CN101598897A

CN101598897A - Cured composition for color

Info

Publication number: CN101598897A
Application number: CNA2009101415970A
Authority: CN
Inventors: 秋山裕次; 小山惠范
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2008-06-03
Filing date: 2009-06-01
Publication date: 2009-12-09
Anticipated expiration: 2029-06-01
Also published as: TW201001067A; JP5910691B2; JP2010168531A; JP2015057654A; KR20090126192A; TWI456345B; CN103869613B; CN103869613A; JP6028774B2; JP5931319B2; CN101598897B; KR101741653B1; JP2015061907A

Abstract

Cured composition for color is provided, contains (A) colorant and (B) polymerizable compound, (A) colorant is the pigment that contains formula (1) expression and the colorant of weld.[in the formula (1), A ¹～A ¹⁶Independent separately expression hydrogen atom, chlorine atom or bromine atoms.]

Description

Cured composition for color

Technical field

The present invention is about the cured composition for color of the color filter that is used to form LCD panel etc.

Background technology

Having used the display device of color filter, is to show portrait by the light that sees through color filter, therefore, compares with self-luminous display such as plasma display, has the low problem of brightness, in order to obtain bright bright-coloured portrait, seeks the color filter of high brightness.

[prior art document]

[non-patent literature]

[non-patent literature 1] " これ Ga デイスプレイ overall picture だ! " P114 (people such as spring Gu She work; かん I is published distribution on April 18th, 2005)

Summary of the invention

The cured composition for color that the purpose of this invention is to provide the color filter that can form brightness and contrast excellence.

People of the present invention by having found cured composition for color after the research with keen determination, have finished the present invention for solving above-mentioned problem.

That is, the invention provides following invention.

1. cured composition for color contains (A) colorant and (B) polymerizable compound, and (A) colorant is the pigment that contains formula (1) expression and the colorant of weld.

[in the formula (1), A ¹～A ¹⁶Independent separately expression hydrogen atom, chlorine atom or bromine atoms.]

2. as 1 described cured composition for color, wherein, weld is to contain the weld that is selected from least a kind of dyestuff in barbiturates azo based dye, pyridone azo based dye, pyrazolone azo based dye, Kui phthalein ketone based dye and the anthocyanin based dye.

3. as 1 or 2 described cured composition for color, wherein, barbiturates azo based dye is the dyestuff of formula (2) expression.

[in the formula (2), T ¹And T ²Independent separately expression oxygen atom or sulphur atom.

R ³¹～R ³⁴Independent separately expression hydrogen atom, can contain substituent carbon number 1～10 aliphatic alkyl, can contain substituent carbon number 6～20 aryl, can contain the aralkyl of substituent carbon number 7～20, maybe can contain the acyl group of substituent carbon number 2～10.

R ³⁵～R ⁴²Independent separately expression hydrogen atom, the aliphatic alkyl of carbon number 1～10, alkoxy, carboxyl, sulfo group, sulfamoyl or the N position-replacement sulfamoyl of carbon number 1～8.The hydrogen atom that this aliphatic alkyl is contained, available halogen atom replaces.]

4. as 2 described cured composition for color, wherein, pyridone azo based dye is the salt of compound of compound, formula (3) expression of formula (3) expression or the formed dipolymer of compound of formula (3) expression.

[in the formula (3), Z represents: contain in 1 or 2 alkoxy, hydroxyl, carboxyl, carbamyl, sulfo group, sulfamoyl and the N position-replacement sulfamoyl that is selected from halogen atom, the aliphatic alkyl that can contain substituent carbon number 1～12, carbon number 1～8 at least a kind substituent phenyl; Or contain in 1～3 alkoxy, hydroxyl, carboxyl, carbamyl, sulfo group, sulfamoyl and N position-replacement sulfamoyl that is selected from halogen atom, the aliphatic alkyl that can contain substituent carbon number 1～12, carbon number 1～8 at least a kind substituent naphthyl.

R ²¹Aliphatic alkyl, carboxyl or the trifluoromethyl of the carbon number 1～10 of expression hydrogen atom, straight chain shape, a chain or ring-type.

R ²²Expression hydrogen atom, cyano group, carbamyl, N position-substituted-amino formoxyl, sulfamoyl or sulfo group.

R ²³The expression hydrogen atom; the straight chain shape that can contain substituent carbon number 1～10; prop up the aliphatic alkyl of chain or ring-type; the aryl that can contain substituent carbon number 6～30; the aralkyl that can contain substituent carbon number 7～20; the heterocyclic radical that can contain substituent carbon number 3～20; carbamyl; N position-substituted-amino formoxyl; the alkoxy carbonyl group that can contain substituent carbon number 2～20; the aryl carbonyl oxygen that can contain substituent carbon number 7～30; the acyl group that can contain substituent carbon number 2～20; the aliphatics sulfonyl that can contain substituent carbon number 1～30 maybe can contain the aryl sulfonyl of substituent carbon number 6～30.]

As 1～4 in any described cured composition for color, wherein, also contain (C) adhesive resin.

6. pattern, described pattern uses 1～5 any described cured composition for color, forms with photolithograph method or ink-jet method.

7. a color filter contains 6 described patterns.

8. a liquid crystal indicator possesses 7 described color filters.

Embodiment

Cured composition for color of the present invention as (A) colorant, contains the pigment of formula (1) expression.

In the formula (1), A ¹～A ¹⁶The substituent quantity of expression, preferred chlorine atom is 0～6, bromine atoms is 10～16, and chlorine atom and bromine atoms and be 10～16, more preferably the chlorine atom is 0～3, bromine atoms is 13～16, and chlorine atom and bromine atoms and be 13～16, further preferred chlorine atom is 1～3, and bromine atoms is 13～15, and chlorine atom and bromine atoms and be 14～16.

Substituent quantity is in above-mentioned scope, and the more inclined to one side Huang of form and aspect can improve brightness when being used as color filter under the situation that does not reduce the color rendering scope, and is therefore comparatively desirable.

As the manufacture method of the pigment of formula (1) expression, can use the Jap.P. spy to open 2007-284589 number, spy and open 2007-284592 number, spy and open the method that 2007-291232 number, spy such as open 2008-19383 number at the communique record.

The content of the pigment of formula (1) expression, for (A) colorant full dose, mass fraction is 0.5～99.5 quality %, preferred 1～99 quality %, more preferably 2～98 quality %.

Cured composition for color of the present invention as (A) colorant, also contains weld.Weld is preferably selected from barbiturates azo based dye, pyridone azo based dye, pyrazolone azo based dye, Kui phthalein ketone based dye and the anthocyanin based dye at least a kind dyestuff.

As barbiturates azo based dye, be not particularly limited, can use known substances, preferably use the barbiturates azo based dye of formula (2) expression.

T ¹And T ²Independent separately expression oxygen atom or sulphur atom, can be identical also can be different, preferably identical.

R ³¹～R ³⁴The aliphatic alkyl of carbon number 1～10, can be arbitrarily straight chain shape, chain or ring-type.The carbon number of the aliphatic alkyl of carbon number 1～10, preferred 2～8, more preferably 3～6.Aliphatic alkyl as carbon number 1～10, for example can enumerate methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl, sec-butyl, the tert-butyl group, ethylhexyl (2-ethylhexyl etc.), cyclopentyl, cyclohexyl and cyclohexyl alkyl etc.

In addition, the hydrogen atom that the aliphatic alkyl of carbon number 1～10 is contained, the alkoxy of available hydroxyl, carbon number 1～8 (preferred carbon number 1～4) or the thioalkoxy group of carbon number 1～8 (preferred carbon number 1～4) replace.As the substituted aliphatic alkyl, for example can enumerate hydroxyethyl (2-hydroxyethyl etc.), ethoxyethyl group (2-ethoxyethyl group etc.), ethylhexyl oxygen propyl group (3-(2-ethylhexyl oxygen) propyl group etc.) and methyl thiopropyl (3-methyl thiopropyl etc.) etc.

R ³¹～R ³⁴In the aryl of carbon number 6～20, can not have replacement, also can contain aliphatic alkyl, alkoxy, carboxyl, sulfo group or contain the substituting group of the group etc. of ester bond.The carbon number of above-mentioned aryl comprises substituent carbon number, and preferred 6～10.As aryl, for example can enumerate phenyl, 2-aminomethyl phenyl, 3-aminomethyl phenyl, 4-aminomethyl phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-sulfo group phenyl, 3-sulfo group phenyl, 4-sulfo group phenyl and ethoxy carbonyl phenyl (4-(COOC ₂H ₅) the Ph base etc.) etc.

R ³¹～R ³⁴The moieties of the aralkyl of middle carbon number 7～20 can be arbitrarily straight chain shape, chain or ring-type.The carbon number of aralkyl comprises substituent carbon number, and preferred 7～10.As the aralkyl of carbon number 7～20, can enumerate benzyl and phenethyl etc.

R ³¹～R ³⁴In the acyl group of carbon number 2～10, can not have replacement, also can the bonding aliphatic alkyl or the substituting group of alkoxy etc.The carbon number of acyl group comprises substituent carbon number, and preferred 2～10.As acyl group, for example can enumerate acetyl group, benzoyl, methoxybenzoyl base (to methoxybenzoyl base etc.) etc.

R ³⁵～R ⁴²The aliphatic alkyl of middle carbon number 1～10 can be enumerated and R ³¹～R ³⁴The identical aliphatic alkyl of situation.R ³⁵～R ⁴²The contained hydrogen atom of aliphatic alkyl, also can be replaced by halogen atom,, can enumerate preferred fluorine atom as halogen atom.As the object lesson of the aliphatic alkyl that is replaced by halogen atom, can enumerate trifluoromethyl etc.

R ³⁵～R ⁴²The carbon number of the alkoxy of middle carbon number 1～8, preferred 1～4.As alkoxy, for example can enumerate methoxyl, ethoxy, isopropoxy, positive propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy etc.

R ³⁵～R ⁴²Middle N position-replacement sulfamoyl, for example, preferred N position-replaces sulfamoyl, with-SO ₂NHR ¹³Expression.

R ¹³Expression: can have the acyl group that the aliphatic alkyl of substituent carbon number 1～10, the aryl that can have substituent carbon number 6～20, the aralkyl that can have a substituent carbon number 7～20 maybe can have substituent carbon number 2～10.

R ¹³The aliphatic alkyl of middle carbon number 1～10 can be arbitrarily straight chain shape, chain or ring-type.The carbon number of aliphatic alkyl does not comprise substituent carbon number, and preferred 6～10.

As R ¹³The aliphatic alkyl of middle carbon number 1～10, for example can enumerate, methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl, sec-butyl, the tert-butyl group, methyl butyl (1,1,3,3-tetramethyl butyl etc.), methyl hexyl (1-methyl hexyl, 1,5-dimethyl hexyl etc.), ethylhexyl (2-ethylhexyl etc.), cyclopentyl, cyclohexyl, methylcyclohexyl (2-methylcyclohexyl etc.) and cyclohexyl alkyl etc.

R ¹³The aliphatic alkyl of middle carbon number 1～10, the alkoxy of available carbon number 1～8 (preferred carbon number 1～4) replaces, and for example can enumerate propoxyl group propyl group (3-(isopropoxy) propyl group etc.) etc.

R ¹³The aryl of middle carbon number 6～20 can not have replacement, can contain the substituting group of aliphatic alkyl or hydroxyl etc. yet.The carbon number of above-mentioned aryl comprises substituent carbon number, and preferred 6～10.As aryl, for example can enumerate phenyl, hydroxy phenyl (4-hydroxy phenyl etc.), trifluoromethyl (4-trifluoromethyl etc.) etc.

R ¹³The moieties of the aralkyl of middle carbon number 7～20 can be arbitrarily a straight chain shape or a chain.The carbon number of aralkyl is generally 7～20, and preferred 7～10.As this kind aralkyl, can enumerate the phenylalkyl of benzyl, phenyl propyl (1-methyl-3-phenyl propyl etc.), phenyl butyl (3-amino-1-phenyl butyl etc.) etc. etc.

R ¹³The acyl group of middle carbon number 2～10 can not have replacement, can be that the contained hydrogen atom of acyl group is replaced by aliphatic alkyl or alkoxy yet.The carbon number of acyl group comprises substituent carbon number, and preferred 6～10.As acyl group, for example can enumerate acetyl group, benzoyl, toluoyl base, toluoyl base, toluoyl base and methoxybenzoyl base (to methoxybenzoyl base etc.) etc.

As N position-replacement sulfamoyl, can enumerate the base of formula (4)～(10) expression etc.

As barbiturates azo based dye, can enumerate the compound of formula (2-1)～(2-8) expression, preferred formula (2-1), formula (2-3)～(2-5), (2-7) and (2-8) compound etc. of expression.

As pyridone azo based dye, be not particularly limited, can use known substances, but preferably use the material of formula (3) expression.

R ²³The expression hydrogen atom; the straight chain shape that can contain substituent carbon number 1～10; prop up the aliphatic alkyl of chain or ring-type; the aryl that can contain substituent carbon number 6～30; the aralkyl that can contain substituent carbon number 7～20; the heterocyclic radical that maybe can contain substituent carbon number 3～20; carbamyl; N position-substituted-amino formoxyl; the alkoxy carbonyl group that can contain substituent carbon number 2～20; the aryl carbonyl oxygen that can contain substituent carbon number 7～30; the acyl group that can contain substituent carbon number 2～20; the aliphatics sulfonyl that can contain substituent carbon number 1～30 maybe can contain the aryl sulfonyl of substituent carbon number 6～30.]

In the formula (3), the aliphatic alkyl of the carbon number 1～12 among the Z can be arbitrarily straight chain shape, chain or ring-type.The carbon number of aliphatic alkyl all comprises substituent carbon number, is generally 1～12, and preferred 2～11.As aliphatic alkyl, for example can enumerate n-octyl, methyl hexyl (1,5-dimethyl hexyl etc.), ethylhexyl (2-ethylhexyl etc.), ring octyl group, methylcyclohexyl (2,2-Dimethylcyclohexyl etc.) and cyclohexyl alkyl etc.The hydrogen atom that aliphatic alkyl is contained can be by the alkoxy of carbon number 1～8 or carboxyl substituted.As having substituent aliphatic alkyl, for example can enumerate, the alkoxy propyl group (3-(2 '-ethylhexyl oxygen) propyl group etc.) and 8-(carboxyl) octyl group etc.

As the alkoxy of carbon number among the Z 1～8, for example can enumerate methoxyl, ethoxy, isopropoxy, positive propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy etc.

As the halogen atom among the Z, can enumerate fluorine atom, bromine atoms, chlorine atom and iodine atom.

N position-replacement sulfamoyl among the Z, available-SO ₂N (R ²⁴) R ²⁵Expression.R ²⁴And R ²⁵Independent separately expression hydrogen atom, can contain substituent carbon number 1～16 aliphatic alkyl, can contain substituent carbon number 6～20 aryl, can contain the aralkyl of substituent carbon number 7～20, maybe can contain acyl group (still, the R of substituent carbon number 2～15 ²⁴And R ²⁵Be not hydrogen atom simultaneously).

The aliphatic alkyl of carbon number 1～16 can be arbitrarily straight chain shape, chain or ring-type, the carbon number of aliphatic alkyl, preferred 6～16.

As R ²⁴And R ²⁵The aliphatic alkyl of middle carbon number 1～16 can be arbitrarily straight chain shape, chain or ring-type.In the aliphatic alkyl, do not contain substituent carbon number, be generally 1～16, preferred 6～10.As aliphatic alkyl, for example can enumerate, methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl, sec-butyl, the tert-butyl group, methyl butyl (1,1,3,3-tetramethyl butyl etc.), methyl hexyl (1,5-dimethyl hexyl etc.), ethylhexyl (2-ethylhexyl etc.), cyclopentyl, cyclohexyl, methylcyclohexyl (2-methylcyclohexyl etc.) and cyclohexyl alkyl etc.The hydrogen atom that aliphatic alkyl is contained, the alkoxy of available carbon number 1～8 or carboxyl substituted.As having substituent aliphatic alkyl, can enumerate propoxyl group propyl group (3-(isopropoxy) propyl group etc.), 2-(carboxyl) ethyl, 3-(carboxyl) ethyl and 4-carboxy ethyl etc.

R ²⁴And R ²⁵The aryl of carbon number 6～20, can have substituting groups such as aliphatic alkyl or hydroxyl.The carbon number of aryl comprises substituent carbon number, is generally 6～20, and preferred 6～10.As aryl, can enumerate phenyl, carboxyl phenyl (2-carboxyl phenyl, 2,4-carboxyl phenyl etc.), hydroxy phenyl (4-hydroxy phenyl etc.), trifluoromethyl (4-trifluoromethyl etc.) and methoxyphenyl (4-methoxyphenyl) etc.

R ²⁴And R ²⁵The moieties of aralkyl of carbon number 7～20, can be arbitrarily a straight chain shape or a chain.The carbon number of aralkyl is generally 7～20, and preferred 7～10.As aralkyl, can enumerate, benzyl, phenylethyl (2-phenylethyl, 2-(4-hydroxy phenyl) ethyl etc.), phenyl-1, the phenylalkyl of 2-methylene (2-phenyl-1,2-methylene etc.), phenyl propyl (1-methyl-3-phenyl propyl etc.) and phenyl butyl (3-amino-1-phenyl butyl etc.) etc.

R ²⁴And R ²⁵The acyl group of carbon number 2～15, can not have replacement, also can have the substituting group of aliphatic alkyl, alkoxy or carboxyl etc.The carbon number of acyl group comprises substituent carbon number, is generally 2～15, and preferred 6～10.As acyl group; for example can enumerate acetyl group, benzoyl, methoxybenzoyl base (to methoxybenzoyl base etc.), carboxyl acetyl group, 2-carboxypropanoyl, 3-carboxypropanoyl, 2-carboxyl bytyry, 3-carboxyl bytyry and 4-carboxyl bytyry etc.

R ²¹The carbon number of aliphatic alkyl of carbon number 1～10, do not comprise substituent carbon number.Its carbon number is preferred 2～8, and more preferably 3～6.As aliphatic alkyl, can enumerate methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl, sec-butyl, the tert-butyl group, cyclopentyl and cyclohexyl etc.

R ²²Expression hydrogen atom, cyano group, carbamyl or N position-substituted-amino formoxyl, sulfamoyl or sulfo group.

As R ²²N position-substituted-amino formoxyl, can enumerate-CON (R ²⁶) R ²⁷R ²⁶And R ²⁷Represent hydrogen atom independently of one another, can contain substituent carbon number 1～10 aliphatic alkyl, can contain substituent carbon number 6～20 aryl, can contain the aralkyl of substituent carbon number 7～20, maybe can contain the acyl group of substituent carbon number 2～10.

R ²⁶And R ²⁷Explanation and the object lesson and the above-mentioned R of aliphatic alkyl, aryl, aralkyl and acyl group ²⁴And R ²⁵Identical.But acyl group can contain halogen atom.As the acyl group that contains halogen atom, for example can enumerate benzoyl bromide (to benzoyl bromide etc.) etc.

R ²³The expression hydrogen atom; the straight chain shape that can contain substituent carbon number 1～10; prop up the aliphatic alkyl of chain or ring-type; the aryl that can contain substituent carbon number 6～30; the aralkyl that can contain substituent carbon number 7～20; the heterocyclic radical that can contain substituent carbon number 3～20; carbamyl; N position-substituted-amino formoxyl; the alkoxy carbonyl group that can contain substituent carbon number 2～20; the aryl carbonyl oxygen that can contain substituent carbon number 7～30; the acyl group that can contain substituent carbon number 2～20; the aliphatics sulfonyl that can contain substituent carbon number 1～30 maybe can contain the aryl sulfonyl of substituent carbon number 6～30.

As R ²³Aliphatic alkyl, can enumerate and above-mentioned R ²¹The identical group of aliphatic alkyl.

As R ²³Aryl, carbon number is generally 6～30, and is preferred 6～20, more preferably 6～16.Object lesson as aryl, can enumerate, phenyl, 4-nitrobenzophenone, 2-nitrobenzophenone, 2-chlorphenyl, 2,4-dichlorophenyl, 2,4-3,5-dimethylphenyl, 2-aminomethyl phenyl, 4-methoxyphenyl, 2-methoxyphenyl and 2-methoxycarbonyl-4-nitrobenzophenone etc.

As R ²³Aralkyl, can be arbitrarily straight chain shape or chain, carbon number preferred 7～10.As the object lesson of aralkyl, can enumerate the phenylalkyl of benzyl, phenyl propyl (1-methyl-3-phenyl propyl etc.) and phenyl butyl (3-amino-1-phenyl butyl etc.) etc. etc.

As R ²³The heterocyclic radical of carbon number 3～20, can be saturated, also can be unsaturated, preferred 3～20 as carbon number, more preferably 5～15.As the object lesson of heterocyclic radical, can enumerate pyrazolyl, 1,2,4-triazolyl, isothiazolyl, benzisothiazole base, thiazolyl, benzothiazolyl, oxazolyl and 1,2,4-thiadiazolyl group etc.In addition, also can contain substituting group.

As R ²³N position-substituted-amino formoxyl, with above-mentioned R ²²N position-substituted-amino formoxyl identical.

As R ²³Alkoxy carbonyl group, can be and do not have to replace, also can contain substituting group, also can be ring-type.As the carbon number of alkoxy carbonyl group, be generally 2～20, preferred 2～16, more preferably 2～10.As alkoxy carbonyl group, can enumerate methoxycarbonyl, ethoxy carbonyl and butoxy carbonyl etc.

As R ²³Aryl carbonyl oxygen, can be and do not have to replace, also can contain substituting group, as carbon number, be generally 7～30, preferred 7～20, more preferably 7～16.As aryl carbonyl oxygen, can enumerate phenyloxycarbonyl and 4-methylphenoxy carbonyl etc.

As R ²³Acyl group, can be the aliphatics carbonyl, also can be aryl carbonyl, also can be saturated or undersaturated any one, also can be ring-type, also can contain substituting group.As carbon number, be generally 2～20, preferred 2～15, more preferably 2～10.As acyl group, can enumerate acetyl group, propiono, bytyry, isobutyryl, valeryl, isovaleryl, pivaloyl group, benzoyl etc.

As R ²³The aliphatics sulfonyl, can be saturated, also can be unsaturated, also can be ring-type.As carbon number, be generally 1～30, preferred 1～20, more preferably 1～16.As the aliphatics sulfonyl, can enumerate methane sulfonyl, butane sulfonyl, methoxyl methane sulfonyl, Ethyl Methyl Ether sulfonyl and Ethoxyethane sulfonyl etc.

As R ²³Aryl sulfonyl, can contain substituting group, as carbon number, be generally 6～30, preferred 6～20, more preferably 6～18.As aryl sulfonyl, can enumerate benzene sulfonyl and tosyl etc.

As pyridone azo based dye, can enumerate following compound, the compound of preferred formula (3-1)～(3-9) expression.

The compound of formula (3) expression can form any one of ammonium salt, lithium salts, sodium salt or sylvite.

The compound of formula (3) expression can form the above polymer of dipolymer.

The polymer of formula (3) is the compound from the group of the compound of formula (3) expression that contains in 1 molecule more than 2, specifically can enumerate the compound of formula (3-12) formula (3-15) expression etc.

As pyrazolone azo based dye, be not particularly limited, can use known substances, for example, can use the Jap.P. spy open 2006-276512 number, the spy opens 2005-263926 number and the special pyrazolone azo based dye of the communique record such as opening 2006-015669 number.

Concrete, can enumerate the compound of C.I. Indian yellow 17 (C.I.AcidYellow 17), C.I. solvent orange 56 (C.I.SolventOrange 56) and C.I. solvent yellow 82 (C.I.SolventYellow 82) or formula (11)～(14) expression etc.

As Kui phthalein ketone based dye, be not particularly limited, can use known substances, for example, can use Japanese patent laid-open 5-39269 number, the spy opens flat 6-220339 number and the special Kui phthalein ketone based dye of the communique record such as opening flat 8-171201 number.

Concrete, can enumerate the compound of C.I. solvent yellow 33 (C.I.SolventYellow 33), C.I. disperse yellow 54 (DisperseYellow 54), C.I. dispersion yellow 64 (C.I.DisperseYellow 64) or formula (15)～(19) expression etc.

As the anthocyanin based dye, be not particularly limited, can use known substances.

For example, can use the Jap.P. spy open 2005-194509 number, the spy opens 2007-131818 number and the special anthocyanin that the communique record such as opens 2005-297406 number is a pigment.

Concrete, can enumerate the compound of formula (20)～(23) expression etc.

In addition, as (A) colorant, in the scope of harmless effect of the present invention, can contain other dyestuff and pigment.

As above-mentioned dyestuff, can enumerate, be categorized as the compound of dyestuff among the Color Index (The Society of Dyers and Colourists publication), or the known dyestuff of dyeing Note (look dyes society) record, specifically can enumerate, C.I. (statement of following omission C.I.SolventYellow only indicates numbering to solvent yellow-4 (C.I.SolventYellow-4).Other dyestuff kinds and form and aspect are omitted record too.), 14,15,23,24,38,62,63,68,82,94,98,99,162, C.I. solvent green (C.I.SolventGreen) 1,3,4,5,7,28,29,32,33,34,35, C.I. solvent orange (C.I.SolventOrange) 2,7,11,15,26,45,56 etc.In addition, as the C.I. acid dyes, can enumerate C.I. acid green (C.I.AcidGreen) 1,3,5,9,16,25,27,50,58,63,65,80,104,105,106,109, C.I. acid orange (C.I.AcidOrange) 6,7,8,10,12,26,50,51,52,56,62,63,64,74,75,94,95,107,108,169,173, C.I. Indian yellow (C.I.AcidYellow) 1,3,7,9,11,17,23,25,29,34,36,38,40,42,54,65,72,73,76,79,98,99,111,112,113,114,116,119,123,128,134,135,138,139,140,144,150,155,157,160,161,163,168,169,172,177,178,179,184,190,193,196,197,199,202,203,204,205,207,212,214,220,221,228,230,232,235,238,240,242,243,251 or derivatives thereofs.In addition, as C.I. direct dyes (C.I.Direct), can enumerate directly yellow (DirectYellow) 2 of C.I., 33,34,35,38,39,43,47,50,54,58,68,69,70,71,86,93,94,95,98,102,108,109,129,136,138,141, C.I. direct orange (DirectOrange) 34,39,41,46,50,52,56,57,61,64,65,68,70,96,97,106,107, C.I. direct green (DirectGreen) 25,27,31,32,34,37,63,65,66,67,68,69,72,77,79,82 dyestuffs such as grade.In addition, as C.I. media (Mordant) dyestuff, can enumerate dyestuffs such as C.I. media Huang (Mordant Yellow) 5,8,10,16,20,26,30,31,33,42,43,45,56,61,62,65, C.I. media orange (MordantOrange) 3,4,5,8,12,13,14,20,21,23,24,28,29,32,34,35,36,37,42,43,47,48, C.I. media green (MordantGreen) 1,3,4,5,10,15,19,26,29,33,34,35,41,43,53.Preferred C.I. solvent yellow (SolventYellow)-4,14,15,23,24,38,62,63,68,82,94,98,99,162, acid green (AcidGreen) 1,3,5,9,16,25,27,50,58,63,65,80,104,105,106,109, C.I. Indian yellow (AcidYellow) 1,3,7,9,11,17,23,25,29,34,36,38,40,42,54,65,72,73,76,79,98,99,111,112,113,114,116,119,123,128,134,135,138,139,140,144,150,155,157,160,161,163,168,169,172,177,178,179,184,190,193,196,197,199,202,203,204,205,207,212,214,220,221,228,230,232,235,238,240,242,243,251,23,25,29,34,40,42,72,76,99,111,112,114,116,163,243 or derivatives thereofs.

As above-mentioned pigment, can enumerate, Color Index (The Society of Dyers and Colourists publication) is categorized as the compound of pigment (Pigment).Specifically can enumerate, for example, yellow uitramarine such as C.I. pigment yellow (PigmentYellow) 1,3,12,13,14,15,16,17,20,24,31,53,83,86,93,94,109,110,117,125,128,137,138,139,147,148,150,153,154,166,173,194,214; C.I. viridine green such as naphthol green (PigmentGreen) 7,36; Preferred C.I. pigment yellow (PigmentYellow) 138,139,150, C.I. naphthol green (PigmentGreen) 7,36.

Above-mentioned pigment as required, can carry out dispersion treatment by containing pigment dispersing agent, obtains the dispersible pigment dispersion that pigment is dispersed in the state in the solution.

As above-mentioned pigment dispersing agent, for example can enumerate, the interfacial agents of kation system, negative ion system, nonionic system, both sexes, polyester system and polyamine system etc. etc. can be used singly or two or more kinds in combination.

Example as this interfacial agent, can enumerate, the polyoxyethylene alkyl ether class, the polyoxyethylene alkyl phenyl ether class, the polyethylene glycol di class, the sorbitan fatty acid ester class, fatty acid modified polyesters, the tertiary amine modified polyurethane, polyethyleneimine: amine etc., also have in addition, product is called KP (manufacturing of chemical industrial company of SHIN-ETSU HANTOTAI), Port リ Off ロ one (manufacturing of common prosperity chemical company), エ Off ト Star プ (manufacturing of ト one ケ system プロダ Network Star company), メガ Off ア Star Network (big Japanese イ Application キ chemical industrial company make), Off ロラ one De (manufacturing of Sumitomo スリ one エ system company), アサヒガ one De, サ one Off ロ Application (above make for Asahi Glass company), ソ Le スパ one ス (manufacturing of ゼネカ company), EFKA (manufacturing of EFKACHEMICALS company), PB821 (manufacturing of aginomoto company) and デイスパ one PVC Star Network (manufacturing of PVC Star Network ケミ one company) etc.

When using spreading agent, its use amount is, with respect to pigment 100 quality %, and preferred 0.1～100 quality % of mass fraction, more preferably 5～50 quality %.

As the mean grain size of the pigment in the dispersible pigment dispersion, be 10～150nm, preferred 15～120nm, more preferably 20～100nm.

(A) content of colorant is, with respect to the solid constituent of cured composition for color, mass fraction is 10～95 quality %, preferred 15～90 quality %, more preferably 20～88 quality %.

Herein, the solid constituent in this instructions refers to the one-tenth subtotaling amount of having removed behind the contained solvent of cured composition for color.

The content of the employed yellow uitramarine of cured composition for color of the present invention is that for the holochrome of yellow, mass fraction is 0.5～100 quality %, preferred 1～100 quality %, more preferably 2～100 quality %.

In addition, the content of the employed yellow uitramarine of cured composition for color of the present invention is that for the holochrome of (A) colorant full dose yellow, mass fraction is 0.5～99.5 quality %, preferred 1～99 quality %, more preferably 2～98 quality %.

The content of weld is in above-mentioned scope, and the brightness and contrast during as color filter has the tendency that uprises, and is therefore comparatively desirable.

As (B) polymerizable compound, the monomer or the oligomer that can use heat or light or both to be cured, but also both also use.As monomer or oligomer, can use known substances.

Object lesson as monomer, can enumerate pentaerythritol tetracrylate, pentaerythritol tetramethacrylate, pentamethyl acrylic acid dipentaerythritol ester, hexamethyl acrylic acid dipentaerythritol ester, carboxylic five acrylic acid dipentaerythritol ester derivants, oxiraneization three acrylic acid glyceride, oxirane trimethyol propane triacrylate and epoxypropaneization three acrylic acid glyceride etc.

As oligomer, can enumerate, epoxy acrylate, acrylic acid urethane ester, polyester acrylate etc., for example, 18 pages of the status and prospects (シ one エ system シ one publish) that can use the UVEB curing technology are to the oligomer of 20 pages of records etc.

(B) content of polymerizable compound is, for the solid constituent of cured composition for color, and preferred 5～90 quality % of mass fraction, more preferably 10～85 quality %, preferred especially 12～80 quality %.

Cured composition for color of the present invention can also contain (C) adhesive resin.(C) adhesive resin preferably contains and is derived from (methyl) acrylic acid repetitive.Here, (methyl) acrylic acid represent acrylic acid with and/or methacrylic acid.Be derived from the content of (methyl) acrylic acid repetitive, in all repetitives that constitute adhesive resin, preferred 10mol% of mole fraction and above, 40mol% and following, more preferably 13mol% and above, 35mol% and following.

As other monomers by the repetitive that is derived from (methyl) acrylic acid repetitive introducing adhesive resin in addition; for example can enumerate; aromatic ethylene compound; unsaturated carboxylate type; unsaturated carboxylic acid aminoalkyl ester class; unsaturated carboxylic acid ethylene oxidic ester class; the vinyl carboxylates class; unsaturated ether; the vinyl cyanide compound; the unsaturated acyl amine; unsaturated acid imide; the aliphatics conjugated diene; the polymer molecule chain end has the macromonomer of single acryloyl group and monomethyl acryloyl group; for example, the repetitive of the repetitive of formula (24) expression and formula (25) expression etc.

[in formula (24) and the formula (25), R ⁵¹And R ⁵²The representative examples of saturated aliphatic alkyl of representing hydrogen atom or carbon number 1～6 independently of one another.]

As R ⁵¹And R ⁵²Can enumerate, hydrogen atom, methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl, the tert-butyl group, n-pentyl, 1-methyl butyl, 2-methyl butyl, 3-methyl butyl, 1-ethyl propyl, 2-ethyl propyl, n-hexyl, 1-methyl amyl, 2-methyl amyl, 3-methyl amyl, 4-methyl amyl, 1-ethyl-butyl, 2-ethyl-butyl and 3-ethyl-butyl etc., preferred hydrogen atom, methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl or the tert-butyl group, more preferably hydrogen atom, methyl or ethyl.

As (C) adhesive resin, specifically can enumerate, the repetitive of methacrylic acid/benzyl methacrylate multipolymer, methacrylic acid/benzyl methacrylate/styrol copolymer, methacrylic acid/benzyl methacrylate/isobornyl methacrylate multipolymer, methacrylic acid/styrene/methacrylic acid benzyl ester/N-phenylmaleimide multipolymer, methacrylic acid/formula (25) expression (still, herein, in the formula (25), R ³¹Expression methyl, R ³²The expression hydrogen atom.The repetitive of)/N-benzyl maleimide/benzyl methacrylate multipolymer, methacrylic acid/formula (25) expression (still, herein, in the formula (25), R ⁵¹Expression methyl, R ⁵²The expression hydrogen atom.The repetitive of)/N-cyclohexyl maleimide/benzyl methacrylate multipolymer, methacrylic acid/formula (24) expression (still, herein, in the formula (24), R ⁵¹Expression methyl, R ⁵²The expression hydrogen atom.The repetitive of)/benzyl methacrylate multipolymer, formula (24) expression (still, herein, in the formula (24), R ⁵¹Expression methyl, R ⁵²The expression hydrogen atom.The repetitive of)/benzyl methacrylate multipolymer, methacrylic acid/formula (25) expression (still, herein, in the formula (25), R ⁵¹Expression methyl, R ⁵²The expression hydrogen atom.)/styrene/methacrylic acid two cyclopentene ester copolymers etc.

(C) acid number of adhesive resin is preferred 30～150, and more preferably 35～135, preferred especially 40～120.Acid number herein, be as in and the amount (mg) of the necessary potassium hydroxide of acrylic acid series condensate of 1g and the value measured can be tried to achieve by using the potassium hydroxide aqueous solution titration usually.

(C) content of adhesive resin, with respect to the solid constituent of cured composition for color, preferred 5～40 quality % of mass fraction, more preferably 8～35 quality %, preferred especially 10～32 quality %.

(C) adhesive resin with repetitive of formula (24) expression, for example, contain repetitive/formula (24) expression from methacrylic acid repetitive (still, herein, in the formula (24), R ⁵¹Expression methyl, R ⁵²The expression hydrogen atom.)/from the repetitive of benzyl methacrylate and the multipolymer that constitutes can pass through, and methacrylic acid and benzyl methacrylate polymerization obtain 2 composition condensates, the compound that makes the expression of the 2 composition condensates that obtain and formula (26) (still, herein, in the formula (26), R ⁵³The expression hydrogen atom.) reaction and obtain.

Contain repetitive/formula (25) expression from methacrylic acid repetitive (still, herein, in the formula (25), R ⁵¹Expression methyl, R ⁵²The expression hydrogen atom.)/from the repetitive of benzyl methacrylate/and the multipolymer that constitutes from the repetitive of methacrylic acid two cyclopentene esters, can pass through, the multipolymer of benzyl methacrylate, methacrylic acid, methacrylic acid two cyclopentene esters obtains with the glycidyl methacrylate reaction.

(C) the polystyrene conversion weight-average molecular weight of adhesive resin, preferred 5,000～100,000, more preferably 6,000～80,000, preferred especially 7,000～60,000.Molecular weight is in above-mentioned scope, and hardness of film can rise, residual film ratio is also higher, unexposed portion is for the favorable solubility of developer solution, the tendency that resolution has lifting, and is therefore comparatively desirable.

Cured composition for color of the present invention can also contain (D) polymerization initiator.As polymerization initiator, can enumerate triazine based compound, acetophenone based compound, bisglyoxaline based compound, living radical initiating agent and sour initiating agent etc.

As the triazine based compound, for example can enumerate, 2,4-two (trichloromethyl)-6-(4-methoxyphenyl)-1,3, the 5-triazine, 2,4-two (trichloromethyl)-6-(4-methoxyl naphthyl)-1,3, the 5-triazine, 2,4-two (trichloromethyl)-6-(4-methoxyl-styrene)-1,3, the 5-triazine, 2,4-two (trichloromethyl)-6-[2-(5-methylfuran-2-yl) vinyl]-1,3,5-triazines, 2,4-two (trichloromethyl)-6-[2-(furans-2-yl) vinyl]-1,3, the 5-triazine, 2,4-two (trichloromethyl)-6-[2-(4-diethylamino-2-aminomethyl phenyl) vinyl]-1,3, the 5-triazine, 2,4-two (trichloromethyl)-6-[2-(3, the 4-Dimethoxyphenyl) vinyl]-1,3,5-triazine and 2,4-two (trichloromethyl)-6-piperonyl-1,3,5-triazine etc., preferred 2,4-two (trichloromethyl)-6-(4-methoxyphenyl)-1,3, the 5-triazine, 2,4-two (trichloromethyl)-6-(4-methoxyl naphthyl)-1,3,5-triazines, 2,4-two (trichloromethyl)-6-(4-methoxyl-styrene)-1,3,5-triazine or 2,4-two (trichloromethyl)-6-piperonyl-1,3, the 5-triazine, more preferably 2,4-two (trichloromethyl)-6-piperonyl-1,3, the 5-triazine.

As the acetophenone based compound, for example can enumerate, diethoxy acetophenone, 2-methyl-2-morpholino-1-(4-methyl thio-phenyl) propane-1-ketone, 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone, benzyl dimethyl ketal, 2-hydroxy-2-methyl-1-[4-(2-hydroxyl-oxethyl) phenyl] propane-1-ketone, the 1-hydroxycyclohexylphenylketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone, 2-(4-methyl-benzyl)-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone and 2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl] oligomer etc. of propane-1-ketone, preferred 2-methyl-2-morpholino-1-(4-methyl thio-phenyl) propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl-butane-1-ketone or 2-(4-methyl-benzyl)-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone, more preferably 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone or 2-(4-methyl-benzyl)-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone.

As the bisglyoxaline based compound, for example can enumerate 2,2 '-two (2-chlorphenyls)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2 '-two (2-chlorphenyl)-4,4 ', 5,5 '-four (4-carbon ethoxyl phenenyl) bisglyoxaline, 2,2 '-two (2-chlorphenyl)-4,4 ', 5,5 '-four (4-bromophenyl) bisglyoxaline, 2,2 '-two (2-chlorphenyls)-4,4 ', 5,5 '-four (2, the 4-dichlorophenyl) bisglyoxaline, 2,2 '-two (2-bromophenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2 '-two (2, the 4-dichlorophenyl)-4,4 ', 5,, 5 '-tetraphenyl bisglyoxaline, 2,2 '-two (2-chlorphenyls)-4,4 ', 5,5 '-four (m-methoxyphenyl) bisglyoxaline, 2,2 '-two (2, the 3-dichlorophenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2 '-two (2, the 6-dichlorophenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2 '-two (2-nitre phenyl)-4,4 ' 5,5 '-tetraphenyl bisglyoxaline and 2,2 '-two (2-aminomethyl phenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline etc., preferred 2,2 '-two (2-chlorphenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline or 2,2 '-two (2, the 3-dichlorophenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline.

The living radical initiating agent by rayed after, can produce living radical.As the living radical initiating agent, for example can enumerate styrax based compound, benzophenone based compound, thioxanthones based compound and oxime compound etc.

As the styrax based compound, for example can enumerate styrax, styrax methyl ether, styrax ethylether, benzoin isobutyl propyl group ether and benzoin isobutyl butyl ether etc.

As the benzophenone based compound, for example can enumerate benzophenone, adjacent benzophenone methyl formate, 4-phenyl benzophenone, 4-benzoyl-4 '-methyldiphenyl base sulfide, 3,3 ', 4,4 '-four (tert-butyl hydroperoxide carbonyl) benzophenone and 2,4,6-tri-methyl benzophenone etc.

As the thioxanthones based compound, for example can enumerate 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-two clopenthixal ketones and 1-chloro-4-propoxyl group thioxanthones etc.

As oxime compound; for example can enumerate; O-acyl group oxime compound; object lesson has; 1-(4-phenyl sulphonyl-phenyl)-butane-1; 2-diketone 2-oxime-O-benzoic ether, 1-(4-phenyl sulphonyl-phenyl) octane-1,2-diketone 2-oxime-O-benzoic ether, 1-(4-phenyl sulphonyl-phenyl)-octane-1-ketoxime-O-acetic acid esters and 1-(4-phenyl sulphonyl-phenyl)-butane-1-ketoxime-O-acetic acid esters etc.

As the living radical initiating agent beyond above-mentioned, for example can enumerate, 2,4,6-trimethylbenzene formyl diphenyl phosphine oxide, 10-butyl-2-chloro-acridine ketone, 2-EAQ, diphenylthanedione, 9-10-phenanthrenequione, camphorquinone, phenyl glyoxalic acid methylester and two cyclopentadiene titanium compounds etc.

As sour initiating agent, for example can enumerate salt or toluenesulfonic acid nitrobenzyl ester class, the styrax tosylate class etc. of 4-hydroxyphenyl dimethyl sulfonium p-toluenesulfonic esters, 4-hydroxyphenyl dimethyl sulfonium hexafluoro oxygen antimony ester (ア Application チモネ one ト), 4-acetoxyl group phenyl dimethyl sulfonium-p-toluenesulfonic esters, 4-acetyloxy phenyl methyl-benzyl sulfonium hexafluoro oxygen antimony ester, triphenylsulfonium p-toluenesulfonic esters, triphenylsulfonium hexafluoro oxygen antimony ester, diphenyl iodo-p-toluenesulfonic esters, diphenyl iodine hexafluoro oxygen antimony ester etc.

In addition, in above-mentioned compound, also have and acidic compound of living radical while, for example, triazine system is poly-also to can be used as sour initiating agent with initiating agent.

(D) content of polymerization initiator is, with respect to (B) polymerizable compound and (C) the total amount of adhesive resin, preferred 0.1～25 quality % of mass fraction, more preferably 1～20 quality %.

In the cured composition for color of the present invention, can also contain (E) polymerization and cause auxiliary agent.(E) polymerization causes that auxiliary agent is general to be used in combination with (D) polymerization initiator, is the polymerizable compound polymeric compounds that is used for promoting by (D) polymerization initiator initiated polymerization.

Cause auxiliary agent as (E) polymerization, can enumerate amine compound, alkoxy anthracene based compound, thioxanthones based compound etc.

As amine compound, for example can enumerate, triethanolamine, methyldiethanolamine, triisopropanolamine, 4-dimethylaminobenzoic acid methyl esters, 4-dimethylaminobenzoic acid ethyl ester, 4-dimethylaminobenzoic acid isopentyl ester, benzoic acid 2-dimethylamino ethyl ester, 4-dimethylaminobenzoic acid 2-Octyl Nitrite, N, the N-dimethyl-p-toluidine, 4,4 '-two (dimethylamino) benzophenone, 4,4 '-two (diethylamino) benzophenone and 4,4 '-two (ethylmethylamino) benzophenone etc., preferred 4,4 '-two (diethylamino) benzophenone.

As the alkoxy anthracene based compound, for example can enumerate, 9,10-dimethoxy anthracene, 2-ethyl-9,10-dimethoxy anthracene, 9,10-diethoxy anthracene and 2-ethyl-9,10-diethoxy anthracene etc.

(E) polymerization initiation auxiliary agent can be used singly or two or more kinds in combination.In addition, cause auxiliary agent, can use the commercially available prod as (E) polymerization, cause auxiliary agent as commercially available (E) polymerization, for example can enumerate, commodity are called EAB-F, and (hodogaya chemical industrial group makes, 4,4 '-two (diethylamino) benzophenone) etc. organic amine compound etc.

As (D) polymerization initiator/(E) polymerization causes the combination of auxiliary agent, for example can enumerate, 2,4-two (trichloromethyl)-6-piperonyl-1,3,5-triazine/4,4 '-two (diethylamino) benzophenone, diethoxy acetophenone/4,4 '-two (diethylamino) benzophenone, 2-methyl-2-morpholino-1-(4-methyl thio-phenyl) propane-1-ketone/4,4 '-two (diethylamino) benzophenone, 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone/4,4 '-two (diethylamino) benzophenone, benzyl dimethyl ketal/4,4 '-two (diethylamino) benzophenone, 2-hydroxy-2-methyl-1-[4-(2-hydroxyl-oxethyl) phenyl] propane-1-ketone/4,4 '-two (diethylamino) benzophenone, 1-hydroxycyclohexylphenylketone/4,4 '-two (diethylamino) benzophenone, 2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl] oligomer/4 of propane-1-ketone, 4 '-two (diethylamino) benzophenone, 2-benzyl-2-(dimethylamino-1-(4-morpholino phenyl) butane-1-ketone/4,4 '-two (diethylamino) benzophenone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone/4,4 '-two (diethylamino) benzophenone and 2-(4-methyl-benzyl)-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone/4,4 '-two (diethylamino) benzophenone etc., preferred 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone/4,4 '-two (diethylamino) benzophenone, 2,4-two (trichloromethyl)-6-piperonyl-1,3,5-triazine/4,4 '-two (diethylamino) benzophenone, 2-(4-methyl-benzyl)-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone/4,4 '-two (diethylamino) benzophenone.

When using (E) polymerization to cause auxiliary agent, its use amount is, with respect to (D) polymerization initiator of per 1 mass parts, preferred 0.01～10 mass parts, more preferably 0.01～5 mass parts.

Cured composition for color of the present invention can also contain (F) solvent.As (F) solvent, for example can enumerate ethers, aromatic hydrocarbon based, ketone, ethanol class, ester class and amide-type etc.

As ethers, for example can enumerate, tetrahydrofuran, oxinane, 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, the diethylene glycol dipropyl ether, the diethylene glycol dibutyl ethers, propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters, propylene glycol list propyl ether acetic acid esters, the methyl acetic acid cellosolve, ethyl acetic acid cellosolve, the ethyl carbitol acetic acid esters, acetate of butyl carbitol, methyl proxitol acetate, methoxyl butylacetic acid ester, methoxyl amyl group acetic acid esters, methyl phenyl ethers anisole, phenetol, methylbenzene methyl ether etc.

As aromatic hydrocarbon based, for example can enumerate benzene,toluene,xylene and trimethylbenzene etc.

As ketone, for example can enumerate acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2 pentanone, cyclopentanone, cyclohexanone and 4-hydroxy-4-methyl-2 pentanone etc.

As the ethanol class, for example can enumerate methyl alcohol, ethanol, propyl alcohol, butanols, hexanol, cyclohexanol, ethylene glycol, diacetone ethanol and glycerine etc.

As the ester class, for example can enumerate ethyl acetate, acetate-positive butyl ester, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl isobutyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, hydroxy methyl acetate, hydroxyl ethyl acetate, the glycolic acid butyl ester, methoxy menthyl acetate, the methoxyacetic acid ethyl ester, the methoxyacetic acid butyl ester, ethoxy acetate, ethoxy ethyl acetate, the 3-hydroxy methyl propionate, 3-hydracrylic acid ethyl ester, 3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, the 3-ethoxyl ethyl propionate, the 2 hydroxy propanoic acid methyl esters, the 2 hydroxy propanoic acid ethyl ester, the 2 hydroxy propanoic acid propyl ester, 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-hydroxy-2-methyl methyl propionate, 2-hydroxy-2-methyl ethyl propionate, 2-methoxyl-2 Methylpropionic acid methyl esters, 2-ethoxy-2 Methylpropionic acid ethyl ester, methyl pyruvate, ethyl pyruvate, Propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, 2-carbonyl methyl butyrate, 2-carbonyl ethyl butyrate, 3-methoxyl butylacetic acid ester, 3-methyl-3-methoxyl butylacetic acid ester and gamma-butyrolacton etc.

As amide-type etc., for example can enumerate N, dinethylformamide and N,N-dimethylacetamide etc.

As other solvent, for example can enumerate N-Methyl pyrrolidone and dimethyl sulfoxide (DMSO) etc.

(F) solvent can be used singly or two or more kinds in combination separately.

(F) solvent, preferred propylene glycol monomethyl ether, propylene glycol monomethyl ether, ethyl lactate or diacetone ethanol.

(F) content of solvent, with respect to cured composition for color, preferred 70～90 quality % of mass fraction, more preferably 75～88 quality %.

Cured composition for color of the present invention can also contain (G) surfactant.As (G) surfactant, can enumerate, silicone type surface active agent, fluorine are surfactant and the silicone type surface active agent with fluorine atom.

As silicone type surface active agent, can enumerate, contain the surfactant of siloxane bond etc.Specifically can enumerate, commodity are called ト one レシリコ one Application DC3PA, same SH7PA, same DC11PA, same SH21PA, same SH28PA, same 29SHPA, same SH30PA, polyether modified silicon oil SH8400 (manufacturing of ト one レシリコ one Application company), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (the シリコ of SHIN-ETSU HANTOTAI one Application manufacturing), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, TSF4460 (manufacturing of ジ one イ one シリコ one Application company of Toshiba) etc.

As fluorine is surfactant, can enumerate, and has the surfactant of carbon fluorine chain etc.Specifically can enumerate, commodity are called Off ロラ one De FC430, same FC431 (manufacturing of Sumitomo スリ one エ system company), メガ Off ア Star Network F142D, same F171, same F172, same F173, same F177, same F183, same F470, same F475, same R30 (big Japanese イ Application キ chemical industrial company make), エ Off ト Star プ EF301, same EF303, same EF351, same EF352 (the new autumn fields company that changes into makes), サ one Off ロ Application S381, same S382, same SC101, same SC105 (manufacturing of Asahi Glass company), E5844 (manufacturing of company of ダイキ Application Off アイ Application ケミカ Le research institute), BM-1000, BM-1100 (manufacturing of BM Chemie company) etc.

As silicone type surface active agent with fluorine atom, can enumerate, have the surfactant of siloxane bond and carbon fluorine chain etc.Specifically can enumerate, commodity are called メガ Off ア Star Network R08, same BL20, same F475, same F477, same F443 (big Japanese イ Application キ chemical industrial company make) etc.

These surfactants can be used singly or two or more kinds in combination.

In the cured composition for color of the present invention, can contain the organic acid of molecular weight below 1,000.As above-mentioned organic acid, for example can enumerate the disclosed organic acid of Japanese patent laid-open 5-343631 communique.Specifically can enumerate, malonic acid, ethane diacid, succinic acid, glutaric acid, hexane diacid, benzoic acid, phthalic acid, different phthalic acid, terephthalic acid (TPA), citraconic acid, itaconic acid, mesaconic acid, fumaric acid, phthalic acid, acrylic acid and methacrylic acid, preferred malonic acid, ethane diacid, fumaric acid or phthalic acid.By containing molecular weight 1,000 and following organic acid, can further optimize residue, therefore comparatively desirable.

In the cured composition for color of the present invention, can also contain macromolecular compound beyond the filling agent, (C) adhesive resin, connect airtight adjuvants such as promoter, antioxidant, ultraviolet light absorber, anti-coagulants, organic amine compound, (H) hardening agent.

As filling agent, for example can enumerate the particulate of glass and aluminium oxide etc.

As the macromolecular compound beyond (C) adhesive resin, for example can enumerate polyvinyl alcohol (PVA), polyacrylic acid, polyalkylene glycol monoalkyl ether and poly-fluoroalkyl acrylate etc.

As connecting airtight promoter, for example can enumerate, vinyltrimethoxy silane, vinyltriethoxysilane, vinyl three (2-methoxy ethoxy) silane, N-(2-amino-ethyl)-3-aminopropyl methyl dimethoxysilane, N-(2-amino-ethyl)-3-TSL 8330, the 3-aminopropyltriethoxywerene werene, the 3-glycidoxy-propyltrimethoxy silane, the 3-epoxy third oxygen methyl dimethoxysilane, 2-(3, the 4-epoxycyclohexyl) ethyl trimethoxy silane, the 3-chloropropylmethyldimethoxysilane, the 3-r-chloropropyl trimethoxyl silane, 3-metering system oxygen propyl trimethoxy silicane and 3-sulfydryl propyl trimethoxy silicane etc.

As antioxidant, for example can enumerate, 4,4 '-sulfo--two (6-tert-butyl group-3-methylphenol, triethylene glycol-two [3-(the 3-tert-butyl group-5-methyl-4-hydroxy phenyl) propionic ester], 1,6-hexanediol-two-[3-(3,5-two-tert-butyl-hydroxy phenyl) propionic ester], [3-(3 for pentaerythrite-four, 5-two-tert-butyl-hydroxy phenyl) propionic ester], eight decyls-3-(3,5-two-tert-butyl-hydroxy phenyl) propionic ester, 1,3,5-trimethyl-2,4,6-three (3,5-two-tertiary butyl-4-hydroxy benzyl) benzene, 2,6-two-tert-butyl group-4-methylphenol, 2,6-two-tert-butyl group-4-ethyl-phenol, 2,2 '-methylene two (4-methyl-6-tert butyl phenol), 4,4 '-sulfo--two-(3 methy 6 tert butyl phenol), 4,4 '-butylidene-two (3 methy 6 tert butyl phenol), 1,1,3-three (2-methyl-4-hydroxyl-5-tert-butyl-phenyl) butane, 1,3,5-three (4-hydroxybenzyl) benzene and four [methylene-3-(3,5 '-two-tert-butyl group-4 '-hydroxy phenyl propionic ester)] methane etc.

As ultraviolet light absorber, for example can enumerate the benzotriazole system of 2-(the 2-hydroxyl-3-tert-butyl group-5-aminomethyl phenyl)-5-chlorobenzotriazole etc.;

The benzophenone series of 2-hydroxyl-4-octyl group dihydroxy benaophenonel etc.;

2,4-two-tert-butyl-phenyl-3, the benzoic ether of 5-two-tertiary butyl-4-hydroxy benzoic ether etc. is a ultraviolet light absorber;

The triazine of 2-(4,6-diphenyl-1,3,5-triazines-2-yl)-5-hexyl hydroxyl phenol etc. is a ultraviolet light absorber etc.

As anti-coagulants, for example can enumerate sodium polyacrylate etc.

As organic amine compound, for example can enumerate the monoalkyl amine of n-propylamine, isopropylamine, n-butylamine, isobutyl amine, sec-butylamine, tert-butylamine, n-amylamine, n-hexylamine, positive heptyl amice, n-octyl amine, positive nonyl amine, n-Decylamine, n-undecane base amine, dodecyl amine etc.;

The monocycle alkyl amine of cyclohexylamine, 2-methyl cyclohexylamine, 3-methyl cyclohexylamine, 4-methyl cyclohexylamine etc.;

The dialkyl amine of methyl ethylamine, diethylamine, methyl-n-pro-pyl amine, ethyl-n-pro-pyl amine, two-n-pro-pyl amine, diisopropylamine, di-n-butyl amine, diisobutyl amine, two-sec-butylamine, two-tert-butylamine, two-n-pentyl amine, two-n-hexyl amine etc.;

The monoalkyl monocycle alkyl amine of methylcyclohexyl amine, ethyl cyclo-hexylamine etc.;

The bicyclic alkyl amine of dicyclohexyl amine etc.;

The trialkyl amines of dimethylethyl amine, methyl diethylamide, triethylamine, dimethyl-n-pro-pyl amine, diethyl-n-pro-pyl amine, methyl two-n-pro-pyl amine, ethyl two-n-pro-pyl amine, three-n-pro-pyl amine, triisopropylamine, three-n-butylamine, triisobutyl amine, three-sec-butylamine, three-tert-butylamine, three-n-pentyl amine, three-n-hexyl amine etc.;

The dialkyl group monocycle alkyl amine of dimethylcyclohexylam,ne, diethyl cyclo-hexylamine etc.;

The monoalkyl bicyclic alkyl amine of methyl bicyclic hexyl amine, ethyl dicyclohexyl amine, thricyclohexyl amine etc.;

The monoalkanolamine class of 2-ethylaminoethanol, 3-amino-1-propyl alcohol, 1-amino-2-propyl alcohol, 4-amino-1-butanols, 5-amino-1-amylalcohol, 6-amino-1-hexanol etc.;

The mononaphthene alcamines of 4-amino-1-cyclohexanol etc.;

The dialkanol amine of diethanolamine, two-n-propanol amine, diisopropanolamine, two-normal butyl alcohol amine, two isobutyl hydramine, two-n-amyl alcohol amine, two-n-hexyl alcohol amine etc.;

The two cyclic alkanol amines of two (4-cyclohexanol) amine etc.;

Three alkanol amines of triethanolamine, three-n-propanol amine, triisopropanolamine, three normal butyl alcohol amine, three isobutyl hydramine, three-n-amyl alcohol amine, three-n-hexyl alcohol amine etc.;

The three cyclic alkanol amines of three (4-cyclohexanol) amine etc.;

3-amino-1,2-propylene glycol, 2-amino-1, ammediol, 4-amino-1,2-butylene glycol, 4-amino-1,3-butylene glycol, 3-dimethylamino-1,2-propylene glycol, 3-diethylamino-1,2-propylene glycol, 2-dimethylamino-1, ammediol, 2-diethylamino-1, the amino-alkane glycols of ammediol etc.;

4-amino-1,2-cyclohexanediol, 4-amino-1, the amino loop chain alkane glycols of 3-cyclohexanediol etc.;

The cyclanone methyl alcohol class that contains amino of 1-amino cyclopentyl ketone methyl alcohol, 4-amino cyclopentyl ketone methyl alcohol etc.;

The loop chain alkane methyl alcohol class that contains amino of the amino cyclohexanone methyl alcohol of 1-, the amino cyclohexanone methyl alcohol of 4-, 4-dimethylamino cyclopentane methyl alcohol, 4-diethylamino cyclopentane methyl alcohol, 4-dimethylamino cyclohexane methanol, 4-diethylamino cyclohexane methanol etc.;

The aminocarboxylic acids of Beta-alanine, 2-aminobutyric acid, 3-aminobutyric acid, 4-aminobutyric acid, the amino different acetate of 2-, the amino different acetate of 3-, 2-aminovaleric acid, 5-aminovaleric acid, 6-aminocaprolc acid, 1-1-aminocyclopropane-1-carboxylic acid, 1-aminocyclohexane carboxylic acid, 4-aminocyclohexane carboxylic acid etc.;

Aniline, o-toluidine, a methylaniline, to methylaniline, to ethylaniline, to n-propylbenzene amine, cumidine, to n-butyl aniline, p-tert-butyl-aniline, 1-naphthyl aniline, 2-naphthyl aniline, N, accelerine, N, the N-diethylaniline, to methyl-N, the aromatic amine of accelerine etc.;

Adjacent aminobenzyl alcohol, an aminobenzyl alcohol, PAB alcohol, to the dimethylamino benzyl alcohol, to the aminobenzyl alcohols of diethylamino benzyl alcohol etc.;

O-aminophenol, m-aminophenol, para-aminophenol, to dimethylamino phenol and to the amino phenols of diethylamino phenol etc.;

Gavaculine, p-aminobenzoic acid, ESCAROL 507 and to aminobenzoic acids of diethyl amino yl benzoic acid etc. etc.

By adding organic amine compound, can make when developing and on the substrate of unexposed portion, not produce residue, and can give pixel with the connecting airtight property excellence of substrate.

As (H) hardening agent, for example can enumerate, by heating, with carboxyl reaction in (C) adhesive resin, with (C) the crosslinked compound of adhesive resin; Polymerization separately, make compound that colored pattern solidifies etc., for example, can enumerate, epoxy compound and oxetane compound etc. preferably use oxetane compound.

Herein, as epoxy compound, for example can enumerate, bisphenol-A is an epoxy resin, hydrogenated bisphenol A is an epoxy resin, Bisphenol F is an epoxy resin, A Hydrogenated Bisphenol A F is an epoxy resin, phenolic resin varnish type epoxy resin, other fragrant family epoxy resin, alicyclic ring family epoxy resin, hetero ring type epoxy resin, glycidol ether is a resin, glycidyl amine is a resin, epoxidation wet goods epoxy resin, or the brominated derivative of these epoxy resin, aliphatics beyond epoxy resin and the brominated derivative thereof, alicyclic or aromatic epoxy compound, the epoxide of (being total to) polymers of butadiene, the epoxide of (being total to) polymers of isoprene, (being total to) polymers of diglycidyl (methyl) acrylate, three-glycidyl chlorinated isocyanurates etc.

As oxetane compound, for example can enumerate carbonic acid dioxetane, dimethylbenzene dioxetane, adipate dioxetane, terephthalate dioxetane and cyclohexane dicarboxylic acid dioxetane etc.

As hardening agent, when containing epoxy compound, oxetane compound etc., preferably contain the compound of the oxetanes skeleton ring-opening polymerization of the epoxy radicals that can make epoxy compound, oxetane compound.As this compound, can enumerate polybasic carboxylic acid and polybasic acid anhydride class etc.

As polybasic carboxylic acid system, for example can enumerate phthalic acid, 3,4-dimethyl phthalic acid, different phthalic acid, terephthalic acid (TPA), pyromellitic acid, trimellitic acid, 1,4,5,8-naphthalene tetracarboxylic acid, 3,3 ' 4, the aromatic series polybasic carboxylic acid class of 4 '-benzophenone tetrabasic carboxylic acid etc.;

Succinic acid, glutaric acid, hexane diacid, 1,2,3, the aliphatics polybasic carboxylic acid class of 4-BTCA, maleic acid, fumaric acid, itaconic acid etc.;

Hexahydro-phthalic acid, 3,4-dimethyl tetrahydro phthalic acid, the different phthalic acid of hexahydro, hexahydroterephthalic acid, 1,2,4-cyclopentane tricarboxylic acids, 1,2,4-cyclohexane tricarboxylic acids, cyclopentane tetrabasic carboxylic acid, 1,2,4, the alicyclic polybasic carboxylic acid class of 5-cyclohexane tetrabasic carboxylic acid etc. etc.

As the polybasic acid anhydride class, for example can enumerate phthalic anhydride, pyromellitic acid acid anhydride, trimellitic anhydride, 3,3 ', 4, the aromatic series polybasic acid anhydride class of 4 '-benzophenone tetracarboxylic dianhydride etc.;

Itaconic anhydride, succinic anhydride, citraconic anhydride, dodecenyl succinic anhydride, tricarballylic acid acid anhydride, maleic anhydride, 1,2,3, the aliphatics polybasic acid anhydride class of 4-butane tetracarboxylic acid dianhydride etc.;

Hexahydro phthalic anhydride, 3,4-dimethyl tetrahydro phthalic anhydride, 1,2,4-cyclopentane tricarboxylic acid anhydride, 1,2,4-cyclohexane tricarboxylic acid anhydride, cyclopentane tetracarboxylic dianhydride, 1,2,4, the alicyclic polybasic acid anhydride class of 5-cyclohexane tetracarboxylic dianhydride, humic acid anhydrides (acid of Ha イミ Star Network), nadic anhydride (acid of No water Na ジ Application) etc.;

The carboxyanhydrides that contains ester group of ethylene glycol bisthioglycolate benzenetricarboxylic acid (トリメリテイト), glycerine three benzenetricarboxylic acid acid anhydrides (トリメリテイト) etc.; Deng.

As carboxyanhydrides, can use commercially available prod as epoxy curing agent.As above-mentioned epoxy curing agent, for example can enumerate commodity by name アデカ Ha one De Na one EH-700 (Asahi Electro-Chemical Co. Ltd's manufacturings), リカシ Star De HH and MH-700 (be new Japanese physics and chemistry company manufacturing) etc.

Hardening agent can be used singly or two or more kinds in combination.

As using cured composition for color of the present invention, form the method for patterning of color filter, for example can enumerate, cured composition for color of the present invention (for example is coated on substrate or other resin bed, earlier at other cured composition for color layers that form on the substrate etc.) on, remove volatile ingredient such as desolvate, form dyed layer, see through photomask, make this dyed layer exposure, develop, as required, heating again, promptly so-called photolithograph method, or use ink discharge device, cured composition for color is coated on substrate or other resin bed, and removing desolvates waits volatile ingredient, formation dyed layer, by at least a being cured in heating or the exposure, promptly so-called ink-jet method.

By the present invention, can make the color filter of brightness and contrast excellence.The color filter that so obtains is applicable to liquid crystal indicator.

Embodiment

By the following examples the present invention is further specified.

Synthesis example 1

Synthesizing of＜colorant (A-1) 〉

In the four-hole boiling flask of 1000mL, add tetrachloro phthalonitrile 106.4g (400 mM), zinc chloride 14.3g (105 mM), urea 84.0g (3000 mM), ammonium molybdate tetrahydrate 19.9g (30 mM) and methylnaphthalene n100mL, under nitrogen environment, 200 ℃ were heated 6 hours.Filter to take out precipitate, earlier with methyl alcohol, use 60 ℃ of warm water cleanings again, then, 60 ℃ of drying under reduced pressure obtain ten chlordene Phthalocyanine Zinc 29.7g.

Then, in the four-hole boiling flask of 500mL, mix anhydrous Aluminum chloride 90.7g (680 mM), sodium chloride 11.7g (200 mM) at 40 ℃, adding ten chlordene Phthalocyanine Zinc 25.0g (22 mM) stirs, dropping liquid bromine 60.0g (751 mM) then, heat to 130 ℃ with 20 hours, kept 1 hour.The reactant taking-up that obtains is put in the water, separates out the rough pigment of chlorination bromination phthalocyanine.Filter the thick graining paste of this chlorination bromination phthalocyanine, clean with 1% niter cake aqueous solution then then with 60 ℃ of warm water cleanings, use 60 ℃ of warm water cleanings again, then, 60 ℃ of drying under reduced pressure obtain the rough pigment made from extra care of chlorination bromination phthalocyanine of 21.3g.

Then, rough pigment 20g of chlorination bromination phthalocyanine that aforesaid operations is obtained and sodium chloride 60g and the diethylene glycol 20g kneading machine of packing into, 90 ℃ ground in 5 hours after, be fetched into 80 ℃ of aqueous solution of 100 weight portions, stir after 30 minutes and filter, with 60 ℃ of warm water cleanings, 60 ℃ of drying under reduced pressure, pulverizing obtain the chlorination zinc bromide phthalocyanine color of 12.8g.

To the chlorination zinc bromide phthalocyanine color that obtains, with flask burn processing ion chromatography analysis, the result is that the substituent ratio on the zinc phthalocyanine frame is bromine 14.6, chlorine 1.4, hydrogen 0.

Synthesis example 2

Synthesizing of＜colorant (A-2) 〉

In the four-hole boiling flask of 1000mL, add sulfuryl chloride 89.1g (660 mM), anhydrous Aluminum chloride 90.7g (680 mM), sodium chloride 12.3g (210 mM), mix down at 40 ℃, adding zinc phthalocyanine 25.0g (43.3 mM) stirs, under agitation splash into bromine 60.0g (751 mM) then, heat to 130 ℃ with 20 hours, kept 1 hour.The reactant taking-up that obtains is put in the water, separates out the rough pigment of chlorination bromination phthalocyanine.Filter the thick graining paste of this chlorination bromination phthalocyanine, clean with 1% niter cake aqueous solution then then with 60 ℃ of warm water cleanings, use 60 ℃ of warm water cleanings again, then, 60 ℃ of drying under reduced pressure obtain the rough pigment made from extra care of chlorination bromination phthalocyanine of 22.5g.

Then, rough pigment 20g of chlorination bromination phthalocyanine that aforesaid operations is obtained and sodium chloride 60g and the diethylene glycol 20g kneading machine of packing into, 90 ℃ ground in 5 hours after, taking-up is put into 80 ℃ of aqueous solution of 100 weight portions, stir after 30 minutes and filter, with 60 ℃ of warm water cleanings, 60 ℃ of drying under reduced pressure, pulverizing obtain the chlorination zinc bromide phthalocyanine color of 14.3g.

To the chlorination zinc bromide phthalocyanine color that obtains, with flask burn processing ion chromatography analysis, the result is that the substituent ratio on the zinc phthalocyanine frame is bromine 13.4, chlorine 2.2, hydrogen 0.4.

Synthesis example 3

Synthesizing of＜colorant (A-3) 〉

Synthesizing of the barbiturates azo based dye of formula (2-4) expression

300g water is joined 2 of formula (27) expression, 2 '-biphenylamine disulfonic acid (moisture 30%) 30g (61 mM), then, under ice-cooled, regulating pH with 30% sodium hydrate aqueous solution is 7～8.Below operate in and carry out under ice-cooled.Add sodium nitrite 12.6g (183 mM), stirred 30 minutes.35% hydrochloric acid that slowly adds 38.1g, become brown solution after, stirred 2 hours.In reaction solution, add the aqueous solution that obtains at the water of 57.4g by the acid amides sulfuric acid dissolution of 5.3g, stir, obtain containing the suspension of diazo salt.

N in formula (28) expression adds entry 372g among the N '-dimethyl barbituric acid 18.6g (146 mM), and ice-cooled following, regulating pH with 30% sodium hydrate aqueous solution is 8～9 then.

Below operate in and carry out under ice-cooled.Stir above-mentioned barbiturates aqueous alkali, behind the solution that becomes colorless, with 30% sodium hydrate aqueous solution regulate pH to 8～9 on one side, drip with pump on one side and contain the suspension of diazo salt.Dropping liquid stirred 3 hours after finishing again, obtained yellow suspension.The yellow solid that filtration is obtained is 60 ℃ of dryings under reduced pressure, obtain the azo-compound 15g (21 mMs, yield 34%) of formula (29) expression.

In possessing the flask that cooling tube and stirring apparatus are arranged, azo-compound 5g (7 mM), chloroform 50g and the N of adding formula (29) expression, dinethylformamide 2g (3 mM), stir and maintain 20 ℃ and following on one side, dropping liquid adds thionyl chloride 6g (54 mM) on one side.Dropping liquid is warming up to 50 ℃ after finishing, and synthermal keeping 5 hours makes its reaction, is cooled to 20 ℃ then.On one side stir cooled reaction solution, maintain 20 ℃ and following, on one side dropping liquid add the mixed liquor of 3-aminophenyl butane 3g (20 mM) and triethylamine 10g (103 mM).Synthermal then stirring 5 hours makes its reaction.Then heat up in a steamer the solvent of dereaction potpourri, add small amount of methanol then, strong agitation with rotary evaporator.In the mixed liquor of acetate 29g and ion exchange water 300g, add this potpourri while stir, make crystallization separate out.The crystallization that filtration is separated out is cleaned with ion exchange water, and 60 ℃ of drying under reduced pressure obtain the azo-compound 6g (6 mMs, yield 78%) that formula (7-4) is represented.

Azo-compound for present embodiment obtains with following condition, carries out LC-MS and analyzes.

Device: Agilentl100 (manufacturing of Agilent Technology company)

Detecting device: UV detecting device: 254nm

Chromatographic column: Sumipax ODS (living fractional analysis セ Application one company makes)

Stripping solvent: the solvent system that in water-acetonitrile mixed solvent, has added 0.1% trifluoromethyl acetate

Calculate the content of each azo-compound from peak area.Consequently, the azo-compound that detects formula (7-4) expression is the compound of molecular weight 940, is 98% for the area fraction values of whole peak areas.

Synthesis example 4

Synthesizing of＜colorant (A-4) 〉

Synthesizing of the pyridone azo based dye of formula (3-12) expression

In 2 of formula (27) expression, add 3000g water among 2 '-biphenylamine disulfonic acid (moisture 30%) 100g (203 mM), then, under ice-cooled, regulating pH with 30% sodium hydrate aqueous solution is 7～8.Below operate in and ice-cooledly but carry out down.Add sodium nitrite 56g (812 mM), stirred 30 minutes.35% hydrochloric acid that slowly adds 150g, become brown solution after, stirred 2 hours.In reaction solution, add acid amides sulfuric acid dissolution by 38g (406 mM) in 380g water and the aqueous solution that obtains stirs, obtain containing the suspension of diazo salt.

Add entry 1000g in the 1-ethyl-3-cyano group-4-methyl-6-pyridone-2-ketone 76g (426 mM) of formula (30) expression, ice-cooled following, regulating pH with 30% sodium hydrate aqueous solution is 8～9 then.

Below operate in and carry out under ice-cooled.Stir the aqueous alkali of above-mentioned pyridinone, behind the solution that becomes colorless, with 30% sodium hydrate aqueous solution regulate pH to 8～9 on one side, dropping liquid contains the suspension of diazo salt on one side.Dropping liquid stirred 3 hours after finishing again, obtained yellow suspension.The yellow solid that filtration is obtained is 60 ℃ of dryings under reduced pressure, obtain the azo-compound 137g (204 mMs, yield 100%) of formula (31) expression.

In possessing the flask that cooling tube and stirring apparatus are arranged, azo-compound 5g (7 mM), chloroform 50g and the N of formula (31) expression that the adding aforesaid operations obtains, dinethylformamide 2.4g (33 mM), stir on one side and maintain 20 ℃ and following, on one side dropping liquid adding thionyl chloride 7g (59 mM).Dropping liquid is warming up to 50 ℃ after finishing, and synthermal keeping 5 hours makes its reaction, is cooled to 20 ℃ then.Stir cooled reaction solution on one side, maintain 20 ℃ and following, on one side dropping liquid adding 1, the mixed liquor of 5-dimethylhexylamine 4g (30 mM) and triethylamine 12g (119 mM).In 1 evening of synthermal then stirring, make its reaction.Then heat up in a steamer the solvent of dereaction potpourri, add small amount of methanol then, strong agitation with rotary evaporator.In the mixed liquor of acetate 29g and ion exchange water 300g, add this potpourri while stir, make crystallization separate out.The crystallization that filtration is separated out is cleaned with ion exchange water, and 60 ℃ of drying under reduced pressure obtain the azo-compound 6g (6 mMs, yield 80%) that formula (3-12) is represented.

For the azo-compound that present embodiment obtains, the same structure elucidation that carries out, the azo-compound of formula (3-12) expression detect and are the compound of molecular weight 944, are 58.3% for the area fraction values of whole peak areas.In addition, the azo-compound of single sulfuryl amine of formula (40) expression detects and is the compound of molecular weight 833, is 30.1% for the area fraction values of whole peak areas.

Synthesis example 5

Synthesizing of＜resin (C-1) 〉

Stirring machine is arranged, thermometer, also flow in the flask of 1000ml of cooling tube, tap funnel and gas introduction tube possessing, feed propylene glycol monomethyl ether 333g.Then,, in flask, feed nitrogen, make and be substituted by nitrogen environment in the flask by gas introduction tube.Then, after solution in the flask is warming up to 100 ℃, use tap funnel, in flask, splashed into the potpourri that constitutes by dicyclopentenyl methacrylate (FA-513M: Hitachi changes into industrial group and makes) 22.0g (0.10 mole), benzyl methacrylate 70.5g (0.40 mole), methacrylic acid 43.0g (0.5 mole), azoisobutyronitrile 3.6g and propylene glycol monomethyl ether 164g, lasting again 100 ℃ of stirrings in 5 hours after dropping liquid finishes with 2 hours.

After stirring end, in flask, import air with gas introduction tube, air ambient will be substituted by in the flask, then, in flask, add glycidyl methacrylate 35.5g[0.25 mole (with respect to the methacrylic acid that this reaction is used, mole fraction is 50 moles of %)], three dimethylaminomethyl phenol 0.9g and quinhydrones 0.145g, 110 ℃ of reactions continue 6 hours, obtain containing the solution (solid constituent 38.7 quality %, acid number 82mgKOH/g) of resin (C-1).

Acid number herein, be as in and the carboxylic acid of 1g etc. contain acidic group the necessary potassium hydroxide of condensate amount (mg) and the value measured can be tried to achieve by the potassium hydroxide aqueous solution titration of using concentration known usually.

The polystyrene conversion weight-average molecular weight of the resin that obtains (C-1) is 9,800.

The mensuration of the polystyrene conversion weight-average molecular weight of above-mentioned (C-1) adhesive resin is used the GPC method, carries out according to following condition.

Device: HLC-8120GPC (eastern ソ one company make)

Post: TSK-GELG2000HXL

Column temperature: 40 ℃

Solvent: THF

Flow velocity: 1.0mL/min

Test solution solid component concentration: 0.001～0.01 quality %

Injection rate IR: 50 μ L

Detecting device: RI

Proofread and correct and use standard substance: TSK standard styrene F-40, F-4, F-1, A-2500, A-500 (eastern ソ one company manufacturing)

Synthesis example 6

Synthesizing of＜resin (C-2) 〉

Possess stirring machine is arranged, thermometer, also flow cooling tube, tap funnel and nitrogen ingress pipe flask in, feed propylene glycol monomethyl ether 182g.Then,, in flask, feed nitrogen, make and be substituted by nitrogen environment in the flask by gas introduction tube.Then, solution in the flask is warming up to 100 ℃, splash in the potpourri that monomethacrylates (Hitachi changes into company and makes FA-513M) 22.0g (0.10 mole) and propylene glycol monomethyl ether 136g by benzyl methacrylate 70.5g (0.40 mole), methacrylic acid 43.0g (0.5 mole), tricyclodecane skeleton constitute and added 2, the solution of 2 '-azoisobutyronitrile 3.6g continues down to stir at 100 ℃ again.

After stirring end, to be substituted by air ambient from nitrogen in the flask, in flask, add glycidyl methacrylate 35.5g[0.25 mole (carboxyl with respect to the methacrylic acid of this reaction use is 50 moles of %)], three dimethylaminomethyl phenol 0.9g and quinhydrones 0.145g, 110 ℃ of reactions, obtain containing the solution (solid constituent 28.9 quality %, acid number 79mgKOH/g) of resin (C-2).

Similarly measure the weight-average molecular weight of polystyrene conversion with resin (C-1).The weight-average molecular weight of the polystyrene conversion of resin (C-2) is 3.0 * 10 ⁴

The composition that present embodiment uses is as follows, below simply expression sometimes.

(A-1) colorant (pigment): the pigment that synthesis example 1 obtains

(A-2) colorant (pigment): the pigment that synthesis example 2 obtains

(A-3) colorant (dyestuff): the pigment that synthesis example 3 obtains

(A-4) colorant (dyestuff): the pigment that synthesis example 4 obtains

(A-5) colorant (dyestuff): the compound (C.I. solvent yellow-162) of formula (3-1) expression

(A-6) colorant (dyestuff): the compound of formula (21) expression (anthocyanin based dye: NK-3212: woods protobiochemistry research institute makes)

(A-7) colorant (pigment): C.I. pigment yellow-150

(A-8) colorant (dyestuff): the compound of formula (A-8) expression

(A-9) colorant (dyestuff): the compound of formula (A-9) expression

(A-10) colorant (pigment): C.I. naphthol green 58

(B-1) polymerizable compound: DPHA (Japanese chemical drug corporate system is made)

(C-1) adhesive resin: the resin that synthesis example 5 obtains (C-1) (the propylene glycol monomethyl ether solution of solid constituent 38.7 quality %)

(C-2) adhesive resin: the resin that synthesis example 6 obtains (C-2) (the propylene glycol monomethyl ether solution of solid constituent 28.9 quality %)

(D-1) polymerization initiator: 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone

(D-2) polymerization initiator: OXE-01 (manufacturing of チバスペシヤリテイケミカ Le ズ company)

(E-1) polymerization causes auxiliary agent: 4,4 '-two (diethylamino) benzophenone

(F-1) solvent: propylene glycol monomethyl ether

(F-2) solvent: propylene glycol monomethyl ether

(F-3) solvent: 3-ethoxyl ethyl propionate

(G-1) surfactant: メガ Off ア Star Network F475 (big Japanese イ Application キ chemical industrial company make)

Pigment dispersing agent 1: デイスパ one PVC Star Network 2001 (manufacturing of PVC Star Network ケミ one company) (mixed solution of propylene glycol monomethyl ether, propylene glycol monomethyl ether and the ethylene glycol monobutyl ether of solid constituent 46.0 quality %)

Embodiment 1

[modulation of pigment dispersion 1]

(A-1) 8.500 mass parts

(C-1) 6.589 mass parts (solid constituent scaled value: 2.550 mass parts)

(pigment dispersing agent) 7.761 mass parts (solid constituent scaled value: 3.570 mass parts)

(F-1) 13.575 mass parts

(F-2) 13.575 mass parts

With pack into mayonnaise (the マヨネ one ズ) bottle of capacity 143ml of above-mentioned composition, add zirconium oxide bead 166.500 mass parts of diameter 0.5mm again, airtight,, filter and obtain pigment dispersion 1 after 20 hours in paint bobbing machine (ペイ Application トコ Application デイシヨ Na one) vibration.

[modulation of cured composition for color 1]

Then, each composition is mixed, obtain cured composition for color 1 by following prescription.

Pigment dispersion 1 3.775 mass parts

(A-6) 0.200 mass parts

(B-1) 0.399 mass parts

(C-1) 1.050 mass parts (solid constituent scaled value: 0.406 mass parts)

(D-1) 0.142 mass parts

(E-1) 0.047 mass parts

(F-1) 4.000 mass parts

(F-3) 0.385 mass parts

(G-1) 0.001 mass parts

[formation of coated film]

Then use spin-coating method, go up the above-mentioned cured composition for color that obtains of coating at glass (manufacturing of EAGLE2000: コ one ニ Application グ company) and made the volatile ingredient volatilization in 1,100 ℃, 3 minutes, form the cured composition for color film.After the cooling, to this cured composition for color film irradiation i line (wavelength 365nm), exposure.The i line source uses extra-high-pressure mercury vapour lamp, shines as directional light.The irradiation light quantity is 200mJ/cm ²Then, carry out 220 ℃, 20 minutes back baking (post bake), obtain the cured composition for color film of CIE-XYZ color specification system, y=0.600.The thickness of cured composition for color film is 2.2 μ m.

[estimating 1] brightness evaluation

Measure the colourity of the cured composition for color film obtain with colour examining machine (manufacturing of OSP-SP-200:OLYMPUS company), the result is x=0.289, y=0.600, Y (brightness)=58.62.

[estimating 2] contrast evaluation

With contrast colour examining machine (CT-1; Kettle slope motor company makes), 10000 to be blank value, measure the contrast value of the cured composition for color film that obtains, be 9180.

Metewand as the contrast of cured composition for color film, contrast value is in the words more than 8000, then think and do not have depolarized property basically, demonstrate the good characteristic of color filter, contrast value surpasses 5800, below 8000, can find some depolarized property, but it is no problem in the practicality of color filter, contrast value can confirm tangible depolarized property below 5800, is problematic as color filter.

[estimating 3] thermotolerance evaluation

Measure the colourity of the cured composition for color film that obtains with colour examining machine (manufacturing of OSP-SP-200:OLYMPUS company).

Then, with the cured composition for color film that obtains, in baking oven, the following 230 ℃ of heating of air ambient 120 minutes, the same colourity of measuring the cured composition for color film after heating is tried to achieve aberration (the Δ Eab before and after heating ^*), be 4.6.

As the metewand of aberration, Δ Eab ^*Below 5, then thinking does not have form and aspect to change basically, demonstrates the good characteristic of color filter, Δ Eab ^*Surpass 5,10 below, can find some form and aspect variations, but no problem in the practicality of color filter, Δ Eab ^*More than 10, can confirm tangible form and aspect and change, be problematic as color filter.

[estimating 4] photostability evaluation

On the cured composition for color film that obtains, (COLOREDOPTICAL GLASS L38: ホヤ company makes configuration UV-preventing (カ Star ト) optical filter; Cover the following light of 380nm.), with light fastness test machine (SUNTEST CPS+: Japan smart machine company makes) 48 hours xenon lamp of irradiation.

Measuring the colourity of postradiation cured composition for color film, try to achieve the aberration behind the pre-irradiation, is 2.8.

As the metewand of aberration, the same, Δ Eab ^*Below 5, then thinking does not have form and aspect to change basically, demonstrates the good characteristic of color filter, Δ Eab ^*Surpass 5,10 below, can find some form and aspect variations, but no problem in the practicality of color filter, Δ Eab ^*More than 10, can confirm tangible form and aspect and change, be problematic as color filter.

Embodiment 2～6

The composition of cured composition for color is changed to table 1, in addition, obtain cured composition for color 2～6 in the same manner with embodiment 1.

In addition, for colorant (A-2) and (A-7), except the colorant (A-1) with [modulation of pigment dispersion 1] change to separately (A-2) and (A-7), the dispersion that similarly makes paints is used for estimating.

Estimate the cured composition for color 2～6 that obtains in the same manner with embodiment 1, the result is as shown in table 2.

[table 1]

[table 2]

Embodiment 7

[modulation of pigment dispersion 2]

(A-10) 40 mass parts

(pigment dispersing agent) 5 mass parts

(F-2) 137 mass parts

After the mixing,, obtain pigment dispersion 2 with the abundant dispersed color of sand mill.

[modulation of cured composition for color 7]

Then, each composition is mixed, obtain cured composition for color 7 by following prescription.

Pigment dispersion 2 182 mass parts

(A-8) 24 mass parts

(B-1) 50 mass parts

(C-2) 157 mass parts

(D-2) 15 mass parts

(F-2) 289 mass parts

[formation of pattern]

On the glass substrate (manufacturing of イ one グ Le 2000: コ one ニ Application グ company) of 2 inches of the length of sides,, then, carry out 100 ℃, 3 minutes preliminary dryings with spin-coating method coating cured composition for color 7.After the cooling, order has been coated with the substrate of cured composition for color and the 100 μ m that are spaced apart of the quartz glass system photomask with pattern, with exposure machine (TME-150RSK; トプコ Application company makes), under atmospheric environment, with 150mJ/cm ²Exposure (365nm benchmark) irradiates light.After the rayed, with above-mentioned film to be immersed in contain the water system developer solution that nonionic is surfactant 0.12% and potassium hydroxide 0.04%, 23 ℃ of dippings developed in 80 seconds, after the washing, carried out 220 ℃ of back bakings of 20 minutes (post bake) in baking oven.Put cold after, with determining film thickness device (DEKTAK3; Japan vacuum technique company makes) measure the thickness of the cured pattern that obtains, be 2.2 μ m.

[evaluation]

To filming on the glass substrate that obtains, use colour examining machine (manufacturing of OSP-SP-200:OLYMPUS company), adopt illuminant-C to measure the xy chromaticity coordinate (x, y) and the brightness (Y) of the XYZ color specification system of CIE, with contrast meter (color colour difference meter BM-5A; トプコ Application company makes) the mensuration contrast.The result is as shown in table 3.For thermotolerance evaluation and photostability evaluation, also obtained good result.

Embodiment 8

Except (A-8) being become (A-9), obtain cured composition for color 8 similarly to Example 7.Similarly to Example 7, form the pattern of thickness 2.2 μ m, estimate.The result is as shown in table 3.For thermotolerance evaluation and photostability evaluation, also obtained good result.

[table 3]

	Embodiment 7	Embodiment 8
	Embodiment 7	Embodiment 8	x	0.296	0.296
y	0.596	0.596	x	0.296	0.296
y	0.596	0.596	Y (brightness)	56.1	55.1
Contrast	7922	7810	Y (brightness)	56.1	55.1

Embodiment 9

Use ink discharge device, cured composition for color 1～8 is coated on the have side slope substrate of (bank), form painted filming.

The industry utilizability

Use cured composition for color of the present invention, can make the colour filter of brightness and contrast excellence.

Claims

1. cured composition for color contains (A) colorant and (B) polymerizable compound, and (A) colorant is the pigment that contains formula (1) expression and the colorant of weld,

In the formula (1), A ¹～A ¹⁶Independent separately expression hydrogen atom, chlorine atom or bromine atoms.

2. the described cured composition for color of claim 1, wherein, weld contains and is selected from barbiturates azo based dye, pyridone azo based dye, pyrazolone azo based dye, Kui phthalein ketone based dye and the anthocyanin based dye at least a kind dyestuff.

3. cured composition for color as claimed in claim 2, wherein, barbiturates azo based dye is the dyestuff of formula (2) expression,

In the formula (2), T ¹And T ²Independent separately expression oxygen atom or sulphur atom,

R ³¹～R ³⁴Independent separately expression hydrogen atom, can contain substituent carbon number 1～10 aliphatic alkyl, can contain substituent carbon number 6～20 aryl, can contain the aralkyl of substituent carbon number 7～20, maybe can contain the acyl group of substituent carbon number 2～10

R ³⁵～R ⁴²Independent separately expression hydrogen atom, the aliphatic alkyl of carbon number 1～10, alkoxy, carboxyl, sulfo group, sulfamoyl or the N position-replacement sulfamoyl of carbon number 1～8, the contained hydrogen atom of this aliphatic alkyl can replace with halogen atom.

4. cured composition for color as claimed in claim 2, wherein, pyridone azo based dye is the salt of compound of compound, formula (3) expression of formula (3) expression or the formed dipolymer of compound of formula (3) expression,

In the formula (3), Z represents to contain in 1 or 2 alkoxy, hydroxyl, carboxyl, carbamyl, sulfo group, sulfamoyl and the N position-replacement sulfamoyl that is selected from halogen atom, the aliphatic alkyl that can contain substituent carbon number 1～12, carbon number 1～8 at least a kind substituent phenyl; Or contain in 1～3 alkoxy, hydroxyl, carboxyl, carbamyl, sulfo group, sulfamoyl and N position-replacement sulfamoyl that is selected from halogen atom, the aliphatic alkyl that can contain substituent carbon number 1～12, carbon number 1～8 at least a kind substituent naphthyl

R ²¹Aliphatic alkyl, carboxyl or the trifluoromethyl of the carbon number 1～10 of expression hydrogen atom, straight chain shape, a chain or ring-type,

R ²²Expression hydrogen atom, cyano group, carbamyl, N position-substituted-amino formoxyl, sulfamoyl or sulfo group,

R ²³The expression hydrogen atom; the straight chain shape that can contain substituent carbon number 1～10; prop up the aliphatic alkyl of chain or ring-type; the aryl that can contain substituent carbon number 6～30; the aralkyl that can contain substituent carbon number 7～20; the heterocyclic radical that maybe can contain substituent carbon number 3～20; carbamyl; N position-substituted-amino formoxyl; the alkoxy carbonyl group that can contain substituent carbon number 2～20; the aryl carbonyl oxygen that can contain substituent carbon number 7～30; the acyl group that can contain substituent carbon number 2～20; the aliphatics sulfonyl that can contain substituent carbon number 1～30 maybe can contain the aryl sulfonyl of substituent carbon number 6～30.

5. as any described cured composition for color in the claim 1～4, wherein, also contain (C) adhesive resin.

6. pattern, described pattern uses any described cured composition for color of claim 1～5, forms with photolithograph method or ink-jet method.

7. a color filter contains the described pattern of claim 6.

8. a liquid crystal indicator possesses the described color filter of claim 7.