phenylpyridin-5-yl group, 2-phenylpyridin-4-yl group, 3-phenylpyridin-5-yl group, 3-phenylpyridin-6-yl group, 5-phenyl group Thiophene-2-yl group, 5-phenylfuran-2-yl group, 1-naphthyl group, 2-naphthyl group, 2-benzothienyl group, 2-benzofuryl group, 1-phenanthryl group, 2-phenanthryl group, 3- Phenanthryl group, 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group or 4-dibenzofuryl group is preferable, and phenyl group, biphenyl-3-yl group, biphenyl-4-yl group 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) group
Phenyl group, 3- (fluoranthene-3-yl) phenyl group, 4- (fluoranthene-3-yl) phenyl group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 3- (fluorinated) phenyl group 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- (3-quinolyl) phenyl group 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-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, 4-dibenzofuryl group and the like are more preferable.

Thus, for Ar ² and Ar ³ , each independently, a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a fluoranthenylphenyl group, a pyridylphenyl group, a quinolylphenyl group, a thienylphenyl group Furyl phenyl group, benzothienyl phenyl group, benzofuryl phenyl group, dibenzothienyl phenyl group, dibenzo furyl phenyl group, naphthyl group, pyridyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl group or dibenzo It is preferable that it is a furyl group (these groups may be substituted with a fluorine atom or a methyl group), and each of them independently may be a phenyl group, a tolyl group, a dimethylphenyl group, a biphenyl group, a naphthylphenyl group or a phenyl group. Nantorylphenyl group, Rijirufeniru group, dibenzothienyl phenyl group, dibenzofuryl phenyl group, a naphthyl group, a pyridyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl group, or more preferably dibenzofuryl group.

In the general formula ^{(11), R 5, R} 6 and ^{R 7} each independently represents an alkyl group having 1 to 4 carbon atoms.

The alkyl group having 1 to 4 carbon atoms for R ⁵ , R ⁶ and R ⁷ is not particularly limited, but a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group or a t-butyl group A group etc. are mentioned as a preferable example. Among these substituents, a methyl group is more preferable in that it has excellent electron transporting material properties.

P represents 0, 1, 2, 3 or 4 in the general formula (11). When p is 2, 3 or 4, R ⁵ may be different from each other.

In the general formula (11), q represents 0, 1, 2, 3 or 4. When q is 2, 3 or 4, R ⁶ may be different from each other.

In the general formula (11), r represents 0, 1 or 2. When r is 2, two R ⁷ may be different from each other.

  Each of p, q and r is preferably independently 0 or 1 and more preferably all 0, in terms of excellent electron transporting material properties.

In General Formula (1), Ar ² has the same meaning as Ar ^{2 in} General Formula (11), and the preferred range is also the same.

In the general formula (1), Ar ³ is an aromatic hydrocarbon group which may be linked and / or fused with 10 to 24 carbon atoms, and has 3 to 25 carbon atoms composed of only a 6-membered ring A nitrogen-containing heteroaromatic group which may be linked and / or fused, or a C3-C25 linkage and / or condensation composed of an atom selected from the group consisting of H, C, O, and S It is preferable that it may be a heteroaromatic group which may be ringed (these groups may be substituted with a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms) .

From “a nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms which may be linked and / or fused, which is composed of only a 6-membered ring,” represented by Ar ³ , “H, C, O, and S And a heteroaromatic group which may be linked and / or fused with 3 to 25 carbon atoms, which is composed of atoms selected from the group consisting of: an alkyl group having 1 to 4 carbon atoms, and With respect to the alkoxy group of to 4, the same substituents as those exemplified for Ar ² can be exemplified.

Further, in the general formula (1), Ar ³ is only an aromatic hydrocarbon group having a carbon number of 10 to 24 and / or a condensed ring, and a 6-membered ring, in that it has excellent electron transporting material properties. A carbon comprising an atom selected from the group consisting of a nitrogen-containing heteroaromatic group which may be linked and / or fused, having 3 to 25 carbon atoms, or H, C, O, and S composed of It is preferable that it is a heteroaromatic group (These groups may be substituted by an alkyl group having 1 to 4 carbon atoms) which may be linked and / or fused with the number 3 to 25.

  Specifically, biphenyl group, naphthylphenyl group, phenanthrylphenyl group, fluoranthenylphenyl group, pyridylphenyl group, quinolylphenyl group, thienylphenyl group, furylphenyl group, benzothienylphenyl group, benzofurylphenyl group , Dibenzothienylphenyl group, dibenzofurylphenyl group, naphthyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl group, or dibenzofuryl group (these groups are substituted with a fluorine atom or a methyl group) Is preferable).

Furthermore, in the general formula (1), Ar ³ is an aromatic hydrocarbon group which may be linked and / or fused with 10 to 24 carbon atoms, and has 3 to 25 carbon atoms composed of only a 6-membered ring A nitrogen-containing heteroaromatic group which may be linked and / or fused, or a C3-C25 linkage and / or condensation composed of an atom selected from the group consisting of H, C, O, and S More preferably, it is a heteroaromatic group which may be cyclic.

Specifically, in the general formula (1), Ar ³ represents a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a fluoranthenylphenyl group, a pyridylphenyl group, a quinolylphenyl group, a thienylphenyl group, a furylphenyl group Group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, naphthyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl group, or dibenzofuryl group More preferably, it is a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a pyridylphenyl group, a dibenzothienylphenyl group, a dibenzofurylphenyl group, a naphthyl group or a phenanthryl group.

The aromatic hydrocarbon group which may have a carbon number of 10 to 24 and / or a condensed ring in Ar ³ in the general formula (1) is not particularly limited, but a biphenyl group or a terphenyl group Quaternary phenyl, naphthylphenyl, phenanthrylphenyl, anthrylphenyl, pyrenylphenyl, triphenylphenyl, chrysenylphenyl, fluoranthenylphenyl, acenaphthylphenyl, fluorenyl Phenyl group, naphthyl biphenyl group, naphthyl group, phenyl naphthyl group, biphenyl naphthyl group, phenanthryl naphthyl group, anthryl naphthyl group, phenanthryl group, phenyl phenanthryl group, naphthyl phenanthryl group, anthryl group, phenyl anthryl group Group, naphthyl anthryl group, pyrenyl group, fe Nylpyrenyl group, triphenylenyl group, phenyltriphenylenyl group, chrysenyl group, phenylchrysenyl group, fluoranthenyl group, phenylfluoranthenyl group, acenaphthyl group, phenylacenaphthyl group, fluorenyl group, phenylfluorenyl group, or A benzofluorenyl group etc. are mentioned as a preferable example. These substituents may be substituted by a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

In the general formula (1), specific examples of Ar ^3, is not particularly limited, it can be exemplified the same substituents as those specifically illustrated by Ar ² described above. However, it does not include an aromatic hydrocarbon group which may be linked and / or fused and has less than 10 carbon atoms.

  When this compound is used as a part of the constituent components of an organic electroluminescent device, effects such as high luminous efficiency, long life, low voltage and the like can be obtained. In particular, when used as an electron transport layer, this effect appears notably.

  Among the compounds represented by the general formula (11) or the general formula (1), the following (A-1) to (A-1165) can be exemplified as specific examples of particularly preferable compounds, but the present invention It is not limited.

  Hereinafter, applications of the triazine compound (11) or (1) will be described.

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

The organic electroluminescent device 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 the light emitting layer as needed, and has a structure of being sandwiched between a cathode and an anode. Specifically, the structures shown below can be mentioned.
(I) anode / emitting layer / cathode (ii) anode / hole transporting layer / emitting layer / cathode (iii) anode / emitting layer / electron transporting layer / cathode (iv) anode / hole transporting layer / emitting layer / electron Transport Layer / Cathode (v) Anode / Anode Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode Buffer Layer / Cathode The light emitting layer in the organic electroluminescent device of the present invention uses a conventionally known light emitting material. be able to. As a method of forming a light emitting layer, there is a method of forming a thin film by a known method such as, for example, a vapor deposition method, a spin coating method, a cast method, an LB method.

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

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

  Next, other layers such as a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer, which constitute an organic electroluminescent device in combination with a light emitting layer, will be described.

  The hole injecting layer and the hole transporting layer have a function of transferring holes injected from the anode to the light emitting layer, and the hole injecting layer and the hole transporting layer may be 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.

  In addition, 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 barrier of electrons present 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 transporting layer, and the element has excellent light emitting performance such as improvement of the light emitting efficiency.

  The hole injecting material and the hole transporting material have any of hole injecting or transporting and electron blocking properties, and may be either organic or inorganic. Examples of the hole injection material and the hole transport material include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazoles Derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, particularly thiophene oligomers, etc. may be mentioned. As the hole injecting material and the hole transporting material, those described above can be used, but porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, in particular aromatic tertiary amine compounds, may be used preferable.

As representative examples of the above aromatic tertiary amine compounds and styrylamine compounds, 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- Tolylaminophenyl) -4-phenylcyclohexane, bis (4-dimethylamino-2-methylphenyl) phenylmethane, bis (4-di-p-tolylaminophenyl) phenylmethane, N, N'-diphenyl-N, N 4-di (4-meth) Siphenyl) -4,4'-diaminobiphenyl, N, N, N ', N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis (diphenylamino) quadriphenyl, N, N, N-tri (p-tolyl) amine, 4- (di-p-tolylamino) -4 '-[4- (di-p-tolylamino) styryl] stilbene, 4-N, N-diphenylamino- (2-diphenyl) Vinyl) benzene, 3-methoxy-4'-N, N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), Examples include 4,4 ′, 4 ′ ′-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (MTDATA) and the like.

  Inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material. 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 vacuum evaporation, spin coating, casting, LB method, etc. It can be formed. The 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 single layer structure made of one or more of the above materials, or may have a laminated structure made 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 (11) or (1).

  The electron transporting layer is formed by forming a triazine compound represented by the above general formula (11) or (1) by a known thin film forming method such as vacuum evaporation method, spin coating method, casting method or LB method. It can be formed. Although the film thickness of an electron carrying layer does not have a restriction | limiting in particular, Usually, it is chosen in 5 nm-5 micrometers. In addition, this electron transport layer contains a triazine compound represented by the general formula (11) or (1), and may contain a conventionally known electron transport material, and has a single layer structure comprising one or two or more species. It may be a laminated structure composed of a plurality of layers of the same composition or different compositions.

  Further, in the present invention, the light emitting material is not limited to only the light emitting layer, and one kind of light emitting material may be contained in the hole transporting layer adjacent to the light emitting layer or the electron transporting layer. The light emission efficiency of the

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

  The light transmitting plastic film includes, for example, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), polyether imide, polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC) And films made of cellulose triacetate (TAC), cellulose acetate propionate (CAP) and the like.

  A preferred example of producing the organic electroluminescent device of the present invention will be described. As an example, a method of manufacturing an organic electroluminescent device comprising the above-mentioned 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 material such as an anode material is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 μm or less, preferably 10 to 200 nm. Make the 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 thereon.

  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.

  Furthermore, layers having other functions may be laminated as necessary in addition to the above-mentioned basic constituent layer, and for example, functional layers such as a hole blocking layer and an electron blocking 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 device, one having 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 be formed into a thin film of these electrode materials by a method such as evaporation or sputtering, and a pattern of a desired shape may be formed by photolithography, or a pattern through a mask of a desired shape during evaporation or sputtering. May be formed.

On the other hand, it is preferable to use, as the cathode, a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound and a mixture thereof as an electrode material. 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 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals, etc. may be mentioned. Among them, a mixture of an electron-injectable metal and a second metal which is a stable metal having a large work function value, such as magnesium / silver mixture, magnesium, from the viewpoint of electron injectability and durability against oxidation etc. Preferred are aluminum / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) mixture, lithium / aluminum mixture and the like. The cathode can be produced by forming a thin film of such an electrode material by a method such as vapor deposition or sputtering.

  As described above, a thin film made of a desired electrode material such as an anode material is formed on an appropriate substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 μm or less, preferably 10 to 200 nm. After forming an anode, forming a thin film of each of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer / electron injection layer on the anode as described above, and forming a thin film thereon A desired organic electroluminescent device is obtained by forming a thin film of a substance with a thickness of 1 μm or less, preferably 50 to 200 nm, by a method such as evaporation or sputtering and providing a cathode.

  The organic electroluminescent device of the present invention may be used as a kind of lamp such as illumination and exposure light source, a projection device of a type for projecting an image, and a display of a type for directly viewing a still image or a moving image. It may be used as a device (display). When used as a display device for moving image reproduction, either a simple matrix (passive matrix) method or an active matrix method may be used as a driving method. In addition, a full color display can be manufactured by using two or more kinds of the organic electroluminescent device of the present invention having different luminescent colors.

  Next, the manufacturing method of the present invention will be described.

  The triazine compound (11) of the present invention has the following reaction formula (11) in the presence or absence of a base and in the presence of a palladium catalyst:

(In the reaction formula (11), Ar ¹ , Ar ² , Ar ³ , R ⁵ , R ⁶ , R ⁷ , p, q, r, Z ¹ and Z ² have the same substituents as in the general formula (11) Y represents a leaving group described later, and M represents a substituent described later.)
Or reaction formula (12)

(In the reaction formula (12), Ar ¹ , Ar ² , Ar ³ , R ⁵ , R ⁶ , R ⁷ , p, q, r, Z ¹ and Z ² have the same substituents as in the general formula (11) Y represents a leaving group described later, and M represents a substituent described later.)
It can manufacture by the method shown.

  Further, hereinafter, the compound represented by the general formula (12) is referred to as a compound (12). The same applies to the compounds (13) to (15).

M each independently represents ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ . However, R ¹ and R ² each independently represent a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, R ⁴ represents a hydrogen atom, 1 carbon atom To 4 alkyl groups or phenyl groups, and two R ⁴ in B (OR ⁴ ) ₂ may be the same or different. In addition, two R ⁴ can be combined to form a ring by containing an oxygen atom and a boron atom.

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

The ^{_{Sn (R 3) 3, 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. Moreover, as an example of B (OR ⁴ ) ₂ when two R ⁴ together form an oxygen atom and a boron atom to form a ring, the following (C-1) to (C-6) The group shown can be illustrated, and the group shown by (C-2) is desirable in terms of a good yield.

  The compound (13) used in the reaction formula (11) can be prepared, for example, by the method disclosed in JP-A-2005-268199 [0105] to [0121] and JP-A-2008-280330 [0061] to [0076] ] Or it can manufacture combining the method currently disclosed by Unexamined-Japanese-Patent No. 2001-335516 [0047]-[0082]. Although the following (B-1) to (B-56) can be illustrated as a compound (13), this invention is not limited to these.

  Compound (15) can illustrate the compound which substituted M of said compound (13) to Y in Reaction Formula (12).

  Y in the compound (12) and the compound (15) is a leaving group, and examples thereof include, but are not limited to, chlorine atom, bromine atom, iodine atom, triflate and the like. Among these, a bromine atom or a chlorine atom is preferable in terms of a good reaction yield. However, it may be preferable to use triflate from the availability of the raw material.

  Subsequently, reaction formula (11) will be described. “Step 11” is a method of reacting Compound (12) with Compound (13) in the presence or absence of a base and in the presence of a palladium catalyst to obtain the triazine compound (11) of the present invention, By applying reaction conditions of general coupling reaction such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc., the desired product can be obtained with good yield.

  As a palladium catalyst which can be used at "the process 11", salts, such as palladium chloride, palladium acetate, palladium trifluoroacetate, palladium nitrate, etc. can be illustrated. Furthermore, π-allylpalladium 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, a palladium complex having a tertiary phosphine as a ligand is further preferable in that the reaction yield is good, and is easy to obtain, and a palladium complex having a triphenylphosphine as a ligand in terms of a good reaction yield. Particularly preferred.

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 complex compound. Examples of tertiary phosphines that can be used in this case include triphenylphosphine, trimethylphosphine, tributylphosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5. -Bis (diphenylphosphino) xanthene, 2- (diphenylphosphino) -2 '-(N, N-dimethylamino) biphenyl, 2- (di-tert-butylphosphino) biphenyl, 2- (dicyclohexylphosphino) Biphenyl, bis (diphenylphosphino) methane, 1,2-bis (diphenylphosphino) ethane, 1,3-bis (diphenylphosphino) propane, 1,4-bis (diphenylphosphino) butane, 1,1 ′ -Bis (diphenylphosphino) group Rhocene, tri (2-furyl) phosphine, tri (o-tolyl) phosphine, tris (2,5-xylyl) phosphine, (±) -2,2'-bis (diphenylphosphino) -1,1'-binaphthyl And 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl and the like. 2-Dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl or triphenylphosphine is preferred in view of easy availability and good reaction yield. The molar ratio of tertiary phosphine to palladium salt or complex compound is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 in terms of a good reaction yield.

  Examples of bases that can be used in “Step 11” include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, potassium phosphate, sodium phosphate, sodium fluoride, sodium fluoride, potassium fluoride And the like, and potassium carbonate is desirable in terms of a good yield. The molar ratio of the base to the compound (13) is desirably 1: 2 to 10: 1, and more desirably 1: 1 to 3: 1 in terms of a good yield.

  The molar ratio of the compound (12) to the compound (13) used in “Step 11” is preferably 1: 2 to 5: 1, and more preferably 1: 2 to 2: 1 in terms of a good yield.

  Examples of the solvent that can be used in “Step 11” include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, toluene, benzene, diethyl ether, ethanol, methanol, xylene and the like. You may use it combining suitably. It is desirable to use dioxane or a mixed solvent of tetrahydrofuran and water from the viewpoint of a good yield.

  The “step 11” can be carried out at a temperature appropriately selected from 0 ° C. to 150 ° C., and it is more preferable to carry out at 50 ° C. to 100 ° C. in terms of a good yield.

  Compound (11) is obtained by the usual processing after the end of “Step 11”. If necessary, purification may be performed by recrystallization, column chromatography, sublimation or the like.

  “Step 12” is a method of reacting a compound (14) with a compound (15) in the presence or absence of a base and in the presence of a palladium catalyst to obtain a triazine compound (11) of the present invention, By applying reaction conditions of general coupling reaction such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc., the desired product can be obtained with good yield. Among the conditions listed in “Step 11”, “Step 12” can apply the conditions in which the compound (12) is replaced with the compound (15) and the compound (13) is replaced with the compound (14). However, the reaction conditions do not have to be the same as in “Step 11”. After completion of “Step 12”, purification may be performed by recrystallization, column chromatography, sublimation or the like, as necessary.

  In addition, triazine compound (1) can be reacted with 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 in the general formula (1), Y represents the above-mentioned leaving group, and M is Represents the above-mentioned substituent), or reaction formula (2)

(In the reaction formula (2), Ar ¹ , Ar ² , Ar ³ , Z ¹ and Z ² represent the same substituents as in the general formula (1), Y represents the above-mentioned leaving group, and M is It represents the above-mentioned substituent.)
It can manufacture by the method shown.

  The reaction conditions and the like in the reaction formulas (1) and (2) are the same as those in the reaction formulas (11) and (12), respectively. That is, for the step 1, the reaction can be carried out in the same manner as the above-mentioned step 11, and for the step 2, the reaction can be carried out in the same manner as the step 12.

  The triazine compounds (11) and (1) of the present invention are suitably used as materials for organic electroluminescent devices.

  Furthermore, the triazine compounds (11) and (1) of the present invention are suitably used as an electron transporting material or an electron injecting material for an organic electroluminescent device.

  The triazine compounds (11) and (1) of the present invention are effective when used as part of the components of the organic electroluminescent device. In particular, when used as an electron transport layer, effects such as longer life, higher efficiency, lower voltage and the like can be obtained compared to conventional devices. Moreover, when using the triazine compound (11) of this invention as a material for organic electroluminescent elements, it is also possible to use as a vapor deposition film with arbitrary organic metal types, organic compounds, or an inorganic compound.

Although there is no restriction | limiting in particular in the manufacturing method of the thin film for organic electroluminescent elements which consists of triazine compound (11) and (1) of this invention, The film-forming by a vacuum evaporation method is possible. The film formation by the vacuum evaporation method can be performed by using a general-purpose vacuum evaporation apparatus. The degree of vacuum of the vacuum chamber at the time of forming a film by a vacuum evaporation method is a diffusion pump, turbo molecular pump, cryopump, etc. generally used, in consideration of the manufacturing tact time and manufacturing cost of organic electroluminescent element fabrication. It is preferably about 1 × 10 ⁻² to 1 × 10 ⁻⁵ to 1 × 10 ⁻⁶ Pa, and more preferably 1 × 10 ⁻³ to 10 ⁻⁶ Pa, which can be reached by The deposition rate is preferably 0.005 to 1.0 nm / second, more preferably 0.01 to 1 nm / second, depending on the thickness of the film to be formed. In addition, since the triazine compounds (11) and (1) of the present invention have high solubility in chloroform, dichloromethane, 1,2-dichloroethane, chlorobenzene, toluene, ethyl acetate, tetrahydrofuran or the like, spin coty Film formation by a casting method, an ink jet method, a cast method, or a dip method is also possible.

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

  The anode and the cathode of the organic electroluminescent element are connected to a power source via an electrical conductor. The organic electroluminescent device operates by applying a potential between the anode and the cathode. 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 coated on a substrate, and the anode or the cathode can be in contact with the substrate. The electrode in contact with the substrate is conveniently referred to as the lower electrode. In general, 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 light emission direction. Light transmission properties are desirable for viewing the electroluminescent emission through the substrate. Transparent glass or plastic is generally employed as such a substrate. The substrate may be a composite structure comprising multiple material layers.

  If electroluminescent emission is viewed through the anode, the anode should either pass or substantially transmit the emission. Typical transparent anode (anode) materials used in the present invention are indium-tin oxide (ITO), indium-zinc oxide (IZO), or tin oxide, but other metal oxides, for example Also useful are aluminum or indium-doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide. In addition to these oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, or metal sulfides such as zinc sulfide can be used as the anode. The anode can be modified with plasma deposited fluorocarbons. For applications where electroluminescence is only seen through the cathode, the transmission properties of the anode are not critical and any conductive material transparent, opaque or reflective 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 serve to 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 injection layer include porphyrin compounds, plasma deposited fluorocarbon polymers, and amines having an aromatic ring such as biphenyl or carbazole, 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, tolylamine, tolyldiphenylamine, 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-phenylcarbazol-3-yl) -1,1'-biphenyl-4,4'-diamine and the like can be mentioned.

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 are meant to be 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 It forms an aromatic ring. Specifically, the aromatic tertiary amine may be an arylamine, such as a monoarylamine, a diarylamine, a triarylamine, or a polymeric arylamine.

  As the hole transport material, aromatic tertiary amines having one or more amine groups can be used. In addition, polymeric hole transport materials can be used. For example, poly (N-vinylcarbazole) (PVK), polythiophene, polypyrrole, or polyaniline can be used. For example, NPD (N, N'-bis (naphthalen-1-yl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine), α-NPD (N, N'-di) (1-Naphthyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine), TPBi (1,3,5-tris (1-phenyl-1H-benzimidazol-2-yl) And benzene), or 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 charge generation layer between hole injection layer and 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, and in this case, light emission occurs as a result of 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 consists of a host material doped with a guest compound, in which case the emission mainly consists of dopants 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-carbazovinylene) 1,1'-biphenyl ), TBADN (2-tert-butyl-9,10-di (2-naphthyl) anthracene), ADN (9,10-di (2-naphthyl) anthracene), CBP (4,4'-bis (carbazole-9) -Yl) biphenyl), CDBP (4,4'-bis (carbazol-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, or another material supporting hole-electron recombination or a combination of these materials.

  Examples of useful fluorescent dopants include anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine and quinacridone, dicyanomethylene pyran compound, thiopyran compound, polymethine compound, pyrilium or thiapyrilium compound, fluorene derivative, periflanthene derivative, indeno Perylene derivatives, bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, carbostyril compounds and the like can be mentioned.

  One example of a useful phosphorescent dopant is an organometallic complex of a transition metal of iridium, platinum, palladium or osmium.

Examples of dopants include Alq ₃ (tris (8-hydroxyquinoline) aluminum), DPAVBi (4,4′-bis [4- (di-para-tolylamino) styryl] biphenyl), perylene, Ir (PPy) ₃ ( Tris (2-phenylpyridine) iridium (III), or FlrPic (bis (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III), etc. may be mentioned.

  The thin film-forming material used to form the electron transport layer of the organic electroluminescent device of the present invention is the triazine compound (11) or (1) of the present invention. The electron transporting layer may contain other electron transporting materials, and examples of the electron transporting materials include alkali metal complexes, alkaline earth metal complexes, earth metal complexes and the like. Desirable alkali metal complexes, alkaline earth metal complexes, earth metal complexes such as lithium 8-hydroxyquinolinate (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) beryllium, bis (10-hydroxybenzo [h] quinolinate) zinc, bis (2-methyl-8-quinolinate) chlorogallium, bis (2-methyl-8-quinolinate) ( o-Cresolato) gallium, bis (2-methyl-8-quinolina) G) -1-naphthoquinone Trad aluminum or bis (2-methyl-8-quinolinato) -2-naphthoquinone Trad gallium, and the like.

  A hole blocking layer may be provided between the light emitting layer and the electron transporting layer for the purpose of improving carrier balance. Preferred compounds for the hole blocking layer are BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2 And -methyl-8-quinolinolato) -4- (phenylphenolate) aluminum), or bis (10-hydroxybenzo [h] quinolinate) beryllium) and the like.

  In the organic electroluminescent device of the present invention, an electron injection layer may be provided for the purpose of improving the electron injection property and improving the device characteristics (for example, light emission 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, fluorenylidenemethane, anthraquinodimethane, or anthrone. Etc. Also, the above-mentioned metal complexes, alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, SiO _x , AlO _x , SiN _x , SiON, _{AlON, GeO X, LiO X,} LiON, TiO X, TiON, TaO X, TaON, TaN X, C and various oxides, may be used an inorganic compound such as a nitride, and oxynitride.

When light emission is only seen through the anode, the cathode used in the present invention can be formed from almost any conductive material. Preferred cathode 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 ) mixture, indium , Lithium / aluminum mixtures, rare earth metals and the like.

  ADVANTAGE OF THE INVENTION According to this invention, the triazine compound which is excellent in the heat resistance of film quality can be provided, and the organic electroluminescent element which is excellent in a low voltage, a long life, or luminous efficiency can be provided.

It is a cross-sectional view of the single layer element produced in the Example.

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

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

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

  Synthesis example-1

  In an air atmosphere, 4-bromobenzaldehyde (3.00 g, 0.0162 mol) and 2-acetonaphthone (2.78 g, 0.0163 mol) are dissolved in acetic acid (32.4 mL), concentrated sulfuric acid (4.5 mL, 0. 2). 0811 mol) was added dropwise and stirred at room temperature for 2 hours. After stirring, 50 mL of water was added, and the precipitated solid was separated by filtration. The resulting solid was washed with water (50 mL) and methanol (50 mL) to give a red-white solid (yield 3.32 g, yield of the objective 3- (4-bromophenyl) -1- (2-naphthyl) propenone. Rate of 74%).

  Synthesis example-2

  Under an air atmosphere, 3- (4-bromophenyl) -1- (2-naphthyl) propenone (3.03 g, 8.99 mmol), 1-phenacylpyridinium bromide (3.75 g, 0.0135 mol), ammonium acetate ( 13.76 g (0.179 mol) was suspended in a mixed solvent of acetic acid (90 mL) and dimethylformamide (90 mL), and stirred at 150 ° C. for 13 hours. After cooling to room temperature, water (100 mL) was added, and the precipitated solid was separated by filtration. The resulting solid is washed with water (100 mL) to give the target 4- (4-bromophenyl) -2- (2-naphthyl) -6-phenylpyridine as a brown solid (yield 3.11 g, 80) %) Got.

  Synthesis example-3

  Dissolve 4- (4-bromophenyl) -2- (2-naphthyl) -6-phenylpyridine (2.5 g, 5.73 mmol) in tetrahydrofuran (50 mL) under argon flow and stir at -78 ° C. for 20 minutes did. To this was added dropwise normal butyl lithium (normal hexane solution, 7.38 mmol) and stirred for 2 hours. Subsequently, triisopropyl borate (1.70 mL, 7.41 mmol) was added and stirred for 16 hours. After stirring, 4 M aqueous sodium hydroxide solution (4 mL, 16.0 mmol) was added and stirred for 1 hour. Water (50 mL) was added to the reaction solution, and extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous sodium chloride solution, and the organic layer and the aqueous layer were separated. After dehydrating the organic layer using magnesium sulfate, the target 4- [2- (2-naphthyl) -6-phenylpyridin-4-yl] phenylboronic acid is obtained by concentrating the low boiling point component from the organic layer under reduced pressure. A pale yellow solid (yield 1.81 g, 79%) was obtained.

  Example 1

Under an argon stream, 4- [2- (2-naphthyl) -6-phenylpyridin-4-yl] phenylboronic acid (1.60 g, 3.99 mmol), 2- (3-bromophenyl) -4,6- Diphenyl-1,3,5-triazine (1.13 g, 2.93 mmol), tetrakis (triphenylphosphine) palladium (0.104 g, 0.09 mmol) were suspended in tetrahydrofuran (50 mL). To this, 2 M aqueous potassium carbonate solution (4.4 mL, 8.80 mmol) was added and stirred at 80 ° C. for 22 hours. After cooling to room temperature, water (80 mL) and methanol (20 mL) were added, and the precipitated solid was separated by filtration, and the solid was washed with water (50 mL), methanol (50 mL) and hexane (50 mL). The solid was dissolved in toluene (300 mL), filtered through celite, and the filtrate was concentrated under reduced pressure to give a crude product. The resulting crude product is purified by recrystallization (toluene) to obtain the target 2- {4 '-[2- (2-naphthyl) -6-phenylpyridin-4-yl] biphenyl-3-yl} -4. , 6-Diphenyl-1,3,5-triazine (compound A-2) white powder (yield 1.41 g, 73%
Got).

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.48-7.65 (m, 11 H), 7.72 (t, J = 7.6 Hz, 1 H), 7.90-8.05 (m , 9H), 8.15 (dd, J = 1.4 Hz, 1 H), 8.27-8.31 (m, 2 H), 8.39-8.43 (dd, J = 8.3 Hz, 1 H) , 8.71 (brs, 1 H), 8.80-8.85 (m, 5 H), 9.09 (t, J = 1.6 Hz, 1 H).
Tg of obtained compound A-2 was 112 ° C.

  Synthesis example-4

  In an air atmosphere, 2-naphthaldehyde (3.01 g, 0.0193 mol) and 4-bromoacetophenone (3.83 g, 0.0192 mol) are dissolved in acetic acid (38 mL), concentrated sulfuric acid (5.3 mL, 0.0960 mol) ) Was added dropwise and stirred at room temperature for 2 hours. After stirring, 50 mL of water was added, and the precipitated solid was separated by filtration. The obtained solid is washed with water (50 mL) and methanol (50 mL) to obtain a target yellow solid (Yield 4.08 g, 1- (4-bromophenyl) -3- (2-naphthyl) propenone). 63%).

  Synthesis example-5

  1- (4-bromophenyl) -3- (2-naphthyl) propenone (3.00 g, 8.89 mmol), 1-phenacyl pyridinium bromide (3.73 g, 0.0134 mol), ammonium acetate (under air atmosphere) 13.67 g (0.177 mol) was suspended in a mixed solvent of acetic acid (90 mL) and dimethylformamide (90 mL), and stirred at 150 ° C. for 15 hours. After cooling to room temperature, 100 mL of water was added, and the precipitated solid was separated by filtration. The obtained solid is washed with water (100 mL) to give a target brown solid (yield 2.96 g, 76 of 2- (4-bromophenyl) -4- (2-naphthyl) -6-phenylpyridine). %) Got.

  Synthesis example-6

  Under an argon stream, 2- (4-bromophenyl) -4- (2-naphthyl) -6-phenylpyridine (2.20 g, 5.04 mmol) was dissolved in tetrahydrofuran (50 mL) and stirred at -78 ° C. To this, normal butyl lithium (normal hexane solution, 6.55 mmol) was added dropwise and stirred for 1 hour. Subsequently, triisopropyl borate (1.50 mL, 6.55 mmol) was added and stirred for 22 hours. After stirring, 4 M aqueous sodium hydroxide solution (4 mL, 16 mmol) was added and stirred for 15 minutes. Water was added to the reaction solution and extracted with ethyl acetate (140 mL). The organic layer was washed with saturated aqueous sodium chloride solution, and the organic layer and the aqueous layer were separated. After dehydrating the organic layer using magnesium sulfate, the target 4-{[4- (2-naphthyl) -6-phenyl] pyridin-2-yl} phenyl is obtained by concentrating the low boiling point components from the organic layer under reduced pressure. A pale yellow solid (yield 1.67 g, 83%) of boronic acid was obtained.

  Example 2

  Under an argon stream, 4-{[4- (2-naphthyl) -6-phenyl] pyridin-2-yl} phenylboronic acid (1.60 g, 3.99 mmol), 2- (3-bromophenyl) -4, 6-Diphenyl-1,3,5-triazine (1.04 g, 2.68 mmol) and tetrakis (triphenylphosphine) palladium (0.107 g, 0.08 mmol) were dissolved in tetrahydrofuran (50 mL). To this, 2 M aqueous potassium carbonate solution (4 mL, 8.0 mmol) was added and stirred at 80 ° C. for 25 hours. After cooling to room temperature, water (80 mL) and methanol (20 mL) were added, and the precipitated solid was separated by filtration. The resulting solid was washed with water (50 mL), methanol (50 mL), hexane (50 mL). This solid is dissolved in toluene (400 mL), filtered through Celite, and the filtrate is concentrated under reduced pressure and then purified by recrystallization (toluene) to obtain the desired 2- {4 '-[4- (2-naphthyl) White powder of (6-phenylpyridin-2-yl) biphenyl-3-yl} -4,6-diphenyl-1,3,5-triazine (compound A-362) (yield 1.36 g, 76%) I got

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.52-7.67 (m, 11 H), 7.71 (t, J = 7.7 Hz, 1 H), 7.90-8.07 (m , 8H), 8.13 (d, J = 1.4 Hz, 1 H), 8.26-8.31 (m, 3 H), 8.43 (d, J = 8.5)
Hz, 2H), 8.79-8.84 (m, 5H), 9.10 (t, J = 1.6 Hz, 1 H).
The Tg of the obtained compound A-362 was 109 ° C.

  Synthesis example-7

  In an air atmosphere, benzaldehyde (3.00 g, 0.0283 mol) and 2-acetonaphthone (4.83 g, 0.0284 mol) were dissolved in acetic acid (57 mL), and concentrated sulfuric acid (7.9 mL, 0.141 mol) was added dropwise. The mixture was stirred at room temperature for 21 hours. After stirring, 50 mL of water was added, and the precipitated solid was separated by filtration. The obtained solid was washed with water (50 mL) to obtain a target brown solid (yield 7.21 g, 99%) of 1- (2-naphthyl) -3-phenylpropenone.

  Synthesis Example 8

  Under an air atmosphere, 1- (2-naphthyl) -3-phenylpropenone (3.00 g, 0.0116 mol), 1- (4-bromophenacyl) pyridinium bromide (6.21 g, 0.0174 mol), ammonium acetate (17 91 g (0.232 mol) was suspended in a mixed solvent of acetic acid (120 mL) and dimethylformamide (120 mL), and stirred at 150 ° C. for 7 hours. After cooling to room temperature, 50 mL of water was added, and the precipitated solid was separated by filtration. The obtained solid is washed with water (50 mL) to give a target brown solid (yield 2.39 g, yield 47 of 2- (4-bromophenyl) -6- (2-naphthyl) -4-phenylpyridine). %) Got.

  Synthesis Example-9

  Under an argon stream, 2- (4-bromophenyl) -6- (2-naphthyl) -4-phenylpyridine (1.70 g, 3.90 mmol) was dissolved in tetrahydrofuran (47 mL) and stirred at -78.degree. To this, normal butyl lithium (normal hexane solution, 5.25 mmol) was added dropwise and stirred, and then triisopropyl borate (1.20 mL, 5.23 mmol) was further added and stirred for 19 hours. After stirring, 4 M aqueous sodium hydroxide solution (3.5 mL, 14 mmol) was added and stirred for 50 minutes. Water was added to the reaction solution, and extracted with ethyl acetate (120 mL). The organic layer was washed twice with saturated aqueous sodium chloride solution, and the organic layer and the aqueous layer were separated. After dehydrating the organic layer using magnesium sulfate, the target 4-{[6- (2-naphthyl) -4-phenyl] pyridin-2-yl} phenyl is obtained by concentrating the low boiling point components from the organic layer under reduced pressure. A pale yellow solid (yield 1.56 g, 100% yield) of boronic acid was obtained.

  Example 3

  Under an argon stream, 4-{[6- (2-naphthyl) -4-phenyl] pyridin-2-yl} phenylboronic acid (1.30 g, 3.24 mmol), 2- (3-bromophenyl) -4, 6-Diphenyl-1,3,5-triazine (0.97 g, 2.49 mmol) and tetrakis (triphenylphosphine) palladium (0.129 g, 0.11 mmol) were dissolved in tetrahydrofuran (50 mL). To this was added 2 M aqueous potassium carbonate solution (3.8 mL, 7.60 mmol) and stirred for another 29 h. After cooling to room temperature, water (80 mL) and methanol (20 mL) were added, and the precipitated solid was separated by filtration, and the solid was washed with water (50 mL), methanol (50 mL) and hexane (50 mL). The solid is dissolved in toluene (300 mL), filtered through Celite, and the filtrate is concentrated under reduced pressure to dryness, and further purified by recrystallization (toluene) to obtain the desired 2- {4 '-[6- (2) White powder (yield 1.03 g, yield of -naphthyl) -4-phenylpyridin-2-yl] biphenyl-3-yl} -4,6-diphenyl-1,3,5-triazine (compound A-722) 62%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.50-7.65 (m, 11 H), 7.71 (t, J = 8.0 Hz, 1 H), 7.82-7.86 (m , 2H), 7.90-7.97 (m, 4H), 8.00-8.05 (m, 3H), 8.09 (d, J = 1.4 Hz, 1 H), 8.41-8 45 (m, 3 H), 8. 71 (brs, 1 H), 8. 80-8. 84 (m, 5 H), 9. 11 (t, J = 2.0 Hz, 1 H).
The Tg of the obtained compound A-722 was 110 ° C.

  Synthesis Example-10

  In an air atmosphere, 4-chloroacetophenone (10.01 g, 0.0648 mol) and 4-bromobenzaldehyde (12.01 g, 0.0649 mol) are dissolved in acetic acid (100 mL), concentrated sulfuric acid (13.5 mL, 0.244 mol) ) Was added dropwise and stirred at room temperature for 22 hours. After stirring, 150 mL of water was added, and the precipitated solid was separated by filtration. The obtained solid is washed with water (200 mL) to give a yellow solid (yield 19.21 g, 92%) of the desired 3- (4-bromophenyl) -1- (4-chlorophenyl) propenone The

  Synthesis example-11

  Under an air atmosphere, 3- (4-bromophenyl) -1- (4-chlorophenyl) propenone (9.00 g, 0.0280 mmol), 1- (4-chlorophenacyl) pyridinium bromide (13.13 g, 0.0420 mol) ), Ammonium acetate (43.26 g, 0.561 mol) was suspended in a mixed solvent of acetic acid (120 mL) and dimethylformamide (50 mL), and stirred at 150 ° C. for 17 hours. After cooling to room temperature, water (350 mL) and methanol (50 mL) were added, and the precipitated solid was separated by filtration. The obtained solid is washed with water (300 mL) and methanol (100 mL) to give a white solid (yield 11.85 g) of the target 4- (4-bromophenyl) -2,6-bis (4-chlorophenyl) pyridine. , 93% yield).

  Synthesis example-12

  Under an argon stream, 4- (4-bromophenyl) -2,6-bis (4-chlorophenyl) pyridine (5.00 g, 11.0 mmol) was dissolved in tetrahydrofuran (55 mL) and stirred at -78.degree. To this, normal butyl lithium (normal hexane solution, 14.43 mmol) was added dropwise and stirred for 3 hours, and then triisopropyl borate (3.4 mL, 14.8 mmol) was further added and stirred for 19 hours. After stirring, 4 M aqueous sodium hydroxide solution (8.0 mL, 14 mmol) was added and stirred for 45 minutes. Water was added to the reaction solution and extracted with ethyl acetate (100 mL). The organic layer was washed with water and the organic and aqueous layers were separated. The organic layer is dehydrated using magnesium sulfate, and the low-boiling point component is concentrated under reduced pressure from the organic layer to give the desired 4- [2,6-bis (4-chlorophenyl) pyridin-4-yl] phenylboronic acid. A yellow solid (yield 4.23 g, 92%) was obtained.

  Synthesis Example-13

  Under an argon stream, 4- [2,6-bis (4-chlorophenyl) pyridin-4-yl] phenylboronic acid (3.89 g, 9.26 mmol), 2- (3-bromophenyl) -4,6-diphenyl -1,3,5-Triazine (1.55 g, 3.99 mmol), tetrakis (triphenylphosphine) palladium (0.140 g, 0.12 mmol) were dissolved in tetrahydrofuran (50 mL). To this, 2 M aqueous potassium carbonate solution (6.0 mL, 12.0 mmol) was added and stirred for 17 hours. After cooling to room temperature, water (40 mL) and methanol (10 mL) were added, and the precipitated solid was separated by filtration, and the solid was washed with water (50 mL), methanol (50 mL) and hexane (50 mL). The solid was suspended in toluene (210 mL), charged with silica gel and filtered while hot, and the filtrate was concentrated under reduced pressure. Furthermore, the desired 2- {4 '-[2,6-bis (4-chlorophenyl) pyridin-4-yl] biphenyl-3-yl} -4,6-diphenyl can be obtained by purifying twice by recrystallization (toluene). A white powder (yield 1.64 g, 60% yield) of -1,3,5-triazine was obtained.

  Example 4

  Under an argon stream, 2- {4 '-[2,6-bis (4-chlorophenyl) pyridin-4-yl] biphenyl-3-yl} -4,6-diphenyl-1,3,5-triazine (1. 02 g, 1.49 mmol), 3-pyridineboronic acid (1.10 g, 8.95 mmol), palladium acetate (37.3 mg, 0.17 mmol), 2-dicyclohexylphosphino-2 ', 4', 6'-tri Isopropylbiphenyl (79.0 mg, 0.17 mmol) was suspended in tetrahydrofuran (50 mL), 2 M aqueous potassium carbonate solution (5.8 mL, 11.6 mmol) was added dropwise, and the mixture was stirred at 80 ° C. for 65 hours. After cooling to room temperature, water (50 mL), methanol (10 mL) and hexane (20 mL) were added, and the precipitated solid was separated by filtration. The resulting solid was washed with water (50 mL), methanol (50 mL), hexane (50 mL). Furthermore, the desired 2- (4 '-{2,6-bis [4- (3-pyridyl) phenyl] pyridin-4-yl} biphenyl-3-yl) -4 can be obtained by further purification with recrystallization (toluene). An off-white solid (yield 0.55 g, 48%) of 6,6-diphenyl-1,3,5-triazine (compound A-155) was obtained.

  Tg of obtained compound A-155 was 139 degreeC.

  Synthesis example-14

  In an air atmosphere, 4-bromoacetophenone (14.18 g, 0.0712 mol) and 4-chlorobenzaldehyde (10.00 g, 0.0711 mol) are dissolved in acetic acid (100 mL), concentrated sulfuric acid (13.5 mL, 0.244 mol) ) Was added dropwise and stirred at room temperature for 48 hours. After stirring, 150 mL of water was added, and the precipitated solid was separated by filtration. The obtained solid is washed with water (200 mL) to give a yellow solid (yield 21.14 g, 92%) of the target 1- (4-bromophenyl) -3- (4-chlorophenyl) propenone. The

  Synthesis example-15

Under an air atmosphere, 1- (4-bromophenyl) -3- (4-chlorophenyl) propenone (10.00 g, 0.0311 mmol), 1- (4-chlorophenacyl) pyridinium bromide (13.58 g, 0.0434 mol) ), Ammonium acetate (48.33 g, 0.627 mol) was suspended in a mixed solvent of acetic acid (130 mL) and dimethylformamide (70 mL), and stirred at 150 ° C. for 25 hours. After cooling to room temperature, water (300 mL) was added, and the precipitated solid was separated by filtration. The obtained solid is washed with water (300 mL) and methanol (100 mL) to give a white solid (yield 13.09 g) of desired 2- (4-bromophenyl) -4,6-bis (4-chlorophenyl) pyridine. , 93% yield).

  Synthesis example-16

  Under an argon stream, 2- (4-bromophenyl) -4,6- (4-chlorophenyl) pyridine (5.00 g, 11.0 mmol) was dissolved in tetrahydrofuran (55 mL) and stirred at -78 ° C. To this, normal butyl lithium (normal hexane solution, 14.43 mmol) was added dropwise and stirred for 3 hours, and then triisopropyl borate (3.6 mL, 15.7 mmol) was further added and stirred at room temperature for 22 hours. After stirring, 4 M aqueous sodium hydroxide solution (8.0 mL, 14 mmol) was added and stirred at room temperature for 30 minutes. Water was added to the reaction solution and extracted with ethyl acetate (100 mL). The organic layer was washed with water and the organic and aqueous layers were separated. The organic layer is dehydrated using magnesium sulfate, and then the low-boiling point component is concentrated under reduced pressure from the organic layer to obtain the desired 4- [4,6-bis (4-chlorophenyl) pyridin-2-yl] phenylboronic acid. A yellow solid (yield 4.44 g, 96% yield) was obtained.

  Synthesis example-17

Under an argon stream, 4- [4,6- (4-chlorophenyl) pyridin-2-yl] phenylboronic acid (2.73 g, 6.50 mmol), 2- (3-bromophenyl) -4,6-diphenyl- 1,3,5-Triazine (1.56 g, 4.02 mmol), tetrakis (triphenylphosphine) palladium (0.143 g, 0.12 mmol) were dissolved in tetrahydrofuran (50 mL). To this was added 2 M aqueous potassium carbonate solution (6.0 mL, 12.0 mmol) and stirred at 75 ° C. for 68 hours. After cooling to room temperature, water (50 mL)
Methanol (30 mL) was added, and the precipitated solid was filtered off, and the solid was washed with water (50 mL), methanol (50 mL) and hexane (50 mL). The solid was dissolved in toluene (400 mL), charged with silica gel and filtered while hot, and the filtrate was concentrated under reduced pressure. Furthermore, the desired 2- {4 '-[4,6-bis (4-chlorophenyl) pyridin-2-yl] biphenyl-3-yl} -4,6-diphenyl can be obtained by purifying twice by recrystallization (toluene). A white powder of -1,3,5-triazine (yield 1.27 g, 46%) was obtained.

  Example 5

  Under an argon stream, 2- {4 '-[4,6-bis (4-chlorophenyl) pyridin-2-yl] biphenyl-3-yl} -4,6-diphenyl-1,3,5-triazine (1. 97 g (2.88 mmol), 3-pyridineboronic acid (1.45 g, 11.8 mmol), palladium acetate (26.3 mg, 0.12 mmol), 2-dicyclohexylphosphino-2 ', 4', 6'-tri Isopropyl biphenyl (0.115 g, 0.24 mmol) was suspended in tetrahydrofuran (100 mL), 2 M aqueous potassium carbonate solution (11.7 mL, 23.4 mmol) was added dropwise, and stirred at 75 ° C. for 25 hours. After cooling to room temperature, water (50 mL) and methanol (30 mL) were added, and the precipitated solid was separated by filtration. The resulting solid was washed with water (50 mL), methanol (50 mL), hexane (50 mL). The solid was dissolved in toluene (500 mL), filtered through celite, and the filtrate was concentrated under reduced pressure. Further purification by recrystallization (toluene) gives the desired 2- (4 '-{4,6-bis [4- (3-pyridyl) phenyl] pyridin-2-yl} biphenyl-3-yl) -4. An off-white solid (yield 1.56 g, 70%) of 6,6-diphenyl-1,3,5-triazine (compound A-515) was obtained.

Tg of obtained compound A-515 was 139 degreeC.
Synthesis Example-18

  Under an argon stream, 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (10.0 g, 25.8 mmol), bispinacolate diboron (7.19 g, 28.3 mmol) Dissolve [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride (0.94 g, 1.29 mmol) and potassium acetate (7.48 g, 76.2 mmol) in dimethyl sulfoxide (200 mL) And stirred at 80 ° C. for 4 hours. After allowing to cool, water (100 mL) was added to the reaction solution, and extracted with ethyl acetate (300 mL) and hexane (100 mL). The organic layer was washed with brine, and the organic and aqueous layers were separated. The organic layer was dehydrated using magnesium sulfate, and then the low boiling point components were evaporated under reduced pressure from the organic layer to obtain a dried solid. Further purification by column chromatography (hexane: chloroform) gives 2- [3-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4. A milky white solid (yield 7.40 g, 66% yield) of 6,6-diphenyl-1,3,5-triazine was obtained.

  Synthesis example-19

  Under an air atmosphere, potassium hydroxide was suspended in a mixed solvent of ethanol (10 mL) and water (20 mL), 1-acetonaphthone (5.00 g, 0.0294 mmol) was added dropwise, and the mixture was stirred at 0 ° C. for 10 minutes. After stirring, a solution of 4-bromobenzaldehyde (5.44 g, 0.0294 mmol) in ethanol (10 mL) was added and stirred at room temperature for 16 hours. Then, water (200 mL) was added to the reaction solution, and the precipitated solid was separated by filtration. The obtained solid is washed with water (200 mL) to give a yellow solid (yield 9.78 g, 99%) of the objective 1- (1-naphthyl) -3- (4-bromophenyl) propenone. The

  Synthesis example-20

Under an air atmosphere, 1- (1-naphthyl) -3- (4-bromophenyl) propenone (3.00 g, 8.90 mmol), 1-phenacylpyridinium bromide (3.71 g, 0.0133 mol), and ammonium acetate (13.81 g, 0.179 mol) was dissolved in a mixed solvent of acetic acid (110 mL) and dimethylformamide (20 mL), and stirred at 150 ° C. for 16 hours. After cooling to room temperature, water (250 mL) was added, and the precipitated solid was separated by filtration. The resulting solid is washed with water (200 mL) to give the target 4- (4-bromophenyl) -2- (1-naphthyl) -6-phenylpyridine as a brown solid (yield 3.32 g, yield 86). %) Got.

  Example 6

  Under an argon stream, 4- (4-bromophenyl) -2- (1-naphthyl) -6-phenylpyridine (1.59 g, 3.65 mmol), 2- [3-{(4,4,5,5-) Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5-triazine (1.91 g, 4.38 mmol), and tetrakis (triphenylphosphine) palladium (0.21 g, 0.183 mmol) was dissolved in 1,4-dioxane (80 mL). To this was added 2 M aqueous potassium carbonate solution (5.6 mL, 11.2 mmol), and the mixture was further stirred at 100 ° C. for 16 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure, water (100 mL) was added, and the precipitated solid was separated by filtration and washed with water (80 mL), methanol (80 mL) and hexane (80 mL). Furthermore, the target 2- {4 '-[2- (1-naphthyl) -6-phenylpyridin-4-yl] biphenyl-3-yl} -4,6- is obtained by performing recrystallization (ethyl acetate) five times. A brown powder (yield 1.02 g, 42%) of diphenyl-1,3,5-triazine (compound A-4) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.43-7.66 (m, 12 H), 7.70 (t, J = 7.6 Hz, 1 H) 7.80 (dd, J = 1. 1 Hz, 7.2 Hz, 1 H), 7.85 (d, J = 1.5 Hz, 1 H), 7.90-7.98 (m, 7 H), 8. 10 (d, J = 1.5 Hz, 1 H) ), 8.20-8.23 (m, 2H), 8.34 (m, 1H), 8.79-8.83 (m, 5H), 9.07 (t, J = 1.7 Hz, 1 H) ).
Synthesis example-21

In an air atmosphere, 4-bromoacetophenone (5.00 g, 0.0251 mol) and 1-naphthaldehyde (3.98 g, 0.0255 mol) are dissolved in acetic acid (100 mL), concentrated sulfuric acid (7.0 mL, 0. 0 127 mol) was added dropwise and stirred at room temperature for 15 hours. Then, 300 mL of water was added, and the precipitated solid was separated by filtration. The obtained solid is washed with water (100 mL) and methanol (30 mL) to obtain a yellow solid (yield 5.98 g, yield) of the desired 1- (4-bromophenyl) -3- (1-naphthyl) propenone. 71%).

  Synthesis Example-22

  1- (4-bromophenyl) -3- (1-naphthyl) propenone (4.00 g, 0.0119 mol), 1-phenacylpyridinium bromide (4.95 g, 0.0178 mol), and ammonium acetate under an air atmosphere (18.33 g, 0.238 mol) was dissolved in a mixed solvent of acetic acid (50 mL) and dimethylformamide (40 mL), and stirred at 150 ° C. for 7 hours. After cooling to room temperature, water (250 mL) was added, and the precipitated solid was separated by filtration. The resulting solid is washed with water (200 mL) and methanol (150 mL) to give a brown solid (yield 3.3) of the desired 2- (4-bromophenyl) -4- (1-naphthyl) -6-phenylpyridine. 90 g, yield 75%) were obtained.

  Example 7

Under a stream of argon, 2- (4-bromophenyl) -4- (1-naphthyl) -6-phenylpyridine (1.00 g, 2.29 mmol), 2- [3-{(4,4,5,5-) Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5-triazine (1.20 g, 2.75 mmol), and tetrakis (triphenylphosphine) palladium (0.14 g, 0.115 mmol) was dissolved in 1,4-dioxane (50 mL). To this was added 2 M aqueous potassium carbonate solution (3.4 mL, 6.8 mmol), and the mixture was further stirred at 100 ° C. for 21 hours. After cooling to room temperature, the reaction solution is concentrated under reduced pressure, water (50 mL) and methanol (20 mL) are added, the precipitated solid is separated by filtration, and the solid is extracted with water (70 mL), methanol (70 mL) and hexane (70 mL). It was washed. The solid was dissolved in toluene (200 mL), filtered through celite, and the filtrate was concentrated under reduced pressure. The resulting solid was suspended in ethyl acetate (150 mL) and filtered. The solid precipitated from this filtrate is washed with methanol (50 mL) to give the desired 2- {4 '-[4- (1-naphthyl) -6-phenylpyridin-2-yl] biphenyl-3-yl}. A brown powder (yield 0.93 g, 61%) of -4,6-diphenyl-1,3,5-triazine (compound A-364) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.44-7.66 (m, 13 H), 7.69 (t, J = 7.7 Hz, 1 H), 7.88-7.95 (m) , 5H), 7.99 (t, J = 7.4 Hz, 3 H) 8.25-8.28 (m, 2 H), 8.40 (d, J = 8.4 Hz, 2 H), 8.78- 8.83 (m, 5H), 9.09 (t, J = 1.8 Hz, 1 H).
Synthesis example-23

  In an air atmosphere, 2-acetonaphthone (6.00 g, 0.0353 mol) and 1-naphthaldehyde (5.61 g, 0.0359 mol) are dissolved in acetic acid (100 mL), concentrated sulfuric acid (8.0 mL, 0.145 mol) ) Was added dropwise and stirred at room temperature for 15 hours. Then, 300 mL of water was added, and the precipitated solid was separated by filtration. The resulting solid is washed with water (150 mL) and methanol (30 mL) to give the desired 1- (2-naphthyl) -3- (1-naphthyl) propenone as an orange solid (yield 9.49 g, yield 87). %) Got.

  Synthesis Example-24

  1- (2-naphthyl) -3- (1-naphthyl) propenone (5.00 g, 0.0162 mol), 1- (4-bromophenacyl) pyridinium bromide (8.68 g, 0.0243 mol) under an air atmosphere, and Ammonium acetate (24.98 g, 0.324 mol) was dissolved in a mixed solvent of acetic acid (65 mL) and dimethylformamide (40 mL) and stirred at 150 ° C. for 7 hours. After cooling to room temperature, water (250 mL) was added, the precipitated solid was separated by filtration, and the obtained solid was washed with water (200 mL) and methanol (150 mL). Further, the washed solid is recrystallized (methanol) to give a brown solid (yield 2.45 g) of desired 2- (4-bromophenyl) -4- (1-naphthyl) -6- (2-naphthyl) pyridine. 31% yield was obtained.

  Example 8

  Under an argon stream, 2- (4-bromophenyl) -4- (1-naphthyl) -6- (2-naphthyl) pyridine (1.20 g, 2.47 mmol), 2- [3-{(4,4,6) 5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5-triazine (1.42 g, 2.75 mmol), and tetrakis Phenyl phosphine) palladium (0.17 g, 0.144 mmol) was dissolved in 1,4-dioxane (50 mL). To this was added 2 M aqueous potassium carbonate solution (3.7 mL, 7.4 mmol), and the mixture was further stirred at 100 ° C. for 21 hours. After cooling to room temperature, the reaction solution is concentrated under reduced pressure, water (50 mL) and methanol (20 mL) are added, the precipitated solid is separated by filtration, and the solid is extracted with water (70 mL), methanol (70 mL) and hexane (70 mL). It was washed. The solid was dissolved in toluene (300 mL), filtered through celite, and the filtrate was concentrated under reduced pressure. The resulting solid is recrystallized (ethyl acetate / methanol) to give the desired 2- {4 '-[4- (1-naphthyl) -6- (2-naphthyl) pyridin-2-yl] biphenyl-3. Y-yl} -4,6-diphenyl-1,3,5-triazine (compound A-365) was obtained as a brown powder (yield 0.93 g, 61%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.51-7.67 (m, 13 H), 7.70 (t, J = 7.7 Hz, 1 H), 7.89-8.05 (m , 10H), 8.42-8.46 (m, 3H), 8.71 (d, J = 1.1 Hz, 1H), 8.79-8.84 (m, 5H), 9.10 (t) , J = 1.7 Hz, 1 H).
The Tg of the obtained compound A-365 was 127 ° C.

  Example 9

  Under a stream of argon, 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (1.50 g, 3.86 mmol), 4- (4,6-diphenylpyridin-2-yl) Phenylboronic acid (1.63 g, 4.64 mmol), tetrakistriphenylphosphine palladium (134 mg, 1.16 mmol) and potassium carbonate (1.60 g, 11.6 mmol) in a mixture of tetrahydrofuran (83 mL) and water (11 mL) Suspended in solvent. The resulting mixture was stirred at 70 ° C. for 25 hours. After cooling to room temperature, water (100 mL) was added, and the precipitated solid was separated by filtration, and the solid was washed with water, methanol and hexane. The resulting solid is recrystallized (toluene) to obtain the desired product 4,6-diphenyl-2- [4 '-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl] -1 An off-white solid (yield 1.79 g, 99%) of 3,5-triazine (A-721) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.43-7.64 (m, 12 H), 7.68 (t, J = 8.1 Hz, 1 H), 7.78 (dd, J = 8 .5 Hz, 1.5 Hz, 2 H), 7.89-7.93 (m, 4 H), 7.98 (d, J = 1.4 Hz, 1 H), 8.23 (dd, J = 8.6 Hz, 1.4 Hz, 2 H), 8.37 (d, J = 8.5 Hz, 2 H), 8.77-8.82 (m, 5 H), 9.08 (t, J = 1.6 Hz, 1 H).
The Tg of the obtained compound A-721 was 102 ° C.

  Synthesis example-25

  In an air atmosphere, 4′-bromoacetophenone (1.94 g, 9.70 mmol) and 9-phenanthrenecarbaldehyde (2.00 g, 9.70 mmol) are dissolved in acetic acid (50 mL), concentrated sulfuric acid (3.0 mL, 0.054 mol) was dripped and it stirred at room temperature for 21 hours. Then, water (200 mL) and methanol (50 mL) were added, and the precipitated solid was separated by filtration. The resulting solid was washed with water (100 mL), methanol (50 mL). This solid is poured into a mixed solvent of methanol (300 mL) and hexane (50 mL) and stirred, and then the solid is separated by filtration to obtain the desired 1- (4-bromophenyl) -3- (9-phenanthryl) propenone. A yellow solid (yield 2.7 g, 72%) was obtained.

  Synthesis Example-26

  1- (4-bromophenyl) -3- (9-phenanthryl) propenone (2.7 g, 6.97 mmol), 1-phenacyl pyridinium bromide (2.97 g, 0.0107 mol), and ammonium acetate under an air atmosphere (10.75 g, 0.139 mol) was dissolved in a mixed solvent of acetic acid (50 mL) and dimethylformamide (28 mL), and stirred at 150 ° C. for 19 hours. After cooling to room temperature, water (400 mL) was added, the precipitated solid was separated by filtration, and the obtained solid was washed with water (100 mL) and methanol (100 mL). The washed solid was suspended in methanol (200 mL) and stirred to further wash the solid. The obtained solid is purified by column chromatography (chloroform: hexane) to give a white solid (yield 0.40 g) of the target 2- (4-bromophenyl) -4- (9-phenanthryl) -6-phenylpyridine. , Yield 12%).

  Example 10

  Under an argon stream, 2- (4-bromophenyl) -4- (9-phenanthryl) -6-phenylpyridine (0.55 g, 1.14 mmol), 2- [3-{(4,4,5,5-) Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5-triazine (0.62 g, 1.42 mmol), and tetrakis (triphenylphosphine) palladium (0.080 g, 0.069 mmol) was dissolved in tetrahydrofuran (11 mL). To this, 2 M aqueous potassium carbonate solution (1.7 mL, 3.4 mmol) was added, and the mixture was further stirred at 80 ° C. for 50 hours. After cooling to room temperature, water (20 mL) and methanol (1 mL) were added, and the precipitated solid was separated by filtration, and the solid was washed with water (60 mL), methanol (120 mL) and hexane (60 mL). The target solid 2- {4 '-[4- (9-phenanthryl) -6-phenylpyridin-2-yl] biphenyl-3-yl} -4,6 is obtained by recrystallization (toluene) of the obtained solid. A white powder (yield 0.63 g, 77%) of diphenyl-1,3,5-triazine (compound A-367) was obtained.

¹ H-NMR (CDCl 3) δ (ppm): 7.46 to 7.77 (m, 14 H), 7.85 (s, 1 H), 7.91 to 8.03 (m, 7 H), 8.27 -8.29 (d, J = 7.0 Hz, 2 H), 8.40-8.43 (d, J = 8.6 Hz, 2 H), 8.77-8.86 (m, 7 H), 9. 09 (t, J = 1.7 Hz, 1 H).
Synthesis Example-27

  Under an air atmosphere, potassium hydroxide (5.57 g, 0.099 mol) is suspended in a mixed solvent of ethanol (30 mL) and water (60 mL), and 2-acetylpyridine (10.00 g, 0.0825 mol) is added dropwise. Stirred at 0 ° C. for 35 minutes. After stirring, benzaldehyde (8.76 g, 0.0825 mol) was added and stirred at room temperature for 4 hours. Then, water (150 mL) was added to the reaction solution, and the precipitated solid was separated by filtration. The obtained solid was washed with water (200 mL) to give a target yellow solid (yield 16.98 g, 98%) of 1- (2-pyridyl) -3-phenylpropenone.

  Synthesis example-28

  Under an air atmosphere, 1- (2-pyridyl) -3-phenylpropenone (8.51 g, 0.0407 mol), 1- (4-bromophenacyl) pyridinium bromide (19.82 g, 0.0555 mol), and ammonium acetate ( 58.22 g, 0.755 mol) was dissolved in a mixed solvent of acetic acid (150 mL) and dimethylformamide (150 mL), and stirred at 150 ° C. for 15 hours. After cooling to room temperature, water (250 mL) was added, the precipitated solid was separated by filtration, and the obtained solid was washed with water (200 mL). The washed solid was dissolved in ethyl acetate (200 mL), added with silica gel and filtered. The obtained filtrate is concentrated under reduced pressure to obtain a target brown solid (yield 10.00 g, 63%) of 2- (4-bromophenyl) -4-phenyl-6- (2-pyridyl) pyridine. The

  Synthesis example-29

Under an argon stream, 2- (4-bromophenyl) -4-phenyl-6- (2-pyridyl) pyridine (10.00 g, 25.8 mmol) was dissolved in tetrahydrofuran (200 mL) and stirred at -78 ° C. To this, normal butyl lithium (normal hexane solution, 31.0 mmol) was added dropwise, and after stirring for 2 hours, triisopropyl borate (7.2 mL, 31.4 mmol) was further added, and the mixture was stirred at room temperature for 17 hours. Then, 4 M aqueous sodium hydroxide solution (12.0 mL, 48 mmol) was added and stirred at room temperature for 1 hour. The precipitated solid was washed with water (200 mL) and hexane (200 mL) to give a yellow solid (Yield 3 of the objective 4- [4-phenyl-6- (2-pyridyl) pyridin-2-yl] phenylboronic acid). .25 g (36% yield) were obtained.

  Example 11

  Under an argon stream, 4- [4-phenyl-6- (2-pyridyl) pyridin-2-yl] phenylboronic acid (3.00 g, 8.53 mmol), 2- (3-bromophenyl) -4,6- Diphenyl-1,3,5-triazine (2.76 g, 7.11 mmol) and tetrakis (triphenylphosphine) palladium (0.247 g, 0.214 mmol) were dissolved in tetrahydrofuran (86 mL). To this, 2 M aqueous potassium carbonate solution (12.8 mL, 25.60 mmol) was added and stirred at 80 ° C. for 18 hours. After cooling to room temperature, water (90 mL) and methanol (10 mL) were added, and the precipitated solid was separated by filtration. The resulting solid was washed with water (60 mL), methanol (60 mL), hexane (60 mL). The solid is purified by recrystallization (toluene) twice to give the desired 2- {4 '-[4-phenyl-6- (2-pyridyl) pyridin-2-yl] biphenyl-3-yl} -4, A white powder (yield 3.34 g, 76%) of 6-diphenyl-1,3,5-triazine (compound A-743) was obtained.

¹ H-NMR (CDCl 3) δ (ppm): 7.36 to 7.39 (m, 1 H), 7.47 to 7.66 (m, 9 H), 7.71 (t, J = 7.6 Hz, 1H), 7.84-7.95 (m, 6H), 8.09 (d, J = 1.5 Hz, 1 H), 8.39 (d, J = 8.3 Hz, 2 H), 8.69 (8 d, J = 1.5 Hz, 1 H), 8.74-8.84 (m, 7 H), 9.10 (t, J = 1.7 Hz, 1 H).
Synthesis example-30

In an air atmosphere, 4′-bromoacetophenone (10.06 g, 0.0505 mol) and biphenyl-4-carboxaldehyde (9.17 g, 0.0503 mmol) are dissolved in acetic acid (250 mL) and concentrated sulfuric acid (12.5 mL) , 0.225 mol) was added dropwise and stirred at room temperature for 25 hours. Then, water (500 mL) was added and the precipitated solid was separated by filtration. The resulting solid is washed with water (100 mL) and methanol (100 mL) to give the target 1- (4-bromophenyl) -3- (4-biphenyl) propenone as a white solid (yield 11.61 g, yield) 63%).

  Synthesis example-31

  1- (4-bromophenyl) -3- (4-biphenyl) propenone (11.52 g, 0.0317 mol), 1-phenacylpyridinium bromide (13.24 g, 0.0476 mol), and ammonium acetate under an air atmosphere (48.88 g, 0.634 mol) was dissolved in a mixed solvent of acetic acid (161 mL) and dimethylformamide (154 mL), and stirred at 150 ° C. for 2 hours. After cooling to room temperature, water (300 mL) was added, and the precipitated solid was separated by filtration. The resulting solid is washed with water (300 mL), methanol (300 mL) and hexane (100 mL) to give the desired white of 4- (4-biphenyl) -2- (4-bromophenyl) -6-phenylpyridine. A solid (yield 13.33 g, 91% yield) was obtained.

  Synthesis example-32

  Under an argon stream, 4- (4-biphenyl) -2- (4-bromophenyl) -6-phenylpyridine (13.20 g, 28.6 mmol) was dissolved in tetrahydrofuran (250 mL) and stirred at -78 ° C. To this, normal butyl lithium (normal hexane solution, 34.7 mmol) was added dropwise, and after stirring for 2 hours, triisopropyl borate (7.9 mL, 34.4 mmol) was further added, and the mixture was stirred at room temperature for 17 hours. After stirring, 4 M aqueous sodium hydroxide solution (16.0 mL, 64 mmol) was added and stirred at room temperature for 1 hour. The precipitated solid is washed with water (300 mL) and hexane (300 mL) to give the target 4- [4- (4-biphenyl) -6-phenylpyridin-2-yl] phenylboronic acid as a white solid (yield 9). .92 g (yield 81%) were obtained.

  Example 12

  Under an argon stream, 4- [4- (4-biphenyl) -6-phenylpyridin-2-yl] phenylboronic acid (5.31 g, 12.43 mmol), 2- (3-bromophenyl) -4,6- Diphenyl-1,3,5-triazine (4.30 g, 11.08 mmol) and tetrakis (triphenylphosphine) palladium (0.387 g, 0.335 mmol) were dissolved in tetrahydrofuran (56 mL). To this, 2 M aqueous potassium carbonate solution (17.0 mL, 34.00 mmol) was added and stirred at 80 ° C. for 28 hours. After cooling to room temperature, water (40 mL) and methanol (3 mL) were added, and the precipitated solid was separated by filtration. The resulting solid was washed with water (120 mL), methanol (240 mL), hexane (120 mL). The solid is purified by recrystallization (toluene) to give the desired 2- {4 '-[4- (4-biphenyl) -6-phenylpyridin-2-yl] biphenyl-3-yl} -4,6- A white powder (yield 6.25 g, 82% yield) of diphenyl-1,3,5-triazine (compound A-429) was obtained.

¹ H-NMR (CDCl 3) δ (ppm): 7.39-7.43 (m, 1 H), 7.46-7.73 (m, 14 H), 7.78-7. 90 (m, 4 H) , 7.92-7.96 (m, 3H), 7.98 (d, J = 1.3 Hz, 1 H), 8.04 (d, J = 1.3 Hz, 1 H), 8.26 (d, J = 6.9 Hz, 2 H), 8. 40 (d, J = 8.4 Hz, 2 H), 8.79-8.84 (m, 5 H), 9. 10 (t, J = 1.7 Hz, 1 H) ).
Synthesis example-33

  In an air atmosphere, 4-acetylbiphenyl (10.06 g, 0.0513 mol) and benzaldehyde (5.41 g, 0.0530 mmol) are dissolved in acetic acid (250 mL) and concentrated sulfuric acid (12.5 mL, 0.225 mol) It was added dropwise and stirred at room temperature for 25 hours. Then, water (500 mL) was added and the precipitated solid was separated by filtration. The resulting solid is washed with water (100 mL) and methanol (100 mL) to give a pale yellow solid of the objective 1- (4-biphenyl) -3-phenylpropenone (yield 8.35 g, 57%) I got

  Synthesis example-34

  Under an air atmosphere, 1- (4-biphenyl) -3-phenylpropenone (8.33 g, 0.0293 mol), 1- (4-bromophenacyl) pyridinium bromide (15.67 g, 0.0434 mol), and ammonium acetate ( 45.39 g (0.589 mol) was dissolved in a mixed solvent of acetic acid (116 mL) and dimethylformamide (111 mL), and stirred at 150 ° C. for 2 hours. After cooling to room temperature, water (220 mL) is added, the precipitated solid is separated by filtration, and the obtained solid is washed with water (300 mL), methanol (100 mL) and hexane (100 mL) to obtain the desired 2- A pale yellow solid (yield 11.98 g, 88%) of (4-biphenyl) -6- (4-bromophenyl) -4-phenylpyridine was obtained.

  Synthesis example-35

  Under an argon stream, 2- (4-biphenyl) -6- (4-bromophenyl) -4-phenylpyridine (11.95 g, 25.8 mmol) was dissolved in tetrahydrofuran (226 mL) and stirred at -78.degree. To this, normal butyl lithium (normal hexane solution, 31.4 mmol) was added dropwise, and after stirring for 2 hours, triisopropyl borate (7.2 mL, 31.4 mmol) was further added and stirred at room temperature for 21 hours. After stirring, 4 M aqueous sodium hydroxide solution (14.0 mL, 56 mmol) was added and stirred at room temperature for 1 hour. The precipitated solid is washed with water (300 mL) and hexane (300 mL) to give a white solid of the target 4- [6- (4-biphenyl) -4-phenylpyridin-2-yl] phenylboronic acid (yield 5 .27 g, yield 48%) was obtained.

  Example 13

  Under an argon stream, 4- [6- (4-biphenyl) -4-phenylpyridin-2-yl] phenylboronic acid (5.20 g, 12.17 mmol), 2- (3-bromophenyl) -4,6- Diphenyl-1,3,5-triazine (4.30 g, 11.08 mmol) and tetrakis (triphenylphosphine) palladium (0.515 g, 0.445 mmol) were dissolved in tetrahydrofuran (55 mL). To this, 2 M aqueous potassium carbonate solution (17.0 mL, 34.00 mmol) was added and stirred at 80 ° C. for 28 hours. After cooling to room temperature, water (40 mL) and methanol (3 mL) were added, and the precipitated solid was separated by filtration. The resulting solid was washed with water (120 mL), methanol (240 mL), hexane (120 mL). The solid is purified by recrystallization (toluene) to give the desired 2- {4 '-[6- (4-biphenyl) -4-phenylpyridin-2-yl] biphenyl-3-yl} -4,6- A white powder (yield 6.72 g, 88%) of diphenyl-1,3,5-triazine (compound A-788) was obtained.

¹ H-NMR (CDCl 3) δ (ppm): 7.38-7.41 (m, 1 H), 7.47-7. 66 (m, 11 H), 7.68-7. 72 (m, 3 H) , 7.77-7.82 (m, 4H), 7.92-7.95 (m, 3H), 7.98-8.01 (dd, J = 9.7 Hz, 1.3 Hz, 2 H), 8.34 (d, J = 8.4 Hz, 2 H), 8.41 (d, J = 8.5 Hz, 2 H), 8.79-8.83 (m, 5 H), 9. 10 (t, J = 1.7 Hz, 1 H).
Synthesis example-36

In an air atmosphere, 4′-bromoacetophenone (12.5 g, 62.8 mmol) and 4-methylbenzaldehyde (8.43 g, 62.8 mmol) are dissolved in acetic acid (100 mL) and concentrated sulfuric acid (15 mL) is added dropwise. The mixture was stirred at room temperature for 26 hours. Then water (300 mL) was added and the precipitated solid was filtered off. The resulting solid is washed with water (100 mL) and methanol (100 mL) to give a pale yellow solid (Yield 9.86 g, 1- (4-bromophenyl) -3- (4-methylphenyl) propenone). Yield 50%).
Synthesis Example-37

In an air atmosphere, 4′-bromoacetophenone (25.0 g, 126 mmol) and 3,5-dimethylbenzaldehyde (15.1 g, 126 mmol) are dissolved in acetic acid (200 mL), concentrated sulfuric acid (30 mL) is added dropwise, and room temperature is achieved. The mixture was stirred for 24 hours. Then water (300 mL) was added and the precipitated solid was filtered off. The obtained solid is washed with water (100 mL) and methanol (100 mL) to give a pale yellow solid of the target 1- (4-bromophenyl) -3- (3,5-dimethylphenyl) propenone (yield 35. 4 g, yield 94%) were obtained.
Synthetic Example-38

In an air atmosphere, 2-acetylbenzofuran (3.00 g, 18.7 mmol) and 4-bromobenzaldehyde (3.47 g, 18.7 mmol) are dissolved in acetic acid (30 mL) and concentrated sulfuric acid (4.00 mL) is added dropwise And stirred at room temperature for 24 hours. Then water (30 mL) was added and the precipitated solid was filtered off. The resulting solid is washed with water (50 mL) and methanol (50 mL) to give a pale yellow solid (Yield 5.68 g, yield of the objective 1- (2-benzofuryl) -3- (4-bromophenyl) propenone). The rate is 93%).
Synthesis example-39

In an air atmosphere, p-bromoacetophenone (1.36 g, 6.84 mmol) and 2-benzofurancarbaldehyde (1.00 g, 6.84 mmol) are dissolved in acetic acid (10 mL) and concentrated sulfuric acid (1.33 mL) It was added dropwise and stirred at room temperature for 24 hours. Then water (20 mL) was added and the precipitated solid was filtered off. The obtained solid is washed with water (50 mL) and methanol (50 mL) to obtain a pale yellow solid (yield 2.14 g, yield of the objective 3- (2-benzofuryl) -1- (4-bromophenyl) propenone. The rate is 95%).
Synthesis example-40

1- (4-bromophenyl) -3- (4-methylphenyl) propenone (10.0 g, 32.2 mmol), 1-phenacylpyridinium bromide (12.9 g, 46.5 mmol), and acetic acid under an air atmosphere Ammonium (38.4 g, 498 mol) was dissolved in a mixed solvent of acetic acid (100 mL) and dimethylformamide (100 mL) and stirred at 150 ° C. for 15 hours. After cooling to room temperature, water (300 mL) is added, the precipitated solid is separated by filtration, and the obtained solid is washed with water (300 mL), methanol (100 mL) and hexane (100 mL) to obtain the desired 6- A pale yellow solid (yield 11.8 g, 89%) of (4-bromophenyl) -4- (4-methylphenyl) -2-phenylpyridine was obtained.
Synthesis example-41

1- (4-bromophenyl) -3- (3,5-dimethylphenyl) propenone (7.0 g, 22.2 mmol), 1-phenacylpyridinium bromide (8.87 g, 31.1 mmol) under an air atmosphere, And ammonium acetate (25.7 g, 333 mol) were dissolved in a mixed solvent of acetic acid (70 mL) and dimethylformamide (70 mL), and stirred at 150 ° C. for 15 hours. After cooling to room temperature, water (200 mL) is added, the precipitated solid is separated by filtration, and the obtained solid is washed with water (100 mL), methanol (100 mL) and hexane (100 mL) to obtain the desired 6- A pale yellow solid (yield 7.28 g, 79%) of (4-bromophenyl) -4- (3,5-dimethylphenyl) -2-phenylpyridine was obtained.
Synthesis example-42

1- (2-benzofuryl) -3- (4-bromophenyl) propenone (under air atmosphere)
1.00 g, 3.06 mmol), 1-phenacyl pyridinium bromide (1.28 g, 4.58 mmol), and ammonium acetate (3.53 g, 45.8 mmol) in acetic acid (30 mL), and dimethylformamide (30 mL) It was dissolved in a mixed solvent and stirred at 150 ° C. for 13 hours. After cooling to room temperature, water (100 mL) is added, the precipitated solid is separated by filtration, and the obtained solid is washed with water (100 mL), methanol (100 mL) and hexane (100 mL) to obtain the desired 2- A pale yellow solid (yield 0.810 g, 62%) of (2-benzofuryl) -6- (4-bromophenyl) -4-phenylpyridine was obtained.
Synthesis example-43

Under air atmosphere, 3- (2-benzofuryl) -1- (4-bromophenyl) propenone (0.50 g, 1.53 mmol), 1-phenacylpyridinium bromide (638 mg, 2.29 mmol), and ammonium acetate (1 .77 g (22.9 mmol) was dissolved in a mixed solvent of acetic acid (15 mL) and dimethylformamide (15 mL), and stirred at 140 ° C. for 24 hours. After cooling to room temperature, water (200 mL) is added, the precipitated solid is separated by filtration, and the obtained solid is washed with water (100 mL), methanol (100 mL) and hexane (100 mL) to obtain the desired 4- A pale yellow solid (yield 471 mg, 73%) of (2-benzofuryl) -2- (4-bromophenyl) -6-phenylpyridine was obtained.
Example 14

Under a nitrogen stream, 2- [3-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5- Triazine (150 mg, 0.345 mmol), 6- (4-bromophenyl) -4- (4-methylphenyl) -2-phenylpyridine (138 mg, 0.345 mmol), and tetrakis (triphenylphosphine) palladium (12. 0 mg (0.0104 mmol) was suspended in tetrahydrofuran (6 mL). To this was added 2 M aqueous potassium carbonate solution (0.517 mL, 1.04 mmol) and stirred at 80 ° C. for 12 hours. After cooling to room temperature, water (40 mL) was added, and the precipitated solid was separated by filtration. The resulting solid is washed with water (30 mL), methanol (30 mL) and hexane (30 mL) to give the desired 2- {4 '-[4- (4-methylphenyl) -6-phenylpyridin-2-yl A white powder (yield 203 mg, 93%) of biphenyl-3-yl} -4,6-diphenyl-1,3,5-triazine (compound A-1117) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 2.51 (s, 3 H), 7.41 (d, J = 7.5 Hz, 2 H), 7.51-7.75 (m, 13 H), 7.94-8.02 (m, 4 H), 8.29 (d, J = 7.5 Hz, 2 H), 8.42 (d, J = 8.4 Hz, 2 H), 8.84-8.87 (M, 5 H), 9. 13 (brs, 1 H).
Example 15

  Under a nitrogen stream, 2- [3-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5- Triazine (150 mg, 0.345 mmol), 6- (4-bromophenyl) -4- (3,5-dimethylphenyl) -2-phenylpyridine (143 mg, 0.345 mmol), and tetrakis (triphenylphosphine) palladium ( 12.0 mg (0.0104 mmol) was suspended in tetrahydrofuran (6 mL). To this was added 2 M aqueous potassium carbonate solution (0.517 mL, 1.04 mmol) and stirred at 65 ° C. for 12 hours. After cooling to room temperature, water (40 mL) was added, and the precipitated solid was separated by filtration. The resulting solid is washed with water (30 mL), methanol (30 mL) and hexane (30 mL) to give the desired 2- {4 '-[4- (3,5-dimethylphenyl) -6-phenylpyridine-2 A white powder (yield 85.8 mg, 39%) of -yl] biphenyl-3-yl} -4,6-diphenyl-1,3,5-triazine (compound A-1118) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 2.50 (s, 6 H), 7. 18-8.0 1 (m, 18 H), 8. 29 (d, J = 7.8 Hz, 2 H), 8.43 (d, J = 8.1 Hz, 2 H), 8.83-8.87 (m, 5 H), 9.13 (s, 1 H).
Example 16

Under a nitrogen stream, 2- [3-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5- Triazine (150 mg, 0.345 mmol), 2- (2-benzofuryl) -6- (4-bromophenyl) -4-phenylpyridine (147 mg, 0.345 mmol), and tetrakis (triphenylphosphine) palladium (12.0 mg) , 0.0104 mmol) was suspended in tetrahydrofuran (6 mL). To this was added 2 M aqueous potassium carbonate solution (0.517 mL, 1.04 mmol) and stirred at 65 ° C. for 12 hours. After cooling to room temperature, water (40 mL) was added, and the precipitated solid was separated by filtration. The resulting solid is washed with water (30 mL), methanol (30 mL) and hexane (30 mL) to give the desired 2- {4 '-[6- (2-benzofuryl) -4-phenylpyridin-2-yl]. A white powder (yield 181 mg, 80%) of biphenyl-3-yl} -4,6-diphenyl-1,3,5-triazine (compound A-1045) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.23 to 7.41 (m, 2 H), 7.55 to 7.78 (m, 15 H), 7.98 to 8.04 (m, 5 H) ), 8.24-8.23 (m, 2H), 8.85-8.87 (m, 5H), 9.13 (brs, 1H).
Example 17

  Under a nitrogen stream, 2- [3-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5- Triazine (150 mg, 0.345 mmol), 4- (2-benzofuryl) -2- (4-bromophenyl) -6-phenylpyridine (147 mg, 0.345 mmol), and tetrakis (triphenylphosphine) palladium (12.0 mg) , 0.0104 mmol) was suspended in tetrahydrofuran (5 mL). To this was added 2 M aqueous potassium carbonate solution (0.517 mL, 1.04 mmol) and stirred at 65 ° C. for 4 hours. After cooling to room temperature, water (40 mL) was added, and the precipitated solid was separated by filtration. The resulting solid is washed with water (30 mL), methanol (30 mL) and hexane (30 mL) to give the desired 2- {4 '-[4- (2-benzofuryl) -6-phenylpyridin-2-yl]. A white powder (yield 180 mg, 80%) of biphenyl-3-yl} -4,6-diphenyl-1,3,5-triazine (compound A-685) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.35-7.77 (m, 15 H), 7.98 (brd, J = 7.8 Hz, 3 H), 8.20 (s, 1 H), 8.26 (s, 1 H), 8.32 (d, J = 7.2 Hz, 2 H), 8.46 (d, J = 8.4 Hz, 2 H), 8.85-8.87 (m, 5 H) ), 9.14 (s, 1 H).
Next, element evaluation will be described.

  Structural formulas of compounds used for element evaluation and their abbreviations are shown below.

Element Example 1
As a substrate, a glass substrate with an ITO transparent electrode in which an indium-tin oxide (ITO) film (film thickness 110 nm) having a width of 2 mm was patterned in a stripe shape was used. The substrate was washed with isopropyl alcohol and then subjected to surface treatment by ozone ultraviolet ray washing. Each layer was vacuum-deposited on the cleaned substrate by a vacuum deposition method to produce an organic electroluminescent device having a light-emitting area of 4 mm ² as shown in FIG. Each organic material was deposited by resistance heating.

First, the glass substrate was introduced into a vacuum deposition tank, and the pressure was reduced to 1.0 × 10 ⁻⁴ Pa.

  Thereafter, a hole injection layer 2, a charge generation layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode layer as an organic compound layer on a glass substrate with an ITO transparent electrode shown in FIG. All 7 were formed into a film by vacuum evaporation, laminating | stacking this in order.

  As the hole injection layer 2, 65 nm of sublimation purified HIL was deposited at a rate of 0.15 nm / sec.

  As the charge generation layer 3, 5 nm of sublimation purified HAT was deposited at a rate of 0.05 nm / sec.

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

  As the light emitting layer 5, EML-1 and EML-2 were deposited to a thickness of 25 nm at a ratio of 95: 5 (deposition rate 0.18 nm / sec).

  As the electron transport layer 6, 2- {4 '-[2- (2-naphthyl) -6-phenylpyridin-4-yl] biphenyl-3-yl} -4,6-diphenyl synthesized in Example 1 A 30 nm film was formed at a ratio of 50:50 (weight ratio) of 1,3,5-triazine (compound A-2) and Liq (film forming speed: 0.15 nm / sec).

Finally, a metal mask was disposed to be orthogonal to the ITO stripes, and the cathode layer 7 was formed. The cathode layer 7 is formed by depositing silver / magnesium (1/10 weight ratio) and silver in this order at 80 nm (deposition rate 0.5 nm / sec) and 20 nm (deposition rate 0.2 nm / sec) And a two-layer structure.

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

  Furthermore, this element was sealed in a nitrogen atmosphere glove box with an oxygen and water concentration of 1 ppm or less. Sealing used the sealing cap made from glass, and the said film-forming board | substrate epoxy-type ultraviolet-ray cured resin (made by Nagase ChemteX Corp.).

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

Element Example 2
In the element example 1, 2- {4 '-[4- (2-naphthyl) -6-phenylpyridin-2-yl] biphenyl-3-yl} synthesized in Example 2 instead of compound A-2 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example 1 except that −4,6-diphenyl-1,3,5-triazine (compound A-362) was used. The results are shown in Table 1. In addition, about element lifetime, after measuring element lifetime (h), it represented by the relative value which made element lifetime of element reference example 1 100.

Device Example 3
In the element example 1, 2- {4 '-[6- (2-naphthyl) -4-phenylpyridin-2-yl] biphenyl-3-yl} synthesized in Example-3 instead of compound A-2 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example 1 except that −4,6-diphenyl-1,3,5-triazine (compound A-722) was used. The results are shown in Table 1. In addition, about element lifetime, after measuring element lifetime (h), it represented by the relative value which made element lifetime of element reference example 1 100.

Device Example 4
In the element example 1, 2- {4 '-[2- (1-naphthyl) -6-phenylpyridin-4-yl] biphenyl-3-yl} synthesized in Example 6 instead of compound A-2 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example 1 except that −4,6-diphenyl-1,3,5-triazine (compound A-4) was used. The results are shown in Table 1. In addition, about element lifetime, after measuring element lifetime (h), it represented by the relative value which made element lifetime of element reference example 1 100.

Element Example 5
In the element example 1, 2- {4 '-[4- (1-naphthyl) -6-phenylpyridin-2-yl] biphenyl-3-yl} synthesized in Example 7 instead of compound A-2 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example 1 except that −4,6-diphenyl-1,3,5-triazine (compound A-364) was used. The results are shown in Table 1. In addition, about element lifetime, after measuring element lifetime (h), it represented by the relative value which made element lifetime of element reference example 1 100.

Element Example 6
In the element example 1, 2- {4 '-[4- (1-naphthyl) -6- (2-naphthyl) pyridin-2-yl] biphenyl-synthesized in Example-8 instead of compound A-2 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example 1 except that 3-yl} -4,6-diphenyl-1,3,5-triazine (Compound A-365) was used. The results are shown in Table 1. In addition, about element lifetime, after measuring element lifetime (h), it represented by the relative value which made element lifetime of element reference example 1 100.

Element Example 7
4,6-Diphenyl-2- [4 '-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl synthesized in Example 9 instead of compound A-2 in Element Example 1 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example 1 except that -1,3,5-triazine (compound A-721) was used. The results are shown in Table 1. In addition, about element lifetime, after measuring element lifetime (h), it represented by the relative value which made element lifetime of element reference example 1 100.

Element Reference Example 1
In the element example 1, 2- [5- (9-phenanthryl) -4 ′-(2-pyrimidyl) biphenyl-3-yl] -4 described in JP-A-2011-063584 instead of the compound A-2 The organic electroluminescent element was produced and evaluated by the same method as element example 1 except having used 6, 6- diphenyl 1, 3, 5- triazine (ETL-2). The results are shown in Table 1. In addition, about element lifetime, after measuring element lifetime (h), the element lifetime of this element reference example 1 was made into the reference value (100).

  The triazine compounds (11) and (1) of the present invention are excellent in heat resistance of film quality, and therefore, by using the compound, an organic electroluminescent device excellent in long life and luminous efficiency can be provided.

  The triazine compounds (11) and (1) of the present invention are used as an electron transport material for an organic electroluminescent device excellent in low driving voltage. Furthermore, according to the present invention, an organic electroluminescent device excellent in power consumption can be provided.

  In addition, the triazine compound of the present invention has excellent thermal stability at the time of sublimation purification, and is excellent in operability of sublimation purification, and can provide a material with few impurities causing the deterioration of the organic electroluminescent device. Moreover, since the triazine compound of this invention is excellent in stability of a vapor deposition film, it can provide a long-lived organic electroluminescent element.

In addition, the thin film comprising the triazine compound (11) or (1) of the present invention is excellent in electron transport ability, hole blocking ability, redox resistance, water resistance, oxygen resistance, electron injection characteristics, etc. And useful as an electron transporting material, a hole blocking material, a light emitting host material, and the like. In particular, it is useful when used with an electron transport material. Further, since the triazine compounds (11) and (1) of the present invention are wide band gap compounds, they can be suitably used not only for conventional fluorescent device applications but also for phosphorescent devices.

1. Glass substrate with ITO transparent electrode Hole injection layer 3. Charge generation layer 4. Hole transport layer 5. Light emitting layer 6. Electron transport layer 7. Cathode layer

Claims (20)

The triazine compound shown by General formula (11).
(In the general formula (11),
Ar ¹ each independently represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group).
Ar ² and Ar ³ each independently represent an aromatic hydrocarbon group which may be linked and / or fused with 6 to 24 carbon atoms, a 3 to 25 carbon linkage composed only of 6-membered rings, and And / or a nitrogen-containing heteroaromatic group which may be fused, or a linked and / or fused ring having 3 to 25 carbon atoms which is composed of an atom selected from the group consisting of H, C, O, and S A heteroaromatic group which may be substituted (these groups may be substituted with a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).
Each of R ⁵ , R ⁶ and R ⁷ independently represents an alkyl group having 1 to 4 carbon atoms. p represents 0, 1, 2, 3 or 4; When p is 2, 3 or 4, R ⁵ may be different from each other. q represents 0, 1, 2, 3 or 4; When q is 2, 3 or 4, R ⁶ may be different from each other. r represents 0 or 1;
Z ¹ and Z ² each independently represent a nitrogen atom or C—H. However, either ^one of Z ¹ or Z ² represents a nitrogen atom, and the other represents C—H. ) Each of Ar ² and Ar ³ independently represents an aromatic hydrocarbon group which may be linked and / or fused with 6 to 24 carbon atoms, a link having 3 to 25 carbon atoms composed of only a 6-membered ring, and And / or a nitrogen-containing heteroaromatic group which may be fused, or a linked and / or fused ring having 3 to 25 carbon atoms which is composed of an atom selected from the group consisting of H, C, O, and S The triazine compound according to claim 1, which is an optionally selected heteroaromatic group. Ar ² and Ar ³ each independently represent a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a fluoranthenylphenyl group, a pyridylphenyl group, a quinolylphenyl group, a thienylphenyl group, a furylphenyl group, Benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, naphthyl group, pyridyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl group, or dibenzofuryl group (these compounds The triazine compound according to claim 1, wherein the group is a fluorine atom or optionally substituted with a methyl group. Ar ² and Ar ³ each independently represent phenyl group, tolyl group, dimethylphenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl group, pyridylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, naphthyl group The triazine compound according to any one of claims 1 to 3, which is a pyridyl group, a benzothienyl group, a benzofuryl group, a phenanthryl group, an anthryl group, a dibenzothienyl group or a dibenzofuryl group. 5. The triazine compound according to claim ¹ , wherein Ar ¹ is each independently a phenyl group or a naphthyl group (these groups may be substituted with a methyl group or a phenyl group). . 6. The triazine compound according to claim ¹ , wherein each Ar ¹ is independently a phenyl group, a naphthyl group or a biphenyl group. The triazine compound according to claim 1, 2, 3, 4, 5, or 6, wherein Ar ¹ is a phenyl group. The triazine compound according to claim 1, 2, 3, 4, 5, 6, or 7, wherein p = q = r = 0. The triazine compound of Claim 1 shown by General formula (1).
(In the general formula (1),
Ar ¹ each independently represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group).
Ar ² is an aromatic hydrocarbon group which may be linked and / or fused, having 6 to 24 carbon atoms, and has a carbon number of 3 to 25 composed of only a 6-membered ring and / or fused Or a heteroaromatic group having 3 to 25 carbon atoms which may be linked and / or condensed, which is composed of an atom selected from the group consisting of H, C, O, and S. A group (these groups may be substituted with a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).
Ar ³ is a C 10-24 linked and / or fused aromatic hydrocarbon group, a C 3-25 linked and / or fused ring composed of only six-membered rings, Or a heteroaromatic group having 3 to 25 carbon atoms which may be linked and / or condensed, which is composed of an atom selected from the group consisting of H, C, O, and S. A group (these groups may be substituted with a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).
Z ¹ and Z ² each independently represent a nitrogen atom or C—H. However, either ^one of Z ¹ or Z ² represents a nitrogen atom, and the other represents C—H. ) Ar ² is an aromatic hydrocarbon group which may be linked and / or fused with 6 to 24 carbon atoms, or linked and / or fused with 3 to 25 carbon atoms composed of only a 6-membered ring Or a heteroaromatic group having 3 to 25 carbon atoms which may be linked and / or condensed, which is composed of an atom selected from the group consisting of H, C, O, and S. The triazine compound according to claim 9, which is a group. Ar ² represents a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a fluoranthenylphenyl group, a pyridylphenyl group, a quinolylphenyl group, a thienylphenyl group, a furylphenyl group, a benzothienylphenyl group, a benzofuryl Phenyl, dibenzothienylphenyl, dibenzofurylphenyl, naphthyl, benzothienyl, benzofuryl, phenanthryl, anthryl, dibenzothienyl or dibenzofuryl groups (these groups are a fluorine atom or a methyl group The triazine compound according to claim 9, which is optionally substituted. Ar ³ is an aromatic hydrocarbon group which may be linked and / or fused with 10 to 24 carbon atoms, or linked and / or fused with 3 to 25 carbon atoms composed of only a 6-membered ring Or a heteroaromatic group having 3 to 25 carbon atoms which may be linked and / or condensed, which is composed of an atom selected from the group consisting of H, C, O, and S. The triazine compound according to claim 9, which is a group. And Ar ³ represents a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a fluoranthenylphenyl group, a pyridylphenyl group, a quinolylphenyl group, a thienylphenyl group, a furylphenyl group, a benzothienylphenyl group, a benzofurylphenyl group, Dibenzothienylphenyl group, dibenzofurylphenyl group, naphthyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl group, or dibenzofuryl group (these groups are substituted by a fluorine atom or a methyl group The triazine compound according to claim 9, 10, or 11 . The compound represented by the general formula (12) and the compound represented by the general formula (13) are subjected to a coupling reaction either sequentially or simultaneously in the presence of a base or in the absence of a base in the presence of a palladium catalyst. The method for producing a triazine compound according to claim 1, characterized in that
(In the general formulas (11), (12) and (13),
Ar ¹ , Ar ² , Ar ³ , R ⁵ , R ⁶ , R ⁷ , p, q, r, Z ¹ and Z ² are as defined in claim 1.
Y represents a leaving group.
M represents ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ . However, R ¹ and R ² each independently represent a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, and R ⁴ represents a hydrogen atom or carbon It represents an alkyl group of the number 1 to 4 or a phenyl group, and two R ⁴ of B (OR ⁴ ) ₂ may be the same or different.
In addition, two R ⁴ can be combined to form a ring by containing an oxygen atom and a boron atom. ) The compound represented by the general formula (2) and the compound represented by the general formula (3) are subjected to a coupling reaction either sequentially or simultaneously in the presence of a base or in the absence of a base in the presence of a palladium catalyst The manufacturing method of the triazine compound of Claim 9 characterized by the above-mentioned.
(In the general formulas (1), (2) and (3),
Ar ¹ , Ar ² , Ar ³ , Z ¹ and Z ² are as defined in claim 9 .
Y represents a leaving group.
M represents ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ . However, R ¹ and R ² each independently represent a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, and R ⁴ represents a hydrogen atom or carbon It represents an alkyl group of the number 1 to 4 or a phenyl group, and two R ⁴ of B (OR ⁴ ) ₂ may be the same or different.
In addition, two R ⁴ can be combined to form a ring by containing an oxygen atom and a boron atom. ) The compound represented by the general formula (14) is coupled with the compound represented by the general formula (15) in the presence of a base or in the absence of a base in the presence of a palladium catalyst. The manufacturing method of the triazine compound of Claim 1 which is.
(In the general formulas (11), (14) and (15),
Ar ¹ , Ar ² , Ar ³ , R ⁵ , R ⁶ , R ⁷ , p, q, r, Z ¹ and Z ² are as defined in claim 1.
Y represents a leaving group.
M represents ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ . However, R ¹ and R ² each independently represent a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, and R ⁴ represents a hydrogen atom or carbon It represents an alkyl group of the number 1 to 4 or a phenyl group, and two R ⁴ of B (OR ⁴ ) ₂ may be the same or different.
In addition, two R ⁴ can be combined to form a ring by containing an oxygen atom and a boron atom. ) The compound represented by the general formula (4) is coupled with the compound represented by the general formula (5) in the presence of a base or in the absence of a base in the presence of a palladium catalyst. The manufacturing method of the triazine compound of Claim 9 which is.
(In the general formulas (1), (4) and (5),
Ar ¹ , Ar ² , Ar ³ , Z ¹ and Z ² are as defined in claim 9 .
Y represents a leaving group.
M represents ZnR ¹ , MgR ² , Sn (R ³ ) ₃ or B (OR ⁴ ) ₂ . However, R ¹ and R ² each independently represent a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, and R ⁴ represents a hydrogen atom or carbon It represents an alkyl group of the number 1 to 4 or a phenyl group, and two R ⁴ of B (OR ⁴ ) ₂ may be the same or different.
In addition, two R ⁴ can be combined to form a ring by containing an oxygen atom and a boron atom. ) The material for organic electroluminescent elements containing the triazine compound of Claim 1. The electron transport material for organic electroluminescent elements containing the triazine compound of Claim 1. The material for organic electroluminescent elements containing the triazine compound of Claim 9.