Colored resin composition, color filter, and display device

Abstract

The present application provides a colored resin composition, a color filter, and a display device. The colored resin composition is useful in obtaining a color filter having excellent chemical resistance. The colored resin composition includes a colorant and a resin. The colorant includes a compound represented by formula (I). In formula (I), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 each independently represent a hydrogen atom, a hydroxyl group, a nitro group, a cyano group, a halogen atom, a carboxyl group, a sulfo group, a sulfamoyl group, a metallocene group, a hydrocarbon group having 1 to 30 carbon atoms, or the like, R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 are one or more groups having a polar group as a substituent, n represents an integer of 1 to 3, A q‑ represents a q-valent anion, q represents an integer of 1 to 3, and p represents a coefficient for maintaining the charge of the compound represented by formula (I) neutral.

Description

TECHNICAL FIELD

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

[0002] A color filter used in a display device such as a liquid crystal display device, an electroluminescent display device, and a plasma display, or a solid-state imaging element such as a CCD or CMOS sensor is manufactured from a colored curable resin composition. As such a colored curable resin composition, a composition containing a compound represented by formula (A-X) as a colorant is known (Patent Document 1).

[0003] [Chemical Formula 1]

[0004]

[0005] PRIOR ART DOCUMENTS

[0006] PATENT DOCUMENTS

[0007] Patent Document 1: International Publication No. 2014 / 196464 SUMMARY

[0008] PROBLEMS TO BE SOLVED BY THE INVENTION

[0009] The color filter formed from the composition containing the compound represented by formula (A-X) known heretofore is not satisfactory from the viewpoint of chemical reagent resistance.

[0010] Therefore, the present application provides a colored resin composition useful in obtaining a color filter excellent in chemical reagent resistance.

[0011] METHOD FOR SOLVING THE PROBLEMS

[0012] The present application is as follows.

[0013] [1] A colored resin composition comprising a colorant and a resin, the colorant comprising a compound represented by formula (I),

[0014] [Chemical Formula 2]

[0015]

[0016] [In formula (I),

[0017] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R10 each independently represents a hydrogen atom, a hydroxyl group, a nitro group, a cyano group, a halogen atom, a carboxyl group, a sulfo group, a sulfamoyl group, a metallocenyl group, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or two or more methylene groups in the above hydrocarbon group are replaced with a divalent group selected from the following Group I, wherein when two or more methylene groups are replaced with a divalent group selected from the following Group I, the divalent groups are not adjacent,

[0018] The hydrogen atom included in the above hydrocarbon group can be replaced with a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, a sulfo group, a phosphono group, a sulfamoyl group, an isocyanate group, or a heterocycle,

[0019] R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 each independently represents a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or two or more methylene groups in the above hydrocarbon group are replaced with a divalent group selected from the following Group I, wherein when two or more methylene groups are replaced with a divalent group selected from the following Group I, the divalent groups are not adjacent,

[0020] The hydrogen atom included in the above hydrocarbon group can be replaced with a heterocycle or a polar group,

[0021] R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 one or more of which is a group having a polar group as a substituent,

[0022] n represents an integer of 1 to 3,

[0023] A q- represents a q-valent anion,

[0024] q represents an integer of 1 to 3,

[0025] p represents a coefficient that maintains the charge of the compound represented by Formula (I) to be neutral.

[0026] Group I: -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO2-, -SO3-, -NH-, -CONH-, -NHCO-, -SO2NH-, -NHSO2-, or -N=CH-

[0027] [2] The colored resin composition according to [1], further comprising a polymerizable compound and a polymerization initiator.

[0028] [3] The colored resin composition according to [1] or [2], wherein the colorant further comprises a pigment (wherein the compound represented by formula (I) is excluded).

[0029] [4] A color filter formed from the colored resin composition according to [1].

[0030] [5] A display device comprising the color filter according to [4].

[0031] Note that, in the present specification, the compounds exemplified as each component can be used alone or in combination with a plurality of kinds thereof, unless otherwise specified.

[0032] Effects of the Invention

[0033] The colored resin composition according to the present application can provide a color filter having excellent chemical resistance. DETAILED DESCRIPTION

[0034] <Colored resin composition>

[0035] The colored resin composition according to the present application comprises a colorant (hereinafter, can be referred to as "colorant (A)") and a resin (hereinafter, can be referred to as "resin (B)"), and the colorant (A) comprises a compound represented by formula (I) (hereinafter, can be referred to as "compound (I)").

[0036] The colored resin composition according to the present application preferably further comprises a polymerizable compound (hereinafter, can be referred to as "polymerizable compound (C)") and a polymerization initiator (hereinafter, can be referred to as "polymerization initiator (D)").

[0037] The colored resin composition according to the present application can further comprise a polymerization initiation aid (D1), a solvent (E), and a leveling agent (F).

[0038] <Colorant (A)>

[0039] The colored resin composition according to the present application comprises the compound (I) as the colorant (A).

[0040] <Compound (I)>

[0041] Hereinafter, the present application will be described using formula (I), but the compound (I) includes a conjugated structure of formula (I), and also includes a compound obtained by rotating each group in formula (I) or a conjugated structure thereof toward the carbon-carbon single bond or the bonding bond of the carbon-carbon single bond.

[0042] [Chemical formula 3]

[0043]

[0044] [In formula (I),

[0045] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 each independently represent a hydrogen atom, a hydroxyl group, a nitro group, a cyano group, a halogen atom, a carboxyl group, a sulfo group, a sulfamoyl group, a metallocene group, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or two or more methylenes in the above hydrocarbon group are substituted with a divalent group selected from the following Group I, wherein when two or more methylenes are substituted with a divalent group selected from the following Group I, the divalent groups are not adjacent,

[0046] The hydrogen atom included in the above hydrocarbon group can be substituted with a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, a sulfo group, a phosphono group, a sulfamoyl group, an isocyanate group, or a heterocycle,

[0047] R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or two or more methylenes in the above hydrocarbon group are substituted with a divalent group selected from the following Group I, wherein when two or more methylenes are substituted with a divalent group selected from the following Group I, the divalent groups are not adjacent,

[0048] The hydrogen atom included in the above hydrocarbon group can be substituted with a heterocycle or a polar group,

[0049] R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 one or more of which is a group having a polar group as a substituent,

[0050] n represents an integer of 1 to 3,

[0051] A q- represents a q-valent anion,

[0052] q represents an integer of 1 to 3,

[0053] p represents a coefficient that maintains the charge of the compound represented by formula (I) to be neutral.

[0054] Group I: -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO2-, -SO3-, -NH-, -CONH-, -NHCO-, -SO2NH-, -NHSO2-, or -N=CH-

[0055] R1is a hydrocarbon group having 1 to 30 carbon atoms, and R2is a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms. 1 R1is a hydrocarbon group having 1 to 30 carbon atoms, and R2is a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms. 16 R1is a hydrocarbon group having 1 to 30 carbon atoms, and R2is a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

[0056] The aliphatic hydrocarbon group having 1 to 30 carbon atoms can be either of saturated and unsaturated, and can be either of straight-chain, branched-chain, and cyclic.

[0057] As the straight-chain or branched-chain aliphatic hydrocarbon group having 1 to 30 carbon atoms, there can be mentioned straight-chain aliphatic hydrocarbon groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, ethenyl group, 1-propenyl group, 2-propenyl (allyl) group, and branched-chain aliphatic hydrocarbon groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, 2-ethylhexyl group, and the like. The number of carbon atoms of the straight-chain or branched-chain aliphatic hydrocarbon group is preferably 1 to 15, more preferably 1 to 10, and further preferably 1 to 8.

[0058] The cyclic aliphatic hydrocarbon group can be either of monocyclic and polycyclic. As the cyclic aliphatic hydrocarbon group, there can be mentioned cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and the like. The number of carbon atoms of the cyclic aliphatic hydrocarbon group is preferably 3 to 18, more preferably 3 to 15, and further preferably 4 to 15.

[0059] As the aromatic hydrocarbon group having 6 to 30 carbon atoms, there can be mentioned phenyl group, naphthyl group, phenanthryl group, anthryl group, and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 18, and further preferably 6 to 15.

[0060] The hydrocarbon group having 1 to 30 carbon atoms can be a group formed by combining two or more of the above-mentioned aliphatic hydrocarbon groups and aromatic hydrocarbon groups, provided that the upper limit of the number of carbon atoms is 30 or less. As such a group, there can be mentioned, for example, xylyl group, trimethylphenyl group, dipropylphenyl group, di(2,2-dimethylpropyl)phenyl group, benzyl group, phenetyl group, 4-phenylbutyl group, and the like. The number of carbon atoms of the group formed by combining two or more of the aliphatic hydrocarbon groups and aromatic hydrocarbon groups is preferably 7 to 25, more preferably 8 to 20, and further preferably 8 to 15.

[0061] R1is a hydrocarbon group having 1 to 30 carbon atoms, and R2is a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms. 1 R1is a hydrocarbon group having 1 to 30 carbon atoms, and R2is a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms. 16 R1is a hydrocarbon group having 1 to 30 carbon atoms, and R2is a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

[0062] Group I: -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO2-, -SO3-, -NH-, -CONH-, -NHCO-, -SO2NH-, -NHSO2-, or -N=CH-

[0063] As a group in which one methylene group in a hydrocarbon group is replaced with -O-, for example, the following groups (* indicates the bonding position) can be given.

[0064] [Chemical Formula 4]

[0065]

[0066] As a group in which one methylene group in a hydrocarbon group is replaced with -S-, for example, the following groups (* indicates the bonding position) can be given.

[0067] [Chemical Formula 5]

[0068]

[0069] As a group in which one methylene group in a hydrocarbon group is replaced with -CO-, for example, the following groups (* indicates the bonding position) can be given.

[0070] [Chemical Formula 6]

[0071]

[0072] As a group in which one methylene group in a hydrocarbon group is replaced with -COO-, for example, the following groups (* indicates the bonding position) can be given.

[0073] [Chemical Formula 7]

[0074]

[0075] As a group in which one methylene group in a hydrocarbon group is replaced with -OCO-, for example, the following groups (* indicates the bonding position) can be given.

[0076] [Chemical Formula 8]

[0077]

[0078] As a group in which one methylene group in a hydrocarbon group is replaced with -COS-, for example, the following groups (* indicates the bonding position) can be given.

[0079] [Chemical Formula 9]

[0080]

[0081] As a group in which one methylene group in a hydrocarbon group is replaced by -OCS-, for example, the following groups (* indicates the bonding position) can be given.

[0082] [Chemical Formula 10]

[0083]

[0084] As a group in which one methylene group in a hydrocarbon group is replaced by -SO2-, for example, the following groups (* indicates the bonding position) can be given.

[0085] [Chemical Formula 11]

[0086]

[0087] As a group in which one methylene group in a hydrocarbon group is replaced by -SO3-, for example, the following groups (* indicates the bonding position) can be given.

[0088] [Chemical Formula 12]

[0089]

[0090] As a group in which one methylene group in a hydrocarbon group is replaced by -NH-, for example, the following groups (* indicates the bonding position) can be given.

[0091] [Chemical Formula 13]

[0092]

[0093] As a group in which one methylene group in a hydrocarbon group is replaced by -CONH-, for example, the following groups (* indicates the bonding position) can be given.

[0094] [Chemical Formula 14]

[0095]

[0096] As a group in which one methylene group in a hydrocarbon group is replaced by -NHCO-, for example, the following groups (* indicates the bonding position) can be given.

[0097] [Chemical Formula 15]

[0098]

[0099] As a group in which one methylene group in a hydrocarbon group is replaced by -SO2NH-, for example, the following groups (* indicates the bonding position) can be given.

[0100] [Chemical Formula 16]

[0101]

[0102] As a group in which one methylene group in a hydrocarbon group is replaced with -NHSO2-, for example, the following groups (* indicates the bonding position) can be given.

[0103] [Chemical Formula 17]

[0104]

[0105] As a group in which one methylene group in a hydrocarbon group is replaced with -N=CH-, for example, the following groups (* indicates the bonding position) can be given.

[0106] [Chemical Formula 18]

[0107]

[0108] As R 1 ~R 16 A group in which two or more methylene groups in a hydrocarbon group represented by the above formula are replaced with a divalent group selected from the above Group I can be a group in which one methylene group in the above hydrocarbon group is replaced with a divalent group selected from Group I, appropriately combined groups in which one methylene group in the above hydrocarbon group is replaced with a divalent group selected from Group I, or the like, provided that the divalent groups are not adjacent.

[0109] As R 11 ~R 16 A group in which one or two or more methylene groups in a hydrocarbon group represented by the above formula are replaced with a divalent group selected from the above Group I is preferably not a polar group.

[0110] As R 1 ~R 10 The halogen atom represented by the above formula can be a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or the like, and is preferably a chlorine atom.

[0111] As R 1 ~R 10 The metallocene group represented by the above formula can be a ferrocenyl group, a nickelocene group, a cobaltocene group, a ferrocenylalkyl group, a ferrocenylalkoxy group, or the like.

[0112] As the halogen atom that can substitute a hydrogen atom included in a hydrocarbon group represented by the above formula R 1 ~R 10 The halogen atom that can substitute a hydrogen atom included in a hydrocarbon group represented by the above formula R 1 ~R 10 is the same as the halogen atom represented by the above formula R

[0113] The halogen atom that can substitute a hydrogen atom included in a hydrocarbon group represented by the above formula R 1 ~R 16The number of carbon atoms in the heterocycle containing hydrogen atoms in the represented hydrocarbon group is preferably 1 to 20. Examples of such heterocycles include those containing at least one atom selected from nitrogen, oxygen, and sulfur atoms; specific examples include nitrogen-containing heterocyclic butanes, pyrroles, and benzo[a]benzene. Azole, thiazole, oxetane, furan, thiohepane, thiophene, etc.

[0114] As R 1 ~R 10 Preferably, it is a hydrogen atom or a halogen atom, more preferably R. 1 ~R 10 One to six atoms are halogen atoms, and the rest are hydrogen atoms. Further preference is given to R. 1 ~R 10 One to four atoms are halogen atoms, and the rest are hydrogen atoms. R is further preferred. 1 ~R 10 Two of them are halogen atoms, and the rest are hydrogen atoms.

[0115] In R 1 ~R 10 When two of the atoms are halogen atoms, these two halogen atoms are preferably R. 7 ~R 10 Any two of them, R is preferred. 7 and R 9 It is a halogen atom.

[0116] So-called can replace R 11 ~R 16 The polar group containing hydrogen atoms in the hydrocarbon group refers to a functional group containing at least one heteroatom other than a carbon atom and a hydrogen atom. Examples of heteroatoms include oxygen atoms, sulfur atoms, phosphorus atoms, nitrogen atoms, and halogen atoms. Specific examples of the aforementioned polar groups include hydroxyl groups, carboxyl groups, epoxy groups, amide groups (including amide groups such as N-methylamide, N-isopropylamide, N-cyclopropylamide, and N-phenylamide, which are N-substituted by hydrocarbon groups having 1 to 12 carbon atoms), nitrile groups, amino groups, imide groups, isocyanate groups, thiols, alkoxy groups, sulfonyl groups, phosphonyl groups, nitro groups, alkoxycarbonyl groups, acetyl groups, and halogen atoms, preferably acid groups such as carboxyl groups, amide groups, sulfonyl groups, and phosphonyl groups, more preferably carboxyl or amide groups, and even more preferably carboxyl groups.

[0117] A group that has a polar substituent, in which the hydrogen atom contained in the hydrocarbon group is replaced by a polar group, includes, for example, groups represented by formulas (po-1) to (po-6) with a carboxyl group as the polar group, and groups represented by formulas (po-7) to (po-10) with an amide group as the polar group. In the formulas, * indicates the bonding position.

[0118] [Chemical Formula 19]

[0119]

[0120] R 11 ~R 16 At least one of them is R 11 ~R 16 The group represented is a hydrocarbon group in which hydrogen atoms are replaced by polar groups, thus possessing polar substituents. As long as R... 11 ~R 16 If at least one of the components has a polar group as a substituent, a color filter with excellent resistance to chemical reagents can be formed.

[0121] As R 11 ~R 16 Preferably, the hydrocarbon group has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably an aliphatic hydrocarbon group, and even more preferably a saturated linear aliphatic hydrocarbon group. The saturated linear aliphatic hydrocarbon group preferably has 1 to 15 carbon atoms, more preferably 1 to 10, and even more preferably 1 to 5. Furthermore, in R... 11 ~R 16 In the case of a group having a polar group as a substituent, as R 11 ~R 16 Preferably, it is an aliphatic hydrocarbon group or a group consisting of two or more aliphatic and aromatic hydrocarbon groups, in R 11 ~R 16 In the case where there is no polar group as a substituent, as R 11 ~R 16 Preferably, it is an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

[0122] In addition, R is preferred 11 ~R 16 One to four of them are groups with polar substituents, more preferably R. 11 ~R 16 Two to four of the groups are substituents with polar groups, with R being more preferred. 11 ~R 16 Two of them are groups with polar substituents.

[0123] The value of n is preferably 1 to 2, and more preferably 1.

[0124] A q- The anions represented by q are anions with valences of 1 to 3, and can be inorganic or organic anions.

[0125] Examples of such inorganic anions include hydroxide ions, halide ions (fluoride ions, chloride ions, bromide ions, iodide ions, etc.), nitrate ions, perchlorate ions, hydrochloric acid ions, sulfate ions, thiocyanate ions, phosphate ions, phosphotungstic acid ions, phosphotungstic acid ions, phosphotungstic acid ions, hexafluorophosphate ions, molybdate ions, tungstate ions, titanate ions, zirconate ions, borate ions, tetrafluoroborate ions, etc.

[0126] Examples of such organic anions include, for example, acetate ions, trifluoroacetic acid ions, benzoic acid ions, palmitic acid ions, tartaric acid ions, ferric ethylenediaminetetraacetate ions, and other organic carboxylic acid anions; methanesulfonate ions, dodecyl sulfonate ions, vinyl sulfonate ions, benzenesulfonate ions, trifluoromethanesulfonate ions, nonafluorobutanesulfonate ions, 3-(trihydroxysilyl)-1-propanesulfonate ions, toluenesulfonate ions, chlorobenzenesulfonate ions, pentafluorobenzenesulfonate ions, 3-carboxyphenylsulfonic acid, 3-nitrophenylsulfonate ions, benzenedisulfonate ions, diphenylamine-4-sulfonate ions, and 2... -Amino-4-methyl-5-chlorobenzenesulfonic acid ion, 2-amino-5-nitrobenzenesulfonic acid ion, phthalocyanine sulfonic acid ion, perfluoro-4-ethylcyclohexanesulfonic acid ion, naphthalene monosulfonic acid ion, naphthalene disulfonic acid ion, naphthalene trisulfonic acid ion, naphthylamine monosulfonic acid ion, naphthylamine disulfonic acid ion, naphthylamine trisulfonic acid ion, 8-{[3-(trimethoxysilyl)propyl]amino}naphthalene-1-sulfonic acid ion, 8-{[3-(trimethoxysilyl)propyl]amino}naphthalene-1,5-disulfonic acid ion, isoquinoline-5-sulfonic acid ion, naphthol monosulfonic acid ion, naphthol disulfonic acid ion, naphthol trisulfonic acid Organic sulfonic acid anions such as acid ions, N,N-bis(2-hydroxyethyl)-2-aminoethane sulfonate ions; organic phosphoric acid anions such as octyl phosphate ions, dodecyl phosphate ions, octadecyl phosphate ions, phenyl phosphate ions, nonylphenyl phosphate ions, 2,2'-methylenebis(4,6-di-tert-butylphenyl)phosphonate ions, 3-(trihydroxysilyl)propylmethylphosphonate ions; organic sulfuric acid anions such as lauryl sulfate ions, lauryl ether sulfate ions, polyoxyethylene alkylphenol sulfonate ions; and organic boric acid anions such as tetraarylboronic acid ions and butyltriphenylboronic acid ions. Anions include: tricyanomethyl ions, tris(trifluoromethanesulfonyl)methyl ions, tris(perfluoroethylsulfonyl)methyl ions, and other methyl ions; dicyanamide ions; trifluoromethanesulfonamide ions, benzenesulfonamide ions, and other sulfonamide ions; N,N-bis(fluorosulfonyl)imide ions, bis(trifluoromethanesulfonyl)imide ions, bis(nonafluorobutanesulfonyl)imide ions, N,N-hexafluoro-1,3-disulfonylimide ions, 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonylimide ions, and other sulfonylimide ions; etc.

[0127] As A q-The anion represented by the q-valence is preferably hexafluorophosphate ion, tungstate ion, monovalent organic carboxylic acid anion, monovalent or divalent organic sulfonic acid anion, monovalent organic phosphoric acid anion, monovalent organic boric acid anion, monovalent methyl ion, dicyandiamide ion, monovalent sulfonamide ion, and monovalent sulfonamide ion; more preferably tungstate ion, monovalent organic carboxylic acid anion, monovalent or divalent organic sulfonic acid anion, monovalent organic phosphoric acid anion, monovalent methyl ion, dicyandiamide ion, and monovalent sulfonamide ion; and even more preferably tungstate ion, monovalent organic carboxylic acid anion, monovalent or divalent organic sulfonic ... The ions are valent organic sulfonic acid anions, monovalent organic phosphoric acid anions, monovalent methyl ions, and monovalent sulfonamide ions, more preferably tungstate ions, monovalent organic carboxylic acid anions, monovalent or divalent organic sulfonic acid anions, monovalent organic phosphoric acid anions, and monovalent sulfonamide ions, more preferably tungstate ions, monovalent organic carboxylic acid anions, monovalent or divalent organic sulfonic acid anions, and monovalent sulfonamide ions, more preferably monovalent organic sulfonic acid anions and monovalent sulfonamide ions, and particularly preferably 3-carboxyphenylsulfonic acid and bis(trifluoromethylsulfonyl)imide ions.

[0128] Examples of compounds (I) include those represented by formulas (I-1) to (I-146) shown in Tables 1 to 4.

[0129] Compound (I) is preferably a compound represented by formula (I-25) to (I-48), formula (I-73), formula (I-74), formula (I-77) to (I-80), formula (I-87), formula (I-88), formula (I-109) to (I-127).

[0130] [Table 1]

[0131] [R 1 ~R 6 ,R 8 ,R 10 ]]> [R 7 、R 9 ]]> [R 11 、R 13 ]]> [R 12 、R 14 ]]> [R 15 、R 16 ]]> n A q- ]]> p (I-1) H Cl po-2 Et Et 1 an-1 1 (I-2) H Cl po-2 Et Et 1 an-2 1 (I-3) H Cl po-2 Et Pr 1 an-1 1 (I-4) H Cl po-2 Et Pr 1 an-2 1 (I-5) H Cl po-2 Pr Et 1 an-1 1 (I-6) H Cl po-2 Pr Et 1 an-2 1 (I-7) H Cl po-2 Pr Pr 1 an-1 1 (I-8) H Cl po-2 Pr Pr 1 an-2 1 (I-9) H Cl Et po-2 Et 1 an-1 1 (I-10) H Cl Et po-2 Et 1 an-2 1 (I-11) H Cl Et po-2 Pr 1 an-1 1 (I-12) H Cl Et po-2 Pr 1 an-2 1 (I-13) H Cl Pr po-2 Et 1 an-1 1 (I-14) H Cl Pr po-2 Et 1 an-2 1 (I-15) H Cl Pr po-2 Pr 1 an-1 1 (I-16) H Cl Pr po-2 Pr 1 an-2 1 (I-17) H Cl Et Et po-2 1 an-1 1 (I-18) H Cl Et Et po-2 1 an-2 1 (I-19) H Cl Et Pr po-2 1 an-1 1 (I-20) H Cl Et Pr po-2 1 an-2 1 (I-21) H Cl Pr Et po-2 1 an-1 1 (I-22) H Cl Pr Et po-2 1 an-2 1 (I-23) H Cl Pr Pr po-3 1 Et 1 (I-24) H Cl Pr Pr Et 1 an-1 1 (I-25) H Cl po-3 Et Et 1 an-2 1 (I-26) H Cl po-3 Et an-1 1 po-3 1 (I-27) H Cl Et an-2 Pr 1 po-3 1 (I-28) H Cl Et an-1 Pr 1 po-3 1 (I-29) H Cl Et Pr an-2 1 po-3 1 (I-30) H Cl an-1 Pr po-3 1 an-2 1 (I-31) H Cl Et Pr Pr 1 po-3 1 (I-32) H Cl Et Pr Pr 1 an-1 1 (I-33) H Cl Et po-3 Et 1 an-2 1 (I-34) H Cl Et po-3 an-1 1 Et 1 (I-35) H Cl po-3 an-2 Pr 1 po-3 1 (I-36) H Cl Et an-1 Pr 1 po-3 1

[0132] [Table 2]

[0133] [R 1 ~R 6 ,R 8 ,R 10 ]]> [R 7 、R 9 ]]> [R 11 、R 13 ]]> [R 12 、R 14 ]]> [R 15 、R 16 ]]> n A q- ]]> p (I-37) H Cl Pr Et an-2 1 po-3 1 (I-38) H Cl Pr an-1 po-3 1 an-2 1 (I-39) H Cl Pr Et Pr 1 Et 1 (I-40) H Cl Pr po-3 Pr 1 an-1 1 (I-41) H Cl Et Et po-3 1 an-2 1 (I-42) H Cl Et po-3 an-1 1 Et 1 (I-43) H Cl po-3 Pr an-2 1 Et 1 (I-44) H Cl po-3 Pr an-1 1 Et 1 (I-45) H Cl Pr po-3 an-2 1 po-3 1 (I-46) H Cl Pr an-1 po-3 1 an-2 1 (I-47) H Cl Pr Pr po-4 1 Et 1 (I-48) H Cl Pr Pr Et 1 an-1 1 (I-49) H Cl po-4 Et Et 1 an-2 1 (I-50) H Cl po-4 Et an-1 1 po-4 1 (I-51) H Cl Et an-2 Pr 1 po-4 1 (I-52) H Cl Et an-1 Pr 1 po-4 1 (I-53) H Cl Et Pr an-2 1 po-4 1 (I-54) H Cl an-1 Pr po-4 1 an-2 1 (I-55) H Cl Et Pr Pr 1 po-4 1 (I-56) H Cl Et Pr Pr 1 an-1 1 (I-57) H Cl Et po-4 Et 1 an-2 1 (I-58) H Cl Et po-4 an-1 1 Et 1 (I-59) H Cl po-4 an-2 Pr 1 po-4 1 (I-60) H Cl Et an-1 Pr 1 po-4 1 (I-61) H Cl Pr Et an-2 1 po-4 1 (I-62) H Cl Pr an-1 po-4 1 an-2 1 (I-63) H Cl Pr Et Pr 1 Et 1 (I-64) H Cl Pr po-4 Pr 1 an-1 1 (I-65) H Cl Et Et po-4 1 an-2 1 (I-66) H Cl Et po-4 an-1 1 Et 1 (I-67) H Cl po-4 Pr an-2 1 Et 1 (I-68) H Cl po-4 Pr an-1 1 Et 1 (I-69) H Cl Pr po-4 an-2 1 po-4 1 (I-70) H Cl Pr an-1 po-4 1 an-2 1 (I-71) H Cl Pr Pr Et 1 Et 1 (I-72) H Cl Pr Pr po-6 1 po-6 1

[0134] [Table 3]

[0135] [R 1 ~R 6 ,R 8 ,R 10 ]]> [R 7 、R 9 ]]> [R 11 、R 13 ]]> [R 12 、R 14 ]]> [R 15 ]]> [R 16 ]] n A q- ]]> p (I-73) H Cl an-1 Et Et po-6 1 po-6 1 (I-74) H Cl an-2 Et Et po-7 1 po-7 1 (I-75) H Cl an-1 Et Et po-7 1 po-7 1 (I-76) H Cl an-2 Et Et po-9 1 po-9 1 (I-77) H Cl an-1 Et Et po-9 1 po-9 1 (I-78) H Cl an-2 Et Ph po-3 1 po-3 1 (I-79) H Cl an-1 Et Ph po-3 1 po-3 1 (I-80) H Cl an-2 Et Ph po-6 1 po-6 1 (I-81) H Cl an-1 Et Ph po-6 1 po-6 1 (I-82) H Cl an-2 Et Ph po-7 1 po-7 1 (I-83) H Cl an-1 Et Ph po-7 1 po-7 1 (I-84) H Cl an-2 Et Ph po-9 1 po-9 1 (I-85) H Cl an-1 Et Ph po-9 1 po-9 1 (I-86) H Cl an-2 Et Et Et 1 po-3 1 (I-87) H Cl an-1 Et Et Et 1 po-3 1 (I-88) H Cl an-2 Et Et Et 1 po-6 1 (I-89) H Cl an-1 Et Et Et 1 po-6 1 (I-90) H Cl an-2 ​ ​ ​ 1 ​ 1 (I-91) H Cl Et Et Et po-7 1 an-1 1 (I-92) H Cl Et Et Et po-7 1 an-2 1 (I-93) H Cl Et Et Et po-9 1 an-1 1 (I-94) H Cl Et Et Et po-9 1 an-2 1 (I-95) H Cl Et Ph Et po-3 1 an-1 1 (I-96) H Cl Et Ph Et po-3 1 an-2 1 (I-97) H Cl Et Ph Et po-6 1 an-1 1 (I-98) H Cl Et Ph Et po-6 1 an-2 1 (I-99) H Cl Et Ph Et po-7 1 an-1 1 (I-100) H Cl Et Ph Et po-7 1 an-2 1 (I-101) H Cl Et Ph Et po-9 1 an-1 1 (I-102) H Cl Et Ph Et po-9 1 an-2 1 (I-103) H Cl po-6 Et Et Et 1 an-1 1 (I-104) H Cl po-6 Et Et Et 1 an-2 1 (I-105) H Cl po-7 Et Et Et 1 an-1 1 (I-106) H Cl po-7 Et Et Et 1 an-2 1 (I-107) H Cl po-9 Et Et Et 1 an-1 1 (I-108) H Cl po-9 Et Et Et 1 an-2 1

[0136] [Table 4]

[0137] [R 1 ~R 6 ,R 8 ,R 10 ]]> [R 7 、R 9 ]]> [R 11 、R 13 ]]> [R 12 、R 14 ]]> [R 15 、R 16 ]]> n A q- ]]> p (I-109) H Cl Et Et po-3 1 an-3 1 (I-110) H Cl Et Et po-3 1 an-4 1 (I-111) H Cl Et Et po-3 1 an-5 1 (I-112) H Cl Et Et po-3 1 an-6 1 (I-113) H Cl Et Et po-3 1 an-7 1 (I-114) H Cl Et Et po-3 1 an-8 1 (I-115) H Cl Et Et po-3 1 an-9 1 (I-116) H Cl Et Et po-3 1 an-10 1 (I-117) H Cl Et Et po-3 1 an-11 1 (I-118) H Cl Et Et po-3 1 an-12 1 (I-119) H Cl Et Et po-3 1 an-13 1 (I-120) H Cl Et Et po-3 1 an-14 1 (I-121) H Cl Et Et po-3 1 an-15 1 (I-122) H Cl Et Et po-3 1 an-16 1 (I-123) H Cl Et Et po-3 1 an-17 1 (I-124) H Cl Et Et po-3 2 an-18 1 (I-125) H Cl Et Et po-3 2 an-19 1 (I-126) H Cl Et Et po-3 1 an-20 1 (I-127) H Cl Et Et po-3 1 an-21 1 (I-128) H Cl po-3 Et Et 1 an-3 1 (I-129) H Cl po-3 Et Et 1 an-4 1 (I-130) H Cl po-3 Et Et 1 an-5 1 (I-131) H Cl po-3 Et Et 1 an-6 1 (I-132) H Cl po-3 Et Et 1 an-7 1 (I-133) H Cl po-3 Et Et 1 an-8 1 (I-134) H Cl po-3 Et Et 1 an-9 1 (I-135) H Cl po-3 Et Et 1 an-10 1 (I-136) H Cl po-3 Et Et 1 an-11 1 (I-137) H Cl po-3 Et Et 1 an-12 1 (I-138) H Cl po-3 Et Et 1 an-13 1 (I-139) H Cl po-3 Et Et 1 an-14 1 (I-140) H Cl po-3 Et Et 1 an-15 1 (I-141) H Cl po-3 Et Et 1 an-16 1 (I-142) H Cl po-3 Et Et 1 an-17 1 (I-143) H Cl po-3 Et Et 2 an-18 1 (I-144) H Cl po-3 Et Et 2 an-19 1 (I-145) H Cl po-3 Et Et 1 an-20 1 (I-146) H Cl po-3 Et Et 1 an-21 1

[0138] In Tables 1-4, Et represents ethyl, Pr represents propyl, Ph represents phenyl, po-2 to po-4, po-6, po-7 and po-9 each mean the group represented by the above formulas (po-2) to (po-4), (po-6), (po-7) and (po-9), and an-1 to an-21 respectively represent the group represented by the following formulas (an-1) to (an-21).

[0139] [Chemical Formula 20]

[0140]

[0141] There are no particular limitations on the synthesis method of compound (I), and the method described in International Publication No. 2014 / 196464 can be used as a reference for synthesis.

[0142] The content of compound (I) relative to 100 parts by weight of resin (B) is preferably 0.05 to 100 parts by weight, more preferably 0.1 to 80 parts by weight, even more preferably 0.5 to 50 parts by weight, and even more preferably 0.5 to 30 parts by weight.

[0143] The content of compound (I) is preferably 1% by mass or more, and more preferably 5% by mass or more, in the total amount of colorant (A).

[0144] The colorant (A) may contain a colorant different from compound (I) in addition to compound (I), which may be either a dye (hereinafter referred to as dye (A1)) or a pigment (hereinafter referred to as pigment (A2)). The colorant different from compound (I) may also contain one or both of dye (A1) and pigment (A2).

[0145] The dye (A1) is not particularly limited as long as it does not contain compound (I), and known dyes can be used, such as solvent dyes, acid dyes, direct dyes, mordant dyes, etc. Examples of dyes include, for example, compounds that are colored other than pigments as classified in the Color Index (published by The Society of Dyers and Colourists), or known dyes recorded in the Dyeing Handbook (Shiki-densha). Furthermore, based on their chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthocyanine dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, azomethyl alkali dyes, squaric acid cyanine dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Among these, organic solvent-soluble dyes are preferred.

[0146] Pigment (A2) is not particularly limited and well-known pigments can be used, for example, pigments classified as pigments in the Excellence Index (published by The Society of Dyers and Colourists).

[0147] As pigments, examples include: CI pigment yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, etc.

[0148] CI pigments include orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and other orange pigments;

[0149] CI pigments include red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 269, 291, and other red pigments;

[0150] CI pigment blue 15, 15:3, 15:4, 15:6, 60 and other blue pigments;

[0151] CI pigments include purple 1, 19, 23, 29, 32, 36, 38, and other purple pigments;

[0152] CI pigments include green 7, 36, and 58, among other green pigments.

[0153] CI pigments, such as brown 23 and 25;

[0154] CI pigments, black 1, 7, and other black pigments, etc.

[0155] As pigments (A2), the preferred pigments are yellow pigments such as CI pigment yellow 185; red pigments such as CI pigment red 177, 202, 264, 269, 291; and blue pigments such as CI pigment blue 15:6.

[0156] The pigment is preferably a pigment with uniform particle size. By adding a pigment dispersant, a pigment dispersion in which the pigment is uniformly dispersed in the solution can be obtained.

[0157] Examples of pigment dispersants include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants.

[0158] When using a pigment dispersant, its amount relative to the total amount of pigment (A2) is preferably 1% by mass or more and 100% by mass or less, more preferably 5% by mass or more and 50% by mass or less. If the amount of pigment dispersant used is within the above range, there is a tendency to obtain a pigment dispersion in a uniformly dispersed state.

[0159] The content of colorant (A) relative to the total solids content of the coloring resin composition is preferably 0.5 to 60% by mass, more preferably 1 to 50% by mass, and even more preferably 3 to 45% by mass. Here, the term "total solids content" in this specification refers to the amount excluding the solvent content from the total amount of the coloring resin composition. The total solids content and the content of each component thererelative to it can be determined, for example, by known analytical methods such as liquid chromatography or gas chromatography.

[0160] <Resin (B)>

[0161] Resin (B) is not particularly limited, but is preferably an alkali-soluble resin, more preferably a resin having at least one (a) (hereinafter referred to as "(a)") structural unit derived from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides. Resin (B) is further preferably having at least one structural unit selected from the group consisting of: structural units derived from monomers (b) (hereinafter referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and vinyl unsaturated bonds; structural units derived from monomers (c) (which are different from (a) and (b)) capable of copolymerizing with (a) (hereinafter referred to as "(c)"); and structural units with vinyl unsaturated bonds on their side chains.

[0162] As for (a), examples include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, mono[2-(meth)acryloyloxyethyl] succinate, etc., with acrylic acid, methacrylic acid, and maleic anhydride being preferred.

[0163] (b) Preferably, it is a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an ethylene oxide ring, an oxobutane ring and a tetrahydrofuran ring) and a (meth)acryloyloxy group.

[0164] It should be noted that in this specification, the term "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0165] As an example of (b), glycidyl (meth)acrylate, vinyl benzyl glycidyl ether, and 3,4-epoxy tricyclic [5.2.1.0] can be cited. 2,6 Decyl (meth)acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxetane, tetrahydrofurfuryl (meth)acrylate, etc., preferably glycidyl (meth)acrylate, 3,4-epoxytricyclo[5.2.1.0] 2 ,6 Decyl (meth)acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxetane.

[0166] As for (c), examples include methyl methacrylate, butyl methacrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, and tricyclo[5.2.1.0]. 2,6 ] Decane-8-yl (meth)acrylate, tricyclic [5.2.1.0 2,6 [Decan-9-yl(meth)acrylate, benzyl(meth)acrylate, 2-hydroxyethyl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene, etc., preferably styrene, vinyltoluene, 2-hydroxyethyl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, tricyclic [5.2.1.0] 2,6 ] Decane-8-yl (meth)acrylate, tricyclic [5.2.1.0 2,6 Decane-9-yl(meth)acrylate, etc.

[0167] A resin having structural units with ethylene-unsaturated side chains can be manufactured by adding (b) to a copolymer of (a) and (c), or by adding (a) to a copolymer of (b) and (c). The resin can also be a resin obtained by adding (a) to a copolymer of (b) and (c) and further reacting it with a carboxylic anhydride.

[0168] The polystyrene-converted weight-average molecular weight of resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000.

[0169] The dispersion of resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1 to 6, more preferably 1.2 to 4.

[0170] The acid value of resin (B), converted from solid content, is preferably 20 to 170 mg-KOH / g, more preferably 30 to 150 mg-KOH / g, and even more preferably 40 to 135 mg-KOH / g. Here, the acid value is a value determined as the amount (mg) of potassium hydroxide required to neutralize 1g of resin (B), and can be obtained, for example, by titration using an aqueous solution of potassium hydroxide.

[0171] The content of resin (B) relative to the total amount of solid components in the coloring resin composition is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, and even more preferably 25 to 70% by mass.

[0172] <Polymerizing Compounds (C)>

[0173] The polymerizable compound (C) is a compound that can be polymerized by means of an active free radical and / or acid generated by a polymerization initiator (D). Examples include compounds with polymerizable vinyl unsaturated bonds, and (meth)acrylate compounds are preferred.

[0174] The polymerizable compound (C) is preferably a polymerizable compound having three or more vinyl unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate.

[0175] The weight-average molecular weight of the polymeric compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.

[0176] When the polymeric compound (C) is included, the content of the polymeric compound (C) relative to the total amount of solid components in the coloring resin composition is preferably 5 to 60% by mass, more preferably 10 to 50% by mass, and even more preferably 15 to 40% by mass.

[0177] <Polymerization Initiator (D)>

[0178] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active free radicals, acids, etc., through the action of light or heat, thereby initiating polymerization; known polymerization initiators can be used. Examples of polymerization initiators that generate active free radicals include, for instance, N-benzoyloxy-1-(4-phenylsulfonylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfonylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfonylphenyl)-3-cyclopentylpropane-1-one-2-imine, and N-acetoxy-1-(4-phenylsulfonylphenyl)-3-cyclohexylpropane-1-one-2-imine. 2-keto-2-imine, 2-methyl-2-morpholino-1-(4-methylsulfonylphenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, 1-hydroxycyclohexylphenyl ketone, 2,4-bis(trichloromethyl)-6-piperyl-1,3,5-triazine, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbimidazole, etc.

[0179] The polymerization initiator is preferably a polymerization initiator comprising at least one selected from the group consisting of triazine compounds, acylphosphine oxide compounds, alkylphenone compounds, oxime compounds and bimidazole compounds, and more preferably a polymerization initiator comprising an oxime compound.

[0180] When a polymerization initiator (D) is included, the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C). If the content of the polymerization initiator (D) is within the above range, there is a tendency to increase sensitivity and shorten the exposure time, thereby improving the productivity of the color filter.

[0181] <Polymerization Initiator (D1)>

[0182] A polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of polymerizable compounds initiated by a polymerization initiator. In cases where a polymerization initiator (D1) is included, it is usually used in combination with a polymerization initiator (D).

[0183] Examples of polymerization initiators (D1) include 4,4'-bis(dimethylamino)benzophenone (commonly known as milchone), 4,4'-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, and N-phenylglycine.

[0184] When using such a polymerization initiator (D1), its content is preferably 0.1 to 30 parts by mass relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C), more preferably 1 to 20 parts by mass. If the amount of polymerization initiator (D1) is within the above range, it tends to be able to form colored patterns with higher sensitivity and improve the productivity of the color filter.

[0185] Solvent (E)

[0186] The solvent (E) is not particularly limited and may be any solvent commonly used in the art. Examples include ester solvents (solvents containing -COO- but not -O-), ether solvents (solvents containing -O- but not -COO-), ether ester solvents (solvents containing both -COO- and -O-), ketone solvents (solvents containing -CO- but not -COO-), alcohol solvents (solvents containing OH but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc.

[0187] Examples of solvents include:

[0188] Ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone (solvents containing -COO- but not -O- in the molecule);

[0189] Ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, and diethylene glycol methyl ethyl ether (solvents containing -O- but not -COO- in the molecule);

[0190] 3-Methoxypropionate methyl ester, 3-ethoxypropionate ethyl ester, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate and other ether ester solvents (solvents containing -COO- and -O- in the molecule);

[0191] Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), heptanone, 4-methyl-2-pentanone, and cyclohexanone (solvents containing -CO- but not -COO- in the molecule);

[0192] Butanol, cyclohexanol, propylene glycol and other alcohol solvents (solvents containing OH in the molecule but not -O-, -CO- and -COO-);

[0193] Amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; etc.

[0194] More preferably, the solvents are propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), ethyl lactate, and ethyl 3-ethoxypropionate.

[0195] When solvent (E) is included, the content of solvent (E) relative to the total amount of the coloring resin composition of the present invention is preferably 60 to 95% by mass, more preferably 65 to 92% by mass. In other words, the total amount of solid components in the coloring resin composition is preferably 5 to 40% by mass, more preferably 8 to 35% by mass. If the content of solvent (E) is within the above range, there is a tendency for improved flatness during coating and improved display properties when forming a color filter, as well as sufficient color concentration.

[0196] Leveling agent (F)

[0197] Examples of leveling agents (F) include silicone surfactants, fluorinated surfactants, and silicone surfactants containing fluorine atoms. They may have polymerizable groups in their side chains.

[0198] As organosilicon surfactants, examples include surfactants with intramolecular siloxane bonds. Specific examples include: Toray silicone DC3PA, Toray silicone SH7PA, Toray silicone DC11PA, Toray silicone SH21PA, Toray silicone SH28PA, Toray silicone SH29PA, Toray silicone SH30PA, Toray silicone 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 Advanced Materials Co., Ltd., Japan).

[0199] Examples of fluorinated surfactants include those with intramolecular fluorocarbon chains. Specific examples include: FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Co., Ltd.); MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Co., Ltd.); EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352 (manufactured by Mitsubishi Materials Electronics & Chemicals Co., Ltd.); SURFLON (registered trademark) S381, SURFLON S382, SURFLON SC101, SURFLON... SC105 (manufactured by Asahi Glass Co., Ltd.); and E5844 (manufactured by Daikin Seika Research Institute Co., Ltd.), etc.

[0200] As examples of organosilicon surfactants containing fluorine atoms, surfactants with intramolecular siloxane bonds and fluorocarbon chains can be cited. Specific examples include MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFACF475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation).

[0201] When a leveling agent (F) is included, the content of the leveling agent (F) relative to the total amount of the coloring resin composition is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass. It should be noted that this content does not include the content of the pigment dispersant. If the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0202] <Other Ingredients>

[0203] The coloring resin composition of the present invention may include fillers, polymers, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and other additives known in the art, as needed.

[0204] <Method for manufacturing coloring resin composition>

[0205] The coloring resin composition of the present invention can be manufactured by mixing a colorant (A) and a resin (B) and polymerizable compounds (C), polymerization initiators (D), polymerization initiation aids (D1), solvents (E), leveling agents (F) and other components as needed.

[0206] <Method for manufacturing color filters>

[0207] Methods for manufacturing colored patterns from the coloring resin composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred.

[0208] Because the coloring resin composition contains a colorant and a resin, and the colorant contains compound (I), it is possible to produce a color filter with excellent resistance to chemical reagents. This color filter is effective as a color filter used in display devices (e.g., liquid crystal displays, organic EL devices, electronic paper, etc.) and solid-state imaging elements.

[0209] [Example]

[0210] The present invention will now be described in more detail by way of examples, but the invention is not limited to these examples. In the examples, the percentages and parts representing the content and amount used are mass references unless otherwise specified.

[0211] [Synthesis example 1]

[0212] A nitrogen atmosphere was created by introducing an appropriate amount of nitrogen gas into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer. 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were then added, and the mixture was heated to 85°C while stirring. Next, 38 parts of acrylic acid and 3,4-epoxy tricyclic [5.2.1.0] were added dropwise over 5 hours. 2,6 [Dec-8-yl acrylate and 3,4-epoxy tricyclic [5.2.1.0]] 2,6 A mixed solution of 25 parts of a mixture of decyl-9-acrylate (containing 1:1 ratio), 137 parts of cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was prepared. On the other hand, a mixed solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the solution was maintained at the same temperature for 4 hours, then cooled to room temperature to obtain a copolymer (resin (B-1)) solution with a solid content of 25.6%. The produced copolymer had a weight-average molecular weight (Mw) of 8000, a dispersion of 2.1, and an acid value converted from solid content of 111 mg-KOH / g. Resin (B-1) has the following structural units.

[0213] [Chemical Formula 21]

[0214]

[0215] [Synthesis example 2]

[0216] A nitrogen atmosphere was created by introducing an appropriate amount of nitrogen gas into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer. 280 parts of propylene glycol monomethyl ether acetate were then added, and the mixture was heated to 80°C while stirring. Next, using a dropping pump, 38 parts of acrylic acid and 3,4-epoxy tricyclic [5.2.1.0] were added dropwise to the flask over 5 hours. 2,6 ] Decane-8-yl acrylate and 3,4-epoxy tricyclic [5.2.1.0] 2,6 A solution was prepared by dissolving 289 parts of a mixture of decane-9-yl acrylate (at a ratio of 1:1) in 125 parts of propylene glycol monomethyl ether acetate. Meanwhile, using a separate dropwise pump, a solution was added dropwise over 6 hours to a flask containing 33 parts of the polymerization initiator 2,2-azobis(2,4-dimethylpentanonitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate. After the addition was complete, the solution was maintained at the same temperature for 4 hours, then cooled to room temperature to obtain a copolymer (resin (B-2)) solution with a solids content of 35.1%. The produced copolymer had a weight-average molecular weight (Mw) of 9200, a dispersion of 2.08, and an acid value converted from solids content of 77 mg-KOH / g. Resin (B-2) has the following structural units.

[0217] [Chemical Formula 22]

[0218]

[0219] The determination of the polystyrene-converted weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin was performed by GPC under the following conditions.

[0220] Device: HLC-8120GPC (manufactured by Tosoh Corporation)

[0221] Column: TSK-GELG2000HXL

[0222] Column temperature: 40℃

[0223] Solvent: THF

[0224] Flow rate: 1.0 mL / min

[0225] Solid content concentration of the test solution: 0.001–0.01% by mass

[0226] Injection volume: 50μL

[0227] Detector: RI

[0228] Calibration standard materials: TSK standard polystyrene F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0229] The ratio of the weight-average molecular weight to the number-average molecular weight (Mw / Mn) of the polystyrene obtained above is used as the dispersity.

[0230] [Synthesis example 3]

[0231] Four parts of N,N-diethylamino-3-phenol, 0.5 parts of the compound represented by formula (B-1), and 7.4 parts of trifluorosulfonic acid were mixed and stirred at 100°C for 3 hours to obtain a reaction solution. After cooling the reaction solution to room temperature, 50 parts of water were added, and the mixture was extracted with chloroform and ethyl acetate. Each organic layer was washed with water. The washed organic layers were combined, and the solvent was removed by distillation. 0.9 parts of tetrachloro-p-benzoquinone and 50 parts of acetonitrile were added to the residue, and the mixture was stirred at room temperature for 12 hours. After removing the solvent by distillation, 50 parts of chloroform were added, and the precipitated solid was filtered and sieved. The filtrate was concentrated, and 50 parts of 4% sodium hydroxide aqueous solution were added to the concentrated filtrate. The mixture was stirred at room temperature for 12 hours. The reaction solution was neutralized to pH 4 with 2N hydrochloric acid, and the precipitated solid was filtered off. The obtained solid was dispersed and washed with an ethyl acetate-hexane (3:1) mixture for 3 hours, dried, and dissolved in 5 parts of concentrated hydrochloric acid to obtain a solution. The obtained solution was filtered, and the filtrate was crystallized out with 20% saline solution. The solution was then neutralized with 25% sodium hydroxide aqueous solution until the pH reached 4. The precipitated solid was filtered off and dried in a vacuum oven at 60°C to obtain 0.21 parts (24% yield) of the compound represented by formula (AY).

[0232] [Chemical Formula 23]

[0233]

[0234] [Chemical Formula 24]

[0235]

[0236] 0.77 parts of the compound represented by formula (AY), 0.5 parts of bis(trifluoromethanesulfonyl)lithium, and 12.3 parts of N,N-dimethyl sulfoxide were mixed and stirred at 50°C for 3 hours to obtain a reaction solution. The resulting reaction solution was added dropwise to 40 parts of 20% saline solution, and the precipitated solid was filtered off. The solid was dissolved in chloroform, the organic layer was washed with water, sodium sulfate was added, and the mixture was dried. The solvent was removed by distillation, and the mixture was dried in a vacuum oven at 60°C to obtain 0.73 parts of the compound represented by formula (A-2) (yield 76%). The mass analysis result of the obtained compound was m / z = 654 [M]. + It should be noted that for quality analysis, the LC was determined using an Agilent 1200 model, and the MASS was determined using an Agilent LC / MSD6130 model (the same applies to the quality analysis below).

[0237] [Chemical Formula 25]

[0238]

[0239] [Synthesis example 4]

[0240] Three parts of the compound represented by formula (A-2), five parts of ethyl 4-aminobenzoate, six parts of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.5 parts of 4-dimethylaminopyridine, 0.4 parts of (+)-10-camphorsulfonic acid, and 156 parts of dimethyl sulfoxide were mixed and stirred at room temperature for 3 hours. The reactants were crystallized in saturated brine, and the precipitated solid was filtered off and washed three times with 100 parts of water. The solid was dried in a vacuum oven at 60°C to obtain 1.6 parts of the compound represented by formula (A-6) (yield 34%). The mass analysis result of the obtained compound, m / z = 892 [M] + .

[0241] [Chemical Formula 26]

[0242]

[0243] [Synthesis example 5]

[0244] By replacing ethyl 4-aminobenzoate with aniline, and otherwise proceeding in the same manner as in Synthesis Example 4, 2.0 parts (42% yield) of the compound represented by formula (A-7) were obtained. The mass analysis results of the obtained compound, m / z = 804 [M], were obtained. + .

[0245] [Chemical Formula 27]

[0246]

[0247] [Synthesis Example 6]

[0248] 0.6 parts of 3-hydroxydiphenylamine, 0.6 parts of the compound represented by formula (B-1) above, and 8.8 parts of trifluoromethanesulfonic acid were mixed and stirred at 100°C for 4 hours to obtain a reaction solution. After cooling the reaction solution to room temperature, 50 parts of water were added, and the mixture was extracted with chloroform and ethyl acetate. The organic layers were washed with water. The washed organic layers were combined, and the solvent was removed by distillation. 0.6 parts of tetrachloro-p-benzoquinone and 11 parts of acetonitrile were added to the residue, and the mixture was stirred at room temperature for 10 hours. After removing the solvent by distillation, 30 parts of chloroform were added, and the precipitated solid was filtered and sieved. The filtrate was concentrated, and 20 parts of 4% sodium hydroxide aqueous solution were added to the concentrated filtrate. The mixture was stirred at room temperature for 12 hours. The reaction solution was neutralized to pH 4 with 2N hydrochloric acid, and the precipitated solid was filtered off. The obtained solid was dispersed and washed with an ethyl acetate-hexane (3:1) mixed solution for 5 hours, dried, and dissolved in 5 parts of concentrated hydrochloric acid to obtain a solution. The obtained solution was filtered, and the filtrate was crystallized out with 20% saline solution. The solution was then neutralized with 25% sodium hydroxide aqueous solution until the pH reached 4. The precipitated solid was filtered off and mixed with 7.6 parts of iodoethane, 4.1 parts of potassium carbonate, and 5 parts of N-methyl-2-pyrrolidone. The mixture was stirred at 75°C for 17 hours. After cooling the reaction solution to room temperature, 70 parts of 2N hydrochloric acid were added, and the solution was extracted with chloroform. The organic layer was washed with water, and the solvent was removed by distillation. The solution was dried in a vacuum oven at 60°C to obtain 0.2 parts (yield 15%) of the compound represented by formula (B-2). The mass analysis result of the obtained compound was m / z = 750 [M]. + .

[0249] Next, 0.2 parts of the compound represented by formula (B-2), 0.1 parts of bis(trifluoromethanesulfonyl)lithium, and 2.7 parts of N,N-dimethyl sulfoxide were mixed and stirred at 50°C for 5 hours to obtain a reaction solution. The obtained reaction solution was added dropwise to 40 parts of 20% saline solution, and the precipitated solid was filtered off. The solid was dissolved in chloroform, the organic layer was washed with water, sodium sulfate was added, and the mixture was dried and then solvent distilled off. The solution was dried in a vacuum oven at 60°C to obtain 0.2 parts of the compound represented by formula (A-8) (yield 90%).

[0250] [Chemical Formula 28]

[0251]

[0252] [Chemical Formula 29]

[0253]

[0254] [Synthesis Example 7]

[0255] 15.0 parts of 3,5-dichloroaniline, 19.9 parts of ethyl 4-bromobutyrate, 35.9 parts of N,N-diisopropylethylamine, and 52.5 parts of N,N-dimethylformamide were mixed and heated and stirred at 120°C for 2 hours. Next, 28.9 parts of iodoethane were added to the reaction solution, and the mixture was heated and stirred at 70°C for 24 hours. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and then washed with water. The organic layer was removed by solvent distillation, and the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate: hexane = 1:5). Further, 28.4 parts of phosphoryl chloride and 52.5 parts of N,N-dimethylformamide were mixed with the obtained compound at 0°C and heated and stirred at 60°C for 6 hours. The reaction mixture was crystallized in a 4% sodium hydroxide aqueous solution, and the precipitated solid was filtered off and washed with 100 parts of methanol. The compound was dried in a vacuum oven at 60 °C to obtain 5.0 parts (yield 16%) of the compound represented by formula (B-3). The mass analysis result of the obtained compound was m / z = 333 [M+H]. + .

[0256] [Chemical Formula 30]

[0257]

[0258] The compound represented by formula (B-1) was replaced with the compound represented by formula (B-3), and 3-hydroxydiphenylamine was replaced with N,N-diethylaminophenol. Otherwise, the procedure was the same as in Synthesis Example 6, yielding 1.3 parts (31% yield) of the compound represented by formula (B-4). The mass analysis results of the obtained compound, m / z = 596 [M], were obtained. + .

[0259] [Chemical Formula 31]

[0260]

[0261] Next, the compound represented by formula (B-2) was changed to the compound represented by formula (B-4), and otherwise the same procedure was followed as in synthesis example 6, to obtain 0.4 parts of the compound represented by formula (A-9) (yield 64%).

[0262] [Chemical Formula 32]

[0263]

[0264] [Synthesis example 8]

[0265] By replacing bis(trifluoromethanesulfonyl)lithium with monosodium 3-sulfobenzoate, the same procedure as in Synthesis Example 7 was followed to obtain 0.3 parts (45% yield) of the compound represented by formula (A-10).

[0266] [Chemical Formula 33]

[0267]

[0268] [Synthesis Example 9]

[0269] By replacing bis(trifluoromethanesulfonyl)lithium with bis(fluorosulfonyl)imidelithium, the same procedure as in Synthesis Example 3 was followed to obtain 0.88 parts (91% yield) of the compound represented by formula (A-11).

[0270] [Chemical Formula 34]

[0271]

[0272] [Synthesis Example 10]

[0273] By replacing bis(trifluoromethanesulfonyl)lithium with lithium trifluoromethanesulfonate, the same procedure as in Synthesis Example 3 was followed to obtain 0.77 parts (71% yield) of the compound represented by formula (A-12).

[0274] [Chemical Formula 35]

[0275]

[0276] [Synthesis Example 11]

[0277] By replacing bis(trifluoromethanesulfonyl)lithium with lithium nonafluoro-1-butanesulfonate, the same procedure as in Synthesis Example 3 was followed to obtain 0.5 parts (72% yield) of the compound represented by formula (A-13).

[0278] [Chemical Formula 36]

[0279]

[0280] [Synthesis Example 12]

[0281] By replacing bis(trifluoromethanesulfonyl)lithium with sodium tetraphenylborate, the same procedure as in Synthesis Example 3 was followed to obtain 0.93 parts (83% yield) of the compound represented by formula (A-14).

[0282] [Chemical Formula 37]

[0283]

[0284] [Synthesis Example 13]

[0285] By replacing bis(trifluoromethanesulfonyl)lithium with sodium dicyandiamide, the same procedure as in Synthesis Example 3 was followed to obtain 0.78 parts (93% yield) of the xaton compound represented by formula (A-15).

[0286] [Chemical Formula 38]

[0287]

[0288] [Synthesis Example 14]

[0289] By replacing bis(trifluoromethanesulfonyl)lithium with lithium hexafluorophosphate, the same procedure as in Synthesis Example 3 was followed to obtain 0.58 parts (63% yield) of the compound represented by formula (A-16).

[0290] [Chemical Formula 39]

[0291]

[0292] [Synthesis Example 15]

[0293] By replacing bis(trifluoromethanesulfonyl)lithium with sodium 3-nitrobenzenesulfonate, the same procedure as in Synthesis Example 3 was followed to obtain 0.74 parts (75% yield) of the compound represented by formula (A-17).

[0294] [Chemical Formula 40]

[0295]

[0296] [Synthesis Example 16]

[0297] By replacing bis(trifluoromethanesulfonyl)lithium with sodium isoquinoline-5-sulfonate, the same procedure as in Synthesis Example 3 was followed to obtain 0.65 parts (63% yield) of the compound represented by formula (A-18).

[0298] [Chemical Formula 41]

[0299]

[0300] [Synthesis Example 17]

[0301] By replacing bis(trifluoromethanesulfonyl)lithium with trifluoromethanesulfonamide, the same procedure as in Synthesis Example 3 was followed to obtain 0.74 parts (75% yield) of the compound represented by formula (A-19).

[0302] [Chemical Formula 42]

[0303]

[0304] [Synthesis Example 18]

[0305] By replacing bis(trifluoromethanesulfonyl)lithium with N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid, the same procedure as in Synthesis Example 3 was followed to obtain 0.87 parts (87% yield) of the compound represented by formula (A-20).

[0306] [Chemical Formula 43]

[0307]

[0308] [Synthesis Example 19]

[0309] By replacing bis(trifluoromethanesulfonyl)lithium with ethylenediaminetetraacetic acid monosodium iron(III) hydrate, the same procedure as in Synthesis Example 3 was followed to obtain 0.65 parts (60% yield) of the compound represented by formula (A-21).

[0310] [Chemical Formula 44]

[0311]

[0312] [Synthesis Example 20]

[0313] By replacing bis(trifluoromethanesulfonyl)lithium with sodium vinylsulfonate, the same procedure as in Synthesis Example 3 was followed to obtain 0.65 parts (74% yield) of the compound represented by formula (A-22).

[0314] [Chemical Formula 45]

[0315]

[0316] [Synthesis Example 21]

[0317] The bis(trifluoromethanesulfonyl)lithium was replaced with a solution of 3-(trihydroxysilyl)propylmethylphosphonic acid monosodium salt, and the same procedure was followed as in Synthesis Example 3 to obtain 0.47 parts (46% yield) of the compound represented by formula (A-23).

[0318] [Chemical Formula 46]

[0319]

[0320] [Synthesis Example 22]

[0321] By replacing bis(trifluoromethanesulfonyl)lithium with 3-(trihydroxysilyl)propane-1-sulfonic acid, the same procedure as in Synthesis Example 3 was followed to obtain 0.32 parts (36% yield) of the xaton compound represented by formula (A-24).

[0322] [Chemical Formula 47]

[0323]

[0324] [Synthesis Example 23]

[0325] 0.2 parts of 1,8-naphthalenesulfone, 0.2 parts of 3-aminopropyltriethoxysilane, and 8.5 parts of dimethyl sulfoxide were mixed and stirred at room temperature for 3 hours to obtain the compound represented by formula (B-5). Then, bis(trifluoromethanesulfonyl)lithium was replaced with the compound represented by formula (B-5), and the same procedure as in Synthesis Example 3 was followed to obtain 0.78 parts of the compound represented by formula (A-25) (yield 93%).

[0326] [Chemical Formula 48]

[0327]

[0328] [Chemical Formula 49]

[0329]

[0330] [Synthesis Example 24]

[0331] The 1,8-naphthalene sulfone was replaced with sodium 1,8-naphthalene sulfone-4-sulfonate, and the same procedure was followed as in Synthesis Example 23 to obtain 0.5 parts (44% yield) of the compound represented by formula (A-26).

[0332] [Chemical Formula 50]

[0333]

[0334] [Synthesis Example 25]

[0335] By replacing bis(trifluoromethanesulfonyl)lithium with phosphotungstic acid hydrate, and otherwise proceeding in the same manner as in Synthesis Example 3, 0.5 parts of the compound represented by formula (A-27) were obtained (72% yield).

[0336] [Chemical Formula 51]

[0337]

[0338] [Synthesis Example 26]

[0339] By replacing bis(trifluoromethanesulfonyl)lithium with lithium 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonylimide, the same procedure as in Synthesis Example 3 was followed to obtain 0.69 parts (63% yield) of the xaton compound represented by formula (A-28).

[0340] [Chemical Formula 52]

[0341]

[0342] [Synthesis Example 27]

[0343] By replacing bis(trifluoromethanesulfonyl)lithium with potassium tri(trifluoromethanesulfonyl)methanide, the same procedure as in Synthesis Example 3 was followed to obtain 0.63 parts (58% yield) of the compound represented by formula (A-29).

[0344] [Chemical Formula 53]

[0345]

[0346] [Preparation of Dispersion 1]

[0347] 10.0 parts of CI Pigment Red 291 (pigment), 3.3 parts of dispersant (BYK LPN-6919; 60% solution of propylene glycol monomethyl ether acetate), 4.0 parts of resin (B-2) (solid component conversion), and 12.7 parts of propylene glycol monomethyl ether were mixed, along with 41.3 parts of propylene glycol monomethyl ether acetate. 600 parts of 0.4 μm zirconium dioxide beads were added, and the mixture was shaken for 1 hour using a paint mixer (LAU). The zirconium dioxide beads were then removed by filtration to obtain dispersion 1.

[0348] [Preparation of Dispersion 2]

[0349] 10.0 parts of CI Pigment Red 177 (pigment), 4.3 parts of dispersant (BYK LPN-6919; 60% propylene glycol monomethyl ether acetate solution), 4.0 parts of resin (B-2) (solid component conversion), and 59.2 parts of propylene glycol monomethyl ether acetate were mixed. 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint mixer (LAU). The zirconia beads were then removed by filtration to obtain dispersion 2.

[0350] [Preparation of Dispersion 3]

[0351] 10.0 parts of CI Pigment Red 202 (pigment), 7.5 parts of dispersant (BYK LPN-6919; 60% propylene glycol monomethyl ether acetate solution), 3.5 parts of resin (B-2) (solid component conversion), 8.5 parts of propylene glycol monomethyl ether, and 202 parts of propylene glycol monomethyl ether acetate were mixed, and 600 parts of 0.4 μm zirconium dioxide beads were added. The mixture was shaken for 1 hour using a paint mixer (LAU). Then, the zirconium dioxide beads were removed by filtration to obtain dispersion 3.

[0352] [Preparation of Dispersion 4]

[0353] 10.0 parts of CI Pigment Red 264 (pigment), 7.6 parts of dispersant (BYK LPN-6919; 60% solution of propylene glycol monomethyl ether acetate), 3.6 parts of resin (B-2) (solid component conversion), 6.7 parts of propylene glycol monomethyl ether, and 55.4 parts of propylene glycol monomethyl ether acetate were mixed, and 600 parts of 0.4 μm zirconium dioxide beads were added. The mixture was shaken for 1 hour using a paint mixer (LAU). Then, the zirconium dioxide beads were removed by filtration to obtain dispersion 4.

[0354] [Preparation of Dispersion 5]

[0355] 10.0 parts of CI Pigment Red 269 (pigment), 5.0 parts of dispersant (BYK LPN-6919; 60% propylene glycol monomethyl ether acetate solution), 3.0 parts of resin (B-2) (solid component conversion), 5.5 parts of propylene glycol monomethyl ether, and 47.7 parts of propylene glycol monomethyl ether acetate were mixed, and 600 parts of 0.4 μm zirconium dioxide beads were added. The mixture was shaken for 1 hour using a paint mixer (LAU). Then, the zirconium dioxide beads were removed by filtration to obtain dispersion 5.

[0356] [Preparation of Dispersion 6]

[0357] 10.0 parts of CI Pigment Yellow 185 (pigment), 10.8 parts of dispersant (BYK LPN-6919; 60% solution of propylene glycol monomethyl ether acetate), 3.5 parts of resin (B-2) (solid component conversion), 4.2 parts of propylene glycol monomethyl ether, and 96.5 parts of propylene glycol monomethyl ether acetate were mixed, and 600 parts of 0.4 μm zirconia beads were added. The mixture was shaken for 1 hour using a paint mixer (LAU). Then, the zirconia beads were removed by filtration to obtain dispersion 6.

[0358] [Preparation of Dispersion 7]

[0359] 10.0 parts of CI Pigment Blue 15:6 (pigment), 5.8 parts of dispersant (BYK LPN-6919; 60% propylene glycol monomethyl ether acetate solution), 4.0 parts of resin (B-2) (solid component conversion), 7.6 parts of ethyl lactate, and 96.5 parts of propylene glycol monomethyl ether acetate were mixed, and 600 parts of 0.4 μm zirconia beads were added. The mixture was shaken for 1 hour using a paint mixer (LAU). Then, the zirconia beads were removed by filtration to obtain dispersion 7.

[0360] <Examples 1-36, Comparative Examples 1 and 2>

[0361] [Preparation of the coloring resin composition]

[0362] The components shown in Tables 5 to 7 are mixed to obtain the various colored resin compositions.

[0363] • Pigment 1: The compound represented by formula (A-1)

[0364] [Chemical Formula 54]

[0365]

[0366] • Pigment 2: The compound represented by formula (A-2)

[0367] [Chemical Formula 55]

[0368]

[0369] • Pigment 3: The compound represented by formula (A-3)

[0370] [Chemical Formula 56]

[0371]

[0372] • Pigment 4: The compound represented by formula (A-4)

[0373] [Chemical Formula 57]

[0374]

[0375] • Pigment 5: Compound represented by formula (AX)

[0376] [Chemical Formula 58]

[0377]

[0378] • Pigment 6: The compound represented by formula (A-6)

[0379] • Pigment 7: The compound represented by formula (A-7)

[0380] • Pigment 8: The compound represented by formula (A-8)

[0381] • Pigment 9: The compound represented by formula (A-9)

[0382] • Pigment 10: The compound represented by formula (A-10)

[0383] • Pigment 11: The compound represented by formula (A-11)

[0384] • Pigment 12: The compound represented by formula (A-12)

[0385] • Pigment 13: The compound represented by formula (A-13)

[0386] • Pigment 14: The compound represented by formula (A-14)

[0387] • Pigment 15: The compound represented by formula (A-15)

[0388] • Pigment 16: The compound represented by formula (A-16)

[0389] • Pigment 17: The compound represented by formula (A-17)

[0390] • Pigment 18: The compound represented by formula (A-18)

[0391] • Pigment 19: The compound represented by formula (A-19)

[0392] • Pigment 20: The compound represented by formula (A-20)

[0393] • Pigment 21: The compound represented by formula (A-21)

[0394] • Pigment 22: The compound represented by formula (A-22)

[0395] • Pigment 23: The compound represented by formula (A-23)

[0396] • Pigment 24: The compound represented by formula (A-24)

[0397] • Pigment 25: The compound represented by formula (A-25)

[0398] • Pigment 26: The compound represented by formula (A-26)

[0399] • Pigment 27: The compound represented by formula (A-27)

[0400] • Pigment 28: The compound represented by formula (A-28)

[0401] • Pigment 29: Compound represented by formula (A-29)

[0402] • Resin (B): Resin (B-1) (Conversion of solid components)

[0403] • Polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)

[0404] • Polymerization initiator (D): TR-PBG327 (registered trademark) (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.; oxime compound)

[0405] • Solvent (E): Solvent (E-1): Ethyl lactate

[0406] Solvent (E-2): Diacetone alcohol

[0407] Solvent (E-3): Propylene glycol monomethyl ether acetate

[0408] Leveling agent (F): Polyether modified silicone oil (solids conversion) (Toray silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0409] [Table 5]

[0410]

[0411] [Table 6]

[0412]

[0413] [Table 7]

[0414]

[0415] [Preparation of color filters (color coatings)]

[0416] The colored resin composition was spin-coated onto a 5cm square glass substrate (Eagle 2000; Corning Incorporated) and then baked at 100°C for 3 minutes to form a colored resin composition layer. After cooling, it was exposed to atmospheric pressure at 60mJ / cm² using an exposure machine (TME-150RSK; Topcon Co., Ltd.). 2 The filter is then irradiated with light at an exposure level (365nm reference). It is then baked in an oven at 230°C for 20 minutes to obtain the color filter.

[0417] [Chemical resistance test]

[0418] The obtained color filters were immersed in N-methylpyrrolidone at 40°C for 10 minutes. The spectra of the filters before and after immersion were measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation). The xy chromaticity coordinates (x, y) and stimulus value Y in the CIE XYZ colorimetric system were calculated using the characteristic function of the C light source. The color difference ΔE*ab was calculated from these measured values ​​using the method described in JIS Z 8730:2009 (7. Calculation method of color difference), and the results are shown in Tables 8 and 9. The smaller ΔE*ab is, the smaller the color difference.

[0419] [Table 8]

[0420] ⊿E*ab Example 1 1.6 Example 2 1.2 Example 3 1.1 Comparative Example 1 6.8 Example 4 4.7 Example 5 3.9 Example 6 3.0 Example 7 2.7 Example 8 1.9 Example 9 2.7 Example 10 0.6 Example 11 0.9 Example 12 1.7 Comparative Example 1 10.5

[0421] [Table 9]

[0422] ⊿E*ab Example 13 0.5 Example 14 4.3 Example 15 0.7 Example 16 5.3 Example 17 3.9 Example 18 1.9 Example 19 3.7 Example 20 3.8 Example 21 2.6 Example 22 2.4 Example 23 3.8 Example 24 1.1 Example 25 1.2 Example 26 3.9 Example 27 0.6 Example 28 1.1 Example 29 2.4 Example 30 1.2 Example 31 1.3 Example 32 1.3 Example 33 1.1 Example 34 1.1 Example 35 2.0 Example 36 1.8 Comparative Example 1 Comparative Example 1 6.8

Claims

1. A coloring resin composition comprising a colorant and a resin, said colorant comprising a compound represented by formula (I), In formula (I), R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 and R 10 Each group independently represents a hydrogen atom, hydroxyl group, nitro group, cyano group, halogen atom, carboxyl group, sulfonyl group, aminosulfonyl group, metallocene group, hydrocarbon group with 1 to 30 carbon atoms, or a group in which one or more methylene groups are substituted by divalent groups selected from group I of the following: When two or more methylene groups are substituted with divalent groups selected from group I, the divalent groups are not adjacent. The hydrogen atoms contained in the hydrocarbon group are substituted or unsubstituted by halogen atoms, nitro groups, cyano groups, hydroxyl groups, amino groups, carboxyl groups, sulfonyl groups, phosphonyl groups, aminosulfonyl groups, isocyanate groups, heterocyclic groups, or other compounds. R 11 R 12 R 13 R 14 R 15 and R 16 Each group independently represents a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or more methylene groups are substituted with divalent groups selected from group I, wherein when two or more methylene groups are substituted with divalent groups selected from group I, the divalent groups are not adjacent. The hydrogen atoms contained in the hydrocarbon group are either substituted or unsubstituted by heterocyclic or polar groups. R 11 R 12 R 13 R 14 R 15 and R 16 One or more of the groups are substituents having a polar group, wherein the polar group is selected from one or more groups represented by formulas (po-1) to (po-6). n represents an integer from 1 to 3. A q- This indicates anion with a valence of q. q represents an integer from 1 to 3. p represents the coefficient that maintains the charge of the compound represented by equation (I) to be neutral. Group I: -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO2-, -SO3-, -NH-, -CONH-, -NHCO-, -SO2NH-, -NHSO2- or -N=CH-, 2. The coloring resin composition according to claim 1, further comprising a polymerizable compound and a polymerization initiator.

3. The coloring resin composition according to claim 1 or 2, wherein the colorant further comprises a pigment, wherein, Exclude the compound represented by formula (I).

4. A color filter formed from the coloring resin composition according to any one of claims 1 to 3.

5. A display device comprising the color filter of claim 4.

Images