CN101598897B

CN101598897B - Colored curing composition, pattern curing colored layer by using composition, color filter and liquid crystal display device

Info

Publication number: CN101598897B
Application number: CN200910141597.0A
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: 2014-05-14
Anticipated expiration: 2029-06-01
Also published as: KR101741653B1; KR20090126192A; JP2015057654A; JP2015061907A; TW201001067A; CN103869613B; JP5931319B2; TWI456345B; JP6028774B2; CN101598897A; JP5910691B2; CN103869613A; JP2010168531A

Abstract

The present invention provides a color solidification property composition which contains colorant (A) and colorant polymeric compound (B), wherein the colorant (A) contains a paint represented with formula (1) and a yellow dye. The formula is shown in the description, wherein A (1) to A (16) respectively and independently represent hydrogen atom, chlorine atom and bromine atom.

Description

Cured composition for color, use its pattern cured dyed layer, color filter and liquid crystal indicator

Technical field

The present invention is about the cured composition for color of 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 seeing through the light of color filter, therefore, compared with the 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 object of this invention is to provide the cured composition for color of the color filter that can form brightness and contrast excellence.

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

, the invention provides following invention.

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

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

2. the cured composition for color as described in 1, 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 anthocyanin based dye.

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

[in formula (2), T ¹and T ²independent oxygen atom or the sulphur atom of representing separately.

R ³¹～R ³⁴separately the independent aliphatic alkyl that represents hydrogen atom, can contain substituent carbon number 1～10, 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 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 of representing separately.The hydrogen atom that this aliphatic alkyl is contained, available halogen atom replaces.]

4. the cured composition for color as described in 2, wherein, the dipolymer that the salt of the compound that pyridone azo based dye represents for formula (3), the compound that formula (3) represents or the compound that formula (3) represents form.

[in formula (3), Z represents: contain in 1 or 2 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 the substituent phenyl of at least a kind; 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 the substituent naphthyl of at least a kind.

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

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

R ²³represent hydrogen atom, can contain the straight chain shape of substituent carbon number 1～10, prop up the aliphatic alkyl of chain or ring-type, can contain the aryl of substituent carbon number 6～30, can contain the aralkyl of substituent carbon number 7～20, can contain the heterocyclic radical of substituent carbon number 3～20, carbamyl, N position-substituted-amino formoxyl, can contain the alkoxy carbonyl group of substituent carbon number 2～20, can contain the aryl carbonyl oxygen of substituent carbon number 7～30, can contain the acyl group of 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. the cured composition for color as described in any one in 1～4, wherein, also contains (C) adhesive resin.

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

7. a color filter, contains the pattern described in 6.

8. a liquid crystal indicator, possesses the color filter described in 7.

Embodiment

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

In formula (1), A ¹～A ¹⁶the substituent quantity representing, preferably chlorine atom is 0～6, bromine atoms is 10～16, and chlorine atom and bromine atoms and be 10～16, more preferably chlorine atom is 0～3, bromine atoms is 13～16, and chlorine atom and bromine atoms and be 13～16, further preferably 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 form and aspect are more yellow, while being used as color filter, can in the situation that not reducing color rendering scope, improve brightness, therefore comparatively desirable.

The manufacture method of pigment representing as formula (1), the method that the communiques such as No. 2007-284589, No. 2007-284592, JP, No. 2007-291232, JP, No. 2008-19383, JP that can use Japanese Patent Laid-Open are recorded.

The content of the pigment that formula (1) represents, for (A) colorant full dose, mass fraction is 0.5～99.5 quality %, preferably 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 anthocyanin based dye the dyestuff of at least a kind.

As barbiturates azo based dye, be not particularly limited, can use known material, the barbiturates azo based dye that preferably uses formula (2) to represent.

T ¹and T ²independent oxygen atom or the sulphur atom of representing separately, 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, preferably 2～8, more preferably 3～6.As the aliphatic alkyl of 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 (preferably carbon number 1～4) or the thioalkoxy group of carbon number 1～8 (preferably carbon number 1～4) replace.As 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 be without replacement, the substituting group of the group that also can contain aliphatic alkyl, alkoxy, carboxyl, sulfo group or contain ester bond etc.The carbon number of above-mentioned aryl, comprises substituent carbon number, and preferably 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) 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 preferably 7～10.As the aralkyl of carbon number 7～20, can enumerate benzyl and phenethyl etc.

R ³¹～R ³⁴the acyl group of middle carbon number 2～10, can be without replacement, also can bonding aliphatic alkyl or the substituting group of alkoxy etc.The carbon number of acyl group, comprises substituent carbon number, and preferably 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 enumerate 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, as halogen atom, can enumerate, preferably fluorine atom.As the object lesson of the aliphatic alkyl being replaced by halogen atom, can enumerate trifluoromethyl etc.

R ³⁵～R ⁴²the carbon number of the alkoxy of middle carbon number 1～8, preferably 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, preferably N position-mono-replaces sulfamoyl, with-SO ₂nHR ¹³represent.

R ¹³represent: the acyl group that can there is the aliphatic alkyl of substituent carbon number 1～10, the aryl can with substituent carbon number 6～20, the aralkyl can with substituent carbon number 7～20 and 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 preferably 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 (preferably 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, without replacement, also can contain the substituting group of aliphatic alkyl or hydroxyl etc.The carbon number of above-mentioned aryl, comprises substituent carbon number, and preferably 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 straight chain shape or a chain.The carbon number of aralkyl, is generally 7～20, and preferably 7～10.As this kind of 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 be without replacement, can be also that the contained hydrogen atom of acyl group is replaced by aliphatic alkyl or alkoxy.The carbon number of acyl group, comprises substituent carbon number, and preferably 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 that formula (2-1)～(2-8) represents, preferred formula (2-1), formula (2-3)～(2-5), (2-7) and (2-8) compound that represents etc.

As pyridone azo based dye, be not particularly limited, can use known material, but the material that preferably uses formula (3) to represent.

R ²³represent hydrogen atom, can contain the straight chain shape of substituent carbon number 1～10, prop up the aliphatic alkyl of chain or ring-type, can contain the aryl of substituent carbon number 6～30, can contain the aralkyl of substituent carbon number 7～20, maybe can contain the heterocyclic radical of substituent carbon number 3～20, carbamyl, N position-substituted-amino formoxyl, can contain the alkoxy carbonyl group of substituent carbon number 2～20, can contain the aryl carbonyl oxygen of substituent carbon number 7～30, can contain the acyl group of 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 formula (3), the aliphatic alkyl of the carbon number 1～12 in 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 preferably 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 thering is substituent aliphatic alkyl, for example can enumerate alkoxy propyl group (3-(2 '-ethylhexyl oxygen) propyl group etc.) and 8-(carboxyl) octyl group etc.

As the alkoxy of carbon number in 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 in Z, can enumerate fluorine atom, bromine atoms, chlorine atom and iodine atom.

N position-replacement sulfamoyl in Z, available-SO ₂n (R ²⁴) R ²⁵represent.R ²⁴and R ²⁵separately the independent aliphatic alkyl that represents hydrogen atom, can contain substituent carbon number 1～16, 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 ²⁵when different, be hydrogen atom).

The aliphatic alkyl of carbon number 1～16, can be arbitrarily straight chain shape, chain or ring-type, the carbon number of aliphatic alkyl, preferably 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 aliphatic alkyl, containing substituent carbon number, be generally 1～16, preferably 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 thering is 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 there is the substituting group such as aliphatic alkyl or hydroxyl.The carbon number of aryl, comprises substituent carbon number, is generally 6～20, and preferably 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 straight chain shape or a chain.The carbon number of aralkyl, is generally 7～20, and preferably 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, without replacement, also can there is 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 preferably 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 preferably 2～8, 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 ²²represent 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 ²⁷.R ²⁶and R ²⁷represent independently of one another 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 ²⁶and R ²⁷the explanation of aliphatic alkyl, aryl, aralkyl and acyl group and object lesson and above-mentioned R 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 ²³represent hydrogen atom, can contain the straight chain shape of substituent carbon number 1～10, prop up the aliphatic alkyl of chain or ring-type, can contain the aryl of substituent carbon number 6～30, can contain the aralkyl of substituent carbon number 7～20, can contain the heterocyclic radical of substituent carbon number 3～20, carbamyl, N position-substituted-amino formoxyl, can contain the alkoxy carbonyl group of substituent carbon number 2～20, can contain the aryl carbonyl oxygen of substituent carbon number 7～30, can contain the acyl group of 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, preferably 6～20, more preferably 6～16.As the object lesson of 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 preferably 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, as carbon number, preferably 3～20, 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 without replace, also can contain substituting group, can be also ring-type.As the carbon number of alkoxy carbonyl group, be generally 2～20, preferably 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 without replacing, also can contain substituting group, as carbon number, be generally 7～30, preferably 7～20, more preferably 7～16.As aryl carbonyl oxygen, can enumerate phenyloxycarbonyl and 4-methylphenoxy carbonyl etc.

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

As R ²³aliphatics sulfonyl, can be saturated, can be also unsaturated, can be also ring-type.As carbon number, be generally 1～30, preferably 1～20, more preferably 1～16.As 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, preferably 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, preferred formula (3-1)～(3-9) compound of expression.

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

The compound that formula (3) represents, can form polymer more than dipolymer.

The polymer of formula (3), is the compound that contains the group of 2 above compounds that represent from formula (3) in 1 molecule, specifically can enumerate the compound that formula (3-12) formula (3-15) represents etc.

As pyrazolone azo based dye, be not particularly limited, can use known material, for example, the pyrazolone azo based dye that the communiques such as No. 2006-015669, can use Japanese Patent Laid-Open No. 2006-276512, No. 2005-263926, JP and JP are recorded.

Concrete, can enumerate the compound that 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) represent etc.

As Kui phthalein ketone based dye, be not particularly limited, can use known material, for example, the Kui phthalein ketone based dye that the communiques such as No. 8-171201, can use Japanese patent laid-open No. 5-39269, No. 6-220339, Unexamined Patent and Unexamined Patent are recorded.

Concrete, can enumerate the compound that 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) represent etc.

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

For example, the anthocyanin that the communique such as No. 2005-297406, can use Japanese Patent Laid-Open No. 2005-194509, No. 2007-131818, JP and JP is recorded is pigment.

Concrete, can enumerate the compound that formula (20)～(23) represent 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, in Color Index (The Society of Dyers and Colourists publication), be categorized as the compound of dyestuff, or the known dyestuff of dyeing Note (Se Ran society) record, specifically can enumerate, C.I. solvent yellow-4 (C.I.SolventYellow-4) (omits below the statement of C.I.SolventYellow, only indicates numbering.Other kind of dyes 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 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, C.I. directly yellow (DirectYellow) 2, 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. medium (Mordant) dyestuff, can enumerate the dyestuff such as C.I. medium Huang (Mordant Yellow) 5,8,10,16,20,26,30,31,33,42,43,45,56,61,62,65, C.I. medium 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. medium green (MordantGreen) 1,3,4,5,10,15,19,26,29,33,34,35,41,43,53.Preferably 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, the 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. the viridine green such as naphthol green (PigmentGreen) 7,36; Preferably 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 pigment and be dispersed in the dispersible pigment dispersion of the state in 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.

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

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

As the mean grain size of the pigment in dispersible pigment dispersion, be 10～150nm, preferably 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 %, preferably 15～90 quality %, more preferably 20～88 quality %.

Herein, the solid constituent in this instructions, refers to the composition total amount of having removed after the contained solvent of cured composition for color.

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

In addition, the content of the yellow uitramarine that cured composition for color of the present invention uses is that for the holochrome of (A) colorant full dose yellow, mass fraction is 0.5～99.5 quality %, preferably 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 uprising, therefore comparatively desirable.

As (B) polymerizable compound, can use heat or light or monomer or oligomer that both are cured, but also both and use.As monomer or oligomer, can use known material.

As the object lesson of 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, can use 18 pages of oligomer to 20 pages of records of status and prospects (シ mono-エ system シ mono-publishes) of UVEB curing technology etc.

(B) content of polymerizable compound is, for the solid constituent of cured composition for color, mass fraction is 5～90 quality % preferably, more preferably 10～85 quality %, particularly preferably 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 represents acrylic acid and/or methacrylic acid.Be derived from the content of (methyl) acrylic acid repetitive, in all repetitives of formation adhesive resin, the preferred 10mol% of mole fraction and above, 40mol% and following, more preferably 13mol% and above, 35mol% and following.

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

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

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., preferably 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 that 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) represent (still, herein, in formula (25), R ³¹represent methyl, R ³²represent hydrogen atom.Repetitive that)/N-benzyl maleimide/benzyl methacrylate multipolymer, methacrylic acid/formula (25) represent (still, herein, in formula (25), R ⁵¹represent methyl, R ⁵²represent hydrogen atom.Repetitive that)/N-N-cyclohexylmaleimide/benzyl methacrylate multipolymer, methacrylic acid/formula (24) represent (still, herein, in formula (24), R ⁵¹represent methyl, R ⁵²represent hydrogen atom.Repetitive that)/benzyl methacrylate multipolymer, formula (24) represent (still, herein, in formula (24), R ⁵¹represent methyl, R ⁵²represent hydrogen atom.Repetitive that)/benzyl methacrylate multipolymer, methacrylic acid/formula (25) represent (still, herein, in formula (25), R ⁵¹represent methyl, R ⁵²represent hydrogen atom.)/styrene/methacrylic acid two cyclopentene ester copolymers etc.

(C) acid number of adhesive resin preferably 30～150, more preferably 35～135, particularly preferably 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, conventionally can be by using potassium hydroxide aqueous solution titration try to achieve.

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

There is (C) adhesive resin of repetitive that formula (24) represents, for example, contain the repetitive that the repetitive/formula (24) from methacrylic acid represents (still, herein, in formula (24), R ⁵¹represent methyl, R ⁵²represent hydrogen atom.)/from the repetitive of benzyl methacrylate and the multipolymer forming, can pass through, methacrylic acid and benzyl methacrylate polymerization obtain 2 composition condensates, make compound that the 2 composition condensates that obtain and formula (26) represent (still, herein, in formula (26), R ⁵³represent hydrogen atom.) reaction and obtain.

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

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

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

As 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, 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, preferably 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 bisglyoxaline based compound, for example can enumerate, 2, 2 '-bis-(2-chlorphenyls)-4, 4 ', 5, 5 '-tetraphenyl bisglyoxaline, 2, 2 '-bis-(2-chlorphenyls)-4, 4 ', 5, 5 '-tetra-(4-carbon ethoxyl phenenyl) bisglyoxaline, 2, 2 '-bis-(2-chlorphenyls)-4, 4 ', 5, 5 '-tetra-(4-bromophenyl) bisglyoxaline, 2, 2 '-bis-(2-chlorphenyls)-4, 4 ', 5, 5 '-tetra-(2, 4-dichlorophenyl) bisglyoxaline, 2, 2 '-bis-(2-bromophenyls)-4, 4 ', 5, 5 '-tetraphenyl bisglyoxaline, 2, 2 '-bis-(2, 4-dichlorophenyl)-4, 4 ', 5, , 5 '-tetraphenyl bisglyoxaline, 2, 2 '-bis-(2-chlorphenyls)-4, 4 ', 5, 5 '-tetra-(m-methoxyphenyl) bisglyoxaline, 2, 2 '-bis-(2, 3-dichlorophenyl)-4, 4 ', 5, 5 '-tetraphenyl bisglyoxaline, 2, 2 '-bis-(2, 6-dichlorophenyl)-4, 4 ', 5, 5 '-tetraphenyl bisglyoxaline, 2, 2 '-bis-(2-nitre phenyl)-4, 4 ' 5, 5 '-tetraphenyl bisglyoxaline and 2, 2 '-bis-(2-aminomethyl phenyls)-4, 4 ', 5, 5 '-tetraphenyl bisglyoxaline etc., preferably 2, 2 '-bis-(2-chlorphenyls)-4, 4 ', 5, 5 '-tetraphenyl bisglyoxaline or 2, 2 '-bis-(2, 3-dichlorophenyl)-4, 4 ', 5, 5 '-tetraphenyl bisglyoxaline.

After living radical initiating agent is irradiated by light, can produce living radical.As living radical initiating agent, for example can enumerate styrax based compound, benzophenone based compound, thioxanthones based compound and oxime compound etc.

As 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 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 '-tetra-(tert-butyl hydroperoxide carbonyl) benzophenone and 2,4,6-tri-methyl benzophenone etc.

As thioxanthones based compound, for example can enumerate ITX, ITX, 2,4-diethyl thioxanthone, 2,4-bis-clopenthixal ketones and the chloro-4-propoxyl group of 1-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 p-Nitrobenzyl class, the styrax tosylate class etc. of 4-hydroxyphenyl dimethyl sulfonium p-toluenesulfonic acid ester, 4-hydroxyphenyl dimethyl sulfonium hexafluoro oxygen antimony ester (ア Application チモネ mono-ト), 4-acetoxyl group phenyl dimethyl sulfonium-p-toluenesulfonic acid ester, 4-acetyloxy phenyl methyl-benzyl sulfonium hexafluoro oxygen antimony ester, triphenylsulfonium p-toluenesulfonic acid ester, triphenylsulfonium hexafluoro oxygen antimony ester, the iodo-p-toluenesulfonic acid ester of diphenyl, diphenyl iodine hexafluoro oxygen antimony ester etc.

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

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

In 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 for promoting the compound by the polymerizable compound polymerization of (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, EDMAB, 4-dimethylaminobenzoic acid isopentyl ester, benzoic acid 2-dimethylamino ethyl ester, 4-dimethylaminobenzoic acid 2-Octyl Nitrite, N, N-dimethyl-p-toluidine, 4, 4 '-bis-(dimethylamino) benzophenone, 4, 4 '-bis-(diethylamino) benzophenone and 4, 4 '-bis-(ethylmethylamino) benzophenone etc., preferably 4, 4 '-bis-(diethylamino) benzophenone.

As alkoxy anthracene based compound, for example can enumerate 9,10-dimethoxy anthracene, EDMO, 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 as (E) polymerization, can use commercially available prod, cause auxiliary agent as commercially available (E) polymerization, for example can enumerate, commodity are called the organic amine compound of EAB-F (hodogaya chemical industrial group manufacture, 4,4 '-bis-(diethylamino) benzophenone) etc. etc.

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

While using (E) polymerization to cause auxiliary agent, its use amount is, with respect to (D) polymerization initiator of every 1 mass parts, preferably 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, 4-diox, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol list propyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, TC, diethylene glycol single-butyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ethers, propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters, propylene glycol list propyl ether acetic acid esters, methyl acetic acid cellosolve, ethyl acetic acid cellosolve, 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, methylanisole 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 ethanol class, for example can enumerate methyl alcohol, ethanol, propyl alcohol, butanols, hexanol, cyclohexanol, ethylene glycol, diacetone ethanol and glycerine etc.

As ester class, for example can enumerate ethyl acetate, acetic acid-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, Butyl Glycolate, methoxy menthyl acetate, methoxyacetic acid ethyl ester, methoxyacetic acid butyl ester, ethoxy acetate, ethoxy ethyl acetate, 3-hydroxy methyl propionate, 3-hydracrylic acid ethyl ester, 3-methoxy methyl propionate, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, 3-ethoxyl ethyl propionate, 2 hydroxy propanoic acid methyl esters, 2 hydroxy propanoic acid ethyl ester, 2 hydroxy propanoic acid propyl ester, 2-methoxy methyl propionate, 2-methoxy propyl acetoacetic ester, 2-methoxy propyl propyl propionate, 2-ethoxy-propionic acid methyl esters, 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, ALPHA-ketobutyric acid methyl esters, ALPHA-ketobutyric acid ethyl ester, 3-methoxyl butylacetic acid ester, 3-methyl-3-methoxyl butylacetic acid ester and gamma-butyrolacton etc.

As amide-type etc., for example can enumerate DMF and DMA etc.

As other solvent, for example can enumerate 1-METHYLPYRROLIDONE and dimethyl sulfoxide (DMSO) etc.

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

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

(F) content of solvent, with respect to cured composition for color, mass fraction is 70～90 quality % preferably, 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 the surfactant that contains siloxane bond etc.Specifically can enumerate, commodity are called ト mono-レシリコ mono-Application DC3PA, same to SH7PA, same to DC11PA, same to SH21PA, same to SH28PA, same to 29SHPA, same to SH30PA, polyether modified silicon oil SH8400 (ト mono-レシリコ mono-Application company manufactures), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (the シリコ of SHIN-ETSU HANTOTAI mono-Application manufacture), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, TSF4460 (the ジ mono-イ mono-シリコ of Toshiba mono-Application company manufactures) etc.

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

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

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

In 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, preferably 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 cured composition for color of the present invention, can also contain macromolecular compound beyond filling agent, (C) adhesive resin, connect airtight the 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, APTES, 3-glycidoxy-propyltrimethoxy silane, 3-epoxy the third oxygen methyl dimethoxysilane, 2-(3, 4-epoxycyclohexyl) ethyl trimethoxy silane, 3-chloropropylmethyldimethoxysilane, 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--bis-(the 6-tert-butyl group-3-methylphenol, triethylene glycol-bis-[3-(the 3-tert-butyl group-5-methyl-4-hydroxy phenyl) propionic ester], 1,6-hexanediol-bis--[3-(3,5-, bis--tert-butyl-hydroxy phenyl) propionic ester], pentaerythrite-tetra-[3-(3,5-, bis--tert-butyl-hydroxy phenyl) propionic ester], eight decyls-3-(3,5-, bis--tert-butyl-hydroxy phenyl) propionic ester, 1,3,5-trimethyl-2,4,6-tri-(3,5-, bis--tertiary butyl-4-hydroxy benzyl) benzene, BHT, 2,6-, bis--tert-butyl group-4-ethyl-phenol, 2,2 '-methylene two (4-methyl-6-tert-butylphenol), 4,4 '-sulfo--bis--(3 methy 6 tert butyl phenol), 4,4 '-butylidene-bis-(3 methy 6 tert butyl phenol), 1,1,3-tri-(2-methyl-4-hydroxyl-5-tert-butyl-phenyl) butane, 1,3,5-tri-(4-hydroxybenzyl) benzene and four [methylene-3-(3,5 '-bis--tert-butyl group-4 '-hydroxy-phenylpropionic acid 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-, bis--tert-butyl-phenyl-3, the benzoic ether of 5-bis--tertiary butyl-4-hydroxy benzoic ether etc. is ultraviolet light absorber;

The triazine of 2-(4,6-diphenyl-1,3,5-triazines-2-yl)-5-hexyl hydroxyl phenol etc. is 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-propyl 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-n-butyl alcohol, 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-PD, 3-diethylamino-1,2-PD, 2-dimethylamino-1, the amino-alkane glycols of ammediol, 2-diethylamino-1,3-PD etc.;

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

1-amino cyclopentyl ketone methyl alcohol, 4-amino cyclopentyl ketone methyl alcohol etc. containing amino cyclanone methyl alcohol class;

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. containing amino loop chain alkane methyl alcohol class; The aminocarboxylic acids of Beta-alanine, 2-amino-butyric acid, 3-aminobutyric acid, 4-Aminobutanoicacid, the amino different acetic acid of 2-, the amino different acetic acid 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, m-toluidine, 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, N-diethylaniline, aromatic amine to methyl-DMA etc.;

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

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

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

By adding organic amine compound, can make to develop time, on the substrate of unexposed portion, do not produce residue, and can give and the pixel of the adhesion excellence of substrate.

As (H) hardening agent, for example can enumerate, by heating, with carboxyl reaction in (C) adhesive resin, with the crosslinked compound of (C) adhesive resin; Polymerization separately, make the curing compound of colored pattern 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 epoxy resin, hydrogenated bisphenol A is epoxy resin, Bisphenol F is epoxy resin, A Hydrogenated Bisphenol A F is 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 resin, glycidyl amine is resin, epoxidation wet goods epoxy resin, or the brominated derivative of these epoxy resin, aliphatics beyond epoxy resin and 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, while containing epoxy compound, oxetane compound etc., preferably contain the compound of the oxetanes skeleton ring-opening polymerization of epoxy radicals, the oxetane compound that can make epoxy 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, Isosorbide-5-Nitrae, 5,8-naphthalene tetracarboxylic acid, 3,3 ' 4, the aromatic polycarboxylic 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, the alicyclic polybasic carboxylic acid class of 4,5-cyclohexane tetrabasic carboxylic acid etc. etc.

As polybasic acid anhydride class, for example can enumerate phthalic anhydride, pyromellitic acid acid anhydride, trimellitic anhydride, 3,3 ', 4, the aromatic polycarboxylic acid 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, the alicyclic polybasic acid anhydride class of 4,5-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 containing 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 be used as the commercially available prod of 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 manufactures), リカシ Star De HH and MH-700 (be new Japanese physics and chemistry company manufacture) 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 the pattern of color filter, for example can enumerate, cured composition for color of the present invention (is for example coated on to substrate or other resin bed, other cured composition for color layers that first form on substrate etc.) on, except volatile ingredients such as desolventizings, form dyed layer, see through photomask, make this dyed layer exposure, develop, as required, heat again, it is so-called photolithograph method, or use ink discharge device, cured composition for color is coated on substrate or other resin bed, except volatile ingredients such as desolventizings, form dyed layer, by heat or expose at least one is cured, it is so-called ink-jet method.

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

Embodiment

By the following examples the present invention is further illustrated.

Synthesis example 1

The synthetic > 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 ℃ are heated 6 hours.Filter and take out precipitate, first 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 ℃, add ten chlordene Phthalocyanine Zinc 25.0g (22 mM) to stir, then dropping liquid bromine 60.0g (751 mM), heat to 130 ℃ with 20 hours, keep 1 hour.The reactant obtaining is taken out and is put in water, separate out the rough pigment of chlorination bromination phthalocyanine.Filter the thick graining paste of this chlorination bromination phthalocyanine, then with 60 ℃ of warm water cleanings, then clean by 1% niter cake aqueous solution, then use 60 ℃ of warm water cleanings, then, 60 ℃ of drying under reduced pressure, obtain the refining rough pigment of chlorination bromination phthalocyanine of 21.3g.

Then, the rough pigment 20g of chlorination bromination phthalocyanine that aforesaid operations is obtained and sodium chloride 60g and diethylene glycol 20g pack kneading machine into, 90 ℃ within 5 hours, grind 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 bromination ZnPc pigment of 12.8g.

To the chlorination bromination ZnPc pigment obtaining, process ion chromatography analysis with flask burning, result is, the substituent ratio on ZnPc skeleton is, bromine 14.6, chlorine 1.4, hydrogen 0.

Synthesis example 2

The synthetic > 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), at 40 ℃, mix, add ZnPc 25.0g (43.3 mM) to stir, then under agitation splash into bromine 60.0g (751 mM), heat to 130 ℃ with 20 hours, keep 1 hour.The reactant obtaining is taken out and is put in water, separate out the rough pigment of chlorination bromination phthalocyanine.Filter the thick graining paste of this chlorination bromination phthalocyanine, then with 60 ℃ of warm water cleanings, then clean by 1% niter cake aqueous solution, then use 60 ℃ of warm water cleanings, then, 60 ℃ of drying under reduced pressure, obtain the refining rough pigment of chlorination bromination phthalocyanine of 22.5g.

Then, the rough pigment 20g of chlorination bromination phthalocyanine that aforesaid operations is obtained and sodium chloride 60g and diethylene glycol 20g pack kneading machine into, 90 ℃ within 5 hours, grind 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 bromination ZnPc pigment of 14.3g.

To the chlorination bromination ZnPc pigment obtaining, process ion chromatography analysis with flask burning, result is, the substituent ratio on ZnPc skeleton is, bromine 13.4, chlorine 2.2, hydrogen 0.4.

Synthesis example 3

The synthetic > of < colorant (A-3)

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

300g water is joined to 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 under ice-cooled and carry out.Add sodium nitrite 12.6g (183 mM), stir 30 minutes.35% hydrochloric acid that slowly adds 38.1g, becomes after brown solution, stirs 2 hours.In reaction solution, add the aqueous solution being obtained at the water of 57.4g by the acid amides sulfuric acid dissolution of 5.3g, stir, obtain the suspension that contains diazo salt.

The N representing in formula (28), adds water 372g in N '-dimethyl barbituric acid 18.6g (146 mM), then under ice-cooled, with 30% sodium hydrate aqueous solution adjusting pH be 8～9.

Below operate under ice-cooled and carry out.Stir above-mentioned barbiturates aqueous alkali, become colorless after solution, on one side regulate pH to 8～9 with 30% sodium hydrate aqueous solution, the pump suspension that contains diazo salt that drips for one side.After dropping liquid finishes, then stir 3 hours, obtain yellow suspension.To filter the yellow solid that obtains under reduced pressure 60 ℃ dry, obtain the azo-compound 15g (21 mMs, yield 34%) that formula (29) represents.

Possessing in the flask that has cooling tube and stirring apparatus, azo-compound 5g (7 mM), the chloroform 50g and the N that add formula (29) to represent, dinethylformamide 2g (3 mM), stir and maintain 20 ℃ and following on one side, dropping liquid adds thionyl chloride 6g (54 mM) on one side.After dropping liquid finishes, be warming up to 50 ℃, synthermally maintain 5 hours, make its reaction, be then cooled to 20 ℃.Stir cooled reaction solution on one side, maintain 20 ℃ and following, dropping liquid adds the mixed liquor of 3-aminophenyl butane 3g (20 mM) and triethylamine 10g (103 mM) on one side.Then synthermal stirring 5 hours, makes its reaction.Then the solvent that heats up in a steamer dereaction potpourri with rotary evaporator, then adds a small amount of methyl alcohol, strong agitation.In the mixed liquor of acetic acid 29g and ion exchange water 300g, stir while add this potpourri, make crystallization.The crystallization that filtration is separated out, cleans with ion exchange water, and 60 ℃ of drying under reduced pressure, obtain the azo-compound 6g (6 mMs, yield 78%) that formula (7-4) represents.

The azo-compound obtaining for the present embodiment, with following condition, carries out LC-MS analysis.

Device: Agilent1100 (manufacture of Agilent Technology company)

Detecting device: UV detecting device: 254nm

Chromatographic column: Sumipax ODS (living fractional analysis セ Application タ mono-company manufactures)

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

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

The synthetic > of < colorant (A-4)

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

In 2 of formula (27) expression, in 2 '-biphenylamine disulfonic acid (moisture 30%) 100g (203 mM), add 3000g water, 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), stir 30 minutes.35% hydrochloric acid that slowly adds 150g, becomes after brown solution, stirs 2 hours.In reaction solution, add acid amides sulfuric acid dissolution by 38g (406 mM) in 380g water and the aqueous solution obtaining stirs, obtain the suspension that contains diazo salt.

In the 1-ethyl-3-cyano group-4-methyl-6-pyridone-2-ketone 76g (426 mM) representing in formula (30), add water 1000g, then under ice-cooled, with 30% sodium hydrate aqueous solution adjusting pH be 8～9.

Below operate under ice-cooled and carry out.Stir the aqueous alkali of above-mentioned pyridinone, become colorless after solution, regulate pH to 8～9 with 30% sodium hydrate aqueous solution on one side, the suspension that dropping liquid contains diazo salt on one side.After dropping liquid finishes, then stir 3 hours, obtain yellow suspension.To filter the yellow solid that obtains under reduced pressure 60 ℃ dry, obtain the azo-compound 137g (204 mMs, yield 100%) that formula (31) represents.

Possessing in the flask that has cooling tube and stirring apparatus, azo-compound 5g (7 mM), the chloroform 50g and the N that add formula (31) that aforesaid operations obtains to represent, dinethylformamide 2.4g (33 mM), stir and maintain 20 ℃ and following on one side, dropping liquid adds thionyl chloride 7g (59 mM) on one side.After dropping liquid finishes, be warming up to 50 ℃, synthermally maintain 5 hours, make its reaction, be then cooled to 20 ℃.Stir cooled reaction solution on one side, maintain 20 ℃ and following, dropping liquid adds the mixed liquor of 1,5-dimethylhexylamine 4g (30 mM) and triethylamine 12g (119 mM) on one side.Then 1 evening of synthermal stirring, make its reaction.Then the solvent that heats up in a steamer dereaction potpourri with rotary evaporator, then adds a small amount of methyl alcohol, strong agitation.In the mixed liquor of acetic acid 29g and ion exchange water 300g, stir while add this potpourri, make crystallization.The crystallization that filtration is separated out, cleans with ion exchange water, and 60 ℃ of drying under reduced pressure, obtain the azo-compound 6g (6 mMs, yield 80%) that formula (3-12) represents.

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

Synthesis example 5

The synthetic > of < resin (C-1)

There is stirring machine, thermometer, also flow in the flask of 1000ml of cooling tube, tap funnel and gas introduction tube possessing, pass into propylene glycol monomethyl ether 333g.Then, by gas introduction tube, in flask, pass into nitrogen, make to be substituted by flask nitrogen environment.Then, solution in flask is warming up to after 100 ℃, use tap funnel, in flask, splashed into the potpourri being formed by dicyclopentenyl methacrylate (FA-513M: Hitachi changes into industrial group and manufactures) 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 with 2 hours, after dropping liquid finishes, continue again 100 ℃ and stir for 5 hours.

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

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

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

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

Device: HLC-8120GPC (eastern ソ mono-company manufactures)

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

Correction standard substance: TSK standard styrene F-40, F-4, F-1, A-2500, A-500 (eastern ソ mono-company manufactures)

Synthesis example 6

The synthetic > of < resin (C-2)

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

After stirring finishes, to in flask, be substituted by air ambient from nitrogen, to adding glycidyl methacrylate 35.5g[0.25 mole (carboxyl of the methacrylic acid using with respect to this reaction is 50 % by mole) in flask], three dimethylaminomethyl phenol 0.9g and quinhydrones 0.145g, 110 ℃ of reactions, obtain the solution (solid constituent 28.9 quality %, acid number 79mgKOH/g) that contains 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 present embodiment use composition as follows, below sometimes simply represent.

(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) that formula (3-1) represents

(A-6) colorant (dyestuff): the compound (anthocyanin based dye: NK-3212: woods protobiochemistry research institute manufactures) that formula (21) represents

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

(A-8) colorant (dyestuff): the compound that formula (A-8) represents

(A-9) colorant (dyestuff): the compound that formula (A-9) represents

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

(B-1) polymerizable compound: DPHA (Japanese chemical drug company manufacture)

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

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

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

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

(E-1) polymerization causes auxiliary agent: 4,4 '-bis-(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 (large Japanese イ Application キ chemical industrial company manufacture)

Pigment dispersing agent 1: デイスパ mono-PVC Star Network 2001 (PVC Star Network ケミ mono-company manufactures) (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

Above-mentioned composition is packed into mayonnaise (the マヨネ mono-ズ) bottle of capacity 143ml, add again zirconium oxide bead 166.500 mass parts of diameter 0.5mm, airtight,, after 20 hours, filter and obtain pigment dispersion 1 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, by following formula, each composition is mixed, obtain cured composition for color 1.

Pigment dispersion 13.775 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 with spin-coating method, within 1,100 ℃, 3 minutes, make volatile ingredient volatilization at glass (EAGLE2000: コ mono-ニ Application グ company manufactures) upper coating cured composition for color obtained above, form cured composition for color film.After cooling, irradiate i line (wavelength 365nm) to this cured composition for color film, exposure.I line source uses extra-high-pressure mercury vapour lamp, irradiates as directional light.Irradiation light quantity is 200mJ/cm ².Then, carry out the rear baking (postbake) of 220 ℃, 20 minutes, 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.

[evaluating 1] brightness evaluation

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

[evaluating 2] contrast evaluation

With contrast colour examining machine (CT-1; Hu Ban motor company manufactures), take 10000 as blank value, measure the contrast value of the cured composition for color film obtaining, be 9180.

As the metewand of the contrast of cured composition for color film, the words of contrast value more than 8000, think and there is no depolarized property, demonstrate the characteristic that color filter is good, contrast value exceedes 5800, below 8000, can find some depolarized property, but no problem in the practicality of color filter, contrast value, below 5800, can confirm obvious depolarized property, is problematic as color filter.

[evaluating 3] Evaluation of Heat Tolerance

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

Then, by the cured composition for color film obtaining, in baking oven, the lower 230 ℃ of heating of air ambient 120 minutes, the same colourity of measuring the cured composition for color film after heating, tries to achieve the aberration (Δ Eab*) before and after heating, and is 4.6.

As the metewand of aberration, the words of Δ Eab* below 5, think and there is no that form and aspect change, demonstrate the characteristic that color filter is good, Δ Eab* exceedes 5, below 10, can find that some form and aspect change, but no problem in the practicality of color filter, Δ Eab*, more than 10, can confirm obvious form and aspect and change, and is problematic as color filter.

[evaluating 4] Investigation on Photodegradation

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

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

As the metewand of aberration, the same, Δ Eab*, below 5, thinks and there is no that form and aspect change, and demonstrate the characteristic that color filter is good, Δ Eab* exceedes 5, words below 10, can find that some form and aspect change, but no problem in the practicality of color filter, the words of Δ Eab* more than 10, can confirm obvious 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 in the same manner cured composition for color 2～6 with embodiment 1.

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

Evaluate in the same manner with embodiment 1 cured composition for color 2～6 obtaining, 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 mixing, with the abundant dispersed color of sand mill, obtain pigment dispersion 2.

[modulation of cured composition for color 7]

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

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]

Glass substrate (イ mono-グ Le 2000: コ mono-ニ Application グ company manufactures) 2 inches of the length of sides is upper, with spin-coating method coating cured composition for color 7, then, carries out 100 ℃, 3 minutes preliminary dryings.After cooling, the 100 μ m that are spaced apart of the substrate that order has been coated with cured composition for color and the figuratum quartz glass of tool photomask processed, use exposure machine (TME-150RSK; トプコ Application company manufactures), under atmospheric environment, with 150mJ/cm ²exposure (365nm benchmark) light irradiation.After irradiation, above-mentioned film is immersed in and contains the water system developer solution that nonionic is surfactant 0.12% and potassium hydroxide 0.04%, 23 ℃ of dippings develop for 80 seconds, after washing, carry out 220 ℃ of rear bakings of 20 minutes (post bake) in baking oven.After letting cool, with determining film thickness device (DEKTAK3; Vacuum technique company of Japan manufactures) measure the thickness of the cured pattern obtaining, be 2.2 μ m.

[evaluation]

To the film on the glass substrate obtaining, with colour examining machine (manufacture of OSP-SP-200:OLYMPUS company), (x, y) and brightness (Y), with contrast meter (color colour difference meter BM-5A to adopt illuminant-C to measure the xy chromaticity coordinate of the XYZ color specification system of CIE; トプコ Application company manufactures) mensuration contrast.Result is as shown in table 3.For Evaluation of Heat Tolerance and Investigation on Photodegradation, also obtain good result.

Embodiment 8

Except (A-8) become (A-9), obtain similarly to Example 7 cured composition for color 8.Similarly to Example 7, form the pattern of thickness 2.2 μ m, evaluate.Result is as shown in table 3.For Evaluation of Heat Tolerance and Investigation on Photodegradation, also obtain good result.

[table 3]

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

Embodiment 9

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

Industry utilizability

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

Claims

1. a cured composition for color, contain (A) colorant and (B) polymerizable compound, (A) colorant for contain formula (1) represent pigment and the colorant of weld, the content of weld is 2～100 quality % with respect to yellow holochrome

In formula (1), A ¹～A ¹⁶independent hydrogen atom, chlorine atom or the bromine atoms of representing separately,

Described weld contains at least a kind of dyestuff selecting from the group that barbiturates azo based dye and pyridone azo based dye form;

Barbiturates azo based dye is the dyestuff that formula (2) represents,

In formula (2), T ¹and T ²independent oxygen atom or the sulphur atom of representing separately,

R ³¹～R ³⁴the independent hydrogen atom that represents separately; With or the aliphatic alkyl of the carbon number 1～8 that replaces without the alkoxy of hydroxyl, carbon number 1～8 or the thioalkoxy group of carbon number 1～8; Contain or do not contain aliphatic hydroxyl, alkoxy, carboxyl, sulfo group or have the aryl of the carbon number 6～20 of the group of ester bond; The aralkyl of carbon number 7～20; The acyl group of the carbon number 2～10 of bonding or not bonding aliphatic alkyl or alkoxy,

R ³⁵and R ³⁹represent N position-replacement sulfamoyl,

R ³⁶～R ³⁸and R ⁴⁰～R ⁴²independent 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 of representing separately, the contained hydrogen atom of this aliphatic alkyl can replace with halogen atom;

The dipolymer that the salt of the compound that pyridone azo based dye represents for formula (3), the compound that formula (3) represents or the compound that formula (3) represents form,

In formula (3), Z represents: contain 1 or 2 and be selected from halogen atom, use or without the substituent phenyl of at least a kind in alkoxy, hydroxyl, carboxyl, carbamyl, sulfo group, sulfamoyl and N position-replacement sulfamoyl of the aliphatic alkyl of the alkoxy of carbon number 1～8 or the carbon number of carboxyl substituted 1～12, carbon number 1～8; Or contain 1～3 and be selected from halogen atom, use or without the substituent naphthyl of at least a kind in alkoxy, hydroxyl, carboxyl, carbamyl, sulfo group, sulfamoyl and N position-replacement sulfamoyl of the aliphatic alkyl of the alkoxy of carbon number 1～8 or the carbon number of carboxyl substituted 1～12, carbon number 1～8

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

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

R ²³represent hydrogen atom; The aliphatic alkyl of straight chain shape, a chain or the ring-type of carbon number 1～10; 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; Benzyl, phenyl propyl, 1-methyl-3-phenyl propyl, phenyl butyl, 3-amino-1-phenyl butyl; The heterocyclic radical of carbon number 3～20; Carbamyl; N position-substituted-amino formoxyl; The alkoxy carbonyl group of carbon number 2～20; Phenyloxycarbonyl, 4-methylphenoxy carbonyl, methane sulfonyl, butane sulfonyl, methoxyl methane sulfonyl, Ethyl Methyl Ether sulfonyl, Ethoxyethane sulfonyl; Benzenesulfonyl, tosyl.

2. cured composition for color as claimed in claim 1, wherein, weld, except the weld limiting in claim 1, further contains the dyestuff that is selected from pyrazolone azo based dye, Kui phthalein ketone based dye and anthocyanin based dye at least a kind.

3. the cured composition for color as described in any one in claim 1～2, wherein, also contains (C) adhesive resin.

4. a pattern cured dyed layer, described pattern cured dyed layer right to use requires the cured composition for color described in 1～3 any one, forms with photolithograph method or ink-jet method.

5. a color filter, contains pattern cured dyed layer claimed in claim 4.

6. a liquid crystal indicator, possesses color filter claimed in claim 5.