JP6808921B2 - Compound and color curable resin composition - Google Patents

Description

The present invention relates to compounds and color curable resin compositions.

Dyes are used, for example, in the fields of textile materials, liquid crystal display devices, inkjets, and the like for color display using reflected light or transmitted light. As such a dye, for example, rhodamine B having a xanthene skeleton and represented by the following formula (Rb) is widely known (Non-Patent Document 1).

Yutaka Hosoda, "New Dye Chemistry", Gihodo Co., Ltd., 1st Edition, May 1973, p. 274

Conventionally known color-curable resin compositions containing the above compounds have not been sufficiently satisfactory in terms of heat resistance.

The present invention includes the following inventions.
[1] A color curable resin composition containing a colorant, a resin, a polymerizable compound and a polymerization initiator containing a compound represented by the formula (IA).

Wherein (I-A), ^{Q 1} and ^{Q 2} each independently represent an oxygen atom or a sulfur atom.
R ^1C and R ^2C each represent a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and −CH ₂ − contained in the hydrocarbon group is , -O-, -CO-, or -N (R ^112C ) ^-may be replaced.
R ^112C represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^{5C _{are, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - T +, -CO 2 H, -CO 2 - T +, -CO 2 R 8C, -SO 3 R 8C or -SO Represents ₂ N (R ^9C ) (R ^10C ).
T ⁺ represents ⁺ N (R ^11C ) ₄ , Na ⁺ or K ⁺ , and R ^11C may be the same or different.
R ^11C represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^8C represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^9C and R ^10C represent monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and are contained in the saturated aliphatic hydrocarbon groups. CH ₂ − may be replaced by −O−, −CO−, −NH− or −N (R ^8C ) −.
R ^6C and R ^7C represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other.
m1 represents an integer from 0 to 5. When m1 is 2 or more, the plurality of R ^5Cs may be the same or different.
d represents an integer from 0 to 5.
P ⁻ represents a counterion. ]

[In the formula (I), R ¹ and R ² represent monovalent hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and the hydrocarbon groups thereof. The included −CH ₂₋ may be replaced by −O−, −CO−, or −N (R ¹² ) −.
R ¹² represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^{5 _{is, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8, -SO 3 R 8 or -SO ₂ Represents N (R ⁹ ) (R ¹⁰ ).
Z ⁺ represents ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and R ¹¹ may be the same or different.
R ¹¹ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ⁹ and R ¹⁰ represent monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and are contained in the saturated aliphatic hydrocarbon group-. CH ₂ - is, -O -, - CO -, - NH- or -N ^{(R 8)} - can have me every conversion at.
R ⁶ and R ⁷ represent hydrogen atoms or alkyl groups having 1 to 6 carbon atoms independently of each other.
m represents an integer from 0 to 5. When m is 2 or more, the plurality of R ^5s may be the same or different.
a represents an integer from 0 to 5.
X ⁻ represents a counterion. ]
[3] The colored curable resin composition according to [1] or [2], which further contains a green pigment.
[4] The colored curable resin composition according to [3], wherein the green pigment is at least one selected from the group consisting of a halogenated copper phthalocyanine pigment and a halogenated zinc phthalocyanine pigment.
[5] The colored curable resin composition according to [3] or [4], wherein the green pigment is at least one selected from the group consisting of chlorinated copper phthalocyanine pigments, brominated copper phthalocyanine pigments and brominated zinc phthalocyanine pigments.
[6] The green pigment is C.I. I. Pigment Green 36 and C.I. I. The colored curable resin composition according to any one of [3] to [5], which is at least one selected from the group consisting of Pigment Green 58.
[7] A color filter formed from the colored curable resin composition according to any one of [1] to [6].
[8] A liquid crystal display device including the color filter according to [7].
[9] A compound represented by the formula (IA-1).

Wherein ^(I-A-1), Q 11 and ^{Q 12} independently of one another represent an oxygen atom or a sulfur atom. However, when one of Q ¹¹ and Q ¹² is an oxygen atom, the other is not an oxygen atom.
R ^111A and ^{R 112A,} independently of each other, represent a monovalent hydrocarbon group having a hydrogen atom or a substituent carbon atoms which may have a 1 to 20, -CH ₂ contained in the hydrocarbon group - is , -O-, -CO-, or -N (R ^122A ) ^-may be replaced.
R ^122A represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^{115A _{is, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - L +, -CO 2 H, -CO 2 - L +, -CO 2 R 118A, -SO 3 R 118A or -SO _{It represents 2} N (R ^119A ) (R ^120A ).
L ⁺ represents ⁺ N (R ^11B ) ₄ , Na ⁺ or K ⁺ , and R ^11B may be the same or different.
R ^11B represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^118A represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^119A and R ^120A represent monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and are contained in the saturated aliphatic hydrocarbon groups. CH ₂ − may be replaced by −O−, −CO−, −NH− or −N (R ^118A ) −.
R ^116A and R ^117A represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other.
n1 represents an integer from 0 to 5. When n1 is 2 or more, the plurality of R ^115A may be the same or different.
c represents an integer from 0 to 5.
G ⁻ represents a counterion. ]
[10] A compound represented by the formula (IA).

[In the formula (IA), R ^1A and R ^2A represent a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent independently of each other, and the hydrocarbon group may be used. The included −CH ₂₋ may be replaced by −O−, −CO−, or −N (R ^12A ) −. However, when one of R ^1A and R ^2A is a hydrogen atom, the other is not a hydrogen atom.
R ^12A represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^{5A _{is, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - J +, -CO 2 H, -CO 2 - J +, -CO 2 R 8A, -SO 3 R 8A or -SO Represents ₂ N (R ^9A ) (R ^10A ).
J ⁺ represents ⁺ N (R ^11A ) ₄ , Na ⁺ or K ⁺ , and R ^11A may be the same or different.
R ^11A represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^8A represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^9A and R ^10A represent monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and are contained in the saturated aliphatic hydrocarbon groups. CH ₂ − may be replaced by −O−, −CO−, −NH− or −N (R ^8A ) −.
R ^6A and R ^7A independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
n represents an integer from 0 to 5. When n is 2 or more, the plurality of R ^5A may be the same or different.
b represents an integer from 0 to 5.
Y ⁻ represents a counterion. ]
[11] The compound according to [9] or [10], wherein at least one selected from R ^1A and R ^2A is a monovalent hydrocarbon group having 1 to 20 carbon atoms and having a group containing a silicon atom.
[12] The compound according to [11], wherein the group containing a silicon atom is a group represented by the formula (Z1).

[In the formula (Z1), R ^21A represents a single bond or an alkanediyl group having 1 to 10 carbon atoms, and -CH ₂ − contained in the alkanediyl group is -O-, -CO-, -N ( R ¹² )-, -OCO-, -COO-, -OCONH-, -CONH- or -NHCO- may be substituted, and the hydrogen atom contained in the alkanediyl group is an alkyl having 1 to 4 carbon atoms. It may be substituted with an alkyl group having 1 to 4 carbon atoms containing a group or a hydroxyl group.
R ¹² represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^22A , R ^23A and R ^24A independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. ]

The color filter formed from the colored hard-sticking resin composition of the present invention has good heat resistance.

The color curable resin composition of the present invention contains a colorant (A), a resin (B), and a compound represented by the formula (IA) (hereinafter, may be referred to as a compound (IA)). It contains a polymerizable compound (C) and a polymerization initiator (D).
The colorant (A) may further contain at least one selected from the group consisting of dyes (A2) and pigments (P) other than the compound (IA).
The colored curable resin composition of the present invention may contain a solvent (E) and a leveling agent (F).

<Compound represented by formula (IA)>

Wherein (I-A), ^{Q 1} and ^{Q 2} each independently represent an oxygen atom or a sulfur atom.
R ^1C and R ^2C each represent a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and −CH ₂ − contained in the hydrocarbon group is , -O-, -CO-, or -N (R ^112C ) ^-may be replaced.
R ^112C represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^{5C _{are, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - T +, -CO 2 H, -CO 2 - T +, -CO 2 R 8C, -SO 3 R 8C or -SO Represents ₂ N (R ^9C ) (R ^10C ).
T ⁺ represents ⁺ N (R ^11C ) ₄ , Na ⁺ or K ⁺ , and R ^11C may be the same or different.
R ^11C represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^8C represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^9C and R ^10C represent monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and are contained in the saturated aliphatic hydrocarbon groups. CH ₂ − may be replaced by −O−, −CO−, −NH− or −N (R ^8C ) −.
R ^6C and R ^7C represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other.
m1 represents an integer from 0 to 5. When m1 is 2 or more, the plurality of R ^5Cs may be the same or different.
d represents an integer from 0 to 5.
P ⁻ represents a counterion. ]

Examples of the counterion represented by P ⁻ include a halide ion and a counterion represented by the formula (y1) and the formula (y2).
Examples of the halide ion include fluoride ion, chloride ion, bromide ion and iodide ion.

[In the formula ^{(y1), R B1} represents a fluorinated alkyl group having 1 to 12 carbon atoms.
In formula (y2), R ^B2 and R ^B3 independently represent a halogen atom or an alkyl fluoride group having 1 to 12 carbon atoms. ]

The fluorinated alkyl group having 1 to 12 carbon atoms represented by R ^B1, specifically, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 1,1,2,2,2-pentafluoroethyl Group, 2,2,2-trifluoroethyl group, 3- (trifluoromethyl) -3,4,5,4-pentafluorobutyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, Perfluorosec-butyl group, perfluorotert-butyl group, perfluoropentyl group and perfluorohexyl group can be mentioned, preferably a group in which all hydrogen atoms are substituted with fluorine atoms, and more preferably -CF ₃ , -CF ₂ CF ₃ , -CF ₂ CF ₂ CF ₃ , -CF (CF ₃ ) ₂ , -CF ₂ CF ₂ CF ₂ CF ₃ , -CF ₂ CF (CF ₃ ) ₂ , -C (CF ₃ ) ₃ can be mentioned.

Examples of the halogen atom represented by ^RB2 and ^RB3 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferable.
The fluorinated alkyl group having 1 to 12 carbon atoms represented by R ^B2 and ^{R B3,} the same thing can be mentioned a fluorinated alkyl group represented by ^{R B1,} preferably _{-CF 3, -CF} 2 CF 3 , -CF ₂ CF ₂ CF ₃ , -CF (CF ₃ ) ₂ , -CF ₂ CF ₂ CF ₂ CF ₃ , -CF ₂ CF (CF ₃ ) ₂ , -C (CF ₃ ) ₃ .
R ^B2 and R ^B3 may be combined with each other to form a ring containing −SO ₂ −N ⁻ −SO ₂₋ .

Alkyl groups having 1 to 6 carbon atoms represented by R ^6C and R ^7C include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group and n-pentyl. Linear or branched alkyl groups such as groups, isopentyl groups, neopentyl groups, n-hexyl groups and 2-ethylhexyl groups; cyclic alkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group can be mentioned.
It is preferable that R ^6C and R ^7C are the same.
R ^6C and R ^7C are independent of each other, preferably a linear or branched alkyl group having 1 to 4 carbon atoms, or a hydrogen atom, and more preferably a hydrogen atom.

Examples of the aralkyl group having 7 to 10 carbon atoms represented by R ^11C include a benzyl group, a phenylethyl group, a phenylbutyl group and the like.
The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^11C includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group and a tert-butyl group. , N-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-dodecyl group, n-hexadecyl group, n-icosyl group, etc. Alkyl groups can be mentioned.

The ⁺ N ^(R _{11C) 4} represented by T ^+, _NH ^{4 +,} the following may be mentioned.

Saturated hydrocarbon groups having 1 to 20 carbon atoms represented by R ^8C include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group and dodecyl group. Linear alkyl groups such as groups, hexadecyl groups and icosyl groups; branched chain alkyl groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group and 2-ethylhexyl group; cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclo Examples thereof include an alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms such as a heptyl group, a cyclooctyl group and a tricyclodecyl group.
The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^8C may have a substituent, and the substituent may be a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; Examples thereof include aromatic hydrocarbon groups having 6 to 10 carbon atoms such as a phenyl group and a naphthyl group.
R ^8C is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group.

The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^9C includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group and a decyl group. Examples thereof include an alkyl group having 1 to 20 carbon atoms such as a group, a dodecyl group, a hexadecyl group and an icosyl group.
The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^9C may have a substituent, and the substitution includes halogens such as fluorine atom, chlorine atom, bromine atom and iodine atom. Atoms and hydroxy groups can be mentioned.

The −OR ^8C has 1 to 20 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group and an icosyloxy group. Alkoxy groups can be mentioned.

The -CO ₂ R ^8C, a methoxycarbonyl group, an ethoxycarbonyl group, propoxycarbonyl group, tert- butoxycarbonyl group, an alkoxycarbonyl group having 1 to 20 carbon atoms such as hexyl oxycarbonyl group and icosyl oxycarbonyl group ..

Examples of the −SR ^8C include alkylsulfanyl groups having 1 to 20 carbon atoms such as a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group and an icosylsulfanyl group.
Examples of −SO ₂ R ^8C include alkylsulfonyl groups having 1 to 20 carbon atoms such as a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group and an icosylsulfonyl group.
Examples of −SO ₃ R ^8C include alkoxysulfonyl groups having 1 to 20 carbon atoms such as methoxysulfonyl group, ethoxysulfonyl group, propoxysulfonyl group, tert-butoxysulfonyl group, hexyloxysulfonyl group and icosyloxysulfonyl group. ..

-SO ₂ NR ^9C R ^10C includes, for example, sulfamoyl group;
N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-Butyl sulfamoyl group, N-tert-Butyl sulfamoyl group, N-pentyl sulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-methylbutyl) sulfamoyl group, N- (2-methylbutyl) sulfamoyl group, N- (3) -Methylbutyl) sulfamoyl group, N-cyclopentyl sulfamoyl group, N-hexyl sulfamoyl group, N- (1,3-dimethylbutyl) sulfamoyl group, N- (3,3-dimethylbutyl) sulfamoyl group, N- Heptyl sulfamoyl group, N- (1-methylhexyl) sulfamoyl group, N- (1,4-dimethylpentyl) sulfamoyl group, N-octyl sulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- N-1-substituted sulfamoyl groups such as (1,5-dimethyl) hexyl sulfamoyl group, N- (1,1,2,2-tetramethylbutyl) sulfamoyl group;
N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-propylmethylsulfamoyl group, N, N-isopropylmethylsulfa Moyl group, N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis (1-methylpropyl) sulfamoyl group, N, N-heptylmethylsulfamoyl Examples thereof include N, N-2 substituted sulfamoyl groups such as groups.

The _{^{R 5C, -CO 2 H, -CO}} 2 - T +, -CO 2 R 8, -SO 3 -, -SO 3 - T +, -SO 3 H or _-SO 2 NH ^{(R 9C)} is preferably _{^{, -SO 3 -, -SO 3 -}} T +, more preferably -SO ₃ H or _-SO 2 ^{NHR 9C,} _{-SO 3} ^- is more preferable.


that's all

As m1, an integer of 1 to 4 is preferable, and 1 or 2 is more preferable.
As d, an integer of 1 to 4 is preferable, and 1 or 2 is more preferable.

^Examples of the aralkyl group having 7 to 10 carbon atoms represented by R ^112C include the same aralkyl group having 7 to 10 carbon atoms represented by R ^11C .
Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^112C include the same monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^11C .

The monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R ^1C and R ^2C may be a saturated hydrocarbon group or an unsaturated hydrocarbon group. It may also be an aromatic hydrocarbon group.
Examples of the monovalent saturated hydrocarbon group include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, hexadecyl group and icosyl group. Linear alkyl group with 1 to 20 carbon atoms; branched chain alkyl group with 1 to 20 carbon atoms such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, 2-ethylhexyl group; cyclopropyl group, cyclopentyl group, cyclohexyl Examples thereof include an alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms such as a group, a cycloheptyl group, a cyclooctyl group and a tricyclodecyl group.
Examples of the monovalent unsaturated hydrocarbon group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-1-propenyl group, a 1-butenyl group, a 2-butenyl group, and 3 -An alkenyl group having 2 to 20 carbon atoms of a butenyl group, a 1-pentenyl group and a 1-hexenyl group;
Examples thereof include an alkynyl group having 2 to 20 carbon atoms such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group and a 1-hexynyl group.
As the monovalent aromatic hydrocarbon group, a phenyl group, a toluyl group, a xsilyl group, a mesityl group, a propylphenyl group, a butylphenyl group, a naphthyl group;
Examples thereof include monovalent aromatic hydrocarbon groups having 6 to 20 carbon atoms such as an aralkyl group having 7 to 20 carbon atoms such as a benzyl group and a phenethyl group, and an aromatic hydrocarbon group having 6 to 10 carbon atoms is preferable.

The hydrogen atom contained in the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R ^1C and R ^2C is a group containing a silicon atom, a group containing an acryloyl group, a group containing a methacryloyl group, a halogen atom, and-. _{^{OH, -OR 8C, -SO 3 -}} , -SO 3 H, -SO 3 - T +, -CO 2 H, -CO 2 R 8C, -SR 8C, -SO 2 R 8C, -SO 3 R 8C or It may be replaced with −SO ₂ N (R ^9C ) (R ^10C ).
When R ^1C and R ^2C are monovalent aromatic hydrocarbon groups having 6 to 20 carbon atoms, the substituents of the aromatic hydrocarbon groups include halogen atoms, -R ^8C , -OH, and -OR ^8C . _{^{-SO 3 -, -SO 3 H,}} -SO 3 - T +, -CO 2 H, -CO 2 R 8C, -SR 8C, -SO 2 R 8C, -SO 3 R 8C and _-SO 2 N (R ^{9C) (R 10C)} are _{^{preferred, -SO 3 -, -SO 3 H}} , -SO 3 - T + and _{^{-SO 2 N (R 9C) (}} R 10C) is more preferable, _-SO ³ - ^{Z +} and - SO ₂ N (R ^9C ) (R ^10C ) is even more preferred. In this case, as −SO ₃ ⁻ T ⁺ , −SO ₃ ^{− +} N (R ^11C ) ₄ is preferable.

A group containing a silicon atom means a group containing a silicon atom as a component of the group.
The number of carbon atoms of the group containing a silicon atom is usually 1 to 30, preferably 1 to 20.
As the group containing a silicon atom, a group represented by the formula (Z1) is preferable.

[In the formula, R ^21A represents a single bond or an alkanediyl group having 1 to 10 carbon atoms, and -CH ₂ − contained in the alkanediyl group is -O-, -CO-, -N (R ¹² ). It may be substituted with −, −OCO−, −COO−, −OCONH−, −CONH− or −NHCO−, and the hydrogen atom contained in the alkanediyl group is an alkyl group or a hydroxyl group having 1 to 4 carbon atoms. It may be substituted with an alkyl group having 1 to 4 carbon atoms including.
R ¹² represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^22A , R ^23A and R ^24A independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
* Represents a bond with an oxygen atom. ]

Examples of the arcandyl group having 1 to 10 carbon atoms represented by R ^21A include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, an isopropylene group, an isobutylene group and a 2-methyltri. Examples thereof include the same as the methylene group, the isopentylene group, the isohexylene group, the isooctylene group and the 2-ethylhexylene group. R ^21A is preferably an alkanediyl group having 1 to 6 carbon atoms, and more preferably an alkanediyl group having 1 to 4 carbon atoms.
The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ¹² is the same as the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ¹ , R ² and R ^8. Can be mentioned.

Alkyl groups having 1 to 4 carbon atoms represented by R ^22A , R ^23A and R ^24A include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl. Examples include groups, cyclopropyl groups and cyclobutyl groups.
The alkoxy groups having 1 to 4 carbon atoms represented by R ^22A , R ^23A and R ^24A include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group and a tert-butoxy group. Can be mentioned.
It is preferable that R ^22A , R ^23A and R ^24A are all the same group.
R ^22A , R ^23A and R ^24A are preferably alkyl groups having 1 to 4 carbon atoms or alkoxy groups having 1 to 4 carbon atoms independently of each other.

Examples of the group containing a silicon atom include the following groups.

^Examples of the group in which −CH ₂₋ contained in R ^21A is substituted with −O− include the following groups. * Represents a bond.

Examples of the group in which −CH ₂₋ contained in R ^21A is substituted with −CO− include the following groups. * Represents a bond.

^{Examples of the group} in which −CH ₂ − contained in R ^21A is substituted with −N (R ¹² ) − include the following groups. * Represents a bond.

Examples of the group in which −CH ₂ − contained in R ^21A is substituted with −OCO − include the following groups. * Represents a bond.

Examples of the group in which -CH _2- contained in R ^21A is substituted with -COO- include the following groups. * Represents a bond.

Examples of the group in which -CH _2- contained in R ^21A is substituted with -OCONH- include the following groups. * Represents a bond.

Examples of the group in which −CH ₂ − contained in R ^21A is substituted with −CONH− include the following groups. * Represents a bond.

Examples of the group in which −CH ₂ − contained in R ^21A is substituted with −NHCO− include the following groups. * Represents a bond.

Examples of the group in which the hydrogen atom contained in the alkanediyl group contained in R ^21A may be substituted with an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms containing a hydroxyl group are shown in the table below. The group to be used is mentioned. * Represents a bond.

As the group containing a silicon atom, the groups represented below are preferable.

A group containing an acryloyl group or a group containing a methacryloyl group means a group having at least one acryloyl group or a methacryloyl group as a constituent unit of the group.
The carbon number of the group containing an acryloyl group is usually 3 to 16, preferably 3 to 12, and more preferably 3 to 8.
The carbon number of the group containing a methacryloyl group is usually 4 to 17, preferably 4 to 13, and more preferably 4 to 9.
The group containing an acryloyl group is preferably a group containing an acryloyloxy group.
The group containing a methacryloyl group is preferably a group containing a methacryloyloxy group.
As the group containing an acryloyl group or the group containing a meta-acryloyl group, a group represented by the formula (Z2) is preferable.

Wherein ^{(Z2), R 15A} represents alkanediyl group having 1 to 10 carbon atoms, _-CH 2 contained in the alkanediyl group - is, -O -, - CO -, - N (R 13) It may be substituted with −, −OCO−, −COO−, −OCONH−, −CONH− or −NHCO−, and the hydrogen atom contained in the alkanediyl group is an alkyl group or a hydroxyl group having 1 to 4 carbon atoms. It may be substituted with an alkyl group having 1 to 4 carbon atoms including.
R ¹³ represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^16A represents an acryloyl group or a methacryloyl group.
* Represents a bond with a nitrogen atom. ]

Examples of the alkanediyl group having 1 to 10 carbon atoms represented by R ^15A include the same alkanediyl group having 1 to 10 carbon atoms represented by R ^11A , and the alkanediyl group having 1 to 6 carbon atoms is used. Preferably, an alkanediyl group having 1 to 4 carbon atoms is more preferable.
Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ¹³ include the same monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ¹² .

Examples of the group containing an acryloyl group or a metaacryloyl group include a group represented by the formula (ii-1) to a group represented by the formula (ii-44).

The compound (IA) is preferably a compound represented by the formula (I) and a compound represented by the formula (IA-1).

<Compound represented by formula (I)>

[In the formula (I), R ¹ and R ² represent monovalent hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and the hydrocarbon groups thereof. The included −CH ₂₋ may be replaced by −O−, −CO−, or −N (R ¹² ) −.
R ¹² represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^{5 _{is, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8, -SO 3 R 8 or -SO ₂ Represents N (R ⁹ ) (R ¹⁰ ).
Z ⁺ represents ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and R ¹¹ may be the same or different.
R ¹¹ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ⁹ and R ¹⁰ represent monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and are contained in the saturated aliphatic hydrocarbon group-. CH ₂ - is, -O -, - CO -, - NH- or -N ^{(R 8)} - can have me every conversion at.
R ⁶ and R ⁷ represent hydrogen atoms or alkyl groups having 1 to 6 carbon atoms independently of each other.
m represents an integer from 0 to 5. When m is 2 or more, the plurality of R ^5s may be the same or different.
a represents an integer from 0 to 5.
X ⁻ represents a counterion. ]

Examples of the counterion represented by X ⁻ include the same counterion represented by P ⁻ .
The hydrocarbon group having 1 to 20 carbon atoms which may have a substituent represented by R ¹ and R ² may have a substituent represented by R ^1C and R ^2C. The same as 1 to 20 hydrocarbon groups can be mentioned.
The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^12, include those similar to the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by ^{R 12C.}
Examples of the aralkyl group having 7 to 10 carbon atoms represented by R ¹² include the same aralkyl group having 7 to 10 carbon atoms represented by R ^12C .
The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^11, include those similar to the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by ^{R 11C.}
Examples of the aralkyl group having 7 to 10 carbon atoms represented by R ¹¹ include the same aralkyl group having 7 to 10 carbon atoms represented by R ^11C .
The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^8, include those similar to the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^8C.
The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent represented by R ⁹ and R ¹⁰ has a substituent represented by R ^9C and R ^10C. Examples thereof include the same monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms.
Examples of the alkyl group having 1 to 6 carbon atoms represented by R ⁶ and R ⁷ include the same alkyl group having 1 to 6 carbon atoms represented by R ^6C and R ^7C .
The cation represented by Z ⁺ is the same as the cation represented by T ^{+. The} group represented by R ⁵ is the same as the group represented by R ^5C .

Among the compounds (I), the compound represented by the formula (IA) is preferable.
<Compound represented by formula (IA)>

[In the formula (IA), R ^1A and R ^2A represent a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent independently of each other, and the hydrocarbon group may be used. The included −CH ₂₋ may be replaced by −O−, −CO−, or −N (R ^12A ) −. However, when one of R ^1A and R ^2A is a hydrogen atom, the other is not a hydrogen atom.
R ^12A represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^{5A _{is, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - J +, -CO 2 H, -CO 2 - J +, -CO 2 R 8A, -SO 3 R 8A or -SO Represents ₂ N (R ^9A ) (R ^10A ).
J ⁺ represents ⁺ N (R ^11A ) ₄ , Na ⁺ or K ⁺ , and R ^11A may be the same or different.
R ^11A represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^8A represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^9A and R ^10A represent monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and are contained in the saturated aliphatic hydrocarbon groups. CH ₂ − may be replaced by −O−, −CO−, −NH− or −N (R ^8A ) −.
R ^6A and R ^7A independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
n represents an integer from 0 to 5. When n is 2 or more, the plurality of R ^5A may be the same or different.
b represents an integer from 0 to 5.
Y ⁻ represents a counterion. ]

The monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent represented by R ^1A and R ^2A may have a substituent represented by R ^1C and R ^2C. Examples thereof include the same monovalent hydrocarbon groups having 1 to 20 carbon atoms.
Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^12A include the same monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^12C .
Examples of the aralkyl group having 7 to 10 carbon atoms represented by R ^12A include the same aralkyl group having 7 to 10 carbon atoms represented by R ^12C .

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^11A include the same monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^11C .
Examples of the aralkyl group having 7 to 10 carbon atoms represented by R ^11A include the same aralkyl group having 7 to 10 carbon atoms represented by R ^11C .
Examples of the ⁺ N (R ^11A ) ₄ represented by J ⁺ include the same as the ⁺ N (R ^11C ) ₄ represented by T ⁺ .
^Examples of R ^5A include the same groups represented by R ^5C .

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^8A include the same as the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^8C .
The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent represented by R ^9A and R ^10A has a substituent represented by R ^9C and R ^10C. Examples thereof include the same monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms.
Examples of the alkyl group having 1 to 6 carbon atoms represented by R ^6A and R ^7A include the same alkyl group having 1 to 6 carbon atoms represented by R ^6C and R ^7C .
Examples of the counterion represented by Y ⁻ include the same counterion represented by P ⁻ .

R ^5A is, -SO ₃ ^- is preferably or -SO ₃ H.
R ^6A and R ^7A are preferably linear or branched alkyl groups having 1 to 4 carbon atoms or hydrogen atoms, and more preferably hydrogen atoms, independently of each other.
n is preferably 1 or 2.

<Compound represented by the formula (IA-1)>

Wherein ^(I-A-1), Q 11 and ^{Q 12} independently of one another represent an oxygen atom or a sulfur atom. However, when one of Q ¹¹ and Q ¹² is an oxygen atom, the other is not an oxygen atom.
R ^111A and ^{R 112A,} independently of each other, represent a monovalent hydrocarbon group having a hydrogen atom or a substituent carbon atoms which may have a 1 to 20, -CH ₂ contained in the hydrocarbon group - is , -O-, -CO-, or -N (R ^122A ) ^-may be replaced.
R ^122A represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^{115A _{is, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - L +, -CO 2 H, -CO 2 - L +, -CO 2 R 18A, -SO 3 R 18A or -SO Represents ₂ N (R ^19A ) (R ^20A ).
L ⁺ represents ⁺ N (R ^11B ) ₄ , Na ⁺ or K ⁺ , and the four R ^11Bs may be the same or different.
R ^11B represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^18A represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^19A and R ^20A represent monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and are contained in the saturated aliphatic hydrocarbon groups. CH ₂ − may be replaced by −O−, −CO−, −NH− or −N (R ^18A ) −.
R ^116A and R ^117A represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other.
n1 represents an integer from 0 to 5. When n1 is 2 or more, the plurality of R ^115A may be the same or different.
c represents an integer from 0 to 5.
G ⁻ represents a counterion. ]

The monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent represented by R ^111A and R ^{112A includes a} monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R ^1C and R ^2C. The same as the hydrocarbon of.
Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^122A include the same monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^112C .
^Examples of the aralkyl group having 7 to 10 carbon atoms represented by R ^122A include the same aralkyl group having 7 to 10 carbon atoms represented by R ^112C .
Examples of the ⁺ N (R ^11B ) ₄ represented by L ⁺ include the same as the ⁺ N (R ^11C ) ₄ represented by T ⁺ .
^Examples of R ^115A include the same groups as those represented by R ^5C .

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^118A include the same monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^8C .
Saturated hydrocarbon groups having 1 to 20 carbon atoms which may have substituents represented by R ^119A and R ^120A include carbons which may have substituents represented by R ^9C and R ^10C. The same as the saturated hydrocarbon group of the number 1 to 20 can be mentioned.
^Examples of the alkyl group having 1 to 6 carbon atoms represented by R ^116A and R ^117A include the same alkyl group having 1 to 6 carbon atoms represented by R ^6C and R ^7C .
Examples of the counterion represented by G ⁻ include the same counterion represented by P ⁻ .

It is preferable that Q ¹¹ and Q ¹² are sulfur atoms.
R ^111A and R ^112A independently have an alkyl group having 1 to 6 carbon atoms which may have a substituent or a monovalent aromatic hydrocarbon having 6 to 10 carbon atoms which may have a substituent. It is preferably a hydrogen group.
R ^115A is, -SO ₃ ^- is preferably.
R ^116A and R ^117A are preferably hydrogen atoms or methyl groups independently of each other, and more preferably hydrogen atoms.
As n1, an integer of 1 or 2 is preferable, and 1 is more preferable.
As c, an integer of 0 to 2 is preferable, and 0 or 1 is more preferable.
As G ⁻ , a halide ion and a counter ion represented by the formula (y1) and the formula (y2) are preferable.

Specific examples of the compound (IA) include, for example, a compound represented by the formula (IA-1) to a compound represented by the formula (IA-13) and a compound represented by the formula (IB-1). Compound represented by formula (IB-14), compound represented by formula (IC-1) to compound represented by formula (IC-4), compound represented by formula (ID-1) to compound represented by formula (ID-1) Compound represented by ID-6), compound represented by formula (IE-1) to compound represented by formula (IE-4), compound represented by formula (IF-1) to compound represented by formula (IF-1) 12), the compound represented by the formula (IG-1) to the compound represented by the formula (IG-8), the compound represented by the formula (IH-1) to the compound represented by the formula (IH-7). Examples thereof include a compound represented by the formula (IJ-1) and a compound represented by the formula (IJ-1) to a compound represented by the formula (IJ-10).

The method for producing the compound (IA) will be described. The compound (IA) is, for example, a compound represented by the formula (VI) (hereinafter, may be referred to as “compound (VI)”) and a compound represented by the formula (III) (hereinafter, “compound”). (III) ”) and the compound represented by the formula (III-2) (hereinafter, may be referred to as compound (III-2)) in the presence of an alkali metal carbonate. , Can be obtained by reacting in an organic solvent.

[In formula (III), R ¹ has the same meaning as above, and H has a halogen atom. ]

[In formula (III-2), R ² has the same meaning as above, and Hal ² has a halogen atom. ]

Examples of the halogen atom in the formula (III) and the formula (III-2) include a chlorine atom, a bromine atom, an iodine atom and the like.

Examples of the organic solvent in the reaction of compound (VI), compound (III) and compound (III-2) include amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and 1-methyl-2-pyrrolidone. Can be mentioned.

The reaction temperature in the reaction of compound (VI), compound (III) and compound (III-2) is preferably 0 to 180 ° C, more preferably 20 to 140 ° C. The reaction time is preferably 1 to 48 hours, more preferably 1 to 24 hours.

The amount of compound (III) used is preferably 1 mol or more and 5 mol or less, and more preferably 1 mol or more and 3 mol or less, based on 1 mol of compound (VI).
The amount of compound (III-2) used is preferably 1 mol or more and 5 mol or less, and more preferably 1 mol or more and 3 mol or less, based on 1 mol of compound (VI).

Examples of the alkali metal carbonate used in the reaction of compound (VI), compound (III) and compound (III-2) include lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate.

Further, as another method, for example, the compound (IA) may be referred to as a compound represented by the formula (VI-1) (hereinafter, compound (VI-1). Hal ³ and Hal ⁴ are mutually exclusive. Independently, it represents a halogen atom), a compound represented by the formula (III-3) (hereinafter, may be referred to as a compound (III-3)), and a compound represented by the formula (III-4). Can be obtained by reacting with an organic solvent in the presence of an alkali metal carbonate.

[In formula (III-3), R ^111C has the same meaning as above. ]

[In formula (III-4), R ^112C has the same meaning as above. ]

Examples of the organic solvent in the reaction of the compound (VI-1), the compound (III-3) and the compound (III-4) include N, N-dimethylformamide, N, N-dimethylacetamide and 1-methyl-2-. Amide solvent such as pyrrolidone: Alcohol solvent such as methanol and ethanol can be mentioned.

The reaction temperature in the reaction of compound (VI-1), compound (III-3) and compound (III-4) is preferably 0 to 180 ° C, more preferably 0 to 140 ° C. The reaction time is preferably 0.5 to 48 hours, more preferably 0.5 to 24 hours.

The amount of compound (III-3) used is preferably 1 to 5 mol, more preferably 1 to 3 mol, relative to 1 mol of compound (VI-1).
The amount of compound (III-4) used is preferably 1 to 5 mol, more preferably 1 to 3 mol, relative to 1 mol of compound (VI-1).

Examples of the alkali metal carbonate used in the reaction of compound (VI-1), compound (III-3) and compound (III-4) include lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate.

The method for obtaining the target compound (IA) from the reaction mixture is not particularly limited, and various known methods can be adopted. For example, after the reaction is completed, water is added to precipitate the crystals, and then the crystals are taken out. Recrystallization may be performed if necessary.

Compound (IA) is useful as a dye. Since it has high heat resistance to organic solvents, it is particularly useful as a colorant for a color curable resin composition used for a color filter of a display device such as a liquid crystal display.

The content of the colorant (A) contained in the color-curable resin composition forming the color filter is 0.005% by mass or more and 30% by mass with respect to the total solid content of the color-curable resin composition. It is preferably 0.01% by mass or more and 20% by mass or less. The content of the compound (IA) contained in the color-curable resin composition forming the color filter is 0.025% by mass or more and 48% by mass or less with respect to the total amount of solids. Is more preferable, 0.08% by mass or more and 42% by mass or less is more preferable, and 0.1% by mass or more and 30% by mass or less is further preferable.
Here, the "total amount of solid content" in the present specification means an amount obtained by subtracting the content of the solvent from the total amount of the colored curable resin composition. The total amount of solids and the content of each component relative to the total amount can be measured by a known analytical means such as liquid chromatography or gas chromatography.

<Dye (A2)>
Examples of the dye (A2) include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colorists) and known dyes described in dyeing notes (Color Dyeing Co., Ltd.). According to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acrydin dyes, styryl dyes, coumarin dyes, quinoline. Examples include dyes and nitro dyes. Of these, organic solvent-soluble dyes are preferred.

Specifically, C.I. I. Solvent Yellow 4 (Hereinafter, the description of CI Solvent Yellow is omitted and only the number is described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99. , 162;
C. I. Solvent Orange 2, 7, 11, 15, 26, 56; etc. I. Solvent dye,
C. I. 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;
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; etc. I. Acid dye,
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;
C. I. Direct Orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; etc. I. Direct dye,
C. I. Modant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; etc. C .. I. Examples include modern dyes.

As the dye (A2), yellow dyes such as coumarin dye, gold-containing azo dye, pyridone azo dye, barbitur azo dye, quinophthalone dye, methine dye, and cyanine dye are preferable.

The content of the dye (A2) of the present invention is usually 3 to 99.9% by mass, preferably 4 to 50% by mass, and more preferably 5 to 30% by mass with respect to the total amount of the colorant. is there. When the content of the dye (A2) is within the above range, the brightness of the color filter is high, which is preferable.

<Pigment (P)>
As the pigment (P), a known pigment can be used without particular limitation, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists).
For example, C.I. I. Pigment Yellow 1,3,12,13,14,15,16,17,20,24,31,53,83,86,93,94,109,110,117,125,128,137,138,139, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 194, 214;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
C. I. Examples include green pigments such as Pigment Green 7, 36 and 58.

As the pigment (P), a yellow pigment and a green pigment are preferable, and C.I. I. Pigment Yellow 138, 150, 185 and C.I. I. Pigment Greens 36 and 58 are more preferred. By including the above pigment, the transmission spectrum can be easily optimized, and the heat resistance and chemical resistance of the color filter are improved.

<Resin (B)>
The resin (B) is preferably an alkali-soluble resin (B). The alkali-soluble resin (B) (hereinafter sometimes referred to as "resin (B)") is derived from at least one monomer (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides. It is a copolymer containing a structural unit.
Examples of such a resin (B) include the following resins [K1] to [K6].
Resin [K1] At least one monomer (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as “(a)”) and 2 to 4 carbon atoms. A copolymer with a monomer (b) having a cyclic ether structure and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)");
Resins [K2] (a) and (b) and monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter referred to as "(c)" Copolymer with);
Copolymer of resin [K3] (a) and (c);
Resin [K4] A resin obtained by reacting (b) with a copolymer of (a) and (c);
Resin [K5] A resin obtained by reacting (a) with a copolymer of (b) and (c);
Resin [K6] A resin obtained by reacting a copolymer of (b) and (c) with (a) and further reacting with a carboxylic acid anhydride.

Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexendicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo Bicyclounsaturated compounds containing a carboxy group such as [2.2.1] hept-2-ene and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Unsaturated dicarboxylic acid anhydrides such as tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride;
Unsaturated mono [(meth) acryloyloxyalkyl] esters of divalent or higher valent carboxylic acids such as monosuccinate [2- (meth) acryloyloxyethyl] and mono [2- (meth) acryloyloxyethyl] phthalates. Kind;
Examples thereof include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α- (hydroxymethyl) acrylic acid.
Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an alkaline aqueous solution.

(B) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxylan ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. Say.
In (b), a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group is preferable.
In addition, in this specification, "(meth) acrylic acid" represents at least one kind selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth) acryloyl" and "(meth) acrylate" have the same meaning.

As (b), for example, it has a monomer having an oxylanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and an ethylenically unsaturated bond, and a tetrahydrofuryl group and an ethylenically unsaturated bond. Examples include monomers.

As (b), a monomer having an oxylanyl group and an ethylenically unsaturated bond is preferable in that the reliability of the obtained color filter such as heat resistance and chemical resistance can be further improved. ..

Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth). Acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2.6 ] Decane-8-yl (meth) acrylate (In the art, it is commonly referred to as "dicyclopentanyl (meth) acrylate", and in the case of "tricyclodecyl (meth) acrylate". is.), tricyclo [5.2.1.0 ^2.6] (in meth) acrylate (the art, "dicyclopentenyl (meth acrylate as trivial name)" decene-8-yl are said. ), Dicyclopentanyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl (Meta) acrylic acid esters such as (meth) acrylate;
Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid;
Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5,6-dihydroxybicyclo [2.2] .1] Hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] Hept-2-ene, 5,6-di (2'-hydroxyethyl) bicyclo [2.2. 1] Hept-2-ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy -5-Methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2] .2.1] Hept-2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept-2-ene, 5-Phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5,6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept-2-ene, 5,6-bis (cyclohexyl) Bicyclounsaturated compounds such as oxycarbonyl) bicyclo [2.2.1] hept-2-ene;
N-Phenylmaleimide, N-Cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate, N- (9-acridinyl) maleimide;
Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene , Isoprene, 2,3-dimethyl-1,3-butadiene and the like.
Among these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, benzyl (meth) acrylate, tricyclo [5.2.1.0 ^2.6] decan-8-yl (meth) acrylate, N -Phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene are preferred.

The resin (B), specifically, 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymers, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] Resins such as decyl (meth) acrylate / (meth) acrylic acid copolymer [K1]; glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymers, 3,4-epoxytricyclo [5.2.1.0 ^2.6] decyl (meth) acrylate / (meth) acrylic acid / N- cyclohexyl maleimide copolymer, 3 , 4-epoxytricyclo [5.2.1.0 ^2.6] decyl (meth) acrylate / (meth) acrylic acid / vinyl toluene copolymer, 3-methyl-3- (meth) acryloyl oxymethyl-oxetane / Resin such as (meth) acrylic acid / styrene copolymer [K2]; benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer, benzyl (meth) acrylate / Resins such as tricyclodecyl (meth) acrylate / (meth) acrylic acid copolymer, etc. [K3]; Resins obtained by adding glycidyl (meth) acrylate to benzyl (meth) acrylate / (meth) acrylic acid copolymer, etc. A resin obtained by adding glycidyl (meth) acrylate to a tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, both tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid Resin such as resin to which glycidyl (meth) acrylate is added to the polymer [K4]; resin obtained by reacting (meth) acrylic acid with a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate, tri Resin [K5] such as a resin obtained by reacting a copolymer of cyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate with (meth) acrylic acid; tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate Examples thereof include a resin [K6] such as a resin obtained by reacting a copolymer with (meth) acrylic acid and further reacting with tetrahydrophthalic acid anhydride.

The resin [K1] is, for example, a method described in the document "Design of Experiments for Polymer Synthesis" (written by Takayuki Otsu, Kagaku-Dojin Co., Ltd., 1st edition, 1st edition, published on March 1, 1972) and the document. It can be manufactured with reference to the cited references described in.

The resin (B) is preferably one selected from the group consisting of resin [K1], resin [K2] and resin [K3], and more preferably from the group consisting of resin [K2] and resin [K3]. It is the kind of choice. With these resins, the colored curable resin composition is excellent in developability. The resin [K2] is more preferable from the viewpoint of adhesion between the colored pattern and the substrate.

The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. .. When the molecular weight is in the above range, the hardness of the coating film is improved, the residual film ratio is high, the solubility of the unexposed portion in the developing solution is good, and the resolution of the coloring pattern tends to be improved.
The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.

The acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and even more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titrating with an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 17 to 65% by mass with respect to the total solid content of the color curable resin composition. It is 55% by mass. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film ratio of the colored pattern tend to be improved.

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, which is preferable. Is a (meth) acrylic acid ester compound.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. Etc., and the above-mentioned (a), (b) and (c) can be mentioned.

Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol di. Examples thereof include (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropantri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (dipentaerythritol hexa (). Meta) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl ) Isocyanurate, ethylene glycol-modified pentaerythritol tetra (meth) acrylate, ethylene glycol-modified dipentaerythritol hexa (meth) acrylate, propylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, Examples thereof include caprolactone-modified pentaerythritol tetra (meth) acrylate and caprolactone-modified dipentaerythritol hexa (meth) acrylate. Among them, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate are preferable.

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 to 1,500 or less.

The content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and 17 by mass, based on the total solid content of the colored curable resin composition. It is more preferably ~ 55% by mass.
The content ratio of the resin (B) to the polymerizable compound (C) [resin (B): polymerizable compound (C)] is based on mass, preferably 20:80 to 80:20, more preferably. Is 35: 65-80: 20.
When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming the coloring pattern and the chemical resistance of the color filter tend to be improved.

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids and the like by the action of light and heat, and a known polymerization initiator can be used.
Examples of the polymerization initiator (D) include an O-acyloxime compound, an alkylphenone compound, a biimidazole compound, a triazine compound, and an acylphosphine oxide compound.

Examples of the O-acyloxym compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-. 1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- [9-ethyl-6- (9-ethyl-6- ( 2-Methylbenzoyl) -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,4) −Dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole- 3-Il] -3-cyclopentylpropane-1-imine, N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl] -3-cyclopentylpropane-1 -On-2-imine and the like. Commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (above, manufactured by BASF), and N-1919 (manufactured by ADEKA) may be used. Among them, the O-acyloxym compounds are N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1. At least one selected from the group consisting of −on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyloxy is preferable. -1- (4-Phenylsulfanylphenyl) octane-1-one-2-imine is more preferred.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-. 1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butane-1-one, 2-hydroxy-2-methyl-1 -Phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl- Examples thereof include 1- (4-isopropenylphenyl) propan-1-one oligomers, α, α-diethoxyacetophenone, benzyl dimethyl ketal and the like. Commercially available products such as Irgacure (registered trademark) 369, 907, 379 (all manufactured by BASF) may be used.

Examples of the biimidazole compound include 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2,3-dichlorophenyl) -4. , 4'5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372, JP-A-6-75373, etc.), 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-Tetraphenyl biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) biimidazole, 2,2'-bis (2) -Chlorophenyl) -4,4', 5,5'-tetra (dialkoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (trialkoxyphenyl) ) Biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, etc.), the phenyl group at the 4,4', 5,5'-position is substituted with a carboalkoxy group. Examples thereof include imidazole compounds (see, for example, Japanese Patent Application Laid-Open No. 7-10913).

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4-methoxy). Naftyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-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- (fran-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, etc. Can be mentioned.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

Further, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; benzophenone, methyl o-benzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl- Benzoin compounds such as 4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrene quinone, Kinone compounds such as 2-ethylanthraquinone and benzoylquinone; examples thereof include 10-butyl-2-chloroacrydone, benzyl, methyl phenylglycoxylate, titanosen compounds and the like.

The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound, and more preferably. A polymerization initiator containing an O-acyloxime compound.

The content of the polymerization initiator (D) is preferably 0.1 to 40 parts by mass, more preferably 1 to 30 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is a mass part.

The colored curable resin composition of the present invention may further contain a solvent (E), a leveling agent (F), and the like.

<Solvent (E)>
The solvent (E) is not particularly limited, and a solvent usually used in the art can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule and not containing -COO-), ether ester solvent (solvent in the molecule). Solvent containing -COO- and -O-), Ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule, -O-,- CO- and -COO-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide and the like.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, γ-butyrolactone and the like.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether. , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl Examples thereof include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenyletol, methyl anisole and the like.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy. Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl Examples thereof include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate and the like.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone. And so on.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.
Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.

These solvents may be used alone or in combination of two or more.
Among them, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 3-methoxybutyl acetate, 3-. Methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone, N, N-dimethylformamide, N-methylpyrrolidone and the like are preferable, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethylene glycol monobutyl ether and di More preferred are propylene glycol methyl ether acetate, ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol, ethyl 3-ethoxypropionate, and N-methylpyrrolidone.

The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored curable resin composition. In other words, the solid content of the colored curable resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content of the solvent (E) is in the above range, the flatness at the time of coating is good, and the display characteristics tend to be good because the color density is not insufficient when the color filter is formed.

<Leveling agent (F)>
The colored curable resin composition of the present invention may contain a leveling agent (F). Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specifically, Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, TSF4460 (manufactured by Momentive Performance Materials Japan GK) and the like. ..

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Ltd.), Megafuck (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F554. R30, RS-718-K (manufactured by DIC Co., Ltd.), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.).

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include MegaFvck (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Corporation).

When the leveling agent (F) is contained, the content thereof is preferably 0.001% by mass or more and 0.2% by mass or less, and more preferably 0.002, based on the total amount of the colored curable resin composition. It is by mass% or more and 0.1% by mass or less, and more preferably 0.005% by mass or more and 0.07% by mass or less. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Other ingredients>
The color curable resin composition of the present invention is used in the technical fields such as a polymerization initiator, a filler, other polymer compounds, an adhesion accelerator, an antioxidant, a light stabilizer, and a chain transfer agent, if necessary. May contain additives known in.

<Manufacturing method of colored curable resin composition>
The color curable resin composition of the present invention includes, for example, a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E) used as necessary, and the like. It can be prepared by mixing the leveling agent (F) and other components.
When the pigment (P) is contained, the pigment is preferably mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size of the pigment becomes about 0.2 μm or less. .. At this time, if necessary, a pigment dispersant and a part or all of the resin (B) may be blended. The desired color-curable resin composition can be prepared by mixing the remaining components with the pigment dispersion liquid thus obtained so as to have a predetermined concentration.
It is preferable that compound (II) is previously dissolved in a part or all of the solvent (E) to prepare a solution. It is preferable to filter the solution with a filter having a pore size of about 0.01 to 1 μm.
It is preferable to filter the colored curable resin composition after mixing with a filter having a pore size of about 0.01 to 10 μm.

<Manufacturing method of color filter>
Examples of the method for producing a colored pattern from the colored curable resin composition of the present invention include a photolithography method, an inkjet method, a printing method and the like. Of these, the photolithography method is preferable. The photolithography method is a method in which the colored curable resin composition is applied to a substrate and dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the photolithography method, a colored coating film which is a cured product of the coloring composition layer can be formed by not using a photomask at the time of exposure and / or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.
The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose, application and the like. For example, it is 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.1 to 20 μm. Is 0.5 to 6 μm.

The substrate includes a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is silica-coated, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or on the substrate. Acrylic, silver, silver / copper / palladium alloy thin films, etc. are formed on the glass. Another color filter layer, resin layer, transistor, circuit, or the like may be formed on these substrates.

The formation of each color pixel by the photolithography method can be performed by a known or conventional device or condition. For example, it can be produced as follows.
First, a colored curable resin composition is applied onto a substrate and dried by heating and drying (prebaking) and / or under reduced pressure to remove volatile components such as a solvent to obtain a smooth colored composition layer.
Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.
The temperature at the time of heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.
When the vacuum drying is performed, it is preferably performed in a temperature range of 20 to 25 ° C. under a pressure of 50 to 150 Pa.
The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected depending on the film thickness of the target color filter.

The coloring composition layer is then exposed via a photomask to form the desired coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
As the light source used for exposure, a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, light less than 350 nm is cut by using a filter that cuts this wavelength range, and light near 436 nm, 408 nm, and 365 nm is selectively extracted by using a bandpass filter that extracts these wavelength ranges. You may do it. Specific examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp and the like.
At the time of exposure, the entire exposed surface may be uniformly irradiated with parallel light rays, and the photomask and the substrate on which the coloring composition layer is formed can be accurately aligned. Therefore, exposure of a mask aligner, a stepper, or the like can be performed. It is preferable to use the device.

A coloring pattern is formed on the substrate by developing the coloring composition layer after exposure in contact with a developing solution. By development, the unexposed portion of the coloring composition layer is dissolved in a developing solution and removed. As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Further, the developer may contain a surfactant.
The developing method may be any of a paddle method, a dipping method, a spray method and the like. Further, the substrate may be tilted at an arbitrary angle during development. After development, it is preferable to wash with water.

Further, it is preferable to post-bake the obtained coloring pattern. The post-bake temperature is preferably 150 to 250 ° C, more preferably 160 to 235 ° C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

Next, the present invention will be described in more detail with reference to examples. In the examples,% and parts representing the content or the amount used are based on mass unless otherwise specified.

In the following examples, the structure of the compound was confirmed by mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD type).

[Example 1]
Compound (VI) 3.7 parts (manufactured by Tokyo Chemical Industry Co., Ltd.), 2-ethylhexyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) 9.7 parts, potassium carbonate and 11.0 parts as compound (III). The mixture was stirred at 130 ° C. for 8 hours in the presence of 50 parts of N, N-dimethylformamide. After cooling the obtained reaction solution to room temperature, 400 parts of water was added and the mixture was stirred at room temperature for 1 hour, and crystals were precipitated. The precipitated crystals were obtained as a residue of suction filtration and then dried to obtain 6.8 parts of the compound represented by the formula (IA-4).

Identification of the compound represented by the formula (IA-4) (mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 593.3
Exact Mass: 592.3

[Example 2]
Synthesis was carried out in the same manner as in Example 1 except that (2-bromoethyl) trimethylsilane was used instead of 2-ethylhexyl bromide in Example 1 to obtain a compound represented by the formula (IB-3).

Identification of the compound represented by the formula (IB-3) (mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 707.1
Exact Mass: 706.1

[Example 3]
Synthesis was carried out in the same manner as in Example 1 except that methyl 2- (bromomethyl) acrylate was used instead of 2-ethylhexyl bromide in Example 1 to obtain a compound represented by the formula (IC-2).

Identification of the compound represented by the formula (IC-2) (mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 565.1
Exact Mass: 564.1

[Example 4]
In the presence of 200 parts of methanol, 4.1 parts of the compound represented by the formula (VI-d) (manufactured by Tokyo Chemical Industry Co., Ltd.), α-thioglycerol (manufactured by Tokyo Chemical Industry Co., Ltd.) 2.2 parts and carbon dioxide. 3.5 parts of potassium was heated to reflux for 3 hours. The obtained reaction solution was cooled to room temperature, and then methanol was distilled off. To the obtained residue, 100 parts of water was added, and 10 parts of hydrochloric acid was added. The obtained mixture was filtered to obtain 4.9 parts of the compound represented by the formula (IF-12).

Identification of the compound represented by the formula (IF-12) (mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 549.1
Exact Mass: 548.1

[Synthesis of resin]
An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to create a nitrogen atmosphere, 100 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 85 ° C. with stirring. Then, in the flask, 19 parts of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8-ylacrylate and 3,4-epoxytricyclo [5.2. 1.0 ^2,6 ] Mixture of decane-9-ylacrylate (content ratio is 50:50 in molar ratio) (trade name "E-DCPA", manufactured by Daicel Co., Ltd.) 171 parts propylene glycol monomethyl ether acetate 40 parts The solution dissolved in was added dropwise over about 5 hours using a dropping pump. On the other hand, a solution prepared by dissolving 26 parts of the polymerization initiator 2,2'-azobis (2,4-dimethylvaleronitrile) in 120 parts of propylene glycol monomethyl ether acetate was placed in the flask over about 5 hours using another dropping pump. Dropped. After the dropping of the polymerization initiator was completed, the mixture was kept at the same temperature for about 3 hours and then cooled to room temperature to obtain a solution of a copolymer and resin (B-1) having a solid content of 43.5%. The weight average molecular weight of the obtained resin (B-1) was 8000, the molecular weight distribution was 1.98, and the acid value in terms of solid content was 53 mg-KOH / g.

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
Equipment; HLC-8120GPC (manufactured by Tosoh Corporation)
Column; TSK-GELG2000HXL
Column temperature; 40 ° C
Solvent; THF
Flow velocity; 1.0 mL / min
Test solution solid content concentration; 0.001 to 0.01% by mass
Injection volume; 50 μL
Detector; RI
Calibration standard material; TSK STANDARD POLYSTYRENE
F-40, F-4, F-288, A-2500, A-500
(Made by Tosoh Corporation)
The ratio (Mw / Mn) of the polystyrene-equivalent weight average molecular weight and the number average molecular weight obtained above was used as the molecular weight distribution.

[Preparation of Color Curable Resin Composition]
[Example 5]
Colorant (A): C.I. I. Pigment Green 58 (Pigment) 30 copies,
Acrylic pigment dispersant 12 parts,
Resin (B): Resin B1 (solid content equivalent) 9.5 parts, Solvent (E): Propylene glycol monomethyl ether acetate 180 parts were mixed, and a pigment dispersion liquid (3) in which pigments were sufficiently dispersed using a bead mill. ) Was obtained.

Colorant (A): 0.5 part of the compound represented by the formula (IA-4);
Resin (B): Resin B1 (solid content equivalent) 40 parts;
Polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 49 parts;
Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; BASF; O-acyloxime compound) 9.8 copies;
Solvent (E): 670 parts of propylene glycol monomethyl ether acetate;
Leveling agent (F): 0.15 part of polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.); and pigment dispersion (3) were mixed to obtain a color curable resin composition 1. ..

[Example 6]
In Example 5, C.I. I. Pigment Green 58 instead of C.I. I. A color curable resin composition 2 was obtained in the same manner as in Example 5 except that the compound represented by Pigment Green 36 was used.

[Example 7]
In Example 5, the colored curable resin composition is the same as in Example 5, except that the compound represented by the formula (IB-3) is used instead of the compound represented by the formula (IA-4). I got 3.

[Example 8]
In Example 5, the colored curable resin composition is the same as in Example 5, except that the compound represented by the formula (IC-2) is used instead of the compound represented by the formula (IA-4). I got 4.

[Example 9]
In Example 5, the colored curable resin composition 5 is the same as in Example 5, except that the compound represented by the formula (IF-12) is used instead of the compound represented by the formula (IA-4). Got

[Comparative Example 1]
Rhodamine B (manufactured by Tokyo Chemical Industry Co., Ltd.) 4 copies;
Alkali-soluble resin (B): Resin (B-1) (solid content equivalent) 31 parts;
Polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 30 parts;
Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; BASF; O-acyloxime compound) 8.3 copies;
Solvent (E): 50 parts of ethyl lactate;
Solvent (E): 150 parts of dimethylformamide;
Was mixed to obtain a colored curable resin composition 6.

[Pattern formation]
A color curable resin composition 1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning Inc.) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to obtain a composition layer. After cooling, the distance between the glass substrate on which the composition layer was formed and the quartz glass photomask was set to 100 μm, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used in an air atmosphere at 150 mJ / cm ² The light was irradiated at the exposure amount (365 nm standard). As the photomask, a photomask having a 100 μm line and space pattern formed was used. After light irradiation, the coating film is immersed in an aqueous developer containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 23 ° C. for 80 seconds, washed with water, and then in an oven at 220 ° C. After 20 minutes of post-baking, a pattern was obtained.
Instead of the color-curable resin composition 1, the color-curable resin compositions 2 to 5 were used to obtain a pattern in the same manner.
[Heat resistance evaluation]
The coating film of the color-curable resin composition was heated at 230 ° C. for 20 minutes, and the color difference (ΔEab *) before and after heating of the coating film was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). As a result of performing the above heat resistance evaluation for each coating film formed by using the color curable resin compositions 1 to 5, the color difference (ΔEab *) was 3.5, 3.2, 4.6, respectively. It was 4.2 and 4.9.
Further, as a result of similarly performing a heat resistance evaluation on the coating film formed by using the colored curable resin composition 6 obtained in Comparative Example 1, the color difference (ΔEab *) was 80.1. It was found that the heat resistance of the coating film formed from the colored curable resin composition containing the dye of is excellent.

When the color curable resin composition containing the dye of the present invention is used, a coating film having good heat resistance can be obtained, and a color filter can be provided. The color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors.

Claims (8)

A (meth) acrylic acid ester compound containing a colorant containing a compound represented by the formula (IA), a resin, a polymerizable compound, and a polymerization initiator, wherein the polymerizable compound has at least two ethylenically unsaturated bonds. A colored curable resin composition.

Wherein (I-A), ^{Q 1} and ^{Q 2} each independently represent an oxygen atom or a sulfur atom.
R ^1C and R ^2C each independently represent a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and −CH ₂ − contained in the hydrocarbon group is , -O-, -CO-, or -N (R ^112C ) ^-may be replaced (excluding phenyl groups having a carboxyl group).
R ^112C represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^5C represents −SO ₃ ⁻ , −SO ₃ H, −SO ₃ ⁻ T ⁺ , or −SO ₂ NHR ^9C .
T ⁺ represents ⁺ N (R ^11C ) ₄ , Na ⁺ or K ⁺ , and R ^11C may be the same or different.
R ^11C represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ^8C represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^9C represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and −CH ₂ − contained in the saturated aliphatic hydrocarbon group is −O. It may be replaced by −, −CO−, −NH− or −N (R ^8C ) −.
R ^6C and R ^7C represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other.
m1 represents an integer from 0 to 5. When m1 is 2 or more, the plurality of R ^5Cs may be the same or different.
d represents an integer from 0 to 5.
P ⁻ represents a counterion. ] The color curable resin composition according to claim 1, which comprises a colorant, a resin, a polymerizable compound and a polymerization initiator containing a compound represented by the formula (I).

[In the formula (I), R ¹ and R ² represent monovalent hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and the hydrocarbon groups thereof. The included −CH ₂₋ may be replaced by −O−, −CO−, or −N (R ¹² ) − (excluding phenyl groups having a carboxyl group).
R ¹² represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ⁵ _is, ^-SO 3 _- represents a ^{Z +} or ^{_{-SO 2 NH (R 9) -}} , -SO 3 H, -SO 3.
Z ⁺ represents ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and R ¹¹ may be the same or different.
R ¹¹ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ⁹ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and −CH ₂ − contained in the saturated aliphatic hydrocarbon group is −O. -, - CO -, - NH- or -N ^{(R 8)} - can have me every conversion at.
R ⁶ and R ⁷ represent hydrogen atoms or alkyl groups having 1 to 6 carbon atoms independently of each other.
m represents an integer from 0 to 5. When m is 2 or more, the plurality of R ^5s may be the same or different.
a represents an integer from 0 to 5.
X ⁻ represents a counterion. ] The colored curable resin composition according to claim 1 or 2, further comprising a green pigment. The colored curable resin composition according to claim 3, wherein the green pigment is at least one kind of green pigment selected from the group consisting of a halogenated copper phthalocyanine pigment and a halogenated zinc phthalocyanine pigment. The colored curable resin composition according to claim 3 or 4, wherein the green pigment is at least one selected from the group consisting of chlorinated copper phthalocyanine pigments, brominated copper phthalocyanine pigments and brominated zinc phthalocyanine pigments. The green pigment is C.I. I. Pigment Green 36 and C.I. I. The colored curable resin composition according to any one of claims 3 to 5, which is at least one selected from the group consisting of Pigment Green 58. A color filter formed from the colored curable resin composition according to any one of claims 1 to 6. A liquid crystal display device including the color filter according to claim 7.