TWI827836B - Colored resin composition, color filter and display device - Google Patents

Abstract

The present invention relates to a colored resin composition, a color filter formed from the above-mentioned colored resin composition, and a display device containing the above-mentioned color filter. The above-mentioned colored resin composition contains a colorant, a resin, a polymerizable compound and a polymerization initiator, The colorant includes a triarylmethane lake and a compound represented by formula (A1). In formula (A1), A ^1a and A ^2a each independently represent a phenylene group that may have a substituent; L ^1a and L ^2a each independently represent Independently represents a divalent hydrocarbon group with 1 to 12 carbon atoms. -CH ₂ - contained in the hydrocarbon group can be replaced by -O-, -SO ₂ - or -NR ^11a -; R ^1a to R ^6a each independently represents A hydrogen atom, a halogen atom or an alkyl group having 1 to 8 carbon atoms; R ^11a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. Compared with conventionally known colored resin compositions, the light resistance and heat resistance of the formed color filter are further improved. In addition, the heat resistance in the state where the outer coating layer is laminated is also improved.

Description

Colored resin composition, color filter and display device

The present invention relates to a colored resin composition, a color filter formed from the colored resin composition, and a display device including the color filter.

In display devices such as liquid crystal displays, electroluminescence displays, and plasma displays, and in solid-state imaging such as CCD (Charge-Coupled Device) or CMOS (Complementary Metal-Oxide-Semiconductor) sensors, The color filter used in the element is made of a colored resin composition. As such a colored resin composition, a composition containing only a triarylmethane compound represented by formula (A3-7) as a colorant is known (Patent Document 1).

Prior technical literature patent documents Patent Document 1: Japanese Patent Application Publication No. 2018-127596

[Problem to be solved by the invention]

The object is to further improve the light resistance and heat resistance of the formed color filter compared with the above-mentioned compositions known conventionally. In addition, a subject is to improve the heat resistance even in a state where an overcoat is laminated. [Methods to solve the problem]

The gist of the present invention is as follows. [1] A colored resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, wherein the colorant contains a triarylmethane lake and a compound represented by formula (A1). [In formula (A1), A ^1a and A ^2a each independently represent a phenylene group which may have a substituent. L ^1a and L ^2a each independently represent a divalent hydrocarbon group having 1 to 12 carbon atoms, and -CH ₂ - contained in the hydrocarbon group may be replaced by -O-, -SO ₂ - or -NR ^11a -. R ^1a to R ^6a each independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 8 carbon atoms. R ^11a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. ] [2] The colored resin composition as described in [1], wherein the triarylmethane lake is at least one selected from the group consisting of a compound represented by formula (A2) and a compound represented by formula (A3) . [In formula (A2), R ^11b to R ^14b each independently represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or may have a substituent. An aralkyl group with 7 to 30 carbon atoms. In the saturated hydrocarbon group with 1 to 20 carbon atoms, the hydrogen atoms contained in the saturated hydrocarbon group may be replaced by substituted or unsubstituted amine groups or halogen atoms. When When the number of carbon atoms of the saturated hydrocarbon group is 2 to 20, -CH ₂ - contained in the saturated hydrocarbon group can be replaced by -O- or -CO-. However, in the saturated hydrocarbon group with 2 to 20 carbon atoms, adjacent -CH ₂ - will not be replaced by -O- at the same time. R ^11b and R ^12b may be bonded to form a ring together with the nitrogen atom to which they are bonded, and R ^13b and R ^14b may be bonded to form a ring together with the nitrogen atom to which they are bonded. R ^17b to R ^24b each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, or an alkyl group having 1 to 8 carbon atoms, and -CH ₂ - constituting the alkyl group may be replaced by -O- or -CO-. R ^18b and R ^22b may be bonded to each other to form -NH-, -O-, -S- or -SO ₂ -. Ring T ^1b represents an aromatic heterocyclic ring having 3 to 10 carbon atoms which may have a substituent or an aromatic hydrocarbon ring having 6 to 10 carbon atoms which may have a substituent. [Y] ^m- represents any m-valent anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen. m represents any natural number. In addition, when one molecule contains a plurality of structures represented by the following formulas, they may be the same or different structures. [In the formula, each of ring T ^1b , R ^11b to R ^14b and R ^17b to R ^24b has the same meaning as above. ]] [In formula (A3), R ^41b to R ^44b each independently represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or a substituted The aromatic hydrocarbon group and the aralkyl group may have an aralkyl group having 7 to 30 carbon atoms. The substituent that the aromatic hydrocarbon group and the aralkyl group may have may be -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . The saturated The hydrogen atoms contained in the hydrocarbon group can be replaced by substituted or unsubstituted amino groups or halogen atoms. When the number of carbon atoms in the saturated hydrocarbon group is 2 to 20, the -CH ₂ - contained in the saturated hydrocarbon group can be replaced by -O -or-CO-displacement. However, in the saturated hydrocarbon group with 2 to 20 carbon atoms, adjacent -CH ₂ - will not be replaced by -O- at the same time. R ^41b and R ^42b may be bonded to form a ring together with the nitrogen atom to which they are bonded, and R ^43b and R ^44b may be bonded to form a ring together with the nitrogen atom to which they are bonded. R ^47b to R ^54b each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, -SO ₃ ^- , -SO ₂ -N ^- -SO ₂ -R ^f , or an alkyl group having 1 to 8 carbon atoms, and constitute -CH ₂ - of the alkyl group may be replaced by -O- or -CO-, and R ^48b and R ^52b may be bonded to each other to form -NH-, -S-, or -SO ₂ -. However, in this alkyl group, adjacent -CH ₂ - will not be replaced by -O- at the same time. Ring T ^2b represents an aromatic heterocyclic ring with 3 to 10 carbon atoms or an aromatic hydrocarbon ring with 6 to 10 carbon atoms. The aromatic heterocyclic ring and the aromatic hydrocarbon ring may have a saturated hydrocarbon group with 1 to 20 carbon atoms. , a substituted or unsubstituted amino group or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. The aromatic hydrocarbon group may have -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f as a substituent. M ^r+ represents a metal ion with r valence. k represents the sum of the number of -SO ₃ ^- and the number of -SO ₂ -N ^- -SO ₂ -R ^f that R ^41b to R ^44b , R ^47b to R ^54b and ring T ^2b have. r represents an integer above 1. R ^f represents a fluoroalkyl group having 1 to 12 carbon atoms. Among them, R ^41b to R ^44b , R ^47b to R ^54b and ring T ^2b have at least one -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . In addition, when one molecule contains a plurality of structures represented by the following formulas, they may be the same or different structures. [In the formula, each of Ring T ^2b , R ^41b to R ^44b and R ^47b to R ^54b has the same meaning as above. ]] [3] A color filter formed from the colored resin composition described in [1] or [2]. [4] A display device including the color filter described in [3]. [Effects of the invention]

The color filter formed from the colored resin composition of the present invention is excellent in light resistance, heat resistance, and heat resistance in a state in which an outer coating layer is laminated.

The colored resin composition of the present invention contains a colorant (hereinafter, sometimes referred to as "colorant (A)"), a resin (hereinafter, sometimes referred to as "resin (B)"), and a polymerizable compound (hereinafter, sometimes referred to as "resin (B)"). (hereinafter, sometimes referred to as "polymerizable compound (C)") and a polymerization initiator (hereinafter, sometimes referred to as "polymerization initiator (D)").

The colored resin composition of the present invention preferably further contains a solvent (hereinafter, may be referred to as solvent (E)).

The colored resin composition of the present invention may contain a leveling agent (hereinafter, may be referred to as a leveling agent (F)).

In this specification, the compounds exemplified as each component can be used alone or in combination of multiple types unless otherwise stated.

＜Coloring agent (A)＞

The colored resin composition of the present invention contains a triarylmethane lake and a specific anthraquinone compound described below as a colorant (A).

＜Triarylmethane Lake＞

The triarylmethane lake of the present invention means that a triarylmethane dye soluble in water and organic solvents is precipitated using a precipitating agent to become an organic pigment insoluble in water and organic solvents.

The triarylmethane lake may be a compound composed of cations having a triarylmethane skeleton and anions derived from a precipitating agent, or may be a compound composed of anions having a triarylmethane skeleton and cations derived from a precipitating agent. The triarylmethane skeleton refers to a skeleton in which three aromatic rings are bonded to one carbon. Among the three aromatic rings, two are preferably aromatic hydrocarbon rings and one is an aromatic heterocyclic ring. Ring skeleton.

The triarylmethane lake is preferably selected from the compound represented by formula (A2) (hereinafter, sometimes referred to as compound (A2)) and the compound represented by formula (A3) (hereinafter, sometimes referred to as compound ( At least one of the groups composed of A3)).

＜＜Compound (A2)＞ [In formula (A2), R ^11b to R ^14b each independently represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or may have a substituent. An aralkyl group with 7 to 30 carbon atoms. In the saturated hydrocarbon group with 1 to 20 carbon atoms, the hydrogen atoms contained in the saturated hydrocarbon group may be replaced by substituted or unsubstituted amine groups or halogen atoms. When When the number of carbon atoms of the saturated hydrocarbon group is 2 to 20, -CH ₂ - contained in the saturated hydrocarbon group can be replaced by -O- or -CO-. However, in the saturated hydrocarbon group with 2 to 20 carbon atoms, adjacent -CH ₂ - will not be replaced by -O- at the same time. R ^11b and R ^12b may be bonded to form a ring together with the nitrogen atom to which they are bonded, and R ^13b and R ^14b may be bonded to form a ring together with the nitrogen atom to which they are bonded. R ^17b to R ^24b each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, or an alkyl group having 1 to 8 carbon atoms, and -CH ₂ - constituting the alkyl group may be replaced by -O- or -CO-. R ^18b and R ^22b may be bonded to each other to form -NH-, -O-, -S- or -SO ₂ -. Ring T ^1b represents an aromatic heterocyclic ring having 3 to 10 carbon atoms which may have a substituent or an aromatic hydrocarbon ring having 6 to 10 carbon atoms which may have a substituent. [Y] ^m- represents any m-valent anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen. m represents any natural number. In addition, when one molecule contains a plurality of structures represented by the following formulas, they may be the same or different structures. [In the formula, each of ring T ^1b , R ^11b to R ^14b and R ^17b to R ^24b has the same meaning as above. ]]

The aromatic heterocyclic ring of ring T ^1b may be a monocyclic ring or a condensed ring.

Examples of substituents that the aromatic heterocyclic ring of ring T ^1b may have include a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms that may have a substituent, and an alkyl group having 6 to 20 carbon atoms that may have a substituent. 20 aromatic hydrocarbon groups, optionally substituted amine groups, etc. Ring T ^1b is preferably an amine group which may have a substituent such as an alkyl group having 1 to 10 carbon atoms.

Among them, the aromatic heterocyclic ring of ring T ^1b is preferably an aromatic heterocyclic ring containing a nitrogen atom, and more preferably a 5-membered aromatic heterocyclic ring containing a nitrogen atom.

Furthermore, the ring T ^1b is particularly preferably a ring represented by formula (A2-t1). [In formula (A2-t1), R ^26b represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group which may have a substituent. X1b represents an oxygen atom, -NR ^27b -, or a sulfur atom. R ^27b represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. R ^15b and R ^16b each independently represent a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and an alkyl group having 2 to 20 carbon atoms, and -CH ₂ - contained in the alkyl group may be -O- The substituted group is an aromatic hydrocarbon group which may have a substituent, an aralkyl group which may have a substituent, or a hydrogen atom. R ^15b and R ^16b may be bonded to form a ring together with the nitrogen atom to which they are bonded. However, the adjacent -CH ₂ - will not be replaced by -O- at the same time. In addition, -CH ₂ - bonded to the nitrogen atom will not be replaced by -O-. * indicates the bonding end with the carbocation. ]

Examples of the aromatic hydrocarbon ring of ring T ^1b include benzene ring, naphthalene ring, and the like.

Examples of substituents that the aromatic hydrocarbon ring of ring T ^1b may have include a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms that may have a substituent, and an alkyl group having 6 to 20 carbon atoms that may have a substituent. 20 aromatic hydrocarbon groups, optionally substituted amine groups, etc.

The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^11b to R ^16b and R ^26b may be linear, branched, or cyclic. Examples of linear or branched saturated hydrocarbon groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl, decyl, dodecyl, hexadecyl, di Linear alkyl groups such as dedecyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl. The saturated hydrocarbon group preferably has 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, and further preferably 1 to 6 carbon atoms.

The cyclic saturated hydrocarbon group represented by R ^11b to R ^16b and R ^26b may be monocyclic or polycyclic. Examples of the cyclic saturated hydrocarbon group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like. The cyclic saturated hydrocarbon group preferably has 3 to 10 carbon atoms, more preferably 6 to 10 carbon atoms.

The saturated hydrocarbon groups of R ^11b to R ^16b and R ^26b may be substituted by a halogen atom or may be substituted by an amino group which may be substituted. Examples of the optionally substituted amino group include an amino group and an alkylamine group such as a methylamino group, a dimethylamino group, and a diethylamine group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like. Furthermore, when the halogen atom is a fluorine atom, it is preferable that the halogen atom is substituted to form a perfluoroalkyl unit such as a trifluoromethyl unit, a pentafluoroethyl unit, or a heptafluoropropyl unit.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R ^17b to R ^24b include those having 1 to 8 carbon atoms among the linear or branched saturated hydrocarbon groups exemplified as the saturated hydrocarbon group represented by R ^11b group.

Examples of the alkyl group having 1 to 10 carbon atoms represented by R ^27b include groups having 1 to 10 carbon atoms among the linear or branched saturated hydrocarbon groups exemplified as the saturated hydrocarbon group represented by R ^11b .

When the number of carbon atoms of the saturated hydrocarbon group (preferably an alkyl group) represented by R ^11b to R ^16b is 2 or more, -CH ₂ - contained in the saturated hydrocarbon group (preferably an alkyl group) may be replaced by -O- or -CO- is replaced, preferably by -O-. The preferred number of carbon atoms of the saturated hydrocarbon group (preferably an alkyl group) is 2 to 10, more preferably 2 to 8. In addition, when -CH ₂ - is replaced by -O- or -CO-, the carbon between the terminal and -O- or -CO-, or between -O- or -CO- and -O- or -CO- The number of atoms is, for example, 1 to 5, preferably 2 to 3, and more preferably 2. However, adjacent -CH ₂ - will not be replaced by -O- at the same time.

In addition, the optionally substituted aromatic hydrocarbon group represented by R ^11b to R ^16b and R ^26b preferably has 6 to 20 carbon atoms, more preferably 6 to 15 carbon atoms, and further preferably 6 carbon atoms. to 12. Examples of the aromatic hydrocarbon group include aryl groups such as phenyl, tolyl, styryl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, and terphenyl groups, and preferred ones are phenyl, naphthyl, tolyl, As the stubble group, phenyl and tolyl are particularly preferred. In addition, the aromatic hydrocarbon group preferably has one or more substituents. Examples of the substituents include: halogen atoms such as fluorine atom, chlorine atom, iodine atom and bromine atom; methoxy group and ethoxy group Alkoxy groups with 1 to 6 carbon atoms such as; hydroxyl; sulfamoyl; methylsulfonyl and other alkylsulfamoyl groups with 1 to 6 carbon atoms; methoxycarbonyl, ethoxycarbonyl Alkoxycarbonyl groups with 1 to 6 carbon atoms; etc.

Examples of the optionally substituted aralkyl group represented by R ^11b to R ^16b include alkylenediyl groups having 1 to 5 carbon atoms such as methylene, ethylene, and propylene, as well as those described above as aromatic hydrocarbon groups. Groups formed by bonding groups, etc.

R ^11b and R ^12b are bonded to form a ring together with the nitrogen atom to which they are bonded, R ^13b and R ^14b are bonded to form a ring together with the nitrogen atom to which they are bonded, and R ^15b and R ^16b are bonded. Examples of the rings formed together with the nitrogen atoms to which they are bonded include nitrogen-containing non-aromatic 4 to 7-membered rings such as pyrrolidine ring, mofolin ring, piperidine ring, piperazine ring, etc. There are 4 to 7-membered rings with only 1 nitrogen atom as a heteroatom, such as pyrrolidine ring and piperidine ring.

Among them, R ^11b to R ^14b and R ^26b are preferably a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group which may have a substituent, and each independently is more preferably a saturated hydrocarbon group having 1 to 8 carbon atoms or A group represented by the following formula. In the following formula, * represents a bonding end, and Me represents a methyl group.

R ^11b and R ^13b are each independently preferably a saturated hydrocarbon group having 1 to 10 carbon atoms. R ^12b and R ^14b are each independently preferably an aromatic hydrocarbon group which may have a substituent. R ^26b is preferably an aromatic hydrocarbon group which may have a halogen atom. of aromatic hydrocarbon groups.

R ^11b and R ^13b are each independently more preferably a saturated hydrocarbon group having 1 to 6 carbon atoms, R ^12b and R ^14b are each independently more preferably an aromatic hydrocarbon group, and R ^26b is more preferably an aromatic hydrocarbon group which may have a fluorine atom.

R ^11b and R ^13b are each independently preferably a methyl group or an ethyl group, R ^12b and R ^14b are each independently preferably a phenyl group, and R ^26b is further preferably a phenyl group having a fluorine atom.

R ^15b and R ^16b are each independently preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, a group in which -O- is inserted between the carbon atoms of an alkyl group having 2 to 20 carbon atoms, or a group which may have a substituent. The aromatic hydrocarbon group, or R ^15b and R ^16b are bonded to form a ring together with the nitrogen atom to which they are bonded. A more preferred aspect is that R ^15b and R ^16b are each independently a saturated hydrocarbon group having 1 to 8 carbon atoms, an alkoxyalkyl group, or a group represented by the following formula, or R ^15b and R ^16b are bonded together. It forms a 4- to 7-membered ring having only 1 nitrogen atom as a heteroatom. In the following formula, * represents the bonding end with a nitrogen atom, and Me represents a methyl group.

In addition, a group in which -CH ₂ - of the alkyl group having 1 to 8 carbon atoms and the alkyl group having 2 to 8 carbon atoms represented by R ^17b to R ^24b is replaced with -O- or -CO- may be A group having 8 or less carbon atoms selected from the corresponding groups of R ^11b to R ^16b is exemplified.

From the viewpoint of ease of synthesis, R ^17b to R ^24b are preferably each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 8 carbon atoms, and each independently more preferably a hydrogen atom, a methyl group, a fluorine atom or The chlorine atom is each independently preferably a hydrogen atom.

X1b is preferably a sulfur atom.

Examples of the cation part of the formula (A2) include cations 1 to 14 represented by the formula (I-1), as shown in Table 1 below. [Table 1]

In Table 1, Ph1 to Ph9 represent groups represented by the following formulas. In the formula, * represents the bonding end.

Among them, the cation part of the formula (A2) is preferably cation 1 to cation 6, cation 11 to cation 14, more preferably cation 1, cation 2, or cation 12 to cation 14, and further preferably cation 12.

[Y] ^m- is any m-valent anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen. Compounds containing such anions tend to have good heat resistance and solvent resistance.

m is preferably from 1 to 20, more preferably from 1 to 14, further preferably from 2 to 8, still more preferably from 2 to 6.

The anion represented by [Y] ^m- is preferably an anion of a tungsten-containing heteropoly acid (heteropoly acid) or an anion of a tungsten-containing isopoly acid (isopoly acid).

Examples of the anion of the tungsten-containing heteropolymeric acid or homopolymeric acid include Keggin type phosphotungstic acid ion α-[PW ₁₂ O ₄₀ ] ^3- and Dawson type phosphotungstic acid ion α-[P ₂ W ₁₈ O ₆₂ ] ^6- , β-[P ₂ W ₁₈ O ₆₂ ] ^6- , Keggin type silicotungstic acid ion α-[SiＷ ₁₂ O ₄₀ ] ^4- , β-[SiW ₁₂ O ₄₀ ] ^4- , γ-[ SiＷ ₁₂ O ₄₀ ] ^4- , [P ₂ Ｗ ₁₇ O ₆₁ ] ^10- , [P ₂ Ｗ ₁₅ O ₅₆ ] ^12- , [H ₂ P ₂ Ｗ ₁₂ O ₄₈ ] ^12- , [NaP ₅ Ｗ ₃₀ O ₁₁₀ ] ^14- , α-[SiW ₉ O ₃₄ ] ^10- , γ-[SiW ₁₀ O ₃₆ ] ^8- , α-[SiW ₁₁ O ₃₉ ] ^8- , β-[SiW ₁₁ O ₃₉ ] ^8- , [W ₆ O ₁₉ ] ^2- , [W ₁₀ O ₃₂ ] ^4- , WO ₄ ^2- and mixtures thereof.

The anion represented by [Y] ^m- is also preferably an anion composed of at least one element selected from the group consisting of silicon and phosphorus, and oxygen.

Examples of the anion composed of at least one element selected from the group consisting of silicon and phosphorus and oxygen include SiO ₃ ^2- and PO ₄ ^3- .

From the perspective of ease of synthesis and post-processing, phosphotungstic acid anions such as Keggin-type phosphotungstic acid ions and Dawson-type phosphotungstic acid ions are preferred; silicotungstic acid anions such as Keggin-type silicotungstic acid ions; [W ₁₀ O ₃₂ ] ^4- Tungsten isotopic polymeric acid anion. Among them, Keggin-type phosphotungstic acid anion and tungsten-based homopolymeric acid anion are particularly preferred.

Examples of compound (A2) include compounds represented by formulas (A2-1) to formula (A2-52) in Tables 2 to 3 below. [Table 2] [table 3]

Compound (A2) is preferably a compound represented by formula (A2-41) to formula (A2-44), and more preferably a compound represented by formula (A2-41).

Compound (A2) can be produced according to the method described in Japanese Patent Application Laid-Open No. 2015-28121.

＜＜Compound (A3)＞ [In formula (A3), R ^41b to R ^44b each independently represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or a substituted The aromatic hydrocarbon group and the aralkyl group may have an aralkyl group having 7 to 30 carbon atoms. The substituent that the aromatic hydrocarbon group and the aralkyl group may have may be -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . The saturated The hydrogen atoms contained in the hydrocarbon group can be replaced by substituted or unsubstituted amino groups or halogen atoms. When the number of carbon atoms in the saturated hydrocarbon group is 2 to 20, the -CH ₂ - contained in the saturated hydrocarbon group can be replaced by -O -or-CO-displacement. However, in the saturated hydrocarbon group with 2 to 20 carbon atoms, adjacent -CH ₂ - will not be replaced by -O- at the same time. R ^41b and R ^42b may be bonded to form a ring together with the nitrogen atom to which they are bonded, and R ^43b and R ^44b may be bonded to form a ring together with the nitrogen atom to which they are bonded. R ^47b to R ^54b each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, -SO ₃ ^- , -SO ₂ -N ^- -SO ₂ -R ^f , or an alkyl group having 1 to 8 carbon atoms, and constitute -CH ₂ - of the alkyl group may be replaced by -O- or -CO-, and R ^48b and R ^52b may be bonded to each other to form -NH-, -S-, or -SO ₂ -. However, in this alkyl group, adjacent -CH ₂ - will not be replaced by -O- at the same time. Ring T ^2b represents an aromatic heterocyclic ring with 3 to 10 carbon atoms or an aromatic hydrocarbon ring with 6 to 10 carbon atoms. The aromatic heterocyclic ring and the aromatic hydrocarbon ring may have a saturated hydrocarbon group with 1 to 20 carbon atoms. , a substituted or unsubstituted amino group or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. The aromatic hydrocarbon group may have -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f as a substituent. M ^r+ represents a metal ion with r valence. k represents the sum of the number of -SO ₃ ^- and the number of -SO ₂ -N ^- -SO ₂ -R ^f that R ^41b to R ^44b , R ^47b to R ^54b and ring T ^2b have. r represents an integer above 1. R ^f represents a fluoroalkyl group having 1 to 12 carbon atoms. Among them, R ^41b to R ^44b , R ^47b to R ^54b and ring T ^2b have at least one -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . In addition, when one molecule contains a plurality of structures represented by the following formulas, they may be the same or different structures. [In the formula, each of Ring T ^2b , R ^41b to R ^44b and R ^47b to R ^54b has the same meaning as above. ]]

The aromatic heterocyclic ring represented by ring T ^2b may be a monocyclic ring or a condensed ring. The number of carbon atoms of the aromatic heterocyclic ring represented by ring T ^2b is preferably 3 to 10, more preferably 3 to 8. In addition, the aromatic heterocyclic ring is preferably a 5- to 10-membered ring, more preferably a 5- to 9-membered ring. Examples of the monocyclic aromatic heterocyclic ring include five-membered rings containing nitrogen atoms such as pyrrole ring, oxazole ring, pyrazole ring, imidazole ring, and thiazole ring; and those containing no nitrogen atoms such as furan ring and thiophene ring. 5-membered rings; 6-membered rings containing nitrogen atoms such as pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, etc. Examples of condensed aromatic heterocyclic rings include condensed rings containing nitrogen atoms such as indole rings, benzimidazole rings, benzothiazole rings, and quinoline rings; condensed rings containing no nitrogen atoms such as benzofuran rings; wait.

Among them, the aromatic heterocyclic ring of ring T ^2b is preferably an aromatic heterocyclic ring containing a nitrogen atom, and more preferably a 5-membered aromatic heterocyclic ring containing a nitrogen atom.

Examples of substituents that the aromatic heterocyclic ring T ^2b may have include a halogen atom, a cyano group, a saturated hydrocarbon group having 1 to 20 carbon atoms that may have a substituent, a substituted or unsubstituted amino group, or An aromatic hydrocarbon group having 6 to 20 carbon atoms, etc., which may have a substituent, preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted amino group, or a carbon atom group which may have a substituent. 6 to 20 aromatic hydrocarbon groups. Ring T ^2b preferably has an amino group which may have a substituent, and the substituent that the amino group may have is preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, or a saturated hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. An aromatic hydrocarbon group, an aralkyl group having 7 to 30 carbon atoms which may have a substituent, etc.

Ring T ^2b is preferably a ring represented by formula (A3-t1). [In formula (A3-t1), R ^56b represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. X2b represents an oxygen atom, -N(R ^57b )-, or a sulfur atom. R ^57b represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. R ^45b and R ^46b each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or a carbon atom which may have a substituent. For an aralkyl group with a number of 7 to 30, when the carbon number of the saturated hydrocarbon group is 2 to 20, -CH ₂ - contained in the saturated hydrocarbon group can be replaced by -O- or -CO-. However, in the saturated hydrocarbon group with 2 to 20 carbon atoms, adjacent -CH ₂ - will not be replaced by -O- at the same time. R ^45b and R ^46b may be bonded to form a ring together with the nitrogen atoms to which they are bonded. * indicates the bonding end with the carbocation. ]

In addition, ring T ^2b is also preferably a ring represented by formula (A3-t2). [In formula (A3-t2), R ^59b represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or a substituted Aralkyl group having 7 to 30 carbon atoms. R ^60b represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. R ^61b represents a hydrogen atom, -SO ₃ ^- , or -SO ₂ -N ^- -SO ₂ -R ^f . * indicates the bonding end with the carbocation. ]

Examples of the aromatic hydrocarbon ring represented by ring T ^2b include a benzene ring, a naphthalene ring, and the like.

Examples of substituents that the aromatic hydrocarbon ring represented by ring T ^2b may have include the substituents that the above-mentioned aromatic heterocyclic ring may have.

The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^41b to R ^46b , R ^56b , and R ^59b to R ^60b and the saturated hydrocarbon group having 1 to 20 carbon atoms that the amine group of ring T ^2b may have may be Any of linear, branched and cyclic. Examples of linear or branched saturated hydrocarbon groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, and Straight-chain alkyl groups such as hexalkyl and eicosanyl; branched-chain alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl. The number of carbon atoms of the saturated hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 6.

The cyclic saturated hydrocarbon group represented by R ^41b to R ^46b , R ^56b , and R ^59b to R ^60b and the cyclic saturated hydrocarbon group that the amino group that ring T ^2b may have may have a monocyclic ring or a polycyclic ring. Examples of the cyclic saturated hydrocarbon group include alicyclic saturated hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl. The number of carbon atoms of the cyclic saturated hydrocarbon group is preferably 3 to 10, more preferably 6 to 10.

The saturated hydrocarbon groups represented by R ^41b to R ^46b , R ^56b and R ^59b to R ^60b and the saturated hydrocarbon group that the ring T ^2b may have may have a substituted or unsubstituted amino group or a halogen atom. substituents. Examples of substituted amino groups include alkylamino groups such as methylamino group, dimethylamino group, and diethylamine group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Furthermore, when the halogen atom is a fluorine atom, the saturated hydrocarbon group having a fluorine atom as a substituent is preferably a perfluoroalkyl group such as trifluoromethyl, perfluoroethyl, or perfluoropropyl.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R ^47b to R ^54b include linear or branched saturated hydrocarbon groups having 1 to 8 carbon atoms exemplified as the saturated hydrocarbon group represented by R ^41b group.

Examples of the alkyl group having 1 to 10 carbon atoms represented by R ^57b include linear or branched saturated hydrocarbon groups having 1 to 10 carbon atoms exemplified as the saturated hydrocarbon group represented by R ^41b . group.

When the number of carbon atoms of the saturated hydrocarbon group represented by R ^41b to R ^46b is 2 to 20, -CH ₂ - contained in the saturated hydrocarbon group may be replaced by -O- or -CO-. However, in the saturated hydrocarbon group with 2 to 20 carbon atoms, adjacent -CH ₂ - will not be replaced by -O- at the same time. In this case, the saturated hydrocarbon group is preferably a linear or branched saturated hydrocarbon group (i.e., a linear or branched alkyl group), and more preferably a linear saturated hydrocarbon group (i.e., a linear alkyl group). base). -CH ₂ -The preferred number of carbon atoms of the saturated hydrocarbon group that can be replaced by -O- or -CO- is 2 to 10, more preferably 2 to 8. In addition, when -CH ₂ - is replaced by -O- or -CO-, the carbon between the terminal and -O- or -CO-, or between -O- or -CO- and -O- or -CO- The number of atoms is preferably 1 to 5, more preferably 2 to 3, and still more preferably 2.

In addition, the aromatic hydrocarbon group represented by R ^41b to R ^46b , R ^56b and R ^59b to R ^60b which may have a substituent and the aromatic hydrocarbon group which the amine group of ring T ^2b may have (wherein, the aromatic hydrocarbon group The number of carbon atoms (which may have a substituent) is preferably 6 to 20, more preferably 6 to 15, further preferably 6 to 12. Examples of the aromatic hydrocarbon group include phenyl, tolyl, stubble, naphthyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, and the like, with phenyl, tolyl, stubble, and naphthyl being preferred. , particularly preferred are phenyl, tolyl and stubble. In addition, the aromatic hydrocarbon group may have one or more substituents. Examples of the substituent include halogen atoms such as fluorine atom, chlorine atom, iodine atom and bromine atom; alkoxy groups having 1 to 6 carbon atoms such as methoxy group and ethoxy group; hydroxyl group; sulfamide group; methyl group Alkyl sulfonyl groups with 1 to 6 carbon atoms such as methylsulfonyl group; alkoxycarbonyl groups with 1 to 6 carbon atoms such as methoxycarbonyl group and ethoxycarbonyl group; -SO ₃ ^- ; -SO ₂ -N ^- -SO ₂ -R ^f ; etc., preferably halogen atoms such as fluorine atom, chlorine atom, iodine atom, bromine atom; -SO ₃ ^- ; -SO ₂ -N ^- -SO ₂ -R ^f , more preferably fluorine Atom or -SO ₃ ^- . Among them, -SO ₃ ^- and -SO ₂ -N ^- -SO ₂ -R ^f are preferably directly bonded to the aromatic hydrocarbon ring of the aromatic hydrocarbon group, that is, the hydrogen atoms bonded to the aromatic hydrocarbon ring are replaced. .

Specific examples of the aromatic hydrocarbon group which may have a substituent include groups represented by the following formulas. In the following formula, * represents the bonding end.

As the aralkyl group represented by R ^41b to R ^46b and R ^59b that may have a substituent and the aralkyl group that the amine group that ring T ^2b may have (where the aralkyl group may have a substituent), there may be Examples include those in which an alkylenediyl group having 1 to 10 carbon atoms (preferably 1 to 5 carbon atoms), such as a methylene group, an ethylene group, or a propylene group, is bonded to the group described as the aromatic hydrocarbon group. Group etc. The number of carbon atoms of the aralkyl group is preferably 7 to 30, more preferably 7 to 20, even more preferably 7 to 17.

R ^41b and R ^42b are bonded to form a ring together with the nitrogen atom to which they are bonded, R ^43b and R ^44b are bonded to form a ring together with the nitrogen atom to which they are bonded, and R ^45b and R ^46b are bonded Examples of the rings formed together with the nitrogen atoms to which they are bonded include nitrogen-containing non-aromatic 4 to 7-membered rings such as pyrrolidine ring, mofolin ring, piperidine ring, piperazine ring, etc. There are 4 to 7-membered rings with only 1 nitrogen atom as a heteroatom, such as pyrrolidine ring and piperidine ring.

Among them, R ^41b to R ^44b , R ^56b , and R ^59b to R ^60b are each independently preferably a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group which may have a substituent, and each independently more preferably is a carbon A saturated hydrocarbon group having 1 to 8 atoms or a group represented by the following formula, R ^41b and R ^43b are each independently more preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, and R ^42b and R ^44b are each independently more preferably It is an aromatic hydrocarbon group which may have a substituent, and R ^56b is more preferably an aromatic hydrocarbon group which may have a substituent.

More preferably, R ^56b and R ^59b to R ^60b are groups represented by the following formula. In the following formula, * represents the bonding end.

R ^45b to R ^46b are each independently preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, or a group in which -CH ₂ - constituting an alkyl group having 2 to 20 carbon atoms is replaced with -O- or -CO- , or an aromatic hydrocarbon group which may have a substituent, or R ^45b and R ^46b are bonded to form a ring together with the nitrogen atom to which they are bonded. R ^45b to R ^46b are each independently more preferably a saturated hydrocarbon group having 1 to 8 carbon atoms, an alkoxyalkyl group, or a group represented by the following formula, or R ^45b and R ^46b are bonded to form a group having only one The 4- to 7-membered ring in which the nitrogen atom is a hetero atom is each independently more preferably a saturated hydrocarbon group having 1 to 8 carbon atoms, an alkoxyalkyl group, or a group represented by the following formula. Among them, R ^45b is more preferably a saturated hydrocarbon group having 1 to 4 carbon atoms, and R ^46b is more preferably a tolyl group. In the following formula, * represents the bonding end with the nitrogen atom.

In addition, as a group represented by R ^47b to R ^54b , -CH ₂ - constituting an alkyl group having 2 to 8 carbon atoms is replaced by -O- or -CO- (wherein, in the alkyl group, Ortho -CH ₂ - will not be replaced by -O- at the same time), examples of which include -CH ₂ - constituting an alkyl group having 2 to 20 carbon atoms represented by the above-mentioned R ^41b to R ^46b and being replaced by -O- or -CO - A group having 8 or less carbon atoms in the substituted group.

R ^47b to R ^54b are each independently preferably a hydrogen atom, a halogen atom or an alkyl group having 1 to 8 carbon atoms, each independently more preferably a hydrogen atom, a methyl, a fluorine atom or a chlorine atom, each independently further preferably is a hydrogen atom.

Furthermore, R ^57b is preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.

R ^61b is preferably a hydrogen atom.

As X2b, -S- is preferred.

Examples of r-valent metal ions represented by M ^r+ include alkali metal ions such as lithium ions, sodium ions, and potassium ions; alkaline earth metal ions such as beryllium ions, magnesium ions, calcium ions, strontium ions, and barium ions; titanium ions, Transition metal ions such as zirconium ions, chromium ions, manganese ions, iron ions, cobalt ions, nickel ions, and copper ions; typical metal ions such as zinc ions, cadmium ions, aluminum ions, indium ions, tin ions, lead ions, and bismuth ions, etc. . r is 1 or more, preferably 2 or more, preferably 5 or less, more preferably 4 or less, still more preferably 3 or less.

As M ^r+ , alkaline earth metal ions, typical metal ions, etc. are more preferred, alkaline earth metal ions and zinc ions are further preferred, and alkaline earth metal ions are further preferred.

In formula (A3), the number of M ^r+ is the number of -SO _{3 - and -SO 2} ^{-N -} -SO ₂ - that R ^41b to R ^44b , R ^47b to R ^54b and ring T ^2b have. The sum of the numbers of R ^f (k) is one less than the number. Therefore, the valence of compound (A3) becomes 0, that is, it becomes an electrically neutral compound.

Examples of the fluoroalkyl group having 1 to 12 carbon atoms represented by R ^f include monofluoromethyl, difluoromethyl, perfluoromethyl, monofluoroethyl, difluoroethyl, and trifluoroethyl. Tetrafluoroethyl, perfluoroethyl, monofluoropropyl, difluoropropyl, trifluoropropyl, tetrafluoropropyl, pentafluoropropyl, hexafluoropropyl, perfluoropropyl, monofluorobutyl, Difluorobutyl, trifluorobutyl, tetrafluorobutyl, pentafluorobutyl, hexafluorobutyl, heptafluorobutyl, octafluorobutyl, perfluorobutyl, etc. Among these, the fluoroalkyl group represented by R ^f is preferably a perfluoroalkyl group. In addition, the number of carbon atoms of the fluoroalkyl group represented by R ^f is preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3.

In formula (A3), R ^41b to R ^44b , R ^47b to R ^54b and ring T ^2b have at least one -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f , preferably at least one -SO _3- ^. The sum (k) of the numbers -SO ₃ ^- and -SO ₂ -N ^- -SO ₂ -R ^f of R ^41b to R ^44b , R ^47b to R ^54b and ring T ^2b is preferably 1 to 7 , more preferably 2 to 7, still more preferably 2 to 4, further preferably 2 or 3, particularly preferably 2.

-SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f preferably satisfies at least one condition selected from the following (Ia) to (Id), and more preferably satisfies the condition selected from the group consisting of (Ia) and (Id). At least one of the conditions in Ib). (Ia) includes (Ib) as any one of the above-mentioned R ^47b to R ^54b , a bond with any one of the aromatic hydrocarbon groups having 6 to 20 carbon atoms represented by R ^41b to R ^44b which may have a substituent The bond (Ic) is bonded to any one of the aralkyl groups having 7 to 30 carbon atoms represented by R ^41b to R ^44b which may have a substituent. The bond (Id) is bonded to the aromatic heterocyclic ring represented by T ^2b Any one of the aromatic hydrocarbon groups having 6 to 20 carbon atoms replaced by a hydrogen atom is bonded

Among them, when -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f is bonded to the aromatic hydrocarbon group or aralkyl group, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R System ^f is preferably directly bonded to an aromatic hydrocarbon group or an aromatic hydrocarbon ring of an aralkyl group. That is, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f preferably replaces the hydrogen atom bonded to the aromatic hydrocarbon ring.

In the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R ^41b to R ^44b which may have a substituent or the aralkyl group having 7 to 30 carbon atoms represented by R ^41b to R ^44b which may have a substituent In an aromatic hydrocarbon ring (such as a benzene ring), -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f is preferably bonded at the para position opposite to the bonding position of the nitrogen atom.

In the case where the compound (A3) contains a plurality of -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f , a plurality of -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f may be bonded It can be bonded to the same aromatic hydrocarbon ring, or it can be bonded to different aromatic hydrocarbon rings.

The compound (A3) preferably does not have an ethylenically unsaturated bond.

Compound (A3) is preferably a compound represented by the following formula (II-1) (hereinafter, may be referred to as compound (II-1)). [In formula (II-1), R ^81b to R ^90b each independently represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ - R ^f . k1 represents the number of -SO ₃ ^- and the number of -SO ₂ -N ^- -SO ₂ -R ^f that R ^41b , R ^43b , R ^47b to R ^54b , R ^81b to R ^90b and ring T ^2b have. and. R ^41b , R ^43b , R ^47b to R ^54b , T ^2b , M ^r+ , r, and R ^f are synonymous with the above. Among them, R ^41b , R ^43b , R ^47b to R ^54b , R ^81b to R ^90b and ring T ^2b have at least one -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . ]

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^81b to R ^90b include the same groups as those exemplified as the saturated hydrocarbon group represented by R ^41b . R ^81b to R ^90b are preferably a hydrogen atom, a saturated hydrocarbon group having 1 to 8 carbon atoms, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f , and more preferably a hydrogen atom, a saturated hydrocarbon group having 1 to 8 carbon atoms. A saturated hydrocarbon group having 1 to 4 carbon atoms, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f is more preferably a hydrogen atom, a saturated hydrocarbon group having 1 to 4 carbon atoms, or -SO ₃ ^- .

-SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f preferably satisfies at least one condition selected from (Ie) to (Ig), and more preferably satisfies the condition selected from (If) and (Ig) ) at least one of the conditions, preferably satisfying the condition of (If). (Ie) Contains (If) as any one of R ^47b to R ^54b ) Contains (Ig) as any one of R ^81b to R ^90b Replacement of the hydrogen atom of the aromatic heterocyclic ring represented by T ^2b Aromatic hydrocarbon group with 6 to 20 carbon atoms bonded

-SO ₃ ^-or -SO ₂ -N ^- -SO ₂ -R ^f further preferably satisfies the condition of (If'). (If') Contains either or both of R ^86b and R ^89b

In the formula (II-1), R ^41b , R ^43b , R ^47b to R ^54b , R ^81b to R ^90b , and ring T ^2b have -SO ₃ ^- and -SO ₂ -N ^- -SO ₂ -R ^f The sum of the numbers (k1) is preferably 1 to 7, more preferably 1 to 4, and further preferably 1 or 2.

Examples of the compound (A3) include the compounds shown below (compounds represented by formula (A3-1) to formula (A3-13)).

Among the compounds represented by formula (A3-1) to formula (A3-13), compounds represented by formula (A3-7), formula (A3-11), or formula (A3-13) are preferred, especially Preferred are compounds represented by formula (A3-7).

When producing the colored resin composition of the present invention, the triarylmethane lake is preferably dispersed in a solvent to prepare a colored dispersion liquid. This colored dispersion liquid can be mixed with anthraquinone compound (A1), resin (B), polymerizable compound (C), polymerization initiator (D), etc. to prepare a colored resin composition.

As a solvent when preparing this colored dispersion liquid, any solvent can be used as long as it can be used as the solvent (E) of the colored resin composition. Examples of the solvent include ether ester solvents and ketone solvents described below.

In the coloring dispersion liquid, the content of the solvent is, for example, 1 to 50 parts by mass, preferably 2 to 30 parts by mass, and more preferably 3 to 20 parts by mass relative to 1 part by mass of the triarylmethane lake.

When preparing a color dispersion by dispersing triarylmethane lake in a solvent, a pigment dispersant is preferably used. Examples of pigment dispersants include cationic, anionic, nonionic, amphoteric, polyester, polyamine, acrylic and other surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of the pigment dispersant include trade names KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by Zeneca Chemical Co., Ltd.) Manufactured by BASF Corporation), Ajispur (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (manufactured by BYK Chemical Company), BYK (manufactured by BYK Chemical Company), etc.

In the coloring dispersion liquid, the content of the pigment dispersant is, for example, 1 to 1000 parts by mass, preferably 3 to 200 parts by mass, and more preferably 5 to 100 parts by mass, relative to 100 parts by mass of the triarylmethane lake. Preferably, it is 5 to 50 parts by mass.

In the total amount of the colorant (A), the content rate of the triarylmethane lake is, for example, 5 mass% or more, preferably 10 mass% or more, more preferably 20 mass% or more, for example, 99 mass% or less, preferably Preferably, it is 95 mass % or less, More preferably, it is 90 mass % or less.

<Anthraquinone compound (A1)>

The anthraquinone compound used as the colorant (A) is a compound represented by formula (A1) (hereinafter, may be referred to as "anthraquinone compound (A1)"). [In formula (A1), A ^1a and A ^2a each independently represent a phenylene group which may have a substituent. L ^1a and L ^2a each independently represent a divalent hydrocarbon group having 1 to 12 carbon atoms, and -CH ₂ - contained in the hydrocarbon group may be replaced by -O-, -SO ₂ - or -NR ^11a -. R ^1a to R ^6a each independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 8 carbon atoms. R ^11a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. ]

Examples of the substituent that the phenylene group represented by A ^1a and A ^2a may have include a halogen atom (chlorine atom, bromine atom, etc.), -R ^21a , -OH, -OR ^21a , -SO ₃ H, - SO ₃ ^- G ⁺ , -COOH, -COO ^- T ⁺ , -CO ₂ R ^21a , -SR ^21a , -SO ₂ R ^21a , -SO ₃ R ^21a or -SO ₂ NR ^12a R ^13a . The above-mentioned R ^21a represents a saturated hydrocarbon group having 1 to 20 carbon atoms. When -R ^21a , R ^21a is preferably an alkyl group having 1 to 8 carbon atoms. The above-mentioned R ^12a and R ^13a each independently represent a hydrogen atom, a saturated hydrocarbon group with 1 to 20 carbon atoms, or an aralkyl group with 7 to 10 carbon atoms. R ^12a and R ^13a may be bonded to the nitrogen to which they are bonded. Atoms come together to form rings. G ⁺ is Na ⁺ , K ⁺ , or N ⁺ (R ^15a ) ₄ , T ⁺ is Na ⁺ , K ⁺ , or N ⁺ (R ^16a ) ₄ , four R ^15a can be the same or different, four R ^16a Can be the same or different. R ^15a and R ^16a represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

Among the above substituents, -R ^21a , -SO ₃ H, -SO ₃ ^- G ⁺ , -COOH, -COO ^- T ⁺ and -SO ₂ NR ^12a R ^13a are preferred, as -SO ₃ ^- in this case G ⁺ , preferably -SO ₃ ^- N ⁺ (R ^15a ) ₄ . The most preferred substituent is -R ^21a .

Examples of the alkyl group having 1 to 8 carbon atoms represented by R ^1a to R ^6a , R ^11a , R ^15a , R ^16a and R ^21a include methyl, ethyl, propyl, butyl, and pentyl groups. , hexyl and other straight-chain alkyl groups; isopropyl, isobutyl, isopentyl, neopentyl and other branched-chain alkyl groups. Among them, R ^1a to R ^6a and R ^11a are preferably hydrogen atoms.

Examples of the hydrocarbons having 1 to 12 carbon atoms constituting the divalent group represented by L ^1a and L ^2a include aliphatic saturated hydrocarbons having 1 to 12 carbon atoms, benzene, and alkanes having 1 to 8 carbon atoms. Based benzene etc. Examples of the divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms include methylene, ethane-1,2-diyl, propane-1,3-diyl, and butane-1,4-diyl. , pentane-1,5-diyl, hexane-1,6-diyl and other straight-chain alkanediyl groups with bonding ends at both ends; ethane-1,1-diyl, propane-1,1- Diyl, propane-1,2-diyl, propane-2,2-diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl , butane-2,2-diyl, butane-2,3-diyl, 2-methylpropane-1,1-diyl, 2-methylpropane-1,2-diyl, 2-methyl propane-1,3-diyl, 2-methylpropane-1,4-diyl, 2-methylpropane-2,3-diyl, 2-methylpropane-2,4-diyl, 2 -Methylpropane-3,3-diyl, 2-methylpropane-3,4-diyl, 2-methylpropane-4,4-diyl, etc., preferably straight chains with bonded ends at both ends alkanediyl.

Examples of the benzene having an alkyl group having 1 to 8 carbon atoms include methylbenzene, dimethylbenzene, ethylbenzene, propylbenzene, ethyl(methyl)benzene, butylbenzene, ethyl(dimethyl)benzene, Methyl)benzene, etc., the divalent group formed from the benzene having an alkyl group with 1 to 8 carbon atoms may have two bonding ends on the alkyl group, or may have two bonds on the benzene ring. The bonding end may also have one bonding end on the alkyl group and one bonding end on the benzene ring. Among these, an aspect having one bonding end on the alkyl group and one bonding end on the benzene ring is preferred.

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^12a , R ^13a and R ^21a include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, Linear alkyl groups such as nonyl, decyl, dodecyl, hexadecyl, and eicosanyl; branched groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl Chain alkyl; alicyclic saturated hydrocarbon groups with 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, tricyclodecyl and other carbon atoms. The number of carbon atoms of the saturated hydrocarbon group is more preferably 1 to 10.

Examples of the aralkyl group having 7 to 10 carbon atoms represented by R ^12a and R ^13a include benzyl group, phenylethyl group, phenylbutyl group, and the like.

Examples of the ring in which R ^12a and R ^13a are bonded together with the nitrogen atom to which they are bonded form the following rings. In the formula, * represents the bonding end.

Examples of N ⁺ (R ^15a ) ₄ and N ⁺ (R ^16a ) ₄ include tetramethylammonium, tetraethylammonium, tetrapropylammonium, and tetrabutylammonium.

Examples of -OR ^21a include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy and Eicosyloxy and other alkoxy groups.

Examples of -CO ₂ R ^21a include alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tertiary butoxycarbonyl, hexyloxycarbonyl, and eicosyloxycarbonyl. wait.

Examples of -SR ^21a include methylsulfanyl, ethylsulfanyl, butylsulfanyl, hexylsulfanyl, decylsulfanyl, and eicosanylsulfanyl. Alkyl sulfide, etc.

Examples of -SO ₂ R ^21a include alkyl groups such as methylsulfonyl group, ethylsulfonyl group, butylsulfonyl group, hexylsulfonyl group, decylsulfonyl group and eicosylsulfonyl group. Sulfonyl group, etc.

Examples of -SO ₃ R ^21a include methoxysulfonyl group, ethoxysulfonyl group, propoxysulfonyl group, tertiary butoxysulfonyl group, hexyloxysulfonyl group and di- Decalkoxysulfonyl group, etc. Alkoxysulfonyl group, etc.

Examples of -SO ₂ NR ^12a R ^13a include: aminesulfonyl group; N-methylaminesulfonyl group, N-ethylaminesulfonyl group, N-propylaminesulfonyl group, N-iso Propylamine sulfonyl, N-butylamine sulfonyl, N-isobutylamine sulfonyl, N-secondary butylamine sulfonyl, N-tertiary butylamine sulfonyl, N- Pentyl sulfonamide, N-(1-ethylpropyl) sulfonamide, N-(1,1-dimethylpropyl) sulfonamide, N-(1,2-dimethyl) Propyl)aminesulfonyl, N-(2,2-dimethylpropyl)aminesulfonyl, N-(1-methylbutyl)aminesulfonyl, N-(2-methylbutyl) ) sulfonamide group, N-(3-methylbutyl) sulfonamide group, N-cyclopentyl sulfonamide group, N-hexyl sulfonamide group, N-(1,3-dimethylbutyl) base) sulfonamide group, N-(3,3-dimethylbutyl) sulfonamide group, N-heptyl sulfonamide group, N-(1-methylhexyl) sulfonamide group, N- (1,4-Dimethylpentyl)aminesulfonyl, N-octylaminesulfonyl, N-(2-ethylhexyl)aminesulfonyl, N-(1,5-dimethylhexyl) ) sulfamic acid group, N-(1,1,2,2-tetramethylbutyl) sulfamic acid group and other N-1 substituted sulfamic acid group; N,N-dimethyl sulfamic acid group, N ,N-ethylmethylsulfonamide, N,N-diethylsulfonamide, N,N-propylmethylsulfonamide, N,N-isopropylmethylsulfonamide , N,N-tertiary butylmethylmethanesulfonyl, N,N-butylethylaminesulfonyl, N,N-bis(1-methylpropyl)aminesulfonyl, N,N-heptyl Methyl sulfonamide group, etc. N, N-2 substituted sulfonamide group, etc.

Examples of the halogen atom that the halogen atom represented by R ^1a to R ^6a and the phenylene group represented by A ^1a and A ^2a may have as a substituent include a chlorine atom and a bromine atom.

As the anthraquinone compound (A1), the formula (A1) is preferably *-L ^1a - ** (* represents the bonding end with A ^1a , ** represents the bonding end with CO ₂ H) and *-L ^2a - ** (* represents the bonding end with A ^2a , ** represents the bonding end with CO ₂ H) each independently forms a compound having a structure represented by formulas (A1a) to (A1h). [In the formulas (A1a) to (A1h), R ^31a represents an alkylenediyl group having 1 to 10 carbon atoms, R ^32a represents a phenylene group to which an alkyl group having 1 to 4 carbon atoms can be bonded, and R ^33a represents Alkanediyl group having 1 to 4 carbon atoms. ＊ represents the bonding end with A ^1a or A ^2a , and ** represents the bonding end with CO ₂ H. ]

Among the structures represented by formulas (A1a) to (A1h), structures represented by formula (A1a) and formula (A1f) are preferred.

Examples of the anthraquinone compound (A1) include a compound represented by formula (A1X) (hereinafter, may be referred to as compound (A1X)). Specific examples of the compound represented by formula (A1X) include compounds represented by formulas (A1X-1) to (A1X-36) in Table 4 below. [Table 4]

In Table 4, Me represents a methyl group, and RX1 to RX5 and RY1 to RY4 each represent a group represented by the following formula. In the formula, * represents the bonding end.

Among the compounds represented by formulas (A1X-1) to (A1X-36), compounds represented by formulas (A1X-28) to (A1X-36) are more preferred, and compounds represented by formula (A1X-36) are particularly preferred. compound of.

In the total amount of the colorant (A), the content rate of the anthraquinone compound (A1) is, for example, 1 mass% or more, preferably 3 mass% or more, more preferably 5 mass% or more, for example, 70 mass% or less, Preferably it is 60 mass % or less, More preferably, it is 50 mass % or less.

In addition, the content rate of the anthraquinone compound (A1) in the total amount of the triarylmethane lake and the anthraquinone compound (A1) is, for example, 5 mass% or more, preferably 10 mass% or more, and more preferably 13 mass% The above amount is, for example, 70 mass% or less, preferably 60 mass% or less, more preferably 50 mass% or less, further preferably 40 mass% or less.

The anthraquinone compound (A1) can be produced according to a conventional method. For example, the compound represented by formula (A1X2) can be produced according to the following synthesis scheme. [In the formula, A ^1a , A ^2a , R ^1a to R ^6a , and R ^31a have the same meanings as above. R ^51a represents an alkyl group having 1 to 4 carbon atoms. ]

More specifically, 1,4,9,10-tetrahydroxyanthracene represented by formula (A1Z) can be oxidized and the hydroxyl group can be oxidized with a hydroxylamine compound (specifically, H ₂ NA ^1a -OH, H ₂ NA ^2a -OH) to produce a compound represented by the formula (A1Y), and the compound represented by the formula (A1Y) and the compound represented by the formula Br-R ^31a -CO ₂ R ^51a are condensed by removing HBr to produce an ether compound, Next, the -CO ₂ R ^51a group is hydrolyzed to produce the target compound (A1X2).

＜Color(A4)＞

The colored resin composition of the present invention may contain dyes (hereinafter, sometimes referred to as dyes (AA)) and/or pigments (hereinafter, sometimes referred to as pigments (AB)) other than the triarylmethane lake and anthraquinone compound (A1). )) as colorant (A4).

The dye (AA) is not particularly limited as long as it does not contain the anthraquinone compound (A1), and conventional dyes can be used. Examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes.

Examples of dyes (AA) include compounds having hues other than pigments classified in the Color Index (published by The Society of Dyers and Colourists) and the Dyeing Manual ( Commonly known dyes described in Seidensha). In addition, based on the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, dibenzopyran (xanthene) dyes, phthalocyanine dyes, and anthraquinone dyes (however, anthraquinone compound (A1) is excluded) ), naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes and nitrate dyes base dyes, etc. Among these, organic solvent-soluble dyes are preferred.

The content rate of the compound classified as a dye in the above-mentioned anthraquinone compound (A1) in all dyes is, for example, 30 mass% or more, preferably 60 mass% or more, more preferably 90 mass% or more, and may be 95 mass%. Above, it may be 100% by mass.

The pigment (AB) is not particularly limited as long as it does not contain triarylmethane lake and anthraquinone compound (A1), and conventional pigments can be used, for example, the Dye Index (published by the British Institute of Dyes and Colorists) Pigments classified as pigments in .

Examples of the pigment (AB) include: C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139 , 147, 148, 150, 153, 154, 166, 173, 194, 214 and other yellow pigments; C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 and other red pigments; C.I. Pigment blue 15, 15:3, 15:4, 15:6, 60 and other blue pigments; C.I. Pigment Purple 1, 19, 23, 29, 32, 36, 38 and other purple pigments; C.I. Pigment Green 7, 36, 58 and other green pigments; C.I. Pigment Brown 23, 25 and other brown pigments; C.I. Pigment Black 1, 7 and other black pigments, etc.

If necessary, the pigment may be subjected to the following treatments: rosin treatment, surface treatment using a pigment derivative introducing an acidic group or a basic group, grafting treatment on the pigment surface using a polymer compound, etc., sulfuric acid micronization, etc. atomization treatment, cleaning treatment using an organic solvent or water to remove impurities, removal treatment of ionic impurities using an ion exchange method, etc.

The pigment preferably has a uniform particle size, and can be dispersed by containing a pigment dispersant to obtain a pigment dispersion in which the pigment is uniformly dispersed in the solution.

Examples of the pigment dispersant include the same pigment dispersants as those that can be used when preparing a colored dispersion by dispersing the aforementioned triarylmethane lake in a solvent.

In the pigment dispersion liquid, the content rate of the pigment dispersant is preferably 1 mass % or more and 100 mass % or less, and more preferably 5 mass % or more and 50 mass % or less based on the total amount of the pigment. When the content rate of the pigment dispersant is within the above range, a pigment dispersion liquid in a uniformly dispersed state tends to be obtained.

The content rate of the colorant (A) in the colored resin composition is preferably 2 to 60 mass%, more preferably 5 to 50 mass%, and even more preferably 8 to 40 mass% in the total solid content. If the content rate of the colorant (A) is within the above range, the color density when used as a color filter is sufficient, and the necessary amount of resin and polymerizable compound can be contained in the composition, so that a pattern with sufficient mechanical strength can be formed.

Here, the "total amount of solid content" in this specification means the amount excluding the content of the solvent from the total amount of the colored resin composition. The total amount of solid content and the content of each component can be measured by a conventional analysis method such as liquid chromatography or gas chromatography.

＜Resin(B)＞

The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably has at least one monomer (a) selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic anhydride (hereinafter sometimes referred to as A resin that is a structural unit of "monomer (a)"). The resin (B) further preferably has at least one structural unit selected from the group consisting of: monomer (b) derived from a cyclic ether structure having a carbon number of 2 to 4 and an ethylenically unsaturated bond ( Structural unit (hereinafter sometimes referred to as "monomer (b)"); derived from monomer (c) that can be copolymerized with monomer (a) (however, it is different from monomer (a) and monomer (b)) (hereinafter sometimes referred to as "monomer (c)"); and a structural unit having an ethylenically unsaturated bond in the side chain.

Specific examples of the monomer (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and succinic acid mono[ 2-(meth)acryloyloxyethyl] ester, etc., preferably acrylic acid, methacrylic acid, and maleic anhydride.

Monomer (b) is preferably a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxoacetate ring and a tetrahydrofuran ring) and (methane base) acryloxy-based monomer.

In addition, in this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. Expressions such as "(meth)acrylyl" and "(meth)acrylate" also have the same meaning.

Examples of the monomer (b) include glycidyl (meth)acrylate, vinylbenzyl glycidyl ether, (meth)acrylic acid-3,4-epoxytricyclo [5.2.1.0 ^2,6 ] Decyl ester, 3-ethyl-3-(meth)acryloxymethyloxyethane, (meth)acrylic acid tetrahydrofurfuryl ester, etc., preferably glycidyl (meth)acrylate, (Meth)acrylic acid-3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester, 3-ethyl-3-(meth)acrylyloxymethyloxyethane.

Examples of the monomer (c) include methyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, and 2-methylcyclohexyl (meth)acrylate. , (meth)acrylic acid tricyclo[5.2.1.02,6]decan-8-yl ester, (meth)acrylic acid benzyl ester, (meth)acrylic acid-2-hydroxyethyl ester and other (meth)acrylic acid esters; Maleimines such as N-phenylmaleimide, N-cyclohexylmaleimide, and N-benzylmaleimide; styrenic monomers such as styrene and vinyltoluene, etc. , preferably styrene, vinyltoluene, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, and N-benzylmaleimide imine.

The above-mentioned (meth)acrylates, maleimines, styrene-based monomers, etc. can be combined appropriately, and a combination of (meth)acrylates and maleimines is preferred.

The structural unit having an ethylenically unsaturated bond in the side chain can be formed as follows: monomer (b) is added to the copolymer structure of monomer (a) and monomer (c); monomer (a) is added to the monomer (b) A copolymer structure with monomer (c); or monomer (a) is added to the copolymer structure of monomer (b) and monomer (c), and carboxylic anhydride is further reacted.

The weight average molecular weight of the resin (B) in terms of polystyrene is preferably from 3,000 to 100,000, more preferably from 5,000 to 50,000, further preferably from 5,000 to 30,000.

The dispersion degree [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.

The acid value of the resin (B) is preferably 20 to 170 mg-KOH/g (mg-KOH/gram) in terms of solid content, more preferably 30 to 150 mg-KOH/g, further preferably 40 to 135 mg-KOH/g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 gram of resin (B), and can be obtained by titration using, for example, a potassium hydroxide aqueous solution.

In the total solid content of the colored resin composition, the content rate of the resin (B) is preferably 5 to 70 mass %, more preferably 15 to 60 mass %, and further preferably 20 to 50 mass %.

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized by active radicals and/or acids generated from the polymerization initiator (D). Examples thereof include compounds having a polymerizable ethylenically unsaturated bond, etc. Preferred are (meth)acrylate compounds.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, neopentylerythritol tri(meth)acrylate, neopentylerythritol tetra(meth)acrylate, and dimethacrylate. Neopenterythritol penta(meth)acrylate, dineopenterythritol hexa(meth)acrylate, etc.

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

In the total solid content of the colored resin composition, the content rate of the polymerizable compound (C) is preferably 5 to 65 mass %, more preferably 15 to 60 mass %, and further preferably 20 to 50 mass %.

<Polymerization initiator (D)>

The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat to initiate polymerization, and a conventional polymerization initiator can be used. Examples of polymerization initiators that generate active radicals include N-benzyloxy-1-(4-phenylhydrothiophenyl)butan-1-one-2-imine, N -Benzoyloxy-1-(4-phenylhydrothiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylhydrothiophenyl) Phenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylhydrothiophenyl)-3-cyclohexylpropane-1-one -2-imine, 2-methyl-2-morpholinyl-1-(4-methylhydrothiophenyl)propan-1-one, 2-dimethylamino-1-(4- Molfullinyl phenyl)-2-benzylbutan-1-one, 1-hydroxycyclohexylphenyl ketone, 2,4-bis(trichloromethyl)-6-sunfloweryl-1,3,5 -Triazine, 2,4,6-trimethylbenzyldiphenylphosphine oxide, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl Biimidazole etc.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be high and the exposure time tends to be shortened, so the productivity of the color filter is improved.

＜Polymerization initiating aid (D1)＞

The colored resin composition of the present invention may contain a polymerization initiator auxiliary agent (D1). The polymerization initiation auxiliary agent (D1) is a compound or sensitizer for accelerating the polymerization of a polymerizable compound that is polymerized by a polymerization initiator.

Examples of the polymerization initiation aid (D1) include 4,4'-bis(dimethylamino)benzophenone (commonly known as Michelone) and 4,4'-bis(diethylamine). Benzophenone, 9,10-dimethoxyanthracene, 2,4-diethyl thioxanthone (2,4-diethyl thioxanthone), N-phenylglycine, etc.

When these polymerization initiating aids (D1) are used, the content is preferably 0.1 to 30 parts by mass, more preferably 1 to 100 parts by mass based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). 20 parts by mass. If the content of the polymerization initiation assistant (D1) is within the above range, a color filter can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.

＜Solvent (E)＞

The colored resin composition preferably contains a solvent (E). The solvent (E) is not particularly limited, and solvents commonly used in this field can be used. For example, ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents containing -COO- in the molecule), ether ester solvents (solvents containing -O- in the molecule), -COO- and -O-), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH but not -O-, -CO- and -COO in the molecule) - solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl styrene, etc.

Examples of solvents include: Ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate and Ester solvents such as γ-butyrolactone (solvents containing -COO- but not -O- in the molecule); Ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, diethylene glycol methyl ether Ether solvents such as base ethers (solvents containing -O- but not -COO- in the molecule); Methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate , ether ester solvents such as diethylene glycol monoethyl ether acetate (solvents containing -COO- and -O- in the molecule); 4-Hydroxy-4-methyl-2-pentanone (diacetone alcohol), heptanone, 4-methyl-2-pentanone, cyclohexanone and other ketone solvents (the molecule contains -CO- but does not contain -COO - solvent); Alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents that contain OH in the molecule but do not contain -O-, -CO-, and -COO-); Amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone; etc.

As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol) and ethyl lactate are more preferred.

When the solvent (E) is included, the content rate of the solvent (E) in the total amount of the colored resin composition of the present invention is preferably 60 to 95 mass%, more preferably 65 to 92 mass%. In other words, the total amount of solid content of the colored resin composition is preferably 5 to 40 mass %, more preferably 8 to 35 mass %, based on the total amount of the colored resin composition of the present invention. If the content rate of the solvent (E) is within the above range, the flatness during coating becomes good and the color density will not be insufficient when forming the color filter, so the display characteristics tend to be improved.

＜Leveling agent(F)＞

The colored resin composition may contain a leveling agent (F). Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, silicone surfactants having fluorine atoms, and the like. These side chains may have polymerizable groups.

Examples of organosilicone surfactants include surfactants having a siloxane bond in the molecule. Specific examples include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, and Toray Silicone SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.) ; KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Industry Co., Ltd.); TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Advanced Materials Japan) wait.

Examples of the above-mentioned fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Co., Ltd.); Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS-718-K (manufactured by DIC Co., Ltd.); Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.); Surflon (Registered Trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.), etc.

Examples of the above-mentioned organosilicon-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples include Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, and Megafac F443 (manufactured by DIC Co., Ltd.).

When the leveling agent (F) is included, the content rate of the leveling agent (F) in the total amount of the colored resin composition is preferably 0.001 to 0.2 mass %, more preferably 0.002 to 0.1 mass %. In addition, this content rate does not include the content rate of a pigment dispersant. If the content rate of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

＜Other ingredients＞

The colored resin composition of the present invention may contain additives commonly known in this technical field such as fillers, polymer compounds, adhesion accelerators, antioxidants, light stabilizers, chain transfer agents, etc., if necessary.

<Production method of colored resin composition>

The colored resin composition of the present invention can be obtained by combining a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and if necessary, a polymerization initiating assistant (D1), a solvent ( E), leveling agent (F) are mixed with other ingredients to prepare.

＜Manufacturing method of color filter＞

Examples of a method for producing a colored pattern (color filter) from the colored resin composition of the present invention include a photolithography method, an inkjet method, a printing method, and the like. Among them, photolithography is preferred.

In order to correct the height difference between pixels and improve flatness, the color filter may be laminated with an outer coating layer. As the curable composition for the outer coating layer, a conventional binder resin can be used.

By containing the triarylmethane lake and the anthraquinone compound (A1) in the colored resin composition, the color filter produced from the colored resin composition has excellent light resistance and heat resistance, and also has excellent heat resistance when an outer coating layer is laminated. Also excellent. This color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL (electroluminescence) devices, electronic paper, etc.) and solid-state imaging elements.

[Example]

The present invention will be described in more detail below with reference to examples. Of course, the present invention is not limited to the following examples and can be implemented with appropriate changes within the scope that satisfies the gist of the context. These are all included in the technical scope of the present invention. In addition, unless otherwise stated below, "part" means "mass part" and "%" means "mass %".

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

[Synthesis example 1]

The following reactions were carried out under nitrogen atmosphere. 50 parts of the compound represented by the formula (CI-2) and 188 parts of N,N-dimethylformamide were put into a flask equipped with a condenser and a stirring device, and the mixture was stirred for 30 minutes while cooling in an ice bath. 40 parts of tertiary potassium butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) was put into the flask, and the mixture was further stirred for 1 hour while cooling in an ice bath. While keeping the reaction mixture ice-cooled, 55.6 parts of ethyl iodide (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise. The reaction mixture was heated to 35°C using an oil bath and stirred for 5 hours, then allowed to cool to room temperature. 1000 parts of 10% sodium chloride aqueous solution was put into another flask equipped with a stirring device, and the above reaction mixture was added dropwise while stirring. After stirring for 30 minutes, the solid was obtained by filtration. The obtained solid was washed three times with 500 parts of ion-exchange water and dried at 60° C. under reduced pressure to obtain 53.0 parts of the compound represented by formula (CI-3). The yield is 93.5%.

The following reactions were carried out under nitrogen atmosphere. After putting 26.4 parts of potassium thiocyanate and 156 parts of acetonitrile into a flask equipped with a condenser tube and a stirring device, the mixture was stirred at room temperature for 30 minutes. 40.0 parts of 2,6-difluorobenzoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise to the above-mentioned flask over 30 minutes, and the mixture was stirred at room temperature for 1 hour. After adding dropwise 30.6 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) to the above-mentioned flask over 30 minutes, the mixture was stirred at room temperature for 1 hour. Into the above-mentioned flask, an aqueous solution in which 79.2 parts of sodium monochloroacetate was dissolved in 120 parts of ion-exchanged water was added, and after 60.4 parts of a 30% sodium hydroxide aqueous solution was added, the mixture was stirred at room temperature for 18 hours. Further 600 parts of ion-exchange water was added to the above flask, followed by stirring for 1 hour, and the precipitated yellow-white solid was filtered. The obtained yellow-white solid was washed with 120 parts of acetonitrile and then washed with 560 parts of ion-exchange water. The washed yellow-white solid, 156 parts of ion-exchange water, 35.0 parts of 99% acetic acid (manufactured by Wako Pure Chemical Industries, Ltd.) and 156 parts of toluene were put into a flask equipped with a stirring device, and stirred at room temperature for 2 hours. 80.8 parts of a 30% sodium hydroxide aqueous solution was added dropwise over 10 minutes, stirred for 5 minutes, and the water layer was removed through a liquid separation operation. After adding 156 parts of ion-exchange water to the obtained organic layer for liquid separation and washing, 156 parts of ion-exchange water and 0.1 part of 35% hydrochloric acid were added for liquid separation and washing. The obtained organic layer was concentrated with an evaporator and dried under reduced pressure at 35° C. to obtain a compound represented by formula (BI-3) as a white solid. The yield was 43.4 parts and the yield was 58.0%.

The following reactions were carried out under nitrogen atmosphere. 13.2 parts of the compound represented by the formula (BI-3), 19.0 parts of the compound represented by the formula (CI-3) and 38 parts of toluene were put into a flask equipped with a condenser tube and a stirring device, and then 9.2 parts of phosphorus oxychloride were added Stir at 100°C for 7 hours. Then, the reaction mixture was cooled to room temperature and diluted with 29 parts of methyl ethyl ketone. Next, a mixed solution of 114 parts of ion-exchange water and 10 parts of 35% hydrochloric acid aqueous solution was injected into the diluted reaction mixture, and the water layer was removed through a liquid separation operation. The obtained organic layer was subjected to solvent distillation using an evaporator and then dried at 60° C. under reduced pressure to obtain a compound represented by formula (X-II-7) as a blue-violet solid. The yield of blue-violet solid was 39.4 parts.

The following reactions were carried out under nitrogen atmosphere. 38.4 parts of the compound represented by formula (X-II-7) and 112 parts of dichloromethane were put into a flask equipped with a condenser tube and a stirring device, and stirred for 30 minutes. The reaction mixture was ice-cooled and 31.6 parts of chlorosulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) was added while maintaining the internal temperature at 10° C., and then the reaction mixture was heated to room temperature and stirred for 9 hours. Next, the reaction mixture was ice-cooled and diluted with a mixed solution of 64 parts of N,N-dimethylformamide and 4.9 parts of ion-exchange water while maintaining the internal temperature at 10°C. When the diluted reaction mixture is poured into 1120 parts of toluene and stirred for 30 minutes, a viscous solid will precipitate. After the oil layer was discharged by decantation, 320 parts of toluene was added to the obtained viscous solid and stirred for 30 minutes. To the viscous solid obtained by draining the oil layer by decantation, 832 parts of 20% salt water was added and stirred for 1 hour, and then the blue solid was filtered out by filtration. The obtained blue solid was washed with 576 parts of 20% saline water and dried under reduced pressure at 35°C. The obtained solid and 128 parts of methanol were put into a flask equipped with a stirring device, and the mixture was stirred for 30 minutes, and then filtered to separate the solid and the filtrate. This filtrate was called Filtrate I. The filtered solid was washed with 192 parts of methanol, and separated into a solid and a filtrate by filtration. This filtrate was called filtrate II. Filtrate I and filtrate II were mixed, and the solvent was removed using an evaporator, and then dried under reduced pressure at 40° C. to obtain the compound represented by formula (XI-7) as a blue-violet solid. The yield of blue-violet solid was 38.3 parts.

28.0 parts of the compound represented by formula (XI-7), 43.2 parts of barium chloride dihydrate and 356 parts of ion-exchange water were added to a flask equipped with a condenser tube and a stirring device, and the reaction was stirred at 40°C for 2 hours. The mixture is filtered. 350 parts of the filtered solid and ion-exchange water were put into a flask equipped with a stirring device, and the mixture was stirred for 30 minutes, and then the suspension was filtered. The obtained solid was washed with 280 parts of ion-exchange water and dried under reduced pressure at 60° C. to obtain a compound represented by formula (A3-7) as a blue-violet solid. The yield was 24.5 parts and the yield was 81.7%. Identification (mass analysis) of the compound represented by formula (A3-7) Ionization mode = ESI +: m/z = 949.5 [M-Ba + 2H] ⁺ accurate mass (Exact Mass) [M-Ba]: 947.28

[Synthesis example 2]

The following reactions were carried out under nitrogen atmosphere. After putting 32.2 parts of potassium thiocyanate and 160 parts of acetone into a flask equipped with a condenser tube and a stirring device, the mixture was stirred at room temperature for 30 minutes. Next, 50.0 parts of 2-fluorobenzoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over 10 minutes. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours. Next, after the reaction mixture was ice-cooled, 40.5 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise. After completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes. Next, after the reaction mixture was ice-cooled, 34.2 parts of a 30% sodium hydroxide aqueous solution was added dropwise. After completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes. Next, 31.3 parts of chloroacetic acid was added dropwise at room temperature. After completion of the dropwise addition, the mixture was stirred under heating and reflux for 7 hours. Next, the reaction mixture was left to cool to room temperature, and then the reaction mixture was poured into 120.0 parts of ion-exchange water, and then 200 parts of toluene was added and stirred for 30 minutes. Then stop stirring, let it stand for 30 minutes, and then separate into an organic layer and an aqueous layer. After the aqueous layer was removed by liquid separation, the organic layer was washed with 200 parts of 1N hydrochloric acid, then with 200 parts of ion-exchange water, and finally with 200 parts of saturated brine. An appropriate amount of Glauber's salt was added to the organic layer and stirred for 30 minutes, and then filtered to obtain a dry organic layer. The obtained organic layer was subjected to solvent distillation using an evaporator to obtain a pale yellow liquid. The obtained pale yellow liquid was purified by column chromatography. The purified light yellow liquid was dried under reduced pressure at 60°C to obtain 49.9 parts of the compound represented by formula (B-II). The yield is 51%.

The following reactions were carried out under nitrogen atmosphere. After placing 15.3 parts of N-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 60 parts of N,N-dimethylformamide into a flask equipped with a condenser tube and a stirring device, the mixed solution was ice-cooled. After adding 5.7 parts of 60% sodium hydride (manufactured by Tokyo Chemical Industry Co., Ltd.) little by little over 30 minutes under ice-cooling, the mixture was stirred for 1 hour while raising the temperature to room temperature. Next, 10.4 parts of 4,4'-difluorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) was added little by little to the reaction mixture, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was added little by little to 200 parts of ice water, and then left to stand at room temperature for 15 hours. The water was removed by decantation to obtain a viscous solid as a residue. After adding 60 parts of methanol to the viscous solid, the mixture was stirred at room temperature for 15 hours. The precipitated solid was filtered out and purified by column chromatography. The purified light yellow solid was dried under reduced pressure at 60°C to obtain 9.8 parts of the compound represented by formula (C-II). The yield is 53%.

The following reactions were carried out under nitrogen atmosphere. After putting 8.2 parts of the compound represented by the formula (B-II), 10.0 parts of the compound represented by the formula (C-II) and 20.0 parts of toluene into a flask equipped with a condenser tube and a stirring device, 12.2 parts of phosphorus oxychloride was added. Stir at 95 to 100°C for 3 hours. Next, the reaction mixture was cooled to room temperature and then diluted with 170.0 parts of isopropyl alcohol. Next, the diluted reaction mixture was poured into 300.0 parts of saturated brine, and then 100 parts of toluene was added and stirred for 30 minutes. Stop stirring and let stand for 30 minutes, then separate into organic layer and aqueous layer. After the aqueous layer was removed by liquid separation, the organic layer was washed with 300 parts of saturated brine. An appropriate amount of Glauber's salt was added to the organic layer and stirred for 30 minutes, and then filtered to obtain a dry organic layer. The obtained organic layer was subjected to solvent distillation using an evaporator to obtain a blue-violet solid. The blue-purple solid was further dried at 60°C under reduced pressure to obtain 18.4 parts of a compound represented by formula (YI-41). The yield is 100%. Identification (mass analysis) of the compound represented by formula (YI-41) Ionization mode = ESI +: m/z = 687.3 [M-Cl] ⁺ accurate mass (Exact Mass): 722.3

The following reactions were carried out under nitrogen atmosphere. After putting 8.0 parts of the compound represented by Formula (Y-I-41) and 396.0 parts of methanol into a flask equipped with a condenser tube and a stirring device, the mixture was stirred at room temperature for 30 minutes to prepare a blue solution. Next, 396.0 parts of ion-exchange water was added to the blue solution, and the mixture was further stirred at room temperature for 30 minutes to obtain a reaction mixture.

53 parts of ion-exchanged water was put into a beaker, and 11.8 parts of Keggin-type phosphotungstic acid (manufactured by Aldrich) and 53 parts of methanol were put into the ion-exchanged water, and mixed at room temperature in an air atmosphere. Prepare phosphotungstic acid solution.

The obtained phosphotungstic acid solution was added dropwise to the previously prepared reaction mixture over 1 hour. After further stirring at room temperature for 30 minutes, the mixture was filtered to obtain a blue solid. The obtained blue solid was added to 200.0 parts of methanol and dispersed for 1 hour, and then the filtration operation was repeated twice. The blue solid obtained by this operation was put into 200.0 parts of ion-exchange water and dispersed for 1 hour, and then the filtration operation was repeated twice. The blue solid obtained by this operation was dried under reduced pressure at 60° C. to obtain 17.1 parts of the compound represented by formula (A2-41). The yield is 94%.

[Synthesis example 3]

Add 66.9 parts of chlorosulfonic acid to a flask equipped with a condenser and a stirring device, cool it to below 10°C, and slowly add CI Solvent Blue 104 (compound represented by formula (A1Y-1)) 3.6 while stirring. share. Then, the reaction mixture was allowed to warm to room temperature (25°C) on its own and stirred at the same temperature for 6 hours. The obtained reaction mixture was added dropwise to 108 parts of ice water to prepare a suspension. The precipitated crystals were filtered out, washed carefully with ion-exchange water, and dried under reduced pressure at 60°C overnight to obtain formula (A1Y-2 4.9 parts of crude product of the compound represented by ). This was purified by silica gel column chromatography (solvent: chloroform) to obtain 3.4 parts of the compound represented by formula (A1Y-2).

In a flask equipped with a condenser tube and a stirring device, add 4.6 parts of 3-amino-4-methylbenzoic acid methyl ester and 16.5 parts of chloroform, cool to below 10°C, and add formula (A1Y- 2) A solution of 2.4 parts of the indicated compound dissolved in 16.5 parts of chloroform and 2.2 parts of pyridine. Then, the reaction mixture was allowed to warm to room temperature on its own and stirred at the same temperature for 5 hours. To the obtained reaction mixture were added 150 parts of chloroform and 50 parts of 2N hydrochloric acid for liquid separation, and the organic layer was washed twice with 50 parts of 2N hydrochloric acid. The obtained organic layer was dried over excess sodium sulfate, and chloroform was distilled off under reduced pressure from the filtered solution to obtain 3.4 parts of a crude product of the compound represented by formula (A1Y-3). This was purified by silica gel column chromatography (solvent: chloroform) to obtain 2.8 parts of the compound represented by formula (A1Y-3). Identification (mass analysis) of the compound represented by formula (A1Y-3) Ionization mode = ESI +: m/z = 929.2 [M + H] ⁺ accurate mass (Exact Mass): 928.3

In a flask equipped with a condenser and a stirring device, add 2.5 parts of the compound represented by formula (A1Y-3), 35 parts of N-methylpyrrolidone and 17 parts of 8% sodium hydroxide aqueous solution, and stir at 50°C for 5 hours. After leaving to cool, the obtained reaction mixture was added to 175 parts of 2N hydrochloric acid to prepare a suspension. The precipitated crystals were filtered out, washed carefully with ion-exchange water, and dried under reduced pressure at 60°C overnight to obtain the formula ( 2.1 parts of the compound represented by A1X-36). Identification (mass analysis) of the compound represented by formula (A1X-36) Ionization mode = ESI +: m/z = 901.2 [M + H] ⁺ accurate mass (Exact Mass): 900.3

[Synthesis example 4]

Into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was introduced to replace it with a nitrogen atmosphere, and 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added and heated to 85°C while stirring. . Next, the following mixed solution was added dropwise over 5 hours: 38 parts of acrylic acid, acrylic acid-3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decan-8-yl ester and acrylic acid-3,4-epoxy 25 parts of a mixture of tricyclic [5.2.1.0 ^2,6 ] decane-9-yl ester (containing ratio in molar ratio is 1:1), 137 parts of N-cyclohexylmaleimide, 2-hydroxy 50 parts of ethyl methacrylate and 338 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition, the mixture was kept at 85°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin) with a viscosity of 23 mPas and a solid content of 25.6% measured by a B-type viscometer (23°C). B1) solution. The weight average molecular weight Mw of the produced copolymer was 8.0×10 ³ , the dispersion degree was 2.1, and the acid value in terms of solid content was 111 mg-KOH/g. Resin B1 has the following structural units. The weight average molecular weight (Mw) and number average molecular weight (Mn) of the above-mentioned resin were measured using the GPC method under the following conditions. Device: K2479 (manufactured by Shimadzu Corporation) Column: SHIMADZU Shim-pack GPC-80M Column temperature: 40°C Solvent: THF (tetrahydrofuran) Test solution concentration: 25 mg/mL (mg/mL) (solvent : THF) Flow rate: 1.0 mL/min (ml/min) Detector: RI Standard material for calibration: TSK STANDARD POLYSTYRENE (standard polystyrene) F-40, F-4, F-288, A-2500, A- 500 (manufactured by Tosoh Co., Ltd.) The ratio of the polystyrene-converted weight average molecular weight and the number average molecular weight obtained above was defined as the degree of dispersion (Mw/Mn).

[Example 1]

<Preparation of colored resin composition 1> Mixed (A) coloring agent: 21 parts of the compound represented by formula (A3-7) 9 parts acrylic pigment dispersant Propylene glycol monomethyl ether acetate 264 parts, Use a bead mill to fully disperse the compound represented by formula (A3-7), and then, Mixing (A) Colorant: 5 parts of the compound represented by formula (A1X-36) (B) Resin: 50 parts of resin B1 (solid content conversion) (C) Polymerizable compound: dipenterythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylhydrothiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01; BASF Corporation Manufacturing) 7 servings (F) Leveling agent: polyether modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 517 parts of propylene glycol monomethyl ether acetate (E) Solvent: 23 parts of ethyl lactate Thus, colored resin composition 1 was obtained.

[Example 2]

<Preparation of colored resin composition 2> Mixed (A) coloring agent: 11 parts of the compound represented by formula (A2-41) 4 parts acrylic pigment dispersant Propylene glycol monomethyl ether acetate 129 parts 5 parts of diacetone alcohol, Use a bead mill to fully disperse the compound represented by formula (A2-41), and then Mixing (A) Colorant: 5 parts of the compound represented by formula (A1X-36) (B) Resin: Resin B1 (solid content conversion) 50 parts (C) Polymerizable compound: 50 parts of dipenterythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) (D) Polymerization initiator: N-benzyloxy-1-(4-phenylhydrothiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE　01; BASF Corporation Manufacturing) 7 servings (F) Leveling agent: polyether modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 674 parts of propylene glycol monomethyl ether acetate (E) Solvent: 26 parts of ethyl lactate Thus, colored resin composition 2 was obtained.

[Comparative example 1]

<Preparation of colored resin composition 3> Mixing (A) Colorant: 20 parts of the compound represented by formula (A3-7) 8 parts of acrylic pigment dispersant Propylene glycol monomethyl ether acetate 252 parts, Use a bead mill to fully disperse the compound represented by formula (A3-7), and then, Mixing (B) Resin: Resin B1 (solid content conversion) 50 parts (C) Polymerizable compound: dipenterythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzyloxy-1-(4-phenylhydrothiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE01; manufactured by BASF Corporation ) 7 copies (F) Leveling agent: polyether modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 493 parts of propylene glycol monomethyl ether acetate (E) Solvent: 23 parts of ethyl lactate Thus, colored resin composition 3 was obtained.

＜Creation of color filters (coloring patterns)＞

The colored resin composition was coated on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Corporation) by spin coating, and then prebaked at 100° C. for 3 minutes to obtain a colored resin composition layer. After leaving to cool, the distance between the substrate on which the colored resin composition layer was formed and the quartz glass photomask was set to 100 microns, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used to expose the substrate in the atmosphere. Light irradiation was carried out under an atmosphere with an exposure amount of 150 mJ/cm ² (millijoules/cm2) (365 nm standard). As the photomask, a photomask formed with a 100-micron line and space pattern was used. The colored resin composition layer after light irradiation was immersed and developed in an aqueous developer containing 0.12% nonionic surfactant and 0.04% potassium hydroxide at 24°C for 60 seconds. After washing with water, it was dried in an oven at 230° C is post-baked for 20 minutes to obtain a color filter.

＜Film thickness measurement＞

The film thickness of the obtained color filter was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.).

＜Color evaluation＞

For the obtained color filter, the spectrometry was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.), and the xy chromaticity in the CIE XYZ colorimetric system was measured using the characteristic function of the C light source. Coordinates (x, y) and stimulus value Y. The larger the Y value, the higher the brightness.

＜Evaluation of light resistance＞

An ultraviolet cutoff filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co., Ltd.; cuts light below 380 nm) was placed on the obtained color filter, and a light resistance testing machine (SUNTEST GPS+; Toyo Seiki Co., Ltd. Co., Ltd.) irradiated with xenon light for 48 hours.

The xy chromaticity coordinates (x, y) and Y are measured before and after irradiation, and the color difference A is calculated from the measured values using the method described in JIS Z 8730:2009 (7. Calculation method of color difference) (the color difference A is before and after light irradiation) △E*ab), the results are shown in Table 5. The smaller the color difference A, the smaller the color change. [table 5]

<Preparation of curable composition for outer coating>

60 parts of styrene/methacrylic acid/glycidyl methacrylate copolymer (mass ratio: 30/20/50; synthesized by the method described in Japanese Patent Application Laid-Open No. 11-133600; molecular weight: 21,000) , 40 parts of dipenterythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.), 2-methyl-2-morpholin-1-(4-methylhydrothio) Mix 6 parts of phenyl)propan-1-one (IRGACURE (registered trademark) 907; manufactured by BASF Corporation) and 197 parts of diethylene glycol dimethyl ether to prepare a curable composition for an outer coating.

<Evaluation of heat resistance of laminated films>

On the obtained color filter, the above-mentioned curable composition for the outer coating layer was applied by the spin coating method so that the film thickness after drying became 1.5 μm, and then prebaked in a clean oven at 100°C for 3 minutes. Bake and post-bake at 230°C for 20 minutes to prepare a laminated film. The laminated film was heated in a clean oven at 230°C for 2 hours, and the xy chromaticity coordinates (x, y) and Y measured values before and after heating were determined according to JIS Z 8730:2009 (7. Calculation method of color difference). The color difference B was calculated using the method (the color difference B is ΔE*ab before and after heating in the laminated film state), and the improvement rate was further calculated. The results are shown in Table 6. In addition, in the present invention, the improvement rate refers to the degree of improvement in the heat resistance of the colored resin composition in the laminated film state relative to the colored resin composition 3 of Comparative Example 1. That is, the improvement rate is represented by the following formula (i). [Formula (i)] Improvement rate (%) = (Color difference B of Comparative Example 1/Color difference B of Example) × 100 The larger the value of the improvement rate, the smaller the color change. [Table 6]

Industrial availability

According to the colored resin composition of the present invention, it is possible to form a color filter having excellent light resistance, heat resistance, and heat resistance in a state in which an outer coating layer is laminated. This color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging elements.

without

without

Claims (3)

A colored resin composition containing a colorant, a resin, a polymerizable compound and a polymerization initiator, wherein the colorant contains a triarylmethane lake and a compound represented by formula (A1),

In the formula (A1), A ^1a and A ^2a each independently represent a phenylene group which may have a substituent; L ^1a and L ^2a each independently represent a divalent hydrocarbon group having 1 to 12 carbon atoms, and the hydrocarbon group contains -CH ₂ - can be replaced by -O-, -SO ₂ - or -NR ^11a -; R ^1a to R ^6a each independently represents a hydrogen atom, a halogen atom or an alkyl group with 1 to 8 carbon atoms; R ^11a represents hydrogen atom or an alkyl group having 1 to 8 carbon atoms; wherein the triarylmethane lake is at least one selected from the group consisting of a compound represented by formula (A2) and a compound represented by formula (A3),

In the formula (A2), R ^11b to R ^14b each independently represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or a hydrocarbon group which may have a substituent. Aralkyl group with 7 to 30 carbon atoms. In the saturated hydrocarbon group with 1 to 20 carbon atoms, the hydrogen atoms contained in the saturated hydrocarbon group may be replaced by substituted or unsubstituted amine groups or halogen atoms. When the saturated hydrocarbon group is When the carbon number of the saturated hydrocarbon group is 2 to 20, the -CH ₂ - contained in the saturated hydrocarbon group can be replaced by -O- or -CO-; however, in the saturated hydrocarbon group with 2 to 20 carbon atoms, adjacent -CH ₂ - will not be replaced by -O- at the same time; R ^11b and R ^12b can bond and form a ring together with the nitrogen atoms to which they are bonded, and R ^13b and R ^14b can bond to form a ring with the nitrogen atoms to which they are bonded. Nitrogen atoms together form a ring; R ^17b to R ^24b each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, and an alkyl group with 1 to 8 carbon atoms. -CH ₂ - constituting the alkyl group may be replaced by -O- Or -CO- substitution; R ^18b and R ^22b can be bonded to each other to form -NH-, -O-, -S- or -SO ₂ -; Ring T ^1b represents a carbon number of 3 to 10 that may have a substituent. An aromatic heterocyclic ring or an aromatic hydrocarbon ring with 6 to 10 carbon atoms that may have a substituent; [Y] ^m- represents at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus, and Any m-valent anion of oxygen; m represents any natural number; in addition, when a molecule contains multiple structures represented by the following formulas, they can be the same or different structures,

In the formula, ring T ^1b , R ^11b to R ^14b and R ^17b to R ^24b are each synonymous with the above;

In formula (A3), R ^41b to R ^44b each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or may have a substituent. an aralkyl group with 7 to 30 carbon atoms. The aromatic hydrocarbon group and the substituent that the aralkyl group may have may be -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . The saturated hydrocarbon group The hydrogen atoms contained can be replaced by substituted or unsubstituted amino groups or halogen atoms. When the number of carbon atoms of the saturated hydrocarbon group is 2 to 20, the -CH ₂ - contained in the saturated hydrocarbon group can be replaced by -O- Or -CO- replacement; however, in the saturated hydrocarbon group with 2 to 20 carbon atoms, the adjacent -CH ₂ - will not be replaced by -O- at the same time; R ^41b and R ^42b can be bonded to them. The bonded nitrogen atoms form a ring together, and R ^43b and R ^44b can be bonded to form a ring together with the nitrogen atoms to which they are bonded; R ^47b to R ^54b each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, - SO ₃ ^- , -SO ₂ -N ^- -SO ₂ -R ^f , or an alkyl group with 1 to 8 carbon atoms, and -CH ₂ - constituting the alkyl group can be replaced by -O- or -CO-; R ^48b and R ^52b can bond with each other to form -NH-, -S-, or -SO ₂ -; however, in the alkyl group, the adjacent -CH ₂ - will not be replaced by -O- at the same time; Ring T ^2b represents an aromatic heterocyclic ring with 3 to 10 carbon atoms or an aromatic hydrocarbon ring with 6 to 10 carbon atoms. The aromatic heterocyclic ring and the aromatic hydrocarbon ring may have a saturated hydrocarbon group with 1 to 20 carbon atoms. A substituted or unsubstituted amino group or an aromatic hydrocarbon group with 6 to 20 carbon atoms that may have a substituent; the substituent that the aromatic hydrocarbon group may have may be -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f , M ^r+ represents a metal ion with r valence; k represents the number of -SO ₃ ^- and -SO ₂ -N ^- -SO contained in R ^41b to R ^44b , R ^47b to R ^54b and ring T ^2b . ₂ - The sum of the numbers of ^{R f} ; r represents an integer above 1; R ^f represents a fluoroalkyl group with 1 to 12 carbon atoms; wherein, R ^41b to R ^44b , R ^47b to R ^54b and ring T ^2b have at least a -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f ; in addition, when a molecule contains multiple structures represented by the following formulas, they can be the same or different structures,

In the formula, each of ring T ^2b , R ^41b to R ^44b and R ^47b to R ^54b has the same meaning as above. A color filter formed from the colored resin composition according to claim 1. A display device including the color filter described in claim 2.