Curable composition for color filters, color filters, display devices, and solid-state imaging devices

Abstract

To provide a curable composition useful for producing a color filter that makes the pattern shape good.SOLUTION: A curable composition according to the present invention contains a resin, a polymerizable compound and a polymerization initiator, and is characterized in that the polymerizable compound contains at least one selected from the group consisting of hexitol poly(meth)acrylate and polyglycerin poly(meth)acrylate.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a curable composition, a color filter, a display device, and a solid-state imaging device. [Background technology]

[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state imaging devices such as CCD and CMOS sensors, are produced from curable compositions. Dipentaerythritol hexaacrylate modified with ethylene oxide is known as a polymerizable compound used in the curable compositions for forming the color filters (Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2008-164886 Summary of the Invention [Problem to be solved by the invention]

[0004] However, patterns formed from a curable composition containing dipentaerythritol hexaacrylate modified with ethylene oxide often had unsatisfactory pattern shapes, such as a rounded top shape and a trailing bottom shape.

[0005] An object of the present invention is to provide a curable composition that is useful for producing a color filter with a good pattern shape. [Means for solving the problem]

[0006] That is, the gist of the present invention is as follows. [1] A composition comprising a resin, a polymerizable compound, and a polymerization initiator; The curable composition, wherein the polymerizable compound comprises at least one selected from the group consisting of hexitol poly(meth)acrylate and polyglycerin poly(meth)acrylate. [2] The curable composition according to [1], wherein the hexitol poly(meth)acrylate is a compound represented by the following formula (CA): [ka] [In formula (CA), Y represents a hydrogen atom or a (meth)acryloyl group, and the number of (meth)acryloyl groups contained in formula (CA) is 1 or more and 6 or less. a to f each independently represent the number of -O-CH2-CH2- units, and a+b+c+d+e+f is 0 or more and 24 or less. [3] The curable composition according to [2], wherein in formula (CA), a+b+c+d+e+f is 3 or more and 21 or less. [4] The curable composition according to any one of [1] to [3], wherein the polyglycerin poly(meth)acrylate is a compound represented by the following formula (CB): [ka] [In formula (CB), Z represents a hydrogen atom or a (meth)acryloyl group, and the number of (meth)acryloyl groups contained in formula (CB) is 1 or more and (n+2) or less. g to i each independently represent the number of -O-CH2-CH2- units and are integers of 0 or more and 5 or less. n represents the degree of polymerization of glycerin and is an integer of 2 or more and 20 or less. [5] The curable composition according to [4], wherein in formula (CB), g to i each independently represent 1 or more and 3 or less. [6] The curable composition according to any one of [1] to [5], wherein the resin is an alkali-soluble resin. [7] The curable composition according to any one of [1] to [6], wherein the resin has a structural unit containing a (meth)acryloyl group in a side chain. [8] The curable composition according to any one of [1] to [7], wherein the polymerization initiator comprises an O-acyloxime compound. [9] A color filter formed from the curable composition according to any one of [1] to [8].

[10] A display device comprising the color filter according to [9].

[11] A solid-state imaging device comprising the color filter according to [9]. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a curable composition that is useful for producing a color filter with a good pattern shape. [Brief explanation of the drawings]

[0008] [Figure 1] FIG. 1 is a schematic side view of a colored pattern obtained from a colored curable resin composition of an example or a comparative example. DETAILED DESCRIPTION OF THE INVENTION

[0009] The curable composition of the present invention contains a resin (hereinafter may be referred to as resin (B)), a polymerizable compound (hereinafter may be referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter may be referred to as polymerization initiator (D)). The polymerizable compound (C) contains at least one selected from the group consisting of hexitol poly(meth)acrylates and polyglycerin poly(meth)acrylates. The curable composition of the present invention may contain a colorant (hereinafter, may be referred to as colorant (A)). The curable composition of the present invention may contain an organic solvent (hereinafter, may be referred to as organic solvent (E)). The curable composition of the present invention may contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as components can be used alone or in combination unless otherwise specified.

[0010] <Colorant (A)> The colorant (A) is not particularly limited and may be a known dye and / or pigment. The colorant (A) preferably contains one or more selected from the group consisting of the compound (I) described below, the compound (II) described below, CI Pigment Yellow 138, CI Pigment Yellow 150, CI Pigment Yellow 185, CI Pigment Yellow 231, CI Pigment Yellow 233, CI Pigment Blue 16, CI Pigment Green 58, CI Pigment Green 59, CI Pigment Green 62, CI Pigment Green 63, CI Pigment Red 242, CI Pigment Red 254, CI Pigment Red 269, CI Pigment Violet 19, and CI Pigment Violet 23 (hereinafter, these colorants may be collectively referred to as colorant (A2)). The colorant (A) more preferably contains the compound (I) described below and the compound (II) described below, and even more preferably contains the compound (I).

[0011] <<Compound (I)>> The colorant (A) may contain a phthalocyanine containing a central metal (e.g., Cu or Al) which may have a substituent, and preferably contains a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)).

[0012] [ka]

[0013] [In formula (I), X represents a hydrogen atom or a monovalent metal atom. R 1 represents a substituted or unsubstituted amino group or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. n represents an integer of 0 to 4. m represents an integer of 0 to 4. When formula (I) has a plurality of Xs, Xs may be the same or different from each other, and when formula (I) has a plurality of R 1 If R 1 may be the same as or different from each other.]

[0014] Compound (I) is a compound represented by the following formula (I-0), in which (n+m) hydrogen atoms are arranged in the form of n -SO3X and m -SO2R 1 represents a compound substituted with

[0015] [ka]

[0016] n is preferably an integer of 0 to 3, m is preferably an integer of 0 to 3, and the sum of the integers represented by n and m is preferably 0 to 4, more preferably 0 to 3.

[0017] Examples of the monovalent metal atom represented by X include alkali metal atoms such as Na, K, and Li. X is preferably any one of a hydrogen atom, Na, K, and Li, and more preferably a hydrogen atom or Na.

[0018] R 1 Examples of the substituted or unsubstituted amino group represented by the formula (I) include an amino group; and an amino group having one or two hydrocarbon groups bonded thereto, such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-butylamino group, an N-pentylamino group, an N-hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-phenylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-(1-methyl)hexylamino group, an N-(2-methyl)hexylamino group, an N-(3-methyl)hexylamino group, an N-(4-methyl)hexylamino group, or an N-(5-methyl)hexylamino group (the hydrocarbon group preferably has 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms; -CH- contained in the hydrocarbon group may be replaced with -O-).

[0019] R 1Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0020] R 1 Examples of the saturated or unsaturated chain hydrocarbon group represented by the formula (I) include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, isohexyl, and (1-methyl)propyl; branched alkyl groups such as a (2-methyl)hexyl group, a (3-methyl)hexyl group, a (4-methyl)hexyl group, a (5-methyl)hexyl group, and a (3-ethyl)heptyl group; and alkenyl groups such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a (1-methyl)ethenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a (1-(2-propenyl))ethenyl group, a (1,2-dimethyl)propenyl group, and a 2-pentenyl group. The saturated or unsaturated chain hydrocarbon group preferably has 1 to 15 carbon atoms, more preferably 1 to 10, even more preferably 1 to 8, even more preferably 2 to 8, and even more preferably 3 to 8.

[0021] R 1Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by the formula (I) include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene and cyclohex-3-ene), cycloheptenyl, and cyclooctenyl; norbornyl, adamantyl, and bicyclo[2.2.2]octyl. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 15, even more preferably 4 to 15, still more preferably 4 to 12, and even more preferably 4 to 10.

[0022] R 1 Examples of the aromatic hydrocarbon group represented by the formula (I) include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, etc. The aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 18 carbon atoms, even more preferably 6 to 15 carbon atoms, and even more preferably 6 to 12 carbon atoms.

[0023] R 1The hydrocarbon group represented by the formula (I) may be a group obtained by combining two or more of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, as long as the upper limit of the number of carbon atoms is not more than 20. Such a group may be, for example, a group obtained by combining an aromatic hydrocarbon group with at least one group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group, and in such a hydrocarbon group obtained by combination, the chain hydrocarbon group may be combined as a divalent group (for example, an alkanediyl group). Examples of combined hydrocarbon groups include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylethenyl (phenylvinyl); arylalkynyl groups such as phenylethynyl; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2,5-diisopropylphenyl, and 2,6-diisopropylphenyl. alkylaryl groups such as phenyl, 2,4,6-triisopropylphenyl, and 4-butylphenyl; aryl groups to which an alkanediyl group is bonded such as 2,3-dihydro-4-indenyl, 1,2,3,5,6,7-hexahydro-4-s-indacenyl, 5,6,7,8-tetrahydro-1-naphthyl, and 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl; aryl groups to which one or more aryl groups are bonded such as biphenylyl and terphenylyl; cyclohexylmethylphenyl, benzylphenyl, and (dimethyl(phenyl)methyl)phenyl.The hydrocarbon group may be, for example, a hydrocarbon group formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples thereof include alicyclic hydrocarbon groups having one or more alkyl groups bonded thereto, such as a 1-methylcyclopropyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 2,4,6-trimethylcyclohexyl group, a 2,2,6,6-tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, or a 4-octylcyclohexyl group; and alkyl groups having one or more alicyclic hydrocarbon groups bonded thereto, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, or an adamantylmethyl group. The number of carbon atoms in the group formed by combining two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups is preferably 4 to 20, more preferably 6 to 18, even more preferably 6 to 15, and still more preferably 6 to 12.

[0024] R 1 The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is preferably an aliphatic hydrocarbon group, more preferably a saturated chain aliphatic hydrocarbon group, and even more preferably a saturated straight-chain aliphatic hydrocarbon group or a saturated branched-chain aliphatic hydrocarbon group.

[0025] R 1Examples of the substituent that the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have include a halogen atom; a nitrile group; a nitro group; an amino group; a hydroxy group; an alkoxy group having 1 to 15 carbon atoms, such as a methoxy group or an ethoxy group; an aryloxy group having 6 to 20 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group or a 2-naphthyloxy group; a silyl group; a boryl group; an alkylamino group having 1 to 15 carbon atoms, such as a monomethylamino group, a dimethylamino group, a monoethylamino group or a diethylamino group; and an arylamino group having 6 to 20 carbon atoms, such as a monophenylamino group or a diphenylamino group. aralkylamino groups having 7 to 20 carbon atoms, such as a benzylamino group; a carboxy group; a carbamoyl group; alkylcarbonyl groups having 2 to 15 carbon atoms, such as an acetyl group or a propionyl group; arylcarbonyl groups having 7 to 20 carbon atoms, such as a benzoyl group, a 1-naphthylcarbonyl group or a 2-naphthylcarbonyl group; alkoxycarbonyl groups having 2 to 15 carbon atoms, such as a methoxycarbonyl group or an ethoxycarbonyl group; and aryloxycarbonyl groups having 7 to 20 carbon atoms, such as a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group or a 2-naphthyloxycarbonyl group. R 1 The substituent that the hydrocarbon group having 1 to 20 carbon atoms represented by the following formula may have is preferably a halogen atom.

[0026] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a chlorine atom being preferred.

[0027] R 1 The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is preferably a hydrocarbon group having a substituent.

[0028] Examples of compound (I) include a compound represented by formula (I-x1) (hereinafter, sometimes referred to as compound (I-x1)). The numbers n, m1, and m2 are preferably 0 to 4, more preferably 0 to 2, even more preferably 0 or 1, and even more preferably 0. r is preferably 0 to 4, more preferably 0 to 2, even more preferably 0 or 1, and even more preferably 0. Examples of the compound represented by formula (I-x1) include Compounds 1 to 81, as shown in Table 1 below. Among Compounds 1 to 81, when the sum of the integer represented by n, the integer represented by m1, and the integer represented by m2 is 2 or more, -SO3X, -SO2NH2, and / or -SO2(CH2) r It is preferable that each Cl is bonded to a different benzene ring.

[0029] [ka]

[0030] [Table 1]

[0031] Among these, as Compound (I-x1), Compound 1, Compound 11, Compound 18, Compound 22, Compound 23, Compound 30, Compound 34, Compound 35, Compound 39, Compound 40, Compound 53, Compound 56, Compound 60, Compound 72, and Compound 81 are preferred, Compound 11, Compound 18, Compound 23, Compound 30, Compound 34, Compound 35, Compound 39, Compound 53, Compound 56, Compound 60, Compound 72, and Compound 81 are more preferred, and Compound 81 is even more preferred.

[0032] Specific examples of the compound (I-x1) include CI Pigment Blue 15:4, CI Direct Blue 86, CI Direct Blue 87, CI Direct Blue 199, and CI Reactive Blue 25. It is particularly preferable to include at least one dye selected from the group consisting of the above dyes. The compound (I-x1) is more preferably CI Pigment Blue 15:4.

[0033] The method for producing compound (I-x1) is not particularly limited, but it can also be produced by referring to the synthesis examples described in JP-A-2011-28236.

[0034] The compound (I-x1) is soluble in water and has a solubility parameter (SP value) of 11.0 (cal / cm) for propylene glycol monomethyl ether acetate or the like. 3 ) 1 / 2 Preferably, the polymer is poorly soluble in an organic solvent having a solubility of less than 1000 kJ / mol. 0.1 g of compound (I-x1) was placed in a 20 mL sample vial, and water or an organic solvent was added using a 10 mL volumetric pipette. The vial was then capped and ultrasonicated for 3 minutes. The resulting solution was then stored in a water bath at 23°C for 60 minutes. 5 mL of the supernatant was filtered through a PTFE 5 μm membrane filter and then through a 0.25 μm membrane filter to remove insoluble material. The absorption spectrum of the resulting filtrate was measured using a 1 cm cell on a UV-visible spectrophotometer (e.g., Shimadzu UV-2500PC) to determine the absorbance (abs) at the maximum absorption wavelength of compound (I-x1). If the absorbance (abs) was less than 40% of the upper limit of measurement (for Shimadzu UV-2500PC, the absorbance (abs) was less than 2), the compound was considered poorly soluble. If it was 40% or greater than the upper limit of measurement, the compound was considered soluble.

[0035] It is preferable to prepare a colored dispersion in advance in which the compound (I-x1) is uniformly dispersed in an organic solvent by adding a dispersant and dispersing the compound (I-x1). The colored dispersion may contain a part or all of the organic solvent (E) contained in the curable composition. The curable composition can be prepared using the colored dispersion.

[0036] Examples of dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more. Examples of dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLORENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Corporation), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK), and BYK (registered trademark) (manufactured by BYK). Resin (B) (preferably resin [K1]), which will be described later, may also be used as the dispersant.

[0037] When a dispersant is used, the amount of the dispersant (solid content) used is usually 1 to 500 parts by mass, preferably 5 to 300 parts by mass, more preferably 10 to 200 parts by mass, and even more preferably 15 to 180 parts by mass, relative to 100 parts by mass of compound (I-x1). When the amount of the dispersant used is within the above range, a colored dispersion liquid in a more uniformly dispersed state tends to be obtained.

[0038] The content of the compound (I-x1) in the total amount of the colorant (A) is preferably 1 to 100 mass%, more preferably 3 to 60 mass%, even more preferably 4 to 30 mass%, and even more preferably 5 to 20 mass%.

[0039] Furthermore, examples of compound (I) include a compound represented by formula (I-x2) (hereinafter, sometimes referred to as compound (I-x2)).

[0040] [ka]

[0041] [In formula (I-x2), G 1represents an alkanediyl group having 2 to 12 carbon atoms, and a hydrogen atom contained in the alkanediyl group may be substituted with an alkyl group having 1 to 4 carbon atoms, and -CH2- contained in the alkanediyl group may be substituted with -O-. J 1 is a hydrogen atom, -NR a R b or -NR a R b H + Q - Represents. R a and R b each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. Q - is a halide ion, BF4 - , PF6 - , ClO4 - , X a -CO2 - or Y a -SO3 - Represents. X a and Y a each independently represents a monovalent organic group. n a represents an integer from 1 to 4.]

[0042] Formula (I-x2) represents n contained in the compound represented by formula (I-0). a hydrogen atoms, -SO2-NH-G 1 -J 1 n a is an integer of 2 or more, multiple -SO2-NH-G 1 -J 1 may be the same or different from each other.

[0043] [ka]

[0044] Examples of the alkanediyl group having 2 to 12 carbon atoms include linear alkanediyl groups such as ethylene, propanediyl, butanediyl, pentanediyl, hexanediyl, heptanediyl, octanediyl, nonanediyl, decanediyl, undecanediyl, and dodecanediyl groups; and branched alkanediyl groups such as 2-methylpropanediyl, 4-methylheptanediyl, 4-ethylheptanediyl, 4-propylheptanediyl, 2-butylheptanediyl, 3-propyloctanediyl, 2-butylnonanediyl, 4-methyldecanediyl, and 4-ethyldecanediyl groups.

[0045] Examples of the alkanediyl group having 2 to 12 carbon atoms in which —CH2— is replaced with —O— include a group represented by formula (G-1) and a group represented by formula (G-2).

[0046] [ka]

[0047] [In formula (G-1) and formula (G-2), G 2 ~G 5 each independently represents an alkanediyl group having 1 to 8 carbon atoms. n 1 represents an integer of 1 to 3. n 2 represents an integer of 0 to 3. However, the total number of carbon atoms and oxygen atoms contained in the group represented by formula (G-1) is 3 to 12, and the total number of carbon atoms and oxygen atoms contained in the group represented by formula (G-2) is 2 to 12. * represents a bond to -NH-.]

[0048] G 2 ~G 5 The alkanediyl group having 1 to 8 carbon atoms represented by the formula: 1 Among the alkanediyl groups having 2 to 12 carbon atoms represented by the formula: 2 ~G 5The alkanediyl groups having 1 to 8 carbon atoms represented by the following formula may be the same or different. n 1 is preferably an integer of 1 to 2, and more preferably an integer of 1. n 2 is preferably an integer of 0 to 2, more preferably an integer of 0 or 1, and even more preferably 0.

[0049] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, etc. Among these, a methyl group and an ethyl group are preferred, and a methyl group is more preferred. Examples of alkanediyl groups in which hydrogen atoms contained in the alkanediyl group are substituted with methyl groups include a (2-methyl)propanediyl group, a (1,3-dimethyl)butanediyl group, a (1,4-dimethyl)pentanediyl group, a (1-methyl)hexanediyl group, a (2-methyl)hexanediyl group, a (3-methyl)hexanediyl group, a (4-methyl)hexanediyl group, a (5-methyl)hexanediyl group, a (1,5-dimethyl)hexanediyl group, a (1,1,3,3-tetradimethyl)butanediyl group, a (5,5-dimethyl)hexanediyl group, a (7-methyl)octanediyl group, and a (10-methyl)undecanediyl group.

[0050] R a and R b Examples of the alkyl group having 1 to 8 carbon atoms represented by the formula: 1 Among the linear alkyl groups and branched alkyl groups of saturated or unsaturated chain hydrocarbon groups represented by the following formula, those having 1 to 8 carbon atoms are exemplified.

[0051] -SO2-NH-G 1 -J 1 Examples of the group include groups represented by the following formulas:

[0052] [ka]

[0053] G 1is a group represented by formula (G-1), -SO2-NH-G 1 -J 1 Examples of the group include groups represented by the following formulas:

[0054] [ka]

[0055] G 1 is a group represented by formula (G-2), -SO2-NH-G 1 -J 1 Examples of the group include groups represented by the following formulas:

[0056] [ka]

[0057] J 1 But, -NR a R b If -SO2-NH-G 1 -J 1 Examples of the group include groups represented by the following formulas:

[0058] [ka]

[0059] [ka]

[0060] J 1 But, -NR a R b H + Q - If -SO2-NH-G 1 -NR a R b H + Examples of the group include groups represented by the following formulas:

[0061] [ka]

[0062] [ka]

[0063] Q - is a halide ion, BF4 - , PF6 - , ClO4 - , X a -CO2 - or Y a -SO3 - Represents. X a and Y a represents a monovalent organic group. Examples of the monovalent organic group include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and groups formed by combining these groups. Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, and a decyl group. Examples of the cycloalkyl group having 3 to 20 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclodecyl group. Examples of the aryl group having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, and an anthryl group. X a -CO2 - is CO2 - is an organic anion containing a Y group. a -SO3 - is SO3 - The anions are organic anions containing a group, and examples thereof include anions represented by formulae (Q-1) to (Q-4).

[0064] [ka]

[0065] [R yrepresents an alkyl group having 1 to 20 carbon atoms. m a represents an integer from 0 to 5. Q - As for X a -CO2 - and Y a -SO3 - The anion represented by formula (I-x2) is preferably an anion represented by formula (Q-4), and more preferably an anion represented by formula (Q-4). These anions tend to increase the solubility of the compound represented by formula (I-x2) in solvents.

[0066] -(SO2-NH-G 1 -J 1 )n a In G 1 is preferably an alkanediyl group having 3 to 10 carbon atoms, more preferably an alkanediyl group having 4 to 9 carbon atoms, and a hydrogen atom contained in the alkanediyl group may be substituted with an alkyl group preferably having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 2 carbon atoms. J 1 is preferably a hydrogen atom. n a is preferably an integer of 2 to 4, more preferably an integer of 2 to 3, and even more preferably an integer of 3.

[0067] The alkanediyl group having 2 to 12 carbon atoms in which —CH2— is replaced by —O— is preferably a group represented by formula (G-1). G 2 is preferably an alkanediyl group having 1 to 5 carbon atoms, more preferably an alkanediyl group having 1 to 3 carbon atoms. G 3 is preferably an alkanediyl group having 1 to 3 carbon atoms, more preferably an alkanediyl group having 1 to 2 carbon atoms.

[0068] Examples of the compound represented by formula (I-x2) include compounds represented by formulas (2-1) to (2-92). Among the compounds represented by formulas (2-1) to (2-92), n a is an integer of 2 or more, multiple -SO2-NH-G 1 -J1 are preferably bonded to different benzene rings.

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] Compound (I-x2) is preferably a compound represented by formula (2-1) to formula (2-16), more preferably a compound represented by formula (2-9) to formula (2-12), and even more preferably a compound represented by formula (2-11).

[0075] The content of the compound (I-x2) in the total amount of the colorant (A) is preferably 1 to 100 mass%, more preferably 10 to 98 mass%, even more preferably 40 to 97 mass%, even more preferably 60 to 96 mass%, and particularly preferably 80 to 95 mass%.

[0076] The colorant (A) preferably contains one or more selected from the group consisting of the compound (I-x1) and the compound (I-x2), and more preferably contains the compound (I-x1) and the compound (I-x2).

[0077] The content of the compound (I-x1) and the compound (I-x2) in the total amount of the colorant (A) is preferably 70 to 100 mass %, more preferably 80 to 100 mass %, and even more preferably 90 to 100 mass %.

[0078] When the colorant (A) contains both the compound (I-x1) and the compound (I-x2), the mass ratio of the compound (I-x1):the compound (I-x2) is preferably 2:98 to 98:2, more preferably 5:95 to 45:55, and even more preferably 7:93 to 20:80.

[0079] <<Compound (II)>> The colorant (A) preferably contains a compound represented by formula (II) (hereinafter, sometimes referred to as compound (II)). Compound (II) is a dye containing a compound having a xanthene skeleton in the molecule. Compound (II) may be a tautomer thereof.

[0080] [ka]

[0081] [In formula (II), R 21 ~R 24 each independently represents a hydrogen atom, a monovalent saturated hydrocarbon group of 1 to 20 carbon atoms which may have a substituent, or a monovalent aromatic hydrocarbon group of 6 to 20 carbon atoms which may have a substituent, and -CH2- contained in the saturated hydrocarbon group is not -O-, -CO- or -NR 31 - may be replaced. R 25 -OH, -SO3 - , -SO3H, -SO3 - (Zd) + , -CO2H, -CO2 - (Zd) + , -CO2R 28 , -SO3R 28 , or -SO2NR 29 R 30 Represents. R 26 and R27 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. p represents an integer of 0 to 5. When p is 2 or more, a plurality of R 25 may be the same or different. q represents an integer of 0 or 1. Xa represents a halogen atom. (Zd) + teeth, + N(R 31 )4, Na + , or K + represents the four R's 31 may be the same or different. R 28 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom. R 29 and R 30 each independently represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the saturated hydrocarbon group is -O-, -CO-, -NH-, or -NR 28 - may be replaced by R 29 and R 30 may be bonded to form a 3- to 10-membered heterocyclic ring together with the adjacent nitrogen atom. R 31 represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.]

[0082] R 21 ~R 24Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in the formula (I) include linear alkyl groups such as methyl, ethyl, propyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and icosyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl; and alicyclic saturated hydrocarbon groups having 2 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl. The number of carbon atoms in the saturated hydrocarbon group includes the number of carbon atoms in the substituent, if any. Examples of the substituent that the saturated hydrocarbon group may have include halogen atoms, -OH, -OR, and the like. 28 , -SO3 - , -SO3H, -SO3 - (Zd) + , -CO2H, -CO2R 28 , -SR 28 , -SO2R 28 , -SO3R 28 , -SO2NR 29 R 30 , or -Si(OR 32 )(OR 33 )(OR 34 ) are listed. R 32 , R 33 , and R 34 each independently represents a monovalent saturated hydrocarbon group having 1 to 4 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.

[0083] R 21 ~R 24 In the above formula, examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group. Examples of the monovalent aromatic hydrocarbon group having a substituent include a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group. When the aromatic hydrocarbon group has a substituent, the number of carbon atoms in the substituent is the number including the carbon atoms in the substituent. Examples of the substituent that the aromatic hydrocarbon group may have include a halogen atom, -R 28 , -OH, -OR 28 , -SO3 - , -SO3H, -SO3- (Zd) + , -CO2H, -CO2R 28 , -SR 28 , -SO2R 28 , -SO3R 28 , -SO2NR 29 R 30 , or -Si(OR 32 )(OR 33 )(OR 34 ) are listed.

[0084] R 28 ~R 31 Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in the formula (I) include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and icosyl groups; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl groups; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl groups.

[0085] R 29 and R 30 The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in the formula (I) may have a substituent, such as a hydroxy group or a halogen atom.

[0086] R 32 ~R 34 Examples of the monovalent saturated hydrocarbon group having 1 to 4 carbon atoms in the formula (I) include linear alkyl groups such as a methyl group, an ethyl group, a propyl group, and a butyl group; and alicyclic saturated hydrocarbon groups having 1 to 4 carbon atoms such as branched alkyl groups such as an isopropyl group and an isobutyl group.

[0087] (Zd) + teeth, + N(R 31 )4, Na + or K + and preferably + N(R 31)4. + N(R 31 ) 4 R's in 4 31 Among the four R, at least two are preferably monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. 31 The total number of carbon atoms in compound (II) is preferably 20 to 80, more preferably 20 to 60. + N(R 31 )4 exists, R 31 When is one of these groups, a color filter containing little foreign matter can be formed from a negative resist composition containing compound (II).

[0088] -OR 28 Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, and an icosyloxy group.

[0089] -CO2R 28 Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.

[0090] -SR 28 Examples of the sulfanyl group include a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, and an icosylsulfanyl group. -SO2R 28 Examples of the sulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group. -SO3R 28 Examples of the sulfonyl group include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group.

[0091] -SO2NR29 R 30 Examples include a sulfamoyl group; N-Methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-(1,1-dimethylpropyl)sulfamoyl group, N-(1,2-dimethylpropyl)sulfamoyl group, N-(2,2-dimethylpropyl)sulfamoyl group, N-(1-methylbutyl)sulfamoyl group, N-(2-methylbutyl)sulfamoyl group N-1-substituted sulfamoyl groups such as a sulfamoyl group, an N-(3-methylbutyl)sulfamoyl group, an N-cyclopentylsulfamoyl group, an N-hexylsulfamoyl group, an N-(1,3-dimethylbutyl)sulfamoyl group, an N-(3,3-dimethylbutyl)sulfamoyl group, an N-heptylsulfamoyl group, an N-(1-methylhexyl)sulfamoyl group, an N-(1,4-dimethylpentyl)sulfamoyl group, an N-octylsulfamoyl group, an N-(2-ethylhexyl)sulfamoyl group, an N-(1,5-dimethyl)hexylsulfamoyl group, and an N-(1,1,2,2-tetramethylbutyl)sulfamoyl group; Examples include N,N-disubstituted sulfamoyl groups such as N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, N,N-bis(1-methylpropyl)sulfamoyl group and N,N-heptylmethylsulfamoyl group.

[0092] -Si(OR 32 )(OR 33 )(OR 34 ) includes, for example, a trimethoxysilyl group, a triethoxysilyl group, and the like.

[0093] R25 -CO2H, -CO2 - (Zd) + , -CO2R 28 , -SO3 - , -SO3 - (Zd) + , -SO3H, or SO2NHR 29 is preferred, and SO3 - , -SO3 - (Zd) + , -SO3H or SO2NHR 29 is more preferred.

[0094] p represents an integer of 0 to 5, preferably 1 to 4, more preferably 1 or 2, and even more preferably 1.

[0095] R 26 and R 27 As the alkyl group having 1 to 6 carbon atoms in R, among the alkyl groups listed above, those having 1 to 6 carbon atoms can be mentioned, and alkyl groups having 1 to 2 carbon atoms are preferred. 26 and R 27 is more preferably a hydrogen atom.

[0096] R 31 Examples of the aralkyl group having 7 to 10 carbon atoms in the formula include a benzyl group, a phenylethyl group, and a phenylbutyl group.

[0097] q represents an integer of 0 or 1, with 0 being preferred.

[0098] A preferred example of compound (II) is a compound represented by formula (IIa) (hereinafter sometimes referred to as "compound (IIa)"). The compound represented by formula (IIa) may be used without being combined with a compound of compound (II) other than compound (IIa) (hereinafter sometimes referred to as "compound (IIb)"), or compound (IIa) and compound (IIb) may be used in combination. Two or more types of compound (IIa) may also be used in combination.

[0099] [ka]

[0100] [In formula (IIa), R a1 and R a4 are each independently a monovalent aromatic hydrocarbon group which may have two or less monovalent saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms. R a2 and R a3 are each independently a hydrogen atom, a methyl group, or an ethyl group. R 25 ~R 27 , p, q, and Xa have the same meanings as above.]

[0101] R a1 and R a4 As for the above R 21 and R 24 Among groups similar to those mentioned above, examples include monovalent aromatic hydrocarbon groups that have no substituents, and monovalent aromatic hydrocarbon groups that have two or less monovalent saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms. Of these, monovalent aromatic hydrocarbon groups that have two or less monovalent saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms are preferred.

[0102] An example of a monovalent aromatic hydrocarbon group having no substituent is a phenyl group. Examples of a monovalent aromatic hydrocarbon group having two or less monovalent saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms include a toluyl group, a xylyl group, and a mesityl group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 7 to 20, more preferably 7 to 16, even more preferably 7 to 10, and most preferably 8. The number of carbon atoms in the aromatic hydrocarbon group includes the number of carbon atoms in the substituent. It is preferable that the aromatic hydrocarbon group has no substituents other than the saturated aliphatic hydrocarbon group.

[0103] The number of saturated aliphatic hydrocarbon groups bonded to the aromatic hydrocarbon group is preferably 1 to 2, and more preferably 2. The saturated aliphatic hydrocarbon group is preferably bonded to the ortho- or meta-position relative to the bond of the aromatic hydrocarbon group, and more preferably to the ortho-position. Examples of the saturated aliphatic hydrocarbon group include saturated aliphatic hydrocarbon groups that do not have a substituent. The number of carbon atoms in the saturated aliphatic hydrocarbon group is preferably 1 to 4, more preferably 1 to 3, even more preferably 1 to 2, and most preferably 1.

[0104] R a2 and R a3 Examples of the alkyl group include a hydrogen atom, a methyl group, and an ethyl group. Of these, a hydrogen atom or a methyl group is preferred, and a hydrogen atom is more preferred.

[0105] As compound (IIb), a compound represented by formula (Ib1) (hereinafter sometimes referred to as "compound (Ib1)") is preferably used.

[0106] [ka]

[0107] [In formula (Ib1), R b1 ~R b4 each independently represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent; R b1 ~R b4 At least one saturated hydrocarbon group or aromatic hydrocarbon group contained in 28 , -CO2H, -CO2R 28 , -SO3 - , -SO3H, -SO3 - (Zd) + , -SR 28 , -SO2R 28 , -SO3R 28 , -SO2NR 29 R30 , or -Si(OR 32 )(OR 33 )(OR 34 ) as a substituent, or R b1 ~R b4 At least one aromatic hydrocarbon group contained in the formula (I) has three or more monovalent saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms as substituents, R 25 ~R 30 , R 32 ~R 34 , p, q, and Xa have the same meanings as above.]

[0108] R b1 and R b4 As for the above R 21 and R 24 Examples of groups similar to those mentioned above include a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having three or more monovalent saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms as substituents. Of these, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having three or more monovalent saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms as substituents is preferred.

[0109] The number of carbon atoms in the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, which may have a substituent, is preferably 1 to 10, more preferably 2 to 8, and even more preferably 2 to 7. The number of carbon atoms in the saturated aliphatic hydrocarbon group includes the number of carbon atoms in the substituent. Examples of the substituent include a halogen atom, -OH, -OR 28 , -CO2H, -CO2R 28 , -SO3 - , -SO3H, -SO3 - (Zd) + , -SR 28 , -SO2R 28 , -SO3R 28 , -SO2NR 29 R 30 , or -Si(OR 32 )(OR33 )(OR 34 ) is preferred, and —OH, —OR 28 , -CO2H, -CO2R 28 , -SO3 - , -SO3H, -SO3 - (Zd) + , -SR 28 , -SO2R 28 , -SO3R 28 , or -Si(OR 32 )(OR 33 )(OR 34 ), and more preferably —OH, —OR 28 , -CO2H, -CO2R 28 , or -Si(OR 32 )(OR 33 )(OR 34 ), most preferably -Si(OR 32 )(OR 33 )(OR 34 The number of substituents is preferably 1 to 5, more preferably 1 to 3, still more preferably 1 or 2, and most preferably 1, per saturated aliphatic hydrocarbon group.

[0110] The number of carbon atoms in the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, which may have a substituent, is preferably 7 to 20, more preferably 7 to 16, even more preferably 7 to 12, still more preferably 7 to 10, particularly preferably 7 to 8, and most preferably 8. The number of carbon atoms in the aromatic hydrocarbon group includes the number of carbon atoms in the substituent. Examples of the substituent include a monovalent saturated aliphatic hydrocarbon group having 1 to 4 carbon atoms, a halogen atom, -OH, -OR 28 , -CO2 H, -CO2R 28 , -SO3 - , -SO3H, -SO3 - (Zd) + , -SR 28 , -SO2R 28 , -SO3R 28 , -SO2NR 29 R 30 , or -Si(OR 32 )(OR 33 )(OR 34) is preferred, and more preferred are monovalent saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms, -OH, -OR 28 , -CO2H, -CO2R 28 , -SO3 - , -SO3H, -SO3 - (Zd) + , -SR 28 , -SO2R 28 , -SO3R 28 , or -SO2NR 29 R 30 More preferably, it is a monovalent saturated aliphatic hydrocarbon group having 1 to 4 carbon atoms, -OR 28 , -SO3 - , -SO3H, -SO3 - (Zd) + , -SR 28 , -SO2R 28 , -SO3R 28 , or -SO2NR 29 R 30 The number of substituents per aromatic hydrocarbon group is preferably 1 to 5, more preferably 1 to 3, even more preferably 1 or 2, and most preferably 2. The substituents are preferably bonded to the ortho- and / or meta-positions, more preferably ortho-positions, relative to the bonds of the aromatic hydrocarbon group.

[0111] The number of carbon atoms in an aromatic hydrocarbon group having three or more monovalent saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms as substituents is preferably 9 to 20, more preferably 9 to 13, even more preferably 9 to 12, and most preferably 9. The number of carbon atoms in the aromatic hydrocarbon group includes the number of carbon atoms in the substituents. The aromatic hydrocarbon group preferably has no substituents other than the saturated aliphatic hydrocarbon group. The number of saturated aliphatic hydrocarbon groups per aromatic hydrocarbon group is preferably 3 to 5, more preferably 3 to 4, and most preferably 3. The saturated aliphatic hydrocarbon groups are preferably bonded at the ortho and / or para positions relative to the bond of the aromatic hydrocarbon group, and more preferably at the ortho and para positions. The number of carbon atoms in the monovalent saturated aliphatic hydrocarbon group is preferably 1 to 5, more preferably 1 to 3, even more preferably 1 or 2, and most preferably 1.

[0112] R b2 and R b3 As for the above R 22 and R 23 Of the groups similar to those listed above, preferred are hydrogen atoms and monovalent saturated hydrocarbon groups of 1 to 20 carbon atoms which may have a substituent. Of these, monovalent saturated hydrocarbon groups of 1 to 20 carbon atoms which may have a substituent are more preferred, and monovalent saturated hydrocarbon groups of 1 to 20 carbon atoms which have a substituent are even more preferred.

[0113] The number of carbon atoms in the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, which may have a substituent, is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms in the saturated aliphatic hydrocarbon group includes the number of carbon atoms in the substituent. Examples of the substituent include a halogen atom, -OH, -OR 28 , -CO2H, -CO2R 28 , -SO3 - , -SO3H, -SO3 - (Zd) + , -SR 28 , -SO2R 28 , -SO3R 28 , -SO2NR 29 R 30, or -Si(OR 32 )(OR 33 )(OR 34 ) is preferably mentioned, and more preferably —OH, —OR 28 , -CO2H, -CO2R 28 , -SO3 - , -SO3H, -SO3 - (Zd) + , -SR 28 , -SO2R 28 , -SO3R 28 , or -Si(OR 32 )(OR 33 )(OR 34 ), and more preferably —OH, —OR 28 , -CO2H, -CO2R 28 , or -Si(OR 32 )(OR 33 )(OR 34 ), most preferably -CO2H or -CO2R 28 The number of substituents is preferably 1 to 5, more preferably 1 to 3, even more preferably 1 or 2, and most preferably 1, per saturated aliphatic hydrocarbon group.

[0114] As the compound (IIa), compounds No. 1 to 15 specified in the formula (IaX) and Table 2 are preferred.

[0115] [ka]

[0116] [Table 2]

[0117] The symbols in the formulae represent the following groups (in the following, * represents a bond).

[0118] [ka]

[0119] As the compound (Ib1), compounds Nos. 16 to 35 specified in formula (Ibx) and Table 3, and compounds represented by formulae A3-1 to A3-8 are preferred.

[0120] [ka]

[0121] [Table 3]

[0122] The symbols in the formulae represent the following groups (in the following, * represents a bond).

[0123] [ka]

[0124] [ka]

[0125] <<Colorant (A1)>> The curable composition of the present invention may contain, as the colorant (A), a dye and / or pigment other than the colorant (A2) (hereinafter, the dye and the pigment may be collectively referred to as colorant (A1)). These may be used alone or in combination of two or more.

[0126] The colorant (A1) is not particularly limited, and known dyes and / or pigments can be used as long as it does not contain the colorant (A2).

[0127] When the colorant (A1) is a dye, examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used based on their chemical structure include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes (excluding Compound (II)), thiazole dyes, oxazine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes (excluding Compound (I)).

[0128] When the colorant (A1) is a pigment, known pigments can be used, for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments classified as pigments include yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 139, 147, 148, 153, 154, 166, 173, 194, and 214; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 144, 149, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 255, 264, 265, 266, 268, 273; Blue pigments such as CI Pigment Blue 15, 15:1, 15:2; Violet pigments such as CI Pigment Violet 1, 32, 36, 38; Green pigments such as CI Pigment Green 7 and 36; Brown pigments such as CI Pigment Brown 23 and 25; Black pigments such as CI Pigment Black 1 and 7;

[0129] The pigment may be subjected to, as necessary, rosin treatment, surface treatment using a derivative having an acidic or basic group introduced therein, grafting treatment onto the pigment surface using a polymer compound, atomization treatment using sulfuric acid atomization, washing treatment using an organic solvent or water to remove impurities, or treatment to remove ionic impurities using an ion exchange method. The pigment preferably has a substantially uniform particle size. The pigment can be dispersed in a dispersant solution to form a pigment dispersion in which the pigment is uniformly dispersed. When multiple pigments are used, each pigment may be dispersed individually, or multiple pigments may be mixed and dispersed. Alternatively, the pigment may be mixed with the compound (I) and dispersed. Examples of dispersants include those described above.

[0130] When a dispersant is used, the amount of the dispersant (solid content) used is usually 10 to 200 parts by mass, preferably 15 to 180 parts by mass, and more preferably 20 to 160 parts by mass, relative to 100 parts by mass of the pigment. When the amount of the dispersant used is within the above range, a pigment dispersion in a more uniformly dispersed state tends to be obtained.

[0131] When the colorant (A) contains the colorant (A1), the content of the colorant (A1) is preferably 1 to 60 mass %, more preferably 1 to 40 mass %, and even more preferably 1 to 20 mass %, of the total amount of the colorant (A).

[0132] The content of colorant (A) is preferably 1 to 70 mass %, more preferably 5 to 60 mass %, even more preferably 10 to 60 mass %, and even more preferably 15 to 55 mass %, relative to the total amount of solids in the curable composition. When the content of colorant (A) is within the above range, the color density when made into a color filter is sufficient, and since the necessary amount of resin (B) can be contained in the composition, a pattern with sufficient mechanical strength can be formed, which is preferable. Here, the "total amount of solids" in this specification refers to the amount obtained by subtracting the content of the organic solvent from the total amount of the curable composition. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0133] <Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6]. Resin [K1]: a copolymer having structural units derived from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure and an ethylenically unsaturated bond having 2 to 4 carbon atoms; Resin [K2]: a copolymer having structural units derived from (a), structural units derived from (b), and structural units derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, sometimes referred to as "(c)"); Resin [K3]: a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]: a copolymer having a structural unit derived from (a) to which (b) has been added, and a structural unit derived from (c); Resin [K5]: a copolymer having a structural unit derived from (b) to which (a) has been added and a structural unit derived from (c); Resin [K6]: A copolymer having a structural unit derived from (c) and a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a polycarboxylic acid and / or a carboxylic acid anhydride.

[0134] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among these, acrylic acid, methacrylic acid, etc. are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in an alkaline aqueous solution.

[0135] (b) refers to, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

[0136] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").

[0137] Examples of (b1) include a monomer (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.

[0138] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0139] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (BI), and compounds represented by formula (BII).

[0140] [ka]

[0141] [In formula (BI) and formula (BII), R e and R f represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X e and X fis a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g represents -NH-. R g represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0142] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R e and R f Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0143] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. X e and X f Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).

[0144] Examples of compounds represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formula (BI-1), (BI-3), (BII-5), (BI-7), (BI-9) or (BI-11) to (BI-15) are preferred, and compounds represented by formula (BI-1), (BI-7), (BI-9) or (BI-15) are more preferred.

[0145] [ka]

[0146] Examples of the compound represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15). Among these, compounds represented by formula (BII-1), (BII-3), (BII-5), (BII-7), (BII-9) or (BII-11) to (BII-15) are preferred, and compounds represented by formula (BII-1), (BII-7), (BII-9) or (BII-15) are more preferred.

[0147] [ka]

[0148] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio thereof (compound represented by formula (BI) : compound represented by formula (BII)) is preferably 5:95 to 95:5, more preferably 20:80 to 80:20 on a molar basis.

[0149] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like.

[0150] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0151] As (b), (b1) is preferred in that it can further increase the reliability of the obtained color filter in terms of heat resistance, chemical resistance, etc. Furthermore, (b1-2) is more preferred in that it provides excellent storage stability of the curable composition.

[0152] Examples of (c) include (meth)acrylic acid esters (cf-1) (hereinafter sometimes referred to as "(cf-1)") that do not have a polycyclic hydrocarbon ring, such as methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; Tricyclo[5.2.1.0 2,6 ]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 ](meth)acrylic acid esters (cf-2) having a polycyclic hydrocarbon ring, such as decene-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the technical field), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, and adamantyl (meth)acrylate (hereinafter sometimes referred to as "(cf-2)"); hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene Bicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene bicyclounsaturated compounds such as ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide; Examples include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Of these, (meth)acrylic acid esters are preferred.

[0153] In the resin [K1], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: When the ratio of the structural units of the resin [K1] is within the above range, the storage stability of the curable composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.

[0154] Resin [K1] can be produced, for example, by the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and by reference to the references described in said literature.

[0155] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, followed by heating and keeping the temperature while stirring. The polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, etc.). Solvents that dissolve the respective monomers can be used, and examples of the solvents include those described below as the organic solvent (E) of the curable composition of the present invention.

[0156] The obtained copolymer may be used as a solution after the reaction as is, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. In particular, by using the solvent contained in the curable composition of the present invention as a solvent during the polymerization, the solution after the reaction can be used as is for preparing the curable composition of the present invention, thereby simplifying the production process of the curable composition of the present invention.

[0157] In the resin [K2], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 45 mol% Structural units derived from (b): 2 to 95 mol% Structural units derived from (c): 1 to 65 mol% Preferably, Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 80 mol% Structural units derived from (c): 5 to 60 mol% It is more preferable that: When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the curable composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained color filter tend to be excellent.

[0158] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0159] In the resin [K3], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that: Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

[0160] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].

[0161] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours to produce the resin [K4]. The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). This range tends to improve the storage stability of the curable composition, the developability during pattern formation, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern. Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K4], and (b1-1) is even more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

[0162] Resin [K5] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0163] Furthermore, under the same conditions as in the production method of resin [K4], resin [K5] can be obtained by reacting the cyclic ether derived from (b) contained in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used to react with the copolymer is preferably 5 to 100 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.

[0164] Resin [K6] is a resin obtained by further reacting resin [K5] with a polycarboxylic acid and / or a carboxylic anhydride. The hydroxyl group generated by the reaction of the cyclic ether derived from (b) with the carboxylic acid or carboxylic anhydride derived from (a) is further reacted with a polycarboxylic acid and / or a carboxylic anhydride. Examples of polycarboxylic acids include oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, and tricarbanilic acid. Examples of carboxylic acid anhydrides include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride. The amount of polycarboxylic acid and / or carboxylic acid anhydride used is preferably 0.05 to 1 mol, and more preferably 0.1 to 0.5 mol, per 1 mol of (a) used. In other words, it is more preferable that the resin [K6] also has a structural unit in which (a) is added to a structural unit derived from (b), in which a polycarboxylic acid and / or a carboxylic acid anhydride is not added to the hydroxy group generated by the reaction of a cyclic ether derived from (b) with a carboxylic acid or a carboxylic acid anhydride derived from (a).

[0165] The resin (B) preferably includes a resin having a structural unit with an ethylenically unsaturated bond in the side chain (resin [K4], resin [K5], or resin [K6]), and more preferably includes a resin having a structural unit with a (meth)acryloyl group in the side chain.

[0166] Examples of resins having a structural unit containing a (meth)acryloyl group in the side chain include resin [K4] using a monomer (ba) (hereinafter sometimes referred to as "(ba)") having a (meth)acryloyl group as (b), such as glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3-methyl-3-methacryloyloxymethyloxetane, or tetrahydrofurfuryl acrylate; resin [K5] using a monomer (aa) (hereinafter sometimes referred to as "(aa)") having a (meth)acryloyl group as (a), such as acrylic acid, methacrylic acid, or succinic acid mono[2-(meth)acryloyloxyethyl]; and resin [K6] using (aa) as (a). Resins having a structural unit containing a (meth)acryloyl group in the side chain preferably include resin [K6] using (aa) as (a).

[0167] The resin having a structural unit containing a (meth)acryloyl group in the side chain more preferably includes a resin [K6] having a structural unit containing a (meth)acryloyl group in the side chain and containing a carboxylic acid group derived from a polycarboxylic acid and / or a carboxylic acid anhydride (a structural unit obtained by adding (aa) to a structural unit derived from (b) and further adding a polycarboxylic acid and / or a carboxylic acid anhydride), a structural unit containing a (meth)acryloyl group in the side chain and not containing a carboxylic acid group derived from a polycarboxylic acid and / or a carboxylic acid anhydride (a structural unit obtained by adding (aa) to a structural unit derived from (b)), and a structural unit derived from (c). It is more preferable that the resin [K6] contains a structural unit which contains a (meth)acryloyl group in the side chain and does not contain a carboxylic acid group derived from a polycarboxylic acid and / or a carboxylic anhydride (a structural unit obtained by adding (aa) to a structural unit derived from (b)), and a structural unit derived from (cf-1) and / or (cf-2). It is particularly preferable that the resin [K6] contains a structural unit which contains a (meth)acryloyl group in the side chain and contains a carboxylic acid group derived from a polycarboxylic acid and / or a carboxylic anhydride (a structural unit obtained by adding (aa) to a structural unit derived from (b) and further adding a polycarboxylic acid and / or a carboxylic anhydride), a structural unit which contains a (meth)acryloyl group in the side chain and does not contain a carboxylic acid group derived from a polycarboxylic acid and / or a carboxylic anhydride (a structural unit obtained by adding (aa) to a structural unit derived from (b)), and a structural unit derived from (cf-1) and (cf-2).

[0168] Furthermore, from the viewpoint of increasing the residual film rate, it is preferable that the resin (B) further contains a resin [K1] in addition to a resin having a structural unit with an ethylenically unsaturated bond in a side chain (resin [K4], resin [K5], or resin [K6]).

[0169] The polystyrene-equivalent weight average molecular weight of resin (B) is preferably 3,000 to 100,000, more preferably 4,000 to 90,000, even more preferably 5,000 to 80,000, and even more preferably 8,000 to 70,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, and the solubility of the unexposed areas in the developer is good, which tends to improve the resolution of the colored pattern.

[0170] The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

[0171] The acid value of the resin (B) is preferably 20 to 170 mg-KOH / g, more preferably 25 to 150 mg-KOH / g, and even more preferably 30 to 130 mg-KOH / g, calculated as solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0172] The content of resin (B) is preferably 7 to 65 mass%, more preferably 13 to 60 mass%, even more preferably 17 to 55 mass%, and still more preferably 20 to 50 mass%, based on the total amount of solids in the curable composition. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[0173] <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). The polymerizable compound contains at least one compound selected from the group consisting of hexitol poly(meth)acrylates and polyglycerin poly(meth)acrylates, preferably hexitol poly(meth)acrylates or polyglycerin poly(meth)acrylates, and more preferably hexitol polyacrylates or polyglycerin polyacrylates.

[0174] <<Hexitol poly(meth)acrylate>> The hexitol poly(meth)acrylate contained as the polymerizable compound (C) has a structure in which one or more (meth)acryloyl groups are introduced into six hydroxyl groups present in the hexitol. The six hydroxyl groups present in the hexitol may be modified with ethylene oxide. That is, the hexitol poly(meth)acrylate may have an ethylene oxide chain represented by -O-CH2-CH2- at the terminal hydroxyl group of the hexitol, and a (meth)acryloyl group may be bonded to an oxygen atom of the ethylene oxide chain.

[0175] The hexitol poly(meth)acrylate is preferably a compound represented by the following formula (CA).

[0176] [ka]

[0177] [In formula (CA), Y represents a hydrogen atom or a (meth)acryloyl group, and the number of (meth)acryloyl groups contained in formula (CA) is 1 or more and 6 or less. a to f each independently represent the number of -O-CH2-CH2- units, and a+b+c+d+e+f is 0 or more and 24 or less.

[0178] The number of (meth)acryloyl groups represented by Y is preferably 2 or more, more preferably 3 or more, and even more preferably 4 or more, and may be 5 or less. The number of hydrogen atoms represented by Y is preferably 0 or more and 6 or less, more preferably 1 or more and 5 or less, and even more preferably 4 or less.

[0179] The (meth)acryloyl groups represented by Y may be the same or different, i.e., may be a methacryloyl group, an acryloyl group, or both a methacryloyl group and an acryloyl group. Of these, the (meth)acryloyl group represented by Y is preferably an acryloyl group.

[0180] In formula (CA), a+b+c+d+e+f (the number of ethylene oxides) is preferably 3 or more, more preferably 4 or more, even more preferably 5 or more, still more preferably 6 or more, and preferably 21 or less, more preferably 20 or less, still more preferably 19 or less, and still more preferably 18 or less.

[0181] As the hexitol poly(meth)acrylate, compounds represented by formulas (CA-1) to (CA-36) shown in Table 4 are preferred. Compounds represented by formulas (CA-1) to (CA-18) are more preferred, Compounds represented by formulas (CA-1) to (CA-6) and (CA-13) to (CA-18) are more preferred, compounds represented by formulas (CA-2) to (CA-5) and (CA-14) to (CA-17) are even more preferred, and compounds represented by formulas (CA-3) and (CA-17) are particularly preferred.

[0182] [Table 4]

[0183] As the hexitol poly(meth)acrylate, a sorbitol poly(meth)acrylate represented by formula (CA-I) is more preferred.

[0184] [ka]

[0185] [In formula (CA-I), Y and a to f are the same as defined above.] The compounds represented by formulae (CA-1) to (CA-36) in Table 4 preferably have a similar structure.

[0186] As the hexitol poly(meth)acrylate, commercially available products may be used, and examples thereof include sorbitol poly(meth)acrylates such as MT2519 (manufactured by Toagosei Co., Ltd., a+b+c+d+e+f=18, the number of HC=CH-CO-* groups in Y is 5; the number of H-* groups is 1) and MT2518 (manufactured by Toagosei Co., Ltd., a+b+c+d+e+f=6, the number of HC=CH-CO-* groups in Y is 3; the number of H-* groups is 3).

[0187] The content of the hexitol poly(meth)acrylate in the total amount of the polymerizable compound (C) is preferably 50 to 100 mass %, more preferably 60 to 100 mass %, and even more preferably 80 to 100 mass %.

[0188] <<Polyglycerin poly(meth)acrylate>> The polyglycerol poly(meth)acrylate contained as the polymerizable compound (C) has a structure in which one or more (meth)acryloyl groups are introduced into the hydroxyl groups of polyglycerol formed by polymerizing two or more glycerol units. The hydroxyl groups of the polyglycerol may be modified with ethylene oxide; that is, the polyglycerol poly(meth)acrylate may have an ethylene oxide chain represented by -O-CH2-CH2- at the terminal of the hydroxyl group of the polyglycerol, and a (meth)acryloyl group may be bonded to an oxygen atom of the ethylene oxide chain.

[0189] The polyglycerin poly(meth)acrylate is preferably a compound represented by the following formula (CB).

[0190] [ka]

[0191] [In formula (CB), Z represents a hydrogen atom or a (meth)acryloyl group, and the number of (meth)acryloyl groups contained in formula (CB) is 1 or more and (n+2) or less. g to i each independently represent the number of -O-CH2-CH2- units and are integers of 0 or more and 5 or less. n represents the degree of polymerization of glycerin and is an integer of 2 or more and 20 or less.

[0192] n is preferably 3 or more, more preferably 4 or more, and is preferably 18 or less, more preferably 15 or less, and even more preferably 12 or less.

[0193] The number of (meth)acryloyl groups represented by Z is preferably 2 or more, more preferably 3 or more, even more preferably 4 or more, still more preferably 5 or more, and preferably 20 or less, more preferably 18 or less, even more preferably 16 or less, still more preferably 14 or less, and particularly preferably 12 or less. The number of hydrogen atoms represented by Z is preferably 0 or more and 5 or less, more preferably 1 or more and 4 or less, and even more preferably 1 or more and 3 or less.

[0194] The (meth)acryloyl groups represented by Z may be the same or different, i.e., may be a methacryloyl group, an acryloyl group, or both a methacryloyl group and an acryloyl group. Of these, the (meth)acryloyl group represented by Z is preferably an acryloyl group.

[0195] In formula (CB), g to i (the number of ethylene oxides) are each independently preferably 1 or more and 3 or less, more preferably 2 or less, and particularly preferably 1.

[0196] As the polyglycerin poly(meth)acrylate, compounds represented by formulas (CB-1) to (CB-56) shown in Table 5 are preferred. Compounds represented by formulas (CB-1) to (CB-28) are more preferred, Compounds represented by formulae (CB-1) to (CB-4) and (CB-25) to (CB-28) are more preferred, and compounds represented by formulae (CB-1) and (CB-25) are even more preferred.

[0197] [Table 5]

[0198] As the polyglycerin poly(meth)acrylate, commercially available products may be used, such as SA-TE6 represented by formula (CB-1) and SA-ZE12 represented by formula (CB-25) (both manufactured by Sakamoto Pharmaceutical Industry Co., Ltd.).

[0199] The content of polyglycerin poly(meth)acrylate in the total amount of the polymerizable compound (C) is preferably 50 to 100 mass %, more preferably 60 to 100 mass %, and even more preferably 80 to 100 mass %.

[0200] <<Polymerizable compound (C1)>> The curable composition of the present invention may contain, as the polymerizable compound (C), a polymerizable compound (polymerizable compound (C1)) other than hexitol poly(meth)acrylate and polyglycerin poly(meth)acrylate. The polymerizable compound (C1) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond other than hexitol poly(meth)acrylate and polyglycerin poly(meth)acrylate, and preferably a (meth)acrylic acid ester compound (however, excluding hexitol poly(meth)acrylate and polyglycerin poly(meth)acrylate).

[0201] Among them, the polymerizable compound (C1) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tri(meth)acrylate, tetra ... Examples of the acrylate copolymer include 2-(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate.

[0202] The weight average molecular weight of the polymerizable compound (C1) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.

[0203] From the viewpoint of pixel bottoming, the content of at least one selected from the group consisting of hexitol poly(meth)acrylate and polyglycerin poly(meth)acrylate is preferably 80 to 100 mass%, more preferably 90 to 100 mass%, and even more preferably 100 mass%, of the total amount of polymerizable compound (C).

[0204] The content of the polymerizable compound (C) is preferably 5 to 45 mass %, more preferably 10 to 40 mass %, and even more preferably 15 to 35 mass %, based on the total amount of solids in the curable composition.

[0205] <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 and initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0206] The O-acyloxime compound is a compound having a partial structure represented by the following formula (d1): In the following, * represents a bond.

[0207] [ka]

[0208] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl)-2-methylbenzoyl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl) ... Examples of suitable hydroxybenzoates include N-acetyl-1-[9-ethyl-2,4-dioxacyclopentanylmethyloxy]benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine. Commercially available products such as Irgacure OXE01 and OXE02 (manufactured by BASF) and N-1919 (manufactured by ADEKA) may also be used. Among them, the O-acyloxime compound is preferably at least one selected from the group consisting of N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, with N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine being more preferred. These O-acyloxime compounds tend to produce color filters with high brightness.

[0209] The alkylphenone compound is a compound having a partial structure represented by the following formula (d2) or a partial structure represented by the following formula (d3): In these partial structures, the benzene ring may have a substituent.

[0210] [ka]

[0211] Examples of compounds having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907 (2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one), and 379 (all manufactured by BASF) may also be used.

[0212] Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

[0213] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0214] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

[0215] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, ... 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).

[0216] Further examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) (especially amines) described below.

[0217] Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl tosylates; and benzoin tosylates.

[0218] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, more preferably a polymerization initiator containing at least one selected from the group consisting of an O-acyloxime compound and an alkylphenone compound, and even more preferably a polymerization initiator containing an O-acyloxime compound.

[0219] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 25 parts by mass, and even 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, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving productivity of the optical filter.

[0220] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiation aid (D1) include 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, and N-phenylglycine.

[0221] When these polymerization initiation aids (D1) are used, the content thereof 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 amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with even higher sensitivity, and the productivity of the color filter tends to improve.

[0222] <Organic solvent (E)> The organic solvent (E) is not particularly limited, and an organic solvent commonly used in the art can be used. Examples thereof include 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- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, or -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc.

[0223] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0224] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

[0225] Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxy ... Examples of the alkyl ether acetate include ethyl 2-methoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0226] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0227] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0228] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0229] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0230] The organic solvent (E) preferably contains one or more selected from the group consisting of ether solvents, ether ester solvents, and ketone solvents, more preferably contains an ether ester solvent and a ketone solvent, and further preferably contains propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone.

[0231] The content of the organic solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the curable composition of the present invention. In other words, the solid content of the curable composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content of the organic solvent (E) is within the above range, the flatness during coating is good, and when a color filter is formed, the color density is not insufficient, so that the display characteristics tend to be good.

[0232] <Leveling Agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms, which may have a polymerizable group in the side chain. Examples of silicone surfactants include surfactants having a siloxane bond in the molecule, such as Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade names: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).

[0233] Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule, such as Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), Ftop (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by AGC Corporation (formerly Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemical Research Institute, Ltd.).

[0234] Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0235] When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.001 to 0.2 mass%, more preferably 0.002 to 0.1 mass%, relative to the total amount of the curable composition. This content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0236] <Other ingredients> The curable composition of the present invention may contain additives known in the art, such as fillers, other polymeric compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as needed.

[0237] <Method for producing curable composition> The curable composition of the present invention can be prepared, for example, by mixing the resin (B), the polymerizable compound (C), and the polymerization initiator (D), as well as the colorant (A), the organic solvent (E), the leveling agent (F), and other components that are used as needed. The colorant (A) may be prepared using the above-mentioned color dispersion or pigment dispersion. The desired curable composition can be prepared by mixing the remaining components with the color dispersion or pigment dispersion to a predetermined concentration. When the dye (A1-1) is contained, the dye (A1-1) may be dissolved in advance in part or all of the organic solvent (E) to prepare a solution, which is preferably filtered through a filter having a pore size of about 0.01 to 1 μm. After mixing, the curable composition is preferably filtered through a filter having a pore size of about 0.01 to 10 μm.

[0238] <Color filter manufacturing method> Methods for producing a colored pattern from the curable composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography is a method in which the curable composition is applied to a substrate and dried to form a colored composition layer, and the colored composition layer is exposed to light through a photomask and developed. In the photolithography, a colored coating film, which is a cured product of the colored composition layer, can be formed by not using a photomask during exposure and / or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.

[0239] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or silica-coated soda lime glass, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. A separate color filter layer, a resin layer, a transistor, a circuit, or the like may be formed on these substrates.

[0240] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be produced as follows. First, the curable composition is applied onto a substrate, and then dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as solvents, thereby obtaining a smooth colored composition layer. Examples of the coating method include spin coating, slit coating, and slit and spin coating. The temperature when drying by heating is preferably 30 to 120° C., more preferably 50 to 110° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying is carried out under reduced pressure, it is preferable to carry out the drying under a pressure of 50 to 150 Pa at a temperature of 20 to 25°C. The thickness of the colored composition layer is not particularly limited and may be appropriately selected depending on the desired thickness of the color filter.

[0241] Next, the colored composition layer is exposed to light through a photomask to form a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended use is used. The light source used for exposure is preferably a light source that emits light with a wavelength of 250 to 450 nm. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples of the light source include a mercury lamp, a light-emitting diode, a metal halide lamp, and a halogen lamp. It is preferable to use an exposure device such as a mask aligner or a stepper, since it is possible to uniformly irradiate the entire exposure surface with parallel light rays and to accurately align the photomask with the substrate on which the colored composition layer is formed.

[0242] A colored pattern is formed on the substrate by bringing the exposed colored composition layer into contact with a developer and developing it. The unexposed portions of the colored composition layer are dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Furthermore, the developer may contain a surfactant. The developing method may be any of a puddle method, a dipping method, a spray method, etc. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferable to wash with water.

[0243] Furthermore, it is preferable to post-bake the obtained colored pattern. The post-bake temperature is preferably 150 to 250° C., more preferably 170 to 245° C., and even more preferably 180 to 240° C. The post-bake time is preferably 1 to 120 minutes, and more preferably 5 to 60 minutes.

[0244] The thickness of the coating film after post-baking is, for example, preferably 3 μm or less, more preferably 2.0 μm or less. The lower limit of the thickness of the coating film is not particularly limited, but is usually 0.3 μm or more, and may be 0.5 μm or more.

[0245] The curable composition of the present invention can provide a curable composition useful for producing a color filter having a good pattern shape. The color filter is useful as a filter for use in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices. [Example]

[0246] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples. In the examples, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

[0247] (Resin synthesis example 1) A flask equipped with a reflux condenser, a dropping funnel, and a stirrer was filled with an appropriate amount of nitrogen to create a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added, followed by heating to 80°C with stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0] 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6A solution of 289 parts of a mixture of decan-9-yl acrylate (content ratio: 1:1) dissolved in 125 parts of propylene glycol monomethyl ether acetate was added dropwise using a dropping pump over approximately 5 hours. Meanwhile, a solution of 33 parts of the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise to the flask over approximately 6 hours using another dropping pump. After the addition was completed, the mixture was maintained at the same temperature for 4 hours and then cooled to room temperature to obtain a polymer (resin (B-1)) solution with a polymer solids content of 35.1%. The weight-average molecular weight Mw of the resulting copolymer (polymer; resin (B-1)) was 9200, the polydispersity was 2.08, and the acid value calculated as solids was 77 mg-KOH / g. The resulting copolymer had the following structural units:

[0248] [ka]

[0249] The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured using a GPC method under the following conditions. Equipment: K2479 (Shimadzu Corporation) Column: SHIMADZU Shim-pack GPC-80M Column temperature: 40°C Solvent: THF (tetrahydrofuran) Flow rate; 1.0mL / min Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

[0250] (Resin synthesis example 2) 277 parts of propylene glycol monomethyl ether acetate was placed in a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube, and the mixture was stirred and heated to 120°C while purging with nitrogen. Next, a monomer mixture consisting of 92.4 parts of 2-ethylhexyl acrylate, 184.9 parts of glycidyl methacrylate, and 12.3 parts of dicyclopentanyl methacrylate, to which 35.3 parts of t-butylperoxy-2-ethylhexanoate (polymerization initiator) had been added, was added dropwise from the dropping funnel to the flask over 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes at 120°C to carry out the copolymerization reaction, producing an addition copolymer. The flask was then purged with air, and 93.7 parts of acrylic acid, 1.5 parts of triphenylphosphine (catalyst), and 0.8 parts of methoquinone (polymerization inhibitor) were added to the addition copolymer solution. The reaction was continued at 110°C for 10 hours. The epoxy groups derived from glycidyl methacrylate reacted with the acrylic acid, cleaving the epoxy groups and simultaneously introducing polymerizable unsaturated bonds into the polymer side chains. Next, 24.2 parts of succinic anhydride were added to the reaction system, and the reaction was continued at 110°C for 1 hour. The hydroxyl groups generated by the cleavage of the epoxy groups reacted with the succinic anhydride, introducing carboxyl groups into the side chains, yielding a polymer. Finally, 383 parts of propylene glycol monomethyl ether acetate was added to the reaction solution, yielding a polymer (Resin (B-2)) solution with a polymer solids content of 40%. The weight-average molecular weight Mw of the resulting copolymer (Polymer; Resin (B-2)) was 6.3 x 10 3 The acid value calculated as solid content was 34 mg-KOH / g.

[0251] [Preparation of Dispersion 1] 12.1 parts of CI Pigment Blue 15:4 (a compound represented by the following formula (A-1)), 3.6 parts of a dispersant (BYK BYKLPN-6919), 5.4 parts of resin (B-1) (solid content equivalent), 11.9 parts of diacetone alcohol, and 67 parts of propylene glycol monomethyl ether acetate were mixed, to which 300 parts of 0.4 mm zirconia beads were added, followed by shaking for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 1.

[0252] [ka]

[0253] [Examples 1 to 8, Comparative Examples 1 and 2] The components shown in Tables 6 and 7 were mixed to obtain each colored curable resin composition. In Tables 6 and 7, the components are as follows: Compound (A-2): A compound represented by the following formula (A-2):

[0254] [ka]

[0255] Resin (B): Resin (B-2) (solid content conversion) Polymerizable compound (C-1): Ethylene oxide-modified dipentaerythritol hexaacrylate ("A-DPH6E" manufactured by Shin-Nakamura Chemical Co., Ltd., a+b+c+d+e+f=6, solid content equivalent)

[0256] [ka]

[0257] Polymerizable compound (C-2): ethylene oxide-modified sorbitol acrylate (prepared by the same method as in Preparation Example 5 of WO 2020 / 218365, a+b+c+d+e+f=18, the number of H2C=CH-CO-* groups in Y is 5; the number of H-* groups is 1, calculated on a solids basis)

[0258] [ka]

[0259] Polymerizable compound (C-3): ethylene oxide-modified sorbitol acrylate (prepared by the same method as in Preparation Example 4 of WO 2020 / 218365, a+b+c+d+e+f=6, the number of H2C=CH-CO-* groups in Y is 3; the number of H-* groups is 3, calculated on a solids basis)

[0260] [ka]

[0261] Polymerizable compound (C-4): Ethylene oxide modified polyglycerin acrylate A compound prepared by adding 264 parts of ethylene oxide to 314 parts of tetraglycerin was reacted with 649 parts of acrylic acid at 85°C for 18 hours, followed by the addition of toluene, a large amount of water, and an amount of sodium hydroxide sufficient to neutralize the unreacted acrylic acid. The organic layer was removed using a separatory funnel and the toluene was removed using an evaporator, yielding an acrylate reaction product of the tetraglycerin ethylene oxide (6 moles) adduct. The viscosity of the product was 440 mPa·s (25°C), and the reaction ratio of acrylic acid calculated from the saponification value was 95% relative to the hydroxyl groups (solids equivalent).

[0262] [ka]

[0263] Polymerizable compound (C-5): Ethylene oxide modified polyglycerin acrylate A compound prepared by adding 528 parts of ethylene oxide to 758 parts of decaglycerin was reacted with 1297 parts of acrylic acid at 85°C for 18 hours. Toluene, a large amount of water, and an amount of sodium hydroxide sufficient to neutralize the unreacted acrylic acid were then added. The organic layer was removed using a separatory funnel and the toluene was removed using an evaporator, yielding an acrylate reaction product of the decaglycerin ethylene oxide (24 moles) adduct. The viscosity of the product was 890 mPa·s (25°C), and the reaction ratio of acrylic acid calculated from the saponification value was 93% relative to the hydroxyl groups (solids equivalent).

[0264] [ka]

[0265] Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine ("PBG-327 (O-acyloxime compound)" manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) Polymerization initiator (D-2): (2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one) (BASF Irgacure-907 (alkylphenone compound)) Solvent (E-1): Diacetone alcohol Solvent (E-2): Propylene glycol monomethyl ether acetate Leveling agent (F-1): Polyether-modified silicone oil ("Toray Silicone SH8400" manufactured by Toray Dow Corning Co., Ltd.)

[0266] [Preparation of Colored Pattern] A colored curable resin composition was applied to a 4-inch silicon substrate by spin coating so that the film thickness after post-baking would be 0.8 μm, and then pre-baked at 80° C. for 2 minutes to obtain a colored composition layer. After cooling, the substrate on which the colored composition layer was formed was exposed to 300 mJ / cm 2 using an exposure machine (NSR-1755i7A; manufactured by Nikon Corporation). 2 The substrate was irradiated with light at an exposure dose of 1.0 μm (based on 365 nm). A photomask on which a 1.0 μm square dot pattern was formed was used. The colored composition layer after light irradiation was immersed and developed in an aqueous developer containing tetramethylammonium hydroxide at 23° C. for 30 seconds, and then washed with water to obtain a colored pattern I after development (before post-baking). Furthermore, the substrate on which colored pattern I was formed was post-baked at 230° C. for 10 minutes to obtain a colored pattern II after post-baking.

[0267] [Evaluation of Hem Pulling of Colored Pattern] The silicon wafer substrates bearing the colored pattern I or II obtained above were observed at a magnification of 30,000x using an electron microscope (S-4100, Hitachi High-Tech Corporation). In a side view of the colored pattern shown in Figure 1, the colored pattern width (CD-half) at a height hb corresponding to 50% of the film thickness la, and the colored pattern width (CD-bottom) at a height h0 corresponding to 0% of the film thickness la were measured, and the (CD-half) / (CD-bottom) ratio was calculated and evaluated based on the following criteria. The results are shown in Tables 6 and 7. 〇: (CD-half) / (CD-bottom) ratio is 100-90% or more △: (CD-half) / (CD-bottom) ratio is 70% or more but less than 90% ×: (CD-half) / (CD-bottom) ratio is less than 70%

[0268] [Table 6]

[0269] [Table 7] [Explanation of symbols]

[0270] la Film thickness hb 50% height of the film thickness la h0 0% height of film thickness la CD-half Colored pattern width at height hb CD-bottom Color pattern width at height h0

Claims

1. The composition includes a resin, a polymerizable compound, and a polymerization initiator, the polymerizable compound comprises a hexitol poly(meth)acrylate, The curable composition for color filters, wherein the hexitol poly(meth)acrylate is a compound represented by the following formula (CA): 【Chemistry 1】 [In formula (CA), Y represents a hydrogen atom or a (meth)acryloyl group, and the number of (meth)acryloyl groups contained in formula (CA) is 1 or more and 6 or less. a to f each independently represent the number of —O—CH 2 —CH 2 — units, and a+b+c+d+e+f is 3 or more and 21 or less.]

2. 2. The curable composition for a color filter according to claim 1, wherein the resin is an alkali-soluble resin.

3. 3. The curable composition for color filters according to claim 1, wherein the resin has a structural unit containing a (meth)acryloyl group in a side chain.

4. The curable composition for color filters according to any one of claims 1 to 3, wherein the polymerization initiator comprises an O-acyloxime compound.

5. A color filter formed from the curable composition for color filters according to any one of claims 1 to 4.

6. A display device comprising the color filter according to claim 5 .

7. A solid-state imaging device comprising the color filter according to claim 5 .

Images