Compound, colored resin composition, colored curable resin composition, color filter, display device, and solid-state imaging device

Abstract

The present invention addresses the problem of providing a compound that can be used to form a color filter having excellent light resistance. The present invention relates to a compound represented by formula (I). [In formula (I), R1 represents a monovalent hydrocarbon group having 21-40 carbon atoms. And R3 represents a monovalent hydrocarbon group having 6 to 40 carbon atoms. And R2 and R4 represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1-6 carbon atoms. And R5 represents-OH,-SO3-,-SO3H,-CO2H, or the like. And R6 and R7 represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1-6 carbon atoms. And m represents an integer of 0-5. And a represents an integer of 0 or 1. And X represents a halogen atom. ]

Description

Technical Field

[0001] This invention relates to compounds, coloring resin compositions, coloring curable resin compositions, color filters, display devices, and solid-state imaging devices. Background Technology

[0002] Color filters (optical filters) used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays; and solid-state imaging devices such as CCD and CMOS sensors can be manufactured from coloring (curing) resin compositions. As such compositions, compositions containing colorants, resins, etc. are known (for example, Patent Document 1).

[0003] Existing technical documents Patent documents Patent Document 1: Japanese Patent Application Publication No. 2021-162854 Summary of the Invention

[0004] The problem that the invention aims to solve For color filters used in display devices, solid-state imaging devices, and the like, sufficient lightfastness is required from the perspective of the operating environment. However, the lightfastness of conventional color filters may not be sufficient, leaving room for improvement.

[0005] Therefore, the main objective of the present invention is to provide a compound that can be used to form a color filter with excellent lightfastness; and to provide a color-curing resin composition that can form a color filter with excellent lightfastness.

[0006] Methods for solving problems The present invention provides the compound described in [1], the coloring resin composition described in [2], the coloring curable resin composition described in [3], the color filter described in [4], the display device described in [5], and the solid-state imaging device described in [6].

[0007] [1] The compound represented by formula (I).

[0008] In formula (I), R 1 It represents a monovalent hydrocarbon group with 21 to 40 carbon atoms.

[0009] R 3 It represents a monovalent hydrocarbon group with 6 to 40 carbon atoms.

[0010] R 2 and R 4 Each group independently represents a monovalent saturated hydrocarbon group with 1 to 6 hydrogen or carbon atoms.

[0011] R 5Indicates -OH, -SO3 - -SO3H, -SO3 - Z + -CO2H, -CO2 - Z + -CO2R 8 -SO3R 8 or -SO2NR 9 R 10 .

[0012] R 6 and R 7 Each group independently represents a monovalent saturated hydrocarbon group with 1 to 6 hydrogen or carbon atoms.

[0013] m represents an integer from 0 to 5. When m is greater than 2, multiple R... 5 They can be the same or different.

[0014] 'a' represents the integer 0 or 1.

[0015] X represents a halogen atom.

[0016] Z + N represents + (R) 11 4. Na + or K + 4 Rs 11 They can be the same or different.

[0017] R 8 It represents a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms, in which the hydrogen atoms can be replaced by halogen atoms.

[0018] R 9 and R 10 Each of the above can independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms that may have substituents, wherein the -CH2- group contained in the saturated hydrocarbon group may be replaced by -O-, -CO-, -NH- or -NR. 8 -. R 9 and R 10 They can bond with each other and together with adjacent nitrogen atoms to form heterocycles with 3 to 10 members.

[0019] R 11 This refers to a hydrogen atom, a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms, or an aralkyl group with 7 to 10 carbon atoms. [2] A coloring resin composition containing a colorant and a resin, The aforementioned colorant comprises the compound represented by formula (I) as described in [1].

[0020] [3] A coloring and curing resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator. The aforementioned colorant comprises the compound represented by formula (I) as described in [1].

[0021] [4] A color filter formed from the color curing resin composition described in [3].

[0022] [5] A display device comprising the color filter described in [4].

[0023] [6] A solid-state imaging device comprising the color filter described in [4].

[0024] Invention Effects According to the present invention, compounds capable of forming color filters with excellent lightfastness can be provided. Furthermore, according to the present invention, color-curing resin compositions capable of forming color filters with excellent lightfastness can be provided. Additionally, according to the present invention, coloring resin compositions capable of being used to prepare color-curing resin compositions can be provided. Moreover, according to the present invention, color filters formed from such color-curing resin compositions, as well as display devices and solid-state imaging devices comprising such color filters, can be provided. Detailed Implementation

[0025] The embodiments of the present invention will now be described in detail. However, the present invention is not limited to the following embodiments.

[0026] In this specification, the numerical range indicated by "~" represents the range in which the values ​​before and after "~" are respectively the minimum and maximum values. Within the numerical ranges described in stages in this specification, the upper or lower limit value described in one numerical range can be replaced by the upper or lower limit value of other numerical ranges described in stages. Furthermore, within the numerical ranges described in this specification, the upper or lower limit value can be replaced by the values ​​shown in the embodiments.

[0027] In this specification, (meth)acrylate means acrylate or the corresponding methacrylate. The same applies to other similar expressions such as (meth)acrylic acid, (meth)acryloyl, (meth)acrylate class.

[0028] Unless otherwise specified, the materials exemplified below in this specification may be used individually or in combination of two or more, within the permitted scope. Regarding the content of each component, in the case of multiple substances belonging to each component, unless otherwise specified, the content refers to the total amount of all substances.

[0029] [Compound] The compound in this embodiment is the compound represented by formula (I) (hereinafter sometimes referred to as "compound (I)"). It should be noted that compound (I) may exist as isomers such as tautomers, and these isomers are also included within the scope of this invention.

[0030] In formula (I), R 1 It represents a monovalent hydrocarbon group with 21 to 40 carbon atoms.

[0031] R 3 It represents a monovalent hydrocarbon group with 6 to 40 carbon atoms.

[0032] R 2 and R 4 Each group independently represents a monovalent saturated hydrocarbon group with 1 to 6 hydrogen or carbon atoms.

[0033] R 5 Indicates -OH, -SO3 - -SO3H, -SO3 - Z + -CO2H, -CO2 - Z + -CO2R 8 -SO3R 8 or -SO2NR 9 R 10 .

[0034] R 6 and R 7 Each group independently represents a monovalent saturated hydrocarbon group with 1 to 6 hydrogen or carbon atoms.

[0035] m represents an integer from 0 to 5. When m is greater than 2, multiple R... 5 They can be the same or different.

[0036] 'a' represents the integer 0 or 1.

[0037] X represents a halogen atom.

[0038] Z + N represents + (R) 11 4. Na + or K + 4 Rs 11 They can be the same or different.

[0039] R 8 It represents a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms, in which the hydrogen atoms can be replaced by halogen atoms.

[0040] R 9and R 10 Each of the above can independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms that may have substituents, wherein the -CH2- group contained in the saturated hydrocarbon group may be replaced by -O-, -CO-, -NH- or -NR. 8 -. R 9 and R 10 They can bond with each other and together with adjacent nitrogen atoms to form heterocycles with 3 to 10 members.

[0041] R 11 It represents a hydrogen atom, a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms, or an aralkyl group with 7 to 10 carbon atoms.

[0042] R 3 The monovalent hydrocarbon group with 6 to 40 carbon atoms is preferably a monovalent aromatic hydrocarbon group with 6 to 40 carbon atoms that may have substituents. Here, the number of carbon atoms in the monovalent aromatic hydrocarbon group also includes the number of carbon atoms in the substituents, and is 6 to 40.

[0043] As R 3 The monovalent aromatic hydrocarbon group in the figure can be, for example, a group obtained by removing one hydrogen atom that is directly bonded to the carbon atom constituting the ring from a monocyclic aromatic hydrocarbon (e.g., benzene) or a polycyclic aromatic hydrocarbon (e.g., 2-cyclic aromatic hydrocarbons such as naphthalene, indene, naphthoquinone, dihydroindene, and naphthoquinone; 3-cyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, fluorene, anthraquinone, phenanthrene, and fluorene; 4-cyclic aromatic hydrocarbons such as benzo[anthracene], benzo[phenanthrene], benzo[fluorene], pyrene, and fluoranthracene; 5-cyclic aromatic hydrocarbons such as dibenzo[anthracene], dibenzo[phenanthrene], dibenzo[fluorene], indene, perylene, and benzo[fluoranthracene; and 6-cyclic aromatic hydrocarbons such as spirobisfluorene). Examples of monovalent aromatic hydrocarbon groups include those obtained by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon (non-fused polycyclic aromatic hydrocarbon) formed by multiple bonds among these aromatic hydrocarbons. Examples of non-fused polycyclic aromatic hydrocarbons include biphenyl, terphenyl (o-terphenyl, m-terphenyl, p-terphenyl), and phenylterphenyl. Examples of substituents that can be present in monovalent aromatic hydrocarbon groups include halogen atoms, -OH, and -OR. 8 -SO3 - -SO3H, -SO3 - Z + -CO2H, -CO2R 8 -SR 8 -SO2R 8 -SO3R 8 -SO2NR 9 R 10 and -Si (OR) 12 (OR) 13 (OR) 14 R 12 R13 and R 14 Each of these groups independently represents a monovalent saturated hydrocarbon group with 1 to 4 carbon atoms, in which the hydrogen atoms can be replaced by halogen atoms.

[0044] R 3 The aromatic hydrocarbon with a monovalent aromatic hydrocarbon group is preferably an aromatic hydrocarbon having 1 to 6 benzene rings, more preferably an aromatic hydrocarbon having 2 to 5 benzene rings, and even more preferably an aromatic hydrocarbon having 2 to 4 benzene rings. The aromatic hydrocarbon having 2 to 4 benzene rings can be, for example, biphenyl, terphenyl, or phenylterphenyl. It should be noted that in fused benzene formed by the fusion of benzene rings, the number of fused benzene rings is the number of benzene rings. For example, in naphthalene formed by the fusion of 2 benzene rings, the benzene rings are counted as 2. Furthermore, in bonded benzene formed by the bonding of benzene rings, the number of bonded benzene rings is the number of benzene rings. For example, in biphenyl formed by the bonding of 2 benzene rings, the benzene rings are counted as 2.

[0045] R 3 Preferably, it is a group obtained by removing one hydrogen atom that is directly bonded to the carbon atom constituting the ring from at least one aromatic hydrocarbon selected from the group consisting of benzene, biphenyl, terphenyl and phenylterphenyl; more preferably, it is a group obtained by removing one hydrogen atom that is directly bonded to the carbon atom constituting the ring from at least one aromatic hydrocarbon selected from the group consisting of biphenyl, terphenyl and phenylterphenyl.

[0046] R 1 The monovalent hydrocarbon group with 21 to 40 carbon atoms is preferably a monovalent aromatic hydrocarbon group with 21 to 40 carbon atoms that may have substituents. Here, the number of carbon atoms in the monovalent aromatic hydrocarbon group also includes the number of carbon atoms in the substituents and is 21 to 40.

[0047] As R 1 The monovalent aromatic hydrocarbon group in, for example, can be exemplified in R 3 The exemplified groups among the monovalent aromatic hydrocarbon groups are monovalent aromatic hydrocarbon groups with 21 to 40 carbon atoms.

[0048] R 1 The aromatic hydrocarbon with a monovalent aromatic hydrocarbon group is preferably an aromatic hydrocarbon having 4 to 6 benzene rings, more preferably an aromatic hydrocarbon having 4 or 5 benzene rings, and even more preferably an aromatic hydrocarbon having 4 benzene rings. An aromatic hydrocarbon having 4 benzene rings can be, for example, phenyl terphenyl.

[0049] R 1 Preferably, it is a group obtained by removing one hydrogen atom that is directly bonded to the carbon atom constituting the ring from phenyl terphenyl.

[0050] As R 2 and R4 The alkyl group is a monovalent saturated hydrocarbon group with 1 to 6 carbon atoms. Examples include straight-chain alkyl groups such as methyl, ethyl, propyl, pentyl, and hexyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, and neopentyl; and cyclic alkyl groups such as cyclopropyl, cyclopentyl, and cyclohexyl.

[0051] As R 8 ~R 11 The alkyl group consisting of 1 to 20 carbon atoms is a monovalent saturated hydrocarbon group. Examples of such alkyl groups include straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl; and cyclic alkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl.

[0052] R 9 and R 10 The monovalent saturated hydrocarbon group with 1 to 20 carbon atoms can have substituents. Examples of such substituents include hydroxyl groups and halogen atoms.

[0053] As R 12 ~R 14 The alkyl group is a monovalent saturated hydrocarbon group with 1 to 4 carbon atoms. Examples include straight-chain alkyl groups such as methyl, ethyl, propyl, and butyl; branched alkyl groups such as isopropyl and isobutyl; and cyclic alkyl groups such as cyclopropyl.

[0054] Z + For N + (R) 11 4. Na + or K + N is preferred + (R) 11 4. Preferred N + (R) 11 The four R's in 4 11 At least two of them are monovalent saturated hydrocarbon groups with 5 to 20 carbon atoms. Additionally, there are four R... 11 The total number of carbon atoms is preferably 20 to 80, more preferably 20 to 60.

[0055] As -OR 8 Examples include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octyloxy, 2-ethylhexyloxy, and eicosyloxy.

[0056] As -CO2R 8 Examples include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, hexyloxycarbonyl, and eicosyloxycarbonyl.

[0057] As -SR8 Examples include methyl thio, ethyl thio, butyl thio, hexyl thio, decyl thio, eicosyl thio, etc.

[0058] As -SO2R 8 Examples include methylsulfonyl, ethylsulfonyl, butylsulfonyl, hexylsulfonyl, decylsulfonyl, and eicosylsulfonyl.

[0059] As -SO3R 8 Examples include methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, tert-butoxysulfonyl, hexyloxysulfonyl, and eicosyloxysulfonyl.

[0060] As -SO2NR 9 R 10 Examples include aminosulfonyl; N-methylaminosulfonyl, N-ethylaminosulfonyl, N-isopropylaminosulfonyl, N-butylaminosulfonyl, N-pentylaminosulfonyl, N-(1-ethylpropyl)aminosulfonyl, N-(1,1-dimethylpropyl)aminosulfonyl, N-(2-methylbutyl)aminosulfonyl, N-cyclopentylaminosulfonyl, N-hexylaminosulfonyl, N-(3,3-dimethylbutyl)aminosulfonyl, N-(1- N-1 substituted aminosulfonyl groups include methylhexyl)aminosulfonyl, N-octylaminosulfonyl, N-(2-ethylhexyl)aminosulfonyl, and N-(1,1,2,2-tetramethylbutyl)aminosulfonyl; and N,N-2 substituted aminosulfonyl groups include N,N-dimethylaminosulfonyl, N,N-ethylmethylaminosulfonyl, N,N-butylethylaminosulfonyl, N,N-bis(1-methylpropyl)aminosulfonyl, and N,N-heptylmethylaminosulfonyl.

[0061] As -Si(OR) 12 (OR) 13 (OR) 14 Examples include trimethoxysilyl and triethoxysilyl.

[0062] R 5 Preferred types are -CO2H and -CO2. - Z + -CO2R 8 -SO3 - -SO3 - Z + -SO3H or SO2NHR 9 SO3 is preferred. - -SO3 - Z + -SO3H or SO2NHR 9 .

[0063] m represents an integer from 0 to 5, preferably from 1 to 4, more preferably 1 or 2, and even more preferably 1.

[0064] As R 6 and R 7 Examples of monovalent saturated hydrocarbon groups with 1 to 6 carbon atoms in R can be found. 2 and R 4 The same group as the monovalent saturated hydrocarbon group with 1 to 6 carbon atoms in it. R 6 and R 7 The alkyl group having 1 to 6 carbon atoms can be, for example, an alkyl group having 1 or 2 carbon atoms. R 6 and R 7 Hydrogen atoms are preferred.

[0065] As R 11 Aryl groups with 7 to 10 carbon atoms include benzyl, phenylethyl, and phenylbutyl.

[0066] a is an integer, either 0 or 1, preferably 0.

[0067] Examples of halogen atoms in X include chlorine, fluorine, bromine, and iodine atoms. It should be noted that X... - It refers to halide ions.

[0068] As for compound (I), for example, compounds represented by formulas (I-1) to (I-8) can be cited. It should be noted that in the formulas, Ph refers to phenyl.

[0069] Compound (I) can be obtained, for example, by the following steps. First, in an organic solvent, the compound represented by formula (IA) is reacted with the compound represented by formula (IB) to obtain the compound represented by formula (IC). Next, in an organic solvent, the obtained compound represented by formula (IC) is reacted with the compound represented by formula (ID), thereby obtaining compound (I).

[0070] [Coloring Resin Composition] The coloring resin composition of this embodiment contains a colorant (hereinafter sometimes referred to as "colorant (A)") and a resin (hereinafter sometimes referred to as "resin (B)"). The coloring resin composition of this embodiment may also contain a solvent (hereinafter sometimes referred to as "solvent (C)"), other components, etc.

[0071] <Coloring Agent (A)> Colorant (A) comprises the compound represented by formula (I) above (hereinafter sometimes referred to as "colorant (A1)").

[0072] The content of colorant (A1), based on the total amount of colorant (A), is preferably 10-100% by mass, more preferably 30-100% by mass, even more preferably 50-100% by mass, and particularly preferably 70-100% by mass. In one embodiment, the content of colorant (A1) may be 100% by mass based on the total amount of colorant (A). When colorant (A1) is used as a toning agent for blue in the coloring resin composition, in one embodiment, the content of colorant (A1) may be 10-45% by mass or 20-35% by mass based on the total amount of colorant (A).

[0073] Colorant (A) may also contain a different colorant than colorant (A1) (hereafter referred to as "colorant (A2)").

[0074] As a coloring agent (A2), examples include dyes and pigments.

[0075] As dyes, examples include compounds classified as hues other than pigments in the Dye Index (published by The Society of Dyers and Colourists) and known dyes listed in the Dyeing Guide (Nishin Co., Ltd.).

[0076] Xanthan dyes are dyes containing compounds having a xanthan skeleton within the molecule (excluding compounds represented by formula (I) above). Examples of xanthan dyes include, for instance, C1 Acid Red 51 (hereinafter, the designation "C1 Acid Red" is omitted and only the number is listed. Similarly, other similar designations are sometimes only listed by number), 52, 87, 92, 94, 289, 388; C1 Acid Violet 9, 30, 102; C1 Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, 11; C1 Basic Violet 10 (Rhodamine B), 11; C1 Solvent Red 218; C1 Mordant Red 27; C1 Reactive Red 36 (Rose Red B); Sulforodamine G; xanthan dyes described in Japanese Patent Application Publication No. 2010-32999; xanthan dyes described in Japanese Patent Publication No. 4492760, etc. Xanton dyes are preferably dyes that are soluble in organic solvents.

[0077] Xanthon dyes can also be commercially available xanthon dyes (e.g., "Chugai AminolFast Pink RH / C" manufactured by Chugai Chemical Co., Ltd., and "Rhodamin 6G" manufactured by Taoka Chemical Co., Ltd.). Alternatively, xanthon dyes can be synthesized using commercially available xanthon dyes as starting materials, according to Japanese Patent Application Publication No. 2010-32999.

[0078] Other than xanthones, azo dyes, cyanine dyes, triphenylmethane dyes, thiazole dyes, oxazine dyes, phthalocyanine dyes, quinoline dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methylbenzene dyes, methylimine dyes, squaric acid onion dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes can be used. Known dyes can be used for each dye other than xanthones.

[0079] As specific examples of dyes other than succinate dyes, examples include CI Solvent Yellow 4 (hereinafter, the description of CI Solvent Yellow is omitted and only the number is recorded. Other similar descriptions are also sometimes only recorded by number), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI solvent green dyes 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 15 7, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 57, 66, 73, 76, 80, 88, 91, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Violet 6B, 7, 15, 16, 17, 19, 21, 23, 24, 25, 34, 38, 49, 72; Acid Blue (CI) 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; CI Acid Green includes Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, and other CI acid dyes. CI direct yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI direct red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI direct orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 16 7, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Green includes CI direct dyes such as 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, and 82. CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI disperse blue 1, 14, 56, 60, and other CI disperse dyes. CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic Red 1, 9, 10; CI Basic Green 1 and other CI basic dyes CI Active Yellow 2, 76, 116; CI Active Orange 16; CI reactive dyes such as CI Reactive Red 36 CI Media Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Media Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Media Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Media Purple 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Media Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI mordant green dyes include 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, and 53. CI vat green 1 and other CI vat dyes, etc.

[0080] As pigments, for example, pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists) can be cited. The following pigments can be exemplified as such.

[0081] Green pigments: CI pigments green 7, 36, 58, 59, 62, 63, etc. Yellow pigments: CI pigment yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231, 233, etc. Orange pigments: CI pigments orange 13, 31, 34, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc. Red pigments: CI pigment red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 269, 272, etc. Blue pigments: CI pigment blue 15, 15:3, 15:4, 15:6, 16, 60, etc. Purple pigments: CI pigments purple 1, 19, 23, 29, 32, 36, 38, etc. Black pigments: CI Pigment Black 1, 7, 31, 32, etc. These pigments can be used with one or more pigments for each color, or a combination of pigments of different colors can be used.

[0082] The colorant (A2) is preferably one or more pigments, more preferably two or more pigments, and even more preferably a combination of two or more pigments selected from the group consisting of orange pigment, purple pigment, blue pigment and red pigment.

[0083] Pigments can be treated with rosin as needed; surface treatments can be performed using pigment derivatives with introduced acidic or basic groups; grafting treatments can be performed on the pigment surface using polymeric compounds; micronization treatments can be performed using sulfuric acid micronization methods; washing treatments can be performed using organic solvents, water, etc., to remove impurities; and ion exchange treatments can be performed to remove ionic impurities. The particle size of the pigment is preferably approximately uniform. By dispersing the pigment with a pigment dispersant, a pigment dispersion (coloring resin composition) that is uniformly dispersed in a pigment dispersant solution can be prepared. Pigments can be dispersed individually or in combination.

[0084] Examples of pigment dispersants include silicone-based, fluorinated, ester-based, cationic, anionic, nonionic, amphoteric, polyester-based, polyamine-based, and acrylic surfactants. Examples of surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, and polyethyleneimines. Commercially available surfactants include, for example, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), SOLSPERSE (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by BASF Japan Co., Ltd.), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), and Disperbyk (manufactured by BYK-Chemie Co., Ltd.).

[0085] When using a pigment dispersant, its amount is preferably 10 to 200 parts by weight of the pigment, more preferably 15 to 180 parts by weight, and even more preferably 20 to 160 parts by weight of the pigment. If the amount of pigment dispersant used is within the above range, when using two or more pigments, there is a tendency to obtain a pigment dispersion with a more uniform dispersion state.

[0086] The content of colorant (A2), based on the total amount of colorant (A), is preferably 0-90% by mass, more preferably 0-70% by mass, even more preferably 0-50% by mass, and particularly preferably 0-30% by mass. In the case where colorant (A1) is used as a toning agent for blue in the coloring resin composition, in one embodiment, the content of colorant (A2) may be 55-90% by mass or 65-80% by mass, based on the total amount of colorant (A).

[0087] The content of colorant (A) is 1% by mass or more, based on the total amount of solid components in the coloring resin composition. The content of colorant (A) is preferably 3% by mass or more, more preferably 5% by mass or more, further preferably 7% by mass or more, preferably 50% by mass or less, more preferably 40% by mass or less, and further preferably 30% by mass or less. If the content of colorant (A) is within the above range, it tends to be easier to obtain the desired spectroscopic and color concentration. It should be noted that, in this specification, "total amount of solid components in the coloring resin composition" refers to the total amount of components obtained after removing the solvent from the coloring resin composition. The total amount of solid components in the coloring resin composition and the content of each component relative to it can be determined by known analytical methods such as liquid chromatography and gas chromatography.

[0088] <Resin (B)> The coloring resin composition of this embodiment contains resin (B). Resin (B) is preferably an alkali-soluble resin. Examples of alkali-soluble resins include resins [K1] to [K6].

[0089] • Resin [K1]: A copolymer having structural units of at least one (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and structural units of monomers (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an olefinic unsaturated bond. • Resin [K2]: A copolymer having structural units from (a), structural units from (b), and structural units from monomer (c) that can copolymerize with (a) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)"). • Resin [K3]: A copolymer having structural units from (a) and structural units from (c). • Resin [K4]: A copolymer having a structural unit formed by adding (b) to a structural unit from (a), and a structural unit from (c). • Resin [K5]: A copolymer having a structural unit formed by adding (a) to a structural unit from (b), and a structural unit from (c). • Resin [K5']: A copolymer having a structural unit formed by adding (b) to a structural unit from (a) and a structural unit from (c); • Resin [K6]: A copolymer having a structural unit formed by adding (a) to a structural unit from (b) and further adding a carboxylic anhydride, and a structural unit from (c). As for (a), specifically, for example: Unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, ortho-, meta-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, zeaxanthin, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid. Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, etc., are bicyclic unsaturated compounds containing carboxyl groups; Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxylic acid bicyclic [2.2.1]hept-2-ene anhydride and other unsaturated dicarboxylic acid anhydrides; Unsaturated mono[(meth)acryloyloxyethyl] esters of polycarboxylic acids with two or more members, such as succinate mono[2-(meth)acryloyloxyethyl] ester and phthalate mono[2-(meth)acryloyloxyethyl] ester; Unsaturated acrylates such as α-(hydroxymethyl)acrylic acid and carboxyl groups in the same molecule.

[0090] Among them, considering both the copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions, (a) is preferably acrylic acid, methacrylic acid, or maleic anhydride.

[0091] (b) can be a polymeric compound having, for example, a cyclic ether structure having 2 to 4 carbon atoms (e.g., selected from at least one of the groups consisting of ethylene oxide ring, oxobutane ring, and tetrahydrofuran ring) and an olefinic unsaturated bond. (b) Preferably, it is a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0092] As (b), examples include monomers having epoxy ethyl and olefinic unsaturated bonds (b1) (hereinafter sometimes referred to as "(b1)"), monomers having oxocyclobutyl and olefinic unsaturated bonds (b2) (hereinafter sometimes referred to as "(b2)"), monomers having tetrahydrofuranyl and olefinic unsaturated bonds (b3) (hereinafter sometimes referred to as "(b3)"), etc.

[0093] As (b1), for example, examples include monomers (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which aliphatic unsaturated hydrocarbons are epoxidized in a straight or branched manner, and monomers (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which alicyclic unsaturated hydrocarbons are epoxidized.

[0094] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methylo-vinylbenzyl glycidyl ether, α-methylm-vinylbenzyl glycidyl ether, α-methylp-vinylbenzyl glycidyl ether, and 2,3-bis(glycidyloxymethyl) Styrene, 2,4-bis(glycidoxymethyl)styrene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tris(glycidoxymethyl)styrene, 2,3,5-tris(glycidoxymethyl)styrene, 2,3,6-tris(glycidoxymethyl)styrene, 3,4,5-tris(glycidoxymethyl)styrene, 2,4,6-tris(glycidoxymethyl)styrene, etc.

[0095] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000 (manufactured by Daicel Co., Ltd.)), 3,4-epoxycyclohexyl methyl methacrylate (e.g., Cyclomer A400 (manufactured by Daicel Co., Ltd.)), 3,4-epoxycyclohexyl methyl methacrylate (e.g., Cyclomer M100 (manufactured by Daicel Co., Ltd.)), and 3,4-epoxytricyclo(meth)acrylate [5.2.1.0]. 2,6 Decyl ester ((meth)acrylate 3,4-epoxytricyclo[5.2.1.0]) 2,6 ] Decane-8-yl ester, (meth)acrylate 3,4-epoxytricyclo[5.2.1.0] 2,6 [Decane-9-yl ester, etc.], (meth)acrylate 3,4-epoxytricyclic [5.2.1.0] 2,6 Decyloxyethyl ester, etc.

[0096] (b2) More preferably, it is a monomer having an oxetyl group and a (meth)acryloyloxy group. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc.

[0097] (b3) More preferably, it is a monomer having a tetrahydrofuran group and a (meth)acryloyloxy group. Examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150 (manufactured by Osaka Organic Chemicals Co., Ltd.)) and tetrahydrofurfuryl methacrylate.

[0098] From the perspective of further improving the reliability of the obtained color filter in terms of lightfastness, heat resistance, and chemical resistance, (b) is preferably (b1). Furthermore, from the perspective of excellent storage stability of the coloring resin composition and the coloring curable resin composition, (b) is more preferably (b1-2).

[0099] As for (c), for example, the following can be cited: 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(meth)acrylate [5.2.1.0] 2,6 ] Decane-8-yl ester (commonly known in this technical field as "(meth)acrylate dicyclopentyl ester". Also sometimes referred to as "(meth)acrylate tricyclodecyl ester"), (meth)acrylate tricyclo[5.2.1.0] 2,6 Decen-8-yl ester (commonly referred to as "(meth)acrylate dicyclopentenyl ester"), (meth)acrylate dicyclopentyloxyethyl ester, (meth)acrylate isobornyl ester, (meth)acrylate adamantane ester, (meth)acrylate allyl ester, (meth)acrylate propargyl ester, (meth)acrylate phenyl ester, (meth)acrylate naphthyl ester, (meth)acrylate benzyl ester, and other (meth)acrylate esters; 2-Hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, and other methacrylates containing hydroxyl groups; Diethyl maleate, diethyl fumarate, diethyl itaconic acid, and other dicarboxylic acid diesters; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo [2.2.1]Hept-2-ene, 5,6-diethoxybicyclo[2.2.1]Hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]Hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]Hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]Hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]Hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]Hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]Hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]Hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]Hept-2-ene, etc., are bicyclic unsaturated compounds; Dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimide-3-maleimide benzoate, N-succinimide-4-maleimide butyrate, N-succinimide-6-maleimide hexanoate, N-succinimide-3-maleimide propionate, and N-(9-acridyl)maleimide; Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.

[0100] Among them, considering copolymerization reactivity, lightfastness and heat resistance, (c) is preferably styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide or bicyclo[2.2.1]hept-2-ene.

[0101] In resin [K1], the preferred ratio of structural units from each of the various structural units constituting resin [K1] is: Structural units from (a): 2 to 60 mol% Structural units from (b): 40 to 98 mol%, More preferably: Structural units from (a): 10 to 50 mol% Structural units from (b): 50 to 90 mol%.

[0102] When the ratio of the structural units of the resin [K1] is within the above range, the storage stability of the colored resin composition and the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter tend to be excellent.

[0103] The resin [K1] can be produced, for example, according to the methods described in the reference "Experimental Methods of Polymer Synthesis" (実験法 高分子合成) (written by Takayuki Otsu, published by Kagaku Dojin Publishing Co., Ltd., 1st edition, 1st printing, issued on March 1, 1972) and the cited references described in this literature.

[0104] Specifically, the following method can be cited: A predetermined amount of (a), (b), a polymerization initiator, a solvent, etc. are added to a reaction vessel, and oxygen is replaced with nitrogen, for example, to create a deoxygenated atmosphere, and heating and heat preservation are carried out while stirring. It should be noted that the polymerization initiator and solvent used here are not particularly limited, and substances commonly used in this field can be used. For example, as the polymerization initiator, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.), organic peroxides (benzoyl peroxide, etc.) can be cited. The solvent only needs to be a solvent that dissolves each monomer. For example, the solvents exemplified in the solvent (E) described later can be used.

[0105] It should be noted that the obtained copolymer can be directly used as the reaction solution, or a concentrated or diluted solution can be used. In addition, the obtained copolymer can also be a substance taken out in the form of a solid (powder) by methods such as reprecipitation. In particular, by using the solvent (E) described later as the solvent during this polymerization, the reaction solution can be used for the preparation of the colored resin composition and the colored curable resin composition, so the manufacturing process of the colored resin composition and the colored curable resin composition in this embodiment can be simplified.

[0106] In the resin [K2], among all the structural units constituting the resin [K2], the ratio of the structural units from each component is preferably: Structural units from (a): 2 to 45 mol% Structural units from (b): 2 to 95 mol% Structural units from (c): 1 to 65 mol%, More preferably: Structural units from (a): 5~40 mol% Structural units from (b): 5~80 mol% Structural units from (c): 5~60 moles.

[0107] If the ratio of the structural units of resin [K2] is within the above range, the coloring resin composition and the color curing resin composition tend to have excellent storage stability, developability when forming color patterns, and solvent resistance, light resistance, heat resistance and mechanical strength of the obtained color filter.

[0108] Resin [K2] can be manufactured, for example, in the same manner as the method described for manufacturing resin [K1].

[0109] In resin [K3], the preferred ratio of structural units from each of the various structural units constituting resin [K3] is: Structural units from (a): 2~60 mol% Structural units from (c): 40~98 mol%. More preferably: Structural units from (a): 10~50 mol% Structural units from (c): 50~90 moles.

[0110] Resin [K3] can be manufactured, for example, in the same manner as the method described for manufacturing resin [K1].

[0111] The resin [K4] can be manufactured by obtaining a copolymer of (a) and (c) by adding a cyclic ether having 2 to 4 carbon atoms in (b) to a carboxylic acid and / or carboxylic anhydride in (a).

[0112] First, the copolymers of (a) and (c) are manufactured in the same manner as described in the method for manufacturing resin [K1]. In this case, the ratio of the structural units from each is preferably the same as the ratio exemplified in resin [K3].

[0113] Next, the cyclic ether having 2 to 4 carbon atoms in (b) is reacted with the carboxylic acid and / or carboxylic anhydride from (a) in the copolymer described above. After producing the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), the reaction catalyst of the carboxylic acid or carboxylic anhydride with the cyclic ether (e.g., tris(dimethylaminomethyl)phenol) and the polymerization inhibitor (e.g., hydroquinone) are added to the flask, and the reaction is carried out, for example, at 60 to 130°C for 1 to 10 hours, thereby producing resin [K4].

[0114] Compared to 100 moles of (a), the amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles. By setting it within this range, there is a tendency to improve the balance of the storage stability of the coloring resin composition and the coloring curable resin composition, the developability when forming a pattern, and the solvent resistance, light resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern. Considering the high reactivity of cyclic ethers and the fact that unreacted (b) is less likely to remain, the (b) used in resin [K4] is preferably (b1), more preferably (b1-1).

[0115] The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to the total mass of 100 parts by mass of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to the total mass of 100 parts by mass of (a), (b), and (c).

[0116] The reaction conditions, such as the charging method, reaction temperature, and time, can be appropriately adjusted taking into account the manufacturing equipment and the heat generated by polymerization.

[0117] Regarding resin [K5], as a first stage, copolymers of (b) and (c) are obtained in the same manner as resin [K1] described above. Similarly, regarding the obtained copolymer, the solution after the reaction can be used directly, or a concentrated or diluted solution can be used. Alternatively, the obtained copolymer can be a substance extracted in solid (powder) form through methods such as reprecipitation.

[0118] The preferred ratios of structural units from (b) and (c) are respectively, relative to the total number of moles of all structural units constituting the copolymer described above. Structural units from (b): 5~95 mol% Structural units from (c): 5~95 mol%. More preferably: Structural units from (b): 10~90 mol% Structural units from (c): 10~90 moles.

[0119] Furthermore, under the same conditions as the manufacturing method of resin [K4], the carboxylic acid or carboxylic anhydride contained in (a) is reacted with the cyclic ether from (b) contained in the copolymer of (b) and (c), thereby obtaining resin [K5].

[0120] The amount of (a) used in reaction with the copolymer described above is preferably 5 to 80 moles relative to 100 moles of (b). Considering the high reactivity of cyclic ethers and the low likelihood of unreacted (b) residue, the (b) used in resin [K5] is preferably (b1), and more preferably (b1-1).

[0121] In resin [K5'], the preferred ratio of structural units from each of the structural units constituting resin [K5'] is: Structural units from (a) (unadded to (b)): 0~30 mol% Structural units formed by adding (b) to structural units from (a): 5~95 mol% Structural units from (c): 5~95 mol%. More preferably: Structural units from (a) (unadded to (b)): 0~10 mol% Structural units formed by adding (b) to structural units from (a): 15~90 mol% Structural units from (c): 10~85 mol%. A further preferred option is: Structural units from (a) (unadded to (b)): 0-5 mol% Structural units formed by adding (b) to structural units from (a): 20~80 mol% Structural units from (c): 20-80 mol%.

[0122] In all the structural units constituting resin [K5'], the total of the structural units from (a) (without addition (b)), the structural units formed by adding (b) to the structural units from (a), and the structural units from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0123] As the structural unit from (a) (without addition (b)), it is preferably a structural unit from an unsaturated monocarboxylic acid such as (meth)acrylic acid. As the structural unit formed by adding (b) to the structural unit from (a), it is preferably a structural unit formed by adding a monomer (b1-1) having a structure in which a straight-chain or branched aliphatic unsaturated hydrocarbon is epoxidized to a structural unit from an unsaturated monocarboxylic acid such as (meth)acrylic acid. As the structural unit from (c), it is preferably one or more selected from (meth)acrylic esters having a straight-chain or branched aliphatic saturated hydrocarbon groups and (meth)acrylic esters having cyclic saturated hydrocarbon groups, more preferably two or more.

[0124] Regarding resin [K5'], the manufacturing method of resin [K4] described above can be used, and the amount used in (b) is greater than 80 moles and less than 100 moles relative to (a) 100 moles.

[0125] Resin [K6] is a resin obtained by further reacting carboxylic anhydride with resin [K5]. The carboxylic anhydride is reacted with a hydroxyl group (which is generated by the reaction of a cyclic ether with a carboxylic acid or carboxylic anhydride).

[0126] Examples of carboxylic anhydrides 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, and 5,6-dicarboxylic bicyclo[2.2.1]hept-2-ene anhydride. The amount of carboxylic anhydride used is preferably 0.5 to 1 mole relative to 1 mole of (a).

[0127] Specific examples of resin (B) include: methyl 3,4-epoxycyclohexyl methacrylate / (meth)acrylate copolymer, and 3,4-epoxytricyclic methacrylate [5.2.1.0]. 2,6 ] Decyl ester / (meth)acrylic acid copolymer and other resins [K1]; glycidyl methacrylate / benzyl methacrylate / (meth)acrylic acid copolymer, glycidyl methacrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxy tricyclic acrylic acid [5.2.1.0] 2,6 Decyl ester / (meth)acrylate / (meth)acrylate benzyl ester, 3,4-epoxytricyclic acrylic acid [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxy tricyclic acrylic acid [5.2.1.0] 2,6Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid 2-hydroxyethyl ester copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins formed by adding glycidyl methacrylate to benzyl acrylate / (meth)acrylic acid copolymer, resins formed by adding glycidyl methacrylate to tricyclodecyl acrylate / styrene / (meth)acrylic acid copolymer, and resins formed by adding glycidyl methacrylate to tricyclodecyl acrylate / styrene / (meth)acrylic acid copolymer. Resins such as resins formed by adding glycidyl methacrylate to a copolymer of cyclodecyl methacrylate / benzyl methacrylate / methacrylic acid [K4]; resins formed by reacting a copolymer of tricyclodecyl methacrylate / glycidyl methacrylate with (meth)acrylic acid; resins formed by reacting a copolymer of tricyclodecyl methacrylate / styrene / glycidyl methacrylate with (meth)acrylic acid; resins such as resins formed by reacting a copolymer of tricyclodecyl methacrylate / glycidyl methacrylate with (meth)acrylic acid; and resins formed by further reacting the resin with tetrahydrophthalic anhydride [K6].

[0128] Resin (B) is preferably a copolymer comprising at least one structural unit selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit having a cyclic ether structure with 2 to 4 carbon atoms and an olefinic unsaturated bond, more preferably resin [K1] or resin [K2], and even more preferably resin [K2].

[0129] The weight-average molecular weight of resin (B), converted from polystyrene, is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. If the weight-average molecular weight is within the above range, the following tendencies exist: the hardness of the color filter is increased, the residual film rate is high, the unexposed portion has good solubility in the developer, and the resolution of the colored pattern is improved.

[0130] 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.

[0131] The acid value of resin (B), converted from solid content, is preferably 10 to 170 mg-KOH / g, more preferably 20 to 150 mg-KOH / g, and even more preferably 30 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.

[0132] Based on the total amount of solid components in the coloring resin composition, the content of resin (B) is preferably 0.1 to 40% by mass, more preferably 1 to 30% by mass, and even more preferably 2 to 20% by mass. If the content of resin (B) is within the above range, there is a tendency to form a coloring pattern and to improve the resolution and residual film rate of the coloring pattern.

[0133] Solvent (C) The solvent (C) is not particularly limited and can be any solvent commonly used in this field. 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.

[0134] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0135] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether, and methyl anisole.

[0136] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 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-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, and diethylene glycol monobutyl ether acetate.

[0137] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0138] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol.

[0139] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0140] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0141] Among them, solvent (C) is preferably at least one selected from the group consisting of ether ester solvents and ether solvents, more preferably propylene glycol monomethyl ether acetate or diethylene glycol ethyl methyl ether.

[0142] Based on the total amount of the coloring resin composition, the solvent (C) content is preferably 70-95% by mass, more preferably 75-92% by mass. In other words, based on the total amount of the coloring resin composition, the solid component content of the coloring resin composition is preferably 5-30% by mass, more preferably 8-25% by mass. If the solvent (C) content is within the above range, the flatness during coating becomes good, the color concentration is less likely to be insufficient when forming a color filter, and therefore there is a tendency for the display properties to become better.

[0143] When using ether ester solvents, the content of ether ester solvents is preferably 10 to 100% by mass, more preferably 15 to 90% by mass, and even more preferably 17 to 80% by mass, based on the total amount of solvent.

[0144] When using an ether solvent, the content of the ether solvent is preferably 20 to 90% by mass, more preferably 30 to 85% by mass, and even more preferably 40 to 80% by mass, based on the total amount of solvent.

[0145] <Other Ingredients> The coloring resin composition of this embodiment may contain additives known in the art, such as dispersants, ultraviolet absorbers, fillers, other polymers, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as needed.

[0146] The coloring resin composition of this embodiment can be prepared, for example, by mixing a colorant (A), a resin (B), a solvent (C), and other components as needed. Preferably, the coloring resin composition is filtered using a filter with a pore size of approximately 0.01 to 10 μm after mixing the components.

[0147] The coloring resin composition of this embodiment can be suitably used in the preparation of coloring curable resin compositions.

[0148] [Coloring and Curing Resin Composition] The coloring and curing resin composition of this embodiment contains a colorant (A), a resin (B), a polymerizable compound (hereinafter sometimes referred to as "polymerizable compound (D)"), and a polymerization initiator (hereinafter sometimes referred to as "polymerization initiator (E)"). The coloring and curing resin composition of this embodiment may also contain a solvent (C), a leveling agent (hereinafter sometimes referred to as "leveling agent (F)"), other components, etc.

[0149] The colorant (A), resin (B), solvent (C), and other components in the coloring curable resin composition are the same as those in the coloring resin composition. Therefore, repeated descriptions are omitted here.

[0150] The content of colorant (A) is 0.1% by mass or more, based on the total amount of solid components in the color-curing resin composition. The content of colorant (A) is preferably 1% by mass or more, more preferably 2% by mass or more, further preferably 3% by mass or more, preferably 40% by mass or less, more preferably 30% by mass or less, and further preferably 20% by mass or less. If the content of colorant (A) is within the above range, it tends to be easier to obtain the desired spectroscopic and color concentration. It should be noted that, in this specification, the term "total amount of solid components in the color-curing resin composition" refers to the total amount of components obtained after removing the solvent from the color-curing resin composition. The total amount of solid components in the color-curing resin composition and the content of each component relative to it can be determined by known analytical methods such as liquid chromatography and gas chromatography.

[0151] Based on the total amount of solid components in the coloring curable resin composition, the content of resin (B) is preferably 1 to 40% by mass, more preferably 3 to 30% by mass, and even more preferably 5 to 20% by mass. If the content of resin (B) is within the above range, there is a tendency to form a coloring pattern and to improve the resolution and residual film rate of the coloring pattern.

[0152] Based on the total amount of the color-curing resin composition, the solvent (C) content is preferably 70-95% by mass, more preferably 75-92% by mass. In other words, based on the total amount of the color-curing resin composition, the solid component content of the color-curing resin composition is preferably 5-30% by mass, more preferably 8-25% by mass. If the solvent (C) content is within the above range, the flatness during coating becomes good, the color concentration is less likely to be insufficient when forming a color filter, and therefore there is a tendency for the display characteristics to become better.

[0153] <Polymerizing Compounds (D)> The coloring and curing resin composition of this embodiment contains a polymerizable compound (D) and a polymerization initiator (E). The polymerizable compound (D) is a compound capable of polymerization using active free radicals and / or acids generated by the polymerization initiator (E). Examples of polymerizable compounds (D) include compounds with polymerizable olefinic unsaturated bonds. The polymerizable compound (D) is preferably a (meth)acrylate compound.

[0154] The polymerizable compound (D) is preferably a polymerizable compound having three or more olefinic unsaturated bonds. Examples of such polymerizable compounds include, for instance, trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylates (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylates (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylates (e.g., tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylates (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tri(2-(meth)acryloyloxyethyl)isocyanurate, ethylene oxide modified pentaerythritol poly(meth)acrylates (e.g., ethylene oxide modified pentaerythritol tri(meth)acrylate, ethylene oxide modified pentaerythritol tetra(meth)acrylate), and ethylene oxide modified... Dipentaerythritol poly(meth)acrylates (e.g., ethylene oxide modified dipentaerythritol penta(meth)acrylate, ethylene oxide modified dipentaerythritol hexa(meth)acrylate), propylene oxide modified pentaerythritol poly(meth)acrylates (e.g., propylene oxide modified pentaerythritol tri(meth)acrylate, propylene oxide modified pentaerythritol tetra(meth)acrylate), propylene oxide modified dipentaerythritol poly(meth)acrylates (e.g., propylene oxide modified dipentaerythritol poly(meth)acrylates) Pentaerythritol pentamethacrylate, propylene oxide modified pentaerythritol hexamethacrylate, caprolactone modified pentaerythritol polymethacrylate (e.g., caprolactone modified pentaerythritol trimethacrylate, caprolactone modified pentaerythritol tetramethacrylate), caprolactone modified pentaerythritol polymethacrylate (e.g., caprolactone modified pentaerythritol pentamethacrylate, caprolactone modified pentaerythritol hexamethacrylate), etc. Among them, the polymeric compound (D) is preferably trimethylolpropane tri(meth)acrylate, dipentaerythritol poly(meth)acrylate (a mixture of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate), or ethylene oxide modified dipentaerythritol poly(meth)acrylate (a mixture of ethylene oxide modified dipentaerythritol penta(meth)acrylate and ethylene oxide modified dipentaerythritol hexa(meth)acrylate).

[0155] The molecular weight or weight-average molecular weight of the polymeric compound (D) is preferably 150 to 2900, more preferably 250 to 1500.

[0156] Based on the total amount of solid components in the coloring and curing resin composition, the content of the polymeric compound (D) is preferably 1 to 50% by mass, more preferably 2 to 40% by mass, and even more preferably 3 to 30% by mass. If the content of the polymeric compound (D) is within the above range, there is a tendency to improve the residual film rate when forming the coloring pattern and the chemical resistance of the color filter.

[0157] <Polymerization Initiator (E)> The polymerization initiator (E) is any compound that can generate active free radicals, acids, etc., under the action of light or heat and is capable of initiating polymerization; there are no particular limitations, and known polymerization initiators can be used. Examples of polymerization initiators that generate active free radicals include O-acyl oxime compounds, alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, and biimidazole compounds.

[0158] O-acyl oxime compounds are compounds having a partial structure represented by formula (e1). Below, Indicates a connection key.

[0159] Examples of O-acyl oxime compounds include, for instance, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, and N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3, 3-Dimethyl-2,4-dioxanepentylmethyloxy)benzoyl]-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, etc. As O-acyl oxime compounds, commercially available products such as Irgacure (registered trademark, hereinafter the same) OXE01 (N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine), Irgacure OXE02 (N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine) (all manufactured by BASF), and N-1919 (manufactured by ADEKA Co., Ltd.) can also be used.

[0160] Among them, the O-acyl oxime compounds are preferably selected from N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, and... At least one of the following groups is selected from N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, more preferably N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, or N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine. Using such O-acyl oxime compounds tends to yield color filters with high brightness.

[0161] Alkyl phenyl ketone compounds are compounds having a partial structure represented by formula (e2) or a partial structure represented by formula (e3). In these partial structures, the benzene ring may have substituents.

[0162] Examples of compounds having a partial structure represented by formula (e2) include 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one. Commercially available products such as Irgacure 369, 907, and 379 (manufactured by BASF) can be used as compounds having a partial structure represented by formula (e2).

[0163] Examples of compounds having a partial structure represented by formula (e3) include, for example, oligomers of 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, benzoyladimethyl ketal, etc.

[0164] From the perspective of sensitivity, alkyl phenyl ketone compounds are preferably compounds having a partial structure represented by formula (e2).

[0165] Examples of triazine compounds include, for instance, 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-piperyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ [2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0166] Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure 819 (manufactured by BASF) can also be used as acylphosphine oxide compounds.

[0167] Examples of biimidazole compounds include, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Application Publication Nos. 6-75372 and 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 (e.g., see Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with an alkoxycarbonyl group (e.g., see Japanese Patent Application Publication No. 7-10913, etc.).

[0168] In addition, examples of polymerization initiators (E) include benzoin compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as methyl benzoyl peroxide, 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-phenanthroquinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzoin, methyl phenylglyoxylate, and titanium decene compounds. These are preferably used in combination with polymerization initiators (E1) (especially amines) described later.

[0169] Examples of polymerization initiators that generate acids include, for example, onion salts such as 4-hydroxyphenyl dimethyl sulfonium p-toluenesulfonate, 4-hydroxyphenyl dimethyl sulfonium hexafluoroantimonate, 4-acetoxyphenyl dimethyl sulfonium p-toluenesulfonate, 4-acetoxyphenyl methyl benzyl sulfonium hexafluoroantimonate, triphenyl sulfonium p-toluenesulfonate, triphenyl sulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyl toluenesulfonate, and benzoin toluenesulfonate.

[0170] The polymerization initiator (E) is preferably a polymerization initiator comprising at least one selected from the group consisting of O-acyl oxime compounds, alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds and bimidazole compounds, and more preferably a polymerization initiator comprising an O-acyl oxime compound.

[0171] The content of polymerization initiator (E) 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 (D), and more preferably 1 to 20 parts by mass. If the content of polymerization initiator (E) is within the above range, there is a tendency to achieve high sensitivity and shorten the exposure time, and therefore an increase in the productivity of the color filter can be expected.

[0172] <Polymerization Initiator (E1)> Polymerization initiator (E1) is a compound or sensitizer used to promote the polymerization of polymerizable compounds. In the case of a coloring and curing resin composition containing a polymerization initiator (E1), it is usually used in combination with a polymerization initiator (E).

[0173] Examples of polymerization initiators (E1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0174] Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as benzophenone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used as amine compounds. Among these, 4,4'-bis(diethylamino)benzophenone is preferred.

[0175] Examples of alkoxyanthracene compounds 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.

[0176] Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0177] Examples of carboxylic acid compounds include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0178] When using these polymerization initiators (E1), the content 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 (D). If the amount of polymerization initiator (E1) is within this range, there is a tendency to be able to form colored patterns with higher sensitivity and to increase the productivity of color filters.

[0179] Leveling agent (F) Examples of leveling agents (F) include silicone surfactants, fluorinated surfactants, and silicone surfactants containing fluorine atoms. They may have polymerizable groups on their side chains.

[0180] Examples of organosilicon surfactants include surfactants that have intramolecular siloxane bonds. Specifically, 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 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 Japan Contract Co., Ltd.).

[0181] Fluorinated surfactants include those with intramolecular fluorocarbon chains. Specifically, examples include FLOURAD (registered trademark) FC430, FLOURAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFACE (registered trademark) F142D, MEGAFACE F171, MEGAFACE F172, MEGAFACE F173, MEGAFACE F177, MEGAFACE F183, MEGAFACE F554, MEGAFACE R30, MEGAFACE 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, and SURFLON... SC105 (manufactured by AGC Corporation (formerly Asahi Glass Corporation)) and E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.), etc.

[0182] Organosilicon surfactants containing fluorine atoms include surfactants with siloxane bonds and fluorocarbon chains within the molecule. Specifically, examples include MEGAFACE (registered trademark) R08, MEGAFACE BL20, MEGAFACE F475, MEGAFACE F477, and MEGAFACE F443 (manufactured by DIC Corporation).

[0183] Based on the total amount of the color-curing resin composition, the leveling agent (F) content is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, and even more preferably 0.01 to 0.05% by mass. If the leveling agent (F) content is within the above range, the flatness of the color filter can be well achieved.

[0184] The coloring-curing resin composition of this embodiment can be prepared, for example, by mixing a colorant (A), a resin (B), a solvent (C), a polymerizable compound (D), a polymerization initiator (E), and, as needed, a polymerization initiation aid (E1), a leveling agent (F), and other components. For the coloring-curing resin composition, it is preferable to filter the mixture using a filter with a pore size of approximately 0.01 to 10 μm. Alternatively, the above-described coloring resin composition can be prepared in advance and used in the preparation of the coloring-curing resin composition.

[0185] The coloring and curing resin composition of this embodiment can be suitably used for the formation of color filters.

[0186] Color filters and their manufacturing methods Examples of methods for manufacturing colored patterns from the color-curable resin composition of this embodiment include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. Photolithography involves coating a color-curable resin composition onto a substrate, drying it to form a colored coating film, exposing the colored coating film through a photomask, and developing it. In photolithography, by not using a photomask during exposure and / or not developing, a color-cured coating film, which is a cured product of the colored coating film, can be formed. It should be noted that, regarding the color-cured coating film, it is also possible to form it by heating the colored coating film without using photolithography. The colored pattern (patterned color-cured coating film) or color-cured coating film thus formed serves as the color filter of this embodiment.

[0187] The film thickness of the fabricated color filter is not particularly limited and can be adjusted appropriately according to the purpose and application. For example, the film thickness of the color filter can be 0.1~30μm, preferably 0.1~20μm, and more preferably 0.5~6μm.

[0188] Examples of substrates include glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass obtained by coating the surface with silica; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon substrates; and substrates obtained by forming thin films of aluminum, silver, or silver / copper / palladium alloys on these substrates. Other components such as color filters (colored patterns or colored and cured coatings), resin films, transistors, and circuits can also be formed on these substrates.

[0189] The formation of individual pixels using photolithography can be carried out using known or commonly used devices and conditions. For example, individual pixels using photolithography can be fabricated in the following manner.

[0190] First, a coloring curable resin composition is coated onto a substrate, and volatile components such as solvents are removed by heating and drying (pre-baking) and / or vacuum drying, thereby obtaining a smooth coloring coating film.

[0191] Examples of coating methods include spin coating, slot coating, and a combination of slot and spin coating. When heat drying is performed, the preferred temperature is 30–120°C, more preferably 50–110°C. The preferred heating time is 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When vacuum drying is performed, it is preferably carried out under a pressure of 50–150 Pa and a temperature range of 20–25°C.

[0192] There is no particular limitation on the thickness of the colored coating; it can be appropriately selected according to the thickness of the target color filter.

[0193] Next, the colored coating is exposed through a photomask used to form the target colored pattern. The pattern obtained using the photomask is not particularly limited; a pattern appropriate for the intended use can be used.

[0194] The light source used in the exposure is preferably a light source that produces light with a wavelength of 250-450 nm. For example, the light source used in the exposure can be a light source that uses a filter to cut off light with wavelengths less than 350 nm, or a light source that selectively extracts light with bandpass filters that extract wavelengths around 436 nm, 408 nm, and 365 nm. Specific examples of light sources used in the exposure include mercury lamps, light-emitting diodes (LEDs), metal halide lamps, and halogen lamps.

[0195] In the exposure process, in order to uniformly irradiate the entire exposure surface with parallel light and to accurately align the photomask with the substrate on which the colored coating is formed, it is preferable to use exposure equipment such as a mask alignment machine and a stepper.

[0196] A colored pattern is formed on a substrate by contacting the exposed colored coating (i.e., the colored cured coating) with a developing solution. During development, the unexposed portions of the colored cured coating dissolve in the developing solution and are removed. Examples of developing solutions include aqueous solutions (aqueous developing solutions) containing alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide. The concentration of the alkaline compounds in these aqueous developing solutions is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The developing solution may also contain a surfactant.

[0197] Examples of development methods include spin-dip immersion, dipping, and spraying. During development, the substrate can be tilted at any angle. Furthermore, after development, it is preferable to wash the resulting colored pattern with water.

[0198] In the obtained colored pattern, post-baking is preferred. The post-baking temperature is preferably 150~250℃, more preferably 160~235℃. The post-baking time is preferably 1~120 minutes, more preferably 10~60 minutes.

[0199] Without creating a pattern, the color-cured coating film, as a cured product of the color coating film, can also be formed, for example, by heating the color coating film after it has been formed from the resin composition without exposure. The heating conditions can be, for example, the same as those for post-baking.

[0200] [Display devices and solid-state cameras] The display device of this embodiment includes a color filter that serves as a colored pattern, a colored curing coating, etc. The solid-state imaging device of this embodiment includes a color filter that serves as a colored pattern, a colored curing coating, etc.

[0201] According to the color-curable resin composition of this embodiment, for example, a color filter can be manufactured. This color filter is useful as a film used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays; and in solid-state imaging devices such as CCDs and CMOS sensors.

[0202] Example The present invention will be described in more detail below with examples, but the present invention is not limited to the following examples. Of course, it can be implemented by appropriate modifications within the scope of the above-described spirit, and all such modifications are included within the technical scope of the present invention. It should be noted that, unless otherwise specified, "parts" in the following text refers to "parts by mass" and "%" refers to "% by mass".

[0203] In the following embodiments, "room temperature" refers to 18~24°C.

[0204] In the following examples, the structure of the compound was confirmed using a mass spectrometry apparatus (LC: Agilent 1200, MASS: Agilent LC / MSD6130).

[0205] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin, converted to polystyrene, were determined using the GPC method under the following conditions.

[0206] Device: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: Tetrahydrofuran Flow rate: 1.0 mL / min The concentration of solid components in the analytical sample was 0.001~0.01% by mass. Injection volume: 50μL Detector: RI Calibration standard materials: TSK polystyrene standards F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of weight-average molecular weight to number-average molecular weight (Mw / Mn) obtained above in the polystyrene conversion is used as the dispersity.

[0207] (Example 1-1) <Synthesis of the compound represented by formula (I-1) (colorant A-1)> 1.00 parts of the compound represented by formula (1), 3.17 parts of 2,4,6-triphenylaniline (manufactured by Sigma-Aldrich Co., Ltd.), 0.67 parts of zinc chloride (manufactured by Wako Pure Chemical Industries Co., Ltd.), and 6.00 parts of sulfolane (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 250°C, and stirred for 7 hours. After cooling the reaction solution to room temperature, 12 parts of 1N hydrochloric acid were added as the residue after filtration to obtain the precipitate. The precipitate was washed successively with 24.0 parts of toluene, 12.0 parts of DMF, and 12.0 parts of ethyl acetate, and then dried to obtain 1.67 parts of the compound represented by formula (I-1) (colorant A-1). The yield was 69%.

[0208] Identification of the compound represented by formula (I-1) (colorant A-1) (Mass spectrometry) Ionization mode = ESI + m / z = [M + H] + 975.2 Accurate quality: 974.3 (Examples 1-2) <Synthesis of the compound represented by formula (I-5) (colorant A-2)> 3.00 parts of the compound represented by formula (1), 4.76 parts of 2,4,6-triphenylaniline (manufactured by Sigma-Aldrich Co., Ltd.), and 18.0 parts of sulfolane (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 120°C, and stirred for 4 hours. After cooling the reaction solution to room temperature, 36.0 parts of 1N hydrochloric acid were added as the residue after filtration to obtain the precipitate, which was further washed with 30.0 parts of toluene. The obtained residue was dried to obtain 5.10 parts of the compound represented by formula (2). Yield >99%.

[0209] 2.00 parts of the compound represented by formula (2), 2.76 parts of 3-aminobiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), and 12.0 parts of N-methylpyrrolidone (manufactured by FUJIFILM Wako Pure Chemical Corporation) were mixed at room temperature, heated to 170°C, and stirred for 5 hours. After cooling the reaction solution to room temperature, 424.0 parts of 1N hydrochloric acid were added as the residue after filtration to obtain the precipitate, which was further washed with 48.0 parts of 1N hydrochloric acid and 23.7 parts of N,N-dimethylformamide. The obtained residue was dried to obtain 1.29 parts of the compound represented by formula (I-5) (colorant A-2). The yield was 53.0%.

[0210] Identification of the compound represented by formula (I-5) (colorant A-2) (Mass spectrometry) Ionization mode = ESI + m / z = [M + H] + 823.2 Accurate quality: 822.3 (Examples 1-3) <Synthesis of the compound represented by formula (I-6) (colorant A-3)> By replacing 3-aminobiphenyl with 2-aminobiphenyl, and otherwise operating in the same manner as in Examples 1-2, the compound represented by formula (I-6) (colorant A-3) was obtained. The yield was 72.7%.

[0211] Identification of the compound represented by formula (I-6) (colorant A-3) (Mass spectrometry) Ionization mode = ESI + m / z = [M + H] + 823.2 Accurate quality: 822.3 (Comparative Example 1) <Synthesis of the compound (colorant a-1) represented by formula (3)> According to Japanese Patent Application Publication No. 2021-162854, the compound represented by synthetic formula (3) is (coloring agent a-1).

[0212] (Synthesis example 1) Synthesis of Resin B-1 A suitable amount of nitrogen was passed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere. 280 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 80°C while stirring. Then, using a dropping pump, 38 parts of acrylic acid and 3,4-epoxytricyclic acrylic acid [5.2.1.0] were added dropwise to the flask over approximately 5 hours. 2,6 ] Decane-8-yl ester and 3,4-epoxytricyclic acrylate [5.2.1.0] 2,6 A solution was prepared by dissolving 289 parts of a mixture of decane-9-yl esters (at a 1:1 ratio) in 125 parts of propylene glycol monomethyl ether acetate. Meanwhile, using a separate drop pump, a solution was added dropwise over approximately 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-1) solution with a solid content of 35.1%. The weight-average molecular weight (Mw) of the resulting copolymer (resin B-1) was 9.2 × 10⁻⁶. 3 The dispersion is 2.08, and the acid value based on solid content is 77 mg-KOH / g. The resulting copolymer has the following structural units.

[0213] (Synthesis example 2) Synthesis of Resin B-2 276.8 parts of propylene glycol monomethyl ether acetate (PGMEA) were added to a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube. The mixture was stirred while undergoing nitrogen purging, and the temperature was raised to 120°C. Next, 35.3 parts of tert-butyl peroxide (polymerization initiator) were added dropwise to a monomer mixture consisting of 92.4 parts of 2-ethylhexyl acrylate, 184.9 parts of glycidyl methacrylate, and 12.3 parts of dicyclopentyl methacrylate. This mixture was added dropwise to the flask over a period of 2 hours. After the addition was complete, the mixture was stirred at 120°C for 30 minutes to initiate a copolymerization reaction, synthesizing an addition copolymer. Then, the flask was purged with air, and 93.7 parts of acrylic acid, 1.5 parts of triphenylphosphine (catalyst), and 0.8 parts of p-hydroxyanisole (polymerization inhibitor) were added to the addition copolymer solution. The reaction was carried out at 110°C for 10 hours. During this process, the epoxy groups from glycidyl methacrylate reacted with acrylic acid, causing epoxy group cracking and introducing polymerizable unsaturated bonds into the side chains of the addition copolymer. Next, 24.2 parts of succinic anhydride were added to the reaction system, and the reaction was carried out at 110°C for 1 hour. The hydroxyl groups generated from the epoxy group cracking reacted with the succinic anhydride, introducing carboxyl groups into the side chains, yielding the copolymer (resin B-2). Finally, 383.3 parts of PGMEA were added to the reaction solution to obtain a copolymer (resin B-2) solution with a solid content of 40% by mass. The weight-average molecular weight of the resulting copolymer, converted to polystyrene, was 6.3 × 10⁻⁶. 3 The acid value, calculated based on the solid component, is 34 mg-KOH / g.

[0214] (Example 2-1) <Preparation of Coloring Resin Composition 1> 80.0 parts of the compound represented by formula (I-1) (colorant A-1), 29.1 parts of dispersant (BYK Corporation, BYKLPN-6919) (converted to solid content), 29.1 parts of resin B-1 obtained in Synthesis Example 1 (converted to solid content), 861.8 parts of propylene glycol monomethyl ether acetate, and 1500 parts of 0.2 mm zirconia beads were mixed and the mixture was shaken for 1 hour using a paint conditioner (LAU Corporation). Then, the zirconia beads were removed by filtration to obtain coloring resin composition 1.

[0215] (Example 2-2) <Preparation of Coloring Resin Composition 2> The compound (colorant A-1) represented by formula (I-1) was replaced with 80.0 parts of the compound (colorant A-3) represented by formula (I-6), and otherwise the same procedure was followed as in Example 2-1 to obtain coloring resin composition 2.

[0216] (Comparative Example 2-1) <Preparation of Coloring Resin Composition 3> The compound (colorant A-1) represented by formula (I-1) was replaced with 80.0 parts of the compound (colorant a-1) represented by formula (3), and otherwise the same procedure was followed as in Example 2-1 to obtain the colored resin composition 3.

[0217] (Example 3-1) <Preparation and Evaluation of Colored and Cured Coating 1> (1) Preparation of coloring and curing resin composition 1 The following components are mixed to obtain a coloring and curing resin composition 1.

[0218] • Coloring resin composition of Example 2-1: 1: 407.1 parts (Colorant (A): 32.6 parts of the compound represented by formula (I-1) (Colorant A-1) Resin (B): 11.8 parts of resin (B-1) (converted based on solid content) Solvent (E): 350.8 parts of propylene glycol monomethyl ether acetate Other ingredients: Dispersant (manufactured by BYK, BYKLPN-6919) 11.8 parts (converted based on solid component) • Resin (B): 51.8 parts of resin (B-2) obtained in Synthesis Example 2 (converted based on solid content) Solvent (C): 484.2 parts of propylene glycol monomethyl ether acetate • Polymerizable compound (D): Dipentaerythritol polyacrylate (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., trade name A-9550) 42.5 parts (converted based on solid content) • Polymerization initiator (E): N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd., trade name TR-PBG327) 9.0 parts • Leveling agent (F): 0.1 parts of polyether-modified silicone oil (manufactured by Toray Dow Corning Co., Ltd., trade name TORAY SILICONESH8400). (2) Preparation of coloring and curing coating 1 The obtained coloring and curing resin composition 1 was coated onto a 5 cm square glass substrate (Corning, Eagle 2000) using a spin coating method to obtain a coloring coating film 1. Then, the coloring coating film 1 was pre-baked at 100°C for 2 minutes and then baked in an oven at 230°C for 5 minutes to obtain the coloring and curing coating film 1.

[0219] (3) Lightfastness test - 1 An ultraviolet cutoff filter (Hoya Corporation, COLORED OPTICAL GLASS L38, a filter that blocks light below 380 nm) was applied to the obtained colored and cured coating 1 (colored and cured coating 1 before light irradiation). The coating was then irradiated with a xenon lamp for 67 hours in the atmosphere using a lightfastness testing machine (Toyo Seiki Corporation, SUNTEST CPS+), resulting in the colored and cured coating 1 after light irradiation. The absorbance at the maximum absorption wavelength of the colored and cured coating 1 before and after light irradiation was measured using a colorimeter (Olympus Corporation, OSP-SP-200), and the absorbance retention rate was calculated. Here, the absorbance retention rate is a value calculated using the following formula; a higher absorbance retention rate indicates better lightfastness. Furthermore, if the colored and cured coating has good lightfastness, it can be said that the color filter made from the same colored and cured resin composition also has excellent lightfastness. The results are shown in Table 1.

[0220] Absorbance retention rate (%) = (Absorbance at the maximum absorption wavelength of the color-cured coating after light irradiation) / (Absorbance at the maximum absorption wavelength of the color-cured coating before light irradiation) × 100 (4) Lightfastness test - 2 Using the above-described color-cured coating 1 before and after light irradiation, the change in maximum transmittance before and after light irradiation was measured. Here, the change in maximum transmittance before and after light irradiation refers to the largest of the transmittance changes (transmittance change before and after light irradiation (%) = transmittance before light irradiation (%) - transmittance after light irradiation (%)) at each wavelength in the range of 300–1400 nm. The smaller the change in maximum transmittance of the cured coating before and after light irradiation, the better its lightfastness. If the color-cured coating has good lightfastness, it can be said that the color filter made from the same color-curing resin composition also has excellent lightfastness. The results are shown in Table 1.

[0221] (Example 3-2) <Preparation and Evaluation of Colored and Cured Coating 2> The coloring resin composition 1 of Example 2-1 was replaced with 407.1 parts of the coloring resin composition 2 of Example 2-2. Otherwise, the coloring curable resin composition 2 was prepared in the same manner as in Example 3-1. Next, a coloring curable coating film 2 was prepared from the coloring curable resin composition 2 in the same manner as in Example 3-1, and a lightfastness test was performed. The results are shown in Table 1.

[0222] (Comparative Example 3-1) <Preparation and Evaluation of Colored Curing Coating 3> The coloring resin composition 1 of Example 2-1 (407.1 parts) was replaced with the coloring resin composition 3 of Comparative Example 2-1 (407.1 parts). Otherwise, the coloring curable resin composition 3 was prepared in the same manner as in Example 3-1. Next, a coloring curable coating film 3 was prepared from the coloring curable resin composition 3 in the same manner as in Example 3-1, and a lightfastness test was performed. The results are shown in Table 1. It should be noted that, for the coloring curable coating film 3, a lightfastness test-2 was not performed because the results of lightfastness test-1 were unsatisfactory.

[0223] [Table 1] As shown in Table 1, the color-cured coatings of Examples 3-1 and 3-2 containing the specified colorant (compound (I)) showed higher absorbance retention and smaller change in maximum transmittance before and after light irradiation compared to the color-cured coating of Comparative Example 3-1 which did not contain the specified colorant. These results confirm that the compounds of the present invention can be used to form color filters with excellent lightfastness; and that the color-curable resin compositions of the present invention can form color filters with excellent lightfastness.

Claims

1. The compound represented by formula (I), In formula (I), R 1 This represents a monovalent hydrocarbon group with 21 to 40 carbon atoms; R 3 This represents a monovalent hydrocarbon group with 6 to 40 carbon atoms; R 2 and R 4 Each can independently represent a monovalent saturated hydrocarbon group with 1 to 6 hydrogen atoms or carbon atoms; R 5 Indicates -OH, -SO3 - -SO3H, -SO3 - Z + -CO2H, -CO2 - Z + -CO2R 8 -SO3R 8 or -SO2NR 9 R 10 ; R 6 and R 7 Each can independently represent a monovalent saturated hydrocarbon group with 1 to 6 hydrogen atoms or carbon atoms; m represents an integer from 0 to 5; when m is greater than 2, multiple R... 5 They can be the same or different; 'a' represents an integer 0 or 1; X represents a halogen atom; Z + N represents + (R) 11 4. Na + or K + 4 Rs 11 They can be the same or different; R 8 It represents a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms, in which the hydrogen atoms can be replaced by halogen atoms; R 9 and R 10 Each of the above can independently represent a hydrogen atom or a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents, wherein the -CH2- group contained in the saturated hydrocarbon group may be replaced by -O-, -CO-, -NH- or -NR. 8 -;R 9 and R 10 They can bond with each other and form heterocycles with adjacent nitrogen atoms, consisting of 3- to 10-membered rings; R 11 It represents a hydrogen atom, a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms, or an aralkyl group with 7 to 10 carbon atoms.

2. A coloring resin composition, comprising a colorant and a resin, The colorant comprises the compound represented by formula (I) as described in claim 1.

3. A coloring and curing resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator. The colorant comprises the compound represented by formula (I) as described in claim 1.

4. A color filter formed from the color-curing resin composition of claim 3.

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

6. A solid-state imaging device comprising the color filter of claim 4.

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