Colored Resin Composition, Color Filter, and Display Device

Abstract

To provide a colored resin composition which enables formation of a color filter having excellent contrast.SOLUTION: A colored resin composition contains a coloring agent and an alkali-soluble resin, wherein the coloring agent contains a compound represented by formula (I), In the formula (I), R1 to R9 are each independently a hydrocarbon group that may have a substituent and has 1 to 20 carbon atoms, a hydrogen atom, a halogen atom, a hydroxy group, a carboxy group or a nitro group, and a methylene group contained in the hydrocarbon group may be replaced with -O- or -CO-. A ring Z represents an aromatic heterocyclic ring.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a colored resin composition, a color filter, and a display device.

Background Art

[0002] Color filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays, and solid-state imaging devices such as CCDs and CMOS sensors are manufactured from colored resin compositions. Various colorants are used as the colored resin composition for forming the color filter. For example, there is known an example in which a compound represented by formula (I-2) having a carbon condensed ring structure is used as the colorant in a coloring composition (Patent Document 1).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

[0004]

Chemical Formula

Summary of the Invention

Problems to be Solved by the Invention

[0005] However, the colored resin composition containing the above compound may not be sufficiently satisfactory in contrast. Therefore, an object of the present invention is to provide a colored resin composition capable of forming a color filter excellent in contrast.

Means for Solving the Problems

[0006] The gist of the present invention is as follows. [1] A colored resin composition containing a colorant and an alkali-soluble resin, wherein the colorant contains a compound represented by formula (I).

Chemical Formula

[0007] According to the present invention, a color filter excellent in contrast can be provided. [Embodiments for Carrying Out the Invention]

[0008] The colored resin composition of the present invention may be for a photoresist and contains a colorant (hereinafter sometimes referred to as colorant (A)) and an alkali-soluble resin (hereinafter sometimes referred to as resin (B)). The colored resin composition of the present invention may contain a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)). The colored resin composition of the present invention may further contain a solvent (hereinafter sometimes referred to as solvent (E)). The colored resin composition of the present invention may further contain a polymerization initiation assistant (hereinafter sometimes referred to as polymerization initiation assistant (D1)). The colored resin composition of the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)). In the present specification, the compounds exemplified as each component can be used alone or in combination of two or more, unless otherwise specified.

[0009] <Colorant (A)> The colorant (A) contains a compound represented by the formula (I) (hereinafter also referred to as compound (I)). Compound (I) may be used alone or in two or more kinds.

[0010] <<Compound (I)>> [Chemical formula]

[0011] [In formula (I), R 1 ~R 9 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, a hydroxy group, a carboxy group or a nitro group, and the methylene group contained in the hydrocarbon group may be replaced by -O- or -CO-. Ring Z represents an aromatic heterocyclic ring.]

[0012] R 1 ~R 9 Examples of the halogen atom represented by R 1 ~R 9 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0013] R 1 ~R 9 Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R 1 ~R 9 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.

[0014] R 1 ~R 9Examples of the saturated or unsaturated chain hydrocarbon group represented by [ [ ID = 4 ] ] include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group, etc.; branched chain alkyl groups such as isopropyl group, (1 - ethyl)propyl group, isobutyl group, sec - butyl group, tert - butyl group, (1 - ethyl)butyl group, (2 - ethyl)butyl group, (1 - propyl)butyl group, isopentyl group, neopentyl group, tert - pentyl group, (2 - methyl)pentyl group, (1 - ethyl)pentyl group, (3 - ethyl)pentyl group, (1 - propyl)pentyl group, (1 - butyl)pentyl group, isohexyl group, (2 - methyl)hexyl group, (5 - methyl)hexyl group, (2 - ethyl)hexyl group, (1 - butyl)hexyl group, (1 - pentyl)hexyl group, (2 - methyl)heptyl group, (2 - ethyl)heptyl group, (3 - ethyl)heptyl group, (1 - hexyl)heptyl group, (2 - methyl)octyl group, (2 - ethyl)octyl group, (1 - heptyl)octyl group, (2 - ethyl)nonyl group, (1 - octyl)nonyl group, etc.; alkenyl groups such as vinyl group, 1 - propenyl group, 2 - propenyl group (allyl group), (1 - methyl)ethenyl group, 2 - butenyl group, 3 - butenyl group, 1,3 - butadienyl group, (1-(2 - propenyl))ethenyl group, (1,2 - dimethyl)propenyl group, 2 - pentenyl group, etc. The number of carbon atoms of the saturated chain hydrocarbon group is preferably 1 to 18, more preferably 2 to 15, and even more preferably 3 to 12. Also, the number of carbon atoms of the unsaturated chain hydrocarbon group is preferably 2 to 18, more preferably 2 to 15, and even more preferably 3 to 12.

[0015] R 1 ~R 9Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group; cycloalkenyl groups such as cyclohexenyl group (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl group, cyclooctenyl group; norbornyl group, adamantyl group, bicyclo[2.2.2]octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 15, more preferably 3 to 12.

[0016] R 1 ~R 9 Examples of the aromatic hydrocarbon group represented by include phenyl group, 1-naphthyl group, 2-naphthyl group, phenanthryl group, anthryl group, pyrenyl group and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 15, more preferably 6 to 12.

[0017] R 1 ~R 9The hydrocarbon group represented by may be a group formed by combining two or more of the above-mentioned linear hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups as long as the upper limit of the number of carbon atoms is 20 or less. Such a group may be, for example, a group formed by combining an aromatic hydrocarbon group and at least one group selected from a linear hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. In the hydrocarbon group formed by the combination, the linear hydrocarbon group may be combined as a divalent group (for example, an alkanediyl group).Examples of hydrocarbon groups formed by combination include aralkyl groups such as benzyl group, phenethyl group, 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group); arylalkynyl groups such as phenylethynyl group; o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, 2,3-diisopropylphenyl group, 2,4-diisopropylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisopropylphenyl group, 2,4,6-triisopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 2,6-di(tert-butyl)phenyl group, 3,5-di(tert-butyl)phenyl group, 3,6-di(tert-butyl)phenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 4-pentylphenyl group, 4-octylphenyl group, 4-(2,4,4-trimethyl-2-pentyl)phenyl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecylphenyl group and other alkylaryl groups; aryl groups bonded with alkanediyl groups such as 2,3-dihydro-4-indenyl group, 1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 8-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, 3-methyl-5,6,7,8-tetrahydro-2-naphthyl group, 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group; aryl groups bonded with one or more aryl groups such as biphenylyl group, terphenylyl group; cyclohexylmethylphenyl group, benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group and the like.Further, the hydrocarbon group may be, for example, a hydrocarbon group formed by a combination of a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples thereof include an alicyclic hydrocarbon group to which one or more alkyl groups such as 1-methylcyclopropyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 4-cyclohexylcyclohexyl group are bonded; an alkyl group to which one or more alicyclic hydrocarbon groups such as cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group, adamantylmethyl group are bonded, and the like. The carbon number of a group formed by combining two or more of a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 15.

[0018] R 1 ~R 9Examples of the substituent that the hydrocarbon group having 1 to 20 carbon atoms represented by may have include, for example, a halogen atom; a nitrile group; a nitro group; an amino group; a hydroxy group; an alkoxy group having 1 to 20 carbon atoms such as a methoxy group and an ethoxy group; an aryloxy group having 6 to 20 carbon atoms such as a phenyloxy group, a 1-naphthyloxy group, and a 2-naphthyloxy group; a thiol group; an alkylthio group having 1 to 20 carbon atoms such as a methylthio group and an ethylthio group; an allylthio group; an arylthio group having 6 to 20 carbon atoms such as a phenylthio group, a 1-naphthylthio group, and a 2-naphthylthio group; a sulfoxy group; an alkylsulfoxy group having 1 to 20 carbon atoms such as a methylsulfoxy group and an ethylsulfoxy group; an arylsulfoxy group having 6 to 20 carbon atoms such as a phenylsulfoxy group, a 1-naphthylsulfoxy group, and a 2-naphthylsulfoxy group; a silyl group; a boryl group; an alkylamino group having 1 to 20 carbon atoms such as a monomethylamino group, a dimethylamino group, a trimethylamino group, a monoethylamino group, a diethylamino group, and a triethylamino group; an arylamino group having 6 to 20 carbon atoms such as a monophenylamino group, a diphenylamino group, and a triphenylamino group; an aralkylamino group having 7 to 20 carbon atoms such as a benzylamino group; a carboxy group; a carbamoyl group; an alkylcarbonyl group having 2 to 20 carbon atoms such as an acetyl group and a propionyl group; an arylcarbonyl group having 7 to 20 carbon atoms such as a benzoyl group, a 1-naphthylcarbonyl group, and a 2-naphthylcarbonyl group; an alkoxycarbonyl group having 2 to 20 carbon atoms such as a methoxycarbonyl group and an ethoxycarbonyl group; an aryloxycarbonyl group having 7 to 20 carbon atoms such as a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group, and a 2-naphthyloxycarbonyl group; and the like.

[0019] R 1 ~R 9 The methylene group (-CH2-) contained in the hydrocarbon group having 1 to 20 carbon atoms represented by may be replaced by -O- or -CO-.

[0020] R 1 ~R 9When -CH2- contained in the hydrocarbon group represented by is replaced by -O- or -CO-, the number thereof may be one or two or more. When -CH2- contained in the hydrocarbon group is replaced by -O- or -CO-, the number of carbon atoms before replacement is defined as the number of carbon atoms of the hydrocarbon group. R 1 ~R 9 Specific examples of the group in which -CH2- contained in the hydrocarbon group represented by is replaced by -O- or -CO- include groups represented by the following formulas (Y-1) to (Y-25). * represents a bond.

[0021] [Chemical formula]

[0022] R 1 is preferably a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, more preferably an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, still more preferably an aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and even more preferably a branched alkyl group having 3 to 16 carbon atoms.

[0023] R 2 ~R 9 is preferably a hydrogen atom.

[0024] Ring Z represents an aromatic heterocyclic ring. The aromatic heterocyclic ring represented by Ring Z may be a monocyclic ring or a polycyclic ring. The number of carbon atoms of the aromatic heterocyclic ring is preferably 3 to 20, more preferably 3 to 18, and particularly preferably 3 to 12. The aromatic heterocyclic ring is preferably a 5- to 12-membered ring, more preferably a 5- to 10-membered ring, and still more preferably a 5- to 9-membered ring.

[0025] Ring Z preferably contains a hetero atom and is an aromatic heterocyclic ring containing one or more selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. Ring Z may contain two or more heteroatoms, may contain two or more nitrogen atoms, oxygen atoms, or sulfur atoms respectively, may be a combination of nitrogen atoms and oxygen atoms, nitrogen atoms and sulfur atoms, or oxygen atoms and sulfur atoms, or may be a combination of nitrogen atoms, oxygen atoms and sulfur atoms.

[0026] Examples of the heterocyclic ring containing a nitrogen atom include 5-membered ring unsaturated heterocycles such as pyrrole, 1-methylpyrrole, 2,5-dimethylpyrrole and other pyrroles, pyrazole, 1-methylpyrazole, 2-methylpyrazole, 3-methylpyrazole, 4-methylpyrazole, 5-methylpyrazole and other pyrazoles, imidazole, 1,2,3-triazole and 1,2,4-triazole and other imidazoles; 6-membered ring unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, 6-methylpyrimidine and other pyrimidines, pyrazine and 1,3,5-triazine; Fused bicyclic heterocycles such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline and other quinoxalines, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine; Fused tricyclic heterocycles such as carbazole, acridine and phenazine; and the like.

[0027] Examples of the heterocyclic ring containing an oxygen atom include Lactone-based heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone; 5-membered ring unsaturated heterocycles such as furan, 2,3-dimethylfuran, 2,5-dimethylfuran; 6-membered ring unsaturated heterocycles such as 2H-pyran, 4H-pyran; Condensed bicyclic heterocycles such as benzofuran, isobenzofuran, benzopyran, benzopyran such as 4-methylbenzopyran, benzodioxole, 1,3-benzodioxole, benzodioxane, chroman and isochroman; Condensed tricyclic heterocycles such as xanthene and dibenzofuran; etc. can be mentioned.

[0028] As the heterocycle containing a sulfur atom, 5-membered ring unsaturated heterocycles and 6-membered ring unsaturated heterocycles such as thiophene, 3-methylthiophene, thiophene such as 2-carboxythiophene, thiopyran such as 2H-thiopyran and 4H-thiopyran, benzothiopyran such as benzotetrahydrothiopyran; Condensed bicyclic heterocycles such as benzothiopyran and benzotetrahydrothiopyran, and condensed bicyclic heterocycles such as benzothiophene; etc. Condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; etc. can be mentioned.

[0029] As the heterocycle containing a nitrogen atom and an oxygen atom, Monocyclic unsaturated heterocycles such as isothiazole, oxazole, oxazole such as 4-methyloxazole, isoxazole such as 2-methylisoxazole, 3-methylisoxazole, 4-methylisoxazole, 5-methylisoxazole; Condensed bicyclic heterocycles such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, benzimidazoline; Condensed tricyclic heterocycles such as phenoxazine; etc. can be mentioned.

[0030] As the heterocycle containing a nitrogen atom and a sulfur atom, 5-membered ring unsaturated heterocycles such as thiazole; Condensed bicyclic heterocycles such as benzothiazole; Condensed tricyclic heterocycles such as phenothiazine; etc. can be mentioned.

[0031] Incidentally, the bonding position of the above complex ring is the part where any two hydrogen atoms contained in each complex ring are eliminated.

[0032] The aromatic heterocyclic ring may have a substituent, and examples of the substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, a cyano group, a nitro group, a hydroxy group, a substituted or unsubstituted amino group, an alkoxy group having 1 to 8 carbon atoms, and the like.

[0033] Among them, the aromatic heterocyclic ring is preferably an aromatic heterocyclic ring containing a nitrogen atom, more preferably a 5-membered ring unsaturated heterocyclic ring containing a nitrogen atom, and even more preferably imidazole.

[0034] As shown in Tables 1 to 5, the compound represented by the formula (I) is preferably a compound represented by the formulas (Ia-1) to (Ia-280).

[0035] [Table 1]

[0036] [Table 2]

[0037] [Table 3]

[0038] [Table 4]

[0039] [Table 5]

[0040] In Tables 1 to 5, (D-1) to (D-16), (G-1) to (G-24), and (Z-1) to (Z-7) are the same as the structures shown below. The * of each group represents a bond.

[0041]

Chemical formula

[0042]

Chemical formula

[0043]

Chemical formula

[0044] Among them, the compounds represented by formula (Ia-1) to formula (Ia-48), formula (Ia-113) to formula (Ia-184) are preferred, more preferably the compounds represented by formula (Ia-13), the compounds represented by formula (Ia-29), and the compounds represented by formula (Ia-45), and even more preferably the compounds represented by formula (Ia-45) (compound (I-4) described later).

[0045] The compound represented by formula (I) may be produced by a conventionally known method, for example, synthesized according to the method described in Angew.Chem.Int.Ed.1999, 38.201-203.

[0046] <<Colorant (A1)>> The colored resin composition of the present invention may contain, as the colorant (A), dyes other than compound (I) (hereinafter sometimes referred to as dye (A1-1)) and / or pigments (hereinafter sometimes referred to as pigment (A1-2)) (hereinafter, dye (A1-1) and pigment (A1-2) may be collectively referred to as colorant (A1)). These may be used alone or in combination of two or more.

[0047] The dye (A1-1) is not particularly limited as long as it does not contain the compound (I), and known dyes can be used. For example, solvent dyes, acid dyes, direct dyes, mordant dyes, etc. can be mentioned. As the dye, for example, compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in the Dyeing Notes (Color Dyeing Co., Ltd.) can be mentioned. Further, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene 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, etc. can be mentioned. Among these, organic solvent-soluble dyes are preferred.

[0048] As the pigment (A1-2), as long as it does not contain the compound (I), it is not particularly limited, and known pigments can be used. For example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists) can be mentioned. Examples of the pigments classified as pigments include yellow pigments such as C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231, etc.; orange pigments such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.; red pigments such as C.I. Pigment Red 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, etc.; blue pigments such as C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc.; Violet pigments such as C.I. Pigment Violet 1, 19, 23, 32, 36, 38, etc.; Green pigments such as C.I. Pigment Green 7, 36, 58, 59, 62, 63, etc.; Brown pigments such as C.I. Pigment Brown 23, 25, etc.; Black pigments such as C.I. Pigment Black 1, 7, etc. may be mentioned.

[0049] As the colorant (A1), yellow, red or green dyes and pigments are preferred.

[0050] The colorant (A1) may, if necessary, be subjected to surface treatment using rosin treatment, derivatives into which an acidic group or a basic group has been introduced, etc., graft treatment onto the surface of the colorant (A1) using a polymer compound, etc., micronization treatment by the sulfuric acid micronization method, etc., washing treatment with an organic solvent, water, etc. for removing impurities, removal treatment by an ion exchange method for ionic impurities, etc. The particle size of the colorant (A1) is preferably substantially uniform.

[0051] When the colorant (A) further contains the colorant (A1), the lower limit of the content of the total amount of the compound (I) in the colorant (A) is, for example, 1% by mass or more, preferably 2% by mass or more, more preferably 10% by mass or more, still more preferably 25% by mass or more, particularly preferably 50% by mass or more with respect to the total amount of the colorant (A). On the other hand, when the colorant (A) further contains the colorant (A1), the upper limit of the content of the total amount of the compound (I) in the colorant (A) is, for example, less than 100% by mass with respect to the total amount of the colorant (A).

[0052] When the colored resin composition contains a solvent (E), a colorant-containing liquid (which may also be referred to as a coloring composition) containing a colorant (A) and a solvent (E) may be prepared in advance, and then the colored resin composition may be prepared using the colorant-containing liquid. When the colorant (A) is insoluble in the solvent (E), for example, when the colorant (A) contains a pigment (A1-2), the colorant-containing liquid can be prepared by dispersing and mixing the colorant (A) in the solvent (E). The colorant-containing liquid may contain part or all of the solvent (E) contained in the colored resin composition.

[0053] The content rate of the solid content in the colorant-containing liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, still more preferably 0.1% by mass or more and 99% by mass or less, even more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1% by mass or more and 50% by mass or less, based on the total amount of the colorant-containing liquid.

[0054] The colorant (A) can be made to be in a state of being uniformly dispersed in the solution by performing a dispersion treatment while containing a dispersant. When two or more kinds of the colorant (A) are used in combination, each may be dispersed separately, or a plurality of kinds may be mixed and dispersed.

[0055] Examples of the dispersant include surfactants, and any of cationic, anionic, nonionic, and amphoteric surfactants may be used. Specifically, surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants can be mentioned. These dispersants may be used alone or in combination of two or more. Examples of the dispersant represented by the trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Inc.), Disperbyk (registered trademark) (manufactured by BYK-Chemie GmbH), BYK (registered trademark) (manufactured by BYK-Chemie GmbH), etc. As the dispersant, the resin (B) described later may also be used.

[0056] When a dispersant is used, the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10,000 parts by mass or less, preferably 5 parts by mass or more and 5,000 parts by mass or less, more preferably 10 parts by mass or more and 1,000 parts by mass or less, and still more preferably 15 parts by mass or more and 800 parts by mass or less with respect to 100 parts by mass of the colorant (A). When the amount of the dispersant used is within the above range, a colorant-containing liquid with a more uniform dispersion state tends to be obtained.

[0057] The content of the colorant (A) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass or less, and still more preferably 1% by mass or more and 30% by mass or less with respect to the total amount of the solid content of the colored resin composition. When the content of the colorant (A) is within the above range, the color density when used as a color filter is sufficient, and since the necessary amount of the resin (B) can be contained in the composition, it is possible to form a pattern with sufficient mechanical strength, which is preferable. Here, the "total amount of solid content" in this specification refers to the amount obtained by removing the content of the solvent from the total amount of the colored resin composition. The total amount of the solid content and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0058] <Resin (B)> Unlike the thermoplastic resin, the resin (B) is not particularly limited as long as it is used for forming a photoresist, but it is preferably an alkali-soluble resin, and more preferably an alkali-soluble resin having a carboxylic acid.

[0059] Examples of the resin (B) include the following resins [K1] to [K6]. Resin [K1]; a copolymer having a structural unit derived from at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)") and a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenic unsaturated bond; Resin [K2]; a copolymer having a structural unit derived from (a), a structural unit derived from (b), and a structural unit 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 a structural unit derived from (a) and a structural unit derived from (c); Resin [K4]; a copolymer having a structural unit obtained by adding (b) to a structural unit derived from (a) and a structural unit derived from (c); Resin [K5]; a copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and a structural unit derived from (c); Resin [K6]; a copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic anhydride and a structural unit derived from (c).

[0060] Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o -, m -, 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; Bicyclic unsaturated 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 - 6 - methylbicyclo[2.2.1]hept - 2 - ene, and 5 - carboxy - 6 - ethylbicyclo[2.2.1]hept - 2 - ene; Carboxylic anhydrides such as anhydrides of the above - mentioned unsaturated dicarboxylic acids excluding fumaric acid and mesaconic acid; Unsaturated mono-[(meth)acryloyloxyalkyl] esters of polyvalent carboxylic acids having a valence of 2 or more, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid; and the like. Among these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoints of copolymerization reactivity and solubility of the resulting resin in an aqueous alkali solution. In the present specification, “(meth)acrylic acid” represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Expressions such as “(meth)acryloyl” and “(meth)acrylate” also have the same meaning.

[0061] Monomer (b) refers to 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 (oxolane ring)) and an ethylenically unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0062] Examples of monomer (b) include monomers having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b1)”), monomers having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b2)”), monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b3)”), and the like.

[0063] Examples of monomer (b1) include monomers having a structure obtained by epoxidizing an unsaturated aliphatic hydrocarbon (hereinafter sometimes referred to as “monomer (b1-1)”), and monomers having a structure obtained by epoxidizing an unsaturated alicyclic hydrocarbon (hereinafter sometimes referred to as “monomer (b1-2)”).

[0064] As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable. Specific examples of the monomer (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(glycidyloxymethyl)styrene, 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, 2,4,6-tris(glycidyloxymethyl)styrene and the like.

[0065] Examples of the monomer (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) M100; manufactured by Daicel Corporation), a compound represented by formula (BI) and a compound represented by formula (BII).

[0066] [Chemical formula]

[0067] [In formula (BI) and formula (BII), R a and R bEach independently 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 a and X b Each independently represents a single bond, *-R c -, *-R c -O-, *-R c -S- or is *-R c -NH-. R c represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.

[0068] 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, a tert-butyl group, and the like.

[0069] Examples of the alkyl group 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, a 4-hydroxybutyl group, and the like.

[0070] R a and R b Preferably include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, more preferably include a hydrogen atom, a methyl group.

[0071] 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, a hexane-1,6-diyl group, and the like.

[0072] X a and Xb Examples thereof preferably include a single bond, a methylene group, an ethylene group, a *-CH2-O- group (* represents a bonding hand with O), and a *-CH2CH2-O- group, and more preferably include a single bond and a *-CH2CH2-O- group (* represents a bonding hand with O).

[0073] Examples of the compound represented by formula (BI) include compounds represented by any of formula (BI-1) to formula (BI-15). Among them, compounds represented by formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9), and formula (BI-11) to formula (BI-15) are preferred, and compounds represented by formula (BI-1), formula (BI-7), formula (BI-9), and formula (BI-15) are more preferred.

[0074]

Chemical formula

[0075] Examples of the compound represented by formula (BII) include compounds represented by any of formula (BII-1) to formula (BII-15). Among them, preferably, compounds represented by formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9), and formula (BII-11) to formula (BII-15) are included, and more preferably, compounds represented by formula (BII-1), formula (BII-7), formula (BII-9), and formula (BII-15) are included.

[0076]

Chemical formula

[0077] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of the compound represented by formula (BI) and the compound represented by formula (BII). When these are used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and still more preferably 20:80 to 80:20 on a molar basis.

[0078] As the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. Examples of the monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, 3-ethyl-3-(meth)acryloyloxyethyloxetane and the like.

[0079] As the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate and the like.

[0080] Examples of the monomer (c) include 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, tricyclo[5.2.1.0 2,6Decan-8-yl (meth)acrylate (in the art, it is commonly known as "dicyclopentanyl (meth)acrylate". Also, it may be referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 Decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 Decen-8-yl (meth)acrylate (in the art, it is commonly known as "dicyclopentenyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 Decen-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate, etc. (meth)acrylic acid esters; 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-methoxy-bicyclo[2.2.1]hept-2-ene, 5-ethoxy-bicyclo[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-dimethoxy-bicyclo[2.2.1]hept-2-ene, 5,6-diethoxy-bicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; Dicarbonylimide 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; Vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene; and the like. Among these, from the viewpoints of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 2,6 decane-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 decene-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 decene-9-yl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and benzyl (meth)acrylate are preferable.

[0081] In resin [K1], the ratio of the structural units derived therefrom is among all the structural units constituting resin [K1], Structural units derived from (a); 2 to 60 mol% Structural units derived from (b); 40 to 98 mol% It is preferably such that, Structural units derived from (a); 10 to 50 mol% Structural units derived from (b); 50 to 90 mol% It is more preferably such that. When the ratio of the structural units of resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained optical filter tend to be excellent.

[0082] The resin [K1] can be produced, for example, with reference to the methods described in the document "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, issued on March 1, 1972) and the cited references described in said document.

[0083] Specifically, examples of the method include putting predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. into a reaction vessel, creating a deoxygenated atmosphere by substituting oxygen with, for example, nitrogen, and heating and maintaining the temperature while stirring. Note that the polymerization initiator, solvent, etc. used here are not particularly limited, and those commonly used in the art can be used. For example, as the polymerization initiator, azo compounds (such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (such as benzoyl peroxide, etc.) can be mentioned. As the solvent, any solvent that can dissolve each monomer may be used, and examples include the solvents described later as the solvent (E) of the colored resin composition of the present invention.

[0084] Note that the obtained copolymer may be used as the reaction solution as it is, or a concentrated or diluted solution may be used, or a solid (powder) taken out by a method such as reprecipitation may be used. In particular, by using the solvent contained in the colored resin composition of the present invention as the solvent during this polymerization, the reaction solution can be directly used for the preparation of the colored resin composition of the present invention, so the manufacturing process of the colored resin composition of the present invention can be simplified.

[0085] In the resin [K2], the ratio of the structural units derived from each is, among all the structural units constituting the resin [K2], 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% It is preferably that, 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 it is. When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the resulting optical filter tend to be excellent.

[0086] The resin [K2] can be produced, for example, in the same manner as the method described as the production method of the resin [K1].

[0087] In the resin [K3], the ratio of the structural units derived from each is among all the structural units constituting the resin [K3], (a) Structural units derived from; 2 to 60 mol% (c) Structural units derived from; 40 to 98 mol% It is preferable that it is, (a) Structural units derived from; 10 to 50 mol% (c) Structural units derived from; 50 to 90 mol% It is more preferable that it is. The resin [K3] can be produced, for example, in the same manner as the method described as the production method of the resin [K1].

[0088] The resin [K4] can be produced by obtaining a copolymer of (a) and (c) and adding the cyclic ether having 2 to 4 carbon atoms that (b) has to the carboxylic acid and / or carboxylic anhydride that (a) has. First, a copolymer of (a) and (c) is produced in the same manner as the method described as the production method of the resin [K1]. In this case, it is preferable that the ratio of the structural units derived from each is the same as the ratio given for the resin [K3].

[0089] Next, a cyclic ether having 2 to 4 carbon atoms that (b) has is reacted with a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer. Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced from nitrogen to air, and (b), a reaction catalyst for the reaction of a carboxylic acid or carboxylic anhydride with a cyclic ether (such as tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (such as hydroquinone, etc.) are put into the flask, and reacted, for example, at 60 to 130 °C for 1 to 10 hours to produce resin [K4]. The usage amount of (b) is preferably 5 to 80 mol, more preferably 10 to 75 mol, relative to 100 mol of (a). By setting it within this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern tend to be good. Since the cyclic ether has high reactivity and unreacted (b) hardly remains, (b1) is preferable as (b) used for resin [K4], and (b1-1) is more preferable. The usage amount of the reaction catalyst is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b), and (c). The usage amount of the polymerization inhibitor is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b), and (c). 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 polymerization, etc. Note that, similar to 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 polymerization, etc.

[0090] As the first step, resin [K5] is obtained in the same manner as the production method of resin [K1] described above to obtain a copolymer of (b) and (c). Similar to the above, the obtained copolymer may be used as the reaction solution as it is, or a concentrated or diluted solution may be used, or a solid (powder) taken out by a method such as reprecipitation may be used. The ratios of the structural units derived from (b) and (c) are respectively structural units derived from (b); 5 to 95 mol% structural units derived from (c); 5 to 95 mol% preferably as follows Structural unit derived from (b); 10 to 90 mol% Structural unit derived from (c); 10 to 90 mol% It is more preferable that it is as follows.

[0091] Furthermore, under the same conditions as the production method of resin [K4], by reacting the cyclic ether derived from (b) in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride that (a) has, resin [K5] can be obtained. The amount of (a) used for reacting with the copolymer is preferably 5 to 80 mol with respect to 100 mol of (b). Since the cyclic ether has high reactivity and unreacted (b) hardly remains, (b1) is preferable as (b) used for resin [K5], and (b1-1) is more preferable.

[0092] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic anhydride. The carboxylic anhydride is reacted with the hydroxy group generated by the reaction of the cyclic ether and the carboxylic acid or carboxylic anhydride. Examples of the carboxylic anhydride include 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, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride and the like. The amount of the carboxylic anhydride used is preferably 0.5 to 1 mol with respect to 1 mol of the amount of (a) used.

[0093] Specific examples of resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate / (meth)acrylic acid copolymer and the like, such as resin [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.02,6 Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer and other resins [K2]; Benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and other resins [K3]; Resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer and other resins [K4]; Resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate, resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate and other resins [K5]; Resins obtained by reacting tetrahydrophthalic anhydride with a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate and other resins [K6], etc.

[0094] Resin (B) is more preferably resin [K1] and resin [K2], and particularly preferably resin [K1].

[0095] The weight average molecular weight (Mw) of resin (B) in terms of polystyrene is preferably 1,000 or more and 100,000 or less, more preferably 2,000 or more and 50,000 or less, and even more preferably 3,000 or more and 30,000 or less. When the weight average molecular weight is within the above range, the solubility of the unexposed portion in the developer is high, and the remaining film ratio and hardness of the obtained pattern tend to be high. The dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1 or more and 6 or less, more preferably 1.001 or more and 4 or less, and even more preferably 1.01 or more and 4 or less.

[0096] The acid value (solid content conversion value) of the resin (B) is preferably 10 mg-KOH / g or more and 300 mg-KOH / g or less, more preferably 20 mg-KOH / g or more and 250 mg-KOH / g or less, even more preferably 25 mg-KOH / g or more and 200 mg-KOH / g or less, still more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, and particularly preferably 60 mg-KOH / g or more and 135 mg-KOH / g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0097] The content of the resin (B) is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and even more preferably 15 to 30% by mass in 100% by mass of the solid content of the colored resin composition. When the content of the resin (B) is within the above range, the solubility of the unexposed portion in the developer tends to be high.

[0098] <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), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and preferably (meth)acrylate compounds.

[0099] Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc., as well as the above-mentioned monomers (a), monomers (b), and monomers (c).

[0100] Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6 - hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3 - methylpentane diol di(meth)acrylate.

[0101] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2 - (meth)acryloyloxyethyl) isocyanurate, ethylene glycol - modified pentaerythritol tetra(meth)acrylate, ethylene glycol - modified dipentaerythritol hexa(meth)acrylate, propylene glycol - modified pentaerythritol tetra(meth)acrylate, propylene glycol - modified dipentaerythritol hexa(meth)acrylate, caprolactone - modified pentaerythritol tetra(meth)acrylate, and caprolactone - modified dipentaerythritol hexa(meth)acrylate. Preferably, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are mentioned.

[0102] The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 70 or more and 3,500 or less, still more preferably 100 or more and 3,000 or less, even more preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

[0103] The content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, and still more preferably 20% by mass or more and 70% by mass or less, based on the total amount of the solid content of the colored resin composition.

[0104] <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 can initiate polymerization, and known polymerization initiators can be used.

[0105] Examples of the polymerization initiator (D) include O-acyl oxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0106] Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine. Further, as the O-acyl oxime compound, commercially available products such as Irgacure (registered trademark) OXE01 and OXE02 (manufactured by BASF) and N-1919 (manufactured by ADEKA Corporation) may be used. Among them, as the O-acyl oxime compound, at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine is more preferable.

[0107] Examples of the alkylphenone compound 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, and the like. As the alkylphenone compound, commercially available products such as Irgacure (registered trademark) 369, 907, 379 (manufactured by BASF) may also be used. Examples of the alkylphenone compound 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.

[0108] 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, JP-A-6-75373, etc.), 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, JP-A-62-174204, etc.), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboxyalkoxy groups (see, for example, JP-A-7-10913, etc.).

[0109] 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, 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, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0110] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

[0111] Furthermore, 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 initiation aid (D1) (particularly amines) described below.

[0112] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds, and more preferably a polymerization initiator containing an O-acyl oxime compound.

[0113] The content of the polymerization initiator (D) is preferably 0.1 part by mass or more and 30 parts by mass or less, and more preferably 1 part by mass or more and 20 parts by mass or less, based on 100 parts by mass of the total amount of the total resin (B) and the polymerizable compound (C) contained in the colored resin composition. When the content of the polymerization initiator (D) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, so that the productivity of the color filter is improved.

[0114] <Polymerization initiation aid (D1)> The polymerization initiation aid (D1) is a compound or a sensitizer used to promote the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D). When the polymerization initiation aid (D1) is included, it is usually used in combination with the polymerization initiator (D).

[0115] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxy anthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0116] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone. Among them, 4,4'-bis(diethylamino)benzophenone is preferable. Further, as the amine compound, a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

[0117] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0118] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0119] Examples of the carboxylic acid compound include phenylsulfanyl acetic acid, methylphenylsulfanyl acetic acid, ethylphenylsulfanyl acetic acid, methylethylphenylsulfanyl acetic acid, dimethylphenylsulfanyl acetic acid, methoxyphenylsulfanyl acetic acid, dimethoxyphenylsulfanyl acetic acid, chlorophenylsulfanyl acetic acid, dichlorophenylsulfanyl acetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0120] When using these polymerization initiation aids (D1), the content is preferably 0.1 part by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, based on 100 parts by mass of the total amount of the entire resin (B) and the polymerizable compound (C) contained in the colored resin composition.

[0121] <Solvent (E)> The solvent (E) is not particularly limited, and solvents commonly used in the art can be used. Examples of the solvent (E) include ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like. These solvents may be used in combination of two or more.

[0122] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, 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.

[0123] 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, methyl anisole, and the like.

[0124] Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate, and the like.

[0125] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0126] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0127] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0128] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0129] As the solvent (E), propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and cyclohexanone are preferable.

[0130] When the solvent (E) is included, the content of the solvent (E) is usually 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 95% by mass or less, still more preferably 70% by mass or more and 95% by mass or less, and even more preferably 75% by mass or more and 90% by mass or less, based on the total amount of the colored resin composition. In other words, the total amount of the solid content of the colored resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 50% by mass or less, still more preferably 5% by mass or more and 30% by mass or less, and even more preferably 10% by mass or more and 25% by mass or less. When the content of the solvent (E) is within the above range, the flatness during coating becomes good, and the display characteristics tend to be good because the color density is not insufficient when forming the color filter.

[0131] <Leveling agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorosurfactants, and silicone surfactants having fluorine atoms. These may have a polymerizable group in the side chain.

[0132] Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan G.K.) etc. are included.

[0133] Examples of the fluorosurfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.) etc. are included.

[0134] Examples of the silicone surfactant having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation) etc. are included.

[0135] When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and still more preferably 0.005% by mass or more and 0.1% by mass or less with respect to the total amount of the colored resin composition. Note that the content of the pigment dispersant is not included in this content. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0136] <Other components> The colored resin composition may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, etc., as necessary.

[0137] <Method for producing colored resin composition> The colored resin composition can be prepared by mixing the colorant (A), the resin (B), the polymerizable compound (C) used as necessary, the polymerization initiator (D), the solvent (E), the leveling agent (F), and other components. The mixing can be carried out by known or conventional devices and conditions. The colorant (A) may be mixed with a part or all of the solvent (E) in advance and used in a dispersed state using a bead mill or the like until the average particle diameter becomes about 0.2 μm or less. It is preferable to use it in a dispersed state. At this time, the dispersant, a part or all of the resin (B) may be blended as necessary. Also, the colorant (A) may be used in a state of being dissolved in a part or all of the solvent (E) in advance. The target colored resin composition can be prepared by mixing the remaining components into the colorant-containing liquid thus obtained so as to have a predetermined concentration.

[0138] <Method for producing color filter> A color filter, which may be a color conversion layer, can be formed from the colored resin composition. Examples of the method for forming a colored pattern include a photolithography method, an inkjet method, a printing method, etc. Among these, the photolithography method is preferable. The photolithography method is a method in which the colored resin composition is applied to a substrate, dried to form a colored resin composition layer, and the colored resin composition layer is exposed and developed through a photomask. In the photolithography method, a colored coating film, which is a cured product of the colored resin composition layer, can be formed by not using a photomask and / or not developing during exposure. The colored pattern or colored coating film formed in this way is the color filter of the present invention.

[0139] The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose, application, etc. For example, it is 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and more preferably 0.5 μm or more and 6 μm or less.

[0140] As the substrate, a glass plate such as quartz glass, borosilicate glass, aluminosilicate glass, or soda lime glass with a silica-coated surface, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or a substrate with an aluminum, silver, silver / copper / palladium alloy thin film, etc. formed thereon is used. Another color filter layer, resin layer, transistor, circuit, etc. may be formed on these substrates.

[0141] The formation of each color pixel by the photolithography method can be performed with known or conventional devices and conditions. For example, it can be produced as follows. First, the colored resin composition is applied onto the substrate, and volatile components such as a solvent are removed by heating and drying (pre-baking) and / or drying under reduced pressure to obtain a smooth colored resin composition layer. Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, etc. When performing heat drying, the temperature is preferably 30°C or higher and 120°C or lower, more preferably 50°C or higher and 110°C or lower. Also, the heating time is preferably 10 seconds or longer and 60 minutes or shorter, more preferably 30 seconds or longer and 30 minutes or shorter. When performing vacuum drying, it is preferably carried out under a pressure of 50 Pa or higher and 150 Pa or lower in a temperature range of 20°C or higher and 25°C or lower. The film thickness of the colored resin composition layer is not particularly limited and may be appropriately selected according to the film thickness of the target color filter.

[0142] Next, the colored resin composition layer is exposed through a photomask for forming the target colored pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the intended use is used. Also, since it is possible to irradiate the entire exposure surface with parallel light rays uniformly and to perform accurate alignment between the photomask and the substrate on which the colored resin composition layer is formed, it is preferable to use an exposure apparatus such as a mask aligner and a stepper.

[0143] As the light source used for exposure, a light source that generates light with a wavelength of 250 nm or longer and 450 nm or shorter is preferable. For example, light with a wavelength of less than 350 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, near 408 nm, or near 365 nm may be selectively extracted using a band-pass filter that extracts these wavelength ranges. Specifically, a mercury lamp, a light-emitting diode, a metal halide lamp, a halogen lamp, etc. may be mentioned.

[0144] By bringing the exposed colored resin composition layer into contact with a developer for development, a colored pattern is formed on the substrate. By development, the unexposed portion of the colored resin composition layer is dissolved and removed by the developer. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration in the aqueous solution of these alkaline compounds is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Further, the developer may contain a surfactant. The development method may be any of a paddle method, a dipping method, a spray method, etc. Further, the substrate may be tilted at an arbitrary angle during development. The developed substrate is preferably washed with water.

[0145] Furthermore, it is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably 150°C or higher and 250°C or lower, more preferably 160°C or higher and 240°C or lower. The post-baking time is preferably 1 minute or longer and 120 minutes or shorter, more preferably 10 minutes or longer and 60 minutes or shorter.

[0146] <Display device> The color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state imaging device, and particularly useful as a color filter used in an organic EL device.

Examples

[0147] Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited by the following examples, and it is of course possible to appropriately modify and implement it within the range that can conform to the gist of the foregoing and following descriptions, and all of them are included in the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

[0148] In the following examples, the structure of the compound was confirmed by mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD6130 type).

[0149] The measurement of the weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin in terms of polystyrene was carried out under the following conditions by the GPC method. Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GEL G2000HXL Column temperature: 40 °C Solvent: Tetrahydrofuran Flow rate: 1.0 mL / min Solid content concentration of the analysis sample: 0.001 - 0.01 mass% Injection volume: 50 μL Detector: RI Standard substance for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio (Mw / Mn) of the weight average molecular weight and number average molecular weight in terms of polystyrene obtained above was defined as the dispersity.

[0150] Synthesis Example 1 8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 10 parts of 7-tridecylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto Chemical Co., Inc.), and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and stirred at 150 °C for 3 hours. While maintaining the obtained mixture at 20 °C or lower, 267 parts of pre-prepared 37% hydrochloric acid (manufactured by Kanto Chemical Co., Inc.) and 1300 parts of water were added, and an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the residue after filtration was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60 °C to obtain 12 parts of the compound represented by the formula (I-2) (Compound (I-2)) (yield 79%).

[0151]

Chemical formula

[0152] <Identification of Compound (I-2)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 755 Exact Mass: 754

[0153] Synthesis Example 2 5.0 parts of the compound (I-2) obtained in Synthesis Example 1, 1.5 parts of potassium hydroxide (manufactured by Kanto Chemical Co., Inc.), and 10 parts of tert-butyl alcohol (manufactured by Kanto Chemical Co., Inc.) were added, and the mixture was stirred at 80 °C for 1 hour. After cooling to 0 °C, while maintaining the obtained mixture at 20 °C or lower, 10 parts of hydrochloric acid (manufactured by Kanto Chemical Co., Inc.) and 48 parts of water, which had been prepared in advance, were added, and a red-violet precipitate was formed. The mixture containing this blue-violet precipitate was filtered, and the residue after filtration was washed with 400 parts of water and 15 parts of ethanol. The obtained residue was dried under reduced pressure at 60 °C and purified by a silica gel column (solvent: chloroform / acetic acid = 50 / 1, vol / vol), whereby 2.3 parts of the compound represented by the formula (I-3) (Compound (I-3)) were obtained (yield 61%).

[0154] [Chemical formula]

[0155] <Identification of Compound (I-3)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 574 Exact Mass: 573

[0156] Synthesis Example 3 5.0 parts of the compound (I-3) obtained in Synthesis Example 2, 20 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.), and 21 parts of 4-dimethylaminopyridine (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 170 °C for 15 hours. After cooling to 90 °C, 520 parts of hydrochloric acid (manufactured by Kanto Chemical Co., Inc.), 2600 parts of water, and 2100 parts of ethanol, which had been prepared in advance, were added to the obtained mixture, and a reddish-purple precipitate was formed. The mixture containing the reddish-purple precipitate was filtered, and the residue after filtration was washed with 400 parts of water and 15 parts of ethanol. The obtained residue was dried under reduced pressure at 60 °C and purified by a silica gel column (solvent: chloroform / ethyl acetate = 2 / 1, vol / vol), whereby 1.0 part of the compound represented by the formula (I-4) (compound (I-4)) was obtained (yield 19%).

[0157] [Chemical formula]

[0158] <Identification of Compound (I-4)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 596 Exact Mass: 595

[0159] Synthesis Example 4 An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, and the atmosphere was replaced with a nitrogen atmosphere. 280 parts of propylene glycol monomethyl ether acetate was placed, and the mixture was heated to 80 °C while stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6A mixed solution of 289 parts of a mixture of decan-9-yl acrylate (the content ratio is 1:1 in molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was maintained at 80 °C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution with a solid content of 35.1% and a viscosity of 125 mPa·s measured with a B-type viscometer (23 °C). The weight average molecular weight Mw of the produced copolymer was 9.2×10 3 , the dispersity was 2.08, and the acid value in terms of solid content was 77 mg-KOH / g. Resin B1 has the following structural units.

[0160] [Chemical formula]

[0161] Example 1 (1) Preparation of Colored Resin Composition 1 The following components were mixed to obtain Colored Resin Composition 1. (A) Colorant: 2.6 parts of the compound represented by formula (I-4) (B) Resin: 54 parts of the resin B1 solution (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate (2) Preparation of Colored Resin Composition 1' Next, the following components were mixed to obtain Colored Resin Composition 1'. 478 parts of Colored Resin Composition 1 (C) Polymerizable compound: Dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 2 parts (F) Levelling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.15 part

[0162] (2) Preparation of Colored Coating Film (Color Filter) On a 5 cm square glass substrate (Eagle XG; manufactured by Corning), a colored resin composition was applied by spin coating so that the film thickness after post-baking would be 2.0 μm, and then pre-baked at 100 °C for 3 minutes to form a colored composition layer. After cooling to room temperature, the colored composition layer formed on the substrate was irradiated with light at an exposure dose of 80 mJ / cm 2 (based on 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). After light irradiation, post-baking was carried out in an oven at 230 °C for 30 minutes to obtain a colored coating film. The film thickness of the colored coating film was measured using DEKTAK3 (manufactured by Nippon Vacuum Technology Co., Ltd.).

[0163] (3) Contrast Evaluation For the obtained colored coating film, the contrast was measured using a contrast meter (CT-1: manufactured by Kambara Electric Co., Ltd., color difference meter BM-5A: manufactured by Topcon Corporation, light source: F-10, polarizing film: manufactured by Kambara Electric Co., Ltd.). The blank value during measurement was 30,000. If the contrast of the colored coating film is good, it can be said that the contrast of the colored pattern made from the same colored resin composition is also good. The results are shown in Table 6.

[0164] Comparative Example 1 The same operations as in Example 1 were carried out except that the compound represented by the formula (I-4) in Example 1 was replaced with the compound represented by the formula (I-2) to prepare a colored resin composition and a colored coating film, and contrast evaluation was performed. The results are shown in Table 6.

[0165]

Table 6

Claims

**Claim 1** A colored resin composition for a color filter, containing a colorant and an alkali-soluble resin, wherein the colorant contains a compound represented by formula (I). 【Chemical 1】 [In formula (I), R 1 ~R 9 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, a hydroxy group, a carboxy group or a nitro group, and the methylene group contained in the hydrocarbon group may be replaced by -O- or -CO-. ring Z represents a group represented by formula (Z-2) or formula (Z-3).] 【Chemical 2】 [* represents a bond.] **Claim 2** The colored resin composition for a color filter according to claim 1, further containing a polymerizable compound and a polymerization initiator. **Claim 3** A color filter formed from the colored resin composition for a color filter according to claim 1 or 2. **Claim 4** A display device including the color filter according to claim 3.

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