CN102276589A - Compounds - Google Patents

Abstract

The invnetion provides compounds in formula (1). In the formula (1), R1 indicates hydrogen atom or univalent alkyl having substituent group with 1 to 30 carbon atoms. The -CH2- contained in the alkyl can be substituted by -O- or -CO-. R2 indicates hydrogen atom, cyanogroup or carbamoyl group. R3 indicates alkyl group with 1- 4 carbon atoms. The hydrogen atom contained by the alkyl group can be substituted by halogen atoms. R4 to R8 indicates hydrogen atom, alkyl group with 1-8 carbon atoms, alkoxy group with 1-8 carbon atoms, alkoxy alkyl group with 2-8 carbon atoms, hydroxy, cyano group, nitro group, halogen group and at least one group expressed in a formula (1a) separately. In formula (1a), L1 indicates alkylene group with 1-8 carbon atoms.

Description

Dye composition

Technical field

The present invention relates to as useful compound of dyestuff etc.

Background technology

Dyestuff for example is used for utilizing reflected light or transmitted light in fields such as filamentary material, liquid crystal indicator, ink-jets, carries out color and shows.

For example, Japan's patent application embodiment 1 of disclosing the 2004-2630 communique has put down in writing the compound that following formula is represented.

Above-claimed cpd is the dyestuff of photostabilization and excellent heat resistance, and is known to water color ink.On the other hand, the solvability of this compound in organic solvent is little, be used as liquid crystal indicator etc. display unit the employed dyestuff of colour filter and be not easy.

Summary of the invention

The present invention is following invention.

[1] compound shown in the formula (I).

[in the formula (I), R ¹The expression hydrogen atom maybe can have the monovalence alkyl of substituent carbonatoms 1～30, and this alkyl is contained-CH ₂-can by-O-or-CO-replaces.

R ²Expression hydrogen atom, cyano group or formamyl.

R ³The alkyl of expression carbonatoms 1～4, the contained hydrogen atom of this alkyl can be replaced by halogen atom.

R ⁴～R ⁸The group of alkoxyalkyl, hydroxyl, cyano group, nitro, halogen atom or formula (Ia) expression of representing alkoxyl group, the carbonatoms 2～8 of alkyl, the carbonatoms 1～8 of hydrogen atom, carbonatoms 1～8 independently of each other, the group shown at least one expression (Ia).]

[in the formula (Ia), L ¹The alkylidene group of expression carbonatoms 1～8.]

[2] compound of putting down in writing as [1], R ⁸It is the group shown in the formula (Ia).

[3] compound of putting down in writing as [1] or [2], R ¹Be-L ²-X ¹-R ⁹The group of expression.

[wherein, L ²The alkylidene group of expression carbonatoms 1～8.X ¹Expression-CO-O-.R ⁹The univalent aliphatic series alkyl of expression hydrogen atom or carbonatoms 1～20, this aliphatic alkyl is contained-CH ₂-can by-O-or-CO-replaces.]

[4] compound of each record in [1]～[3], R ¹Be-L ²-X ¹-L ³-X ²-R ¹⁰The group of expression.

[wherein, L ²And X ¹Meaning the same.L ³The alkylidene group of expression carbonatoms 1～8.X ²Expression-CO-O-.R ¹⁰Expression hydrogen atom, methyl or ethyl.]

[5] as [3] or [4] described compound, X ¹Be *-O-CO-.

[wherein, * represents and L ²Bonding position.]

[6] compound of each record in [1]～[5], R ⁴～R ⁸In at least one is a nitro.

[7] a kind of compound with each record in [1]～[6] is the dyestuff of effective constituent.

The effect of invention

The solvability excellence of compound of the present invention in organic solvent as the employed dyestuff of colour filter of the display unit of liquid crystal indicator etc., is excellent.

Embodiment

The present invention is the compound shown in the formula (I) (below be sometimes referred to as compound (I)).

[in the formula (I), R ¹The expression hydrogen atom maybe can have the monovalence alkyl of substituent carbonatoms 1～30, and this alkyl is contained-CH ₂-can by-O-or-CO-replaces.

R ²Expression hydrogen atom, cyano group or formamyl.

R ³The alkyl of expression carbonatoms 1～4, the contained hydrogen atom of this alkyl can be replaced by halogen atom.

R ⁴～R ⁸The group of alkoxyalkyl, hydroxyl, cyano group, nitro, halogen atom or formula (Ia) expression of representing alkoxyl group, the carbonatoms 2～8 of alkyl, the carbonatoms 1～8 of hydrogen atom, carbonatoms 1～8 independently of each other, the group of at least one expression (Ia) expression.]

[in the formula (Ia), L ¹The alkylidene group of expression carbonatoms 1～8.]

R ¹Can the having that substituent monovalence alkyl has the univalent aliphatic series alkyl for example, has substituent univalent aliphatic series alkyl, the monovalence alicyclic hydrocarbon radical, have substituent monovalence alicyclic hydrocarbon radical, monovalence aromatic hydrocarbyl, have substituent monovalence aromatic hydrocarbyl and their combination group of expression.The carbonatoms of this monovalence alkyl is 1～30.

The substituting group that described alkyl can have have for example hydroxyl, carboxyl, sulfane base (RS-, sulfanyl), the amino that can be replaced by the alkyl of carbonatoms 1～6 and the alkoxyl group of carbonatoms 1～4.

Described aliphatic alkyl has methyl, ethyl, propyl group, isobutyl-, butyl, the tertiary butyl, hexyl, heptyl, octyl group, nonyl, decyl etc. for example.Have substituent aliphatic alkyl 2-hydroxyethyl, 2-amino-ethyl, 2-sulfane base ethyl etc. are arranged for example.

Described alicyclic hydrocarbon radical has cyclopentyl, cyclohexyl etc. for example.Have substituent alicyclic hydrocarbon radical 4-methylcyclohexyl, 4-hydroxymethyl cyclohexyl, 4-aminocyclohexyl, 4-(N are arranged for example, N '-dimethylamino) cyclohexyl, 2-aminocyclohexyl, 2-(N, N '-dimethylamino) cyclohexyl, 4-carboxyl cyclohexyl, 4-methoxyl group cyclohexyl, 2-carboxyl cyclohexyl etc.

Described aromatic hydrocarbyl has phenyl, naphthyl etc. for example.

Have substituent aromatic hydrocarbyl 4-hydroxyphenyl, 4-p-methoxy-phenyl, 2-carboxyl phenyl, 4-carboxyl phenyl etc. are arranged for example.

The preferred carbonatoms 1～20 of described monovalence alkyl, more preferably carbonatoms 2～16.

Described alkyl is contained-CH ₂-can by-O-or-CO-replaces.In the described alkyl, preferably have 2～4-CH ₂-quilt-O-or-CO-replaces, more preferably have 2 adjacency-CH ₂-quilt-CO-or-O-replaces.

R ¹Preferably-L ²-X ¹-R ⁹Shown group, more preferably-L ²-X ¹-L ³-X ²-R ¹⁰Shown group.R ¹During for these groups, the solubleness of compound of the present invention in organic solvent has the tendency of raising.

L ²And L ³Be the alkylidene group of carbonatoms 1～8 independently of each other, methylene radical, ethylene, trimethylene, 1 are for example arranged for example, 2-propylidene, tetramethylene, 1,3-butylidene, 1,2-butylidene, 1,5-pentylidene, hexamethylene, 1, the inferior heptyl of 7-, octamethylene etc.

L ²The alkylidene group of preferred carbonatoms 1～5, the more preferably alkylidene group of carbonatoms 2～4.

L ³The alkylidene group of preferred carbonatoms 1～4, the more preferably alkylidene group of carbonatoms 1～2.

X ¹And X ²Be-CO-O-.X ¹Preferably (* represents and L *-O-CO- ²Bonding position).X ¹During for *-O-CO-, compound of the present invention is made easily.

R ⁹Be the univalent aliphatic series alkyl of hydrogen atom or carbonatoms 1～20, this aliphatic alkyl is contained-CH ₂-can by-O-or-CO-replaces.Expression R ⁹Aliphatic alkyl have for example as the expression R ¹The group lifted of univalent aliphatic series alkyl in the aliphatic alkyl of carbonatoms 1～20, the more preferably alkyl of carbonatoms 1～10.

R ¹⁰Be hydrogen atom, methyl or ethyl, preferred ethyl.

-L ²-X ¹-R ⁹The for example group of formula (f-1)～formula (f-25) expression is arranged for example.Wherein, preferred-L ²-X ¹-L ³-X ²-R ¹⁰Formula (f-1)～formula (f-20) expression group is for example arranged for example, the more preferably group of formula (f-1), formula (f-2), formula (f-5), formula (f-6), formula (f-9), formula (f-10), formula (f-13), formula (f-14), formula (f-17) and formula (f-18) expression, the further group of preferred formula (f-2), formula (f-6), formula (f-10), formula (f-14) and formula (f-18) expression.

R ²Be hydrogen atom, cyano group or formamyl.Wherein, from easy acquisition raw material aspect, preferred cyano group.

Expression R ³The alkyl of carbonatoms 1～4 methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, the tertiary butyl etc. are arranged for example.The contained hydrogen atom of this alkyl can be replaced by halogen atom.

As halogen atom, fluorine atom, chlorine atom, bromine atoms etc. are arranged for example.Hydrogen atom is had for example trifluoromethyl, pentafluoroethyl group etc. for example by the alkyl of the carbonatoms 1～4 that halogen atom replaces.

R ³Preferable methyl and trifluoromethyl, more preferably methyl.

R ⁴～R ⁸Be the group of alkoxyalkyl, hydroxyl, cyano group, nitro, halogen atom or formula (Ia) expression of alkoxyl group, the carbonatoms 2～8 of alkyl, the carbonatoms 1～8 of hydrogen atom, carbonatoms 1～8 independently of each other, at least one is the group of formula (Ia) expression.

In the compound (I), R ⁴～R ⁸In at least one have the group of formula (Ia) expression, so the solvability of compound (I) in organic solvent has the tendency of raising.

In the compound (I), as R ⁴～R ⁸, preferably except the group of formula (Ia) expression, also have alkyl, chloro or the bromo of hydrogen atom, nitro, carbonatoms 1～6.

Preferred R ⁴～R ⁸One of be the group of formula (Ia) expression.Wherein, preferred R ⁸Group for formula (Ia) expression.

L ¹It is the alkylidene group of carbonatoms 1～8.This alkylidene group has and L for example ²And L ³In the identical group lifted as the alkylidene group of carbonatoms 1～8.L ¹The alkylidene group of preferred carbonatoms 1～4, more preferably methylene radical.

In addition, R ⁴～R ⁸In have one at least for nitro.Compound (I) divides optical concentration that the tendency of raising is arranged when having nitro.R ⁴～R ⁸In, preferably have 1～2 nitro, more preferably there is 1.Wherein, preferred R ⁵Or R ⁶Be nitro, more preferably R ⁶Be nitro.When nitro is in these positions, divide optical concentration that the tendency of further raising is arranged.

R ⁴～R ⁸In, preferred R ⁸Be the group of formula (Ia) expression, R ⁵Or R ⁶Be nitro, more preferably R ⁸Be the group of formula (Ia) expression, R ⁵Be hydrogen atom or methyl, R ⁶Be nitro.R ⁴And R ⁷Be preferably the alkyl of hydrogen atom or carbonatoms 1～6, more preferably hydrogen atom or methyl.

R ⁴～R ⁸The alkyl of shown carbonatoms 1～8 has for example straight chain shape alkyl of methyl, ethyl, n-propyl, normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl etc. for example;

Sec.-propyl, isobutyl-, sec-butyl, isopentyl, the 1-methyl amyl, the 2-methyl amyl, the 3-methyl amyl, the 4-methyl amyl, the 1-ethyl-butyl, the 2-ethyl-butyl, 1-methyl hexyl, 2-methyl hexyl, 3-methyl hexyl, 4-methyl hexyl, 5-methyl hexyl, the 1-ethyl pentyl group, the 2-ethyl pentyl group, the 3-ethyl pentyl group, 1-propyl group butyl, 1-(1-methylethyl) butyl, 1-(1-methylethyl)-2-methyl-propyl, the 1-methylheptyl, the 2-methylheptyl, the 3-methylheptyl, the 4-methylheptyl, the 5-methylheptyl, the 6-methylheptyl, the 1-ethylhexyl, the 2-ethylhexyl, the 3-ethylhexyl, the 4-ethylhexyl, 1-n-propyl amyl group, 2-propyl group amyl group, 1-(1-methylethyl) amyl group, 1-butyl butyl, the tertiary butyl, 1, the 1-dimethyl propyl, 1, the 1-dimethylbutyl, 1, the 2-dimethylbutyl, 1, the 3-dimethylbutyl, 2, the 3-dimethylbutyl, 1-ethyl-2-methyl-propyl, 1,1-dimethyl amyl group, 1,2-dimethyl amyl group, 1,3-dimethyl amyl group, 1,4-dimethyl amyl group, 2,2-dimethyl amyl group, 2,3-dimethyl amyl group, 2,4-dimethyl amyl group, 3,3-dimethyl amyl group, 3,4-dimethyl amyl group, 1-ethyl-1-methyl butyl, 1-ethyl-2-methyl butyl, 1-ethyl-3-methyl butyl, 2-ethyl-1-methyl butyl, 2-ethyl-3-methyl butyl, 1,1-dimethyl hexyl, 1,2-dimethyl hexyl, 1,3-dimethyl hexyl, 1,4-dimethyl hexyl, 1,5-dimethyl hexyl, 2,2-dimethyl hexyl, 2,3-dimethyl hexyl, 2,4-dimethyl hexyl, 2,5-dimethyl hexyl, 3,3-dimethyl hexyl, 3,4-dimethyl hexyl, 3,5-dimethyl hexyl, 4,4-dimethyl hexyl, 4,5-dimethyl hexyl, 1-ethyl-2-methyl amyl, 1-ethyl-3-methyl amyl, 1-ethyl-4-methyl amyl, 2-ethyl-1-methyl amyl, 2-ethyl-2-methyl amyl, 2-ethyl-3-methyl amyl, 2-ethyl-4-methyl amyl, 3-ethyl-1-methyl amyl, 3-ethyl-2-methyl amyl, 3-ethyl-3-methyl amyl, 3-ethyl-4-methyl amyl, 1-propyl group-1-methyl butyl, 1-propyl group-2-methyl butyl, 1-propyl group-3-methyl butyl, 1-(1-methylethyl)-1-methyl butyl, 1-(1-methylethyl)-2-methyl butyl, 1-(1-methylethyl)-3-methyl butyl, 1,1-diethyl butyl, 1,2-diethyl butyl etc. contain branched-chain alkyl.

The alkoxyl group of carbonatoms 1～8 for example has methoxyl group, oxyethyl group, propoxy-, butoxy, pentyloxy, hexyloxy, heptan oxygen base, octyloxy, 2-ethyl hexyl oxy etc. for example.

The alkoxyalkyl of carbonatoms 2～8 has for example methoxymethyl, methoxy ethyl, methoxy-propyl, methoxyl group butyl, methoxyl group amyl group, 1-ethoxycarbonyl propyl, 2-ethoxycarbonyl propyl, 1-oxyethyl group-1-methylethyl, 1-methyl-2-ethoxyethyl group, 1-(1-methyl ethoxy) propyl group, 2-(1-methyl ethoxy) propyl group, 1-(1-methyl ethoxy)-1-methylethyl, 2-(1-methyl ethoxy)-1-methylethyl, 3-ethoxycarbonyl propyl etc. for example.

Compound (I) has for example compound (I-1)～compound (I-126) etc. for example.In the table 1, R ¹The numbering of the above-mentioned group formula that exemplifies is represented on the hurdle.

[table 1]

Compound

R 1

R 2

R 3

R 4

R 5

R 6

R 7

L 1

I-1

f-1

CN

CH 3

H

H

NO 2

H

CH 2

I-2

f-3

CN

CH 3

H

H

NO 2

H

CH 2

I-3

f-4

CN

CH 3

H

H

NO 2

H

CH 2

I-4

f-5

CN

CH 3

H

H

NO 2

H

CH 2

I-5

f-6

CN

CH 3

H

H

NO 2

H

CH 2

I-6

f-7

CN

CH 3

H

H

NO 2

H

CH 2

I-7

f-8

CN

CH 3

H

H

NO 2

H

CH 2

I-8

f-9

CN

CH 3

H

H

NO 2

H

CH 2

I-9

f-10

CN

CH 3

H

H

NO 2

H

CH 2

I-10

f-11

CN

CH 3

H

H

NO 2

H

CH 2

I-11

f-12

CN

CH 3

H

H

NO 2

H

CH 2

I-12

f-13

CN

CH 3

H

H

NO 2

H

CH 2

I-13

f-15

CN

CH 3

H

H

NO 2

H

CH 2

I-14

f-16

CN

CH 3

H

H

NO 2

H

CH 2

I-15

f-17

CN

CH 3

H

H

NO 2

H

CH 2

I-16

f-18

CN

CH 3

H

H

NO 2

H

CH 2

I-17

f-19

CN

CH 3

H

H

NO 2

H

CH 2

I-18

f-20

CN

CH 3

H

H

NO 2

H

CH 2

I-19

f-22

CN

CH 3

H

H

NO 2

H

CH 2

I-20

f-23

CN

CH 3

H

H

NO 2

H

CH 2

I-21

f-24

CN

CH 3

H

H

NO 2

H

CH 2

I-22

f-25

CN

CH 3

H

H

NO 2

H

CH 2

I-23

f-1

CN

CF 3

H

CH 3

H

H

CH 2

I-24

f-3

H

CH 3

H

H

OCH 3

H

CH 2

I-25

f-4

CONH 2

CF 3

H

H

H

CH 2OCH 3

CH 2

I-26

f-5

CN

CH 3

H

H

OH

H

CH 2

I-27

f-6

H

CF 3

H

CN

H

H

CH 2

I-28

f-7

CONH 2

CH 3

F

H

H

H

CH 2

I-29

f-8

CN

CF 3

H

Cl

H

H

CH 2

I-30

f-9

H

CH 3

H

H

Br

H

CH 2

I-31

f-10

CONH 2

CF 3

H

CH 3

H

H

CH 2

I-32

f-11

CN

CH 3

H

H

OCH 3

H

CH 2

I-33

f-12

H

CF 3

H

H

H

CH 2OCH 3

CH 2

I-34

f-13

CONH 2

CH 3

H

H

OH

H

CH 2

I-35

f-15

CN

CF 3

H

CN

H

H

CH 2

I-36

f-16

H

CH 3

F

H

H

H

CH 2

I-37

f-17

CONH 2

CF 3

H

Cl

H

H

CH 2

I-38

f-18

CN

CH 3

H

H

Br

H

CH 2

I-39

f-19

H

CF 3

H

CH 3

H

H

CH 2

I-40

f-20

CONH 2

CH 3

H

H

OCH 3

H

CH 2

I-41

f-22

CN

CF 3

H

H

H

CH 2OCH 3

CH 2

I-42

f-23

H

CH 3

H

H

OH

H

CH 2

I-43

f-24

CONH 2

CF 3

H

CN

H

H

CH 2

I-44

f-25

CN

CH 3

F

H

H

H

CH 2

I-45

f-2

CN

CH 3

H

H

NO 2

H

CH 2

I-46

f-2

CN

CH 3

H

NO 2

H

H

CH 2

I-47

f-2

CN

CH 3

NO 2

H

H

H

CH 2

I-48

f-2

CN

CH 3

H

H

H

NO 2

CH 2

I-49

f-2

CN

CH 3

H

H

CH 3

H

CH 2

I-50

f-2

CN

CH 3

H

H

OCH 3

H

CH 2

I-51

f-2

CN

CH 3

H

H

CH 2OCH 3

H

CH 2

I-52

f-2

CN

CH 3

H

H

OH

H

CH 2

I-53

f-2

CN

CH 3

H

H

CN

H

CH 2

I-54

f-2

CN

CH 3

H

H

F

H

CH 2

I-55

f-2

CN

CH 3

H

H

Cl

H

CH 2

I-56

f-2

CN

CH 3

H

H

Br

H

CH 2

I-57

f-2

CN

CF 3

H

CH 3

H

H

CH 2

I-58

f-2

H

CH 3

H

H

OCH 3

H

CH 2

I-59

f-2

CONH 2

CF 3

H

H

H

CH 2OCH 3

CH 2

I-60

f-2

CN

CF 3

H

H

OH

H

CH 2

I-61

f-2

H

CH 3

H

CN

H

H

CH 2

I-62

f-2

CONH 2

CF 3

F

H

H

H

CH 2

I-63

f-2

CN

CF 3

H

Cl

H

H

CH 2

I-64

f-2

H

CH 3

H

H

Br

H

CH 2

I-65

f-14

CN

CH 3

H

H

NO 2

H

CH 2

I-66

f-14

CN

CH 3

H

NO 2

H

H

CH 2

I-67

f-14

CN

CH 3

NO 2

H

H

H

CH 2

I-68

f-14

CN

CH 3

H

H

H

NO 2

CH 2

I-69

f-14

CN

CH 3

H

H

CH 3

H

CH 2

I-70

f-14

CN

CH 3

H

H

OCH 3

H

CH 2

I-71

f-14

CN

CH 3

H

H

CH 2OCH 3

H

CH 2

I-72

f-14

CN

CH 3

H

H

OH

H

CH 2

I-73

f-14

CN

CH 3

H

H

CN

H

CH 2

I-74

f-14

CN

CH 3

H

H

F

H

CH 2

I-75

f-14

CN

CH 3

H

H

Cl

H

CH 2

I-76

f-14

CN

CH 3

H

H

Br

H

CH 2

I-77

f-14

CN

CF 3

H

CH 3

H

H

CH 2

I-78

f-14

H

CH 3

H

H

OCH 3

H

CH 2

I-79

f-14

CONH 2

CF 3

H

H

H

CH 2OCH 3

CH 2

I-80

f-14

CN

CF 3

H

H

OH

H

CH 2

I-81

f-14

H

CH 3

H

CN

H

H

CH 2

I-82

f-14

CONH 2

CF 3

F

H

H

H

CH 2

I-83

f-14

CN

CF 3

H

Cl

H

H

CH 2

I-84

f-14

H

CH 3

H

H

Br

H

CH 2

I-85

f-21

CN

CH 3

H

H

NO 2

H

CH 2

I-86

f-21

CN

CH 3

H

NO 2

H

H

CH 2

I-87

f-21

CN

CH 3

NO 2

H

H

H

CH 2

I-88

f-21

CN

CH 3

H

H

H

NO 2

CH 2

I-89

f-21

CN

CH 3

H

H

CH 3

H

CH 2

I-90

f-21

CN

CH 3

H

H

OCH 3

H

CH 2

I-91

f-21

CN

CH 3

H

H

CH 2OCH 3

H

CH 2

I-92

f-21

CN

CH 3

H

H

OH

H

CH 2

I-93

f-21

CN

CH 3

H

H

CN

H

CH 2

I-94

f-21

CN

CH 3

H

H

F

H

CH 2

I-95

f-21

CN

CH 3

H

H

C1

H

CH 2

I-96

f-21

CN

CH 3

H

H

Br

H

CH 2

I-97

f-21

CN

CF 3

H

CH 3

H

H

CH 2

I-98

f-21

H

CH 3

H

H

OCH 3

H

CH 2

I-99

f-21

CONH 2

CF 3

H

H

H

CH 2OCH 3

CH 2

I-100

f-21

CN

CF 3

H

H

OH

H

CH 2

I-101

f-21

H

CH 3

H

CN

H

H

CH 2

I-102

f-21

CONH 2

CF 3

F

H

H

H

CH 2

I-103

f-21

CN

CF 3

H

Cl

H

H

CH 2

I-104

f-21

H

CH 3

H

H

Br

H

CH 2

I-105

f-1

CN

CH 3

H

NO 2

H

H

CH 2

I-106

f-3

CN

CH 3

H

NO 2

H

H

CH 2

I-107

f-4

CN

CH 3

H

NO 2

H

H

CH 2

I-108

f-5

CN

CH 3

H

NO 2

H

H

CH 2

I-109

f-6

CN

CH 3

H

NO 2

H

H

CH 2

I-110

f-7

CN

CH 3

H

NO 2

H

H

CH 2

I-111

f-8

CN

CH 3

H

NO 2

H

H

CH 2

I-112

f-9

CN

CH 3

H

NO 2

H

H

CH 2

I-113

f-10

CN

CH 3

H

NO 2

H

H

CH 2

I-114

f-11

CN

CH 3

H

NO 2

H

H

CH 2

I-115

f-12

CN

CH 3

H

NO 2

H

H

CH 2

I-116

f-13

CN

CH 3

H

NO 2

H

H

CH 2

I-117

f-15

CN

CH 3

H

NO 2

H

H

CH 2

I-118

f-16

CN

CH 3

H

NO 2

H

H

CH 2

I-119

f-17

CN

CH 3

H

NO 2

H

H

CH 2

I-120

f-18

CN

CH 3

H

NO 2

H

H

CH 2

I-121

f-19

CN

CH 3

H

NO 2

H

H

CH 2

I-122

f-20

CN

CH 3

H

NO 2

H

H

CH 2

I-123

f-22

CN

CH 3

H

NO 2

H

H

CH 2

I-124

f-23

CN

CH 3

H

NO 2

H

H

CH 2

I-125

f-24

CN

CH 3

H

NO 2

H

H

CH 2

I-126

f-25

CN

CH 3

H

NO 2

H

H

CH 2

Wherein, preferred compound (I-1)～compound (I-22), compound (I-45), compound (I-46), compound (I-65), compound (I-66), compound (I-85), compound (I-86) and compound (I-105)～compound (I-126), more preferably compound (I-45), compound (I-46), compound (I-65), compound (I-66), compound (I-85), compound (I-21), compound (I-125) and compound (I-86).

When compound (I) is these compounds, the high tendency of solvability in organic solvent is arranged.

The method of making compound of the present invention is described.

In the compound (I), for example, R ⁸During for the group of formula (Ia) expression, the hydroxyl reaction (esterification) that the carboxyl that has by the azo-compound that makes formula (a4) expression and the compound of formula (a5) expression have, can obtain the compound (below, be referred to as " compound (Iaa) " sometimes) of formula (Iaa) expression.R ⁴～R ⁷In any when being the group of formula (Ia) expression, also can adopt the method for making compound (Iaa), similarly make.

[in formula (a4) and the formula (a5), R ¹～R ⁷And L ¹The meaning of expression is the same.]

[in the formula (Iaa), R ¹～R ⁷And L ¹The meaning of expression is the same.]

The azo-compound of formula (a4) expression can be according to the record of the special fair 7-88633 communique of Japanese Patent, and the diazonium salt by making formula (a2) expression and the pyridinone compounds generation diazo coupling reaction of formula (a3) expression are made.

The diazonium salt of formula (a2) expression can for example utilize nitrous acid, nitrite or nitrous acid ester to make the amine diazotization of formula (a1) expression, makes.

The compound of amine and formula (a5) expression that the pyridinone compounds of formula (a3) expression for example can be by making formula (a4) expression and the compound of formula (a6) expression react and obtain.

[in formula (a1), formula (a2), formula (a3), formula (a4), formula (a5) and the formula (a6), R ¹～R ⁷The meaning of expression is the same.A ¹Expression inorganic anion or organic anion.]

Described inorganic anion has for example fluoride ion, chloride ion, bromide ion, iodide ion, perchlorate, hypochlorite etc. for example.

Described organic anion has for example CH for example ₃COO-, PhCOO-etc.

Preferred chloride ion, bromide ion, CH ₃COO-etc.

Diazo coupling reaction takes place in the diazonium salt by making formula (a2) expression and the pyridinone compounds of formula (a3) expression in aqueous solvent, can make the azo-compound of formula (a4) expression.Preferred-5 ℃～60 ℃ of temperature of reaction, more preferably 0 ℃～30 ℃.Preferred 1 hour～12 hours of reaction times, more preferably 1 hour～4 hours.Described aqueous solvent has water, N-Methyl pyrrolidone etc., preferably water for example.

Esterification takes place in the azo-compound by making formula (a4) expression and the compound of formula (a5) expression in the presence of organic solvent, can obtain compound (Iaa).This esterification is preferably used condensing agent (1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride and dicyclohexyl carbodiimide etc.) and/or additive (N, N-dimethyl-4-aminopyridine, triethylamine, (±)-10-camphorsulfonic acid etc.).Preferred-5 ℃～60 ℃ of temperature of reaction, more preferably 0 ℃～30 ℃.Preferred 1 hour～12 hours of reaction times, more preferably 1 hour～5 hours.

The usage quantity of the compound of formula (a5) expression is preferably 0.5～10 mole, more preferably 1～5 mole with respect to 1 mole of the azo-compound of formula (a4) expression.

Described organic solvent has the amide solvent of ketone solvent, N-Methyl pyrrolidone, 1-Methyl-2-Pyrrolidone of nitro-hydrocarbon solvent, hexone of halogenated hydrocarbon solvent, oil of mirbane of hydrocarbon solvent, chlorobenzene, dichlorobenzene, chloroform of toluene, dimethylbenzene etc. etc. etc. etc. etc. for example.

In the compound of the present invention, R ¹For-L ²-X ¹-R ⁹And X ¹(* represents and L for the compound (I) of *-O-CO- ²Bonding position) time, i.e. the compound (following be referred to as sometimes " compound (Ib) ") of formula (Ib) expression describes its manufacture method.

[in the formula (Ib), R ²～R ⁷, R ⁹, L ¹And L ²The meaning of expression is the same.]

By adopting and above-mentioned the same method, make the diazonium salt of formula (a2) expression and the pyridinone compounds generation diazo coupling reaction of formula (b3) expression, can make the azo-compound of formula (b4) expression.

[in formula (b3) and the formula (b4), R ²～R ⁷And L ²The meaning of expression is the same.]

Then,, the azo-compound of formula (b4) expression and the compound of formula (b5) expression are reacted, can obtain the azo-compound of formula (b6) expression by in the presence of organic solvent.Preferred 30 ℃～180 ℃ of temperature of reaction, more preferably 50 ℃～120 ℃.Preferred 1 hour～12 hours of reaction times, more preferably 1 hour～4 hours.

[in formula (b5) and the formula (b6), R ²～R ⁷, R ⁹And L ²The meaning of expression is the same.Z ¹Expression chlorine atom or bromine atoms.]

Described organic solvent has the acid amides series solvent of ketone series solvent, 1-Methyl-2-Pyrrolidone of nitro-hydrocarbon series solvent, hexone of halohydrocarbon series solvent, oil of mirbane of hydrocarbon system solvent, chlorobenzene, dichlorobenzene, chloroform of toluene, dimethylbenzene etc. etc. etc. etc. etc. for example.

The usage quantity of the compound of formula (b5) expression is with respect to 1 mole of the azo-compound of formula (b4) expression, is more than 1 mole below 8 moles, and is preferred more than 1 mole below 4 moles.

Then, adopt and above-mentioned the same method, make the azo-compound of formula (b6) expression and the compound generation esterification of formula (a5) expression, can obtain compound (Ib).

To the R in the compound of the present invention ¹For-L ²-X ¹-R ⁹And X ¹(* represents and L for the compound (I) of *-O-CO- ²Bonding position), be that the manufacture method of the compound (following be referred to as sometimes " compound (Ic) ") of formula (Ic) expression describes.

[in the formula (Ic), R ²～R ⁷, R ⁹, L ¹And L ²The meaning of expression is the same.]

By adopting and above-mentioned the same method, make the diazonium salt of formula (a2) expression and the pyridinone compounds generation diazo coupling reaction of formula (c3) expression, can make the azo-compound of formula (c4) expression.

[in formula (c3) and the formula (c4), R ²～R ⁷And L ²The meaning of expression is the same.]

Then,, the azo-compound of formula (c4) expression and the compound of formula (c5) expression are reacted, can obtain the azo-compound of formula (c6) expression by in the presence of organic solvent.Preferred 30 ℃～180 ℃ of temperature of reaction, more preferably 50 ℃～120 ℃.Preferred 1 hour～12 hours of reaction times, more preferably 1 hour～4 hours.

Employed solvent phase solvent together in the reaction of the compound of azo-compound that employed here organic solvent has for example and formula (b4) is represented and formula (b5) expression.

[in formula (c5) and the formula (c6), R ²～R ⁷, R ⁹And L ²The same meaning of expression.]

The usage quantity of the compound of formula (c5) expression is with respect to 1 mole of the azo-compound of formula (c4) expression, is more than 1 mole below 8 moles, and is preferred more than 1 mole below 4 moles.

When the compound of the azo-compound of formula (c4) expression and formula (c5) expression reacts, successfully carry out, more preferably add an acidic catalyst in order to make reaction.An acidic catalyst has the mineral acid of sulfuric acid, hydrochloric acid etc. etc. for example.

The usage quantity of these catalyzer is any, but the compound of preferably representing with respect to formula (c5) is 0.01～4 mole for 1 mole, is preferably 0.8～2 mole further.

Then, adopt and above-mentioned the same method, make the azo-compound of formula (b6) expression and the compound generation esterification of formula (a3) expression, can obtain compound (Ic).

The method that obtains target compound compound of the present invention from reaction mixture is not particularly limited, and can adopt known the whole bag of tricks.For example, preferably with reaction mixture and acid (for example acetate etc.) and water is mixed together, leaching is separated out crystallization.After preferably above-mentioned acid being mixed with aqueous acid in advance, reaction mixture is added in the above-mentioned aqueous solution.Temperature when adding reaction mixture is more than 10 ℃ below 50 ℃, and is preferred more than 20 ℃ below 50 ℃, preferred more than 20 ℃ below 30 ℃.In addition, add to reaction mixture in the aqueous acid after, preferably stirred about 0.5～2 hour down synthermal.Cleanings such as the preferred water of crystal of leaching, then dry.In addition, also can further make with extra care with known method such as recrystallizations as required.

Dyestuff of the present invention has compound (I) as effective constituent.Dyestuff of the present invention can be the dyestuff that only is made of compound (I).Dyestuff of the present invention preferably contains the compound of the present invention of the ratio of 70～100 weight %.

Compound (I) is because of the solvability excellence in organic solvent, so useful as the tinting material of photosensitive composition.

As the photosensitive composition that contains compound (I), have for example and have tinting material (following be referred to as sometimes " tinting material (A) "), resin (B), the optical polymerism compound that contains compound of the present invention

(C), the photosensitive composition of Photoepolymerizationinitiater initiater (D) and solvent (E).

Except compound (I), can also further contain dyestuff and/or the pigment different in the tinting material (A) with compound (I).

Dyestuff outside the compound (I) have for example in Colour Index (Colour Index) (The Society of Dyers and Colourists publication), be classified into solvent (Solvent), acid (Acid), alkalescence (Basic), reactive (reactive), directly (Direct), disperse the compound of (Disperse) or reduction (Vat) etc.More specifically, can exemplify the dyestuff of following Colour Index (C.I.) number, but be not limited to these.

C.I. solvent yellow 25,79, and 81,82,83,89;

C.I. turmeric yellow 7,23, and 25,42,65,76;

C.I. reactive yellow 2,76,116;

C.I. direct yellow 4,28,44,86,132;

C.I. DISPERSE YELLOW 54,76;

C.I. the solvent orange 41,54, and 56,99;

C.I. von Muller's indicator 56,74, and 95,108,149,162;

C.I. reactive orange 16;

C.I. direct orange 26;

C.I. solvent red 24,49,90,91,118,119,122,124,125,127,130,132,160,218;

C.I. Xylene Red 73,91, and 92,97,138,151,211,274,289;

C.I. acid violet 102;

C.I. solvent green 1,5;

C.I. acid green 3,5,9,25,28;

C.I. alkali green 1;

C.I. Vat green 1 etc.

Pigment has pigment dyestuff or mineral dye commonly used in the colo(u)rant dispersion resist (レ ジ ス ト) for example.Mineral dye can exemplify metal oxide or the such metallic compound of metallic complex salt, particularly, can exemplify the oxide compound or the complex metal oxides of metals such as iron, cobalt, aluminium, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony.

In addition, pigment dyestuff and mineral dye specifically can exemplify, and are classified into the compound of pigment (Pigment) in Colour Index (Colour Index) (The Society of Dyers and Colourists publication).More specifically, can exemplify the pigment of following Colour Index (C.I.) number, but be not limited to these.

C.I. Pigment Yellow 73 20,24,31,53,83,86,93,94,109,110,117,125,137,138,139,147,148,150,153,154,166,173 and 180;

C.I. pigment Orange 13,31,36,38,40,42,43,51,55,59,61,64,65 and 71;

C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,215,216,224,242,254,255 and 264;

C.I. pigment violet 14,19,23,29,32,33,36,37 and 38;

C.I. pigment Green 7,10,15,25,36 and 47 etc.

The content of tinting material (A) is preferably 5～60 mass parts with respect to 100 mass parts of the solids component in the photosensitive composition.Here, solids component is meant the total of removing the composition that desolvates in the photosensitive composition.

Preferred 3～100 quality % of the content of the compound (I) in the tinting material (A).

Compound (I), the dye well pigment different with compound (I) can be distinguished use separately, also can be used in combination more than 2 kinds.

Resin (B) is not particularly limited, and can use any resin.Resin (B) preferred bases soluble resin more preferably contains the resin by the structural unit of (methyl) vinylformic acid derivation.Here, (methyl) vinylformic acid is represented vinylformic acid and/or methacrylic acid.

Resin (B) specifically has methacrylic acid/methacrylic acid benzene methyl multipolymer, methacrylic acid/methacrylic acid benzene methyl/styrol copolymer, methacrylic acid/methacrylic acid benzene methyl/isobornyl methacrylate multipolymer, methacrylic acid/styrene/methacrylic acid benzene methyl/N-phenyl maleic anhydride contract imine copolymer, methacrylic acid/styrene/methacrylic acid glycidyl ester copolymer etc. for example.

The polystyrene conversion weight-average molecular weight of resin (B) is preferred 5,000～35,000, and more preferably 6,000～30,000.

The acid number of resin (B) is preferred 50～150, and more preferably 60～135.

The content of resin (B) is generally 7～65 mass parts with respect to solids component 100 mass parts of photosensitive composition, is preferably 13～60 mass parts.

Polymerizable compound (C) is so long as can polymeric compounds just be not particularly limited by living radical, acid etc., and wherein, described living radical is produced by light or heat effect by Photoepolymerizationinitiater initiater (D).Polymerizable compound (C) has the compound of the carbon-to-carbon unsaturated bond with polymerizability etc. for example.

Above-mentioned polymerizable compound (C) preferably has the optical polymerism compound of 3 above polymerizable groups.Here, polymerizable group is meant the group that carries out polyreaction by described living radical, acid etc.Optical polymerism compound with 3 above polymerizable groups can exemplify, pentaerythritol tetracrylate, pentaerythritol tetramethacrylate, five vinylformic acid dipentaerythritol ester, pentamethyl-vinylformic acid dipentaerythritol ester, six vinylformic acid dipentaerythritol ester, hexamethyl vinylformic acid dipentaerythritol ester etc.Above-mentioned polymerizable compound (C) can be used alone or in combination of two or more kinds.The molecular weight of polymerizable compound (C) is generally 150～800, is preferably 190～700.

The content of polymerizable compound (C) is with respect to solids component 100 mass parts of photosensitive composition, preferred 5～65 mass parts, more preferably 10～60 mass parts.

There is living radical to produce agent, acid producing agent etc. for example as above-mentioned polymerization starter (D).The living radical propellant produces living radical by the effect of light or heat.

Described living radical produces agent for example acetophenone compound of 2-methyl-2-morpholino base-1-(4-methyl sulfenyl phenyl)-1-acetone, 2-hydroxy-2-methyl-1-phenyl-1-acetone, benzyl dimethyl ketal, 2-hydroxy-2-methyl-1-(4-(2-hydroxyl-oxethyl) phenyl)-1-acetone, 1-hydroxy-cyclohexyl phenyl ketone etc. for example; 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2, the thioxanthone compound of 4-two clopenthixal ketones, 1-chloro-4-propoxy-thioxanthone etc.;

2, two (the trichloromethyl)-6-(4-p-methoxy-phenyl)-1 of 4-, 3, the 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl group naphthyl)-1 of 4-, 3, the 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl-styrene)-1,3 of 4-, the 5-triazine, 2, two (the trichloromethyl)-6-(2-(5-methyl furan-2-yl) vinyl) of 4--1,3,5-triazines, 2, two (the trichloromethyl)-6-(2-(furans-2-yl) vinyl)-1 of 4-, 3, the 5-triazine, 2, two (the trichloromethyl)-6-(2-(4-diethylamino-2-aminomethyl phenyl) vinyl)-1 of 4-, 3, the 5-triazine, 2, two (the trichloromethyl)-6-(2-(3, the 4-Dimethoxyphenyl) vinyl)-1 of 4-, 3, the triaizine compounds of 5-triazine etc.;

2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide, 2,2 '-two (Chloro-O-Phenyl)-4,4 ', 5,5 '-tetraphenyl-1,2 '-two imidazoles, 10-butyl-2-chloro-acridine ketone, 2-ethyl-anthraquinone, phenmethyl, 9,10-phenanthrenequione, camphorquinone, phenyl glyoxalic acid methylester, two cyclopentadiene titanium compounds etc.

Described acid producing agent can examples example such as the salt of triphenylsulfonium tosilate, triphenylsulfonium hexafluoro antimonate, 4-acetoxyl group phenyl dimethyl sulfonium tosilate, phenylbenzene iodine tosilate, biphenyl iodine hexafluoro antimonate etc., perhaps oil of mirbane methyl tosilate class, st-yrax tosic acid salt etc.

Above-mentioned Photoepolymerizationinitiater initiater (D) can be used alone or in combination of two or more kinds.

The content of Photoepolymerizationinitiater initiater (D) is with respect to the total amount of resin (B) and optical polymerism compound (C), preferred 0.1～30 quality %, more preferably 1～20 quality %.The content of Photoepolymerizationinitiater initiater in above-mentioned scope, highly sensitiveization, the time shutter shortens, productivity improves, and is therefore comparatively desirable.

Solvent (E) has for example ether, ketone, alcohol, ester, acid amides etc. for example.

Described ether for example has for example, tetrahydrofuran (THF), tetrahydropyrans, 1, the 4-diox, the glycol monomethyl methyl ether, ethylene glycol monomethyl ether, the glycol monomethyl propyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, TC, the Diethylene Glycol single-butyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, the Diethylene Glycol dipropyl ether, the Diethylene Glycol dibutyl ether, propylene glycol monomethyl ether, propylene glycol list ethyl ether, propylene glycol list propyl ether, propylene glycol monomethyl ether, propylene glycol list ethyl ether acetic ester, propylene glycol list propyl ether acetic ester, the ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, the TC acetic ester, Diethylene Glycol single-butyl ether acetic ester etc.

Above-mentioned ketone can exemplify acetone, 2-butanone, 2-heptanone, 3-heptanone, dipropyl ketone, 4-methyl-2 pentanone, 4-hydroxy-4-methyl-2 pentanone, cyclopentanone, pimelinketone etc.

Described alcohol has hexanol, hexalin, ethylene glycol, glycerine etc. for example.

Described ester has ethyl acetate for example, n-butyl acetate, isobutyl acetate, the formic acid pentyl ester, Isoamyl Acetate FCC, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, n-Butyl lactate, methoxy menthyl acetate, the methoxyacetic acid ethyl ester, the methoxyacetic acid butyl ester, ethoxy acetate, ethoxy ethyl acetate, 3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, the 3-ethoxyl ethyl propionate, 2-methoxypropionic acid methyl esters, 2-methoxy propyl acetoacetic ester, 2-methoxy propyl propyl propionate, 2-ethoxy-propionic acid methyl esters, the 2-ethoxyl ethyl propionate, 2-methoxyl group-2 Methylpropionic acid methyl esters, 2-oxyethyl group-2 Methylpropionic acid ethyl ester, Pyruvic Acid Methyl ester, Pyruvic Acid Ethyl ester, Propyl pyruvate, methyl acetoacetate, methyl aceto acetate, acetate-3-methoxyl group butyl ester, acetate-3-methyl-3-methoxyl group butyl ester, gamma-butyrolactone etc.

Above-mentioned acid amides has N for example, N '-dimethyl formamide, N,N-dimethylacetamide, N-Methyl pyrrolidone etc.

These solvents can use separately also and can be used in combination more than 2 kinds.

The content of solvent in the photosensitive composition (E) in photosensitive composition, preferred 70～95 quality %, more preferably 75～90 quality %.

Photosensitive composition of the present invention can contain the various additive of tensio-active agent, weighting agent, other macromolecular compounds, adhesion promotor, antioxidant, UV light absorber, photostabilizer, chain-transfer agent etc. as required.

Compound of the present invention is useful as dyestuff.From the solvability organic solvent high aspect, especially useful as the employed dyestuff of colour filter of the display unit of liquid crystal indicator etc.

In addition, above-mentioned photosensitive composition can be used to have colour filter in known manner as the display unit (for example, known liquid crystal indicator, organic El device etc.) of the part of this component parts, the machine that is associated with the various rendered image of solid-state image pickup etc.

[embodiment]

Next exemplify embodiment etc., the present invention is carried out further specific description.

In embodiment, reference example and the comparative example, the % of expression content or usage quantity and part all are to be benchmark with the quality as long as there is not special record.

Among the following embodiment, the structure of compound NMR (JMM-ECA-500; NEC (strain) system) confirms.

Embodiment 1

After in 18.2 parts of 5-nitro anthranilic acids (Tokyo change into industry (strain) system), adding 80 parts of entry, add 0.4 part in sodium hydroxide, make it dissolving.Add 19.7 parts of 35% sodium nitrite in aqueous solution down ice-cooled, then little by little add 26.2 parts of 35% hydrochloric acid, make it dissolving, stirred 2 hours, obtain containing the suspension liquid of diazonium salt.

On the other hand, with 24.4 parts of mixing of 26.0 parts of methyl aceto acetates (Tokyo changes into industry (strain) system), 20.8 parts of methyl-cyanacetates (the Tokyo system of changing into) and 2-monoethanolamine (with the pure pharmaceutical worker's industry of light (strain) system), stirred 24 hours down at 95 ℃.Behind above-mentioned reaction solution cool to room temperature, add in the mixed solution of 35 parts of 304 parts in water and 35% hydrochloric acid, at room temperature stirred 1 hour.The crystal that leaching is separated out as residue after, carry out drying, obtain 20.4 parts of the compounds of formula (d1) expression.

Then, make 20.4 parts of the compounds of formula (d1) expression outstanding turbid in 100 parts in water, use sodium hydroxide that pH is adjusted to 9.0.Spend 15 minutes with pump and drip the described suspension liquid that contains diazonium salt inward.After dripping end, restir 30 minutes obtains the xanchromatic suspension liquid.Stirred 1 hour.The yellow solid that filtration is obtained under reduced pressure 60 ℃ dry down, obtain 38.7 parts of the compounds shown in the formula (d2).

Compound shown in the adding formula (d3) is 25.7 parts in 30.1 parts of the compounds of formula (d2) expression, in the solvent of N-Methyl pyrrolidone, stirs 3 hours down at 70 ℃.After reaction finishes, use water saturation, obtain 37.0 parts of the compounds that formula (d4) represents.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (d4) expression 〉

¹H-NMR：1.10(3H，t)，2.49(2H，t)，2.49(2H，t)，2.56(3H，s)，3.96(2H，q)，4.10(2H，t)，4.23(2H，t)，8.16(1H，d)，8.46(1H，dd)，8.70(1H，d)，14.50(1H，bs)，15.56(1H，s)。

Add 1.89 parts of (±)-10-camphorsulfonic acids, N in 30.2 parts of the compounds of formula (d4) expression, 450 parts of 3.25 parts of N-dimethyl-4-aminopyridines, 15.2 parts of 2 and chloroforms stir down at 5 ℃.The limit keeps 5 ℃ temperature, and limit dropping in this suspension liquid makes 16.4 parts of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochlorides be dissolved in the solution that obtains behind 197 parts of the chloroforms.After dripping end, at room temperature stirred 5 hours.After reaction finishes, clean with 1N hydrochloric acid and saturated aqueous common salt.Take out organic layer with separating funnel, add sal epsom and make it dry, filter.With Rotary Evaporators to filtrate distill remove desolvate after, at 60 ℃ of following drying under reduced pressure, obtain 29.0 parts of the compounds of formula (I-45) expression.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (I-45) expression 〉

¹H-NMR：1.10(3H，t)，2.49(2H，t)，2.49(2H，t)，2.56(3H，s)，2.83(2H，m)，3.45(1H，m)，3.97(2H，q)，4.11(2H，t)，4.23(2H，t)，4.45(2H，m)，8.21(1H，d)，8.51(1H，dd)，8.74(1H，d)，15.03(1H)

The compound 0.10g of formula (I-45) expression that obtains is dissolved in the dimethyl formamide, and constant volume is 250cm ³, with 2cm wherein ³With the ethyl lactate dilution, making volume is 100cm ³(concentration: 0.0080g/L), use ultraviolet-visible pectrophotometer (V-650DS; Japan's beam split (strain) system) (quartz container, optical length; 1cm), measure absorption spectrum.This compound presents bright-coloured yellow under the condition of λ max=435nm, molar absorptivity shows higher value, is 48000.

Comparative example 1

Use the 5-nitro anthranilic acid among the amino terephthaldehyde's acid substitution of the 2-embodiment 1, the compound of use formula (e1) expression replaces the compound of formula (d1) expression, and in addition, other are the same with embodiment 1, obtain the compound of formula (i) expression.

The compound 0.35g of formula (i) expression that obtains is dissolved in the dimethyl formamide, and constant volume is 250cm ³, with 2cm wherein ³With the ethyl lactate dilution, making volume is 100cm ³(concentration: 0.028g/L), use ultraviolet-visible pectrophotometer (V-650DS; Japan's beam split (strain) system) (quartz container, optical length; 1cm), measure absorption spectrum.This compound is under the condition of λ max=440nm, and molar absorptivity reaches 42000.

(deliquescent evaluation)

The compound that following embodiment of obtaining 1 and comparative example 1 obtain propylene glycol monomethyl ether (below, abbreviate PGMEA as), propylene glycol monomethyl ether (below, abbreviate PGME as), ethyl lactate (below, abbreviate EL as), the solubleness in the N-Methyl pyrrolidone (below, abbreviate NMP as).

In the 50ml sample hose, with compound and above-mentioned solvent, then, fill in tight sample hose in following ratio, vibrated 3 minutes with the ultra-sonic oscillation machine down at 30 ℃.Then, at room temperature place 30 minutes after, filter this residue of visual observation.In the time of can not confirming insolubles and be residue, judge favorable solubility, note does zero in table 2, in the time of can confirming insolubles, judges that solvability is bad, in table 2 note do *.The result is shown in the table 2.

0.5% compound 0.01g, solvent 2g

1% compound 0.01g, solvent 1g

3% compound 0.03g, solvent 1g

[table 2]

Reference example 1

(preparation of photosensitive composition)

(I-45) 20 parts of tinting material: embodiment 1 synthetic compounds

(B-1) resin: methacrylic acid/methacrylic acid benzylester multipolymer (mol ratio; 30/70; Weight-average molecular weight 10700, acid number 70mgKOH/g) 70 parts

(C-1) polymerizable compound: 30 parts of six vinylformic acid dipentaerythritol ester (Japanese chemical drug society system)

(D-1) Photoepolymerizationinitiater initiater: benzyl dimethyl ketal (イ Le ガ キ ユ ア 651; チ バ ジ ヤ パ Application society system) 15 part

(E-1) solvent: N, 680 parts of dinethylformamides

Mix above-mentioned substance, obtain photosensitive composition.

(making of colour filter)

At the photosensitive composition that coating on glass as above obtains, make the volatile component volatilization with spin-coating method.After the cooling, figuratum silica glass system photomask of apparatus and exposure machine carry out rayed.After the rayed, develop, use oven heat, obtain colour filter with potassium hydroxide aqueous solution.

Embodiment 2

After in 18 parts of 4-nitro anthranilic acids (Tokyo change into industry (strain) system), adding 80 parts of entry, add 0.4 part in sodium hydroxide, make it dissolving.Add 19.8 parts of 35% sodium nitrite in aqueous solution down ice-cooled, then little by little add 26.1 parts of 35% hydrochloric acid, make it dissolving, stirred 2 hours, obtain containing the suspension liquid of diazonium salt.Then, 20.3 parts of the compounds of formula (d1) expression are suspended in 100 parts in the water, use sodium hydroxide that pH is adjusted to 9.0.Spend 15 minutes with pump and drip the described suspension liquid that contains diazonium salt inward.After dripping end, restir 30 minutes obtains the xanchromatic suspension liquid.Stirred 1 hour.The yellow solid that filtration is obtained under reduced pressure 60 ℃ dry down, obtain 38.4 parts of the compounds shown in the formula (d5).

The evaluation of the compound of＜formula (d5) expression 〉

¹H-NMR：2.38(3H，s)，3.53(2H，dd)，3.89(2H，t)，5.23(1H，bs)，7.83(1H，dd)，8.04(1H，d)，8.11(1H，d)，16.56(1H，s).

Compound shown in the adding formula (d3) is 25.6 parts in 30 parts of the compounds of formula (d5) expression, in the solvent of N-Methyl pyrrolidone, stirs 3 hours down at 70 ℃.After reaction finishes, use water saturation, obtain 36.9 parts of the compounds that formula (d6) represents.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (d6) expression 〉

¹H-NMR：1.11(3H，t)，2.48(2H，t)，2.48(2H，t)，2.55(3H，s)，3.95(2H，q)，4.09(2H，t)，4.22(2H，t)，7.83(1H，dd)，8.04(1H，d)，8.11(1H，d)，14.52(1H，bs)，15.54(1H，s).

Add 1.89 parts of (±)-10-camphorsulfonic acids, N in 30.1 parts of the compounds of formula (d6) expression, 450 parts of 3.20 parts of N-dimethyl-4-aminopyridines, 15.3 parts of 2 and chloroforms stir down at 5 ℃.The limit keeps 5 ℃ temperature, and limit dropping in this suspension liquid makes 16.4 parts of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochlorides be dissolved in the solution that obtains behind 197 parts of the chloroforms.After dripping end, at room temperature stirred 5 hours.After reaction finishes, clean with 1N hydrochloric acid and saturated aqueous common salt.Take out organic layer with separating funnel, add sal epsom and make it dry, filter.With Rotary Evaporators to filtrate distill remove desolvate after, at 60 ℃ of following drying under reduced pressure, obtain 29.1 parts of the compounds of formula (I-46) expression.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (I-46) expression 〉

¹H-NMR：1.10(3H，t)，2.49(2H，t)，2.49(2H，t)，2.56(3H，s)，2.83(2H，m)，3.45(1H，m)，3.97(2H，q)，4.11(2H，t)，4.23(2H ，t)，4.45(2H，m)，7.83(1H，dd)，8.04(1H，d)，8.11(1H，d)，15.10(1H).

The compound 0.1g of formula (I-46) expression that obtains is dissolved in the dimethyl formamide, and constant volume is 250cm ³, with 2cm wherein ³With the ethyl lactate dilution, making volume is 100cm ³(concentration: 0.0080g/L), use ultraviolet-visible pectrophotometer (V-650DS; Japan's beam split (strain) system) (quartz container, optical length; 1cm), measure absorption spectrum.This compound presents bright-coloured yellow under the condition of λ max=425nm, molar absorptivity shows higher value, is 48000.

Embodiment 3

Compound shown in the adding formula (d7) is 25.4 parts in 30.2 parts of the compounds of formula (d5) expression, in the solvent of N-Methyl pyrrolidone, stirs 3 hours down at 70 ℃.After reaction finishes, use water saturation, obtain 37.3 parts of the compounds that formula (d8) represents.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (d8) expression 〉

¹H-NMR：0.75(3H)，0.77(3H)，1.08(2H)，1.18(2H)，1.37(2H)，1.42(2H)，2.16(1H)，2.55(3H)，4.11(2H)，4.23(2H)，7.83(1H)，8.04(1H)，8.11(1H)，14.50(1H)，15.03(1H).

Add 1.89 parts of (±)-10-camphorsulfonic acids, N in 30 parts of the compounds of formula (d8) expression, 450 parts of 3.26 parts of N-dimethyl-4-aminopyridines, 15.4 parts of 2 and chloroforms stir down at 5 ℃.The limit keeps 5 ℃ temperature, and limit dropping in this suspension liquid makes 17 parts of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochlorides be dissolved in the solution that obtains behind 197 parts of the chloroforms.After dripping end, at room temperature stirred 5 hours.After reaction finishes, clean with 1N hydrochloric acid and saturated aqueous common salt.Take out organic layer with separating funnel, add sal epsom and make it dry, filter.With Rotary Evaporators to filtrate distill remove desolvate after, at 60 ℃ of following drying under reduced pressure, obtain 28.4 parts of the compounds of formula (I-86) expression.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (I-86) expression 〉

¹H-NMR：0.75(3H)，0.77(3H)，1.08(2H)，1.18(2H)，1.37(2H)，1.42(2H)，2.16(1H)，2.55(3H)，2.83(2H)，3.45(1H)，4.11(2H)，4.23(2H)，4.45(2H)，7.83(1H)，8.04(1H)，8.11(1H)，15.03(1H).

The compound 0.10g of formula (I-86) expression that obtains is dissolved in the dimethyl formamide, and constant volume is 250cm ³, with 2cm wherein ³With the ethyl lactate dilution, making volume is 100cm ³(concentration: 0.0080g/L), use ultraviolet-visible pectrophotometer (V-650DS; Japan's beam split (strain) system) (quartz container, optical length; 1cm), measure absorption spectrum.This compound presents bright-coloured yellow under the condition of λ max=425nm, molar absorptivity shows higher value, is 48000.

Embodiment 4

Compound shown in the adding formula (d7) is 25.2 parts in 30.0 parts of the compounds of formula (d2) expression, in the solvent of N-Methyl pyrrolidone, stirs 3 hours down at 70 ℃.After reaction finishes, use water saturation, obtain 36.9 parts of the compounds that formula (d9) represents.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (d9) expression 〉

¹H-NMR：0.75(3H)，0.77(3H)，1.08(2H)，1.18(2H)，1.37(2H)，1.42(2H)，2.16(1H)，2.55(3H)，4.11(2H)，4.23(2H)，8.22(1H)，8.50(1H)，8.75(1H)，14.50(1H)，15.03(1H).

Add 1.89 parts of (±)-10-camphorsulfonic acids, N in 30.1 parts of the compounds of formula (d9) expression, 450 parts of 3.27 parts of N-dimethyl-4-aminopyridines, 15.4 parts of 2 and chloroforms stir down at 5 ℃.The limit keeps 5 ℃ temperature, and limit dropping in this suspension liquid makes 17.1 parts of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochlorides be dissolved in the solution that obtains behind 197 parts of the chloroforms.After dripping end, at room temperature stirred 5 hours.After reaction finishes, clean with 1N hydrochloric acid and saturated aqueous common salt.Take out organic layer with separating funnel, add sal epsom and make it dry, filter.With Rotary Evaporators to filtrate distill remove desolvate after, at 60 ℃ of following drying under reduced pressure, obtain 28.4 parts of the compounds of formula (I-85) expression.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (I-85) expression 〉

¹H-NMR：0.75(3H)，0.77(3H)，1.08(2H)，1.18(2H)，1.37(2H)，1.42(2H)，2.16(1H)，2.55(3H)，2.83(2H)，3.45(1H)，4.11(2H)，4.23(2H)，4.45(2H)，8.20(1H)，8.53(1H)，8.76(1H)，15.05(1H).

The compound 0.10g of formula (I-85) expression that obtains is dissolved in the dimethyl formamide, and constant volume is 250cm ³, with 2cm wherein ³With the ethyl lactate dilution, making volume is 100cm ³(concentration: 0.008g/L), use ultraviolet-visible pectrophotometer (V-650DS; Japan's beam split (strain) system) (quartz container, optical length; 1cm), measure absorption spectrum.This compound presents bright-coloured yellow under the condition of λ max=435nm, molar absorptivity shows higher value, is 48000.

Embodiment 5

After in 18.2 parts of 5-nitro anthranilic acids (Tokyo change into industry (strain) system), adding 80 parts of entry, add 0.4 part in sodium hydroxide, make it dissolving.Add 19.7 parts of 35% sodium nitrite in aqueous solution down ice-cooled, then little by little add 26.2 parts of 35% hydrochloric acid, make it dissolving, stirred 2 hours, obtain containing the suspension liquid of diazonium salt.

On the other hand, with 30.0 parts of mixing of 26.0 parts of methyl aceto acetates (Tokyo changes into industry (strain) system), 20.8 parts of methyl-cyanacetates (the Tokyo system of changing into) and 2-monoethanolamine (with the pure pharmaceutical worker's industry of light (strain) system), stirred 24 hours down at 95 ℃.Behind above-mentioned reaction solution cool to room temperature, add in the mixed solution of 35 parts of 304 parts in water and 35% hydrochloric acid, at room temperature stirred 1 hour.The crystal that leaching is separated out as residue after, carry out drying, obtain 21.9 parts of the compounds of formula (d10) expression.

The evaluation of the compound of＜formula (d10) expression 〉

¹H-NMR：1.10(3H，t)，2.49(2H，t)，2.49(2H，t)，2.56(3H，s)，3.96(2H，q)，4.10(2H，t)，4.23(2H，t)，8.16(1H，d)，8.46(1H，dd)，8.70(1H，d)，14.50(1H，bs)，15.56(1H，s)

Then, make 21.9 parts of the compounds of formula (d10) expression outstanding turbid in 100 parts in water, use sodium hydroxide that pH is adjusted to 9.0.Spend 15 minutes with pump and drip the described suspension liquid that contains diazonium salt inward.After dripping end, restir 30 minutes obtains the xanchromatic suspension liquid.Stirred 1 hour.The yellow solid that filtration is obtained under reduced pressure 60 ℃ dry down, obtain 42.3 parts of the compounds shown in the formula (d11).

The evaluation of the compound of＜formula (d11) expression 〉

¹H-NMR：1.12(3H)，2.38(3H)，3.53(2H)，3.89(1H)，5.23(1H)，8.21(1H)，8.52(1H)，8.75(1H)，15.44(1H).

Compound shown in the adding formula (d3) is 25.7 parts in 32.9 parts of the compounds of formula (d11) expression, in the solvent of N-Methyl pyrrolidone, stirs 3 hours down at 70 ℃.After reaction finishes, use water saturation, obtain 38.0 parts of the compounds that formula (d12) represents.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (d12) expression 〉

¹H-NMR：1.10(3H)，1.12(3H)，2.49(2H)，2.49(2H)，2.56(3H)，3.96(2H)，4.10(2H)，4.23(1H)，8.16(1H)，8.46(1H)，8.70(1H)，14.50(1H)，15.56(1H)。

Add 1.89 parts of (±)-10-camphorsulfonic acids, N in 31.0 parts of the compounds of formula (d12) expression, 450 parts of 3.25 parts of N-dimethyl-4-aminopyridines, 15.2 parts of 2 and chloroforms stir down at 5 ℃.The limit keeps 5 ℃ temperature, and limit dropping in this suspension liquid makes 16.4 parts of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochlorides be dissolved in the solution that obtains behind 197 parts of the chloroforms.After dripping end, at room temperature stirred 5 hours.After reaction finishes, clean with 1N hydrochloric acid and saturated aqueous common salt.Take out organic layer with separating funnel, add sal epsom and make it dry, filter.With Rotary Evaporators to filtrate distill remove desolvate after, at 60 ℃ of following drying under reduced pressure, obtain 29.7 parts of the compounds of formula (I-65) expression.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (I-65) expression 〉

¹H-NMR：1.10(3H)，1.12(3H)，2.49(2H)，2.49(2H)，2.56(3H)，2.83(2H)，3.45(1H)，3.97(2H)，4.11(2H)，4.23(1H)，4.45(2H)，8.21(1H)，8.51(1H)，8.74(1H)，15.50(1H)。

The compound 0.10g of formula (I-65) expression that obtains is dissolved in the dimethyl formamide, and constant volume is 250cm ³, with 2cm wherein ³With the ethyl lactate dilution, making volume is 100cm ³(concentration: 0.008g/L), use ultraviolet-visible pectrophotometer (V-650DS; Japan's beam split (strain) system) (quartz container, optical length; 1cm), measure absorption spectrum.This compound presents bright-coloured yellow under the condition of λ max=434nm, molar absorptivity shows higher value, is 48000.

Embodiment 6

After in 18.3 parts of 4-nitro anthranilic acids (Tokyo change into industry (strain) system), adding 80 parts of entry, add 0.4 part in sodium hydroxide, make it dissolving.Add 19.7 parts of 35% sodium nitrite in aqueous solution down ice-cooled, then little by little add 26.2 parts of 35% hydrochloric acid, make it dissolving, stirred 2 hours, obtain containing the suspension liquid of diazonium salt.

Then, 21.9 parts of the compounds of formula (d10) expression are suspended in 100 parts in the water, use sodium hydroxide that pH is adjusted to 9.0.Spend 15 minutes with pump and drip the described suspension liquid that contains diazonium salt inward.After dripping end, restir 30 minutes obtains the xanchromatic suspension liquid.Stirred 1 hour.The yellow solid that filtration is obtained under reduced pressure 60 ℃ dry down, obtain 42.5 parts of the compounds shown in the formula (d13).

The evaluation of the compound of＜formula (d13) expression 〉

¹H-NMR：1.12(3H)，2.38(3H)，3.53(2H)，3.89(1H)，5.23(1H)，7.83(1H)，8.04(1H)，8.11(1H)，15.95(1H).

Compound shown in the adding formula (d3) is 25.7 parts in 32.9 parts of the compounds of formula (d13) expression, in the solvent of N-Methyl pyrrolidone, stirs 3 hours down at 70 ℃.After reaction finishes, use water saturation, obtain 36.9 parts of the compounds that formula (d14) represents.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (d14) expression 〉

¹H-NMR：1.10(3H)，1.12(3H)，2.49(2H)，2.49(2H)，2.56(3H)，3.96(2H)，4.10(2H)，4.23(1H)，7.83(1H)，8.04(1H)，8.11(1H)，14.50(1H)，15.56(1H)。

Add 1.89 parts of (±)-10-camphorsulfonic acids, N in 30.9 parts of the compounds of formula (d14) expression, 450 parts of 3.25 parts of N-dimethyl-4-aminopyridines, 15.2 parts of 2 and chloroforms stir down at 5 ℃.The limit keeps 5 ℃ temperature, and limit dropping in this suspension liquid makes 16.4 parts of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochlorides be dissolved in the solution that obtains behind 197 parts of the chloroforms.After dripping end, at room temperature stirred 5 hours.After reaction finishes, clean with 1N hydrochloric acid and saturated aqueous common salt.Take out organic layer with separating funnel, add sal epsom and make it dry, filter.With Rotary Evaporators to filtrate distill remove desolvate after, at 60 ℃ of following drying under reduced pressure, obtain 28.7 parts of the compounds of formula (I-66) expression.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (I-66) expression 〉

¹H-NMR：1.10(3H)，1.12(3H)，2.49(2H)，2.49(2H)，2.56(3H)，2.83(2H)，3.45(1H)，3.97(2H)，4.11(2H)，4.23(1H)，4.45(2H)，7.83(1H)，8.04(1H)，8.11(1H)，15.80(1H).

The compound 0.10g of formula (I-66) expression that obtains is dissolved in the dimethyl formamide, and constant volume is 250cm ³, with 2cm wherein ³With the ethyl lactate dilution, making volume is 100cm ³(concentration: 0.008g/L), use ultraviolet-visible pectrophotometer (V-650DS; Japan's beam split (strain) system) (quartz container, optical length; 1cm), measure absorption spectrum.This compound presents bright-coloured yellow under the condition of λ max=424nm, molar absorptivity shows higher value, is 48000.

Embodiment 7

Compound shown in the adding formula (d7) is 27.0 parts in 30.5 parts of the compounds of formula (d13) expression, in the solvent of N-Methyl pyrrolidone, stirs 3 hours down at 70 ℃.After reaction finishes, use water saturation, obtain 37.2 parts of the compounds that formula (d15) represents.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (d15) expression 〉

¹H-NMR：0.75(3H)，0.77(3H)，1.08(2H)，1.14(3H)，1.18(2H)，1.37(2H)，1.42(2H)，2.16(1H)，2.55(3H)，4.11(2H)，4.23(1H)，7.83(1H)，8.04(1H)，8.11(1H)，14.48(1H)，15.01(1H).

Add 1.89 parts of (±)-10-camphorsulfonic acids, N in 30.8 parts of the compounds of formula (d15) expression, 450 parts of 3.26 parts of N-dimethyl-4-aminopyridines, 15.4 parts of 2 and chloroforms stir down at 5 ℃.The limit keeps 5 ℃ temperature, and limit dropping in this suspension liquid makes 17 parts of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochlorides be dissolved in the solution that obtains behind 197 parts of the chloroforms.After dripping end, at room temperature stirred 5 hours.After reaction finishes, clean with 1N hydrochloric acid and saturated aqueous common salt.Take out organic layer with separating funnel, add sal epsom and make it dry, filter.With Rotary Evaporators to filtrate distill remove desolvate after, at 60 ℃ of following drying under reduced pressure, obtain 28.3 parts of the compounds of formula (I-125) expression.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (I-125) expression 〉

¹H-NMR：0.75(3H)，0.77(3H)，1.08(2H)，1.15(3H)，1.18(2H)，1.37(2H)，1.42(2H)，2.16(1H)，2.55(3H)，2.83(2H)，3.45(1H)，4.11(2H)，4.23(1H)，4.45(2H)，7.83(1H)，8.04(1H)，8.11(1H)，15.03(1H).

The compound 0.10g of formula (I-125) expression that obtains is dissolved in the dimethyl formamide, and constant volume is 250cm ³, with 2cm wherein ³With the ethyl lactate dilution, making volume is 100cm ³(concentration: 0.008g/L), use ultraviolet-visible pectrophotometer (V-650DS; Japan's beam split (strain) system) (quartz container, optical length; 1cm), measure absorption spectrum.This compound presents bright-coloured yellow under the condition of λ max=425nm, molar absorptivity shows higher value, is 48000.

Embodiment 8

Compound shown in the adding formula (d7) is 26.8 parts in 30.6 parts of the compounds of formula (d11) expression, in the solvent of N-Methyl pyrrolidone, stirs 3 hours down at 70 ℃.After reaction finishes, use water saturation, obtain 37.1 parts of the compounds that formula (d16) represents.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (d16) expression 〉

¹H-NMR：0.75(3H)，0.77(3H)，1.08(2H)，1.14(3H)，1.18(2H)，1.37(2H)，1.42(2H)，2.16(1H)，2.55(3H)，4.11(2H)，4.23(1H)，8.21(1H)，8.51(1H)，8.74(1H)，14.48(1H)，15.01(1H).

Add 1.89 parts of (±)-10-camphorsulfonic acids, N in 30.6 parts of the compounds of formula (d16) expression, 450 parts of 3.26 parts of N-dimethyl-4-aminopyridines, 15.4 parts of 2 and chloroforms stir down at 5 ℃.The limit keeps 5 ℃ temperature, and limit dropping in this suspension liquid makes 17 parts of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochlorides be dissolved in the solution that obtains behind 197 parts of the chloroforms.After dripping end, at room temperature stirred 5 hours.After reaction finishes, clean with 1N hydrochloric acid and saturated aqueous common salt.Take out organic layer with separating funnel, add sal epsom and make it dry, filter.With Rotary Evaporators to filtrate distill remove desolvate after, at 60 ℃ of following drying under reduced pressure, obtain 28.6 parts of the compounds of formula (I-21) expression.With ¹H-NMR confirms structure.

The evaluation of the compound of＜formula (I-21) expression 〉

¹H-NMR：0.75(3H)，0.77(3H)，1.08(2H)，1.15(3H)，1.18(2H)，1.37(2H)，1.42(2H)，2.16(1H)，2.55(3H)，2.83(2H)，3.45(1H)，4.11(2H)，4.23(1H)，4.45(2H)，8.23(1H)，8.55(1H)，8.78(1H)，15.24(1H).

The compound 0.10g of formula (I-21) expression that obtains is dissolved in the dimethyl formamide, and constant volume is 250cm ³, with 2cm wherein ³With the ethyl lactate dilution, making volume is 100cm ³(concentration: 0.008g/L), use ultraviolet-visible pectrophotometer (V-650DS; Japan's beam split (strain) system) (quartz container, optical length; 1cm), measure absorption spectrum.This compound presents bright-coloured yellow under the condition of λ max=433nm, molar absorptivity shows higher value, is 48000.

Adopt method similarly to Example 1, the solvability of embodiment 2～8 resulting compounds is estimated.The results are shown in table 3.

[table 3]

From the result of table 2 and table 3 as can be known, the compound of embodiment demonstrates high solubleness for organic solvent.

Reference example 2

Except embodiment 1 synthetic compound is replaced to the embodiment 2 synthetic compounds, other are the same with reference example 1, obtain photosensitive composition and colour filter.

Reference example 3

Except embodiment 1 synthetic compound is replaced to the embodiment 3 synthetic compounds, other are the same with reference example 1, obtain photosensitive composition and colour filter.

Reference example 4

Except embodiment 1 synthetic compound is replaced to the embodiment 4 synthetic compounds, other are the same with reference example 1, obtain photosensitive composition and colour filter.

Reference example 5

Except embodiment 1 synthetic compound is replaced to the embodiment 5 synthetic compounds, other are the same with reference example 1, obtain photosensitive composition and colour filter.

Reference example 6

Except embodiment 1 synthetic compound is replaced to the embodiment 6 synthetic compounds, other are the same with reference example 1, obtain photosensitive composition and colour filter.

Reference example 7

Except embodiment 1 synthetic compound is replaced to the embodiment 7 synthetic compounds, other are the same with reference example 1, obtain photosensitive composition and colour filter.

Reference example 8

Except embodiment 1 synthetic compound is replaced to the embodiment 8 synthetic compounds, other are the same with reference example 1, obtain photosensitive composition and colour filter.

The photosensitive composition that contains this compound, the few foreign of generation can be made high-quality colour filter.

Utilizability on the industry

The solvability excellence of compound of the present invention in organic solvent as the employed dyestuff of the colour filter of display unit such as liquid crystal indicator, is excellent.

Claims (7)

1. the compound shown in the formula (I),

In the formula (I), R ¹The expression hydrogen atom maybe can have the monovalence alkyl of substituent carbonatoms 1～30, and this alkyl is contained-CH ₂-can by-O-or-CO-replaces,

R ²Expression hydrogen atom, cyano group or formamyl,

R ³The alkyl of expression carbonatoms 1～4, the contained hydrogen atom of this alkyl can be replaced by halogen atom,

R ⁴～R ⁸The group of alkoxyalkyl, hydroxyl, cyano group, nitro, halogen atom or formula (Ia) expression of representing alkoxyl group, the carbonatoms 2～8 of alkyl, the carbonatoms 1～8 of hydrogen atom, carbonatoms 1～8 independently of each other, group shown at least one expression (Ia)

In the formula (Ia), L ¹The alkylidene group of expression carbonatoms 1～8.

2. as the compound of claim 1 record, R ⁸It is the group shown in the formula (Ia).

3. as the compound of claim 1 record, R ¹Be-L ²-X ¹-R ⁹The group of expression,

Wherein, L ²The alkylidene group of expression carbonatoms 1～8, X ¹Expression-CO-O-, R ⁹The univalent aliphatic series alkyl of expression hydrogen atom or carbonatoms 1～20, this aliphatic alkyl is contained-CH ₂-can by-O-or-CO-replaces.

4. as the compound of claim 1 record, R ¹Be-L ²-X ¹-L ³-X ²-R ¹⁰The group of expression,

Wherein, L ²And X ¹Meaning the same, L ³The alkylidene group of expression carbonatoms 1～8, X ²Expression-CO-O-, R ¹⁰Expression hydrogen atom, methyl or ethyl.

5. as claim 3 or 4 described compounds, X ¹Be *-O-CO-,

Wherein, * represents and L ²Bonding position.

6. as the compound of claim 1 record, R ⁴～R ⁸In have one at least for nitro.

7. dyestuff is an effective constituent with the compound of claim 1 record.