JP2019206555A - Compound and coloring curable resin composition - Google Patents

Abstract

To provide a compound for a color filter good in heat resistance.SOLUTION: There is provided a compound represented by a formula (I-A). Qand Qrepresent each independently an oxygen atom or a sulfur atom, Rand Rrepresent each independently H or a monovalent hydrocarbon group which may have a substituent and has 1 to 20 carbon atoms, Rrepresents -SOand -SOH, Rand Rare each independently H or an alkyl group having 1 to 6 carbon atoms, m1 represents an integer of 0 to 5, a plurality of Rmay be same or different when m1 is 2 or more, d represents an integer of 0 to 5, and Prepresents a counter ion.SELECTED DRAWING: None

Description

  The present invention relates to a compound and a colored curable resin composition.

  Dyes are used for color display using reflected light or transmitted light in the fields of fiber materials, liquid crystal display devices, ink jets, and the like. 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).

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

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

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

[In Formula (IA), Q ¹ and Q ² each independently represent an oxygen atom or a sulfur atom.
R ^1C and R ^2C each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and —CH ₂ — contained in the hydrocarbon group is , —O—, —CO—, or —N (R ^112C ) — may be substituted.
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 - J +, -CO 2 H, -CO 2 - T +, -CO 2 R 8C, -SO 3 R 8C or -SO _{2 represents} 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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and are contained in the saturated aliphatic hydrocarbon group − CH ₂ — may be replaced by —O—, —CO—, —NH— or —N (R ^8C ) —.
R ^6C and R ^7C each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
m1 represents the integer of 0-5. When m1 is 2 or more, the plurality of R ^5Cs may be the same or different.
d represents an integer of 0 to 5.
P ⁻ represents a counter ion. ]
[2] The colored curable resin composition according to [1], comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator containing the compound represented by formula (I).

[In Formula (I), R ¹ and R ² each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, 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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and is contained in the saturated aliphatic hydrocarbon group— CH ₂ — may be replaced by —O—, —CO—, —NH— or —N (R ⁸ ) —.
R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
m represents an integer of 0 to 5. When m is 2 or more, the plurality of R ⁵ may be the same or different.
a represents an integer of 0 to 5.
X ⁻ represents a counter ion. ]
[3] The colored curable resin composition according to [1] or [2], further including 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 a chlorinated copper phthalocyanine pigment, a brominated copper phthalocyanine pigment, and a brominated zinc phthalocyanine pigment.
[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 CI 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 formula (IA-1).

[In Formula (IA-1), Q ¹¹ and Q ¹² each independently 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 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and —CH ₂ — contained in the hydrocarbon group is , —O—, —CO—, or —N (R ^122A ) — may be substituted.
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 a _{^{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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and are included in the saturated aliphatic hydrocarbon group − CH ₂ — may be replaced by —O—, —CO—, —NH— or —N (R ^118A ) —.
R ^116A and R ^117A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
n1 represents the integer of 0-5. When n1 is 2 or more, the plurality of R ^115A may be the same or different.
c represents an integer of 0 to 5.
G ⁻ represents a counter ion. ]
[10] A compound represented by the formula (IA).

[In Formula (IA), R ^1A and R ^2A each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, 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 _{2 represents} 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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and is included in the saturated aliphatic hydrocarbon group − CH ₂ — may be replaced by —O—, —CO—, —NH— or —N (R ^8A ) —.
R ^6A and R ^7A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
n represents an integer of 0 to 5. When n is 2 or more, the plurality of R ^5A may be the same or different.
b represents an integer of 0 to 5.
Y ⁻ represents a counter ion. ]
[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 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 represents —O—, —CO—, —N ( R ¹² ) —, —OCO—, —COO—, —OCONH—, —CONH— or —NHCO— may be substituted, and the hydrogen atom contained in the alkanediyl group is alkyl having 1 to 4 carbon atoms. It may be substituted with a C 1-4 alkyl group 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 each 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 hardenable resin composition of the present invention has good heat resistance.

The colored curable resin composition of the present invention includes a colorant (A) containing a compound represented by the formula (IA) (hereinafter sometimes referred to as a compound (IA)), a resin (B), 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 a dye (A2) other than the compound (IA) and a pigment (P).
The colored curable resin composition of the present invention may contain a solvent (E) and a leveling agent (F).

<Compound represented by formula (IA)>

[In Formula (IA), Q ¹ and Q ² each independently represent an oxygen atom or a sulfur atom.
R ^1C and R ^2C each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and —CH ₂ — contained in the hydrocarbon group is , —O—, —CO—, or —N (R ^112C ) — may be substituted.
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 - J +, -CO 2 H, -CO 2 - T +, -CO 2 R 8C, -SO 3 R 8C or -SO _{2 represents} 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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and are contained in the saturated aliphatic hydrocarbon group − CH ₂ — may be replaced by —O—, —CO—, —NH— or —N (R ^8C ) —.
R ^6C and R ^7C each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
m1 represents the integer of 0-5. When m1 is 2 or more, the plurality of R ^5Cs may be the same or different.
d represents an integer of 0 to 5.
P ⁻ represents a counter ion. ]

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

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

Specific examples of the fluorinated alkyl group having 1 to 12 carbon atoms represented by R ^B1 include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, 1,1,2,2,2-pentafluoroethyl. Group, 2,2,2-trifluoroethyl group, 3- (trifluoromethyl) -3,4,4,4-pentafluorobutyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, Examples include a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, and a perfluorohexyl group, preferably a group in which all of the 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 C _{2 CF 3, -CF 2 CF (} CF 3) 2, include -C _{(CF 3)} 3.

Examples of the halogen atom represented by R ^B2 and R ^B3 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.
Examples of the fluorinated alkyl group having 1 to 12 carbon atoms represented by R ^B2 and R ^B3 include the same as the 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 combine with each other to form a ring containing —SO ₂ —N ^—— SO ₂ —.

Examples of the alkyl group 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. A linear or branched alkyl group such as a group, isopentyl group, neopentyl group, n-hexyl group and 2-ethylhexyl group; and a cyclic alkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group.
R ^6C and R ^7C are preferably the same.
R ^6C and R ^7C are independently of each other preferably a linear or branched alkyl group having 1 to 4 carbon atoms or a hydrogen atom, 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, and a phenylbutyl group.
Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^11C include 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. An alkyl group is mentioned.

^{Examples of +} N (R ^11C ) ₄ represented by T ⁺ include NH ₄ ⁺ and the following.

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^8C include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and dodecyl. Linear alkyl groups such as hexyl, hexadecyl and icosyl groups; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl and 2-ethylhexyl; cyclopropyl, cyclopentyl, cyclohexyl and cyclo C3-C20 alicyclic saturated hydrocarbon groups, such as a heptyl group, a cyclooctyl group, a tricyclodecyl group, are mentioned.
The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^8C may have a substituent, and examples of the substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; C6-C10 aromatic hydrocarbon groups, such as a phenyl group and a naphthyl group, are mentioned.
R ^8C is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^9C include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group. C1-C20 alkyl groups, such as a group, a dodecyl group, a hexadecyl group, an icosyl group, are mentioned.
The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^9C may have a substituent, such as a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. An atom and a hydroxy group are mentioned.

—OR ^8C includes 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, an icosyloxy group, and the like. An alkoxy group is mentioned.

Examples of —CO ₂ R ^8C include ^C 1-20 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, hexyloxycarbonyl group, and icosyloxycarbonyl group. .

Examples of —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 an alkoxysulfonyl group having 1 to 20 carbon atoms such as a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group. .

—SO ₂ NR ^9C R ^10C includes, for example, a sulfamoyl group;
N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl 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-cyclopentylsulfamoyl group, N-hexylsulfamoyl N- (1,3-dimethylbutyl) sulfamoyl group, N- (3,3-dimethylbutyl) sulfamoyl group, N-heptylsulfamoyl group, N- (1-methylhexyl) sulfamoyl group, N- (1 , 4-Dimethylpentyl) sulfamoyl group, N-octylsulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- (1,5-dimethyl) hexylsulfamoyl group, N- (1,1,2, , 2-tetramethylbutyl) sulfamoyl group and the like N-1 substituted 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 And N, N-2-substituted sulfamoyl groups such as a group.

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

As m1, the integer of 1-4 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 groups 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 as the 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. Moreover, an aromatic hydrocarbon group may be sufficient.
Examples of monovalent saturated hydrocarbon groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, icosyl, etc. A linear alkyl group having 1 to 20 carbon atoms; a branched alkyl group having 1 to 20 carbon atoms such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, 2-ethylhexyl group; cyclopropyl group, cyclopentyl group, cyclohexyl Group, cycloheptyl group, cyclooctyl group, tricyclodecyl group and the like, and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms.
Examples of the monovalent unsaturated hydrocarbon group include a vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3 -Butenyl group, 1-pentenyl group, 1-hexenyl group having 2 to 20 carbon atoms;
Alkynyl groups having 2 to 20 carbon atoms such as ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 1-hexynyl group, and the like.
Examples of the monovalent aromatic hydrocarbon group include a phenyl group, a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, a butylphenyl group, and a naphthyl group;
Examples thereof include monovalent aromatic hydrocarbon groups having 6 to 20 carbon atoms such as aralkyl groups having 7 to 20 carbon atoms such as benzyl group and phenethyl group; aromatic hydrocarbon groups having 6 to 10 carbon atoms are 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,- _{^{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 substituted 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, examples of the substituent for the aromatic hydrocarbon group include a halogen atom, —R ^8C , —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 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 - More preferred is SO ₂ N (R ^9C ) (R ^10C ). In this case, _-SO ³ - ^{T + _{The, -SO 3 - + N (R}} 11C) 4 is preferred.

The group containing a silicon atom means a group containing a silicon atom as a constituent element of the group.
Carbon number of group containing a silicon atom is 1-30 normally, Preferably it is 1-20.
The group containing a silicon atom is preferably a group represented by the formula (Z1).

[Wherein, R ^21A represents a single bond or an alkanediyl group having 1 to 10 carbon atoms, and —CH ₂ — contained in the alkanediyl group represents —O—, —CO—, —N (R ¹² ). -, -OCO-, -COO-, -OCONH-, -CONH- or -NHCO- may be substituted, the hydrogen atom contained in the alkanediyl group is an alkyl group having 1 to 4 carbon atoms or a hydroxyl group May be substituted with an alkyl group having 1 to 4 carbon atoms.
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 each 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 alkanediyl 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 2-methyltriene. Examples are the same as the methylene group, isopentylene group, isohexylene group, isooctylene group and 2-ethylhexylene group. R ^21A is preferably an alkanediyl group having 1 to 6 carbon atoms, 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. Is mentioned.

Examples of the alkyl group having 1 to 4 carbon atoms represented by R ^22A , R ^23A and R ^24A include 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. Group, cyclopropyl group and cyclobutyl group.
Examples of the alkoxy group 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. Is mentioned.
R ^22A , R ^23A and R ^24A are preferably all the same group.
R ^22A , R ^23A and R ^24A are preferably each independently an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

  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 including a hydroxyl group include Group to be used. * Represents a bond.

  As the group containing a silicon atom, the following groups are preferred.

The group containing an acryloyl group or the group containing a methacryloyl group means a group having at least one acryloyl group or methacryloyl group as a structural unit of the group.
Carbon number of group containing an acryloyl group is 3-16 normally, Preferably it is 3-12, More preferably, it is 3-8.
Carbon number of group containing a methacryloyl group is 4-17 normally, Preferably it is 4-13, More preferably, it is 4-9.
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.
The group containing an acryloyl group or the group containing a methacryloyl group is preferably a group represented by the formula (Z2).

[In the formula (Z2), R ^15A represents an alkanediyl group having 1 to 10 carbon atoms, and —CH ₂ — contained in the alkanediyl group represents —O—, —CO—, —N (R ¹³ ). -, -OCO-, -COO-, -OCONH-, -CONH- or -NHCO- may be substituted, the hydrogen atom contained in the alkanediyl group is an alkyl group having 1 to 4 carbon atoms or a hydroxyl group May be substituted with an alkyl group having 1 to 4 carbon atoms.
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 ones as the alkanediyl group having 1 to 10 carbon atoms represented by R ^11A. 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 as the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ¹² .

  Examples of the group containing an acryloyl group or a methacryloyl 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 Formula (I), R ¹ and R ² each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, 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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and is contained in the saturated aliphatic hydrocarbon group— CH ₂ — may be replaced by —O—, —CO—, —NH— or —N (R ⁸ ) —.
R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
m represents an integer of 0 to 5. When m is 2 or more, the plurality of R ⁵ may be the same or different.
a represents an integer of 0 to 5.
X ⁻ represents a counter ion. ]

Examples of the counter ion represented by X ⁻ include the same counter ions represented by P ⁻ .
Examples of the hydrocarbon group R ¹ and carbon atoms which may have a substituent represented by R ² 1~20, R ^1C and R ^2C carbon atoms, which may have a substituent represented by The same thing as the hydrocarbon group of 1-20 is 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 groups 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 groups 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. The same thing as a C1-C20 monovalent | monohydric saturated hydrocarbon group is mentioned.
The alkyl group having 1 to 6 carbon atoms represented by R ⁶ and ^{R 7,} include those similar to the alkyl group having 1 to 6 carbon atoms represented by ^{R 6C} and ^{R 7C.}
Examples of the cation represented by Z ⁺ include the same cation represented by T ^{+. Examples} of the group represented by R ⁵ include the same cation represented by R ^5C .

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

[In Formula (IA), R ^1A and R ^2A each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, 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 _{2 represents} 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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and is included in the saturated aliphatic hydrocarbon group − CH ₂ — may be replaced by —O—, —CO—, —NH— or —N (R ^8A ) —.
R ^6A and R ^7A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
n represents an integer of 0 to 5. When n is 2 or more, the plurality of R ^5A may be the same or different.
b represents an integer of 0 to 5.
Y ⁻ represents a counter ion. ]

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. The same thing as a good C1-C20 monovalent hydrocarbon group is mentioned.
Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^12A include the same as 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 ^12A include the same aralkyl groups 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 as 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 ^11A include the same aralkyl groups having 7 to 10 carbon atoms represented by R ^11C .
^{Examples of +} N (R ^11A ) ₄ represented by J ⁺ include the same as ⁺ N (R ^11C ) ₄ represented by T ⁺ .
^Examples of R ^5A 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 ^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. The same thing as a C1-C20 monovalent | monohydric saturated hydrocarbon group is mentioned.
The alkyl group having 1 to 6 carbon atoms represented by R ^6A and ^{R 7A,} include those similar to the alkyl group having 1 to 6 carbon atoms represented by ^{R 6C} and ^{R 7C.}
Examples of the counter ion represented by Y ⁻ include the same counter ions represented by P ⁻ .

R ^5A is preferably —SO ₃ ^— or —SO ₃ H.
R ^6A and R ^7A are each independently preferably a linear or branched alkyl group having 1 to 4 carbon atoms, or a hydrogen atom, and more preferably a hydrogen atom.
n is preferably 1 or 2.

<Compound represented by formula (IA-1)>

[In Formula (IA-1), Q ¹¹ and Q ¹² each independently 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 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and —CH ₂ — contained in the hydrocarbon group is , —O—, —CO—, or —N (R ^122A ) — may be substituted.
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. _{2 represents} 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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and are included in the saturated aliphatic hydrocarbon group − CH ₂ — may be replaced by —O—, —CO—, —NH— or —N (R ^18A ) —.
R ^116A and R ^117A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
n1 represents the integer of 0-5. When n1 is 2 or more, the plurality of R ^115A may be the same or different.
c represents an integer of 0 to 5.
G ⁻ represents a counter ion. ]

The monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent represented by R ^111A and R ^112A is a monovalent hydrocarbon having 1 to 20 carbon atoms represented by R ^1C and R ^2C. The same thing as the hydrocarbon of this is mentioned.
Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^122A include the same as the 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 groups having 7 to 10 carbon atoms represented by R ^112C .
^{Examples of +} N (R ^11B ) ₄ represented by L ⁺ include the same as ⁺ 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 as the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^8C .
Examples of the saturated hydrocarbon group R ^119A and ^R carbon atoms which may have a substituent represented by ^120A 1 to ^20, which may have a substituent represented by ^{R 9C} and ^{R 10C} carbon The same thing as the saturated hydrocarbon group of number 1-20 is mentioned.
The alkyl group having 1 to 6 carbon atoms represented by R ^116A and ^{R 117A,} include those similar to the alkyl group having 1 to 6 carbon atoms represented by ^{R 6C} and ^{R 7C.}
Examples of the counter ion represented by G ⁻ include the same counter ions represented by P ⁻ .

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

  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), 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 formula ( 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 formula (IF- 12), a compound represented by formula (IG-1) to a compound represented by formula (IG-8), a compound represented by formula (IH-1) to formula (IH-7) And a compound represented by formula (IJ-10) to a compound represented by formula (IJ-10).

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

[In Formula (III), R ¹ represents the same meaning as described above, and Hal represents a halogen atom. ]

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

  As a halogen atom in Formula (III) and Formula (III-2), a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned.

  Examples of the organic solvent in the reaction of the compound (VI), the compound (III) and the compound (III-2) include amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and 1-methyl-2-pyrrolidone. Is 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, and more preferably 1 to 24 hours.

The amount of compound (III) to be used is preferably 1 mol or more and 5 mol or less, more preferably 1 mol or more and 3 mol or less, relative to 1 mol of compound (VI).
The amount of compound (III-2) to be used is preferably 1 to 5 mol, more preferably 1 to 3 mol, per 1 mol of compound (VI).

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

As another method, for example, compound (IA) may be referred to as a compound represented by formula (VI-1) (hereinafter referred to as compound (VI-1). Hal ³ and Hal ⁴ are Independently represents a halogen atom), a compound represented by the formula (III-3) (hereinafter sometimes referred to as the compound (III-3)), and a compound represented by the formula (III-4) In an organic solvent in the presence of an alkali metal carbonate.

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

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

  As the organic solvent in the reaction of the compound (VI-1), the compound (III-3) and the compound (III-4), N, N-dimethylformamide, N, N-dimethylacetamide and 1-methyl-2- Amide solvents such as pyrrolidone: alcohol solvents such as methanol and ethanol.

  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, and more preferably 0.5 to 24 hours.

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

  Examples of the alkali metal carbonate used in the reaction of the compound (VI-1), the compound (III-3) and the 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 techniques can be employed. For example, after completion | finish of reaction, after adding water and precipitating a crystal | crystallization, the method of taking out a crystal | crystallization is mentioned. Recrystallization may be performed as 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 colored curable resin compositions used for color filters of display devices such as liquid crystal displays.

The content of the colorant (A) contained in the colored 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 colored curable resin composition. Or less, more preferably 0.01% by mass or more and 20% by mass or less. Moreover, the content rate of the compound (IA) contained in the colored curable resin composition which forms this color filter shall be 0.025 mass% or more and 48 mass% or less with respect to the total amount of solid content. Is preferable, 0.08 mass% or more and 42 mass% or less is more preferable, and 0.1 mass% or more and 30 mass% or less is more preferable.
Here, the “total amount of solid content” in this specification refers to an amount obtained by removing 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 thereto can be measured by known analytical means such as liquid chromatography or gas chromatography, for example.

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

Specifically, C.I. I. Solvent Yellow 4 (hereinafter, 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; I. Solvent dyes,
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; I. Acid dyes,
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; I. Direct dyes, C.I. I. Modern yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; etc. . I. Examples include modern dyes.

  The dye (A2) is preferably a yellow dye such as a coumarin dye, a metal-containing azo dye, a pyridone azo dye, a barbiturazo dye, a quinophthalone dye, a methine dye, or a cyanine dye.

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

<Pigment (P)>
The pigment (P) is not particularly limited, and a known pigment can be used. Examples thereof include pigments classified as pigments according to a 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. Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
C. I. And green pigments such as CI Pigment Green 7, 36, and 58.

  The pigment (P) is preferably a yellow pigment or a green pigment. I. Pigment yellow 138, 150, 185 and C.I. I. Pigment Green 36 and 58 are more preferable. By including the pigment, it is easy to optimize the transmission spectrum, 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 an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride. A copolymer containing structural units.
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 acid and unsaturated carboxylic acid anhydride (hereinafter sometimes referred to as “(a)”), and having 2 to 4 carbon atoms A copolymer of a monomer (b) having a cyclic ether structure and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”);
Resin [K2] (a) and (b), monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter referred to as “(c)”) In some cases)
Resin [K3] Copolymer of (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) with a copolymer of (b) and (c) and further reacting with a carboxylic acid anhydride.

As (a), specifically, 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-cyclohexene dicarboxylic 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, 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 polyvalent carboxylic acids such as succinic acid mono [2- (meth) acryloyloxyethyl] and phthalic acid mono [2- (meth) acryloyloxyethyl] 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 the solubility of the resulting resin in an alkaline aqueous solution.

(B) is, for example, a polymerizable compound having a C2-C4 cyclic ether structure (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. Say.
(B) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
In the present specification, “(meth) acrylic acid” represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as “(meth) acryloyl” and “(meth) acrylate” have the same meaning.

  Examples of (b) include a monomer having an oxiranyl 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. And monomers.

  (B) is preferably a monomer having an oxiranyl group and an ethylenically unsaturated bond in that the reliability of the obtained color filter such as heat resistance and chemical resistance can be further increased. .

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 ] Decan-8-yl (meth) acrylate (in the art, it is said to be “dicyclopentanyl (meth) acrylate” as a common name. In the case of “tricyclodecyl (meth) acrylate”) ) Rishikuro (in the art, it is said that "dicyclopentenyl (meth) acrylate" as trivial name.) [5.2.1.0 ^2.6] decene-8-yl (meth) acrylate, dicyclopenta Nyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl (meth) acrylate, etc. (Meth) acrylic acid esters of
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, diethyl itaconate;
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 (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene, etc. Bicyclounsaturated compounds;
N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate, N- (9-acridinyl) maleimide;
Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyl toluene, 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, styrene, vinyltoluene, benzyl (meth) acrylate, tricyclo [5.2.1.0 ^2.6 ] decan-8-yl (meth) acrylate, N from the viewpoint of copolymerization reactivity and heat resistance. -Phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene are preferred.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2.6. ] Resin 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 copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3 , 4-epoxytricyclo [5.2.1.0 ^2.6] decyl (meth) acrylate / (meth) acrylic acid / vinyl toluene copolymer, 3- menu Resins such as ru-3- (meth) acryloyloxymethyloxetane / (meth) acrylic acid / styrene copolymer [K2]; benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) Acrylic acid copolymer, resin such as benzyl (meth) acrylate / tricyclodecyl (meth) acrylate / (meth) acrylic acid copolymer [K3]; benzyl (meth) acrylate / (meth) acrylic acid copolymer A resin in which glycidyl (meth) acrylate is added to a resin, a resin in which glycidyl (meth) acrylate is added to a tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, tricyclodecyl (meth) acrylate / Benzyl (meth) acrylate / (meth) acrylic acid copolymer with glycidyl (meth) acrylate Resin [K4] such as a resin to which a relate is added; a resin obtained by reacting a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate with (meth) acrylic acid, tricyclodecyl (meth) acrylate / Resin such as a resin obtained by reacting a copolymer of styrene / glycidyl (meth) acrylate with (meth) acrylic acid [K5]; a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate (meth) Examples thereof include a resin [K6] such as a resin obtained by further reacting a resin reacted with acrylic acid with a tetrahydrophthalic anhydride.

  The resin [K1] is, for example, a method described in the document “Experimental Method for Polymer Synthesis” (Takayuki Otsu, published by Kagaku Dojin Co., Ltd., First Edition, First Edition, issued March 1, 1972) and the document Can be produced with reference to the cited references described in 1.

The resin (B) is preferably a kind selected from the group consisting of a resin [K1], a resin [K2] and a resin [K3], and more preferably from a group consisting of a resin [K2] and a resin [K3]. It is the kind chosen. When these resins are used, the colored curable resin composition is excellent in developability.
Resin [K2] is more preferable from the viewpoint of adhesion between the coloring 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 further preferably 5,000 to 30,000. . When the molecular weight is in the above range, the coating film hardness is improved, the residual film ratio is high, the solubility of the unexposed area in the developer is good, and the resolution of the colored 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 still more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (B), and can be determined by titration with an aqueous potassium hydroxide solution, for example.

  The content of the resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 65% by mass with respect to the total solid content of the colored curable resin composition. 55% by mass. When the content of the resin (B) is in the above range, a colored pattern can be formed, and the resolution of the colored pattern and the remaining film rate 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 a compound having a polymerizable ethylenically unsaturated bond. Is a (meth) acrylic acid ester compound.

  Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. And the above-mentioned (a), (b) and (c).

  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 (Meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di (meth) acrylate, and the like.

  Especially, it is preferable that a polymeric compound (C) is a polymeric compound which has 3 or more of ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa ( (Meth) 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, caprolactone modified pentaerythritol tetra (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) acrylate, etc. 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, 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, based on the total solid content of the colored curable resin composition, 17 More preferably, it is -55 mass%.
Further, the content ratio of the resin (B) to the polymerizable compound (C) [resin (B): polymerizable compound (C)] is on a mass basis, 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 remaining film ratio at the time of forming the colored 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 capable of generating an active radical, an acid or the like by the action of light or heat and initiating the polymerization, and a known polymerization initiator can be used.
Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

  Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane- 1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1- [9-ethyl-6- ( 2-Methylbenzoyl) -9H-carbazol-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,4) -Dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethane-1-imine, N-acetoxy-1- [9 Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -3-cyclopentylpropane-1-imine, N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl)- 9H-carbazol-3-yl] -3-cyclopentylpropan-1-one-2-imine and the like. Commercial products such as Irgacure (registered trademark) OXE01, OXE02 (above, manufactured by BASF), N-1919 (manufactured by ADEKA) may be used. Among these, O-acyloxime compounds include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, 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-cyclopentylpropan-1-one-2-imine is preferred, and N-benzoyloxy -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, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane- 1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butan-1-one, 2-hydroxy-2-methyl-1 -Phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl- 1- (4-Isopropenylphenyl) propan-1-one oligomer, α, α-diethoxyacetophenone, benzyldimethyl And luketal. Commercial products such as Irgacure (registered trademark) 369, 907, 379 (above, 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 and JP-A-6-75373), 2,2′-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 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 (trialkoxy) Phenyl) biimidazole (for example, see JP-B-48-38403, JP-A-62-174204, etc.), a phenyl group at the 4,4 ′, 5,5′-position is substituted with a carboalkoxy group. Imidazole compounds (see, for example, JP-A-7-10913).

  Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxy Naphthyl) -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- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2) -Methylphenyl) Thenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

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

  Furthermore, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Examples include quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.

  The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds and biimidazole compounds, more preferably It is 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 per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Part by mass.

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

<Solvent (E)>
A solvent (E) is not specifically limited, The solvent normally used in the said field | area can be used. For example, an ester solvent (a solvent containing —COO— in the molecule and not containing —O—), an ether solvent (a solvent containing —O— in the molecule and not containing —COO—), an ether ester solvent (intramolecular) Solvent containing -COO- and -O-), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (containing OH in the molecule, -O-,- A solvent not containing CO- and -COO-), an aromatic hydrocarbon solvent, an amide solvent, dimethyl sulfoxide and the like.

  As ester solvents, methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, 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.

  Ether solvents 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, 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, diethyl Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.

  Examples of ether ester solvents 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 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.

  Examples of 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. Etc.

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, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethylene glycol monobutyl ether, di Propylene glycol methyl ether acetate, ethyl lactate, 3-methoxy Chill acetate, 3-methoxy-1-butanol, ethyl 3-ethoxypropionate, N- methylpyrrolidone is more preferred.

  The content rate of a solvent (E) becomes like this. Preferably it is 70-95 mass% with respect to the total amount of a colored curable resin composition, More preferably, it is 75-92 mass%. 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 when the color filter is formed, the color density does not become insufficient and the display characteristics tend to be good.

<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 surfactants, fluorine surfactants, and silicone surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
Examples of the silicone surfactant include a surfactant having a siloxane bond in the molecule. Specifically, Toray 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 and TSF4460 (made by Momentive Performance Materials Japan GK) .

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

  Examples of the silicone-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation), and the like can be given.

  When the leveling agent (F) is contained, the content is preferably 0.001% by mass or more and 0.2% by mass or less, more preferably 0.002%, based on the total amount of the colored curable resin composition. It is not less than 0.1% by mass and more preferably not more than 0.005% by mass and not more than 0.07% by mass. 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 colored curable resin composition of the present invention includes a polymerization initiation aid, a filler, another polymer compound, an adhesion promoter, an antioxidant, a light stabilizer, a chain transfer agent, and the like as necessary. And may contain known additives.

<Method for producing colored curable resin composition>
The colored 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, It can be prepared by mixing the leveling agent (F) and other components.
The pigment in the case of containing the pigment (P) is preferably mixed in advance with a part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle diameter of the pigment is about 0.2 μm or less. . Under the present circumstances, you may mix | blend a pigment dispersant and some or all of resin (B) as needed.
The desired colored curable resin composition can be prepared by mixing the remaining components in the pigment dispersion thus obtained so as to have a predetermined concentration.
It is preferable to prepare a solution by dissolving compound (II) in part or all of the solvent (E) in advance. The solution is preferably filtered with a filter having a pore size of about 0.01 to 1 μm.
The colored curable resin composition after mixing is preferably filtered with a filter having a pore size of about 0.01 to 10 μm.

<Color filter manufacturing method>
Examples of the method for producing a colored pattern from the colored curable resin composition of the present invention include a photolithographic method, an inkjet method, and a printing method. Of these, the photolithographic method is preferable. The photolithographic method is a method in which the colored curable resin composition is applied to a substrate, dried to form a colored composition layer, and the colored composition layer is exposed through a photomask and developed. In the photolithography method, a colored coating film that is a cured product of the colored composition layer can be formed by not using a photomask and / or not developing during exposure. The colored pattern and the colored coating film thus formed are 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 and application, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably. Is 0.5-6 μm.

  As the substrate, quartz glass, borosilicate glass, alumina silicate glass, glass plate such as soda lime glass coated with silica on the surface, resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, on the substrate In addition, aluminum, silver, or a silver / copper / palladium alloy thin film is used. On these substrates, another color filter layer, a resin layer, a transistor, a circuit, and the like may be formed.

The formation of each color pixel by the photolithography method can be performed by a known or commonly used apparatus and conditions. For example, it can be produced as follows.
First, a colored curable resin composition is applied on a substrate, dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as a solvent, and a smooth colored composition layer is obtained.
Examples of the coating method include spin coating, slit coating, and slit and spin coating.
As temperature in performing heat drying, 30-120 degreeC is preferable and 50-110 degreeC is more preferable. Moreover, as heating time, 10 second-60 minutes are preferable, and 30 second-30 minutes are more preferable.
When performing vacuum drying, it is preferable to carry out in the temperature range of 20-25 degreeC under the pressure of 50-150 Pa.
The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected according to the film thickness of the target color filter.

Next, the coloring composition layer is exposed through a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
The light source used for exposure is preferably a light source that generates light having a wavelength of 250 to 450 nm. For example, light less than 350 nm can be cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Or you may. Specifically, examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp, and a halogen lamp.
At the time of exposure, the entire exposure surface may be irradiated with parallel light rays, and the photomask can be accurately aligned with the substrate on which the colored composition layer is formed, so that exposure such as a mask aligner and a stepper is possible. It is preferred to use an apparatus.

A colored pattern is formed on the substrate by developing the exposed colored composition layer in contact with a developer. By the development, the unexposed portion of the colored composition layer is dissolved in the developer and removed.
As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, 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 paddle method, dipping method, 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.

  Furthermore, it is preferable to post-bake the obtained colored pattern. As post-baking temperature, 150-250 degreeC is preferable and 160-235 degreeC is more preferable. As post-baking time, 1-120 minutes are preferable and 10-60 minutes are more preferable.

  Next, the present invention will be described more specifically with reference to examples. In the examples, “%” and “part” representing the content or 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]
3.7 parts of compound (VI) (manufactured by Tokyo Chemical Industry Co., Ltd.), 9.7 parts of 2-ethylhexyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) as compound (III), 11.0 parts of potassium carbonate 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 liquid to room temperature, 400 parts of water was added and stirred at room temperature for 1 hour, whereby crystals were deposited. The precipitated crystals were obtained as a suction filtration residue and dried to obtain 6.8 parts of a compound represented by the formula (IA-4).

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

[Example 2]
Synthesis was performed 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 compound represented by formula (IB-3) (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ 707.1
Exact Mass: 706.1

[Example 3]
Synthesis was performed 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 compound represented by 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, the compound represented by the formula (VI-d) 4.1 parts (manufactured by Tokyo Chemical Industry Co., Ltd.), α-thioglycerol (manufactured by Tokyo Chemical Industry Co., Ltd.) 2.2 parts and carbonic acid 3.5 parts of potassium was heated to reflux for 3 hours. After cooling the obtained reaction liquid to room temperature, 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 a compound represented by the formula (IF-12).

Identification of compound represented by 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 passed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to make a nitrogen atmosphere, 100 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 85 ° C. with stirring. Next, 19 parts of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan-8-yl acrylate and 3,4-epoxytricyclo [5.2. 1.0 ^2,6 ] decan-9-yl acrylate mixture (content ratio is 50:50 in molar ratio) (trade name “E-DCPA”, manufactured by Daicel Corporation) 171 parts propylene glycol monomethyl ether acetate 40 parts The solution dissolved in was dropped over about 5 hours using a dropping pump. On the other hand, a solution prepared by dissolving 26 parts of polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 120 parts of propylene glycol monomethyl ether acetate was placed in the flask over another 5 hours using another dropping pump. It was dripped. After completion of dropping of the polymerization initiator, the temperature was maintained at the same temperature for about 3 hours, and then cooled to room temperature to obtain a solution of a copolymer and a 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-reduced weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)
Column; TSK-GELG2000HXL
Column temperature: 40 ° C
Solvent: THF
Flow rate: 1.0 mL / min
Test liquid solid content concentration: 0.001 to 0.01% by mass
Injection volume: 50 μL
Detector; RI
Reference material for calibration; TSK STANDARD POLYSTYRENE
F-40, F-4, F-288, A-2500, A-500
(Manufactured by Tosoh Corporation)
The polystyrene-converted weight average molecular weight and number average molecular weight ratio (Mw / Mn) obtained above was defined as molecular weight distribution.

(Preparation of colored curable resin composition)
[Example 5]
Colorant (A): C.I. I. Pigment Green 58 (pigment) 30 parts,
12 parts acrylic pigment dispersant,
Resin (B): Resin B1 (solid content conversion) 9.5 parts and Solvent (E): Propylene glycol monomethyl ether acetate 180 parts were mixed, and a pigment dispersion liquid (3 )

Colorant (A): 0.5 part of a compound represented by formula (IA-4);
Resin (B): Resin B1 (solid content conversion) 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 (registered trademark) OXE-01; manufactured by BASF; O-acyloxime compound) 9.8 parts;
Solvent (E): 670 parts of propylene glycol monomethyl ether acetate;
Leveling agent (F): polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.15 part; and pigment dispersion (3) were mixed to obtain a colored curable resin composition 1. .

[Example 6]
In Example 5, C.I. I. In place of Pigment Green 58, C.I. I. A colored 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, a colored curable resin composition was used in the same manner as in Example 5 except that the compound represented by the formula (IB-3) was used instead of the compound represented by the formula (IA-4). 3 was obtained.

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

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

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

[Formation of pattern]
The colored curable resin composition 1 was applied by spin coating on a 2 inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100 ° C. for 3 minutes to obtain a composition layer. After cooling, the distance between the glass substrate on which the composition layer is formed and the photomask made of quartz glass is set to 100 μm, and using an exposure machine (TME-150RSK; manufactured by Topcon Corporation), 150 mJ / cm ^{2 in} an air atmosphere. Was irradiated with light at an exposure amount (365 nm reference). A photomask having a 100 μm line and space pattern was used. After light irradiation, the coating film was immersed and developed in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23 ° C. for 80 seconds, washed with water, and 220 ° C. in an oven. Was post-baked for 20 minutes to obtain a pattern.
It replaced with the colored curable resin composition 1, and obtained the pattern similarly using the colored curable resin compositions 2-5.
[Heat resistance evaluation]
The coating film of the colored curable resin composition was heated at 230 ° C. for 20 minutes, and the color difference (ΔEab *) before and after the heating of the coating film was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). About each coating film formed using the colored curable resin compositions 1 to 5, as a result of performing the above heat resistance evaluation, the color difference (ΔEab *) was 3.5, 3.2, 4.6, 4.2 and 4.9.
Moreover, as a result of similarly performing heat resistance evaluation about the coating film formed using the colored curable resin composition 6 obtained by the comparative example 1, color difference ((DELTA) Eab *) is 80.1 and this invention It turned out that the heat resistance of the coating film formed from the colored curable resin composition containing this dye is excellent.

  When the colored 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 for display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors.

Claims (4)

A compound represented by formula (IA-1).

[In Formula (IA-1), Q ¹¹ and Q ¹² each independently 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 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and —CH ₂ — contained in the hydrocarbon group is , —O—, —CO—, or —N (R ^122A ) — may be substituted.
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 a _{^{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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and are included in the saturated aliphatic hydrocarbon group − CH ₂ — may be replaced by —O—, —CO—, —NH— or —N (R ^118A ) —.
R ^116A and R ^117A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
n1 represents the integer of 0-5. When n1 is 2 or more, the plurality of R ^115A may be the same or different.
c represents an integer of 0 to 5.
G ⁻ represents a counter ion. ] A compound represented by formula (IA).

[In Formula (IA), R ^1A and R ^2A each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, 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 _{2 represents} 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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and is included in the saturated aliphatic hydrocarbon group − CH ₂ — may be replaced by —O—, —CO—, —NH— or —N (R ^8A ) —.
R ^6A and R ^7A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
n represents an integer of 0 to 5. When n is 2 or more, the plurality of R ^5A may be the same or different.
b represents an integer of 0 to 5.
Y ⁻ represents a counter ion. ] The compound according to claim 1 or 2, wherein at least one selected from R ^1A and R ^2A is a monovalent hydrocarbon group having 1 to 20 carbon atoms having a group containing a silicon atom. The compound according to claim 3, 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 represents —O—, —CO—, —N ( R ¹² ) —, —OCO—, —COO—, —OCONH—, —CONH— or —NHCO— may be substituted, and the hydrogen atom contained in the alkanediyl group is alkyl having 1 to 4 carbon atoms. It may be substituted with a C 1-4 alkyl group 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 each 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. ]