JP6965083B2 - Compounds and luminescent compounds - Google Patents

Description

The present invention relates to novel compounds and luminescent compounds.

Luminescent compounds having a photoluminescence (PL) phenomenon or an electroluminescence (EL) phenomenon are known. Luminescence refers to a luminescence phenomenon in which a substance receives energy and excites it by irradiation of electromagnetic waves, application of an electric field, collision of electrons, etc., and emits a part or all of the energy as electromagnetic radiation and its light. Photoluminescence refers to luminescence generated by the stimulation of ultraviolet rays, visible light, and infrared rays. Electroluminescence refers to luminescence generated by applying an electric field.

The luminescent compound can be roughly divided into an organic luminescent compound having a hydrocarbon structure and an inorganic luminescent compound having no hydrocarbon structure and consisting only of an inorganic element.
Organic luminescent compounds are used in various applications such as fluorescent dyes, organic electroluminescent devices, and fluorescent probes by utilizing their luminescent functions.
An example of the organic luminescent compound used for these is shown below.

As described above, various structures are known for luminescent compounds, but in general, there are many relatively complicated structures such as having many aromatic groups or being a metal complex.
For example, studies on the synthesis and fluorescence properties of pyrimidine monoboron complexes or pyrimidine diboron complexes have been reported (eg, Non-Patent Documents 1 and 2).

In addition, studies on the fluorescence characteristics of compounds having a pyrimidine as a core and an extension of the π-system have been reported (see, for example, Non-Patent Document 3).

As described above, since luminescent compounds generally have many relatively complicated structures, their synthesis tends to be complicated.

Dalton Trans 2015, 44, 3326-3341 J. Org. Chem. 2013, 78, 7058-7067 J. Am. Chem. Soc. 2004, 126, 15396-15397

An object of the present invention is to solve the above-mentioned problems in the past and to achieve the following object. That is, an object of the present invention is to provide a compound which is relatively easy to synthesize but has luminescent properties.

ただし、前記一般式（１）中、Ｒ^１は、水素原子、及び置換基のいずれかを表す。Ｒ^２、及びＲ^３は、それぞれ独立して、水素原子、及び置換基のいずれかを表す。Ｒ^４は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^１は、置換基を有していてもよい芳香族基を表す。Ｒ^５は、水素原子、及び下記一般式（２）で表される基のいずれかを表す。

ただし、前記一般式（２）中、Ｒ^６は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^２は、置換基を有していてもよい芳香族基を表す。 The means for solving the above-mentioned problems are as follows. That is,
The compound of the present invention is characterized by being represented by the following general formula (1).

However, in the general formula (1), R ¹ represents either a hydrogen atom or a substituent. R ² and R ³ independently represent either a hydrogen atom or a substituent. R ⁴ represents a direct bond, a vinylene group, 1,3-butadienylene group, and an ethynylene group, and 1,3-butadiynylene groups. Ar ¹ represents an aromatic group which may have a substituent. R ⁵ represents either a hydrogen atom or a group represented by the following general formula (2).

However, in the general formula (2), R ⁶ represents any of a direct bond, a vinylene group, a 1,3-butadienylene group, an ethynylene group, and a 1,3-butadienylene group. Ar ² represents an aromatic group which may have a substituent.

ただし、前記一般式（１）中、Ｒ^１は、水素原子、及び置換基のいずれかを表す。Ｒ^２、及びＲ^３は、それぞれ独立して、水素原子、及び置換基のいずれかを表す。Ｒ^４は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^１は、置換基を有していてもよい芳香族基を表す。Ｒ^５は、水素原子、及び下記一般式（２）で表される基のいずれかを表す。

ただし、前記一般式（２）中、Ｒ^６は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^２は、置換基を有していてもよい芳香族基を表す。 The luminescent compound of the present invention is characterized by being represented by the following general formula (1).

However, in the general formula (1), R ¹ represents either a hydrogen atom or a substituent. R ² and R ³ independently represent either a hydrogen atom or a substituent. R ⁴ represents a direct bond, a vinylene group, 1,3-butadienylene group, and an ethynylene group, and 1,3-butadiynylene groups. Ar ¹ represents an aromatic group which may have a substituent. R ⁵ represents either a hydrogen atom or a group represented by the following general formula (2).

However, in the general formula (2), R ⁶ represents any of a direct bond, a vinylene group, a 1,3-butadienylene group, an ethynylene group, and a 1,3-butadienylene group. Ar ² represents an aromatic group which may have a substituent.

According to the present invention, it is possible to provide a compound which can solve the above-mentioned problems in the past, achieve the above-mentioned object, and have luminescence while being relatively easy to synthesize.

ただし、前記一般式（１）中、Ｒ^１は、水素原子、及び置換基のいずれかを表す。Ｒ^２、及びＲ^３は、それぞれ独立して、水素原子、及び置換基のいずれかを表す。Ｒ^４は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^１は、置換基を有していてもよい芳香族基を表す。Ｒ^５は、水素原子、及び下記一般式（２）で表される基のいずれかを表す。

ただし、前記一般式（２）中、Ｒ^６は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^２は、置換基を有していてもよい芳香族基を表す。 (Compounds and luminescent compounds)
The compound of the present invention is represented by the following general formula (1).
The luminescent compound of the present invention is represented by the following general formula (1).

However, in the general formula (1), R ¹ represents either a hydrogen atom or a substituent. R ² and R ³ independently represent either a hydrogen atom or a substituent. R ⁴ represents a direct bond, a vinylene group, 1,3-butadienylene group, and an ethynylene group, and 1,3-butadiynylene groups. Ar ¹ represents an aromatic group which may have a substituent. R ⁵ represents either a hydrogen atom or a group represented by the following general formula (2).

However, in the general formula (2), R ⁶ represents any of a direct bond, a vinylene group, a 1,3-butadienylene group, an ethynylene group, and a 1,3-butadienylene group. Ar ² represents an aromatic group which may have a substituent.

The present inventors have made diligent studies to provide a compound which is relatively easy to synthesize but has luminescent properties. Then, the compound represented by the general formula (1), that is, having a pyrimidine ring, and an aromatic group bonded to the 4-position of the pyrimidine ring so as to be conjugated to the pyrimidine ring, 5 of the pyrimidine ring. It has been found that a compound in which a nitrogen atom is bonded to the position and a hydrogen atom is bonded to the 6-position of the pyrimidine ring, or an aromatic group is bonded to the pyrimidine ring so as to be conjugated, emits fluorescence. ..
The present inventors consider that the improvement in the electron density of the pyrimidine ring by introducing a nitrogen atom at the 5-position position of the pyrimidine ring effectively affects the expression of the fluorescence characteristics. .. Further, both an electron-withdrawing group and an electron-donating group can be introduced into the 4- and 6-positions of the pyrimidine ring, but an electron-withdrawing group (for example, an aromatic ring group having an electron-withdrawing property) is introduced. By introducing it, it is considered that the fluorescence characteristics will be further improved.

<R ¹ >
R ¹ represents either a hydrogen atom or a substituent.

The molecular weight of the substituent in R ¹ is not particularly limited and may be appropriately selected depending on the intended purpose, but 10 to 500 is preferable, 10 to 300 is more preferable, and 10 to 200 is particularly preferable.

<< Substituents >>
Examples of the substituent in R ¹ include a hydroxy group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, an alkyl group and an alkenyl group. , Alkinyl group, amino group, alkoxy group, aryl group, aryloxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acyloxy group, alkoxycarbonylamino group, aryloxycarbonylamino group, alkylsulfonyl group, Examples thereof include a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, an alkylsilyl group and an alkylsilyloxy group. As for the hydrocarbon group in these substituents, the hydrogen atom may be further substituted with a hydroxyl group, a halogen atom or the like.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
As the alkyl group, an alkyl group having 1 to 30 carbon atoms is preferable, an alkyl group having 1 to 20 carbon atoms is more preferable, and an alkyl group having 1 to 10 carbon atoms is particularly preferable. More specifically, the alkyl group includes, for example, a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, an n-octyl group, an n-decyl group, an n-hexadecyl group, a cyclopropyl group and a cyclopentyl group. Groups, cyclohexyl groups and the like can be mentioned.
As the alkenyl group, an alkenyl group having 2 to 30 carbon atoms is preferable, an alkenyl group having 2 to 20 carbon atoms is more preferable, and an alkenyl group having 2 to 10 carbon atoms is particularly preferable. More specific examples of the alkenyl group include a vinyl group, an allyl group, a 2-butenyl group, a 3-pentenyl group and the like.
As the alkynyl group, an alkynyl group having 2 to 30 carbon atoms is preferable, an alkynyl group having 2 to 20 carbon atoms is more preferable, and an alkynyl group having 2 to 10 carbon atoms is particularly preferable. More specific examples of the alkynyl group include a propargyl group and a 3-pentynyl group.
The amino group [-NRaRb: Ra and Rb independently represent either a hydrogen atom or a hydrocarbon group. ), An amino group having 0 to 30 carbon atoms is preferable, an amino group having 0 to 20 carbon atoms is more preferable, and an amino group having 0 to 10 carbon atoms is particularly preferable. More specific examples of the amino group include an amino group (-NH ₂ ), a methylamino group, a dimethylamino group, a diethylamino group and the like.
As the alkoxy group, an alkoxy group having 1 to 30 carbon atoms is preferable, an alkoxy group having 1 to 20 carbon atoms is more preferable, and an alkoxy group having 1 to 10 carbon atoms is particularly preferable. More specific examples of the alkoxy group include a methoxy group, an ethoxy group, a butoxy group, a 2-ethylhexyloxy group and the like.
As the aryloxy group, an aryloxy group having 6 to 30 carbon atoms is preferable, an aryloxy group having 6 to 20 carbon atoms is more preferable, and an aryloxy group having 6 to 12 carbon atoms is particularly preferable. More specific examples of the aryloxy group include a phenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group and the like.
As the acyl group, an acyl group having 1 to 30 carbon atoms is preferable, an acyl group having 1 to 20 carbon atoms is more preferable, and an acyl group having 1 to 12 carbon atoms is particularly preferable. More specific examples of the acyl group include an acetyl group, a benzoyl group, a formyl group, a pivaloyl group and the like.
As the alkoxycarbonyl group, an alkoxycarbonyl group having 2 to 30 carbon atoms is preferable, an alkoxycarbonyl group having 2 to 20 carbon atoms is more preferable, and an alkoxycarbonyl group having 2 to 12 carbon atoms is particularly preferable. More specific examples of the alkoxycarbonyl group include a methoxycarbonyl group and an ethoxycarbonyl group.
As the aryloxycarbonyl group, an aryloxycarbonyl group having 7 to 30 carbon atoms is preferable, an aryloxycarbonyl group having 7 to 20 carbon atoms is more preferable, and an aryloxycarbonyl group having 7 to 12 carbon atoms is particularly preferable. More specifically, the aryloxycarbonyl group includes, for example, a phenyloxycarbonyl group.
As the acyloxy group, an acyloxy group having 2 to 30 carbon atoms is preferable, an acyloxy group having 2 to 20 carbon atoms is more preferable, and an acyloxy group having 2 to 10 carbon atoms is particularly preferable. More specific examples of the acyloxy group include an acetoxy group and a benzoyloxy group.
As the acylamino group, an acylamino group having 2 to 30 carbon atoms is preferable, an acylamino group having 2 to 20 carbon atoms is more preferable, and an acylamino group having 2 to 10 carbon atoms is particularly preferable. More specifically, the acylamino group includes, for example, an acetylamino group.
As the alkoxycarbonylamino group, an alkoxycarbonylamino group having 2 to 30 carbon atoms is preferable, an alkoxycarbonylamino group having 2 to 20 carbon atoms is more preferable, and an alkoxycarbonylamino group having 2 to 12 carbon atoms is particularly preferable. More specific examples of the alkoxycarbonylamino group include a methoxycarbonylamino group.
As the aryloxycarbonylamino group, an aryloxycarbonylamino group having 7 to 30 carbon atoms is preferable, an aryloxycarbonylamino group having 7 to 20 carbon atoms is more preferable, and an aryloxycarbonylamino group having 7 to 12 carbon atoms is preferable. Especially preferable. More specifically, the aryloxycarbonylamino group includes, for example, a phenyloxycarbonylamino group.
As the alkylsulfonyl group, an alkylsulfonyl group having 1 to 30 carbon atoms is preferable, an alkylsulfonyl group having 1 to 20 carbon atoms is more preferable, and an alkylsulfonyl group having 1 to 12 carbon atoms is particularly preferable. More specifically, the alkylsulfonyl group includes, for example, a methanesulfonyl group (methylsulfonyl group), an ethanesulfonyl group (ethylsulfonyl group), an n-propanesulfonyl group (n-propylsulfonyl group), an isopropylsulfonyl group, and the like. Examples thereof include an n-butylsulfonyl group, an isobutylsulfonyl group, an n-pentylsulfonyl group, and an n-hexylsulfonyl group.
As the sulfonylamino group, a sulfonylamino group having 1 to 30 carbon atoms is preferable, a sulfonylamino group having 1 to 20 carbon atoms is more preferable, and a sulfonylamino group having 1 to 12 carbon atoms is particularly preferable. More specific examples of the sulfonylamino group include a methanesulfonylamino group and a benzenesulfonylamino group.
The sulfamoyl group [-SO ₂ NRaRb: Ra and Rb each independently represent either a hydrogen atom or a hydrocarbon group. ], A sulfamoyl group having 0 to 30 carbon atoms is preferable, a sulfamoyl group having 0 to 20 carbon atoms is more preferable, and a sulfamoyl group having 0 to 12 carbon atoms is particularly preferable. More specific examples of the sulfamoyl group include a sulfamoyl group (-SO ₂ NH ₂ ), a methyl sulfamoyl group, a dimethyl sulfamoyl group, a phenyl sulfamoyl group and the like.
The carbamoyl group [-CONRaRb: Ra and Rb each independently represent either a hydrogen atom or a hydrocarbon group. ], A carbamoyl group having 1 to 30 carbon atoms is preferable, a carbamoyl group having 1 to 20 carbon atoms is more preferable, and a carbamoyl group having 1 to 12 carbon atoms is particularly preferable. More specific examples of the carbamoyl group include a carbamoyl group (-CONH ₂ ), a methylcarbamoyl group, a diethylcarbamoyl group, a phenylcarbamoyl group and the like.
As the alkylthio group, an alkylthio group having 1 to 30 carbon atoms is preferable, an alkylthio group having 1 to 20 carbon atoms is more preferable, and an alkylthio group having 1 to 12 carbon atoms is particularly preferable. More specific examples of the alkylthio group include a methylthio group and an ethylthio group.
As the arylthio group, an arylthio group having 6 to 30 carbon atoms is preferable, an arylthio group having 6 to 20 carbon atoms is more preferable, and an arylthio group having 6 to 12 carbon atoms is particularly preferable. More specific examples of the arylthio group include a phenylthio group and the like.
As the alkylsilyl group, an alkylsilyl group having 3 to 40 carbon atoms is preferable, an alkylsilyl group having 3 to 30 carbon atoms is more preferable, and an alkylsilyl group having 3 to 24 carbon atoms is particularly preferable. More specific examples of the alkylsilyl group include a trimethylsilyl group and a triphenylsilyl group.
As the alkylsilyloxy group, an alkylsilyloxy group having 3 to 40 carbon atoms is preferable, an alkylsilyloxy group having 3 to 30 carbon atoms is more preferable, and an alkylsilyloxy group having 3 to 24 carbon atoms is particularly preferable. More specific examples of the alkylsilyloxy group include a trimethylsilyloxy group and a triphenylsilyloxy group.

ただし、前記一般式（３）中、Ｒ^１１、及びＲ^１２は、それぞれ独立して、水素原子、及び置換基のいずれかを表す。 R ¹ has a hydrogen atom, an aryl group which may have a substituent, an alkoxy group which may have a substituent, an alkylthio group which may have a substituent, and a substituent. It is preferably either an alkylsulfonyl group which may be used, or a group represented by the following general formula (3).

However, in the general formula (3), R ¹¹ and R ¹² independently represent either a hydrogen atom or a substituent.

An aryl group which may have the substituent, an alkoxy group which may have the substituent, an alkylthio group which may have the substituent, and an alkyl which may have the substituent. The sulfonyl group and the substituent in the group represented by the general formula (3) are not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include a hydroxyl group and a halogen atom.

-R ^{11, R 12} -
Examples of the substituent in R ¹¹ and R ¹² include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an acyl group and the like. In these substituents, the hydrogen atom may be further substituted with a hydroxyl group, a halogen atom, or the like.
As the alkyl group, an alkyl group having 1 to 30 carbon atoms is preferable, an alkyl group having 1 to 20 carbon atoms is more preferable, and an alkyl group having 1 to 10 carbon atoms is particularly preferable. More specifically, the alkyl group includes, for example, a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, an n-octyl group, an n-decyl group, an n-hexadecyl group, a cyclopropyl group and a cyclopentyl group. Groups, cyclohexyl groups and the like can be mentioned.
As the alkenyl group, an alkenyl group having 2 to 30 carbon atoms is preferable, an alkenyl group having 2 to 20 carbon atoms is more preferable, and an alkenyl group having 2 to 10 carbon atoms is particularly preferable. More specific examples of the alkenyl group include a vinyl group, an allyl group, a 2-butenyl group, a 3-pentenyl group and the like.
As the alkynyl group, an alkynyl group having 2 to 30 carbon atoms is preferable, an alkynyl group having 2 to 20 carbon atoms is more preferable, and an alkynyl group having 2 to 10 carbon atoms is particularly preferable. More specific examples of the alkynyl group include a propargyl group and a 3-pentynyl group.
As the aryl group, an aryl group having 4 to 30 carbon atoms is preferable, an aryl group having 4 to 20 carbon atoms is more preferable, and an aryl group having 6 to 12 carbon atoms is particularly preferable. The aryl group may have a hetero atom. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like. More specifically, the aryl group includes, for example, a phenyl group, a p-methylphenyl group, a naphthyl group, an anthranyl group, an imidazolyl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a piperidyl group and a morpholino group. Examples thereof include a benzoxazolyl group, a benzimidazolyl group, a benzthiazolyl group, a carbazolyl group and an azepinyl group.
As the acyl group, an acyl group having 1 to 30 carbon atoms is preferable, an acyl group having 1 to 20 carbon atoms is more preferable, and an acyl group having 1 to 12 carbon atoms is particularly preferable. More specific examples of the acyl group include an acetyl group, a benzoyl group, a formyl group, a pivaloyl group and the like.

The molecular weight of the substituent in R ¹¹ and R ¹² is not particularly limited and may be appropriately selected depending on the intended purpose, but 10 to 500 is preferable, 10 to 300 is more preferable, and 10 to 200 is particularly preferable. preferable.

<R ² , R ³ >
R ² and R ³ independently represent either a hydrogen atom or a substituent.
Examples of the substituent in R ² and R ³ include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an acyl group and the like. In these substituents, the hydrogen atom may be further substituted with a hydroxyl group, a halogen atom, or the like.
Preferred examples and specific examples of the alkyl group are the same as those of the preferred examples and specific examples of the alkyl group in the description of the substituents of ^{R 11} and R ^12.
Preferred examples and specific examples of the alkenyl group are the same as those of the preferred examples and specific examples of the alkenyl group in the description of the substituents of ^{R 11} and R ^12.
Preferred examples and specific examples of the alkynyl group are the same as those of the preferred examples and specific examples of the alkynyl group in the description of the substituents of ^{R 11} and R ^12.
Preferred examples and specific examples of the aryl group are the same as those of the preferred examples and specific examples of the aryl group in the description of the substituents of ^{R 11} and R ^12.
Preferred examples and specific examples of the acyl group are the same as those of the preferred examples and specific examples of the acyl group in the description of the substituents of ^{R 11} and R ^12.

As R ² and R ³ , a hydrogen atom and an alkyl group are preferable.

The molecular weight of the substituent in R ^2, and ^{R 2,} is not particularly limited and may be appropriately selected depending on the intended purpose, but is preferably 10 to 500, more preferably from 10 to 300, especially 10 to 200 preferable.

また、前記１，３−ブタジエニレン基は、以下の構造式で表される。

また、前記エチニレン基は、以下の構造式で表される。

また、前記１，３−ブタジイニレン基は、以下の構造式で表される。

<R ⁴ >
R ⁴ represents a direct bond, a vinylene group, 1,3-butadienylene group, and an ethynylene group, and 1,3-butadiynylene groups. Since R ⁴ is any of a direct bond, a vinylene group, a 1,3-butadienylene group, an ethynylene group, and a 1,3-butadienylene group, the pyrimidine ring and the aromatic of ^{Ar 1 in the above general formula (1) are used.} The rings can form one conjugated system.
The vinylene group is represented by the following structural formula.

The 1,3-butadienylene group is represented by the following structural formula.

The ethynylene group is represented by the following structural formula.

The 1,3-butadinirene group is represented by the following structural formula.

<Ar ¹ >
Ar ¹ represents an aromatic group which may have a substituent.
The molecular weight of Ar ¹ is not particularly limited and may be appropriately selected depending on the intended purpose, but is preferably 60 to 1,000, more preferably 60 to 500, and particularly preferably 60 to 300.
The number of the substituents is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include 1 to 5.

As the aromatic group, for example, an aromatic group having 4 to 30 carbon atoms is preferable, and an aromatic group having 4 to 20 carbon atoms is more preferable. The aromatic group may have a heteroatom. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
Specific examples of the aromatic group include a phenyl group, a naphthyl group, an anthranyl group, a biphenyl group, a terphenyl group, a frill group, a thienyl group, a benzofuryl group, a benzothienyl group, an imidazolyl group, a pyrazolyl group and a thiazolyl group. Group, isothiazolyl group, oxazolyl group, isooxazolyl group, pyridyl group, phenyl-pyridyl group, pyridyl-phenyl group, pyrimidyl group, pyrazil group, 1,3,5-triazyl group, benzoimidazolyl group, indazolyl group, benzothiazolyl group, benzoisoti Azolyl group, 2,1,3-benzothiazolyl group, benzoxazolyl group, benzoisooxazolyl group, 2,1,3-benzoxaziazolyl group, quinolyl group, isoquinolyl group, quinoxalyl group, Examples thereof include a quinazolyl group and a pyrrolyl group.

Examples of the aromatic ring in the aromatic group include the following structural formulas.

Examples of the substituent that Ar ¹ may have include a hydroxy group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydradino group and an imino group. , Alkyl group, alkenyl group, alkynyl group, amino group, alkoxy group, aryloxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acyloxy group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonyl Examples thereof include an amino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, an alkylsilyl group and an alkylsilyloxy group. As for the hydrocarbon group in these substituents, the hydrogen atom may be further substituted with a hydroxyl group, a halogen atom or the like.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
As the alkyl group, an alkyl group having 1 to 30 carbon atoms is preferable, an alkyl group having 1 to 20 carbon atoms is more preferable, and an alkyl group having 1 to 10 carbon atoms is particularly preferable. More specifically, the alkyl group includes, for example, a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, an n-octyl group, an n-decyl group, an n-hexadecyl group, a cyclopropyl group and a cyclopentyl group. Groups, cyclohexyl groups and the like can be mentioned.
As the alkenyl group, an alkenyl group having 2 to 30 carbon atoms is preferable, an alkenyl group having 2 to 20 carbon atoms is more preferable, and an alkenyl group having 2 to 10 carbon atoms is particularly preferable. More specific examples of the alkenyl group include a vinyl group, an allyl group, a 2-butenyl group, a 3-pentenyl group and the like.
As the alkynyl group, an alkynyl group having 2 to 30 carbon atoms is preferable, an alkynyl group having 2 to 20 carbon atoms is more preferable, and an alkynyl group having 2 to 10 carbon atoms is particularly preferable. More specific examples of the alkynyl group include a propargyl group and a 3-pentynyl group.
The amino group [-NRaRb: Ra and Rb independently represent either a hydrogen atom or a hydrocarbon group. ), An amino group having 0 to 30 carbon atoms is preferable, an amino group having 0 to 20 carbon atoms is more preferable, and an amino group having 0 to 10 carbon atoms is particularly preferable. More specific examples of the amino group include an amino group (-NH ₂ ), a methylamino group, a dimethylamino group, a diethylamino group and the like.
As the alkoxy group, an alkoxy group having 1 to 30 carbon atoms is preferable, an alkoxy group having 1 to 20 carbon atoms is more preferable, and an alkoxy group having 1 to 10 carbon atoms is particularly preferable. More specific examples of the alkoxy group include a methoxy group, an ethoxy group, a butoxy group, a 2-ethylhexyloxy group and the like.
As the aryloxy group, an aryloxy group having 6 to 30 carbon atoms is preferable, an aryloxy group having 6 to 20 carbon atoms is more preferable, and an aryloxy group having 6 to 12 carbon atoms is particularly preferable. More specific examples of the aryloxy group include a phenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group and the like.
As the acyl group, an acyl group having 1 to 30 carbon atoms is preferable, an acyl group having 1 to 20 carbon atoms is more preferable, and an acyl group having 1 to 12 carbon atoms is particularly preferable. More specific examples of the acyl group include an acetyl group, a benzoyl group, a formyl group, a pivaloyl group and the like.
As the alkoxycarbonyl group, an alkoxycarbonyl group having 2 to 30 carbon atoms is preferable, an alkoxycarbonyl group having 2 to 20 carbon atoms is more preferable, and an alkoxycarbonyl group having 2 to 12 carbon atoms is particularly preferable. More specific examples of the alkoxycarbonyl group include a methoxycarbonyl group and an ethoxycarbonyl group.
As the aryloxycarbonyl group, an aryloxycarbonyl group having 7 to 30 carbon atoms is preferable, an aryloxycarbonyl group having 7 to 20 carbon atoms is more preferable, and an aryloxycarbonyl group having 7 to 12 carbon atoms is particularly preferable. More specifically, the aryloxycarbonyl group includes, for example, a phenyloxycarbonyl group.
As the acyloxy group, an acyloxy group having 2 to 30 carbon atoms is preferable, an acyloxy group having 2 to 20 carbon atoms is more preferable, and an acyloxy group having 2 to 10 carbon atoms is particularly preferable. More specific examples of the acyloxy group include an acetoxy group and a benzoyloxy group.
As the acylamino group, an acylamino group having 2 to 30 carbon atoms is preferable, an acylamino group having 2 to 20 carbon atoms is more preferable, and an acylamino group having 2 to 10 carbon atoms is particularly preferable. More specifically, the acylamino group includes, for example, an acetylamino group.
As the alkoxycarbonylamino group, an alkoxycarbonylamino group having 2 to 30 carbon atoms is preferable, an alkoxycarbonylamino group having 2 to 20 carbon atoms is more preferable, and an alkoxycarbonylamino group having 2 to 12 carbon atoms is particularly preferable. More specific examples of the alkoxycarbonylamino group include a methoxycarbonylamino group.
As the aryloxycarbonylamino group, an aryloxycarbonylamino group having 7 to 30 carbon atoms is preferable, an aryloxycarbonylamino group having 7 to 20 carbon atoms is more preferable, and an aryloxycarbonylamino group having 7 to 12 carbon atoms is preferable. Especially preferable. More specifically, the aryloxycarbonylamino group includes, for example, a phenyloxycarbonylamino group.
As the sulfonylamino group, a sulfonylamino group having 1 to 30 carbon atoms is preferable, a sulfonylamino group having 1 to 20 carbon atoms is more preferable, and a sulfonylamino group having 1 to 12 carbon atoms is particularly preferable. More specific examples of the sulfonylamino group include a methanesulfonylamino group and a benzenesulfonylamino group.
The sulfamoyl group [-SO ₂ NRaRb: Ra and Rb each independently represent either a hydrogen atom or a hydrocarbon group. ], A sulfamoyl group having 0 to 30 carbon atoms is preferable, a sulfamoyl group having 0 to 20 carbon atoms is more preferable, and a sulfamoyl group having 0 to 12 carbon atoms is particularly preferable. More specific examples of the sulfamoyl group include a sulfamoyl group (-SO ₂ NH ₂ ), a methyl sulfamoyl group, a dimethyl sulfamoyl group, a phenyl sulfamoyl group and the like.
The carbamoyl group [-CONRaRb: Ra and Rb each independently represent either a hydrogen atom or a hydrocarbon group. ], A carbamoyl group having 1 to 30 carbon atoms is preferable, a carbamoyl group having 1 to 20 carbon atoms is more preferable, and a carbamoyl group having 1 to 12 carbon atoms is particularly preferable. More specific examples of the carbamoyl group include a carbamoyl group (-CONH ₂ ), a methylcarbamoyl group, a diethylcarbamoyl group, a phenylcarbamoyl group and the like.
As the alkylthio group, an alkylthio group having 1 to 30 carbon atoms is preferable, an alkylthio group having 1 to 20 carbon atoms is more preferable, and an alkylthio group having 1 to 12 carbon atoms is particularly preferable. More specific examples of the alkylthio group include a methylthio group and an ethylthio group.
As the arylthio group, an arylthio group having 6 to 30 carbon atoms is preferable, an arylthio group having 6 to 20 carbon atoms is more preferable, and an arylthio group having 6 to 12 carbon atoms is particularly preferable. More specific examples of the arylthio group include a phenylthio group and the like.
As the alkylsilyl group, an alkylsilyl group having 3 to 40 carbon atoms is preferable, an alkylsilyl group having 3 to 30 carbon atoms is more preferable, and an alkylsilyl group having 3 to 24 carbon atoms is particularly preferable. More specific examples of the alkylsilyl group include a trimethylsilyl group and a triphenylsilyl group.
As the alkylsilyloxy group, an alkylsilyloxy group having 3 to 40 carbon atoms is preferable, an alkylsilyloxy group having 3 to 30 carbon atoms is more preferable, and an alkylsilyloxy group having 3 to 24 carbon atoms is particularly preferable. More specific examples of the alkylsilyloxy group include a trimethylsilyloxy group and a triphenylsilyloxy group.

ただし、前記一般式（２）中、Ｒ^６は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^２は、置換基を有していてもよい芳香族基を表す。Ｒ^６が、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかであることで、前記一般式（１）においてピリミジン環とＡｒ^２の芳香族環とが１つの共役系を形成することができる。 <R ⁵ >
R ⁵ represents either a hydrogen atom or a group represented by the following general formula (2).

However, in the general formula (2), R ⁶ represents any of a direct bond, a vinylene group, a 1,3-butadienylene group, an ethynylene group, and a 1,3-butadienylene group. Ar ² represents an aromatic group which may have a substituent. Since R ⁶ is any of a direct bond, a vinylene group, a 1,3-butadienylene group, an ethynylene group, and a 1,3-butadienylene group, the pyrimidine ring and the aromatic of ^{Ar 2 in the general formula (1) are described above.} The rings can form one conjugated system.

<< Ar ² >>
The Ar ² is not particularly limited as long as it is an aromatic group that may have a substituent, and can be appropriately selected depending on the intended purpose. For example, the substitution exemplified in the description of ^{Ar 1} An aromatic group which may have a group and the like can be mentioned.

ただし、前記一般式（１−１）中、Ｒ^１、Ｒ^２、及びＲ^３は、前記一般式（１）中のＲ^１、Ｒ^２、及びＲ^３とそれぞれ同じである。Ｘ^１は、ハロゲン原子である。Ｘ^２は、水素原子、及びハロゲン原子のいずれかである。
前記ハロゲン原子としては、例えば、塩素原子、臭素原子が挙げられる。 <Method for producing a compound represented by the general formula (1)>
The method for producing the compound represented by the general formula (1) is not particularly limited and may be appropriately selected depending on the intended purpose. However, the compound represented by the following general formula (1-1) and the following are used. A method of reacting with a compound represented by the general formula (1-2) is preferable.
The reaction is an example of a method for producing a compound represented by the general formula (1), and the compound of the present invention is not limited to the compound obtained by the production method.

In the general formula ^(1-1), R 1, ^{R 2,} and ^{R 3, R} 1, ^{R 2} in the formula (1), and ^{R 3} and are each the same. X ¹ is a halogen atom. X ² is either a hydrogen atom or a halogen atom.
Examples of the halogen atom include a chlorine atom and a bromine atom.

ただし、前記一般式（１−２）中、Ａｒ^１は、前記一般式（１）中のＡｒ^１と同じである。Ｘ^３は、−Ｂ（ＯＨ）_２、ビニル基、及びアセチニル基のいずれかを表す。

However, in the general formula (1-2), Ar ¹ is the same ^{as Ar 1} in the general formula (1). X ³ represents any of -B (OH) ₂ , a vinyl group, and an acetylynyl group.

In the compound represented by the general formula (1), when R ⁵ is a group represented by the general formula (2), in the reaction, X ² is a halogen atom. It is preferable to use 2 mol or more of the compound represented by the general formula (1-2) with respect to 1 mol of the compound represented by 1-1).

The reaction time in the reaction is not particularly limited and may be appropriately selected depending on the intended purpose, and examples thereof include 1 hour to 36 hours.
The reaction temperature in the reaction is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include 30 ° C. to 120 ° C.
The reaction may be carried out without a catalyst or in the presence of a catalyst, but it is preferably carried out in the presence of a catalyst. As the catalyst, for example, a metal-containing catalyst is preferable, a palladium catalyst is more preferable, and tetrakis (triphenylphosphine) palladium is particularly preferable.

The compound and the luminescent compound fluoresce, for example. Examples of the wavelength of fluorescence include 400 nm to 600 nm at the maximum wavelength.

The quantum yields of the compound and the luminescent compound are not particularly limited and may be appropriately selected depending on the intended purpose, but are preferably 5% or more, more preferably 15% or more, still more preferably 20% or more. It is preferable, and 50% or more is particularly preferable. The upper limit of the quantum yield is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include 75% and 80%.

<Use>
The use of the compound and the luminescent compound is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include fluorescent dyes, fluorescent paints, fluorescent plastics, fluorescent probes and organic electroluminescent elements. ..

Hereinafter, the present invention will be specifically described with reference to examples of the present invention, but the present invention is not limited to these examples.

(Example 1)
<Synthesis of 4,6-diphenylpyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (2.00 g, 11.2 mmol), phenylboronic acid (3.40 g, 27.9 mmol), sodium carbonate (5.92 g, 55.9 mmol). To a solution of tetrakis (triphenylphosphine) palladium (0) (1.29 g, 1.12 mmol) in toluene (112 mL), ethanol (28 mL) and distilled water (28 mL) were added at room temperature under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (50 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (50 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (50 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-diphenylpyrimidine-2,5-diamine (2.74 g, yield 94%). ..

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.81-7.74 (m, 4H), 7.55-7.42 (m, 6H), 4.87 (s, 2H), 3.50 (s) , 2H)

(Example 2)
<Synthesis of 4,6-di (naphthalene-1-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.79 mmol), 1-naphthylboronic acid (1.14 g, 6.63 mmol), sodium carbonate (1.48 g, 14.0 mmol). To a solution of tetrakis (triphenylphosphine) palladium (0) (328 mg, 0.283 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature and heated under an argon atmosphere. After stirring under reflux conditions for 20 hours, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-di (naphthalene-1-yl) pyrimidin-2,5-diamine (1. 0 g, yield 99%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
¹ H NMR (400 MHz, THF-d ₈ ) δ 7.98-7.87 (m, 6H), 7.64 (dd, J = 1.3, 7.1 Hz, 2H), 7.56 (dd, dd, 6H) J = 7.1, 8.2Hz, 2H), 7.53-7.42 (m, 4H), 5.37 (s, 2H), 3.20 (s, 2H)

(Example 3)
<Synthesis of 4,6-di (naphthalene-2-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.79 mmol), 2-naphthylboronic acid (1.18 g, 6.88 mmol), sodium carbonate (1.48 g, 14.0 mmol). To a solution of tetrakis (triphenylphosphine) palladium (0) (323 mg, 0.280 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature and heated under an argon atmosphere. After stirring under reflux conditions for 20 hours, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-di (naphthalene-2-yl) pyrimidin-2,5-diamine (0. 98 g, yield 97%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 8.32 (d, J = 1.6 Hz, 2H), 7.99 (d, J = 8.5 Hz, 2H), 7.97-7.84 (m, 6H), 7.61-7.51 (m, 4H), 4.91 (s, 2H), 3.65 (s, 2H)

(Example 4)
<Synthesis of 4,6-di ([1,1'-biphenyl] -4-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.79 mmol), 4-biphenylboronic acid (1.27 g, 6.43 mmol), sodium carbonate (1.48 g, 14.0 mmol). To a solution of tetrakis (triphenylphosphine) palladium (0) (162 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature and heated under an argon atmosphere. After stirring under reflux conditions for 20 hours, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) and 4,6-di ([1,1'-biphenyl] -4-yl) pyrimidin-2,5- Diamine was obtained (1.13 g, yield 98%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.93-7.86 (m, 4H), 7.79-7.70 (m, 4H), 7.69-7.62 (m, 4H), 7 .52-7.44 (m, 4H), 7.43-7.36 (m, 2H), 4.87 (s, 2H), 3.63 (s, 2H)

(Example 5)
<Synthesis of 4,6-di ([1,1': 3', 1''-terphenyl] -5'-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (358 mg, 2.00 mmol), 5'-m-terphenylboronic acid (1.22 g, 4.45 mmol), sodium carbonate (1.06 g, To a solution of 10.0 mmol) and tetrakis (triphenylphosphine) palladium (0) (116 mg, 0.100 mmol) in toluene (20 mL), ethanol (5 mL) and distilled water (5 mL) are added at room temperature to create an argon atmosphere. After stirring under heating and reflux conditions for 20 hours, the reaction solution was cooled to room temperature. Distilled water (5 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (10 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (10 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) and 4,6-di ([1,1': 3', 1 "-terphenyl] -5'". -Il) Pyrimidine-2,5-diamine was obtained (1.01 g, yield 90%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 8.01 (d, J = 1.8 Hz, 4H), 7.91 (t, J = 1.8 Hz, 2H), 7.75-7.67 (m, 8H), 7.53-7.45 (m, 8H), 7.44-7.37 (m, 4H), 4.99 (s, 2H), 3.71 (s, 2H)

(Example 6)
<Synthesis of 4,6-di ((E) -styryl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.79 mmol), trans-2-phenylvinylboronic acid (0.945 g, 6.42 mmol), sodium carbonate (1.48 g, 14). To a solution of 9.0 mmol) and tetrakis (triphenylphosphine) palladium (0) (322 mg, 0.279 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-di ((E) -styryl) pyrimidine-2,5-diamine (0. 72 g, yield 82%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.83 (d, J = 15.6 Hz, 2H), 7.64-7.57 (m, 4H), 7.43-7.36 (m, 4H) , 7.36-7.30 (m, 2H), 7.21 (d, J = 15.6Hz, 2H), 4.65 (s, 2H), 3.45 (s, 2H)

(Example 7)
<Synthesis of 4,6-bis (phenylethynyl) pyrimidine-2,5-diamine>

4,6-Dichloropyrimidine-2,5-diamine (500 mg, 2.79 mmol), phenylacetylene (0.740 mL, 6.70 mmol), copper iodide (26.6 mg, 0.279 mmol), and dichlorobis (triphenyl). A solution of phosphine) palladium (196 mg, 0.279 mmol) in diisopropylamine (2.8 mL) was placed in a reaction vessel, stirred at 80 ° C. for 20 hours under an argon atmosphere, and then the reaction solution was cooled to room temperature. Distilled water (5 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with chloroform (5 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (5 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-bis (phenylethynyl) pyrimidine-2,5-diamine (0.574 g, yield). Rate 63%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.65-7.57 (m, 4H), 7.47-7.34 (m, 6H), 4.77 (s, 2H), 4.25 (s) , 2H)

(Example 8)
<Synthesis of 4,6-bis (naphthalene-2-ylethynyl) pyrimidine-2,5-diamine>

4,6-Dichloropyrimidine-2,5-diamine (245 mg, 1.36 mmol), (2-naphthyl) acetylene (0.479 mL, 3.14 mmol), copper iodide (13.0 mg, 0.0683 mmol), and A solution of dichlorobis (triphenylphosphine) palladium (95.9 mg, 0.137 mmol) in diisopropylamine (1.4 mL) was placed in a reaction vessel, stirred at 80 ° C. for 20 hours under an argon atmosphere, and then the reaction solution was brought to room temperature. Cooled. Distilled water (3 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with chloroform (5 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (5 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-bis (naphthalene-2-ylethynyl) pyrimidin-2,5-diamine (0. 392 g, yield 70%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 8.17 (d, J = 1.5 Hz, 2H), 7.90-7.81 (m, 6H), 7.64 (dd, J = 1.5, 8.5Hz, 2H), 7.59-7.50 (m, 4H), 4.79 (s, 2H), 4.34 (s, 2H)

(Example 9)
<Synthesis of 4,6-di (furan-2-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.79 mmol), 2-furanylboronic acid (0.718 g, 6.42 mmol), sodium carbonate (1.49 g, 14.0 mmol), To a solution of tetrakis (triphenylphosphine) palladium (0) (161 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature, and the mixture was heated under reflux in an argon atmosphere. After stirring under the conditions for 20 hours, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to give 4,6-di (fran-2-yl) pyrimidin-2,5-diamine (0. 433 g, yield 64%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.63 (dd, J = 0.8, 1.8 Hz, 2H), 7.24 (dd, J = 0.8, 3.5 Hz, 2H), 6. 59 (dd, J = 1.8, 3.5Hz, 2H), 4.98 (s, 2H), 4.65 (s, 2H)

(Example 10)
<Synthesis of 4,6-di (fran-3-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (501 mg, 2.79 mmol), 3-furanylboronic acid (0.718 g, 6.42 mmol), sodium carbonate (1.48 g, 14.0 mmol), To a solution of tetrakis (triphenylphosphine) palladium (0) (161 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature, and the mixture was heated under reflux in an argon atmosphere. After stirring under the conditions for 20 hours, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to give 4,6-di (fran-3-yl) pyrimidine-2,5-diamine (0. 618 g, yield 91%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 8.06 (dd, J = 0.9, 1.5 Hz, 2H), 7.55 (dd, J = 1.5, 1.8 Hz, 2H), 6. 97 (dd, J = 0.9, 1.8Hz, 2H), 4.67 (s, 2H), 3.60 (s, 2H)

(Example 11)
<Synthesis of 4,6-di (thiophen-2-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (501 mg, 2.79 mmol), 2-thienylboronic acid (0.822 g, 6.42 mmol), sodium carbonate (1.42 g, 14.0 mmol). To a solution of tetrakis (triphenylphosphine) palladium (0) (162 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature and heated under an argon atmosphere. After stirring under reflux conditions for 20 hours, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to give 4,6-di (thiophen-2-yl) pyrimidin-2,5-diamine (0. 556 g, yield 72%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.79 (dd, J = 1.1, 3.7 Hz, 2H), 7.53 (dd, J = 1.1, 5.1 Hz, 2H), 7. 20 (dd, J = 3.7, 5.1 Hz, 2H), 4.78 (s, 2H), 3.99 (s, 2H)

(Example 12)
<Synthesis of 4,6-di (thiophene-3-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.79 mmol), 3-thienylboronic acid (0.821 g, 6.42 mmol), sodium carbonate (1.48 g, 14.0 mmol). To a solution of tetrakis (triphenylphosphine) palladium (0) (162 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature and heated under an argon atmosphere. After stirring under reflux conditions for 20 hours, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to give 4,6-di (thiophene-3-yl) pyrimidin-2,5-diamine (0. 737 g, yield 96%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (500 MHz, CDCl ₃ ) δ 7.92 (dd, J = 1.2, 3.0 Hz, 2H), 7.62 (dd, J = 1.2, 5.0 Hz, 2H), 7. 46 (dd, J = 3.0, 5.0Hz, 2H), 4.71 (s, 2H), 3.71 (s, 2H)

(Example 13)
<Synthesis of 4,6-di (benzofuran-2-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (501 mg, 2.79 mmol), benzofuran-2-boronic acid (1.05 g, 6.46 mmol), sodium carbonate (1.48 g, 14.0 mmol). ), And tetrakis (triphenylphosphine) palladium (0) (161 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature, and under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-di (benzofuran-2-yl) pyrimidin-2,5-diamine (0. 748 g, yield 78%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.70 (dd, J = 1.4, 8.2 Hz, 2H), 7.63 (d, J = 1.0 Hz, 2H), 7.60 (ddd, J = 0.9, 1.0, 8.3Hz, 2H), 7.40 (ddd, J = 1.4, 7.3, 8.3Hz, 2H), 7.32 (ddd, J = 0. 9, 7.3, 8.2Hz, 2H)

(Example 14)
<Synthesis of 4,6-di (benzofuran-3-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.79 mmol), benzofuran-3-boronic acid (1.04 g, 6.46 mmol), sodium carbonate (1.48 g, 14.0 mmol). ), And tetrakis (triphenylphosphine) palladium (0) (161 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature, and under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-di (benzofuran-3-yl) pyrimidin-2,5-diamine (0. 930 g, yield 97%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, DMSO-d ₆ ) δ 8.66 (s, 2H), 8.41 (dd, J = 1.5, 7.9 Hz, 2H), 7.68 (dd, J = 0. 9, 8.2Hz, 2H), 7.42 (ddd, J = 1.5, 7.2, 8.2Hz, 2H), 7.36 (ddd, J = 0.9, 7.2, 7. 9Hz, 2H), 6.11 (s, 2H), 4.34 (s, 2H)

(Example 15)
<Synthesis of 4,6-bis (benzo [b] thiophen-2-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.79 mmol), benzo [b] thiophen-2-boronic acid (1.26 g, 7.08 mmol), sodium carbonate (1.48 g). , 14.0 mmol), and tetrakis (triphenylphosphine) palladium (0) (162 mg, 0.140 mmol) in a toluene (28 mL) solution, ethanol (7 mL) and distilled water (7 mL) were added at room temperature, and argon was added. The reaction solution was cooled to room temperature after stirring for 20 hours under heating and reflux conditions in an atmosphere. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-bis (benzo [b] thiophen-2-yl) pyrimidin-2,5-diamine. (1.03 g, yield 98%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, DMSO-d ₆ ) δ 8.25 (d, J = 0.8 Hz, 2H), 8.06-7.92 (m, 4H), 7.49-7.39 (m, 4H), 6.13 (s, 2H), 4.90 (s, 2H)

(Example 16)
<Synthesis of 4,6-bis (benzo [b] thiophene-3-yl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.79 mmol), benzo [b] thiophen-3-boronic acid (1.14 g, 6.44 mmol), sodium carbonate (1.48 g). , 14.0 mmol), and tetrakis (triphenylphosphine) palladium (0) (161 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature, and argon was added. The reaction solution was cooled to room temperature after stirring for 20 hours under heating and reflux conditions in an atmosphere. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-bis (benzo [b] thiophene-3-yl) pyrimidin-2,5-diamine. (0.593 g, yield 57%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 8.11-8.03 (m, 2H), 7.98-7.90 (m, 4H), 7.50-7.38 (m, 4H), 4 .81 (s, 2H), 3.53 (s, 2H)

(Example 17)
<Synthesis of 4,6-bis (3,5-dimethoxyphenyl) pyrimidine-2,5-diamine>

In the reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (499 mg, 2.79 mmol), 3,5-dimethoxyphenylboronic acid (1.21 g, 6.66 mmol), sodium carbonate (1.48 g, 14). To a solution of 9.0 mmol) and tetrakis (triphenylphosphine) palladium (0) (323 mg, 0.279 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to give 4,6-bis (3,5-dimethoxyphenyl) pyrimidin-2,5-diamine (0). .769 g, yield 72%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 6.87 (d, J = 2.3 Hz, 4H), 6.54 (t, J = 2.3 Hz, 2H), 4.80 (s, 2H), 3 .84 (s, 12H), 3.58 (s, 2H)

(Example 18)
<Synthesis of 4,6-bis (3,5-bis (trifluoromethyl) phenyl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (349 mg, 1.95 mmol), 3,5-bis (trifluoromethyl) phenylboronic acid (1.15 g, 4.460 mmol), sodium carbonate (1.15 g, 4.460 mmol), sodium carbonate ( To a solution of 1.03 g, 9.69 mmol) and tetrakis (triphenylphosphine) palladium (0) (224 mg, 0.194 mmol) in toluene (20 mL), add ethanol (5 mL) and distilled water (5 mL) at room temperature. In addition, the reaction solution was cooled to room temperature after stirring for 20 hours under heating and reflux conditions in an argon atmosphere. Distilled water (5 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (10 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (10 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) and 4,6-bis (3,5-bis (trifluoromethyl) phenyl) pyrimidin-2,5-diamine. Was obtained (1.03 g, yield 99%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 8.38-8.29 (m, 4H), 8.00-7.98 (m, 2H), 4.87 (s, 2H), 3.44 (s) , 2H)

(Example 19)
<Synthesis of 4,4'-(2,5-diaminopyrimidine-4,6-diyl) dibenzonitrile>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.80 mmol), 4-cyanophenylboronic acid (0.944 g, 6.42 mmol), sodium carbonate (1.48 g, 14.0 mmol). ), And tetrakis (triphenylphosphine) palladium (0) (162 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature, and under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to give 4,4'-(2,5-diaminopyrimidine-4,6-diyl) dibenzonitrile ( 0.354 g, yield 41%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, DMSO-d ₆ ) δ 8.03-7.87 (m, 8H), 6.11 (s, 2H), 4.15 (s, 2H)

(Example 20)
<Synthesis of 4,6-bis (3,4,5-trifluorophenyl) pyrimidine-2,5-diamine>

In the reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (344 mg, 1.92 mmol), 3,4,5-trifluorophenylboronic acid (0.778 g, 4.42 mmol), sodium carbonate (1. To a solution of 02 g, 9.61 mmol) and tetrakis (triphenylphosphine) palladium (0) (112 mg, 0.961 mmol) in toluene (19 mL), ethanol (5 mL) and distilled water (5 mL) were added at room temperature. The reaction solution was cooled to room temperature after stirring for 20 hours under heating and reflux conditions in an argon atmosphere. Distilled water (5 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (10 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (10 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-bis (3,4,5-trifluorophenyl) pyrimidin-2,5-diamine. (0.640 g, yield 90%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.57-7.43 (m, 4H), 4.74 (s, 2H), 3.48 (s, 2H)

(Example 21)
<Synthesis of 4,6-bis (4- (trifluoromethyl) phenyl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (358 mg, 2.00 mmol), 4- (trifluoromethyl) phenylboronic acid (0.873 g, 3.38 mmol), sodium carbonate (1.06 g). To a solution of tetrakis (triphenylphosphine) palladium (0) (116 mg, 0.100 mmol) in toluene (20 mL), ethanol (5 mL) and distilled water (5 mL) were added at room temperature, and argon was added. The reaction solution was cooled to room temperature after stirring for 20 hours under heating and reflux conditions in an atmosphere. Distilled water (5 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (10 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (10 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-bis (4- (trifluoromethyl) phenyl) pyrimidin-2,5-diamine. (0.744 g, yield 93%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.91 (d, J = 8.1 Hz, 4H), 7.78 (d, J = 8.1 Hz, 4H), 4.79 (s, 2H), 3 .45 (s, 2H)

反応容器に、４，６−ジクロロピリミジン−２，５−ジアミン（１．００ｇ、５．５９ｍｍｏｌ）、４−（Ｎ，Ｎ−ジメチルアミノ）フェニルボロン酸（０．９２２ｇ、５．５９ｍｍｏｌ）、炭酸ナトリウム（２．９６ｇ、２７．９ｍｍｏｌ）、及びテトラキス（トリフェニルホスフィン）パラジウム（０）（０．３２３ｇ、０．５６０ｍｍｏｌ）のトルエン（５６ｍＬ）溶液に、エタノール（１４ｍＬ）、及び蒸留水（１４ｍＬ）を室温にて加え、アルゴン雰囲気下にて加熱還流条件にて２０時間撹拌した後に反応液を室温まで冷却した。蒸留水（１６ｍＬ）を加えて撹拌し、分離した水層を酢酸エチル（２０ｍＬ）にて３回抽出した。その後、有機層を全量合わせ、そこに飽和塩化ナトリウム水溶液（２０ｍＬ）を加えて撹拌して洗浄し、再分離した有機層に無水硫酸ナトリウムを加えて脱水し、濾過後の濾液を減圧濃縮した。こうして得られた濃縮液をフラッシュカラムクロマトグラフィー（シリカゲル、ｎ−ヘキサン／酢酸エチル）で精製し、４−クロロ−６−（４−（ジメチルアミノ）フェニル）ピリミジン−２，５−ジアミンを得た（０．７２７ｇ、収率４９％）。 (Comparative Example 1)
<Synthesis of 4-chloro-6- (4- (dimethylamino) phenyl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (1.00 g, 5.59 mmol), 4- (N, N-dimethylamino) phenylboronic acid (0.922 g, 5.59 mmol), carbonic acid. Toluene (56 mL) solution of sodium (2.96 g, 27.9 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.323 g, 0.560 mmol), ethanol (14 mL), and distilled water (14 mL). Was added at room temperature, and the reaction mixture was cooled to room temperature after stirring for 20 hours under heating and reflux conditions under an argon atmosphere. Distilled water (16 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (20 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (20 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4-chloro-6- (4- (dimethylamino) phenyl) pyrimidin-2,5-diamine. (0.727 g, yield 49%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.74-7.63 (m, 2H), 6.82-6.72 (m, 2H), 4.67 (s, 2H), 3.71 (s) , 2H), 3.03 (s, 6H)

(Example 22)
<Synthesis of 4- (4- (dimethylamino) phenyl) -6- (4- (trifluoromethyl) phenyl) pyrimidine-2,5-diamine>

4-Chloro-6- (4- (dimethylamino) phenyl) pyrimidin-2,5-diamine (0.200 g, 0.758 mmol), 4- (trifluoromethyl) phenyl synthesized in Comparative Example 1 in a reaction vessel. Toluene (7.6 mL) of boronic acid (0.158 g, 0.832 mmol), sodium carbonate (0.402 g, 3.79 mmol), and tetrakis (triphenylphosphine) palladium (0) (43.2 mg, 0.379 mmol). ) To the solution, ethanol (1.9 mL) and distilled water (1.9 mL) were added at room temperature, and the mixture was stirred under heating and reflux conditions under an argon atmosphere for 20 hours, and then the reaction solution was cooled to room temperature. Distilled water (2.0 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (3.0 mL). Then, the whole amount of the organic layer is combined, saturated aqueous sodium chloride solution (3.0 mL) is added thereto, and the mixture is stirred and washed. The re-separated organic layer is dehydrated by adding anhydrous sodium sulfate, and the filtrate after filtration is concentrated under reduced pressure. bottom. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) and 4- (4- (dimethylamino) phenyl) -6- (4- (trifluoromethyl) phenyl) pyrimidine. -2,5-Diamine was obtained (267 mg, yield 94%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.97-7.89 (m, 2H), 7.79-7.69 (m, 4H), 6.85-6.76 (m, 2H), 4 .69 (s, 2H), 3.50 (s, 2H), 3.03 (s, 6H)

(Example 23)
<Synthesis of 4,6-bis (4- (dimethylamino) phenyl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (383 mg, 2.00 mmol), 4- (N, N-dimethylamino) phenylboronic acid (0.759 g, 4.60 mmol), sodium carbonate ( To a solution of 1.06 g, 10.0 mmol) and tetrakis (triphenylphosphine) palladium (0) (116 mg, 0.100 mmol) in toluene (20 mL), add ethanol (5 mL) and distilled water (5 mL) at room temperature. In addition, the reaction solution was cooled to room temperature after stirring for 20 hours under heating and reflux conditions in an argon atmosphere. Distilled water (6 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (10 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (10 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to give 4,6-bis (4- (dimethylamino) phenyl) pyrimidine-2,5-diamine ( 0.718 g, yield 99%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.78-7.70 (m, 4H), 6.84-6.75 (m, 4H), 4.62 (s, 2H), 3.55 (s) , 2H), 3.02 (s, 12H)

(Example 24)
<Synthesis of 4,6-bis (4- (methylthio) phenyl) pyrimidine-2,5-diamine>

In a reaction vessel, 4,6-dichloropyrimidine-2,5-distillate (500 mg, 2.79 mmol), 4- (methylthio) phenylboronic acid (1.08 g, 6.43 mmol), sodium carbonate (1.48 g, 28). To a solution of 9.0 mmol) and tetrakis (triphenylphosphine) palladium (0) (161 mg, 0.280 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) were added at room temperature under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to give 4,6-bis (4- (methylthio) phenyl) pyrimidine-2,5-diamine (0). .998 g, yield 99%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.77-7.67 (m, 4H), 7.41-7.32 (m, 4H), 4.67 (s, 2H), 3.48 (s) , 2H), 2.53 (s, 6H)

(Examples 25 and 26)
^{<N 2} - Synthesis of methyl 4,6-diphenyl-pyrimidine-2,5-diamine (Example 25)>

^{<N 2, N} 2 - Synthesis of dimethyl 4,6-diphenyl-pyrimidine-2,5-diamine (Example 26)>

Sodium hydride (60%, 36.6 mg, 0.917 mmol) in a solution of 4,6-diphenylpyrimidine-2,5-diamine (100 mg, 0.382 mmol) synthesized in Example 1 in THF (2.5 mL), And methyl iodide (57.0 μL, 0.917 mmol) were added at 0 ° C., and the temperature was gradually raised to room temperature. The mixture was stirred at room temperature for 24 hours under an argon atmosphere. A saturated aqueous sodium hydrogen carbonate solution (2.5 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with chloroform (5 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (5 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. Thus obtained concentrate was purified by flash column chromatography (silica gel, n- hexane / ethyl acetate), ^{N 2} - methyl-4,6-diphenyl-pyrimidine-2,5-diamine (47.7 mg, yield 45 %), and ^N 2, ^{N 2} - dimethyl-4,6-diphenyl-pyrimidine-2,5-diamine (44.9 mg, 41% yield), respectively.

^{The 1} H NMR measurement results of each of the obtained compounds are as follows.
<< N ² -Methyl-4,6-diphenylpyrimidine-2,5-diamine >>
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.85-7.76 (m, 4H), 7.55-7.47 (m, 4H), 7.47-7.39 (m, 2H), 4 .75 (d, J = 4.9Hz, 1H), 3.42 (s, 2H), 3.03 (d, J = 4.9Hz, 3H)

<< N ² , N ² -dimethyl-4,6-diphenylpyrimidine-2,5-diamine >>
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.90-7.83 (m, 4H), 7.54-7.40 (m, 6H), 3.41 (s, 2H), 3.20 (s) , 6H)

(Example 27)
<Synthesis of N- (5-amino-4,6-diphenylpyrimidine-2-yl) butyramide>

Butyroyl chloride (79.6 μL, 0.764 mmol) was added to a pyridine (1.1 mL) solution of 4,6-diphenylpyrimidine-2,5-diamine (100 mg, 0.382 mmol) synthesized in Example 1 to create an argon atmosphere. After stirring under heating and reflux conditions for 20 hours, the reaction solution was cooled to room temperature. A 2M aqueous hydrogen chloride solution (2.5 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with chloroform (5 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (5 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain N- (5-amino-4,6-diphenylpyrimidine-2-yl) butyramide (46.8 mg, yield). A rate of 37%) was obtained.

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (500 MHz, CDCl ₃ ) δ 7.92-7.76 (m, 4H), 7.59-7.51 (m, 3H), 7.51-7.44 (m, 2H), 3 .92 (s, 2H), 2.73 (brs, 2H), 1.77 (dt, J = 7.4, 7.4Hz, 2H), 0.99 (t, J = 7.4Hz, 3H)

(Example 28)
<Synthesis of 2- (methylthio) -4,6-diphenylpyrimidine-5-amine>

In a reaction vessel, 4,6-dichloro-2- (methylthio) pyrimidin-5-amine (0.400 g, 1.90 mmol), phenylboronic acid (534 mg, 4.37 mmol), sodium carbonate (1.01 g, 9. To a solution of 50 mmol) and tetrakis (triphenylphosphine) palladium (0) (110 mg, 0.095 mmol) in toluene (19 mL), ethanol (5 mL) and distilled water (5 mL) were added at room temperature under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (5 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (10 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (10 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 2- (methylthio) -4,6-diphenylpyrimidine-5-amine (0.432 g, yield). Rate 77%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.87-7.79 (m, 4H), 7.57-7.43 (m, 6H), 3.86 (s, 2H), 2.60 (s) , 3H)

(Example 29)
<Synthesis of 2- (methylsulfonyl) -4,6-diphenylpyrimidine-5-amine>

Metachloroperbenzoic acid (77%, 193 mg, 0.) in a solution of 2- (methylthio) -4,6-diphenylpyrimidine-5-amine (120 mg, 0.409 mmol) in dichloromethane (3.1 mL) synthesized in Example 28. 859 mmol) was added at 0 ° C. and the temperature was gradually raised to room temperature. The mixture was stirred at room temperature for 24 hours under an argon atmosphere. A 10% aqueous sodium thiosulfate solution (15 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with chloroform (6 mL). Then, all the organic layers were combined, saturated aqueous sodium hydrogen carbonate solution (6 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. .. The concentrate thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) and 2- (methylsulfonyl) -4,6-diphenylpyrimidine-5-amine (127.4 mg, yield 96). %) Was obtained.

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl3) δ 7.88-7.78 (m, 4H), 7.61-7.49 (m, 6H), 4.58 (s, 2H), 3.35 (s, 3H)

(Example 30)
<Synthesis of 2-methoxy-4,6-diphenylpyrimidine-5-amine>

Potassium tert-butoxide (85.7 mg, 85.7 mg) in a solution of 2- (methylsulfonyl) -4,6-diphenylpyrimidine-5-amine (50.0 mg, 0.154 mmol) in methanol (1.6 mL) synthesized in Example 29. 0.768 mmol) was added at room temperature. The mixture was stirred at room temperature for 24 hours under an argon atmosphere. Tetrahydrofuran (1.6 mL) was added, and the mixture was further stirred at room temperature for 24 hours. The solvent was distilled off under reduced pressure, ethyl acetate (10 mL) and saturated aqueous ammonium chloride solution (2 mL) were added, and the mixture was stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (2 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (2 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrate thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to give 2-methoxy-4,6-diphenylpyrimidine-5-amine (42.5 mg, 99% yield). Obtained.

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.91-7.80 (m, 4H), 7.57-7.43 (m, 6H), 4.02 (s, 3H), 3.73 (s) , 2H)

(Example 31)
<Synthesis of 2,4,6-triphenylpyrimidine-5-amine>

2- (Methylthio) -4,6-diphenylpyrimidine-5-amine (50.1 mg, 0.170 mmol) synthesized in Example 28, and nickel (2) dichlorodiphenylphosphinoetan complex (1.0 mg, 1. Phenylmagnesium bromide (1.0 M tetrahydrofuran solution, 0.27 mL, 0.27 mmol) was added to a 7 μmol) toluene (0.9 mL) solution at room temperature, and then the temperature was raised to 60 ° C. The mixture was stirred at 60 ° C. for 24 hours under an argon atmosphere. A 1 M aqueous hydrochloric acid solution (5 mL) was added and stirred, and a saturated aqueous sodium hydrogen carbonate solution (5 mL) was added to the separated organic layer and stirred. The re-separated aqueous layer was extracted 3 times with ethyl acetate (3 mL). Then, all the organic layers were combined, anhydrous sodium sulfate was added for dehydration, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 2,4,6-triphenylpyrimidine-5-amine (7.0 mg, yield 13%). rice field.

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 8.53-8.42 (m, 2H), 7.98-7.88 (m, 4H), 7.61-7.53 (m, 4H), 7 .53-7.47 (m, 2H), 7.41-7.36 (3H), 4.11 (s, 2H)

(Comparative Example 2)
<Synthesis of 4,6-dichloro-N, N-dimethyl-2- (methylthio) pyrimidine-5-amine>

Sodium hydride (60%, 136 mg, 3.40 mmol) in a solution of 2- (methylthio) -4,6-dichloropyrimidine-5-amine (298 mg, 1.42 mmol) in N, N-dimethylformamide (9.0 mL). ) And methyl iodide (440 μL, 7.10 mmol) were added at 0 ° C., and the temperature was gradually raised to room temperature. The mixture was stirred at room temperature for 24 hours under an argon atmosphere. A saturated aqueous sodium hydrogen carbonate solution (9 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (20 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (5 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The resulting concentrate was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to purify 4,6-dichloro-N, N-dimethyl-2- (methylthio) pyrimidine-5-amine (72. 0 mg, yield 21%) were obtained respectively.

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 2.82 (s, 6H), 2.55 (s, 3H)

(Example 32)
<Synthesis of N, N-dimethyl-2- (methylthio) -4,6-diphenylpyrimidine-5-amine>

4,6-Dichloro-N, N-dimethyl-2- (methylthio) pyrimidin-5-amine (71.9 mg, 0.301 mmol) and phenylboronic acid (84.7 mg) obtained in Comparative Example 2 were placed in a reaction vessel. , 0.692 mmol), sodium carbonate (160 mg, 1.51 mmol), and tetrakis (triphenylphosphine) palladium (0) (17.5 mg, 0.0151 mmol) in a toluene (3 mL) solution of ethanol (0.8 mL). , And distilled water (0.8 mL) was added at room temperature, and the reaction mixture was cooled to room temperature after stirring under heating and reflux conditions under an argon atmosphere for 20 hours. Distilled water (1 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (2 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (2 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain N, N-dimethyl-2- (methylthio) -4,6-diphenylpyrimidine-5-amine. (65.5 mg, yield 68%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.71-7.65 (m, 4H), 7.50-7.40 (m, 6H), 2.60 (s, 3H), 2.33 (s) , 6H)

(Comparative Example 3)
The following compounds were used as Comparative Example 3. The following compounds were synthesized by known methods.

(Comparative Example 4)
The following compounds were used as Comparative Example 4. The following compounds were synthesized by known methods.

(Comparative Example 5)
<Synthesis of [1,1': 3', 1''-terphenyl] -2', 5'-diamine>

In a reaction vessel, 1,4-diamino-3,5-dibromobenzene (0.532 g, 2.00 mmol), phenylboronic acid (561 mg, 4.60 mmol), sodium carbonate (1.06 g, 10.0 mmol), and To a solution of tetrakis (triphenylphosphine) palladium (0) (116 mg, 0.100 mmol) in toluene (20 mL), ethanol (5 mL) and distilled water (5 mL) are added at room temperature, and the mixture is heated under reflux conditions under an argon atmosphere. After stirring for 20 hours, the reaction solution was cooled to room temperature. Distilled water (6 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (10 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (10 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain [1,1': 3', 1''-terphenyl] -2', 5'-diamine. Obtained (0.453 g, yield 87%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.56-7.48 (m, 4H), 7.48-7.40 (m, 4H), 7.39-7.30 (m, 2H), 6 .59 (s, 2H), 3.43 (s, 4H)

(Comparative Example 6)
<Synthesis of 4-chloro-6-phenylpyrimidine-2,5-diamine>

4,6-Dichloropyrimidin-2,5-distillate (1.00 g, 5.59 mmol), phenylboronic acid (0.681 g, 5.59 mmol), sodium carbonate (2.96 g, 27.9 mmol) in a reaction vessel. To a solution of tetrakis (triphenylphosphine) palladium (0) (323 mg, 0.279 mmol) in toluene (56 mL), ethanol (14 mL) and distilled water (14 mL) were added at room temperature and heated under an argon atmosphere. After stirring under reflux conditions for 20 hours, the reaction solution was cooled to room temperature. Distilled water (6 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (20 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (20 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4-chloro-6-phenylpyrimidine-2,5-diamine (590 mg, yield 48%). ..

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.74-7.63 (m, 2H), 7.54-7.40 (m, 3H), 4.80 (s, 2H), 3.68 (s) , 2H)

(Example 33)
<Synthesis of 4-phenylpyrimidine-2,5-diamine>

5% Pd / C (55 wt%, 41.2 mg) in an ethanol (1.8 mL) solution of 4-chloro-6-phenylpyrimidine-2,5-diamine (100 mg, 0.453 mmol) synthesized in Comparative Example 6. And sodium acetate (74.3 mg, 0.906 mmol) were added, and the mixture was stirred at room temperature for 16 hours under a hydrogen atmosphere. After substituting under an argon atmosphere, the solution was filtered through Celite. A saturated aqueous sodium hydrogen carbonate solution (3 mL) was added to the obtained solution, and the mixture was stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (3 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (3 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4-phenylpyrimidine-2,5-diamine (59.1 mg, yield 70%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 7.99 (s, 1H), 7.75-7.68 (m, 2H), 7.54-7.39 (m, 3H), 4.66 (s) , 2H), 3.37 (s, 2H)

(Example 34)
<Synthesis of 4,6-diphenylpyrimidine-5-amine>

In a reaction vessel, 5-amino-4,6-dichloropyrimidine (0.458 g, 2.80 mmol), phenylboronic acid (0.783 g, 6.42 mmol), sodium carbonate (1.48 g, 14.0 mmol), and To a solution of tetrakis (triphenylphosphine) palladium (0) (161 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) are added at room temperature, and the mixture is heated under reflux conditions under an argon atmosphere. After stirring for 20 hours, the reaction solution was cooled to room temperature. Distilled water (6 mL) was added and stirred, and the separated aqueous layer was extracted 3 times with ethyl acetate (12 mL). Then, all the organic layers were combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, and the mixture was stirred and washed. The re-separated organic layer was dehydrated by adding anhydrous sodium sulfate, and the filtered filtrate was concentrated under reduced pressure. The concentrated solution thus obtained was purified by flash column chromatography (silica gel, n-hexane / ethyl acetate) to obtain 4,6-diphenylpyrimidine-5-amine (0.682 g, yield 98%).

^{The 1} H NMR measurement results of the obtained compound are as follows.
^{1 1} H NMR (400 MHz, CDCl ₃ ) δ 8.79 (s, 1H), 7.87-7.76 (m, 4H), 7.59-7.42 (m, 7H), 4.08 (s) , 2H)

The compounds synthesized in Examples 1 to 34 are as follows.

The compounds of Comparative Examples 1 to 6 are as follows.

Chloroform solutions of each compound of Examples 1 to 34 and Comparative Examples 1 to 6 were prepared, and the absorption spectrum (0.2 μmol / mL) and the fluorescence spectrum (0.02 μmol / mL) were measured. Each spectrum was measured using JASCO FP-8600. The measurement conditions are as follows. The results are shown in Table 1-1 and Table 1-2.
〔Measurement condition〕
Measurement mode Wavelength scan Excitation wavelength 375 nm
Fluorescence start wavelength 390 nm
Fluorescence end wavelength 800 nm
Scan speed 1000 nm / min Excitation side slit 5.0 nm
Fluorescent side slit 5.0 nm

The fluorescence quantum efficiency was determined by the absolute method using the integrating sphere unit ILF-835 attached to the spectrofluorometer.

The compound of the present invention can be suitably used as a luminescent compound.

ただし、前記一般式（１）中、Ｒ^１は、水素原子、及び置換基のいずれかを表す。Ｒ^２、及びＲ^３は、それぞれ独立して、水素原子、及び置換基のいずれかを表す。Ｒ^４は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^１は、置換基を有していてもよい芳香族基を表す。Ｒ^５は、水素原子、及び下記一般式（２）で表される基のいずれかを表す。

ただし、前記一般式（２）中、Ｒ^６は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^２は、置換基を有していてもよい芳香族基を表す。
＜２＞ Ｒ^１が、水素原子、置換基を有していてもよいアリール基、置換基を有していてもよいアルコキシ基、置換基を有していてもよいアルキルチオ基、置換基を有していてもよいアルキルスルホニル基、及び下記一般式（３）で表される基のいずれかである前記＜１＞に記載の化合物である。

ただし、前記一般式（３）中、Ｒ^１１、及びＲ^１２は、それぞれ独立して、水素原子、及び置換基のいずれかを表す。
＜３＞ Ｒ^２、及びＲ^３が、水素原子、及びアルキル基のいずれかである前記＜１＞から＜２＞のいずれかに記載の化合物である。
＜４＞ Ａｒ^１の前記芳香族基における芳香族環、及びＡｒ^２の前記芳香族基における芳香族環が、それぞれ独立して、下記構造式のいずれかである前記＜１＞から＜３＞のいずれかに記載の化合物である。

＜５＞ Ａｒ^１が有していてもよい前記置換基が、ハロゲン原子、シアノ基、アルキル基、アミノ基、及びアルコキシ基のいずれかであり、
Ａｒ^２が有していてもよい前記置換基が、ハロゲン原子、シアノ基、アルキル基、アミノ基、及びアルコキシ基のいずれかである、前記＜１＞から＜４＞のいずれかに記載の化合物である。
＜６＞ 下記一般式（１）で表されることを特徴とする発光化合物である。

ただし、前記一般式（１）中、Ｒ^１は、水素原子、及び置換基のいずれかを表す。Ｒ^２、及びＲ^３は、それぞれ独立して、水素原子、及び置換基のいずれかを表す。Ｒ^４は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^１は、置換基を有していてもよい芳香族基を表す。Ｒ^５は、水素原子、及び下記一般式（２）で表される基のいずれかを表す。

ただし、前記一般式（２）中、Ｒ^６は、直接結合、ビニレン基、１，３−ブタジエニレン基、エチニレン基、及び１，３−ブタジイニレン基のいずれかを表す。Ａｒ^２は、置換基を有していてもよい芳香族基を表す。
＜７＞ Ｒ^１が、水素原子、置換基を有していてもよいアリール基、置換基を有していてもよいアルコキシ基、置換基を有していてもよいアルキルチオ基、置換基を有していてもよいアルキルスルホニル基、及び下記一般式（３）で表される基のいずれかである前記＜６＞に記載の発光化合物である。

ただし、前記一般式（３）中、Ｒ^１１、及びＲ^１２は、それぞれ独立して、水素原子、及び置換基のいずれかを表す。
＜８＞ Ｒ^２、及びＲ^３が、水素原子、及びアルキル基のいずれかである前記＜６＞から＜７＞のいずれかに記載の発光化合物である。
＜９＞ Ａｒ^１の前記芳香族基における芳香族環、及びＡｒ^２の前記芳香族基における芳香族環が、それぞれ独立して、下記構造式のいずれかである前記＜６＞から＜８＞のいずれかに記載の発光化合物である。

＜１０＞ Ａｒ^１が有していてもよい前記置換基が、ハロゲン原子、シアノ基、アルキル基、アミノ基、及びアルコキシ基のいずれかであり、
Ａｒ^２が有していてもよい前記置換基が、ハロゲン原子、シアノ基、アルキル基、アミノ基、及びアルコキシ基のいずれかである、前記＜６＞から＜９＞のいずれかに記載の発光化合物である。
＜１１＞ ４００ｎｍ〜６００ｎｍに蛍光極大波長を有する前記＜６＞から＜１０＞のいずれかに記載の発光化合物である。 Aspects of the present invention are, for example, as follows.
<1> A compound characterized by being represented by the following general formula (1).

However, in the general formula (1), R ¹ represents either a hydrogen atom or a substituent. R ² and R ³ independently represent either a hydrogen atom or a substituent. R ⁴ represents a direct bond, a vinylene group, 1,3-butadienylene group, and an ethynylene group, and 1,3-butadiynylene groups. Ar ¹ represents an aromatic group which may have a substituent. R ⁵ represents either a hydrogen atom or a group represented by the following general formula (2).

However, in the general formula (2), R ⁶ represents any of a direct bond, a vinylene group, a 1,3-butadienylene group, an ethynylene group, and a 1,3-butadienylene group. Ar ² represents an aromatic group which may have a substituent.
<2> R ¹ has a hydrogen atom, an aryl group which may have a substituent, an alkoxy group which may have a substituent, an alkylthio group which may have a substituent, and a substituent. The compound according to <1>, which is any of an alkylsulfonyl group which may be used and a group represented by the following general formula (3).

However, in the general formula (3), R ¹¹ and R ¹² independently represent either a hydrogen atom or a substituent.
<3> The compound according to any one of <1> to <2>, wherein ^{R 2} and R ^{3 are either a hydrogen atom or an alkyl group.}
<4> ^{The aromatic ring in the aromatic group of Ar 1 and} the aromatic ring in the aromatic group of Ar ² are independently one of the following structural formulas from <1> to <3>. The compound described in any of the above.

<5> The ^{substituent that Ar 1} may have is any one of a halogen atom, a cyano group, an alkyl group, an amino group, and an alkoxy group.
The compound according to any one of <1> to <4>, wherein the substituent that Ar ² may have is any one of a halogen atom, a cyano group, an alkyl group, an amino group, and an alkoxy group. Is.
<6> A luminescent compound represented by the following general formula (1).

However, in the general formula (1), R ¹ represents either a hydrogen atom or a substituent. R ² and R ³ independently represent either a hydrogen atom or a substituent. R ⁴ represents a direct bond, a vinylene group, 1,3-butadienylene group, and an ethynylene group, and 1,3-butadiynylene groups. Ar ¹ represents an aromatic group which may have a substituent. R ⁵ represents either a hydrogen atom or a group represented by the following general formula (2).

However, in the general formula (2), R ⁶ represents any of a direct bond, a vinylene group, a 1,3-butadienylene group, an ethynylene group, and a 1,3-butadienylene group. Ar ² represents an aromatic group which may have a substituent.
<7> R ¹ has a hydrogen atom, an aryl group which may have a substituent, an alkoxy group which may have a substituent, an alkylthio group which may have a substituent, and a substituent. The luminescent compound according to <6>, which is any of an alkylsulfonyl group which may be used and a group represented by the following general formula (3).

However, in the general formula (3), R ¹¹ and R ¹² independently represent either a hydrogen atom or a substituent.
<8> The luminescent compound according to any one of <6> to <7>, wherein ^{R 2} and R ^{3 are either hydrogen atoms or alkyl groups.}
<9> ^{The aromatic ring in the aromatic group of Ar 1 and} the aromatic ring in the aromatic group of Ar ² are independently one of the following structural formulas, from <6> to <8>. It is a luminescent compound according to any one of.

<10> The ^{substituent that Ar 1} may have is any one of a halogen atom, a cyano group, an alkyl group, an amino group, and an alkoxy group.
The light emission according to any one of <6> to <9>, wherein the substituent that Ar ² may have is any one of a halogen atom, a cyano group, an alkyl group, an amino group, and an alkoxy group. It is a compound.
<11> The luminescent compound according to any one of <6> to <10>, which has a maximum fluorescence wavelength of 400 nm to 600 nm.

Claims (1)

A compound characterized by being represented by any of the following structural formulas.