WO2007069498A1

WO2007069498A1 - Compound for electroluminescent device and method for producing same

Info

Publication number: WO2007069498A1
Application number: PCT/JP2006/324243
Authority: WO
Inventors: Takaki Kanbara; Takakazu Yamamoto; Yasuhiko Shirota; Nobutaka Fujimoto; Yuichi Onoda
Original assignee: Sumitomo Seika Chemicals Co., Ltd.; Tokyo Institute Of Technology
Priority date: 2005-12-14
Filing date: 2006-12-05
Publication date: 2007-06-21
Also published as: JP2007186490A; TW200736222A

Abstract

Disclosed is a low molecular weight organic compound having photo-electron conversion function and capable of forming an amorphous film having excellent heat resistance by itself. Also disclosed is a method for producing such a low molecular weight organic compound. Specifically disclosed are a compound represented by the general formula (I) below and a method for producing such a compound. (I) (In the formula, R1-R3 independently represent a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a carbamoyl group, an alkyl group having 1-10 carbon atoms or an alkanoyl group having 1-10 carbon atoms, and they may be the same or different from each other; V represents a nitrogen atom or a carbon atom; two W’s both represent nitrogen atoms or carbon atoms at the same time; and V and W’s may be the same as or different from each other.)

Description

Specification

Compound for electroluminescent device and method for producing the same

Technical field

TECHNICAL FIELD [0001] The present invention relates to a low molecular weight organic compound useful as a charge transport material, a light emitting layer material, and a photosensitive part material such as a photoconductive imaging element in an electroluminescent (electral luminescence: EL) element, and a method for producing the same. .

Background art

[0002] Conventionally, in electronic devices such as electroluminescent elements and photoconductive imaging elements, thin films of low molecular weight organic compounds having a light-to-electron conversion function, especially amorphous films with high flexibility, have been suitably used. Yes. These low molecular weight organic compounds include, for example, N, N, one diphenyl, one N, N, one bis (3-methylphenol), one, one, one biphenyl —4, 4, one diamine. N, N, Iji [(1 Naphthalene) 1 N, N, I Diphenyl] — 1, 1'-biferro-4, 4'-diamin etc. are known (see Non-Patent Document 1) As an amorphous film, for those amorphous films that are strong themselves, or those having poor film formability, a Noinder resin such as polycarbonate resin and the low molecular weight organic compound are dissolved in an organic solvent, An amorphous film obtained by coating and drying is used (see Non-Patent Document 2).

However, since amorphous films formed using these conventionally known low molecular weight organic compounds have a tendency to crystallize over time, they have poor heat resistance and durability. There is a problem that it is sufficient, and there is a problem that when the binder resin is used, the function of the low molecular weight organic compound is diluted in the binder resin.

[0004] Non-Patent Document 1: Electronic Materials, December 2001, pp. 18-23 (2001)

Non-Patent Document 2: Appl. Phys. Lett., Vol. 61, p. 761 (1992)

Disclosure of the invention

Problems to be solved by the invention

[0005] The present invention aims to provide a low molecular weight organic compound that can form an amorphous film having photoelectron transformation and excellent heat resistance by itself, and a method for producing the same. Target.

Means for solving the problem

[0006] The present invention relates to a low molecular weight organic compound and a method for producing the same as described below.

That is, the present invention relates to the general formula (I):

[0007] [Chemical 1]

[0008] (In the formula, each of! ^-Is independently a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubermoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoyl having 1 to 10 carbon atoms. May be the same or different, V represents a nitrogen atom or carbon atom, two Ws simultaneously represent a nitrogen atom or carbon atom, and V and W may be the same It is different and relates to a compound represented by

[0009] The compound of the present invention is preferably represented by the general formula (1)! ^ ~ Are all hydrogen atoms.

The present invention also provides a general formula (Π):

[0010] [Chemical 2]

(In the formula, R ¹ represents a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubamoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoyl group having 1 to 10 carbon atoms, and V represents nitrogen. Dihalogeno monocyclic compounds represented by the general formula (ΠΙ): [0012] [Chemical 3]

(Wherein R ² and R ³ are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubamoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 may be the same or different and W may be the same or different. W represents a nitrogen atom or a carbon atom.) General formula (I) characterized by reacting in the presence of a catalyst containing a compound and a base:

[0014] [Chemical 4]

[0015] (wherein! ^ ~ Are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubermoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoyl having 1 to 10 carbon atoms) May be the same or different, V represents a nitrogen atom or carbon atom, two Ws simultaneously represent a nitrogen atom or carbon atom, and V and W may be the same It is different and relates to a method for producing a compound represented by

Hereinafter, the present invention will be described in detail.

The compound of the present invention is a novel substance represented by the following general formula (I).

[0017] [Chemical 5] R ¹

[0018] In the general formula (I), each of the scales ¹ to! ^ Is independently a hydrogen atom, a hydroxyl group, a carboxy group, a cyan group, a strong rubamoyl group, or an alkyl group having 1 to C carbon atoms: Or an alkanoyl group having 1 to 10 carbon atoms, which may be the same or different!

! Examples of the alkyl group having 1 to 10 carbon atoms represented by ^ to include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, Examples include n-pentyl group, isopentyl group, neopentyl group, n xyl group, isohexyl group, n-octyl group and n-decyl group.

! Examples of the alkanol group having 1 to 10 carbon atoms represented by ^ to include a methanol group, an ethanol group, a butanol group, and a decanol group.

In the general formula (I), V represents a nitrogen atom or a carbon atom, two Ws simultaneously represent a nitrogen atom or a carbon atom, and V and W may be the same or different.

[0020] As specific examples of the compound represented by the general formula (I),

1) In the general formula (I), V and W are both nitrogen atoms. General Formula (1): [0021] [Chemical Formula 6]

[0022] (In the formula,! ^-Are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, Group, a strong rubermoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanol group having 1 to 10 carbon atoms, which may be the same or different. ) 2, 6-bis [di (pyridine-1-yl) amino] pyridine compound,

2) In the general formula (I), the general formula (2) in which V is a carbon atom and W is a nitrogen atom:

[0023] [Chemical 7]

[0024] (wherein! ^ ~ Are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubermoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoyl having 1 to 10 carbon atoms) 1, 3-bis [di (pyridin-2-yl) amino] benzene compounds represented by the following formulas, which may be the same or different:

3) In the general formula (I), V is a nitrogen atom and W is a carbon atom (3):

[0025] [Chemical 8]

[0026] (wherein! ^-Are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubamoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoy having 1 to 10 carbon atoms. These groups may be the same or different. ), 2,6-bis [(phenol) (pyridine-2-yl) amino] pyridine compound, and

4) In the general formula (I), V and W are both carbon atoms.

[Chemical 9]

[0028] (wherein! ^ ~ Are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubermoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoyl having 1 to 10 carbon atoms) A 1,3-bis [(phenol) (pyridine-2-yl) amino] benzene compound represented by the following formula: .

[0029] Specific examples of the compound represented by the general formula (I) include, for example, as the general formula (1), 2, 6-bis [di (pyridine-1-yl) amino] pyridine, 2, 6-bis [di (4-methylpyridin-2-yl) amino] pyridine, 2,6-bis [di (5-methylpyridine-2-yl) amino] pyridine, 2,6-bis [di (6-Methylpyridine-1-yl) amino] pyridine, 2,6-bis [di (4-ethylpyridine-2-amino) pyridine], 2,6-bis [di (5-ethylpyridine-2-) Yl) amino] pyridine, 2, 6-bis [di (6-ethylpyridine-2-yl) amino] pyridin, 2,6-bis [di (4-n-propylpyridine-2-yl) amino] Pyridine, 2,6-bis [di (5-n-propylpyridine-2-yl) amino] pyridine, 2,6-bis [di (6-n-propylpyridine-2-yl) a )] Pyridine, 2,6-bis [di (4-isopropylpyridine-2-yl) amino] pyridine, 2,6-bis [di (5-isopropylpyridine-2-yl) amino] pyridine, 2 , 6-bis [di (6-isopropylpyridine-1-yl) amino] pyridine, 2,6-bis [di (4-n-butylpyridine-2-yl) amino] pyridine, 2, 6- Bis [di (5-n-butylpyridine-2-yl) amino] pyridine, 2,6-bis [di (6-n-butylpyridine-2-yl) amino] pyridine, 2,6-bis [ Di (4-isobutylpyridine-2-yl) amino] pyri Gin, 2, 6-bis [di (5-isobutylpyridine-2-yl) amino] pyridine, 2,6-bis [di (6-isobutylpyridine-2-yl) amino] pyridine, 2, 6- Bis [di (4-sec-butyrubiridin-2-yl) amino] pyridine, 2,6-bis [di (5-sec-butylpyridine-2-yl) amino] pyridine, 2,6-bis [ Di (6-sec-butylpyridine-2-yl) amino] pyridine, 2,6-bis [di (4-tert-butylpyridine-2-yl) amino] pyridine, 2,6-bis [di ( 5-tert-butylpyridine-2-yl) amino] pyridine, 2,6-bis [di (6-tert-butylpyridine-2-yl) amino] pyridine, 2,6-bis [di (4- n-pentylvinylidine-2-yl) amino] pyridine, 2,6-bis [di (5-n-pentylvinylidine-2-yl) amino] pyridine, 2,6-bis [di (6 — N-pentylviridine-2-yl) amino] pyridine, 2,6-bis [di (4-isopentylviridine-2-yl) amino] pyridine, 2,6-bis [di (5-isopentyl) Bilysine-2-yl) amino] pyridine, 2,6-bis [di (6-isopentylviridine-2-yl) amino] pyridine, 2,6-bis [di (4-neopentylviridine-1-2] ) Amino] pyridine, 2,6-bis [di (5-neopentylviridine-2-yl) amino] pyridine, 2,6-bis [di (6-neopentylviridine-2-yl) amino] Pyridine, 2,6-bis [di (4-n-hexylpyridine-1-yl) amino] pyridine, 2,6-bis [di (5-n-hexylpyridine-2-yl) amino] Pyridine, 2,6-bis [di (6-n-hexylvinyl lysine-2-yl) amino] pyridine, 2,6-bis [di (4-isohexyl] Pyridine-2-yl) amino] pyridine, 2,6-bis [di (5-isohexylpyridine-1-2-yl) amino] pyridine, 2,6-bis [di (6-isohexylpyridine) 2-yl) amino] pyridine, 2,6-bis [di (4-n-octylviridine-2-yl) amino] pyridine, 2,6-bis [di (5-n-octylviridine-2- ) Amino] pyridine, 2,6-bis [di (6-n-octylviridine-2-yl) amino] pyridine, 2,6-bis [di (4-n-decylviridine-2-yl) amino] Pyridine, 2,6-bis [di (5-n-decylviridine-2-yl) amino] pyridine, 2,6-bis [di (6-n-decylviridine-1-2-yl) amino] pyridine, 2 , 6-bis [di (4-hydroxylpyridine-2-yl) amino] pyridine, 2,6-bis [di (5-hydroxylpyridine-2-yl) Mino] pyridine, 2,6-bis [di (6-hydroxylpyridine-2-yl) amino] pyridin, 2,6-bis [di (4-alkanoylpyridine-2-yl) amino] pyridine 2, 6-bis [di (5-alkanoylpyridine-2-yl) amino] pyridine, 2,6-bis [di (6-alkano Ylpyridine—2-yl) amino] pyridine, 2, 6 bis [di (4—force rubamoylviridine—2 yl) amino] pyridine, 2,6 bis [di (5—force rubamoylviridine 2 yl) Amino] pyridine, 2, 6 bis [di (6-branyl pyridine] 2-amino) pyridine, 2, 6-bis [di (4-carboxylpyridine-2-yl) amino] pyridine, 2 , 6 bis [di (5-carboxylpyridine-2-yl) amino] pyridine, 2,6 bis [di (6-carboxylpyridine-2-yl) amino] pyridine, 2,6 bis [di (4 Cyanopyridine-2-yl) amino] pyridine, 2,6 bis [di (5 Cyanpyridine-1-2-yl) amino] pyridine, 2,6 bis [di (6 Cyanpyridine1-2-yl) amino] pyridine,

In general formula (2), 1,3 bis [di (pyridine-2-yl) amino] benzene, 1,3 bis [di (4-methylpyridine-2-yl) amino] benzene, 1,3 bis [Di (5-methylpyridin-2-yl) amino] benzene, 1,3 bis [di (6-methylpyridine-2-yl) amino] benzene, 1,3 bis [di (4-ethylpyridine-2— Yl) amino] benzene, 1,3 bis [di (5-ethylpyridin-2-yl) amino] benzene, 1,3 bis [di (6 ethylpyridine-2-yl) amino] benzene, 1, 3 Bis [di (4-n-propylpyridine-2-yl) amino] benzene, 1,3 bis [di (5-n-propylpyridine-2-yl) amino] benzen, 1,3 bis [di (6-N-propynolepyridine-1-2-inole) amino] benzene, 1,3 bis [di (4-isopropylpyridine-1-2-yl) amino] ben 1,3 bis [di (5-isopropylpyridyl-2-yl) amino] benzene, 1,3 bis [di (6-isopropylpyridine-2-yl) amino] benzene, 1,3 bis [ Di (4-n-butylpyridine-2-yl) amino] benzene, 1,3bis [di (5-n-butylpyridine-2-yl) amino] benzene, 1,3-bis [di (6 — N-Butylpyridine— 2-yl) amino] benzene, 1,3 bis [di (4-isobutylviridine-2-yl) amino] benzene, 1,3 bis [di (5-isobutylpyridine —2— Yl) amino] benzene, 1,3 bis [di (6-isobutylpyridine-2-yl) amino] benzene, 1,3 bis [di (4 sec butylpyridine-2-yl) amino] benzene, 1 , 3 bis [di (5-sec butylpyridine-2-yl) amino] benzene, 1,3 bis [di (6 sec butylpyridine 2 yl Amino] benzene, 1,3 bis [di (4 tert-butyryridine-2-yl) amino] benzene, 1,3 bis [di (5-tert-butylpyridine-2-yl) amino] benzene, 1 , 3 Bis [di (6-tert-butylpyridine-2-yl) amino] Benzene, 1,3-bis [di (4-n-pentylviridine-2-yl) amino] benzene, 1,3-bis [di (5-n-pentylviridine-2-yl) amino] benzene, 1,3-bis [di (6-n-pentylviridine-2-yl) amino] benzene, 1,3-bis [di (4-isopentylviridine-2-yl) amino] benzene, 1, 3— Bis [di (5-isopentylviridine-2-yl) amino] benzene, 1,3-bis [di (6-isopentylviridine-2-yl) amino] benzene, 1,3-bis [di (4-Neopentylpyridine-2-yl) amino] benzene, 1,3-bis [di (5-Neopentylviridine-2-yl) amino] benzene, 1,3-bis [di (6-neo Pentylviridine—2-yl) amino] benzene, 1,3-bis [di (4-n-hexylpyridine-2-yl) amino] benzene, 1 , 3-bis [di (5-n-hexylpyridine-2-yl) amino] benzene, 1,3-bis [di (6-n-hexylpyridine-2-yl) amino] benzene, 1,3-bis [di (4-isohexylpyridine-1-yl) amino] benzene, 1,3-bis [di (5-isohexylpyridine-1-yl) amino] benzene, 1, 3-bis [di (6-isohexylpyridine-2-yl) amino] benzene, 1,3-bis [di (4-n-octylpyridin-2-yl) amino] benzene, 1, 3 —Bis [di (5-n-octylviridine-2-yl) amino] benzene, 1,3-bis [di (6-n-octylviridine-2-yl) amino] benzen, 1,3-bis [ Di (4-n-decylviridine-2-yl) amino] benzene, 1,3-bis [di (5-n-decylviridine-2-yl) amino] benzene, 1,3-bis [di (6- n Decylpyridine—2-yl) amino] benzene, 1,3-bis [di (4-hydroxylpyridine-2-yl) amino] benzene, 1,3-bis [di (5-hydroxylpyridine) Le) amino] benzene, 1,3-bis [di (6-hydroxylpyridine-2-yl) amino] benzene, 1,3-bis [di (4-alkanoylpyridine-2-yl) amino] Benzene, 1,3-bis [di (5-alkanoylpyridine-2-yl) amino] benzene, 1,3-bis [di (6-alkanoylpyridin-2-yl) amino] benzene, 1, 3-bis [di (4-force rubermoylviridine-2-yl) amino] benzene, 1,3-bis [di (5-forcerubamoylviridine-2-yl) amino] benzene, 1, 3 —Bis [di (6—force rubamoylpyridine-2-yl) amino] benzene, 1, 3—bis [di (4-carboxyl Pyridine-2-yl) amino] benzene, 1,3-bis [di (5-force ruboxylpyridine-2-yl) amino] benzene, 1,3-bis [di (6-carboxylpyridine) Yl) amino] benzene, 1,3-bis [di (4-cyanopyridine-2-yl) amino ] Benzene, 1,3 bis [di (5 cyanopyridine-2-yl) amino] benzene, 1,3 bis [di (6 cyanopyridine-2-yl) amino] benzene,

In general formula (3), 2, 6 bis [(phenol) (pyridine-2-yl) amino] pyridine, 2, 6 bis [(3-methylphenol) (4-methylpyridine-2-yl ) Amino] pyridine, 2, 6-bis [(3-methylphenol) (6-methylpyridine-2-yl) amino] pyridine, 2,6bis [(4-methylphenol) (5-methyl) Pyridine 1-yl) amino] pyridine, 2, 6 bis [(3 —ethylphenyl) (4 ethylpyridine-2-yl) amino] pyridine, 2, 6 bis [(3-ethyl) (6 Ethylpyridine—2-yl) amino] pyridine, 2,6bis [(4-ethylpropyl) (5-ethylpyridine-2-yl) amino] pyridine, 2,6bis [(3-n-propylphenol) ) (4-N-propylpyridine-2-yl) amino] pyridine, 2,6bis [(3-n-propylphenol) (6-n-propylpyridine) 2-yl) amino] pyridine, 2,6-bis [(4-n-propylpropyl) (5-n-propylpyridine-2-yl) amino] pyridine, 2,6-bis [(3-isopropylphenol) ) (4-Isopropylpyridine-2-yl) amino] pyridine, 2,6bis [(3-Isopropylphenol) (6-isopropylpyridine-1-yl) amino] pyridine, 2,6bis [ (4-Isopropyl file) (5-Isopropylpyridine-2-yl) amino] pyridine, 2, 6 bis [(3-n-Butylphenol) (4-n-Butyryridine-2-yl) ) Amino] pyridine, 2, 6 bis [(3-n-butylphenol) (6-n-butylviridine-2-yl) amino] pyridine, 2,6 bis [(4-n-butylphenol) (5-n-butylpyridine-2-yl) amino] pyridine, 2,6bis [(3-isobutylphenol) (4-isobutyl Lysine-2-yl) amino] pyridine, 2,6bis [(3-isobutylphenyl) (6-isobutylpyridine-2-yl) amino] pyridine, 2,6bis [(4-isobutylphenol- ) (5-Isobutylpyridine-2-yl) amino] pyridine, 2, 6 bis [(3 — sec butylphenol) (4 sec butylpyridine-2-yl) amino] pyridine, 2, 6 bis [(3 sec Butylphenol) (6 sec butylpyridine 2-yl) amino] pyridine, 2, 6 bis [(4 sec butylphenol) (5 sec butylpyridine-2-yl) amino] pyridine, 2, 6 bis [(3— tert-butylphenyl) (4-tert-butylpyridine-2-yl) amino] pyridine, 2,6bis [(3-tert-butylphenol) (6-tert-butylpyridine-2-yl) amino ] Pyridine, 2, 6 bis [(4-tert-butylphenol) (5 —Tert-Butylpyridine— 2-yl) amino] pyridine, 2, 6 bis [(3-n-pentylphenol) (4- _n pentylviridine-2-yl) amino] pyridine, 2, 6 bis [(3— n-pentylphenol) (6— n-pentylviridine-2-yl) amino] pyridine, 2, 6 bis [(4- n-pentylphenol) (5- n-pentylpyridine-2) —Yl) amino] pyridine, 2, 6 bis [(3 isopentylphenol) (4 isopentylpyridine 2 ylamino)] pyridine, 2, 6 bis [(3-isopentylphenol) (6 —Isopentylpyrrolidine-2-yl) amino] pyridine, 2, 6bis [(4-Isopentylphenyl) (5-isopentylpyridin-2-yl) amino] pyridine, 2,6bis [(3-Neopentylphenol) (4-Neopentylpyridine-2-yl) amino] pyridine, 2, 6 Bis [(3-Neo Ntylphenol) (6-Neopentylviridine-2-yl) amino] pyridine, 2,6bis [(4-Neopentylphenol) (5-Neopentylpyridine-2-amino) amino] pyridine, 2 , 6 Bis [(3-n-hexylphenol) (4-n-hexylpyridine 1- 2-yl) amino] pyridine, 2, 6 bis [(3- n-hexylphenol) (6 — N-hexylpyridine 1-yl) amino] pyridine, 2,6bis [(4-n-hexylphenol) (5-n-hexylpyridine-2-yl) amino] pyridine, 2, 6 Bis [(3-Isohexylphenol) (4-Isohexylpyridine-2-yl) amino] pyridine, 2, 6 Bis [(3-Isohexylphenol) (6-Isohexene) Xylpyridin-2-yl) amino] pyridine, 2, 6 bis [(4-isohexylphenol) (5-isohexylpyridine-2-yl) amino] Pyridine, 2, 6bis [(3-n-octylphenol) (4-n-octylviridine-2-yl) amino] pyridine, 2,6bis [(3-n-octylphenol) (6— n-octylviridine-2-yl) amino] pyridine, 2,6bis [(4-n-octylphenyl) (5-n-octylviridine-2-yl) amino] pyridine, 2,6bis [(3 — N-decylphenol) (4— n-decylviridine-2-yl) amino] pyridine, 2, 6-bis [(3- n-decylphenyl) (6- n-decylviridine-2-yl) Amino] pyridine, 2,6bis [(4-n-decylphenyl) (5-n-decylviridine-2-yl) amino] pyridin, 2,6bis [(3-hydroxylphenyl) (4 Hydroxylpyridine 1-yl) amino] pyridine, 2, 6 bis [(3 Hydroxylphenol) (6-hydroxylpyridine 2- 2-y ) Amino] pyridine, 2, 6-bis [(4 - hydroxyl Hue - Le) (5 hydroxyl-2-I le) Amino] pyridine, 2, 6-bis [(3-Arukanoirufue - Le) (4 Arukanoi Rubilidine-2-yl) amino] pyridine, 2,6bis [(3 alkanoylphenol) (6-alkanoylpyridine-2-yl) amino] pyridine, 2,6bis [(4-alkanoylphenol) ) (5 alkanoylpyridine-2-yl) amino] pyridine, 2, 6 bis [(3-carbamoylphenol) (4-force rubamoylpyridine-2-yl) amino] pyridine, 2, 6 Bis [(3 —Strength Lumamoyl File) (6—Strength Lumamoyl Viridine—2-yl) amino] pyridine, 2, 6 -Bis [(4-Strength Lumamoyl File) (5 T ) Amino] pyridine, 2, 6 bis [(3-carboxyl phenol) (4-carboxyl pyridine-2-yl) amino] pyridine, 2, 6 bis [(3-carboxyl phenol) (6— Carboxylpyridine —2-yl) amino] pyridine, 2, 6 bis [(4-carboxyl Ethyl) (5-carboxyrubiridin-2-yl) amino] pyridine, 2,6bis [(3 cyanophyl) (4 cyanobilysine-2-yl) amino] pyridine, 2,6bis [( 3-Cyanophyl) (6 Cyanopyridine-2-yl) amino] pyridine, 2, 6 bis [(4-Cyanofenol) (5-Cyanofyridine-2-yl) amino] pyridine,

In general formula (4), 1,3 bis [(phenol) (pyridine-2-yl) amino] benzene, 1,3 bis [(3-methylphenol) (4-methylpyridine-2-y L) amino] pyridine, 1,3-bis [(3-methylphenol) (6-methylpyridine-2-yl) amino] pyridine, 1,3bis [(4-methylphenol) (5-methyl) Pyridine 1-yl) amino] pyridine, 1,3 bis [(3-ethyl) phenyl (4-ethylpyridine-2-yl) amino] pyridine, 1,3 bis [(3-ethyl) (6) Ethylpyridine—2-yl) amino] pyridine, 1,3 bis [(4-ethylpropyl) (5-ethylpyridine-2-yl) amino] pyridine, 1,3 bis [(3-n-propylphenol) ) (4-N-propylpyridine-2-yl) amino] pyridine, 1,3 bis [(3-n-propylphenol) (6-n-propylpyridine) 2-yl) amino] pyridine, 1,3-bis [(4-npropylpropyl) (5-npropylpyridine-2-yl) amino] pyridine, 1,3-bis [(3-isopropylphenol) ) (4-Isopropylpyridine-2-yl) amino] pyridine, 1,3bis [(3-Isopropylphenol) (6-isopropylpyridine-1-yl) amino] pyridine, 1,3bis [ (4-Isopropyl file) (5-Isopropylpyridine-2-yl) amino] pyridine, 1,3 bis [(3-n-Butylphenol) (4-n-Butyryridine-2-yl) ) Amino] pyridine, 1,3 bis [(3— n-butylphenol) (6— n —Butylviridine— 2-yl) amino] pyridine, 1,3 bis [(4— n-butylphenol) (

5— n-butylpyridine— 2-yl) amino] pyridine, 1,3 bis [(3-isobutylphenol) (4-isobutylpyridine-2-yl) amino] pyridine, 1,3 bis [( 3-isobutylphenyl) (6-isobutylpyridine-2-yl) amino] pyridine, 1,3-bis [(4-isobutylphenol) (5-isobutylpyridine-2-yl) amino] pyridine, 1, 3 Bis [(3 — sec Butyl Phenol) (4 sec Butyl Pyridine-2-yl) amino] pyridine, 1, 3 Bis [(3 sec Butyl Phenol) (6 sec Butyl Pyridine 2 Fil) amino] Pyridine , 1,3 bis [(4 sec butylphenol) (5-sec butylpyridine 2-ylamino) pyridine, 1,3 bis [(3-tert butylphenol) (4-tert-butylpyridine —2— Yl) amino] pyridine, 1,3 bis [(3-tert-butylphenol) (6-tert-butylpropyl) N—2-yl) amino] pyridine, 1,3 bis [(4-tert-butylphenol) (5 —tert-butylpyridine-2-yl) amino] pyridine, 1,3 bis [(3— n- Penchirufu E - Le) _{(4-n-pentylbicyclo} lysine - 2-I le) Amino] pyridine, 1, 3-bis [(3- n- Penchirufue - Le) (6- n- pentylbicyclo lysine - 2-I le) Amino] pyridine, 1,3 bis [(4-n-pentylphenol) (5-n-pentylviridine-2-yl) amino] pyridine, 1,3bis [(3 isopentylphenol) (4 Isopentylviridine 2-yl) amino] pyridine, 1,3 bis [(3-isopentylphenyl) (6-isopentylviridine-2-yl) amino] pyridine, 1,3 bis [(4-iso Pentylphenol) (5-isopentylpyridin-2-yl) amino] pyridine, 1,3bis [(3-neopentylphenol) (4 Neopentyl Nchirupirijin - 2-I le) Amino] pyridine, 1, 3-bis [(3-Neopenchirufue - Le) (

6-Neopentylviridine-2-yl) amino] pyridine, 1,3bis [(4-Neopentylphenol) (5-Neopentylviridine-2-yl) amino] pyridine, 1,3bis [( 3—n—Hexylphenol) (4—n—Hexylpyridine—2-yl) amino] pyridine, 1,3bis [(3—n—hexylphenol) (6—n—hexyl) 1-yl) amino] pyridine

, 1,3 bis [(4-n-hexylphenol) (5-n-hexylpyridine-2-yl) amino] pyridine, 1,3 bis [(3-isohexylphenol) ( 4-Isohexylpyridine-2-yl) amino] pyridine, 1,3 bis [(3-Isohexylphenol) (6-isohexylpyridine-2-yl) amino] pyridine, 1, 3 Bis [(4-Isohexylphenol) (5-Isohexyl) Xylpyridine-2-yl) amino] pyridine, 1,3bis [(3-n-octylphenol) (4-n-octylviridine-2-yl) amino] pyridine, 1,3bis [(3— n-octylphenol) (6-n-octylviridine-2-yl) amino] pyridine, 1,3 bis [(4-n-octylphenyl) (5-n-octylviridine-2-yl) amino ] Pyridine, 1,3bis [(3-n-decylphenyl) (4-n-decylviridine-2-yl) amino] pyridine, 1,3-bis [(3-n-decylphenol) (6 — N-decylviridine—2-yl) amino] pyridine, 1,3 bis [(4-n-decylvinyl) (5-n-decylviridine-2-yl) amino] pyridin, 1,3 bis [ (3 hydroxyl file) (4 hydroxyl pyridine 1- 2-yl) amino] pyridine, 1, 3 bis [(3 hydroxyl file) 6 Hydroxylpyridine 1-yl) amino] pyridine, 1,3 bis [(4 hydroxylphenol) (5 Hydroxylpyridine —2-yl) amino] pyridine, 1,3 bis [(3 alkanoylphenol) (4 Alkanorubiridine—2-yl) amino] pyridine, 1,3 bis [(3 Alkanoylphenol) (6-Alkanoylpyridine-1-yl) amino] pyridine, 1,3 bis [(4— Alkanoylphenol) (5 alkanoylpyridine-2-yl) amino] pyridine, 1,3 bis [(3-carbamoylphenol) (4-force rubamoylviridine-2-yl) amino] pyridine, 1, 3 Bis [(3 —Strengthen rubermoyl file) (6—Strength rubermoyl pyridine—2-yl) amino] pyridine, 1, 3-bis [(4 -Strength ruber moyl file) (5-strength ruber moyl ferridine) 2-yl) amino] pyridine, 1, 3 bis [(3-carol Xylphenyl) (4-carboxylpyridine-2-yl) amino] pyridine, 1,3bis [(3-carboxylphenol) (6-carboxylpyridine-2-yl) amino] pyridine, 1, 3 Bis [(4-carboxylphenol) (5-carboxyrubiridin-2-yl) amino] pyridine, 1,3 bis [(3 cyanol) (4 cyanobilysine 2-yl) amino] pyridine, 1,3 bis [(3 cyanophyl) (6-cyanopyridine-2-yl) amino] pyridine, 1,3 bis [(4-cyanophyl) (5-cyanopyridine-2-yl) amino] pyridine, Etc. Among these, 2,6 bis [di (pyridine-2-yl) amino] pyridine, 2,6 bis [di (5-methylpyridine-2-yl) amino] pyridin, 1,3 bis [ Di (pyridine-2-yl) amino] benzene, 1,3 bis [di (5-methylpyridine-1-2-yl) amino] benzene, 2,6 bis [(phenol) (pyridine-2-2 ) Amino] pyridine, 2, 6bis [(4-methylphenol) (5-methylpyridine-2-yl) amino] pi Lysine, 1,3-bis [(phenyl) (pyridine-2-yl) amino] benzene, and 1,3-bis [(4 methylphenol) (5-methylpyridine-2-yl) amino] benzene are preferred. ! /

[0030] The compound of the present invention represented by the general formula (I) can be produced, for example, as follows. That is, the general formula (Π):

[0031] [Chemical 10]

(In the formula, R ¹ represents a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubamoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoyl group having 1 to 10 carbon atoms, and V represents nitrogen. Dihalogeno monocyclic compounds represented by the general formula (ΠΙ):

[0033] [Chemical 11]

(Wherein R ² and R ³ are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubamoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 may be the same or different, and W may be the same or different. W represents a nitrogen atom or a carbon atom.) The target compound can be obtained by reacting in the presence of a catalyst containing the compound and a base.

In the dihalogeno monocyclic compound represented by the general formula (式), examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0036] As a specific example of the dihalogeno monocyclic compound represented by the general formula (Π), V is a nitrogen atom. In this case, 2, 6 dihalogenopyridine compound, and in the case where V is a carbon atom, 1,3-dihalogenobenzene compound can be mentioned.

Specific examples of 2,6 dihalogenopyridine compounds include 2,6 difluoropyridin, 2,6 dicyclopyridine, 2,6 dibromopyridine, 2,6 jodopyridine, 2,6-dichloro-3 methylpyridine, 2 , 6 dichloro-4 methylpyridine, 2,6 dichloro-5 methylpyridine, 2,6 dichloro-3 ethylpyridine, 2,6 dichloro-4-ethylpyridine, 2,6 dichloro-5 ethylpyridine, 2,6 dichloro-3 isopropylpyridine, 2,6 dichloro-4 Isopropylpyridine, 2,6 dichloro-5 isopropylpyridine, 2,6 dichloro-1-3-n-propylpyridine, 2,6 dichloro-4-n-propinoleviridine, 2,6 dichloro-5-n-propinoleviridine, 2, 6 Dichloro-3—n-Butylpyridine, 2, 6 Dichloro-4 n-Butylpyridine, 2, 6 Dichloro-5-n— Tylpyridine, 2, 6 dichloro-3 sec butylpyridine, 2, 6 dichloro-4 sec butylpyridine, 2, 6 dichloro-5 sec butylpyridine, 2, 6 dichloro-3-tert-butylpyridine, 2,6-dichloro-4-tert-butylpyridine, 2 , 6 Dichloromethane — 5-tert-butylpyridine, 2,6-dichloro-3-n-pentylpyridine, 2,6-dichloro 4-n-pentylpyridine, 2,6-dichloro-1-5-n-pentylpyridine, 2, 6 — Dichloro-3 isopentylpyridine, 2, 6 dichloro-4 isopentylpyridine, 2, 6-dichloro-5 isopentylpyridine, 2, 6 dichloro-3 neopentylpyridine, 2,6 dichloro 1 4-neopentyl pyridine, 2, 6 dichloro 1 5-Neopentylpyridine, 2,6-dichloro-3-n-hexylolepyridine, 2,6-dichloro-4-n-hexylpyridine, 2,6 di Rollo 5— n-hexenorepyridine, 2, 6 dichloro-3 isohexylene pyridine, 2, 6 dichloro-4 isohexenorepyridine, 2, 6 dichloro-5 isohexyl pyridine, 2, 6 dichloro 1 3-n— Octylviridine, 2,6 dichloro 4-n-octinorepyridine, 2, 6 dichloro-5-n-octinorepyridine, 2, 6 dichloro 3-n-decinorepyridine, 2, 6 dichloro 4-n-decinorepyridine, 2, 6 Examples include dichloro-5-n-decinorepyridine, 2,6 dichloro-4-cyanopyridine, 2,6 dichloro-4 selenium norpyridine pyridine, 2,6 dichloro-4-hydroxypyridine, and the like. Among these, 2,6 diclomental pyridine and 2,6 dibromopyridine are preferred because they are easily available and economical. Preferably used.

[0037] Specific examples of 1,3 dihalogenobenzene compounds include 1,3 difluorobenzene, 1,3 dichlorobenzene, 1,3 dibromobenzene, 1,3 jodobenzene, 1,3—dib-mouthed —Methylolebenzene, 1,3 Jib mouth mode 2 Ethenolebenzene, 1,3 Jib mouth mode 2—n—Hexinolebenzene, 1,3 Jib port mode 2—n—Octinolebenzene, 1, 3 —Jib port Mo 2— n-decylbenzene, 1, 3 dib-mouthed MO 4-methylbenzene, 1, 3 Jib-mouthed Mo 4-ethylenobenzene, 1, 3 Jib-mouthed Mo 4—n—hexynolebenzene, 1, 3 Jib mouth mode 4 n—octylbenzene, 1, 3 Jib port mode 4 n decylbenzene, 1, 3 Jib mode mode 5—Methinorebenzene, 1, 3 Jib mode mode 5 Ethinorebenzene, 1, 3 Jib mode mode 5—n— Hexinorebenzene, 1, 3 Jib mouth mor 5-n-octinolebenzene, 1, 3 di 5-n-decylbenzene, 1,3 dichloro 5-methylbenzene, 1,3 dichloro-5-ethylbenzene, 1,3 dichloro 5-5-n-hexenolebenzene, 1,3 dichloro 5-5-n— Octylbenzene, 1,3-dichloro-1,5-n-decylbenzene, 1,3 dib-mouthed mo 5 hydroxybenzene, 1,3 dib-headed mo 5 alkanoylbenzene, 1,3 dib-mouthed mo 5—powered rubermoylbenzene, 1, 3 Examples include jib mouth moe 5 carboxybenzene and 1,3 jib mouth moe 5 cyanobenzene. Of these, 1,3 dibromobenzene and 1,3 dichroic benzene are preferably used from the viewpoint of availability and economy.

[0038] As specific examples of the amine compound represented by the general formula (III), when W is a nitrogen atom, bis (pyridine-1-yl) amine, bis (4-methylpyridine 2-yl) amine, bis (5-methylpyrrolidine-2-yl) amine, bis (6-methylpyridine-2-yl) amine, bis (4-ethylpyridine-2-yl) amamine, bis (5- Ethylpyridine 2-yl) amine, bis (6-ethylpyridine-2-yl) amine, bis (4-n-propylpyridine-2-yl) amine, bis (5-n-propylpyridine-2-yl) amine Bis (6-n-propylpyridin-2-yl) amine, bis (4-isopropylpyridine-2-yl) amine, bis (5-isopropylpyridine-2-yl) amine, bis (6 —Isopropylpyridine-2-yl) amine, bis (4-n-butyl) Lysine - 2-I le) Amin, bis (5-n-butylpyridine - 2 I le) Amin, bis (6- n-butylpyridine one 2-I le) Amin, bis (4-Isobuchirupiri Gin-2-yl) amine, bis (5-isobutylpyridine-2-yl) amine, bis (6-isobutynolepyridine-2-inole) amine, bis (4-sec-butynolepyridine-2-inole) Amines, bis (5 sec butynolepyridine 2-yl) amines, bis (6 sec butynolepyridine 2-yl) amines, bis (4-tert-butylpyridine-2-yl) amines, bis (5-tert) —Butylpyridine 2-yl) amine, bis (6-tert-butylpyridine-2-yl) amine, bis (4-n-pentylviridine-2-yl) amine, bis (5-n-pentylviridine-2-yl) amine Bis (6-n-pentylviridine-2-yl) amine, bis (4-isopentylpyridine-2-yl) amine, bis (5-isopentylviridine-2-yl) amine, bis (6-iso) Pentylviridine 2 yl) amine, Sus (4 neopentylpyridine 2-yl) amine, bis (5 neopentylpyridine-2-yl) amine, bis (6 neopentylpyridin-2-yl) amamine, bis (4-n-hexylpyridine-2) —Yl) amine, bis (5-n-hexylpyridine 2-yl) amine, bis (6-n-hexylpyridine 2-yl) amine, bis (4-isohexylpyridine-2-yl) Amines, bis (5-isohexylpyridine-2-yl) amines, bis (6-isohexylpyridine-2-yl) amines, bis (4-n-octylviridine-2-yl) amines, Bis (5-n-octylviridine-2-yl) amine, bis (6-n-octylviridine-2-yl) amine, bis (4-n-decylviridine-2-yl) amine, bis (5- n-decylviridine-2-yl) amine, bis (6-n-decyl) Lysine-2-yl) amine, bis (4-hydroxylpyridine-2-yl) amine, bis (5-hydroxypyridine-2-yl) amine, bis (6-hydroxylpyridine-2-yl) amine, Bis (4 alkanoylpyridine 1-2 yl) amine, bis (5 alkanoyl pyridine 1-2 yl) amine, bis (6 alkanol pyridine-2-yl) amamine, bis (4-strength rubamoylbi) Lysine—2-yl) amine, bis (5-force rubermoyl bilysine—2-yl) amine, bis (6-force rubermoyl bilysin—2-yl) amine, bis (4-carboxylpyridine—— Yl) amine, bis (5-carboxylpyridine-2-yl) amine, bis (6-carboxylpyridine-2-yl) amine, bis (4-cyanopyridine-2-yl) amamine, bis (5-cyanopyridine) Gin 2 Amin and bis (6 Shianopirijin 2 I le) Ru Amin, and the like. Of these, bis (pyridine-2-yl) amine and bis (5-methylpyridine 2-yl) amine are preferably used from the viewpoint of availability and economy. In addition, specific examples of the amine compound represented by the general formula (III) include, when W is a carbon atom, (phenyl) (pyridine 2-yl) amine, (3 methylphenol) (4 Methylpyridine-2-yl) amine, (3-Methylphenol) (6-Methylpyridine-2-yl) amine, (4 Methylphenol) (5 Methylpyridine-2-yl) amine, (3 Ethylphenyl) (4 ethylpyridine 2-yl) amine, (3 ethylphenol) (6 ethylpyridine-2-yl) amine, (4 ethylphenyl) (5 ethylpyridine-2-yl) amamine, (3— n — Propylphenol) (4-n-propylpyridine-2-yl) amine, (3-n-propylphenol) (6-n-propylpyridine-2-yl) amine, (4-n-propylphenol) -Le) (5-n-propylpyridine 1-yl) amine, (3-iso) (Ro-propyl) (4-isopropylpropylidine-2-yl) amine, (3-isopropylphenyl) (6-isopropylpyridine-2-yl) amine, (4-isopropylphenyl) (5-isopropylpyridine) 1-yl) amine, (3 n-butylphenol) (4 n-butylpyridine-2-yl) amine, (3-n-butylpyridine) (6 n-butylpyridine-2-yl) amine, ( 4 n-Butylphenol) (5 n-Butylpyridine-2-yl) amine, (3 Isobutylphenol) (4 Isobutylpyridine-2-ylamine), (3 Isobutylphenol) (6 Isobutylpyridine-2-yl) ) Amine, (4 isobutylphenol) (5 isobutylpyridine-2-ylamine), (3-sec butylphenol) (4 sec butylpyridine-2-yl) amine, (3 sec butylphenol) (6 sec Butylpyridine 2-yl) amine, (4 sec butylphenol) (5 sec butylpyridine 2-ylamine), (3-tert-butylphenol) (4-tert-butylpyridine-2-ylamine), (3-tert-butylphenol) (6-tert-butylpyridine 2-yl) amine, (4-tert-butylphenol) (5-tert-butylpyridine 2-amine), (3-n-pentylphenol) (4-n-pentylpyridine) -2-yl) amine, (3-n-pentylphenol) (6-n-pentylpyridine-2-yl) ammine, (4-n-pentylphenol) (5-n-pentylpyridine-2- Yl) amine, (3-isopentylphenyl) (4 isopentylpyridine 2 yl) amine, (3 isopentyl phthalate) (6 isopentyl pyridine 2 yl) amine, (4 isopentyl phthalate) ) (5--sopentyl pyridine 2 yl) amine, (3 neope Chirufue - Le) (4 neopentyl Rubirijin 2 I le) Amin, (3 Neopenchirufue - Le) (6 neopentyl ruby lysine —2—yl) amine, (4-neopentylphenol) (5-neopentylpyridine-2—yl) amine, (3-n-hexylphenol) (4-n-hexylpyridine— 2-yl) amine, (3-n-hexylphenol) (6-n-hexylpyridine-2-yl) amine, (4 n xylphenyl) (5-n-hexylpyridine) —Yl) amine, (3-isohexylphenol) (4-isohexylpyridine-2-yl) amine, (3-isohexylphenol) (6-isohexylpyridine-2-yl) ) Amine, (4-Isohexylphenol) (5-Isohexylpyridine 2-yl) amine, (3-n-octylphenol) (4-n-octylpyridine 2-yl) amine, (3- n- Okuchirufue - Le) (6- n- O lipped ruby lysine-2 I-le) Amin, _(4-n Okuchirufue - Le) (5-n- O click 1-yl) amine, (3-n-decylphenyl) (4-n-decylviridine-2-yl) amine, (3-n-decylphenyl) (6-n-decylviridine-2) —Yl) amine, (4-n-decylphenyl) (5-n—decylviridine-2-yl) amine, (3-hydroxylphenol) (4-hydroxylpyridine-2-yl) amine, ( 3 Hydroxylphenol) (6 Hydroxylpyridine 2-yl) amine, (4 Hydroxylphenol) (5-hydroxylpyridine 2-yl) amine, (3-Alkanophenyl) (4 Alkanoylpyridine) 1 2-yl) amine, (3 alkanoyl pyridine) (6 alkanoyl pyridine 2 yl) amine, (4 alkanoyl pyridine) (5 alkanoyl pyridine 2 yl) amamine, (3—strength rubamoyl phe -Le) (4 power Luba (Ilpyridine 2 yl) amine, (3—Strengthened ruber moyl file) (6—Strengthened ruber molybidine 2 mil), (4—Strength ruber moyl ferrule) (5—Strength rubamoyl ferridine —2—yl) ammine, (3-carboxyl file) (4-carboxylpyridine-2-yl) amine, (3-carboxyl file) (6-carboxylpyridine-2-yl) amine, (4-carboxyl file) (5-carboxylpyridine-2-yl) amin, (3-cyanol) (4-cyanopyridine-2-yl) amin, (3-cyanophyl) (6cyanopyridine-2-yl) amamine, (4cyanophyl) -L) (5-cyanopyrido-2-yl) amine and the like. Of these, (phenyl) (pyridine-2-yl) amine and (4 methylphenol) (5-methylpyridine-2-yl) amine are preferably used from the viewpoint of availability and economy.

These amine compounds used in the present invention can be obtained from commercially available products or appropriately synthesized. Any of the above may be used. As a method for synthesizing these amine compounds, for example,

And a method of reacting 2-aminoviridine having a corresponding substituent with 2-promopyridine having a corresponding substituent or bromobenzene having a corresponding substituent by heating and refluxing in a nitrogen stream in the presence of a copper compound. (See Chem. Lett., 1311 (1990)).

[0041] The amount of the amine compound used is preferably 2.0 to 3.0 moles, more preferably 2.0 to 2.5 moles per mole of the dihalogeno monocyclic compound. When the amount of the amine compound used is less than 2.0 mol, the reaction is difficult to proceed and the reaction may be difficult to complete. Also, if the amount of amine compound used exceeds 3.0 moles, there is a risk that the effect will not be commensurate with the amount used and it will not be economical.

[0042] The palladium compound as a catalyst used in the reaction for obtaining the compound of the present invention is not particularly limited, but, for example, sodium hexalopalladium (IV) acid sodium tetrahydrate. , Tetravalent palladium compounds such as potassium hexapalladium (IV); palladium chloride (Π), palladium bromide (Π), palladium acetate (Π), radium acetyl acetylacetonate (II), dichlorobis (benzonitrinore ) Palladium (Π), dichlorobis (acetonitryl) palladium (Π), dichlorobis (triphenylphosphine) palladium (Π), dichlorobis (triolphosphine) palladium (Π), dichlorotetraamminepalladium (Π), di Divalent, such as black and white (Cycloocta 1, 5 Gen) palladium (Π), palladium trifluoroacetate (II) Radium compounds: Tris (dibenzylideneacetone) dipalladium (0), tris (dibenzylideneacetone) dipalladium chromatoform complex (0), tetravalent (triphenylphosphine) palladium (0), etc. Is mentioned. Of these, a zero-valent palladium compound is preferable from the viewpoint of high reaction activity. Among these, tris (dibenzylideneacetone) dipalladium (0) has the highest reaction activity and is preferably used. These palladium compounds may be used alone or in combination of two or more.

[0043] The amount of the palladium compound used is preferably 0.0001 to 0.2 monole in terms of palladium conversion per mole of dino or oral genomonocyclic compound S, preferably 0.00002 to 0.05 monole. Something is better than power ^. If the amount of the radium compound used is less than 0.0001 mol, the reaction may proceed. If the amount of noradium compound used exceeds 0.2 mol, There is a risk that it will not be economical because there is no effect corresponding to the amount used.

[0044] The phosphine compound used as the catalyst for the reaction for obtaining the compound of the present invention is not particularly limited. For example, 2, 2'-bis (diphenylphosphino) 1 1, 1, -binaphthyl, 1,1, -bis (diphenylphosphino) fecene, N, N, -dimethyl — 1— [, 2 bis (diphosphosphino) ferrocer], 9, 9 dimethyl-4,5 — Phosphinic compounds having chelating ability as bidentate ligands such as bis (diphenylphosphino) xanthene. Of these, 2,2′-bis (diphenylphosphino) -1,1, -binaphthyl and 9,9 dimethyl-4,5bis (diphenylphosphino) xanthene are preferably used from the viewpoint of high reaction activity. These phosphine compounds can be used alone or in combination of two or more.

[0045] The amount of the phosphine compound used is preferably 0.1 to 10 moles, more preferably 0.5 to 5 moles per mole of the palladium compound. If the amount of the phosphine compound used is less than 0.1 mol, the reaction may proceed. Also, if the amount of phosphine compound used exceeds 10 moles, there is a risk that the effect will not be commensurate with the amount used and that it will not be economical.

[0046] In the present invention, the palladium compound and the phosphine compound may be individually added to the reaction system, or those prepared in the form of a complex in advance may be added.

[0047] The base used in the reaction for obtaining the compound of the present invention is not particularly limited, and examples thereof include sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, and lithium-tert. Examples include alkali metal alkoxides such as —butoxide, sodium-tert butoxide and potassium-tert butoxide. These bases may be used alone or in combination of two or more. Further, each of them may be directly added to the reaction system, or one prepared from an alkali metal, an alkali metal hydride, a hydroxide or an alkali metal, and a corresponding alcohol may be added.

[0048] The amount of the base used is preferably 2 to 30 mol, more preferably 2 to 10 mol, relative to 1 mol of the dihalogeno monocyclic compound. If the amount of base used is less than 2 moles, the yield may decrease. If the amount of base used exceeds 30 moles, it will be commensurate with the amount used. There is a risk that it will not be effective and economical.

[0049] The solvent used in the reaction for obtaining the compound of the present invention is not particularly limited as long as it is an inert solvent for the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene and the like. Solvents: ether solvents such as jetyl ether, tetrahydrofuran, dioxane, etc .; acetonitrile, dimethylformamide, dimethyl sulfoxide, hexamethyl phosphotriamide and the like. Of these, aromatic hydrocarbon solvents such as benzene, toluene and xylene are preferably used because the solvent can be easily recycled.

[0050] The amount of the solvent used is not particularly limited, but from the viewpoint of facilitating the reaction and obtaining an effect sufficient for the amount of use, the dihalogeno monocyclization represented by the general formula (Π) It is preferable that it is 500 to 10000 parts by weight per 100 parts by weight of the compound! /.

The reaction temperature is not particularly limited, but is preferably 20 to 250 ° C, more preferably 50 to 150 ° C. If the reaction temperature is lower than 20 ° C, the reaction may take a long time. On the other hand, when the reaction temperature is higher than 250 ° C, side reactions may occur and the yield may decrease. Since the reaction time varies depending on the reaction temperature, it cannot be generally stated, but it is usually 1 to 20 hours.

[0051] The compound of the present invention obtained by force can be isolated by a conventional method, after filtration and washing to remove the catalyst and the like, followed by drying.

[0052] In addition, a catalyst and a base comprising a dihalogeno monocyclic compound represented by the general formula (ァ) and an amine compound represented by the general formula (ΠΙ), a noradium compound and a phosphinic compound The production method of the present invention, wherein the compound represented by the general formula (I) is obtained by reacting in the presence of the compound, also obtains a compound having a structure similar to that of the compound represented by the general formula (I). It can use suitably also as a manufacturing method.

Specifically, instead of the dihalogeno monocyclic compound represented by the general formula (Π), the general formula (

IV):

[0054] [Chemical Formula 12] zz ^Ar \ _z (IV) [0055] (wherein Ar represents a monocyclic 6-membered aromatic ring group which may have a substituent, and Z represents a halogen atom) Show. And a dihalogeno compound represented by the general formula (V):

[0056] [Chemical 13]

(In the formula, R ⁴ and R ⁵ are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubamoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to In the same manner as in the production method of the present invention except that a diphenylamine compound represented by formula (VI) is used. ):

[0058] [Chemical 14]

R ^{4 4}

(In the formula, Ar represents a monocyclic 6-membered aromatic ring group which may have a substituent. R ⁴ and R ^{5 each} independently represents a hydrogen atom, a hydroxyl group, or a carboxyl group. , A cyano group, a strong rubermoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoyl group having 1 to 10 carbon atoms, which may be the same or different.) A high yield of about 90% can be obtained with respect to the dihalogeno compound used.

The invention's effect

[0060] According to the present invention, there is provided a low molecular weight organic compound having a light-electron conversion function and capable of forming a thermally stable amorphous film by itself, and a method for producing the same. Can do.

BEST MODE FOR CARRYING OUT THE INVENTION

[0061] Hereinafter, the present invention will be specifically described by way of examples. However, the present invention is not limited to these examples!

[0062] Example 1

2, 6 Bis [di (pyridine-2-yl) amino] pyridine [Formula (1), Ι ^ 〜Κ ³ = Η]

A 300 mL four-necked flask equipped with a condenser, thermometer and stirrer was charged with 5.69 g (24 mmol) of 2, 6-dibromopyridine and 8.22 g (48 mmol) of bis (pyridine-2-yl) amine. ), Tris (dibenzylideneacetone) dipalladium (0) 1.10 g (l. 2 mmol), 2, 2, —bis (diphenylphosphino) — 1, 1, -binaphthyl 2.24 g (3.6 mmol) Sodium-tert-butoxide 6.92 g (72 millimonoles) and tonorene 240 mL were charged. Next, the temperature was raised to 100 ° C. under a nitrogen atmosphere, and the reaction was further stirred for 8 hours at the same temperature. Thereafter, the reaction solution was cooled to room temperature, and the precipitate was collected by filtration and dried to obtain 6.20 g of 2,6bis [di (pyridin-2-yl) amino] pyridine of the present invention. The yield of 2,6bis [di (pyridine-2-yl) amino] pyridine obtained was 62% based on the 2,6 dibromopyridine used.

The compound strength obtained was confirmed to be 2, 6 bis [di (pyridine-2-yl) amino] pyridine by the following analysis results.

Molecular weight (mass spectrometry by atmospheric pressure ionization method): 417

IR (KBr): 1583, 1566, 1466, 1447, 1426, 1348, 1320, 1304, 1274, 12 62, 776cm " ¹

[0063] Evaluation

The 2, 6 bis [di (pyridine-2-yl) amino] pyridine obtained in Example 1 was evaluated for light emission characteristics and thermal stability.

(Luminescent characteristics)

The 2,6-bis [di (pyridine-2-yl) amino] pyridine obtained in Example 1 was dissolved in 1-methyl-2-pyrrolidone, and a measurement sample (concentration: 1 X 10 " ³ g / L) was obtained. Prepare and fluorescence spectroscopic light The emission wavelength was measured using a spectrophotometer (Hitachi Ltd., trade name F-2500). As a result, it was confirmed that 2,6-bis [di (pyridine-2-yl) amino] pyridine obtained in Example 1 had a light emitting function. The fluorescence wavelength was 385 nm. Therefore, there is a high possibility that 2,6-bis [di (pyridine-2-yl) amino] pyridine obtained in Example 1 can be suitably used as a material for a light emitting layer in, for example, an EL device. That's right.

[0064] (Thermal stability)

The thermal decomposition temperature of 2,6-bis [di (pyridine-1-yl) amino] pyridine obtained in Example 1 was measured by differential thermal analysis, and glass transfer was further performed by differential scanning calorimetry. The temperature was measured.

Differential thermal analysis was performed by weighing 2,6-bis [di (pyridine-2-yl) amino] pyridine lmg obtained in Example 1 at room temperature at a temperature increase rate of 10 ° CZ in a nitrogen atmosphere. The temperature was raised to 500 ° C. As a result, the thermal decomposition temperature was found to be 255 ° C.

Differential scanning calorimetry was performed by weighing 2,6-bis [di (pyridin-2-yl) amino] pyridine lOmg obtained in Example 1 at room temperature at a heating rate of 10 ° CZ in a nitrogen atmosphere. To 200 ° C. Next, after cooling from 200 ° C to room temperature at a temperature decrease rate of 10 ° CZ, the temperature was increased from room temperature to 200 ° C at a temperature increase rate of 10 ° CZ again. As a result, the glass transition temperature was found to be 53 ° C. In addition, during this repeated measurement, no exothermic peak due to crystallization from amorphous was observed.

From these facts, 2,6-bis [di (pyridine-1-yl) amino] pyridine obtained in Example 1 is thermally stable at a thermal decomposition temperature of 255 ° C. Thus, it can be easily formed, and since it does not have a crystallization temperature, it can be seen that the formed amorphous film has excellent heat resistance.

[0065] Example 2

Preparation of 2, 6-bis [di (5-methylpyridine-2-yl) amino] pyridine [general formula (1), Ι ^ = Η, R ^{2 to} R ³ = 5-methyl]

In Example 1, bis (5-methylpyridine-2-yl) amine 9.55 g (48 mmol) was used instead of bis (pyridine-2-yl) amine 8.22 g (48 mmol). Implemented In the same manner as in Example 1, 6.58 g of 2,6-bis [di (5methylpyridine 2-yl) amino] pyridin of the present invention was obtained. The yield of 2,6bis [di (5-methylpyridine-2-yl) amino] pyridin obtained was 58% based on 2,6 dibromopyridine used.

It was confirmed by the following analytical results that the obtained compound strength was 2,6 bis [di (5-methylpyridine-2-yl) amino] pyridine.

Molecular weight (mass spectrometry by atmospheric pressure ionization method): 473

IR (KBr): 3029, 2996, 1596, 1579, 1479, 1454, 1413, 1384, 1191, 10 30, 788, 712cm " ¹

Evaluation

The 2,6-bis [di (5methylpyridine 2-yl) amino] pyridine obtained in Example 2 was evaluated for luminescent properties and thermal stability.

(Luminescent characteristics)

In the same manner as in Example 1, the emission wavelength was measured using a fluorescence spectrophotometer. As a result, it was confirmed that 2,6-bis [di (5-methylpyridine-2-yl) amino] pyridine obtained in Example 2 had a light emitting function. The fluorescence wavelength was 391 nm. Therefore, 2,6 bis [di (5-methylpyridine-2-yl) amino] pyridin obtained in Example 2 can be suitably used as a material for a light emitting layer in, for example, an EL device. It turns out that the possibility is high.

(Thermal stability)

The measurement was performed in the same manner as in Example 1.

Differential thermal analysis showed that the thermal decomposition temperature was 261 ° C.

Differential scanning calorimetry showed that the glass transition temperature was 49 ° C. Further, during this repeated measurement, no exothermic peak due to crystallization from amorphous was observed. Therefore, the 2, 6 bis [di (5 methylpyridine-2-yl) obtained in Example 2 was used. ) Amino] pyridine has a thermal decomposition temperature of 261 ° C and is thermally stable, so it can be easily formed by vapor deposition and the like, and since it does not have a crystallization temperature, It turns out that it has the outstanding heat resistance. [0067] Example 3

1, 3 Bis [di (pyridine-2-yl) amino] benzene [Formula (2), Ι ^ 〜Κ ³ = Η]

To a 300 mL four-necked flask equipped with a condenser, thermometer, and stirrer, was added 1.66 g (24 mmol) of 1,3-dibromobenzene, 8.22 g (48 mmol) of bis (pyridine-2-yl) amine. ), Tris (dibenzylideneacetone) ninoradium (0) 1.10 g (l. 2 mmol), 2,2, -bis (diphenylphosphino) — 1, 1, -binaphthyl 2.24 g (3.6 mmol) Sodium-tert butoxide 6.92 g (72 mmol) and 240 mL toluene were charged. Next, the temperature was raised to 100 ° C under a nitrogen atmosphere, and the reaction was further stirred for 8 hours at the same temperature. Thereafter, the reaction solution was cooled to room temperature, and the precipitate was filtered and dried to obtain 5.55 g of 1,3 bis [di (pyridine-2-yl) amino] benzene of the present invention. The yield of the obtained 1,3 bis [di (pyridine-2-yl) amino] benzene was 56% based on 1,3-dibromobenzene used.

It was confirmed by the following analytical results that the obtained compound strength was 1,3 bis [di (pyridine-2-yl) amino] benzene.

Molecular weight (mass spectrometry by atmospheric pressure ionization method): 416

IR (KBr): 1583, 1566, 1494, 1466, 1447, 1426, 1350, 1320, 1304, 12 61, 1157, 778cm " ¹

[0068] Evaluation

The 1,3-bis [di (pyridine-2-yl) amino] benzene obtained in Example 3 was evaluated for luminescent properties and thermal stability.

(Luminescent characteristics)

Prepare a measurement sample (concentration: 1 X 10 " ³ g / L) by dissolving the 1,3-bis [di (pyridine-2-ylamino)] benzene obtained in Example 3 in 1 methyl-2-pyrrolidone. The emission wavelength was then measured using a fluorescence spectrophotometer (Hitachi, Ltd., trade name: F 2500), and as a result, the 1,3 bis [di (pyridine-2-y) obtained in Example 3 was measured. It was confirmed that (l) amino] benzene had a light-emitting function, and the fluorescence wavelength was 397 nm, so that the 1,3 bis [di (pyridine-2—) obtained in Example 3 was used. Il) amino] benzene is an example For example, there is a high possibility that it can be suitably used as a material for a light emitting layer in an EL element or the like.

(Thermal stability)

The thermal decomposition temperature of 1,3 bis [di (pyridine-2-yl) amino] benzene obtained in Example 3 was measured by differential thermal analysis, and the glass transition temperature was determined by differential scanning calorimetry. It was measured.

Differential thermal analysis was performed by weighing 1,3 bis [di (pyridin-2-yl) amino] benzene lmg obtained in Example 3 from room temperature at a temperature increase rate of 10 ° CZ in a nitrogen atmosphere. The temperature was raised to 500 ° C. As a result, the thermal decomposition temperature was 260 ° C.

In differential scanning calorimetry, 1,3 bis [di (pyridine-2-yl) amino] benzene lOmg obtained in Example 3 was weighed and measured from room temperature at a temperature increase rate of 10 ° CZ in a nitrogen atmosphere. The temperature was raised to ° C. Next, after cooling from 200 ° C to room temperature at a temperature drop rate of 10 ° CZ, the temperature was raised again from room temperature to 200 ° C at a temperature increase rate of 10 ° CZ. As a result, the glass transition temperature was found to be 52 ° C. During this repeated measurement, no exothermic peak due to crystallization from amorphous was observed.

From these facts, 1,3 bis [di (pyridine-2-yl) amino] benzene obtained in Example 3 is thermally stable at 260 ° C. Since it can be easily formed and does not have a crystallization temperature, it can be seen that the formed amorphous film has excellent heat resistance.

Example 4

Preparation of 1,3bis [di (5-methylpyridine-2-yl) amino] benzene [general formula (2), Ι ^ = Η, R ² ~ R ³ = 5-methyl]

In Example 3, instead of 8.22 g (48 mmol) of bis (pyridine-2-yl) amine, 9.55 g (48 mmol) of bis (5-methylpyridine-2-yl) amine was used. Except for the above, in the same manner as in Example 3, 5.89 g of 1,3 bis [di (5-methylpyridine 2-yl) amino] benzene of the present invention was obtained. The yield of the obtained 1,3 bis [di (5-methylpyridine-1-yl) amino] benzene was 52% based on 1,3 dibromobenzene used.

The compound strength obtained was 1, 3 bis [di (5-methylpyridine-2-yl) amino] ben It was confirmed by the following analysis results that it was Zen.

Molecular weight (mass spectrometry by atmospheric pressure ionization method): 472

IR (KBr): 3030, 2991, 1590, 1566, 1484, 1466, 1447, 1350, 1320, 12 61, 1035, 778, 710cm " ¹

[0070] Evaluation

The 1,3-bis [di (5-methylpyridin-2-yl) amino] benzene obtained in Example 4 was evaluated for luminescent properties and thermal stability.

(Luminescent characteristics)

In the same manner as in Example 3, the emission wavelength was measured using a fluorescence spectrophotometer. As a result, it was confirmed that 1,3-bis [di (5-methylpyridine-2-yl) amino] benzene obtained in Example 4 had a light emitting function. The fluorescence wavelength was 404 nm. Therefore, the 1,3-bis [di (5-methylpyridine-2-yl) amino] benzene obtained in Example 4 can be suitably used as a material for a light emitting layer in, for example, an EL device. It turns out that there is a high possibility of being able to do it.

(Thermal stability)

Measurement was performed in the same manner as in Example 3.

Differential thermal analysis showed that the thermal decomposition temperature was 262 ° C.

Differential scanning calorimetry showed that the glass transition temperature was 48 ° C. In addition, during this repeated measurement, no exothermic peak due to crystallization from amorphous was observed. Therefore, the 1,3-bis [di (5-methylpyridine) obtained in Example 4 2-yl) amino] benzene has a thermal decomposition temperature of 262 ° C and is thermally stable, so it can be easily formed by vapor deposition, etc., and it has no crystallization temperature. It can be seen that the amorphous film has excellent heat resistance.

[0071] Example 5

Preparation of 2, 6-bis [(phenol) (pyridine-2-yl) amino] pyridine [general formula (3), 1 ^ ~ = H]

To a 300 mL four-necked flask equipped with a condenser, thermometer and stirrer, add 2, 6- Dibromopyridine 5.69 g (24 mmol), (Phenol) (pyridine-2-yl) amamine 8. 16 g (48 mmol), Tris (dibenzylideneacetone) Ninoradium (0) 1.10 g (l. 2 Mmol), 2,2, -bis (diphenylphosphino) -1,1, -binaphthyl 2.24 g (3.6 mmol), sodium-tert-butoxide 6.92 g (72 mmol) and toluene 240 mL. . Next, the temperature was raised to 100 ° C. under a nitrogen atmosphere, and the reaction was further stirred at the same temperature for 8 hours. Thereafter, the reaction solution is cooled to room temperature, and the precipitate is filtered and dried to obtain 6.75 g of 2,6-bis [(phenol) (pyridine-2-yl) amino] pyridine of the present invention. It was. The yield of the resulting 2,6-bis [(phenol) (pyridine-2-yl) amino] pyridine was 68% based on the 2,6-dibu-momopyridine used.

It was confirmed by the following analysis results that the obtained compound was 2,6-bis [(phenol) (pyridine-2-yl) amino] pyridin.

Molecular weight (mass analysis by atmospheric pressure ionization method): 415

IR (KBr): 1583, 1568, 1494, 1466, 1447, 1415, 1349, 1320, 1304, 12 74, 1261, 1072, 778cm " ¹

Evaluation

The 2,6-bis [(phenol) (pyridine-2-yl) amino] pyridine obtained in Example 5 was evaluated for luminescent properties and thermal stability.

(Luminescent characteristics)

Sample obtained by dissolving 2,6-bis [(phenol) (pyridine-2-yl) amino] pyridine obtained in Example 5 in 1-methyl-2-pyrrolidone (concentration: 1 X 10 " ³ g / L) was prepared, and the emission wavelength was measured using a fluorescence spectrophotometer (trade name F-2500, Hitachi, Ltd.) As a result, 2, 6— Bis [(phenol) (pyridine-2-yl) amino] pyridine was confirmed to have a light-emitting function, and the fluorescence wavelength was 423 nm. It can be seen that the obtained 2,6-bis [(phenyl) (pyridine-2-yl) amino] pyridine is likely to be suitably used as a light emitting layer material in, for example, EL devices.

(Thermal stability)

By differential thermal analysis, 2, 6-bis [(phenol) The thermal decomposition temperature of [r) amino] pyridine was measured, and the glass transition temperature was further measured by differential scanning calorimetry.

Differential thermal analysis was performed by weighing 1 mg of 2,6bis [(phenol) (pyridine-2-yl) amino] pyridine obtained in Example 5 and raising the temperature by 10 ° CZ in a nitrogen atmosphere. The temperature was raised from room temperature to 500 ° C. As a result, the thermal decomposition temperature was 265 ° C.

Differential scanning calorimetry was performed by weighing 2,6 bis [(phenyl) (pyridine-2-yl) amino] pyridine lOmg obtained in Example 5 at room temperature at a temperature increase rate of 10 ° CZ in a nitrogen atmosphere. The temperature was raised to 200 ° C. Next, after cooling from 200 ° C to room temperature at a temperature drop rate of 10 ° CZ, the temperature was raised again from room temperature to 200 ° C at a temperature increase rate of 10 ° CZ. As a result, the glass transition temperature was 52 ° C. In addition, during this repeated measurement, no exothermic peak due to crystallization from amorphous was observed.

From these results, the 2,6bis [(phenol) (pyridine-2-yl) amino] pyridine obtained in Example 5 has a thermal decomposition temperature of 265 ° C and is thermally stable. It can be seen that the deposited amorphous film has excellent heat resistance because it can be easily formed by vapor deposition and has no crystallization temperature.

Example 6

2, 6 Bis [(4-methylphenol) (5-methylpyridine-1-yl) amino] pyridine [General formula (3), Ι ^ = Η, R ² = 5-methyl, R ³ = 4 —Methyl] Preparation

In Example 5, instead of (phenol) (pyridine-2-yl) amine 8.16 g (48 mmol), (4-methylphenol) (5-methylpyridine-2-yl) amine 9 2.90 g of 2,6bis [(4 methylphenol) (5-methylpyridine-2-yl) amino] pyridine of the invention as in Example 5 except that 50 (48 mmol) was used. Got. The yield of 2,6bis [(4-methylphenol) (5-methylpyridine-2-yl) amino] pyridine obtained was 61% based on 2,6 dibromopyridine used.

The obtained compound was confirmed to be 2, 6 bis [(4 methylphenol) (5 methylpyridine 2 -yl) amino] pyridine by the following analysis results.

Molecular weight (mass spectrometry by atmospheric pressure ionization method): 471

IR (KBr): 3030, 2984, 1587, 1562, 1490, 1456, 1435, 1342, 1310, 12 69, 1065, 778, 710cm "

[0074] Evaluation

The 2,6bis [(4-methylphenol) (5-methylpyridine-2-yl) amino] pyridine obtained in Example 6 was evaluated for luminescent properties and thermal stability.

(Luminescent characteristics)

In the same manner as in Example 5, the emission wavelength was measured using a fluorescence spectrophotometer. As a result, it was confirmed that the 2,6bis [(4 methylphenol) (5 methylpyridine 2yl) amino] pyridine obtained in Example 6 had a light emitting function. The fluorescence wavelength was 430 nm. Accordingly, the 2,6bis [(4 methylphenol) (5-methylpyridine-2-yl) amino] pyridine obtained in Example 6 should be suitably used as a material for the light emitting layer in, for example, an EL device. It is clear that there is a high possibility that

(Thermal stability)

Measurement was performed in the same manner as in Example 5.

Differential thermal analysis showed that the thermal decomposition temperature was 268 ° C.

Differential scanning calorimetry showed that the glass transition temperature was 49 ° C. In addition, during this repeated measurement, no exothermic peak due to crystallization from amorphous was observed. From these results, it was confirmed that 2, 6 bis [(4 methylphenol) (5 Methyl pyridine-2-yl) amino] pyridine has a thermal decomposition temperature of 268 ° C and is thermally stable, so it can be easily formed by vapor deposition, and it does not have a crystallization temperature. It can be seen that the amorphous film formed has excellent heat resistance.

[0075] Example 7

1, 3 Bis [(Phenol) (pyridine-2-yl) amino] benzene [General formula (4)! ^ Preparation of ~R ³ = H]

In a 300 mL four-necked flask equipped with a condenser, a thermometer and a stirrer, 1, 3-dibromobenzene 5.66 g (24 mmol), (phenol) (pyridine-2-yl) amamine 8. 16 g (48 mmol), tris (dibenzylideneacetone) ninoradium (0) 1.10 g (l. 2 mmol), 2,2,1 bis (diphenylphosphino) 1,1,1, binaphthyl 2.24 g (3. 6 mmol), Na Thorium-tert-butoxide 6.92 g (72 mmol) and toluene 240 mL were charged. Next, the temperature was raised to 100 ° C. under a nitrogen atmosphere, and the reaction was further stirred at the same temperature for 8 hours. Thereafter, the reaction solution is cooled to room temperature, and the precipitate is filtered and dried to obtain 5.75 g of 1,3-bis [(phenyl) (pyridine-2-yl) amino] benzene of the present invention. It was. The yield of the obtained 1,3-bis [(phenol) (pyridine-2-yl) amino] benzene was 58% with respect to the 1,3-dib-mouthed mobenzene used.

The obtained compound strength was confirmed to be 1,3-bis [(phenol) (pyridine-2-yl) amino] benzene by the following analysis results.

Molecular weight (mass spectrometry by atmospheric pressure ionization method): 414

IR (KBr): 1583, 1568, 1494, 1466, 1447, 1415, 1351, 1320, 1304, 12 74, 1261, 1157, 1072, 778cm " ¹

Evaluation

The 1,3-bis [(phenol) (pyridine-2-yl) amino] benzene obtained in Example 7 was evaluated for luminescent properties and thermal stability.

(Luminescent characteristics)

Sample obtained by dissolving 1,3-bis [(phenol) (pyridine-2-yl) amino] benzene obtained in Example 7 in 1-methyl-2-pyrrolidone (concentration: 1 X 10 ") ³ g / L) was prepared, and the emission wavelength was measured using a fluorescence spectrophotometer (trade name F-2500, Hitachi, Ltd.) As a result, 1, 3— Bis [(phenol) (pyridine-2-yl) amino] benzene was confirmed to have a light-emitting function, and the fluorescence wavelength was 43 2 nm. The obtained 1,3-bis [(phenol) (pyridine-2-yl) amino] benzene is likely to be suitably used as a material for a light emitting layer in, for example, an EL device. I understand.

(Thermal stability)

The thermal decomposition temperature of 1,3-bis [(phenol) (pyridine-2-yl) amino] benzene obtained in Example 7 was measured by differential thermal analysis, and further analyzed by differential scanning calorimetry. The glass transition temperature was measured.

The differential thermal analysis was performed using 1,3-bis [(phenol) (pyridine-2-yl) a obtained in Example 7. Mino] benzene lmg was weighed and heated from room temperature to 500 ° C at a temperature increase rate of 10 ° CZ in a nitrogen atmosphere. As a result, the thermal decomposition temperature was 268 ° C.

Differential scanning calorimetry was performed by weighing 1,3 bis [(phenyl) (pyridine-2-yl) amino] benzene lOmg obtained in Example 7 at room temperature at a rate of 10 ° CZ in a nitrogen atmosphere. The temperature was raised to 200 ° C. Next, after cooling from 200 ° C to room temperature at a temperature drop rate of 10 ° CZ, the temperature was raised again from room temperature to 200 ° C at a temperature increase rate of 10 ° CZ. As a result, the glass transition temperature was found to be 51 ° C. Also, during this repeated measurement, no exothermic peak due to crystallization of amorphous force was observed.

From these facts, the 1,3bis [(phenol) (pyridine-2-yl) amino] benzene obtained in Example 7 has a thermal decomposition temperature of 268 ° C and is thermally stable. It can be easily formed by vapor deposition or the like, and since it does not have a crystallization temperature, it can be seen that the formed amorphous film has excellent heat resistance.

[0077] Example 8

1, 3 Bis [(4-Methylphenol) (5-Methylpyridine-2-yl) amino] benzene [General formula (4), Ι ^ = Η, R ² = 5—Methyl, R ³ = 4— Of Methyl]

In Example 7, instead of (phenol) (pyridine-2-yl) amine 8.16 g (48 mmol), (4-methylphenol) (5-methylpyridine-2-yl) amine 9 1. 53 bis [(4 methylphenol) (5-methylpyridine-2-yl) amino] benzene of the present invention in the same manner as in Example 7 except that 50 (48 mmol) was used 5.53 g Got. The yield of the obtained 1,3 bis [(4 methylphenol) (5 methylpyridine 2yl) amino] benzene was 49% based on the 1,3 dibromobenzene used.

The obtained compound was confirmed to be 1, 3 bis [(4 methylphenol) (5 methylpyridine-2-yl) amino] benzene by the following analysis results.

Molecular weight (mass spectrometry by atmospheric pressure ionization method): 470

IR (KBr): 3032, 2985, 1583, 1565, 1489, 1466, 1445, 1349, 1320, 12 69, 1055, 778, 710cm " ¹

[0078] Evaluation

1,3 bis [(4-methylphenol) (5-methylpyridine-2-y) obtained in Example 8 Lumino) benzene was evaluated for its luminescent properties and thermal stability.

(Luminescent characteristics)

In the same manner as in Example 7, the emission wavelength was measured using a fluorescence spectrophotometer. As a result, it was confirmed that the 1,3 bis [(4-methylphenol) (5-methylpyridine-1-yl) amino] benzene obtained in Example 8 had a light emitting function. The fluorescence wavelength was 435 nm. Therefore, 1,3 bis [(4-methylphenol) (5-methylpyridine 2-yl) amino] benzene obtained in Example 8 is suitably used as a material for a light emitting layer in, for example, an EL device. It turns out that there is a high possibility of being able to.

(Thermal stability)

Measurement was carried out in the same manner as in Example 7.

Differential thermal analysis showed that the thermal decomposition temperature was 267 ° C.

Differential scanning calorimetry showed that the glass transition temperature was 49 ° C. In addition, during this repeated measurement, no exothermic peak due to crystallization from amorphous was observed. Therefore, the 1,3 bis [(4 methylphenol) (5 Methyl pyridine-2-yl) amino] benzene has a thermal decomposition temperature of 267 ° C and is thermally stable. Therefore, it can be easily formed by vapor deposition and has no crystallization temperature. It can be seen that the amorphous film formed has excellent heat resistance.

Industrial applicability

Since the compound of the present invention is thermally stable and can form an amorphous film having excellent heat resistance, it is useful as a charge transport material and a light emitting layer material in EL devices and the like.

Claims

Claim [1] General formula (I)

[Chemical 1]

(In the formula, each of! ^ To independently represents a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubermoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoyl group having 1 to 10 carbon atoms. These may be the same or different. V represents a nitrogen atom or carbon atom, two Ws simultaneously represent a nitrogen atom or carbon atom, and V and W may be the same or different. A compound represented by:

[2] The compound according to claim 1, wherein in the general formula (I), V and W are both nitrogen atoms.

[3] The compound according to claim 1, wherein, in the general formula (I), V is a carbon atom and W is a nitrogen atom.

[4] The compound according to claim 1, wherein, in the general formula (I), V is a nitrogen atom and W is a carbon atom.

5. The compound according to claim 1, wherein in the general formula (I), V and W are both carbon atoms.

[6] In the general formula (I),! The compound according to any one of claims 1 to 5, wherein ^ ¹ to! ^ ³ are all hydrogen atoms.

[7] General formula (Π):

[Chemical 2]

(In the formula, R ¹ represents a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubamoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoyl group having 1 to 10 carbon atoms, and V represents a nitrogen atom or a carbon atom. Dihalogeno monocyclic compounds represented by the general formula (III):

[Chemical 3]

(In the formula, R ² and R ³ are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubamoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms. And N may be the same or different. W represents a nitrogen atom or a carbon atom.) And an amine compound represented by a noradium compound and a phosphine compound. General formula (I) characterized by reacting in the presence of a catalyst and a base containing:

(In the formula, each of! ^ ~ Is independently a hydrogen atom, a hydroxyl group, a carboxyl group, a cyano group, a strong rubermoyl group, an alkyl group having 1 to 10 carbon atoms, or an alkanoy having 1 to 10 carbon atoms May be the same or different, V represents a nitrogen atom or carbon atom, two Ws simultaneously represent a nitrogen atom or carbon atom, and V and W are the same. Also different. The manufacturing method of the compound represented by this.

8. The method for producing a compound according to claim 7, wherein in the general formula (I), V and W are both nitrogen atoms.

[9] The process for producing a compound according to [7], wherein in the general formula (I), V is a carbon atom and W is a nitrogen atom.

[10] The method for producing a compound according to [7], wherein in the general formula (I), V is a nitrogen atom and W is a carbon atom.

11. The method for producing a compound according to claim 7, wherein in the general formula (I), V and W are both carbon atoms.