KR20090126192A - Colored curable composition - Google Patents

Abstract

PURPOSE: A colored curing composition, a pattern by using the composition, a color filter including the pattern, and the liquid crystal display equipped with the color filter are provided to improve the brightness and contrast of a color filter. CONSTITUTION: A colored curing composition comprises a colorant which comprises a pigment represented by the formula 1, and a yellow dye; and a polymerizable compound, wherein A1 ~ A16 are independently a hydrogen atom, a chlorine atom or a bromine atom. The colored curing composition comprises further a binder resin.

Description

Colored curable composition {COLORED CURABLE COMPOSITION}

This invention relates to the colored curable composition used for formation of color filters, such as a liquid crystal display panel.

Since the display device using the color filter performs image display by the light transmitted through the color filter, there is a problem that the brightness is lowered as compared with the self-luminous display such as a plasma display, which is bright and clear. In order to obtain an image, a high color filter is required.

[Preceding technical literature]

[Non-Patent Documents]

[Non-Patent Document 1]

P.114 (Ataru Izumiya et al .; Kanki Publishing, April 18, 2005 issuance)

An object of the present invention is to provide a colored curable composition capable of forming a color filter having excellent brightness and contrast.

MEANS TO SOLVE THE PROBLEM The present inventors came to complete this invention, as a result of repeating | researching to discover the colored curable composition which can solve the above subject.

That is, this invention provides the following invention.

1. Colored curable composition containing (A) coloring agent and (B) polymeric compound, and (A) coloring agent is a coloring agent containing the pigment and yellow dye represented by Formula (1).

[In Formula (1), A <^1> -A <^16> respectively independently represents a hydrogen atom, a chlorine atom, or a brom atom.]

2. Yellow dye wherein at least one dye selected from the group consisting of barbituric acid azo dyes, pyridone azo dyes, pyrazolone azo dyes, quinophthalone dyes and cyanine dyes The colored curable composition of Claim 1 which is phosphorus.

3. The colored curable composition according to the above 2, wherein the barbituric acid azo dye is a dye represented by formula (2).

[In formula (2), T <^1> and T <^2> represent an oxygen atom or a sulfur atom each independently.

R ³¹ to R ³⁴ each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, and 7 to 20 carbon atoms that may have a substituent. The C2-C10 acyl group which may have an aralkyl group or a substituent is shown.

R ³⁵ to R ⁴² each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, a carboxyl group, a sulfo group, a sulfamoyl group, or an N-substituted sulfamoyl group. The hydrogen atom contained in the aliphatic hydrocarbon group may be substituted with a halogen atom.]

4. The colored curable composition according to item 2, wherein the pyridone azo dye is a dimer formed of a compound represented by formula (3), a salt of a compound represented by formula (3), or a compound represented by formula (3).

[In Formula (3), Z is a C1-C12 aliphatic hydrocarbon group, a C1-C8 alkoxyl group, a hydroxyl group, a carboxyl group, a carbamoyl group, a sulfo group, and a sulfamoyl which may have a halogen atom and a substituent. A phenyl group having one or two substituents or at least one substituent selected from the group consisting of a diary and an N-substituted sulfamoyl group, or a halogen atom or a C1-C12 aliphatic hydrocarbon group which may have a substituent, C1-C1 8 represents a naphthyl group having 1 to 3 substituents selected from the group consisting of an alkoxyl group, hydroxyl group, carboxyl group, carbamoyl group, sulfo group, sulfamoyl group and N-substituted sulfamoyl group .

R ²¹ represents a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms, a carboxyl group or a trifluoromethyl group.

R ²² represents a hydrogen atom, a cyano group, a carbamoyl group, an N-substituted carbamoyl group, a sulfamoyl group, or a sulfo group.

R ²³ is a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, or carbon number 7 which may have a substituent An aralkyl group having 20 to 20 carbon atoms, a heterocyclic group having 3 to 20 carbon atoms, a carbamoyl group, an N-substituted carbamoyl group, or an alkyloxycarbonyl group having 2 to 20 carbon atoms which may have a substituent or a substituent may be used. An aryloxycarbonyl group having 7 to 30 carbon atoms, an acyl group having 2 to 20 carbon atoms which may have a substituent, an aliphatic sulfonyl group having 1 to 30 carbon atoms which may have a substituent or an arylsulfonyl group having 6 to 30 carbon atoms which may have a substituent Is displayed.]

5. Furthermore, the colored curable composition in any one of said 1-4 containing (C) binder resin.

6. The pattern formed by the photolithographic method or the inkjet method using the colored curable composition in any one of said 1-5.

7. A color filter comprising the pattern of 6 above.

8. A liquid crystal display device comprising the color filter according to the above 7.

The colored curable composition of this invention contains the pigment represented by Formula (1) as a (A) coloring agent.

[In Formula (1), A <^1> -A <^16> respectively independently represents a hydrogen atom, a chlorine atom, or a brom atom.]

In formula (1), the number of substituents represented by A ^{1 to} A ¹⁶ is preferably 0 to 6 chlorine atoms, 10 to 16 bromine atoms, and 10 to 16 chlorine atoms and bromine atoms, More preferably, there are 0 to 3 chlorine atoms, 13 to 16 bromine atoms, and 13 to 16 chlorine atoms and bromine atoms, more preferably 1 to 3 chlorine atoms, 13 to 13 bromine atoms. 15, and the sum of chlorine and bromine atoms is 14-16.

When the number of substituents is in the above-described range, the color becomes more yellowish, which is preferable because the brightness becomes high without lowering the color reproduction range when the color filter is used.

As a manufacturing method of the pigment represented by Formula (1), it can manufacture by the method described in Unexamined-Japanese-Patent No. 2007-284589, Unexamined-Japanese-Patent No. 2007-291232, Unexamined-Japanese-Patent No. 2008-19383, and the like. .

Content of the pigment represented by Formula (1) is 0.5-99.9 mass% with respect to (A) coloring agent whole quantity, Preferably it is 1-99 mass%, More preferably, it is 2-98 mass%.

The colored curable composition of this invention contains a yellow dye further as (A) coloring agent. The yellow dye is preferably at least one dye selected from the group consisting of barbituric acid azo dyes, pyridone azo dyes, pyrazolone azo dyes, quinophthalone dyes and cyanine dyes.

It does not specifically limit as a barbituric acid azo dye, Although a well-known substance can be used, Preferably, the barbituric acid azo dye represented by Formula (2) is used.

[In formula (2), T <^1> and T <^2> represent an oxygen atom or a sulfur atom each independently.

R ³¹ to R ³⁴ each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, and 7 to 20 carbon atoms that may have a substituent. The C2-C10 acyl group which may have an aralkyl group or a substituent is shown.

R ³⁵ to R ⁴² each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, a carboxyl group, a sulfo group, a sulfamoyl group, or an N-substituted sulfamoyl group. The hydrogen atom contained in the aliphatic hydrocarbon group may be substituted with a halogen atom.]

T ¹ and T ² each independently represent an oxygen atom or a sulfur atom, and may be the same or different, but are preferably the same.

The aliphatic hydrocarbon group having 1 to 10 carbon atoms in R ³¹ to R ³⁴ may be linear, branched or cyclic. Carbon number of a C1-C10 aliphatic hydrocarbon group becomes like this. Preferably it is 2-8, More preferably, it is 3-6. Examples of the aliphatic hydrocarbon group having 1 to 10 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group and ethylhexyl group ( 2-ethylhexyl group etc.), a cyclopentyl group, a cyclohexyl group, a cyclohexyl alkyl group, etc. are mentioned.

In addition, the hydrogen atom contained in a C1-C10 aliphatic hydrocarbon group may be a hydroxyl group, a C1-C8 (preferably C1-C4) alkoxyl group, or C1-C8 (preferably C1-C4). May be substituted with a thioalkoxyl group. Examples of the substituted aliphatic hydrocarbon group include a hydroxyethyl group (such as 2-hydroxyethyl group), an ethoxyethyl group (such as 2-ethoxyethyl group), and an ethylhexyloxypropyl group (3- (2-ethylhexyloxy). ) Propyl group etc.), methylthiopropyl group (3-methylthiopropyl group etc.), etc. are mentioned.

The C6-C20 aryl group in R <^31> -R <^34> may be unsubstituted, and may have substituents, such as an aliphatic hydrocarbon group, an alkoxyl group, a carboxyl group, a sulfo group, or group containing an ester bond. Carbon number of the said aryl group is counted including carbon number of a substituent, Preferably it is 6-10. As an aryl group, a phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-sulfophenyl group, 3-sulfo, for example a phenyl group, such as 4-sulfonyl group and ethoxycarbonyl group _{(4- (C0OC 2 H 5)} Ph , and so on).

The alkyl moiety of the aralkyl group having 7 to 20 carbon atoms in R ³¹ to R ³⁴ may be linear, branched or cyclic. Carbon number of an aralkyl group counts including carbon number of a substituent, Preferably it is 7-10. Examples of the aralkyl having 7 to 20 carbon atoms include benzyl group and phenethyl group.

Unsubstituted may be sufficient as the C2-C10 acyl group in R <^31> -R <^34> , and substituents, such as an aliphatic hydrocarbon group or an alkoxyl group, may couple | bond. Carbon number of an acyl group counts including carbon number of a substituent, The number becomes like this. Preferably it is 2-10. As an acyl group, an acetyl group, a benzoyl group, a methoxy benzoyl group (p-methoxy benzoyl group etc.) etc. are mentioned, for example.

R ³⁵ an aliphatic hydrocarbon group of 1 to 10 carbon atoms in ~R ^42, those similar to the case of R ³¹ ~R ^34. The hydrogen atom contained in the aliphatic hydrocarbon group of R ³⁵ to R ⁴² may be substituted with a halogen atom, and preferably a fluorine atom as the halogen atom. A trifluoromethyl group etc. are mentioned as an example of the aliphatic hydrocarbon group substituted by the halogen atom.

Preferably carbon number of the C1-C8 alkoxyl group in R <^35> -R <^42> is 1-4. As an alkoxyl group, a methoxy group, an ethoxy group, isopropoxy group, n-propoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, etc. are mentioned, for example.

The N-position substituted sulfamoyl group in R ³⁵ to R ⁴² is preferably, for example, an N-position substituted monosulfamoyl group, and is represented by -SO ₂ NHR ¹³ .

R ¹³ may be a C 1-10 aliphatic hydrocarbon group which may have a substituent, a C 6-20 aryl group which may have a substituent, a C 7-20 aralkyl group which may have a substituent, or a carbon number which may have a substituent The acyl group of 2-10 is shown.

The aliphatic hydrocarbon group having 1 to 10 carbon atoms in R ¹³ may be linear, branched, or cyclic. The carbon number of the aliphatic hydrocarbon group does not include the carbon number of the substituent, and the number thereof is preferably 6 to 10.

As a C1-C10 aliphatic hydrocarbon group in R <^13> , For example, a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert- butyl group, Methylbutyl group (1,1,3,3-tetramethylbutyl group, etc.), methylhexyl group (1-methylhexyl group, 1,5-dimethylhexyl group, etc.), ethylhexyl group (2-ethylhexyl group, etc.) , A cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group (such as 2-methylcyclohexyl group), a cyclohexylalkyl group, and the like.

The aliphatic hydrocarbon group having 1 to 10 carbon atoms in R ¹³ may be substituted with an alkoxyl group having 1 to 8 carbon atoms (preferably having 1 to 4 carbon atoms), for example, a propoxypropyl group (3- (isopropoxy). ) Propyl group etc.) etc. are mentioned.

Unsubstituted may be sufficient as the C6-C20 aryl group in R <^13> , and may have substituents, such as an aliphatic hydrocarbon group or a hydroxyl group. Carbon number of the said aryl group is counted including carbon number of a substituent, Preferably it is 6-10. As an aryl group, a phenyl group, a hydroxyphenyl group (4-hydroxyphenyl group etc.), a trifluoromethylphenyl group (4-trifluoromethylphenyl group etc.), etc. are mentioned, for example.

The alkyl portion of the aralkyl group having 7 to 20 carbon atoms in R ¹³ may be either linear or branched. Carbon number of an aralkyl group is 7-20 normally, Preferably it is 7-10. Examples of the aralkyl group include phenylalkyl groups such as benzyl group, phenylpropyl group (1-methyl-3-phenylpropyl group, etc.), and phenylbutyl group (3-amino-1-phenylbutyl group, etc.).

Unsubstituted may be sufficient as the C2-C10 acyl group in R <^13> , and the hydrogen atom contained in an acyl group may be substituted by the aliphatic hydrocarbon group or the alkoxyl group. Carbon number of an acyl group counts including carbon number of a substituent, The number becomes like this. Preferably it is 6-10. As an acyl group, an acetyl group, a benzoyl group, o-toluyl group, m-toluyl group, p-toluyl group, a methoxy benzoyl group (such as p-methoxybenzoyl group), etc. are mentioned, for example.

Examples of the N-substituted sulfamoyl group include groups represented by the formulas (4) to (10).

  Examples of the barbituric acid azo dye include compounds represented by formulas (2-1) to (2-8), and preferably formulas (2-1) and (2-3) to (2-5) ), (2-7) and the compound represented by (2-8), etc. are mentioned.

Although it does not specifically limit as a pyridone azo dye, A well-known substance can be used, Preferably, what is represented by Formula (3) is used.

[In Formula (3), Z is a C1-C12 aliphatic hydrocarbon group, a C1-C8 alkoxyl group, a hydroxyl group, a carboxyl group, a carbamoyl group, a sulfo group, and a sulfamoyl which may have a halogen atom and a substituent. A phenyl group having one or two substituents or at least one substituent selected from the group consisting of a diary and an N-substituted sulfamoyl group, or a halogen atom or a C1-C12 aliphatic hydrocarbon group which may have a substituent, C1-C1 8 represents a naphthyl group having 1 to 3 substituents selected from the group consisting of an alkoxyl group, hydroxyl group, carboxyl group, carbamoyl group, sulfo group, sulfamoyl group and N-substituted sulfamoyl group .

R ²¹ represents a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms, a carboxyl group or a trifluoromethyl group.

R ²² represents a hydrogen atom, a cyano group, a carbamoyl group, an N-substituted carbamoyl group, a sulfamoyl group, or a sulfo group.

R ²³ is a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, or carbon number 7 which may have a substituent An aralkyl group having 20 to 20 carbon atoms, a heterocyclic group having 3 to 20 carbon atoms, a carbamoyl group, an N-substituted carbamoyl group, or an alkyloxycarbonyl group having 2 to 20 carbon atoms which may have a substituent or a substituent may be used. An aryloxycarbonyl group having 7 to 30 carbon atoms, an acyl group having 2 to 20 carbon atoms which may have a substituent, an aliphatic sulfonyl group having 1 to 30 carbon atoms which may have a substituent or an arylsulfonyl group having 6 to 30 carbon atoms which may have a substituent Is displayed.]

In Formula (3), the C1-C12 aliphatic hydrocarbon group in Z may be linear, branched, or cyclic. The carbon number of an aliphatic hydrocarbon group contains all the carbon number of a substituent, The number is 1-12 normally, Preferably it is 2-11. As an aliphatic hydrocarbon group, n-octyl group, methylhexyl group (1, 5- dimethylhexyl group, etc.), ethylhexyl group (2-ethylhexyl group, etc.), cyclooctyl group, methylcyclohexyl group (2 , A 2-dimethylcyclohexyl group, etc.), a cyclohexyl alkyl group, etc. are mentioned. The hydrogen atom contained in an aliphatic hydrocarbon group may be substituted by the C1-C8 alkoxyl group or carboxyl group. As an aliphatic hydrocarbon group which has a substituent, an alkoxy propyl group (3- (2'-ethylhexyloxy) propyl group etc.), 8- (carboxy) octyl group, etc. are mentioned.

Examples of the alkoxyl group having 1 to 8 carbon atoms in Z include methoxy group, ethoxy group, isopropoxy group, n-propoxy group, n-butoxy group, isobutoxy group, sec-butoxy group and tert-butoxy Season, etc. can be mentioned.

As a halogen atom in Z, a fluorine atom, a bromine atom, a chlorine atom, and an iodine atom are mentioned.

The N-substituted sulfamoyl group in Z is represented by -SO ₂ N (R ²⁴ ) R ²⁵ . R ²⁴ and R ²⁵ each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 16 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, and having 7 to 20 carbon atoms which may have a substituent. may have a substituent; an aralkyl group or a group of 2 to 15 carbon atoms, acyl good (where, R ²⁴ and R ²⁵ are, at the same time not being a hydrogen atom).

The aliphatic hydrocarbon group having 1 to 16 carbon atoms may be linear, branched or cyclic, and the aliphatic hydrocarbon group preferably has 6 to 16 carbon atoms.

As a C1-C16 aliphatic hydrocarbon group in R <^24> and R <^25> , any of linear, branched, or cyclic | annular form may be sufficient. Carbon number of an aliphatic hydrocarbon group does not contain the carbon number of a substituent, The number is 1-16 normally, Preferably it is 6-10. Examples of the aliphatic hydrocarbon group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group and methylbutyl group (1,1,3, 3-tetramethylbutyl group, etc.), methylhexyl group (1,5-dimethylhexyl group, etc.), ethylhexyl group (2-ethylhexyl group, etc.), cyclopentyl group, cyclohexyl group, methylcyclohexyl group (2- Methyl cyclohexyl group etc.), a cyclohexyl alkyl group, etc. are mentioned. The hydrogen atom contained in an aliphatic hydrocarbon group may be substituted by the C1-C8 alkoxyl group or carboxyl group. As an aliphatic hydrocarbon group which has a substituent, a propoxypropyl group (3- (isopropoxy) propyl group etc.), 2- (carboxy) ethyl group, 3- (carboxy) ethyl group, 4-carboxyethyl group, etc. are mentioned.

The C6-C20 aryl group in R <^24> and R <^25> may have substituents, such as an aliphatic hydrocarbon group or a hydroxyl group. Carbon number of an aryl group is counted including carbon number of a substituent, and is 6-20 normally, Preferably it is 6-10. As an aryl group, a phenyl group, a carboxyphenyl group (2-carboxyphenyl group, 2, 4- carboxyphenyl group etc.), a hydroxyphenyl group (4-hydroxyphenyl group etc.), trifluoromethylphenyl group (4-trifluoromethylphenyl group etc.) And methoxyphenyl group (4-methoxyphenyl group).

The alkyl portion of the aralkyl group having 7 to 20 carbon atoms in R ²⁴ and R ²⁵ may be either linear or branched. Carbon number of an aralkyl group is 7-20 normally, Preferably it is 7-10. As the aralkyl, benzyl group, phenylethyl group (2-phenylethyl group, 2- (4-hydroxyphenyl) ethyl group, etc.), phenylethylene group (such as 2-phenylethylene group), phenylpropyl group (1-methyl-3- Phenylalkyl groups such as phenylpropyl group) and phenylbutyl group (such as 3-amino-1-phenylbutyl group).

Unsubstituted may be sufficient as the C2-C15 acyl group in R <^24> and R <^25> , and may have substituents, such as an aliphatic hydrocarbon group, an alkoxyl group, or a carboxyl group. Carbon number of an acyl group counts including carbon number of a substituent, The number is 2-15 normally, Preferably it is 6-10. As an acyl group, for example, an acetyl group, a benzoyl group, a methoxy benzoyl group (such as p-methoxy benzoyl group), a carboxy acetyl group, 2-carboxy propionyl group, 3-carboxy propionyl group, 2-carboxybutyryl group , 3-carboxybutyryl group, 4-carboxybutyryl group, and the like.

R ²¹ represents a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms, a carboxyl group or a trifluoromethyl group.

The carbon number of a substituent is not contained in carbon number of the C1-C10 aliphatic hydrocarbon group in R <^21> . Preferably carbon number is 2-8, More preferably, it is 3-6. Examples of the aliphatic hydrocarbon group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclopentyl group and cyclohexyl group.

R ²² represents a hydrogen atom, a cyano group, a carbamoyl group or an N-substituted carbamoyl group, a sulfamoyl group, or a sulfo group.

Examples of the N-substituted carbamoyl group in R ²² include -CON (R ²⁶ ) R ²⁷ . R ²⁶ and R ²⁷ each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, and a 7 to 20 carbon atoms which may have a substituent. The C2-C10 acyl group which may have an aralkyl group or a substituent is shown.

The description and specific examples of the aliphatic hydrocarbon group, aryl group, aralkyl group and acyl group of R ²⁶ and R ²⁷ are the same as those described above for R ²⁴ and R ²⁵ . However, the acyl group may have a halogen atom. As an acyl group which has a halogen atom, a bromobenzoyl group (p-bromobenzoyl group etc.) etc. are mentioned, for example.

R ²³ is a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, or carbon number 7 which may have a substituent An aralkyl group having 20 to 20 carbon atoms, a heterocyclic group having 3 to 20 carbon atoms, a carbamoyl group, an N-substituted carbamoyl group, or an alkyloxycarbonyl group having 2 to 20 carbon atoms which may have a substituent or a substituent may be used. An aryloxycarbonyl group having 7 to 30 carbon atoms, an acyl group having 2 to 20 carbon atoms which may have a substituent, an aliphatic sulfonyl group having 1 to 30 carbon atoms which may have a substituent or an arylsulfonyl group having 6 to 30 carbon atoms which may have a substituent Indicates.

Examples of the aliphatic hydrocarbon group for R ²³ include the same groups as the aliphatic hydrocarbon group for R ²¹ described above.

As an aryl group in R <^23> , carbon number is 6-30 normally, Preferably it is 6-20, More preferably, it is 6-16. Specific examples of the aryl group include a phenyl group, 4-nitrophenyl group, 2-nitrophenyl group, 2-chlorophenyl group, 2, 4-dichlorophenyl group, 2,4-dimethylphenyl group, 2-methylphenyl group, 4-methoxyphenyl group, 2- A methoxyphenyl group, 2-methoxycarbonyl-4-nitrophenyl group, etc. are mentioned.

As an aralkyl group in R <^23> , either linear or branched form may be sufficient, and carbon number becomes like this. Preferably it is 7-10. Specific examples of the aralkyl include phenylalkyl groups such as benzyl group, phenylpropyl group (1-methyl-3-phenylpropyl group, etc.), and phenylbutyl group (3-amino-1-phenylbutyl group, etc.).

As a C3-C20 heterocyclic group in R <^23> , saturated or unsaturated may be sufficient, As carbon number, 3-20 are preferable, More preferably, it is 5-15. Specific examples of the heterocyclic group include pyrazole group, 1,2,4-triazole group, isothiazole group, benzoisothiazole group, thiazole group, benzothiazole group, oxazole group and 1,2,4-thiadiazole group. have. Moreover, you may have a substituent further.

The N-substituted carbamoyl group for R ²³ is the same as the N-substituted carbamoyl group described above for R ²² .

As an alkyloxycarbonyl group in R <^23> , it may be unsubstituted, may have a substituent, and may be cyclic. As carbon number of an alkyloxycarbonyl group, it is 2-20 normally, Preferably it is 2-16, More preferably, it is 2-10. As an alkyloxycarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, butoxycarbonyl group, etc. are mentioned.

As an aryloxycarbonyl group in R <^23> , it may be unsubstituted or may have a substituent, As carbon number, it is 7-30 normally, Preferably it is 7-20, More preferably, it is 7-16. Examples of the aryloxycarbonyl group include phenoxycarbonyl group, 4-methylphenoxycarbonyl group, and the like.

As an acyl group in R <^23> , it may be an aliphatic carbonyl group or an arylcarbonyl group, may be saturated or unsaturated, may be cyclic, and may have a substituent. As carbon number, it is 2-20 normally, Preferably it is 2-15, More preferably, it is 2-10. Examples of the acyl group include an acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, pivaloyl group and benzoyl group.

The aliphatic sulfonyl group in R ²³ may be saturated or unsaturated, or may be cyclic. As carbon number, it is 1-30 normally, Preferably it is 1-20, More preferably, it is 1-16. Examples of the aliphatic sulfonyl group include methanesulfonyl group, butanesulfonyl group, methoxymethanesulfonyl group, methoxyethanesulfonyl group, ethoxyethanesulfonyl group and the like.

As an arylsulfonyl group in R <^23> , you may have a substituent, As carbon number, it is 6-30 normally, Preferably it is 6-20, More preferably, it is 6-18. Examples of the arylsulfonyl group include benzenesulfonyl, toluenesulfonyl group, and the like.

As a pyridone azo dye, the following compound is mentioned, Preferably, the compound represented by Formula (3-1)-(3-9) is mentioned.

The compound represented by Formula (3) may form either of ammonium salt, lithium salt, sodium salt, or potassium salt.

The compound represented by Formula (3) may form the dimer or more multimer.

The multimer in Formula (3) is a compound which has a group derived from the compound represented by two or more Formula (3) in 1 molecule, and is specifically, represented by Formula (3-12)-formula (3-15) Compounds and the like.

It does not specifically limit as a pyrazolone azo dye, A well-known substance can be used, For example, the pyrazolone azo system as described in Unexamined-Japanese-Patent Nos. 2006-276512, 2005-263926, and 2006-015669. Dyes can be used.

Specifically, C.I. Acid yellow 17, C.I. Solvent orange 56 and C.I. The solvent yellow 82, the compound represented by Formula (11)-(14), etc. are mentioned.

It does not specifically limit as a quinophthalone type dye, A well-known substance can be used, For example, the quino of Unexamined-Japanese-Patent No. 5-39269, Unexamined-Japanese-Patent No. 6-220339, and Unexamined-Japanese-Patent No. 8-171201 can be used. Nophthalone dye.

Specifically, C.I. Solvent Yellow 33, C.I. Disperse yellow 54, C.I. Disperse yellow 64, the compound represented by Formula (15)-(19), etc. are mentioned.

It does not specifically limit as cyanine dye, A well-known substance can be used.

For example, the cyanine pigment | dye of Unexamined-Japanese-Patent No. 2005-194509, Unexamined-Japanese-Patent No. 2007-131818, and 2005-297406 can be mentioned.

Specifically, the compound etc. which are represented by Formula (20)-(23) are mentioned.

Moreover, as (A) coloring agent, you may contain other dye and a pigment in the range which does not impair the effect of this invention.

Examples of the dye include compounds classified as dyes in the color index (Published by The Society of Dyers and Colourists) and known dyes described in dyeing notes (dye company). Specifically, C.I. Solvent Yellow 4 (Hereinafter, description of CI solvent yellow is omitted, and description is made only for numbers. Other dye species and colors are omitted and described in the same manner.), 14, 15, 23, 24, 38, 62 , 63, 68, 82, 94, 98, 99, 162, CI Solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, C.I. Solvent orange 2, 7, 11, 15, 26, 45, 56 and the like. See also C.I. As acid dyes, C.I. Acid green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106, 109, C.I. Acid orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173, CI Acid yellow 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, l14, 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 a derivative thereof. See also C.I. direct dyes as C.I. Direct yellow 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, CI Direct orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107, C.I. And dyes such as direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and the like. In addition, C.I. As a modern dye, C.I. Modern yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65, C.I. Modern orange (mordant orange) 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47 , 48, CI Dye, such as modern green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, 53, Preferably, CI Solvent yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 162, acid green 1, 3, 5, 9, 16, 25 , 27, 50, 58, 63, 65, 80, 104, 105, 106, 109, CI Acid yellow 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 thereof Can be mentioned.

As said pigment, the compound classified as a pigment in the color index (The Society of Dyers and Colorsts published) is mentioned, Specifically, C.I. Pigment yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, Yellow pigments such as 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214, CI Pigments green, such as pigment green 7, 36, etc., Preferably, C.I. Pigment Yellow 138, 139, 150, C.I. Pigment green 7, 36 is mentioned.

The said pigment can be obtained as a dispersion liquid of the state in which the pigment was disperse | distributed uniformly in solution by containing a pigment dispersing agent and performing a dispersion process as needed.

Examples of the pigment dispersant include surfactants such as cationic, anionic, nonionic, amphoteric, polyester and polyamine, and may be used alone or in combination of two or more thereof.

Examples of the surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid modified polyesters, tertiary amine modified polyurethanes, and polyethyleneimines. In addition, KP (made by Shin-Etsu Chemical Co., Ltd.), polyflow (made by Toei Chemical Co., Ltd.), F-Top (made by Tochem Prodax Co., Ltd.), and Mega Pack (made by Dainippon Ink and Chemicals Co., Ltd.) are brand names. , Fluoride (manufactured by Sumitomo 3M Co., Ltd.), Asahi guide, saffron (above, made by Asahi Glass Co., Ltd.), Solsperth (manufactured by Geneca Co., Ltd.), EFKA (manufactured by EFKA CHEMICALS), and PB821 (Ajinomoto Co., Ltd.) Ltd.) and dispervic (made by BIC Chem Corporation), etc. are mentioned.

When using a dispersing agent, the usage-amount is a mass fraction with respect to 100 mass% of pigments, Preferably it is 0.1-100 mass%, More preferably, it is 5-50 mass%.

As average particle diameter of the pigment in a pigment dispersion liquid, it is 10-150 nm, Preferably it is 15-120 nm, More preferably, it is 20-100 nm.

Content of (A) coloring agent is 10-95 mass% in mass fraction with respect to solid content of a colored curable composition, Preferably it is 15-90 mass%, More preferably, it is 20-88 mass%.

In this specification, solid content means the total amount of the component except the solvent contained in a colored curable composition.

Content of the yellow dye used for the colored curable composition of this invention is 0.5-100 mass% in mass fraction with respect to all the yellow pigment | dyes, Preferably it is 1-100 mass%, More preferably, it is 2 It is -100 mass%.

Moreover, content of the yellow dye used for the colored curable composition of this invention is 0.5-99.9 mass% in mass fraction with respect to all the pigment | dyes of (A) coloring agent whole quantity yellow, Preferably it is 1-99 mass%, More preferably Preferably it is 2-98 mass%.

When content of a yellow dye exists in the said range, since the brightness and contrast at the time of using a color filter tend to become high, it is preferable.

As the polymerizable compound (B), a monomer or oligomer that is cured by heat or light or both thereof can be used, and these may be used in combination. As a monomer or oligomer, a well-known substance can be used.

Specific examples of the monomers include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexamethacrylate, and dipentaerythritol pentaacrylate derivatives having a carboxyl group, and ethylene oxide glycerin tree Acrylate, ethylene oxide trimethylol propane triacrylate, a propylene oxide glycerol triacrylate, etc. are mentioned.

Examples of the oligomers include epoxy acrylates, urethane acrylates, polyester acrylates, and the like, and for example, oligomers described in the present conditions and prospects of the UV / EB curing technology (published by CMC) on pages 18 to 20 can be used. have.

The content of the polymerizable compound (B) is preferably from 5 to 90% by mass, more preferably from 10 to 85% by mass, particularly preferably from 12 to 80% by mass, based on the mass fraction of the solid content of the colored curable composition. to be.

The colored curable composition of this invention may further contain (C) binder resin. (C) Binder resin, Preferably, it contains the repeating unit derived from (meth) acrylic acid. Here, (meth) acrylic acid represents acrylic acid and / or methacrylic acid. The content of the repeating unit derived from (meth) acrylic acid is in a mole fraction of all the repeating units constituting the binder resin, preferably 10 mol% or more and 40 mol% or less, more preferably 13 mol% 35 mol% or more.

As another monomer which induces repeating units of binder resins other than the repeating unit derived from (meth) acrylic acid, For example, aromatic vinyl compound, unsaturated carboxylic acid ester, unsaturated carboxylic acid aminoalkyl ester, unsaturated carboxylic acid glycy Dyl esters, carboxylic acid vinyl esters, unsaturated ethers, vinyl cyanide compounds, unsaturated amides, unsaturated imides, aliphatic conjugated dienes, macro having monoacryloyl groups and monomethacryloyl groups at the ends of the polymer molecular chain Monomers are mentioned, for example, the repeating unit represented by Formula (24), the repeating unit represented by Formula (25), etc. are mentioned.

[In Formulas (24) and (25), R ⁵¹ and R ⁵² each independently represent a hydrogen atom or a saturated aliphatic hydrocarbon group having 1 to 6 carbon atoms.]

As R ⁵¹ and R ⁵² , a hydrogen atom, a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, 1-methylbutyl group, 2 -Methylbutyl group, 3-methylbutyl group, 1-ethylpropyl group, 2-ethylpropyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylphene group And a methyl group, 1-ethylbutyl group, 2-ethylbutyl group, 3-ethylbutyl group, and the like, preferably hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec -Butyl group or tert-butyl group are mentioned, More preferably, a hydrogen atom, a methyl group, or an ethyl group is mentioned.

Specifically as (C) binder resin, methacrylic acid / benzyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene copolymer, methacrylic acid / benzyl methacrylate / isobornyl methacrylate in the air Copolymer, methacrylic acid / styrene / benzyl methacrylate / N-phenylmaleimide copolymer, methacrylic acid / repeating unit represented by formula (25) (wherein, in formula (25), R ³¹ represents a methyl group, R ³² represents a hydrogen atom./N-benzylmaleimide/benzyl methacrylate copolymer, methacrylic acid / repeating unit represented by formula (25) (wherein in formula (25), R ⁵¹ is a methyl group) And R ⁵² represents a hydrogen atom.) / N-cyclohexylmaleimide / benzyl methacrylate copolymer, methacrylic acid / repeating unit represented by formula (24) (wherein R in formula (24) ⁵¹ represents a methyl group, and R ⁵² represents a hydrogen atom.) / Benzyl Methacrylate copolymer, the repeating unit represented by Formula (24) (However, in Formula (24), R ⁵¹ represents a methyl group and R ⁵² represents a hydrogen atom.) / Benzyl methacrylate copolymer, meta The repeating unit represented by methacrylic acid / formula (25) (However, in formula (25), R ⁵¹ represents a methyl group, R ⁵² represents a hydrogen atom.) / Styrene / dicyclopentanyl methacrylate copolymer, etc. desirable.

The acid value of (C) binder resin becomes like this. Preferably it is 30-150, More preferably, it is 35-135, Especially preferably, it is 40-120.

The acid value is a value measured as the amount of potassium hydroxide required to neutralize 1 g of the acrylic polymer (mg), and can be determined by titration using an aqueous potassium hydroxide solution.

(C) Content of binder resin is mass fraction with respect to solid content of colored curable composition, Preferably it is 5-40 mass%, More preferably, it is 8-35 mass%, Especially preferably, it is 10-32 mass% to be.

(C) binder resin which has a repeating unit represented by Formula (24), for example, the repeating unit represented by the repeating unit / formula (24) derived from methacrylic acid (However, in Formula (24), R ⁵¹ is A methyl group, R ⁵² represents a hydrogen atom.) / A copolymer comprising a repeating unit derived from benzyl methacrylate is a two-component obtained by polymerizing methacrylic acid and benzyl methacrylate to obtain a two-component polymer. polymer and the formula (26) represents a compound can be obtained by reacting (in the stage, in this case, equation (26), R ⁵³ represents a hydrogen atom.).

Repeating unit derived from methacrylic acid / Repeating unit represented by Formula (25) (However, in Formula (25), R ⁵¹ represents a methyl group and R ⁵² represents a hydrogen atom.) / Benzyl methacrylate The copolymer which consists of a repeating unit derived from the repeating unit / dicyclopentanyl methacrylate derived from WHEREIN is glycidyl methacrylate to the copolymer of benzyl methacrylate, methacrylic acid, and dicyclopentanyl methacrylate. Can be obtained by reacting the rate.

The polystyrene reduced weight average molecular weight of (C) binder resin becomes like this. Preferably it is 5,000-100,000, More preferably, it is 6,000-80,000, Especially preferably, it is 7,000-60,000. When the molecular weight is in the above-described range, the coating film hardness is improved, the residual film ratio is also high, solubility in the developing solution of the unexposed part is good, and the resolution tends to improve, which is preferable.

The colored curable composition of this invention may further contain the (D) polymerization initiator. Examples of the polymerization initiator include triazine compounds, acetophenone compounds, biimidazole compounds, active radical generators and acid generators.

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl)- 6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5-triazine , 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2 -Methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5 -Triazine and 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine and the like, and preferably 2,4-bis (trichloromethyl) -6 -(4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1,3,5-triazine, 2 , 4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5-t Azine or 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, and more preferably 2,4-bis (trichloromethyl) -6-pipe Ronyl-1,3,5-triazine is mentioned.

As an acetophenone type compound, diethoxy acetophenone, 2-methyl-2- morpholino-1- (4-methylthio phenyl) propane- 1-one, 2-hydroxy-2- methyl-1-, for example Phenylpropan-1-one, benzyldimethyl ketal, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexylphenylketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2- (4-methylbenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butane Oligomers of -1-one and 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propane-1-one, and the like, and preferably 2-methyl-2-morr. Polyno-1- (4-methylthiophenyl) propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2- (4-methylbenzyl ) -2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, and more preferably 2-benzyl-2-dimethyl amino-1- (4-morpholinophenyl) Butan-1-one or 2- (4-methylbenzyl)- 2-dimethylamino-1- (4-morpholinophenyl) butan-1-one is mentioned.

As a biimidazole type compound, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'- tetraphenyl biimidazole, 2,2'-bis (2-chlorophenyl) -4 , 4 ', 5,5'-tetra (4-carboethoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (4- Bromophenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (2,4-dichlorophenyl) biimidazole, 2,2'-ratio Tetra (2-bromophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,4-dichlorophenyl) -4,4', 5,5'- Tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (m-methoxyphenyl) biimidazole, 2,2'-bis (2, 3-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,6-dichlorophenyl) -4,4', 5,5'-tetraphenyl ratio Imidazole, 2,2'-bis (2-nitrophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2-methylphenyl) -4,4', 5 , 5'-tetraphenylbiimidazole, and the like, and preferably 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole or 2,2'-bis (2,3-dichlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole.

Active radical generators generate active radicals by irradiation with light. Examples of the active radical generator include benzoin compounds, benzophenone compounds, thioxanthone compounds, oxime compounds, and the like.

As a benzoin type compound, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, etc. are mentioned, for example.

As a benzophenone type compound, for example, benzophenone, methyl o-benzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3 ', 4,4'- tetra (tert) -Butyl peroxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, etc. are mentioned.

As a thioxanthone type compound, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, and 1-chloro-4-, for example Propoxy city oxanthone etc. are mentioned.

As an oxime type compound, a 0-acyl oxime type compound is mentioned, for example, As a specific example, 1- (4-phenylsulfanylphenyl) -butane-1,2-dione 2-oxime-O-benzoate , 1- (4-phenylsulfanylphenyl) -octane-1,2-dione2-oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1-one oxime-O-acetate and 1- (4-phenylsulfanylphenyl) -butan-1-one oxime-0-acetate etc. are mentioned.

As active radical generators other than the above, for example, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, benzyl, 9,10-phenane Srenquinone, camphor quinone, methyl phenylglyoxylate, titanocene compound and the like.

As the acid generator, for example, 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium-p-toluenesulfonate , 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium-p-toluenesulfonate and di Onium salts, such as phenyl iodonium hexafluoro antimonate, nitrobenzyl tosylates, benzoin tosylate, etc. are mentioned.

In addition, some compounds mentioned above generate | occur | produce an acid simultaneously with an active radical, For example, a triazine type polymerization initiator is used also as an acid generator.

Content of (D) polymerization initiator is mass fraction with respect to the total amount of (B) polymeric compound and (C) binder resin, Preferably it is 0.1-25 mass%, More preferably, it is 1-20 mass%.

The colored curable composition of this invention may further contain (E) polymerization start adjuvant. (E) A polymerization start adjuvant is a compound normally used in combination with the (D) polymerization initiator, and used in order to accelerate superposition | polymerization of the polymeric compound in which polymerization was started by the (D) polymerization initiator.

(E) As an polymerization start adjuvant, an amine compound, an alkoxy anthracene type compound, a thioxanthone type compound, etc. are mentioned.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4-Dimethylaminobenzoic acid 2-ethylhexyl, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone, 4,4'- Bis (ethylmethylamino) benzophenone etc. are mentioned, Especially, 4,4'-bis (diethylamino) benzophenone is preferable.

Examples of the alkoxy anthracene-based compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and the like. Can be mentioned.

As a thioxanthone type compound, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, 1-chloro-4- Propoxy city oxanthone etc. are mentioned.

You may use (E) polymerization start adjuvant individually or in combination of 2 or more types. Moreover, a commercially available thing can also be used as (E) polymerization start adjuvant, As a commercial (E) polymerization start adjuvant, EAB-F (made by Hodogaya Chemical Co., Ltd., 4,4 ') is a brand name, for example. Organic amine compounds such as bis (diethylamino) benzophenone); and the like.

As a combination of the (D) polymerization initiator / (E) polymerization start adjuvant, it is 2, 4-bis (trichloromethyl) -6-piperonyl- 1,3, 5- triazine / 4,4'-, for example. Bis (diethylamino) benzophenone, diethoxyacetophenone / 4,4'-bis (diethylamino) benzophenone, 2-methyl-2-morpholino-1- (4-methylthiophenyl) propane-1 -One / 4,4'-bis (diethylamino) benzophenone, 2-hydroxy-2-methyl-1-phenylpropane-1-one / 4,4'-bis (diethylamino) benzophenone, benzyl Dimethyl ketal / 4,4'-bis (diethylamino) benzophenone, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one / 4,4 '-Bis (diethylamino) benzophenone, 1-hydroxycyclohexylphenyl ketone / 4,4'-bis (diethylamino) benzophenone, 2-hydroxy-2-methyl-1- [4- (1 Oligomer- / 4,4'-bis (diethylamino) benzophenone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butane- of -methylvinyl) phenyl] propan-1-one 1-one / 4,4'-bis (diethylamino) bene Zophenone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one / 4,4'-bis (diethylamino) benzophenone, 2- (4-methylbenzyl) 2-dimethylamino-1- (4-morpholinophenyl) butan-1-one / 4,4'-bis (diethylamino) benzophenone, etc. are mentioned, Preferably 2-benzyl-2- is mentioned. Dimethylamino-1- (4-morpholinophenyl) butan-1-one / 4,4'-bis (diethylamino) benzophenone, 2,4-bis (trichloromethyl) -6-piperonyl- 1,3,5-triazine / 4,4'-bis (diethylamino) benzophenone, 2- (4-methylbenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butane-1 -One / 4,4'-bis (diethylamino) benzophenone is mentioned.

When using (E) polymerization start adjuvant, the usage-amount is per 0.01 mass part of (D) polymerization initiators, Preferably it is 0.01-10 mass parts, More preferably, it is 0.01-5 mass parts.

The colored curable composition of this invention may contain the (F) solvent further. Examples of the solvent (F) include ethers, aromatic hydrocarbons, ketones, alcohols, esters, amides, and the like.

As ethers, for example, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol mono Methyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether acetate , Propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether acetate, methoxy butyl acetate, methoxy Pentilla And the like lactate, anisole, phenetole, and anisole methyl.

As aromatic hydrocarbons, benzene, toluene, xylene, mesitylene, etc. are mentioned, for example.

As ketones, for example, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and 4-hydroxy- 4-methyl-2 pentanone etc. are mentioned.

Examples of the alcohols include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, diacetone alcohol, glycerin, and the like.

As ester, For example, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, lactic acid Methyl, ethyl lactate, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methoxyacetate, methoxyacetate, methoxyacetate, ethoxyacetate, ethyl ethoxyacetate, 3-oxypropionate, 3- Ethyl oxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, Methyl 2-methoxypropionate, 2-methoxy ethylpropionate, propyl 2-methoxypropionate, methyl 2-epoxypropionate, 2-ethoxypropionate, 2-jade Methyl 2-methylpropionate, ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, Propyl rubinate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutyrate, ethyl 2-oxobutyrate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate and γ-butyrolactone Can be mentioned.

Examples of the amides include N, N-dimethylformamide, N, N-dimethylacetamide, and the like.

As a solvent other than the above, N-methylpyrrolidone, dimethyl sulfooxide, etc. are mentioned, for example.

You may use (F) solvent individually or in combination of 2 or more types, respectively.

As the solvent (F), propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate or diacetone alcohol are preferable.

Content of the (F) solvent is a mass fraction with respect to a colored curable composition, Preferably it is 70-90 mass%, More preferably, it is 75-88 mass%.

The colored curable composition of this invention may contain the (G) surfactant further. (G) As surfactant, silicone type surfactant which has a silicone type surfactant, a fluorine type surfactant, and a fluorine atom is mentioned.

As silicone type surfactant, surfactant etc. which have a siloxane bond are mentioned. Specifically, brand name Torre silicon DC3PA, Torre silicon SH7PA, Torre silicon DC11PA, Torre silicon SH21PA, Torre silicon SH28PA, Torre silicon 29SHPA, Torre silicon SH30PA, polyether modified silicone oil SH8400 (product made by Torre silicon), KP321 , KP322, KP323, KP324, KP326, KP340, KP341 (made by Shin-Etsu Silicone), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (manufactured by GE Toshiba Silicon Co., Ltd.) have.

As a fluorine type surfactant, surfactant etc. which have a fluorocarbon chain | strand are mentioned. Specifically, Flora FC430, Flora FC431 (manufactured by Sumitomo 3M Co., Ltd.), Mega Pack F142D, Mega Pack F171, Mega Pack F172, Mega Pack F173, Mega Pack F177, Mega Pack F183, Mega Pack F470, Mega pack F475, mega pack R30 (made by Dainippon Ink and Chemicals Co., Ltd.), f-top EF301, f-top EF303, f-top EF351, f-top EF352 (made by Shin-Akiwa Chemical Co., Ltd.), saffron S381, saffron S382, Saffron SC101, Saffron SC105 (made by Asahi Glass Co., Ltd.), E5844 (made by Daikin Fine Chemical Research Institute), BM-1000, BM-1100 (made by BM Chemie), etc. are mentioned.

As silicone type surfactant which has a fluorine atom, surfactant etc. which have a siloxane bond and a fluorocarbon chain | strand are mentioned. Specifically, Mega Pack R08, Mega Pack BL20, Mega Pack F475, Mega Pack F477, Mega Pack F443 (manufactured by Dainiphon Ink Chemical Co., Ltd.) and the like can be given.

You may use surfactant individually or in combination of 2 or more types.

The colored curable composition of this invention may contain the organic acid of molecular weight 1,000 or less. As an organic acid, the organic acid disclosed by Unexamined-Japanese-Patent No. 5-343631 is mentioned, for example. Specific examples include malonic acid, oxalic acid, succinic acid, glutaric acid, adipic acid, benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, citraconic acid, itaconic acid, mesaconic acid, fumaric acid, phthalic acid, acrylic acid and methacrylic acid. And, preferably, malonic acid, oxalic acid, fumaric acid or phthalic acid. Since the residue tends to be better by containing an organic acid having a molecular weight of 1,000 or less, it is preferable.

The colored curable composition of this invention may further contain additives, such as a filler, high molecular compounds other than (C) binder resin, an adhesion promoter, antioxidant, a ultraviolet absorber, an aggregation inhibitor, an organic amine compound, and (H) hardening | curing agent.

As a filler, microparticles | fine-particles, such as glass and alumina, are mentioned, for example.

(C) As high molecular compounds other than binder resin, polyvinyl alcohol, polyacrylic acid, a polyethyleneglycol monoalkyl ether, a polyfluoroalkyl acrylate, etc. are mentioned, for example.

Examples of the adhesion promoter include vinyl trimethoxysilane, vinyl triethoxysilane, vinyl tris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxymethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane and 3-mercaptopropyltri Methoxysilane, etc. are mentioned.

As antioxidant, 4,4'- thio-bis (6-tert- butyl- 3-methyl phenol) and triethylene glycol bis [3- (3-tert- butyl- 5-methyl- 4-) Hydroxyphenyl) propionate], 1,6-hexanediol-bis- [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], pentaerythritol-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate , 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,2'-methylenebis (4-methyl-6-tert-butylphenol), 4,4'-thio-bis (3-methyl-6- tert-butylphenol), 4,4'-butylidene-bis (3-methyl-6-tert-butylphenol), 1,1,3-tris (2-methyl-4-hydroxy-5-tert- Butylphenyl) butane and 1,3,5-tris (4-hydroxybenzyl) benzene and tetrakis [methylene-3- (3,5'-di-tert-butyl-4'-hydroxyfe Propionate)] methane, and the like.

As a ultraviolet absorber, For example, Benzotriazole type, such as 2- (2-hydroxy-3- tert- butyl- 5-methylphenyl) -5-chloro benzotriazole;

Benzophenones such as 2-hydroxy-4-octyloxybenzophenone;

Benzoate-based ultraviolet absorbers such as 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate;

And triazine-based ultraviolet absorbers such as 2- (4,6-diphenyl-1,3,5-triazin-2-yl) -5-hexyloxyphenol.

As an aggregation inhibitor, sodium polyacrylate etc. are mentioned, for example.

As the organic amine compound, for example, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, tert-butylamine, n-pentylamine, n-hexylamine, n-heptylamine monoalkyl amines such as n-octylamine, n-nonylamine, n-decylamine, n-undecylamine and n-dodecylamine;

Monocycloalkylamines such as cyclohexylamine, 2-methylcyclohexylamine, 3-methylcyclohexylamine, and 4-methylcyclohexylamine;

Methylethylamine, diethylamine, methyl-n-propylamine, ethyl-n-propylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, diisobutylamine, di-sec- Dialkylamines such as butylamine, di-tert-butylamine, di-n-pentylamine and di-n-hexylamine;

Monoalkyl monocycloalkylamines such as methylcyclohexylamine and ethylcyclohexylamine;

Dicycloalkylamines such as dicyclohexylamine;

Dimethylethylamine, methyldiethylamine, triethylamine, dimethyl-n-propylamine, diethyl-n-propylamine, methyldi-n-propylamine, ethyldi-n-propylamine, tri-n-propylamine Trialkylamines such as triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-tert-butylamine, tri-n-pentylamine and tri-n-hexylamine ;

Dialkyl monocycloalkylamines such as dimethylcyclohexylamine and diethylcyclohexylamine;

Monoalkyldicycloalkylamines such as methyldicyclohexylamine, ethyldicyclohexylamine and tricyclohexylamine;

Monoalkanes such as 2-aminoethanol, 3-amino-1-propanol, 1-amino-2-propanol, 4-amino-1-butanol, 5-amino-1-pentanol, 6-amino-1-hexanol Olamines;

Monocycloalkanolamines such as 4-amino-1-cyclohexanol;

Dialkanolamines such as diethanolamine, di-n-propanolamine, diisopropanolamine, di-n-butanolamine, diisobutanolamine, di-n-pentanolamine and di-n-hexanolamine;

Dicycloalkanolamines such as di (4-cyclohexanol) amine;

Trialkanolamines such as triethanolamine, tri-n-propanolamine, triisopropanolamine, tri-n-butanolamine, triisobutanolamine, tri-n-pentanolamine and tri-n-hexanolamine;

Tricycloalkanolamines such as tri (4-cyclohexanol) amine;

3-amino-1,2-propanediol, 2-amino-1,3-propanediol, 4-amino-1,2-butanediol, 4-amino-1,3-butanediol, 3-dimethylamino-1,2 Aminoalkanediols such as propanediol, 3-diethylamino-1,2-propanediol, 2-dimethylamino-1,3-propanediol and 2-diethylamino-1,3-propanediol;

Aminocycloalkanediols such as 4-amino-1,2-cyclohexanediol and 4-amino-1,3-cyclohexanediol;

Amino group-containing cycloalkanonemethanols such as 1-aminocyclopentanone methanol and 4-aminocyclopentanone methanol;

1-aminocyclohexanonemethanol, 4-aminocyclohexanonemethanol, 4-dimethylaminocyclopentanmethanol, 4-diethylaminocyclopentanmethanol, 4-dimethylaminocyclohexanemethanol, 4-diethylaminocyclohexanemethanol Amino group-containing cycloalkanethanols;

β-alanine, 2-aminobutyric acid, 3-aminobutyric acid, 4-aminobutyric acid, 2-aminoisoacetic acid, 3-aminoisoacetic acid, 2-aminogilic acid, 5-aminogilacetic acid, 6-aminocapronic acid, 1 Aminocarboxylic acids such as aminocyclopropanecarboxylic acid, 1-aminocyclohexanecarboxylic acid, and 4-aminocyclohexanecarboxylic acid;

Aniline, o-methylaniline, m-methylaniline, p-methylaniline, p-ethylaniline, pn-propylaniline, p-isopropylaniline, pn-butylaniline, p-tert-butylaniline, 1-naphthylamine Aromatic amines such as 2-naphthylamine, N, N-dimethylaniline, N, N-diethylaniline and p-methyl-N, N-dimethylaniline;

aminobenzyl alcohols such as o-aminobenzyl alcohol, m-aminobenzyl alcohol, p-aminobenzyl alcohol, p-dimethylaminobenzyl alcohol and p-diethylaminobenzyl alcohol;

aminophenols such as o-aminophenol, m-aminophenol, p-aminophenol, p-dimethylaminophenol and p-diethyl aminophenol;

Amino benzoic acids, such as m-amino benzoic acid, p-amino benzoic acid, p-dimethylamino benzoic acid, and p-diethyl amino benzoic acid, etc. are mentioned.

By the addition of the organic amine compound, it is possible to give a pixel excellent in adhesion to the substrate without causing residue on the substrate of the unexposed portion during development.

(H) As a hardening | curing agent, the compound which can react with the carboxyl group in (C) binder resin by crosslinking, and can crosslink (C) binder resin, the compound which can superpose | polymerize independently and harden a coloring pattern, etc. are mentioned, for example. For example, an epoxy compound, an oxetane compound, etc. are mentioned, An oxetane compound is used preferably.

As the epoxy compound, for example, a bisphenol A epoxy resin, a hydrogenated bisphenol A epoxy resin, a bisphenol F epoxy resin, a hydrogenated bisphenol F epoxy resin, a novolak epoxy resin, another aromatic epoxy resin, and an alicyclic epoxy resin. Epoxy resins such as heterocyclic epoxy resins, glycidyl ester resins, glycidyl amine resins, epoxidized oils, and aliphatic, alicyclic or aromatic groups other than brominated derivatives, epoxy resins and brominated derivatives of these epoxy resins. Epoxy compounds, epoxides of (co) polymers of butadiene, epoxides of (co) polymers of isoprene, (co) polymers of glycidyl (meth) acrylate, triglycidyl isocyanurate, and the like.

Examples of the oxetane compound include carbonate bis oxetane, xylylene bis oxetane, adipate bis oxetane, terephthalate bis oxetane, and cyclohexanedicarboxylic acid bis oxetane.

When an epoxy compound, an oxetane compound, etc. are contained as a hardening | curing agent, it is preferable to contain the compound which can ring-open-polymerize the epoxy group of an epoxy compound, and the oxetane skeleton of an oxetane compound. As this compound, polyhydric carboxylic acid, polyhydric carboxylic anhydride, etc. are mentioned, for example.

Examples of the polycarboxylic acids include phthalic acid, 3,4-dimethylphthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, trimellitic acid, 1,4,5,8-naphthalenetetracarboxylic acid, 3,3 ', 4 Aromatic polyhydric carboxylic acids such as, 4'-benzophenone tetracarboxylic acid;

Aliphatic polyvalent carboxylic acids such as succinic acid, glutaric acid, adipic acid, 1,2,3,4-butanetetracarboxylic acid, maleic acid, fumaric acid and itaconic acid;

Hexahydrophthalic acid, 3,4-dimethyltetrahydrophthalic acid, hexahydroisophthalic acid, hexahydroterephthalic acid, 1,2,4-cyclopentanetricarboxylic acid, 1,2,4-cyclohexanetricarboxylic acid, cyclopentanetetracar Alicyclic polyhydric carboxylic acids, such as this acid and 1,2,4,5-cyclohexane tetracarboxylic acid, etc. are mentioned.

As polyhydric carboxylic anhydride, For example, Aromatic polyhydric carboxylic anhydrides, such as a phthalic anhydride, a pyromellitic anhydride, trimellitic anhydride, 3,3 ', 4,4'- benzophenone tetracarboxylic dianhydride;

Aliphatic polyhydric carboxylic anhydrides such as itaconic anhydride, succinic anhydride, citraconic anhydride, dodechenyl anhydride, tricarvallylic acid, maleic anhydride, and 1,2,3,4-butanetetracarboxylic dianhydride;

Hexahydrophthalic anhydride, 3,4-dimethyltetrahydrophthalic anhydride, l, 2,4-cyclopentanetricarboxylic anhydride, 1,2,4-cyclohexanetricarboxylic acid anhydride, cyclopentanetetracarboxylic dianhydride, 1 Alicyclic polyhydric carboxylic acid anhydrides such as 2,4,5-cyclohexanetetracarboxylic acid dianhydride, hymic acid anhydride and nadic anhydride;

And ester bond-containing carboxylic acid anhydrides such as ethylene glycol bistrimellitate acid and glycerin tristrimellitate anhydride.

As carboxylic anhydrides, you may use what is marketed as an epoxy resin hardening | curing agent. As an epoxy resin hardening | curing agent, Adeka hydroner EH-700 (made by Asahi Denka Kogyo Co., Ltd.), Recassette HH, MH-700 (all are the Shin-Nihon Chemical Co., Ltd. product) etc. are mentioned, for example. have.

You may use a hardening | curing agent individually or in combination of 2 or more types.

As a method of forming the pattern of a color filter using the colored curable composition of this invention, the colored curable composition of this invention is made into the board | substrate or another resin layer (for example, the other colored curable composition layer formed first on a board | substrate, etc.). A so-called photolithography method or a colored curable composition which is applied on the surface of the sheet), and removes volatile components such as a solvent to form a colored layer, exposes the colored layer through a photomask, develops it, and heats it again if necessary. The inkjet method etc. which apply | coat to a board | substrate or another resin layer using an inkjet apparatus, remove volatile components, such as a solvent, form a colored layer, and harden | cure by at least one of heating or exposure are mentioned.

According to the present invention, a color filter excellent in brightness and contrast can be produced. The color filter obtained in this way is used suitably for a liquid crystal display device.

(Example)

Hereinafter, the present invention will be described in more detail with reference to Examples.

Synthesis Example 1

<Synthesis of Coloring Agent (A-1)>

In a 100 mL four-necked flask, 106.4 g (400 mmol) tetrachlorophthalonitrile, 14.3 g (105 mmol) zinc chloride, 84.0 g (3000 mmol) urea, 19.9 g (30 mmol) ammonium molybdate tetrahydrate and methyl 100 mL of naphthalene was added, and it heated at 200 degreeC under nitrogen atmosphere for 6 hours. The precipitate was collected by filtration, washed with methanol followed by warm water at 60 ° C, and dried under reduced pressure at 60 ° C to obtain 29.7 g of hexadecachlorozincphthalocyanine.

Next, to a 500 mL four-necked flask, 90.7 g (680 mmol) of anhydrous aluminum chloride and 11.7 g (200 mmol) of sodium chloride were mixed at 40 ° C, 25.0 g (22 mmol) of hexadecachlorozincphthalocyanine was added thereto, followed by stirring. 60.0 g (751 mmol) of bromine were dripped under stirring, and it heated up to 130 degreeC over 20 hours, and hold | maintained for 1 hour. The obtained reactant was taken out with water, and the chlorinated bromide phthalocyanine preparation pigment was deposited. The chlorinated bromide phthalocyanine crude pigment slurry was filtered, and then washed with warm water at 60 ° C, followed by washing with 1% sodium hydrogen sulfate solution, followed by further washing with 60 ° C warm water, followed by drying under reduced pressure at 60 ° C. Thus, 21,3 g of purified chlorinated bromide phthalocyanine auxiliary pigment was obtained.

Next, 20 g of chlorinated bromide phthalocyanine prepared pigments, 60 g of sodium chloride, and 20 g of diethylene glycol were added to a kneader, and milled at 90 ° C. for 5 hours, followed by extraction with 100 parts by weight of an 80 ° C. aqueous solution, followed by 30 minutes. After stirring, the mixture was filtered, washed with warm water at 60 ° C, dried under reduced pressure at 60 ° C, and pulverized to obtain 12.8 g of chlorinated zinc bromide phthalocyanine pigment.

As a result of analyzing the obtained chlorinated brominated phthalocyanine pigment by the flask combustion treatment ion chromatograph method, the ratio of the substituent on a zinc phthalocyanine frame | skeleton was bromine 14.6, chlorine 1.4, and hydrogen 0.

Synthesis Example 2

<Synthesis of Coloring Agent (A-2)>

In a 1000 mL four-necked flask, 89.1 g (660 mmol) of sulfyl chloride, 90.7 g (680 mmol) of anhydrous aluminum chloride, 12.3 g (210 mmol) of sodium chloride were mixed at 40 ° C, and 25.0 g (43.3 mmol) of zinc phthalocyanine. After adding and stirring, 60.0 g (751 mmol) of bromine were dripped under stirring, it heated up to 130 degreeC over 20 hours, and hold | maintained for 1 hour. The obtained reaction product was taken out in water, and the chlorinated bromide phthalocyanine preparation pigment was deposited. This chlorinated bromide phthalocyanine crude pigment slurry was filtered, and then washed with warm water at 60 ° C, then with 1% sodium hydrogen sulfate solution, again with warm water at 60 ° C, dried under reduced pressure at 60 ° C, and 22.5 g The purified chlorinated bromide phthalocyanine preparation pigment of was obtained.

Next, 20 g of chlorinated bromide phthalocyanine prepared pigments, 60 g of sodium chloride, and 20 g of diethylene glycol were added to a kneader, and milled at 90 ° C. for 5 hours, followed by extraction with 100 parts by weight of an 80 ° C. aqueous solution, followed by 30 minutes. After stirring, the mixture was filtered, washed with warm water at 60 ° C, dried under reduced pressure at 60 ° C, and pulverized to obtain 14.3 g of zinc chloride chlorobromide.

As a result of analyzing the obtained chlorinated brominated phthalocyanine pigment by the flask combustion treatment ion chromatograph method, the ratio of the substituent on a zinc phthalocyanine skeleton was bromine 13.4, chlorine 2.2, and hydrogen 0.4.

Synthesis Example 3

<Synthesis of Coloring Agent (A-3)>

Synthesis of barbituric acid azo dye represented by formula (2-4)

300 g of water was added to 30 g (61 mmol) of 2,2'-benzidine disulfonic acid (containing 30% of water) represented by Formula (27), and then adjusted to pH 7-8 with 30% sodium hydroxide aqueous solution under ice cooling. . The following operations were performed under ice cooling. 12.6 g (183 mmol) of sodium nitrite was added and stirred for 30 minutes. A small amount of 38.1 g of 35% hydrochloric acid was added to make a brown solution, followed by stirring for 2 hours. An aqueous solution in which 5.3 g (61 mmol) of amid sulfate was dissolved in 57.4 g of water was added to the reaction solution, followed by stirring, to obtain a suspension containing a diazonium salt.

372 g of water was added to 18.6 g (146 mmol) of N, N'-dimethylbarbituric acid represented by the formula (28), and then adjusted to pH 8-9 with an aqueous 30% sodium hydroxide solution under ice-cooling.

The following operation was performed under ice cooling. The aqueous solution of alkaline barbiturate was stirred to give a colorless solution, and a suspension containing diazonium salt was added dropwise with a pump while adjusting the pH to 8-9 with 30% sodium hydroxide solution. After completion of the dropwise addition, the mixture was stirred for 3 hours to obtain a yellow suspension. The yellow solid obtained by filtration was dried at 60 degreeC under reduced pressure, and 15 g (21 mmol, yield 34%) of the azo compound represented by Formula (29) was obtained.

To a flask equipped with a cooling tube and a stirring device, 5 g (7 mmol) of the azo compound represented by the formula (29), 50 g of chloroform and 2 g (3 mmol) of N, N-dimethylformamide were added thereto, followed by stirring. 6 g (54 mmol) of thionyl chlorides were added dropwise while keeping the temperature at or below. It heated up at 50 degreeC after completion | finish of dripping, it hold | maintained and reacted for 5 hours at the same temperature, and it cooled at 20 degreeC after that. A mixture of 3 g (20 mmol) of 3-aminophenylbutane and 10 g (103 mmol) of triethylamine was added dropwise while maintaining the reaction solution after cooling at 20 DEG C or lower under stirring. Thereafter, the reaction was stirred at the same temperature for 5 hours. Subsequently, the solvent was distilled off from the reaction mixture by a rotary evaporator, and then a small amount of methanol was added thereto, followed by vigorous stirring. This mixture was added to the mixed liquid of 29 g of acetic acid and 300 g of ion-exchanged water with stirring to precipitate crystals. Precipitated crystals were separately filtered, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 6 g (6 mmol, yield 78%) of the azo compound represented by formula (7-4).

The azo compound obtained in this Example was subjected to LC-MS analysis under the following conditions.

Device ; Agilent 1100 (manufactured by Agilent Technology, Inc.)

Detector; UV detector; 254 nm

column ; Sumipax ODS (product made by Sumitomo analysis center)

Elution solvent; Solvent system with 0.1% trifluoromethylacetic acid added to the water-acetonitrile mixed solvent

The content of each azo compound was calculated from the peak area. As a result, the azo compound represented by Formula (7-4) was detected as a compound of molecular weight 940, and the area percentage value with respect to the whole peak area was 98%.

Synthesis Example 4

<Synthesis of Coloring Agent (A-4)>

Synthesis of pyridoneazo dyes represented by formula (3-12)

3000 g of water was added to 100 g (203 mmol) of 2,2'-benzidine disulfonic acid (containing 30% of water) represented by Formula (27), and then adjusted to pH 7-8 with 30% sodium hydroxide aqueous solution under ice cooling. . The following operations were performed under ice cooling. 56 g (812 mmol) of sodium nitrite was added and stirred for 30 minutes. 150 g of 35% hydrochloric acid was added in small portions to form a brown solution, followed by stirring for 2 hours. An aqueous solution in which 38 g (406 mmol) of amid sulfate was dissolved in 380 g of water was added to the reaction solution, followed by stirring to obtain a suspension containing a diazonium salt.

After adding 1000 g of water to 76 g (426 mmol) of 1-ethyl-3-cyano-4-methyl-6-hydroxypyrid-2-one shown by Formula (30), 30% sodium hydroxide under ice-cooling The pH was adjusted to 8-9 with an aqueous solution.

The following operation was performed under ice cooling. After stirring the alkaline aqueous solution of the pyridones to give a colorless solution, a suspension containing a diazonium salt was added dropwise with a pump while adjusting to pH 8-9 with 30% aqueous sodium hydroxide solution. After completion of the dropwise addition, the mixture was stirred for 3 hours to obtain a yellow suspension. The yellow solid obtained by filtration was dried at 60 degreeC under reduced pressure, and 137 g (204 mmol, yield 100%) of the azo compound represented by Formula (31) was obtained.

5 g (7 mmol) of the azo compound represented by the formula (31) obtained by the above operation, 50 g of chloroform and 2.4 g (33 mmol) of N, N-dimethylformamide were charged into a flask equipped with a cooling tube and a stirring device. 7 g (59 mmol) of thionyl chlorides were dripped and added, maintaining 20 degrees C or less, stirring. After completion of the dropwise addition, the temperature was raised to 50 ° C, held at the same temperature for 5 hours for reaction, and then cooled to 20 ° C. A mixture of 4 g (30 mmol) of 1,5-dimethylhexylamine and 12 g (119 mmol) of triethyl amine was added dropwise while keeping the reaction solution after cooling at 20 ° C. or less under stirring. Thereafter, the reaction was stirred overnight at the same temperature. Subsequently, the solvent was distilled off from the reaction mixture by a rotary evaporator, and then a small amount of methanol was added thereto, followed by vigorous stirring. This mixture was added to the mixed liquid of 29 g of acetic acid and 300 g of ion-exchanged water with stirring to precipitate crystals. The precipitated crystals were separately filtered, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 6 g (6 mmol, yield 80%) of the azo compound represented by the formula (3-12).

  The azo compound obtained in the present Example was subjected to the same structural analysis as above. The azo compound represented by the formula (3-12) was detected as a compound having a molecular weight of 944, and the area percentage value with respect to the total peak area was 58.3. Was%. Moreover, the monosulfonamide azo compound represented by Formula (40) was detected as a compound of molecular weight 833, and the area percentage value with respect to the whole peak area was 30.1%.

Synthesis Example 5

<Synthesis of Resin (C-1)>

333 g of propylene glycol monomethyl ether acetate was introduced into a 100 ml flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping lot, and a gas introduction tube. Thereafter, nitrogen gas was introduced into the flask using a gas introduction pipe, and the atmosphere in the flask was replaced with nitrogen gas. Then, after heating up the solution in a flask at 100 degreeC, dicyclopentanyl methacrylate (FA-513M; the Hitachi Chemicals Co., Ltd.) 22.0 g (0.10 mol), benzyl methacrylate 70.5 g (0.40 mol) The mixture consisting of 43.0 g (0.5 mol) of methacrylic acid, 3.6 g of azobisisobutylonitrile and 164 g of propylene glycol monomethyl ether acetate was added dropwise to the flask over 2 hours using a dropping lot, and then the dropping was completed. Stirring was continued for 5 hours at 100 ° C.

After completion of the stirring, air was introduced into the flask using a gas introduction tube, and the atmosphere in the flask became air, followed by 35.5 g [0.25 mol of glycidyl methacrylate (mol fraction relative to methacrylic acid used in this reaction). , 50 mol%)], 0.9 g of trisdimethylaminomethylphenol and 0.145 g of hydroquinone were charged into a flask, and the reaction was continued at 110 ° C for 6 hours to obtain a solution containing resin (C-1) (solid content). 38.7 mass%, acid value 82 mg KOH / g).

Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of a polymer having an acid group such as carboxylic acid, and is usually determined by titration using an aqueous potassium hydroxide solution with known concentration.

The polystyrene reduced weight average molecular weight of obtained resin (C-1) was 9,800.

In the measurement of the polystyrene conversion weight average molecular weight of said (C-1) binder resin, it carried out on condition of the following using GPC method.

Device ; HLC-8120 GPC (manufactured by Tosoh Corporation)

column ; TSK-GELG2000HXL

Column temperature; 40 ℃

Solvent; THF

Flow rate; 1.0 mL / min

Test liquid solids concentration; 0.001-0.01 mass%

Injection volume: 50 μL

Detector; RI

Calibration standard; TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500, A-500 (made by Tosoh Corporation)

Synthesis Example 6

<Synthesis of Resin (C-2)>

182 g of propylene glycol monomethyl ether acetate was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping lot, and a nitrogen inlet tube. Thereafter, nitrogen gas was introduced into the flask using a gas introduction pipe, and the atmosphere in the flask was replaced with nitrogen gas. Then, the solution in a flask was heated up at 100 degreeC, 70.5 g (0.40 mol) of benzyl methacrylates, 43.0 g (0.5 mol) of methacrylic acid, and the monomethacrylate of a tricyclodecane skeleton (made by Hitachi Chemical Co., Ltd.) To a mixture consisting of 22.0 g (0.10 mol) of FA-513 M) and 136 g of propylene glycol monomethyl ether acetate, a solution containing 3.6 g of 2,2'-azobisisobutylonitrile was added dropwise, and continued at 100 ° C. Stirred.

After the completion of stirring, the atmosphere in the flask was changed from nitrogen to air, and 35.5 g [0.25 mol of glycidyl methacrylate ((50 mol% of the carboxyl groups of methacrylic acid used in the reaction)]] and trisdimethylaminomethylphenol 0.9 g and 0.145 g of hydroquinone were charged into a flask and reacted at 110 ° C to obtain a solution containing the resin (C-2) (solid content of 28.9 mass%, acid value 79 mg KOH / g).

The weight average molecular weight of polystyrene conversion was measured like resin (C-1). The weight average molecular weight of polystyrene conversion of resin (C-2) was 3.Ox10 <^4> .

The component used by a present Example is as follows, and it abbreviate | omits and shows below.

(A-1) Colorant (pigment): Dye obtained in Synthesis Example 1

(A-2) Colorant (pigment): Dye obtained in Synthesis Example 2

(A-3) Colorant (dye): Dye obtained in Synthesis Example 3

(A-4) Colorant (dye): Dye obtained in Synthesis Example 4

(A-5) Colorant (dye): Compound (C.I. solvent yellow 162) represented by formula (3-1)

(A-6) Colorant (dye): Compound represented by Formula (21) (cyanine dye; NK-3212: manufactured by Hayashibara Biochemistry Research Institute)

(A-7) Colorant (pigment): C.I. Pigment Yellow 150

(A-8) Colorant (dye): Compound represented by formula (A-8)

(A-9) Colorant (dye): Compound represented by formula (A-9)

(A-10) Colorant (pigment): C.I. Pigment green 58

(B-1) Polymerizable Compound: DPHA (manufactured by Nihon Kayaku Co., Ltd.)

(C-1) Binder Resin: Resin (C-1) obtained in Synthesis Example 5 (propylene glycol monomethyl ether acetate solution having a solid content of 38.7% by mass)

(C-2) Binder Resin: Resin (C-2) obtained in Synthesis Example 6 (propylene glycol monomethyl ether acetate solution having a solid content of 28.9% by mass)

(D-1) polymerization initiator: 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one

(D-2) Polymerization initiator: OXE-01 (made by Chiba Specialty Chemical Co., Ltd.)

(E-1) Polymerization start adjuvant: 4,4'-bis (diethylamino) benzophenone

(F-1) Solvent: Propylene Glycol Monomethyl Ether

(F-2) Solvent: Propylene glycol monomethyl ether acetate

(F-3) Solvent: Ethyl 3-ethoxypropionate

(G-1) Surfactant: Mega Pack F475 (manufactured by Dainippon Ink and Chemicals, Inc.)

Pigment Dispersant 1: Dispervic 2001 (manufactured by Vikchem Co., Ltd.) (a mixed solution of propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, and ethylene glycol monobutyl ether, having a solid content of 46.0% by mass)

(Example 1)

[Preparation of Pigment Dispersion 1]

(A-1) 8.500 parts by mass

(C-1) 6.589 parts by mass (solid content: 2.550 parts by mass)

(Pigment dispersant) 7.761 parts by mass (solid content conversion: 3.570 parts by mass)

(F-1) 13.575 parts by mass

(F-2) 13.575 parts by mass

The composition was placed in a 143 ml mayonnaise bottle, and 166.500 parts by mass of zirconia beads having a diameter of 0.5 mm were further added and sealed, and after vibrating with a paint conditioner for 20 hours, it was filtered to obtain Pigment Dispersion 1.

[Preparation of Colored Curable Composition 1]

Next, each component was mixed by the following formulation and the coloring curable composition 1 was obtained.

Pigment Dispersion 1 3.775 parts by mass

(A-6) 0.200 parts by mass

(B-1) 0.399 parts by mass

(C-1) 1.050 parts by mass (solid content conversion value: 0.406 parts by mass)

(D-1) 0.142 parts by mass

(E-1) 0.047 parts by mass

(F-1) 4.000 parts by mass

(F-3) 0.385 parts by mass

(G-1) 0.001 parts by mass

[Formation of Coating Film]

Next, after apply | coating the colored curable composition 1 obtained above on the glass (EAGLE2000; the Corning company make) by the spin coat method, the volatile component was volatilized for 3 minutes at 100 degreeC, and the colored curable composition film was formed. After cooling, this colored curable composition film was irradiated with i line | wire (wavelength 365 nm), and was exposed. An ultrahigh pressure mercury lamp was used for the light source of i-line, and it irradiated after making it into parallel light. The irradiation light amount was 200 mJ / cm 2. Subsequently, post-baking was performed at 220 degreeC for 20 minutes, and the colored curable composition film of y = 0.600 was obtained by CIE-XYZ colorimeter. The film thickness of the colored curable composition film was 2.2 µm.

[Evaluation 1] brightness evaluation

The chromaticity of the obtained colored curable composition film was measured using a colorimeter (OSP-SP-200: manufactured by Olympus Corporation), and the result was x = 0.289, y = 0.600, and Y (brightness) = 58.62.

[Evaluation 2] contrast evaluation

It was 9180 when the contrast value of the obtained colored curable composition film was measured with the blank value 10000 using the contrast colorimeter (CT-1; the Tsubosaka Electric company make).

As an evaluation criterion of the contrast of the colored curable composition film, when the contrast value is 8000 or more, small knitting is hardly confirmed, showing good characteristics as a color filter, and when the contrast value is more than 5800 and 8000 or less, some small knitting properties Although it is confirmed, it is a level which does not have a problem practically in a color filter, and when a contrast value is 5800 or less, small fragmentation can be confirmed reliably, and it is a level which has a problem as a color filter.

[Evaluation 3] heat resistance evaluation

The chromaticity of the obtained colored curable composition film was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS).

Subsequently, the obtained colored curable composition film was further heated in an oven at 120 ° C. for 120 minutes, the chromaticity of the colored curable composition film after heating was measured in the same manner, and the color difference (ΔEab *) before and after heating was found. It was.

As the evaluation criteria for the color difference, almost no color change is observed when ΔEab * is 5 or less, and exhibits good characteristics as a color filter, and when ΔEab * is more than 5 and 10 or less, a slight color change is confirmed. If it is a level without an image problem and (DELTA) Eab * is 10 or more, a color change can be confirmed reliably and it is a level with a problem as a color filter.

[Evaluation 4] Light resistance evaluation

A UV cut filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co .; blocks light of 380 nm or less) was placed on the obtained colored curable composition film, and the xenon lamp light was subjected to a xenon lamp light by a light resistance tester (SUNTEST CPS +: manufactured by Toyo Seiki Co., Ltd.) for 48 hours. Investigate.

It was 2.8 when the chromaticity of the colored curable composition film | membrane after irradiation was measured, and the color difference before and behind irradiation was calculated | required.

As a criterion for evaluating the color difference, the color change is hardly confirmed when ΔEab * is 5 or less as described above, showing good characteristics as a color filter, and when ΔEab * is more than 5 and 10 or less, a slight color change is confirmed. It is a level which is satisfactory practically in a color filter, and if (DELTA) Eab * is more than 10, a color change can be confirmed reliably, and it is a level with a problem as a color filter.

(Examples 2 to 6)

Colored curable compositions 2-6 were obtained like Example 1 except having changed the composition of the colored curable composition as shown in Table 1.

Moreover, about coloring agents (A-2) and (A-7), except changing the coloring agent (A-1) of [preparation of pigment dispersion 1] into (A-2) and (A-7), respectively. In the same manner, a pigment dispersion was prepared and used for evaluation.

The obtained colored curable compositions 2-6 were evaluated like Example 1, and the result was shown in Table 2.

(Example 7)

[Preparation of Pigment Dispersion 2]

(A-10) 40 parts by mass

(Pigment dispersant) 5 parts by mass

(F-2) 137 parts by mass

Were mixed and the pigment was fully dispersed using a bead mill to obtain pigment dispersion 2.

[Preparation of Colored Curable Composition 7]

Next, each component was mixed by the following formulation and the coloring curable composition 7 was obtained.

Pigment Dispersion 2 182 parts by mass

(A-8) 24 parts by mass

(B-1) 50 parts by mass

(C-2) 157 parts by mass

(D-2) 15 parts by mass

(F-2) 289 parts by mass

[Formation of Pattern]

After apply | coating the coloring curable composition 7 on the 2-inch square glass substrate (Eagle 2000; Corning Corporation make) by the spin coat method, it prebaked at 100 degreeC for 3 minutes. After cooling, the gap between the substrate coated with the colored curable composition and a quartz glass photomask having a pattern was set to 100 µm, and was then exposed to air using an exposure machine (TME-150 RSK; The light was irradiated with an exposure dose (365 nm standard) of mJ / cm 2. After light irradiation, the coating film was immersed in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23 ° C. for 80 seconds. After washing with water, post-baking was carried out at 220 ° C. for 20 minutes in an oven. It was. It was 2.2 micrometers when the film thickness of the obtained hardening pattern after cooling was measured using the film thickness measuring apparatus (DEKTAK3; Japan Vacuum Technology Co., Ltd. product).

[evaluation]

About the coating film on the obtained glass substrate, xy chromaticity coordinates (x, y) and brightness (Y) in the XYZ colorimeter of CIE were measured using a C light source with a colorimeter (OSP-SP-200: manufactured by Olympus Co., Ltd.). And contrast was measured using the contrast system (color chromaticity meter BM-5A; Topcon Corporation). The results are shown in Table 3. Good results are also obtained for heat resistance evaluation and light resistance evaluation.

(Example 8)

The colored curable composition 8 was obtained like Example 7 except having changed (A-8) into (A-9). In the same manner as in Example 7, a pattern having a film thickness of 2.2 mu m was formed and evaluated. The results are shown in Table 3. Also about heat resistance evaluation and light resistance evaluation, a favorable result is obtained.

(Example 9)

Colored curable compositions 1-8 are apply | coated to the board | substrate with a bank using an inkjet apparatus, and a colored coating film is formed.

When the colored curable composition of this invention is used, the color filter excellent in the brightness and contrast can be manufactured.

Claims (8)

The coloring curable composition containing (A) coloring agent and (B) polymeric compound, and (A) coloring agent is a coloring agent containing the pigment and yellow dye represented by Formula (1).

[In Formula (1), A <^1> -A <^16> respectively independently represents a hydrogen atom, a chlorine atom, or a brom atom.] The method of claim 1, The yellow dye is a yellow dye containing at least one dye selected from the group consisting of barbituric acid azo dyes, pyridone azo dyes, pyrazolone azo dyes, quinophthalone dyes and cyanine dyes. The colored curable composition characterized by the above-mentioned. The method of claim 2, The barbituric acid azo dye is a dye represented by Formula (2), The coloring curable composition characterized by the above-mentioned.

[In formula (2), T <^1> and T <^2> represent an oxygen atom or a sulfur atom each independently. R ³¹ to R ³⁴ each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, and 7 to 20 carbon atoms that may have a substituent. The C2-C10 acyl group which may have an aralkyl group or a substituent is shown. R ³⁵ to R ⁴² each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, a carboxyl group, a sulfo group, a sulfamoyl group, or an N-substituted sulfamoyl group. The hydrogen atom contained in the aliphatic hydrocarbon group may be substituted with a halogen atom.] The method of claim 2, The pyridone azo dye is a dimer formed from the compound represented by Formula (3), the salt of the compound represented by Formula (3), or the compound represented by Formula (3), The coloring curable composition characterized by the above-mentioned.

[In Formula (3), Z is a C1-C12 aliphatic hydrocarbon group, a C1-C8 alkoxyl group, a hydroxyl group, a carboxyl group, a carbamoyl group, a sulfo group, and a sulfamoyl which may have a halogen atom and a substituent. A phenyl group having one or two substituents or at least one substituent selected from the group consisting of a diary and an N-substituted sulfamoyl group, or a halogen atom or a C1-C12 aliphatic hydrocarbon group which may have a substituent, C1-C1 8 represents a naphthyl group having 1 to 3 substituents selected from the group consisting of an alkoxyl group, hydroxyl group, carboxyl group, carbamoyl group, sulfo group, sulfamoyl group and N-substituted sulfamoyl group . R ²¹ represents a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms, a carboxyl group or a trifluoromethyl group. R ²² represents a hydrogen atom, a cyano group, a carbamoyl group, an N-substituted carbamoyl group, a sulfamoyl group, or a sulfo group. R ²³ is a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, or carbon number 7 which may have a substituent An aralkyl group having 20 to 20 carbon atoms, a heterocyclic group having 3 to 20 carbon atoms, a carbamoyl group, an N-substituted carbamoyl group, or an alkyloxycarbonyl group having 2 to 20 carbon atoms which may have a substituent or a substituent may be used. An aryloxycarbonyl group having 7 to 30 carbon atoms, an acyl group having 2 to 20 carbon atoms which may have a substituent, an aliphatic sulfonyl group having 1 to 30 carbon atoms which may have a substituent or an arylsulfonyl group having 6 to 30 carbon atoms which may have a substituent Is displayed.] The method according to any one of claims 1 to 4, (C) Colored curable composition containing binder resin further. The pattern formed by the photolithographic method or the inkjet method using the colored curable composition in any one of Claims 1-4. The color filter containing the pattern of Claim 6. A liquid crystal display device comprising the color filter according to claim 7.