Colored curable resin composition, color filter, display device, and solid-state imaging element

Abstract

The present invention addresses the problem of providing a colored curable resin composition capable of forming a color filter having improved solvent resistance. The present invention relates to a colored curable resin composition comprising a colorant, a resin, a polymerizable compound and a polymerization initiator, the polymerization initiator comprising a compound represented by formula (I). (In the formula, R1, R2, R3, R4 and R5 each independently represent an optionally substituted hydrocarbon group. And n represents an integer of 0 to 4. -CH2-contained in the hydrocarbon group may be substituted by-O-,-S-,-CO-, or-OCO-). # imgabs0 #

Description

Technical Field

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

[0002] Color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma display panels, and solid-state imaging devices such as CCDs and CMOS sensors are manufactured from colored curable resin compositions. It is known to use a specified polymerization initiator or the like in such colored curable resin compositions (Patent Document 1).

[0003] Prior Art Documents

[0004] Patent Documents

[0005] Patent Document 1: WO 2021 / 175855 Summary of the Invention

[0006] An object of the present invention is to provide a colored curable resin composition capable of forming a color filter with improved solvent resistance.

[0007] That is, the gist of the present invention is as follows.

[0008] [1] A colored curable resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator,

[0009] wherein the polymerization initiator contains a compound represented by formula (I).

[0010]

[0011] (In the formula, R 1 , R 2 , R 3 , R 4 , and R 5 each independently represent a hydrocarbon group which may have a substituent.

[0012] n represents any integer from 0 to 4.

[0013] In the above hydrocarbon group, -CH 2 - may be substituted with -O-, -S-, -CO-, or -OCO-.)

[0014] [2] The colored curable resin composition according to [1], wherein the resin is at least one selected from the following resins [K1] to [K6].

[0015] Resin [K1]; a copolymer having a structural unit derived from at least one monomer (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides and a structural unit derived from a monomer (b) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenic unsaturated bond;

[0016] Resin [K2]; a copolymer having a structural unit derived from the above (a), a structural unit derived from the above (b), and a structural unit derived from a monomer (c) copolymerizable with the above (a);

[0017] Resin [K3]; a copolymer having a structural unit derived from the above (a) and a structural unit derived from the above (c);

[0018] Resin [K4]; a copolymer having a structural unit obtained by adding the above (b) to a structural unit derived from the above (a) and a structural unit derived from the above (c);

[0019] Resin [K5]; a copolymer having a structural unit obtained by adding the above (a) to a structural unit derived from the above (b) and a structural unit derived from the above (c);

[0020] Resin [K5']; a copolymer having a structural unit obtained by adding the above (b) to a structural unit derived from the above (a) and a structural unit derived from the above (c);

[0021] Resin [K6]; a copolymer having a structural unit obtained by adding the above (a) to a structural unit derived from the above (b) and further adding a carboxylic anhydride and a structural unit derived from the above (c).

[0022] [3] The colored curable resin composition according to [2], wherein the above resin is resin [K1] and / or resin [K2].

[0023] [4] The colored curable resin composition according to [2], wherein the above resin is any one of resins [K2] to [K6], and is a resin containing at least one selected from (meth)acrylates having a linear or branched aliphatic unsaturated hydrocarbon group, (meth)acrylates having a cyclic unsaturated aliphatic hydrocarbon group, vinyl monomers having an unsaturated aliphatic hydrocarbon ring, vinyl monomers having an unsaturated heterocycle, and vinyl monomers having an aromatic ring as the above monomer (c).

[0024] [5] The colored curable resin composition according to [2], wherein the above resin is any one of resins [K4] to [K6].

[0025] [6] The colored curable resin composition according to [2], wherein the above resin has an ethylenic double bond, and the ethylenic double bond equivalent of the above resin is 100 to 2000 g / mol.

[0026] [7] The colored curable resin composition according to [2], wherein the resin is any one of resins [K2] to [K4], and contains (meth)acrylates having an aromatic ring as the monomer (c), and in 100 mol% of all structural units, the total of the structural units derived from (meth)acrylates having an aromatic ring and the structural units derived from the above (a) is 60 mol% or more.

[0027] [8] The colored curable resin composition according to [2], wherein the colorant contains a green pigment and a yellow pigment.

[0028] The above green pigment contains at least one selected from C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment Green 58, C.I. Pigment Green 59, C.I. Pigment Green 62, and C.I. Pigment Green 63.

[0029] The above yellow pigment contains at least one selected from C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 185, C.I. Pigment Yellow 231, and C.I. Pigment Yellow 233.

[0030] [9] The colored curable resin composition according to [2], wherein the colorant contains a red pigment and a yellow pigment.

[0031] The above red pigment contains at least one selected from C.I. Pigment Red 122, C.I. Pigment Red 177, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264, C.I. Pigment Red 269, C.I. Pigment Red 272, and C.I. Pigment Red 291.

[0032] The above yellow pigment contains at least one selected from C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 185, C.I. Pigment Yellow 231, and C.I. Pigment Yellow 233.

[0033]

[10] The colored curable resin composition according to [2], wherein the colorant contains a blue pigment and a purple pigment.

[0034] The above blue pigment contains at least one selected from C.I. Pigment Blue 15, 15:3, 15:4, 15:6, and 16.

[0035] The above purple pigment contains at least one selected from C.I. Pigment Violet 19, 23, and 29.

[0036]

[11] A color filter formed from the color-curable resin composition according to any one of [1] to

[10] .

[0037]

[12] A display device including the color filter described in

[11] .

[0038]

[13] A solid-state imaging device including the color filter described in

[11] .

[0039] According to the present invention, a color-curable resin composition capable of forming a color filter with improved solvent resistance can be provided. Detailed Description

[0040] The color-curable resin composition of the present invention contains a colorant (hereinafter, sometimes referred to as colorant (A)), a resin (hereinafter, sometimes referred to as resin (B)), a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D)).

[0041] The color-curable resin composition of the present invention may further contain a solvent (hereinafter, sometimes referred to as solvent (E)).

[0042] The color-curable resin composition of the present invention may further contain a polymerization initiator assistant (hereinafter, sometimes referred to as polymerization initiator assistant (D1)).

[0043] The color-curable resin composition of the present invention may further contain a thiol compound (hereinafter, sometimes referred to as thiol compound (T)).

[0044] The color-curable resin composition of the present invention may further contain a leveling agent (hereinafter, sometimes referred to as leveling agent (F)).

[0045] It should be noted that in this specification, the compounds exemplified as each component can be used alone or in combination of two or more without special mention.

[0046] <Colorant (A)>

[0047] As the colorant (A), a dye (A1) and a pigment (A2) can be cited, and the pigment (A2) is preferred. These can be used alone or in combination of two or more.

[0048] The dye (A1) is not particularly limited, and known dyes can be used. For example, solvent dyes, acid dyes, direct dyes, mordant dyes, etc. can be cited. As dyes, for example, compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists), and known dyes described in the Dyeing Guide (Color Dyeing Company) can be cited. Additionally, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methylene dyes, azomethine dyes, squaric dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes, etc. Among these, organic solvent-soluble dyes are preferred.

[0049] Specifically, dyes with the following Color Index (C.I.) numbers can be cited.

[0050] C.I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;

[0051] C.I. Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;

[0052] C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;

[0053] C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0054] C.I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 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;

[0055] C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. C.I. solvent dyes,

[0056] C.I. 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, 157, 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;

[0057] C.I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 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, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;

[0058] C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

[0059] C.I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

[0060] C.I. Acid Blue 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, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;

[0061] C.I. 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 C.I. acid dyes,

[0062] C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;

[0063] C.I. 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;

[0064] C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0065] C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0066] C.I. 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, 87, 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, 167, 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;

[0067] C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82 and other C.I. Direct Dyes,

[0068] C.I. Disperse Yellow 51, 54, 76;

[0069] C.I. Disperse Violet 26, 27;

[0070] C.I. Disperse Blue 1, 14, 56, 60 and other C.I. Disperse Dyes,

[0071] C.I. Basic Red 1, 10;

[0072] C.I. 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;

[0073] C.I. Basic Violet 2;

[0074] C.I. Basic Red 9;

[0075] C.I. Basic Green 1 and other C.I. basic dyes,

[0076] C.I. Reactive Yellow 2, 76, 116;

[0077] C.I. Reactive Orange 16;

[0078] C.I. Reactive Red 36 and other C.I. reactive dyes,

[0079] C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0080] C.I. Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 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;

[0081] C.I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0082] C.I. Mordant Violet 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;

[0083] C.I. Mordant 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;

[0084] C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other C.I. mordant dyes,

[0085] C.I. Vat Green 1 and other C.I. vat dyes, etc.

[0086] These dyes can be appropriately selected according to the spectral distribution of the desired color filter.

[0087] As the pigment (A2), known pigments can be used. For example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists) can be cited. Additionally, based on the chemical structure, azo pigments, cyanine pigments, triphenylmethane pigments, xanthene pigments, anthraquinone pigments, naphthoquinone pigments, quinoneimine pigments, methylene pigments, azomethine pigments, squaric -based pigments, acridine pigments, styryl pigments, coumarin pigments, quinoline pigments, nitro pigments, phthalocyanine pigments, perylene pigments, quinophthalone pigments, isoindoline pigments, etc. Among these, phthalocyanine pigments, quinophthalone pigments, isoindoline pigments, etc. are preferred.

[0088] As pigments classified as pigments, specifically, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231, etc. yellow pigments can be cited;

[0089] C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc. orange pigments;

[0090] C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 272, 273, 291, etc. red pigments;

[0091] C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc. blue pigments;

[0092] C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38, etc. purple pigments;

[0093] C.I. Pigment Green 7, 36, 58, 59, 62, 63, etc. green pigments;

[0094] C.I. Pigment Brown 23, 25, etc. brown pigments;

[0095] C.I. Pigment Black 1, 7, 31, 32, etc. black pigments, etc.

[0096] These pigments can be appropriately selected according to the spectral distribution of the desired color filter.

[0097] When preparing a green-colored curable resin composition, as the colorant (A), it is preferably to contain at least one selected from yellow dyes and yellow pigments (hereinafter, these may be collectively referred to as "yellow colorants"), green dyes and green pigments (hereinafter, these may be collectively referred to as "green colorants"), and more preferably to contain yellow pigments and / or green pigments.

[0098] As the yellow dye, dyes whose hues are classified as yellow among the above-mentioned dyes can be cited, and as the yellow pigment, pigments whose hues are classified as yellow among the above-mentioned pigments can be cited.

[0099] Among the yellow pigments, quinophthalone yellow pigments, metal-containing yellow pigments, and isoindoline yellow pigments are preferred, and at least one selected from C.I. Pigment Yellow 138, 139, 150, 185, 231, 233 is more preferred, and at least one selected from C.I. Pigment Yellow 138, 139, 150, 185 is further preferred.

[0100] As the green dye, dyes whose hues are classified as green among the above-mentioned dyes can be cited, and as the green pigment, pigments whose hues are classified as green among the above-mentioned pigments can be cited.

[0101] Among the green pigments, phthalocyanine pigments are preferred, and at least one selected from copper halide phthalocyanine pigments and zinc halide phthalocyanine pigments is more preferred, and at least one selected from C.I. Pigment Green 7, 36, 58, 59, 62, 63 is further preferred, and at least one selected from C.I. Pigment Green 58, 59 is further more preferred.

[0102] When preparing a green-colored curable resin composition, the colorant (A) preferably contains, for example, 50% by mass or more, preferably 70% by mass or more, more preferably 90% by mass or more, and particularly 95% by mass or more of yellow colorants and / or green colorants in total 100% by mass of all colorants.

[0103] In addition, it is preferably to contain both yellow colorants and green colorants. When containing both yellow colorants and green colorants, the content rate of the yellow colorant is, for example, 10% to 70% by mass, preferably 15% to 60% by mass, and more preferably 20% to 55% by mass in the total 100% by mass of the yellow colorant and the green colorant.

[0104] When containing both yellow colorants and green colorants, the content rate of the green colorant is, for example, 30% to 90% by mass, preferably 40% to 85% by mass, and more preferably 45% to 80% by mass in the total 100% by mass of the yellow colorant and the green colorant.

[0105] In addition to the green colorant and the yellow colorant, the green-colored curable resin composition may further contain the blue colorant described below.

[0106] The content rate of the blue colorant is, for example, 0 mass% to 5 mass%, preferably 0.1 mass% to 4.5 mass%, more preferably 0.2 mass% to 4.0 mass% in the total 100 mass% of the green colorant, the yellow colorant, and the blue colorant.

[0107] When preparing the red-colored curable resin composition, as the colorant (A), it is preferably to contain at least one selected from yellow colorants, red dyes, and red pigments (hereinafter, these may be collectively referred to as "red colorants"), and more preferably to contain yellow pigments and / or red pigments.

[0108] Examples of the yellow colorant are the same as those in the case of preparing the green-colored curable resin composition, and the preferred embodiments are also the same.

[0109] Examples of the red dye include dyes whose hue is classified as red among the above-mentioned dyes, and examples of the red pigment include pigments whose hue is classified as red among the above-mentioned pigments.

[0110] Among the red pigments, at least one selected from C.I. Pigment Red 122, 177, 254, 255, 264, 269, 272, 291 is preferred, and at least one selected from C.I. Pigment Red 177, 254, 269, 272, 291 is more preferred.

[0111] When preparing the red-colored curable resin composition, in the total 100 mass% of all colorants, the colorant (A) preferably contains, for example, 50 mass% or more, preferably 70 mass% or more, more preferably 90 mass% or more, and particularly 100 mass% of the yellow colorant and / or the red colorant in total. In addition, it is preferred to contain both the yellow colorant and the red colorant.

[0112] When preparing the blue-colored curable resin composition, as the colorant (A), it is preferably to contain at least one selected from blue dyes and blue pigments (hereinafter, these may be collectively referred to as "blue colorants"), and more preferably to contain blue pigments.

[0113] Examples of the blue dye include dyes whose hue is classified as blue among the above-mentioned dyes, and examples of the blue pigment include pigments whose hue is classified as blue among the above-mentioned pigments.

[0114] As the blue pigment, phthalocyanine pigments are preferred, and at least one selected from C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 16 is more preferred.

[0115] When preparing a blue-colored curable resin composition, it is preferred to contain a purple dye and a purple pigment (hereinafter sometimes collectively referred to as "purple colorants") in addition to the blue colorant.

[0116] As the purple dye, a dye whose hue is classified as purple among the above dyes can be cited, and as the purple pigment, a pigment whose hue is classified as purple among the above pigments can be cited.

[0117] As the purple colorant, a purple pigment is preferred, and among the purple pigments, at least one selected from C.I. Pigment Violet 19, 23, and 29 is more preferred.

[0118] When preparing a blue-colored curable resin composition, the colorant (A) preferably contains, for example, 30% by mass to 99% by mass, preferably 50% by mass or more, and more preferably 60% by mass or more of the blue colorant in 100% by mass of all colorants. In addition, when a purple colorant is contained, the content rate of the blue colorant is, for example, 5% by mass to 95% by mass, preferably 10% by mass to 80% by mass, and more preferably 20% by mass to 60% by mass in 100% by mass of the total of the blue colorant and the purple colorant.

[0119] When preparing a yellow-colored curable resin composition, as the colorant (A), it is preferred to contain at least one yellow colorant, more preferably to contain at least one yellow pigment, and further preferably to contain two or more yellow pigments.

[0120] As the yellow pigment, at least one selected from C.I. Pigment Yellow 129, 138, 139, 150, and 185 is preferred, and at least one selected from C.I. Pigment Yellow 138, 139, 150, and 185 is more preferred.

[0121] When preparing a yellow-colored curable resin composition, the colorant (A) preferably contains, for example, 50% by mass or more, preferably 70% by mass or more, more preferably 80% by mass or more, further preferably 90% by mass or more, and particularly 100% by mass of the yellow colorant in 100% by mass of all colorants.

[0122] When the curable resin composition containing a colorant contains a solvent (E), a liquid containing a colorant containing the colorant (A) and the solvent (E) can be prepared in advance, and then the curable resin composition containing a colorant can be prepared using the liquid containing a colorant. In the case where the colorant (A) is not soluble in the solvent (E), for example, when the colorant (A) contains a pigment (A2) or the like, the liquid containing a colorant can be prepared by dispersing and mixing the colorant (A) in the solvent (E). The liquid containing a colorant may contain a part or all of the solvent (E) contained in the curable resin composition containing a colorant.

[0123] The content rate of the solid component in the liquid containing the colorant is less than 100% by mass relative to the total amount of the liquid containing the colorant, preferably 1% to 80% by mass, more preferably 2% to 70% by mass, and further preferably 5% to 65% by mass.

[0124] The content rate of the colorant (A) in the liquid containing the colorant is less than 100% by mass relative to the total amount of the solid components in the liquid containing the colorant, preferably 0.5% to 80% by mass, more preferably 1% to 70% by mass, and further preferably 2.5% to 65% by mass.

[0125] The colorant (A) can be subjected to surface treatments such as rosin treatment, surface treatment using derivatives having an introduced acidic group or basic group, graft treatment on the surface of the colorant (A) using a polymer compound, etc., micronization treatment based on a sulfuric acid micronization method, a salt grinding method, etc., cleaning treatment using an organic solvent, water, etc. for removing impurities, removal treatment of ionic impurities using an ion exchange method, etc. The particle size of the colorant (A) is preferably substantially uniform.

[0126] The colorant (A) can be made into a state in which the colorant (A) is uniformly dispersed in the solution by performing a dispersion treatment containing a dispersant. When two or more kinds of the colorant (A) are used in combination, the dispersion treatment can be performed separately for each, or a plurality of them can be mixed and subjected to the dispersion treatment.

[0127] Examples of the dispersant include surfactants, etc., and any of cationic, anionic, nonionic, and amphoteric surfactants can be used. Specifically, surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants can be mentioned. These dispersants can be used alone or in combination of two or more. When represented by a trade name, examples of the dispersant include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Inc.), Disperbyk (registered trademark) (manufactured by BYK-Chemie GmbH), BYK (registered trademark) (manufactured by BYK-Chemie GmbH), etc. In addition, as the dispersant, the resin (B) described later (preferably resin [K1], more preferably 3,4-epoxytricyclo[5.2.1.0 2.6 decyl / (meth)acrylate copolymer) can be used. The dispersant preferably contains the above-mentioned acrylic-based dispersant and the resin (B), and preferably does not contain a copper phthalocyanine derivative.

[0128] When using a dispersant, the amount of the dispersant (solid component) used is usually 1 to 10,000 parts by mass, preferably 5 to 5,000 parts by mass, more preferably 10 to 1,000 parts by mass, and still more preferably 15 to 800 parts by mass with respect to 100 parts by mass of the colorant (A) in the liquid containing the colorant. If the amount of the dispersant used is within the above range, there is a tendency to obtain a liquid containing the colorant (hereinafter sometimes referred to as a colorant dispersion or a pigment dispersion) in a more uniform dispersion state.

[0129] After preparing a liquid containing the colorant (A) and the solvent (E) in advance, when using the liquid containing the colorant to prepare a color-curable resin composition, the liquid containing the colorant may contain a part or all, preferably a part, of the resin (B) contained in the color-curable resin composition. By containing the resin (B) in advance, the dispersion stability of the liquid containing the colorant can be further improved.

[0130] When the liquid containing the colorant contains the resin (B), the content of the resin (B) is, for example, 10 to 10,000 parts by mass, preferably 20 to 5,000 parts by mass, and more preferably 25 to 2,500 parts by mass with respect to 100 parts by mass of the colorant (A) in the liquid containing the colorant.

[0131] The content rate of the colorant (A) in the total amount of the solid components of the color-curable resin composition is preferably 1% to 80% by mass, more preferably 10% to 70% by mass, still more preferably 15% to 65% by mass, and even more preferably 18% to 50% by mass. If the content rate of the colorant (A) is within the above range, the color density when forming a color filter is sufficient, and the required amount of the resin (B) can be contained in the composition, so that a pattern with sufficient mechanical strength can be formed, which is therefore preferred.

[0132] The content rate of the colorant (A) in the total amount of the solid components of the color-curable resin composition is particularly preferably greater than 36% by mass and 90% by mass or less, and most preferably 38% to 85% by mass. If the content rate of the colorant (A) is within the above range, darkening of the color filter can be achieved.

[0133] Here, the "total amount of solid components" in this specification refers to the amount obtained by removing the content of the solvent from the total amount of the color-curable resin composition. The total amount of solid components and the content of each component relative to this total amount can be measured by known analytical means such as liquid chromatography or gas chromatography, for example.

[0134] <Resin (B)>

[0135] The resin (B) is not particularly limited, and an alkali-soluble resin is preferred. As the resin (B), the following resins [K1] to [K6] etc. can be mentioned, and at least one selected from the resins [K1] to [K6] is preferred.

[0136] Resin [K1]: A copolymer having a structural unit derived from at least one monomer (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)") and a structural unit derived from a monomer (b) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b)");

[0137] Resin [K2]: A copolymer having a structural unit derived from the above (a), a structural unit derived from the above (b), and a structural unit derived from a monomer (c) capable of copolymerizing with (a) (however, different from (a) and (b)). (hereinafter sometimes referred to as "(c)");

[0138] Resin [K3]: A copolymer having a structural unit derived from the above (a) and a structural unit derived from the above (c);

[0139] Resin [K4]: A copolymer having a structural unit obtained by adding the above (b) to a structural unit derived from the above (a) and a structural unit derived from the above (c) (preferably including a structural unit derived from (a) to which (b) has not been added);

[0140] Resin [K5]: A copolymer having a structural unit obtained by adding the above (a) to a structural unit derived from the above (b) and a structural unit derived from the above (c) (may include a structural unit derived from (b) to which (a) has not been added, but preferably does not include);

[0141] Resin [K5']: A copolymer having a structural unit obtained by adding the above (b) to a structural unit derived from the above (a) and a structural unit derived from the above (c) (may include a structural unit derived from (a) to which (b) has not been added, but preferably does not include);

[0142] Resin [K6]: A copolymer having a structural unit obtained by adding the above (a) to a structural unit derived from the above (b) and further adding a carboxylic anhydride and a structural unit derived from the above (c).

[0143] Specific examples of (a) include, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, etc.;

[0144] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, 1,4-cyclohexenedicarboxylic acid;

[0145] Bicyclic unsaturated compounds containing a carboxyl group such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;

[0146] Anhydrides of unsaturated dicarboxylic acids such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;

[0147] Unsaturated mono-[(meth)acryloyloxyalkyl] esters of polycarboxylic acids with two or more carboxyl groups such as succinic acid mono[2-(meth)acryloyloxyethyl] ester, phthalic acid mono[2-(meth)acryloyloxyethyl] ester;

[0148] Unsaturated acrylate esters containing a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl)acrylic acid;

[0149] Among these, from the aspects of copolymerization reactivity and the solubility of the resulting resin in an aqueous alkali solution, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred.

[0150] (b) refers to a polymerizable compound having, for example, a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) preferably has a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0151] It should be noted that in this specification, “(meth)acrylic acid” means at least one selected from acrylic acid and methacrylic acid. Expressions such as “(meth)acryloyl” and “(meth)acrylate” have the same meaning.

[0152] As (b), for example, monomers (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), monomers (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), monomers (b3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), etc. can be cited.

[0153] As (b1), for example, monomers (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)"), monomers (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)") can be cited.

[0154] As (b1-1), glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, etc. can be cited.

[0155] As (b1-2), vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer M100; manufactured by Daicel Corporation), the compound represented by formula (I) and the compound represented by formula (II), etc. can be cited.

[0156]

[0157] [In formula (I) and formula (II), R a and R b represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group.

[0158] X a and X b represents a single bond, *-R c -, *-R c -O-, *-R c -S- or *-R c -NH-.

[0159] R c represents an alkanediyl having 1 to 6 carbon atoms.

[0160] * represents the bonding site to O.]

[0161] As the alkyl group having 1 to 4 carbon atoms, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc. can be mentioned.

[0162] As the alkyl group in which a hydrogen atom is substituted with a hydroxyl group, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc. can be mentioned.

[0163] As R a and R b preferably, a hydrogen atom, methyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl can be mentioned, and more preferably, a hydrogen atom, methyl can be mentioned.

[0164] As the alkanediyl, methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, etc. can be mentioned.

[0165] As X a and X b preferably, a single bond, methylene, ethylene, *-CH 2 -O- and *-CH 2 CH 2 -O- can be mentioned, and more preferably, a single bond, *-CH 2 CH 2 -O- (* represents the bonding site to O).

[0166] As the compound represented by the formula (I), a compound represented by any one of the formulas (I-1) to (I-15) etc. can be mentioned. Among them, a compound represented by the formula (I-1), the formula (I-3), the formula (I-5), the formula (I-7), the formula (I-9) or the formula (I-11) to (I-15) is preferred, and a compound represented by the formula (I-1), the formula (I-7), the formula (I-9) or the formula (I-15) is more preferred.

[0167]

[0168] Examples of the compound represented by formula (II) include compounds represented by any one of formulas (II-1) to (II-15). Among them, compounds represented by formula (II-1), formula (II-3), formula (II-5), formula (II-7), formula (II-9), or formula (II-11) to (II-15) are preferred, and compounds represented by formula (II-1), formula (II-7), formula (II-9), or formula (II-15) are more preferred.

[0169]

[0170] The compound represented by formula (I) and the compound represented by formula (II) can be used alone or in combination of two or more. When the compound represented by formula (I) and the compound represented by formula (II) are used in combination, their content ratio [compound represented by formula (I): compound represented by formula (II)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20, on a molar basis.

[0171] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloxymethyl oxetane, 3-methyl-3-acryloxymethyl oxetane, 3-ethyl-3-methacryloxymethyl oxetane, 3-ethyl-3-acryloxymethyl oxetane, 3-methyl-3-methacryloxyethyl oxetane, 3-methyl-3-acryloxyethyl oxetane, 3-ethyl-3-methacryloxyethyl oxetane, 3-ethyl-3-acryloxyethyl oxetane, etc.

[0172] As (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred. Specifically, examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0173] As (b), (b1) is preferred from the viewpoint of further improving the reliability such as heat resistance and chemical resistance of the obtained color filter. Further, (b1-2) is more preferred from the viewpoint of excellent storage stability of the colored curable resin composition.

[0174] Examples of (c) include unsaturated carboxylic acid esters such as (meth)acrylate monomers and unsaturated dicarboxylic acid esters; vinyl monomers having an unsaturated aliphatic hydrocarbon ring, an unsaturated heterocyclic ring, or an aromatic ring, etc.

[0175] As (meth)acrylate monomers, for example, (meth)acrylate esters having a linear or branched aliphatic saturated hydrocarbon group such as methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, etc. (preferably C 1－10 alkyl (meth)acrylate);

[0176] (meth)acrylate esters having a linear or branched aliphatic unsaturated hydrocarbon group such as allyl (meth)acrylate, propargyl (meth)acrylate, etc.;

[0177] (meth)acrylate esters having a cyclic saturated hydrocarbon group such as cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 decane-8-yl (meth)acrylate (in this technical field, it is commonly known as “dicyclopentyl (meth)acrylate”. Additionally, it is sometimes referred to as “tricyclodecyl (meth)acrylate”), isobornyl (meth)acrylate, adamantyl (meth)acrylate, etc.;

[0178] (meth)acrylate esters having a cyclic unsaturated aliphatic hydrocarbon group such as tricyclo[5.2.1.0 2,6 decene-8-yl (meth)acrylate (in this technical field, it is commonly known as “dicyclopentenyl (meth)acrylate”), dicyclopentyloxyethyl (meth)acrylate, etc.;

[0179] (meth)acrylate esters having an aromatic ring such as phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate, phenoxybenzyl (meth)acrylate, etc.;

[0180] (meth)acrylate esters containing a hydroxyl group such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, etc.

[0181] As unsaturated dicarboxylate esters, dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconate, etc. can be cited.

[0182] Among these unsaturated carboxylate esters, (meth)acrylate C 1－10 alkyl esters such as methyl methacrylate, 2-ethylhexyl acrylate, etc.; (meth)acrylate esters having a cyclic saturated hydrocarbon group such as tricyclo[5.2.1.0 2,6 decane-8-yl (meth)acrylate, etc. are preferred; tricyclo[5.2.1.0 2,6(Meth)acrylates having a cyclic unsaturated aliphatic hydrocarbon group such as decen-8-yl (meth)acrylate; (meth)acrylates having an aromatic ring such as benzyl (meth)acrylate and phenoxybenzyl (meth)acrylate, etc.

[0183] Examples of vinyl monomers having an unsaturated aliphatic hydrocarbon ring include bicyclo[2.2.1]hept-2-ene (or also called 2-norbornene), 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-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(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 and other bicyclic unsaturated compounds.

[0184] Examples of vinyl monomers having an unsaturated heterocycle include N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl 3-maleimidobenzoate, N-succinimide 4-maleimidobutyrate, N-succinimidyl 6-maleimidohexanoate, N-succinimide 3-maleimidopropionate, N-(9-acridinyl)maleimide and other dicarbonylimide derivatives.

[0185] Examples of vinyl monomers having an aromatic ring include styrene-based monomers such as styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene.

[0186] Examples of other vinyl monomers include monomers containing a nitrile group such as acrylonitrile and methacrylonitrile;

[0187] Monomers containing halogen atoms such as vinyl chloride and vinylidene chloride;

[0188] Acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.

[0189] Among these vinyl monomers, from the aspects of copolymerization reactivity and heat resistance, styrene-based monomers such as styrene and vinyltoluene, dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, and N-benzylmaleimide, and bicyclic unsaturated compounds such as bicyclo[2.2.1]hept-2-ene (or also called 2-norbornene) are preferred.

[0190] The structural unit obtained by adding (b) to the structural unit from (a) refers to the unit formed by bonding (b) to the structural unit from (a) that constitutes the main chain of the copolymer through addition, and has a pendant unsaturated group from (b). In this structural unit, (a) can be any of the above examples, and (b) can also be any of the above examples. As (a), unsaturated monocarboxylic acids such as (meth)acrylic acid are preferred. As (b), a monomer (b1) having an oxiranyl group and an ethylenic unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred.

[0191] The structural unit obtained by adding (a) to the structural unit from (b) refers to the unit formed by bonding (a) to the structural unit from (b) that constitutes the main chain of the copolymer through addition, and has a pendant unsaturated group from (a). In this structural unit, (b) can be any of the above examples, and (a) can also be any of the above examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenic unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred. As (a), unsaturated monocarboxylic acids such as (meth)acrylic acid are preferred.

[0192] The structural unit obtained by adding (a) to the structural unit from (b) and further adding a carboxylic anhydride refers to the structural unit formed by semi-esterification of the carboxylic anhydride with the hydroxyl group generated by bonding (a) to the structural unit from (b) that constitutes the main chain of the copolymer through addition, and has a pendant carboxyl group from the carboxylic anhydride and a pendant unsaturated group from (a). In this structural unit, (b) can be any of the above examples, and (a) can also be any of the above examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenic unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred. As (a), unsaturated monocarboxylic acids such as (meth)acrylic acid are preferred.

[0193] Examples of the carboxylic anhydride include saturated aliphatic polycarboxylic anhydrides such as malonic anhydride, succinic anhydride, glutaric anhydride, and adipic anhydride; unsaturated aliphatic polycarboxylic anhydrides such as maleic anhydride, citraconic anhydride, and itaconic anhydride; aromatic polycarboxylic anhydrides such as 3-vinylphthalic anhydride and 4-vinylphthalic anhydride; and alicyclic polycarboxylic anhydrides such as 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride.

[0194] In the resin [K1], the ratio of the structural units derived from each monomer among all the structural units constituting the resin [K1] is preferably such that the structural units derived from (a) are 2 to 60 mol%, and the structural units derived from (b) are 40 to 98 mol%, more preferably the structural units derived from (a) are 10 to 50 mol%, and the structural units derived from (b) are 50 to 90 mol%.

[0195] In addition, it is preferably substantially free of the structural units derived from (c).

[0196] The total of the structural units derived from (a) and the structural units derived from (b) among all the structural units constituting the resin [K1] is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0197] When the ratio of the structural units of the resin [K1] is within the above range, there is a tendency for the storage stability of the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter to be excellent.

[0198] The resin [K1] can be produced, for example, with reference to the methods described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, issued on March 1, 1972) and the cited references in this literature.

[0199] Specifically, the following methods can be mentioned: A predetermined amount of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, and an oxygen-free atmosphere is formed, for example, by replacing oxygen with nitrogen, 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 the polymerization initiator and solvent commonly used in this field can be used. Examples of the polymerization initiator include azo compounds (such as 2,2'-azobisisobutyronitrile and 2,2'-azobis(2,4-dimethylvaleronitrile)), and organic peroxides (such as benzoyl peroxide). As the solvent, any solvent that can dissolve each monomer can be used, and examples include the solvent (E) of the colored curable resin composition of the present invention and the solvents described later.

[0200] It should be noted that for the obtained copolymer, the reaction solution can be used directly, or the concentrated or diluted solution can be used, or the substance taken out in the form of a solid (powder) by methods such as reprecipitation can be used. In particular, by using the solvent contained in the colored curable resin composition of the present invention as the solvent during this polymerization, the reaction solution can be directly used to prepare the colored curable resin composition of the present invention, so that the manufacturing process of the colored curable resin composition of the present invention can be simplified.

[0201] In resin [K2], the ratio of the structural units derived from each monomer among all the structural units constituting resin [K2] is preferably 2 to 45 mol% for the structural units derived from (a), 2 to 95 mol% for the structural units derived from (b), and 1 to 65 mol% for the structural units derived from (c). More preferably, the structural units derived from (a) are 5 to 40 mol%, the structural units derived from (b) are 5 to 80 mol%, and the structural units derived from (c) are 5 to 60 mol%. Even more preferably, the structural units derived from (a) are 10 to 30 mol%, the structural units derived from (b) are 10 to 70 mol%, and the structural units derived from (c) are 10 to 40 mol%.

[0202] The total of the structural units derived from (a), the structural units derived from (b), and the structural units derived from (c) among all the structural units constituting resin [K2] is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0203] If the ratio of the structural units of resin [K2] is within the above range, there is a tendency for the storage stability of the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained color filter to be excellent.

[0204] In resin [K2], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized is more preferred. As (c), (meth)acrylate esters having a cyclic unsaturated aliphatic hydrocarbon group, (meth)acrylate esters having an aromatic ring, and dicarbonylimide derivatives are preferred.

[0205] Resin [K2] can be produced, for example, in the same manner as the method described for the production of resin [K1].

[0206] In the resin [K3], the ratio of the structural units derived from each monomer among all the structural units constituting the resin [K3] is preferably such that the structural units derived from (a) are 2 to 60 mol%, and the structural units derived from (c) are 40 to 98 mol%. More preferably, the structural units derived from (a) are 10 to 50 mol%, and the structural units derived from (c) are 50 to 90 mol%. Even more preferably, the structural units derived from (a) are 35 to 45 mol%, and the structural units derived from (c) are 55 to 65 mol%.

[0207] In addition, it is preferably substantially free of the structural units derived from (b).

[0208] The total of the structural units derived from (a) and the structural units derived from (c) among all the structural units constituting the resin [K3] is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0209] In the resin [K3], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. (c) is preferably a (meth)acrylate having an aromatic ring.

[0210] The resin [K3] can be produced, for example, in the same manner as the method described for the production method of the resin [K1].

[0211] In the resin [K4], the ratio of the structural units derived from each monomer among all the structural units constituting the resin [K4] is preferably such that the structural units derived from (a) (without adding (b)) are 1 to 60 mol%, the structural units obtained by adding (b) to the structural units derived from (a) are 1 to 50 mol%, and the structural units derived from (c) are 30 to 90 mol%. More preferably, the structural units derived from (a) (without adding (b)) are 5 to 50 mol%, the structural units obtained by adding (b) to the structural units derived from (a) are 5 to 40 mol%, and the structural units derived from (c) are 35 to 80 mol%. Even more preferably, the structural units derived from (a) (without adding (b)) are 10 to 40 mol%, the structural units obtained by adding (b) to the structural units derived from (a) are 10 to 25 mol%, and the structural units derived from (c) are 40 to 75 mol%.

[0212] The total of the structural units derived from (a) (without adding (b)), the structural units obtained by adding (b) to the structural units derived from (a), and the structural units derived from (c) among all the structural units constituting the resin [K4] is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0213] As a structural unit from (a) (without addition of (b)), a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As a structural unit obtained by adding (b) to the structural unit from (a), a structural unit obtained by adding a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized to the structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As a structural unit from (c), one or more selected from (meth)acrylate esters having a linear or branched aliphatic saturated hydrocarbon group, (meth)acrylate esters having a cyclic saturated hydrocarbon group, (meth)acrylate esters having an aromatic ring, bicyclic unsaturated compounds, and styrene-based monomers are preferred, and more preferably two or more. When there are two constituent units from (c), (c) is preferably selected from two of unsaturated carboxylic acid esters such as (meth)acrylate esters, (meth)acrylate esters having a cyclic saturated hydrocarbon group, and (meth)acrylate esters having an aromatic ring, and two or more selected from vinyl monomers such as bicyclic unsaturated compounds and styrene-based monomers.

[0214] Resin [K4] can be produced by obtaining a copolymer of (a) and (c) and adding a cyclic ether having 2 to 4 carbon atoms in (b) to the carboxylic acid and / or carboxylic anhydride in (a).

[0215] First, a copolymer of (a) and (c) is produced in the same manner as the method described as the production method of resin [K1]. In this case, the ratio of the structural units from each monomer is preferably the same as the ratio cited in resin [K3].

[0216] Next, a cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a part of the carboxylic acid and / or carboxylic anhydride from (a) in the above copolymer.

[0217] Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced from nitrogen to air, and (b), a reaction catalyst for the carboxylic acid or carboxylic anhydride and the cyclic ether (for example, tris(dimethylaminomethyl)phenol, etc.), an inhibitor (for example, hydroquinone, etc.), etc. are placed in the flask, and for example, reacted at 60 to 130 °C for 1 to 10 hours, whereby resin [K4] can be produced.

[0218] The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, relative to 100 moles of (a). By being in this range, there is a tendency for the balance of the storage stability of the colored curable resin composition, the developability during pattern formation, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern to become good.

[0219] The usage amount of the above reaction catalyst is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c). The usage amount of the above polymerization inhibitor is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c).

[0220] Reaction conditions such as the feeding method, reaction temperature and time can be appropriately adjusted in consideration of the manufacturing equipment, the heat generated by polymerization, etc. It should be noted that the feeding method and reaction temperature can be appropriately adjusted in consideration of the manufacturing equipment, the heat generated by polymerization, etc. in the same way as the polymerization conditions.

[0221] In resin [K5], the ratio of the structural units from each monomer among all the structural units constituting resin [K5] is preferably such that the structural unit from (b) (without addition of (a)) is 0 to 30 mol%, the structural unit obtained by adding (a) to the structural unit from (b) is 5 to 95 mol%, and the structural unit from (c) is 5 to 95 mol%. More preferably, the structural unit from (b) (without addition of (a)) is 0 to 10 mol%, the structural unit obtained by adding (a) to the structural unit from (b) is 15 to 90 mol%, and the structural unit from (c) is 10 to 85 mol%. Even more preferably, the structural unit from (b) (without addition of (a)) is 0 to 5 mol%, the structural unit obtained by adding (a) to the structural unit from (b) is 20 to 80 mol%, and the structural unit from (c) is 20 to 80 mol%.

[0222] The total of the structural unit from (b) (without addition of (a)), the structural unit obtained by adding (a) to the structural unit from (b), and the structural unit from (c) among all the structural units constituting resin [K5] is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0223] As the structural unit from (b) (without addition of (a)), a structural unit from monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is preferred. As the structural unit obtained by adding (a) to the structural unit from (b), a structural unit obtained by adding an unsaturated monocarboxylic acid such as (meth)acrylic acid to the structural unit from monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is preferred. As the structural unit from (c), one or more selected from (meth)acrylate esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylate esters having a cyclic saturated hydrocarbon group are preferred, and more preferably two or more.

[0224] For resin [K5], in the first stage, it is carried out in the same manner as the manufacturing method of the above-mentioned resin [K1] to obtain a copolymer of (b) and (c). Similarly to the above, the obtained copolymer can directly use the solution after the reaction, can also use the concentrated or diluted solution, or can also use the substance taken out in the form of a solid (powder) by methods such as reprecipitation.

[0225] The ratio of the structural units from (b) and (c) relative to the total molar amount of all the structural units constituting the above-mentioned copolymer is preferably 5 to 95 mol% of the structural units from (b) and 5 to 95 mol% of the structural units from (c), more preferably 10 to 90 mol% of the structural units from (b) and 10 to 90 mol% of the structural units from (c).

[0226] Furthermore, resin [K5] can be obtained by reacting the carboxylic acid or carboxylic anhydride possessed by (a) with the cyclic ether from (b) in the copolymer of (b) and (c) under the same conditions as the manufacturing method of resin [K4].

[0227] The usage amount of (a) reacted with the above-mentioned copolymer is preferably 5 to 100 mol relative to 100 mol of (b). From the aspect that the reactivity of the cyclic ether is high and it is not easy to leave unreacted (b), as (b) used in resin [K5], (b1) is preferred, and (b1-1) is more preferred.

[0228] In resin [K5'], the ratio of the structural units from each monomer among all the structural units constituting resin [K5'] is preferably 0 to 30 mol% of the structural units from (a) (without adding (b)), 5 to 95 mol% of the structural units obtained by adding (b) to the structural units from (a), and 5 to 95 mol% of the structural units from (c), more preferably 0 to 10 mol% of the structural units from (a) (without adding (b)), 15 to 90 mol% of the structural units obtained by adding (b) to the structural units from (a), and 10 to 85 mol% of the structural units from (c), even more preferably 0 to 5 mol% of the structural units from (a) (without adding (b)), 20 to 80 mol% of the structural units obtained by adding (b) to the structural units from (a), and 20 to 80 mol% of the structural units from (c).

[0229] The total of the structural units from (a) (without adding (b)), the structural units obtained by adding (b) to the structural units from (a), and the structural units from (c) among all the structural units constituting resin [K5'] is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0230] As a structural unit from (a) (without adding (b)), a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As a structural unit obtained by adding (b) to the structural unit from (a), a structural unit obtained by adding a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized to the structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As a structural unit from (c), one or more selected from (meth)acrylate esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylate esters having a cyclic saturated hydrocarbon group are preferred, and more preferably two or more.

[0231] The resin [K5'] can be produced by referring to the production method of the above resin [K4]. The amount of (b) used may be more than 80 moles and 100 moles or less relative to 100 moles of (a).

[0232] In the resin [K6], the ratio of the structural units from each monomer in all the structural units constituting the resin [K6] is preferably such that the structural unit from (b) (without adding (a)) is 0 to 30 mol%, the structural unit obtained by adding (a) to the structural unit from (b) (without adding carboxylic anhydride) is 2 to 80 mol%, the structural unit obtained by adding (a) to the structural unit from (b) and further adding carboxylic anhydride is 2 to 60 mol%, and the structural unit from (c) is 5 to 95 mol%. More preferably, the structural unit from (b) (without adding (a)) is 0 to 10 mol%, the structural unit obtained by adding (a) to the structural unit from (b) (without adding carboxylic anhydride) is 5 to 70 mol%, the structural unit obtained by adding (a) to the structural unit from (b) and further adding carboxylic anhydride is 5 to 50 mol%, and the structural unit from (c) is 10 to 85 mol%. Even more preferably, the structural unit from (b) (without adding (a)) is 0 to 5 mol%, the structural unit obtained by adding (a) to the structural unit from (b) (without adding carboxylic anhydride) is 10 to 65 mol%, the structural unit obtained by adding (a) to the structural unit from (b) and further adding carboxylic anhydride is 20 to 80 mol%, and the structural unit from (c) is 20 to 80 mol%.

[0233] The total of the structural unit from (b) (without adding (a)), the structural unit obtained by adding (a) to the structural unit from (b) (without adding carboxylic anhydride), the structural unit obtained by adding (a) to the structural unit from (b) and further adding carboxylic anhydride, and the structural unit 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% in all the structural units constituting the resin [K6].

[0234] As a structural unit derived from (b) (without adding (a)), a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is preferred. As a structural unit obtained by adding (a) to the structural unit derived from (b) (without adding a carboxylic anhydride), a structural unit obtained by adding an unsaturated monocarboxylic acid such as (meth)acrylic acid to the structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is preferred. As a structural unit obtained by adding (a) to the structural unit derived from (b) and further adding a carboxylic anhydride, a structural unit obtained by adding an unsaturated monocarboxylic acid such as (meth)acrylic acid to the structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized and further adding a saturated aliphatic polycarboxylic anhydride such as succinic anhydride is preferred. As a structural unit derived from (c), one or more selected from (meth)acrylates having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylates having a cyclic saturated hydrocarbon group are preferred, and more preferably two or more.

[0235] For the resin [K6], as the first stage, a copolymer of (b) and (c) is obtained in the same manner as the manufacturing method of the above resin [K1]. Similarly to the above, the obtained copolymer can directly use the solution after the reaction, can also use the concentrated or diluted solution, or can also use the substance taken out in the form of a solid (powder) by methods such as reprecipitation.

[0236] The ratio of the structural units derived from (b) and (c) to the total molar number of all the structural units constituting the above copolymer is preferably 5 to 95 mol% for the structural unit derived from (b) and 5 to 95 mol% for the structural unit derived from (c), and more preferably 10 to 90 mol% for the structural unit derived from (b) and 10 to 90 mol% for the structural unit derived from (c).

[0237] Furthermore, under the same conditions as the manufacturing method of the resin [K4], the carboxylic acid or carboxylic anhydride contained in (a) is reacted with the cyclic ether derived from (b) in the copolymer of (b) and (c). The usage amount of (a) is preferably 80 to 100 moles relative to 100 moles of (b).

[0238] A carboxylic anhydride is reacted with the hydroxyl group generated by the reaction of the above cyclic ether and the carboxylic acid or carboxylic anhydride contained in (a). The usage amount of the carboxylic anhydride is preferably 0.05 to 1 mole, more preferably 0.10 to 0.8 mole, and even more preferably 0.13 to 0.7 mole relative to 1 mole of the usage amount of (a) (in other words, 1 mole of the hydroxyl group generated by using (a)).

[0239] As the resin (B), specifically, examples thereof include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate / (meth)acrylic acid copolymer and other resins [K1];

[0240] (Glycidyl (meth)acrylate / (meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid tricyclo[5.2.1.0 2,6 decene-8-yl ester copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate / (meth)acrylic acid / (meth)acrylic acid benzyl ester copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate / (meth)acrylic acid / (meth)acrylic acid phenoxybenzyl ester copolymer, 3-methyl-3-(meth)acryloxymethyloxetane / (meth)acrylic acid / styrene copolymer and other resins [K2];

[0241] (Meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and other resins [K3];

[0242] (Meth)acrylic acid benzyl ester / resin obtained by adding glycidyl (meth)acrylate to a part of the carboxyl groups of (meth)acrylic acid copolymer, tricyclodecyl (meth)acrylate / styrene / resin obtained by adding glycidyl (meth)acrylate to a part of the carboxyl groups of (meth)acrylic acid copolymer, tricyclodecyl (meth)acrylate / (meth)acrylic acid benzyl ester / resin obtained by adding glycidyl (meth)acrylate to a part of the carboxyl groups of (meth)acrylic acid copolymer, norbornene / vinyltoluene / resin obtained by adding glycidyl (meth)acrylate to a part of the carboxyl groups of (meth)acrylic acid copolymer, norbornene / styrene / resin obtained by adding glycidyl (meth)acrylate to a part of the carboxyl groups of (meth)acrylic acid copolymer and other resins [K4];

[0243] Resins such as tricyclodecanyl (meth)acrylate / resin obtained by reacting (meth)acrylic acid with a copolymer of (meth)acrylic acid and glycidyl (meth)acrylate, tricyclodecanyl (meth)acrylate / styrene / resin obtained by reacting (meth)acrylic acid with a copolymer of (meth)acrylic acid and glycidyl (meth)acrylate, etc. [K5];

[0244] Resins such as tricyclodecanyl (meth)acrylate / resin obtained by reacting a copolymer of glycidyl (meth)acrylate and (meth)acrylic acid, tricyclodecanyl (meth)acrylate / styrene / resin obtained by reacting a copolymer of three glycidyl (meth)acrylates and (meth)acrylic acid, etc. [K5'];

[0245] Resins such as tricyclodecanyl (meth)acrylate / resin obtained by further reacting the resin obtained by reacting (meth)acrylic acid with a copolymer of (meth)acrylic acid and glycidyl (meth)acrylate with tetrahydrophthalic anhydride, 2-ethylhexyl (meth)acrylate / tricyclodecanyl (meth)acrylate / resin obtained by further reacting the resin obtained by reacting (meth)acrylic acid with a copolymer of (meth)acrylic acid and glycidyl (meth)acrylate with succinic anhydride, methyl (meth)acrylate / 2-ethylhexyl (meth)acrylate / tricyclodecanyl (meth)acrylate / resin obtained by further reacting the resin obtained by reacting (meth)acrylic acid with a copolymer of (meth)acrylic acid and glycidyl (meth)acrylate with succinic anhydride, etc. [K6], etc.

[0246] The weight-average molecular weight of resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and further preferably 5,000 to 30,000. If the molecular weight is within the above range, there is a tendency for the hardness of the color filter to increase, the residual film rate to be high, the solubility of the unexposed portion in the developer to be good, and the resolution of the colored pattern to increase.

[0247] The dispersity [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] of resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.

[0248] The acid value of resin (B) in terms of solid content is preferably 20 to 170 mg-KOH / g, more preferably 25 to 150 mg-KOH / g, and further preferably 30 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be obtained, for example, by titration using an aqueous potassium hydroxide solution.

[0249] The content rate of the resin (B) relative to the total amount of solid components is preferably 2 to 65% by mass, more preferably 3 to 60% by mass, still more preferably 5 to 55% by mass, still more preferably 5 to 40% by mass, and particularly preferably 7 to 30% by mass. If the content rate of the resin (B) is within the above range, a colored pattern can be formed, and there is a tendency for the resolution and the residual film rate of the colored pattern to be improved.

[0250] As the resin (B), from the viewpoint of further improving the solvent resistance, a resin having an ethylenic double bond is particularly preferred. When having an ethylenic double bond, the double bond equivalent of the resin (B) is, for example, 100 to 2000 g / mol, preferably 200 to 1500 g / mol, and more preferably 300 to 1300 g / mol. As the resin (B) having an ethylenic double bond, for example, any one of resins [K2] to [K6] can be mentioned, and a resin containing at least one selected from (meth)acrylates having a linear or branched aliphatic unsaturated hydrocarbon group, (meth)acrylates having a cyclic unsaturated aliphatic hydrocarbon group, vinyl monomers having an unsaturated aliphatic hydrocarbon ring, vinyl monomers having an unsaturated heterocycle, and vinyl monomers having an aromatic ring as the monomer (c). In addition, resins [K4] to [K6] also have an ethylenic double bond derived from an addition component (preferably the above monomer (a) or the above monomer (b)).

[0251] In addition, as the resin (B), resins such as the resin [K1] and / or the resin [K2] having a structural unit derived from the monomer (b) are also particularly preferred.

[0252] Furthermore, as the resin (B), any one of resins [K2] to [K4] is also particularly preferred, and a resin containing (meth)acrylates having an aromatic ring as the monomer (c), and in 100 mol% of all the structural units, the total of the structural units derived from (meth)acrylates having an aromatic ring and the structural units derived from the above (a) is 60 mol% or more.

[0253] <Polymerizable compound (C)>

[0254] The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or an acid generated from a polymerization initiator (D). For example, compounds having a polymerizable ethylenic unsaturated bond can be mentioned, and (meth)acrylate compounds are preferred.

[0255] As the polymerizable compound having one ethylenic unsaturated bond, for example, nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc., and the above monomer (a), monomer (b), and monomer (c) can be mentioned.

[0256] Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6 - hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3 - methylpentanediol di(meth)acrylate.

[0257] The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol - modified pentaerythritol tetra(meth)acrylate, ethylene glycol - modified dipentaerythritol hexa(meth)acrylate, propylene glycol - modified pentaerythritol tetra(meth)acrylate, propylene glycol - modified dipentaerythritol hexa(meth)acrylate, caprolactone - modified pentaerythritol tetra(meth)acrylate, and caprolactone - modified dipentaerythritol hexa(meth)acrylate. Preferred examples include dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0258] The weight - average molecular weight of the polymerizable compound (C) is preferably from 50 to 4000, more preferably from 70 to 3500, still more preferably from 100 to 3000, even more preferably from 150 to 2900, and particularly preferably from 250 to 1500.

[0259] The content of the polymerizable compound (C) relative to the total solid content of the colored curable resin composition can be, for example, from 1% by mass to 99% by mass, preferably from 3% by mass to 90% by mass, more preferably from 5% by mass to 80% by mass, and still more preferably from 7% by mass to 70% by mass.

[0260] <Polymerization initiator (D)>

[0261] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light, heat, etc. and initiate polymerization, and includes the compounds represented by the following formula (I).

[0262]

[0263] (In the formula, R 1 、R 2 、R 3, R 4 and R 5 each independently represents a hydrocarbon group which may have substituents.

[0264] n represents any integer from 0 to 4.

[0265] -CH 2 - in the above hydrocarbon group may be substituted with -O-, -S-, -CO- or -OCO-.

[0266] As the hydrocarbon groups represented by R 1 , R 2 , R 3 , R 4 and R 5 , there may be mentioned saturated hydrocarbon groups having 1 to 20 carbon atoms, unsaturated aliphatic hydrocarbon groups having 1 to 20 carbon atoms, aromatic hydrocarbon groups having 6 to 20 carbon atoms, and the like.

[0267] As the saturated hydrocarbon groups having 1 to 20 carbon atoms, for example, there may be mentioned linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, icosyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl; alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, tricyclodecyl. The number of carbon atoms of the saturated hydrocarbon group is preferably 1 to 18, more preferably 1 to 15, still more preferably 1 to 10, and even more preferably 1 to 8.

[0268] As the unsaturated aliphatic hydrocarbon groups having 1 to 20 carbon atoms, there may be mentioned alkenyl groups such as vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, hexadecenyl, octadecenyl, icosenyl; alkynyl groups such as ethynyl, propynyl, hexynyl, decynyl, icosynyl; cycloalkenyl groups such as cyclopentenyl, cyclohexenyl, cycloheptenyl. The number of carbon atoms of the unsaturated aliphatic hydrocarbon group is preferably 2 to 18, more preferably 2 to 15, still more preferably 2 to 10.

[0269] As the aromatic hydrocarbon groups having 6 to 20 carbon atoms, there may be mentioned phenyl, xylenyl, trimethylphenyl, dipropylphenyl, bis(2,2-dimethylpropyl)phenyl, naphthyl, benzyl, phenylethyl, phenylbutyl. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 15, still more preferably 6 to 12.

[0270] As R 1 , R 2 , R 3 , R 4 and R 5The substituent that the hydrocarbon group represented by may have includes a halogen atom, a cyano group, and a nitro group. The halogen atom is preferably a fluorine atom, a bromine atom, a chlorine atom, or an iodine atom.

[0271] n represents any integer of 0 to 4, is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, further preferably an integer of 0 or 1, and further more preferably 0.

[0272] The -CH 2 - can be substituted by -O-, -S-, -CO- or -OCO-, the adjacent -CH 2 - is not replaced by the same group at the same time, the terminal -CH 2 - will not be replaced.

[0273] R 1 , R 2 , R 3 , R 4 and R 5 The hydrocarbon group represented is preferably a saturated hydrocarbon group having 1 to 20 carbon atoms or an unsaturated aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, further preferably a straight-chain or branched saturated hydrocarbon group having 1 to 10 carbon atoms, and still more preferably a straight-chain or branched alkyl group having 1 to 8 carbon atoms.

[0274] R 1 , R 2 , R 3 , R 4 and R 5 The hydrocarbon groups represented may be the same or different, and are preferably different.

[0275] Among them, R is preferred 1 is a chain alkyl group having 1 to 8 carbon atoms, R 2 is a branched alkyl group having 1 to 8 carbon atoms, R 3 and R 4 is a chain alkyl group having 1 to 8 carbon atoms, R 5 is a linear or branched alkyl group having 1 to 8 carbon atoms, and more preferably R 1 is a chain alkyl group having 1 to 6 carbon atoms, R 2 is a branched alkyl group having 1 to 8 carbon atoms, R 3 and R 4 is a chain alkyl group having 1 to 3 carbon atoms, R 5 It is a linear or branched alkyl group having 1 to 8 carbon atoms.

[0276] In addition to the compound represented by the formula (I), other polymerization initiators can also be used. As other polymerization initiators (D), examples thereof include O-acyl oxime compounds (excluding the compound represented by the formula (I) and Irgacure OXE03), alkyl phenyl ketone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds, etc.

[0277] The above O-acyl oxime compound is a compound having a partial structure represented by the formula (d-1). In the formula, * represents a bonding site.

[0278]

[0279] As the above O-acyl oxime compounds, for example, 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-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentylmethoxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, etc. can be cited. Commercially available products such as Irgacure OXE01 (N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine), Irgacure OXE02 (N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine) (the above are manufactured by BASF), N-1919 (manufactured by ADEKA), etc. can also be used. Among them, the O-acyl oxime compound is preferably at least one selected from N-acetoxy-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-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, more preferably N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine. If these O-acyl oxime compounds are used, there is a tendency to obtain an optical filter with high brightness.

[0280] The above alkyl phenyl ketone compound is a compound having a partial structure represented by the formula (d-2) or a partial structure represented by the formula (d-3). In these partial structures, the benzene ring may have a substituent. In the formula, * represents a bonding site.

[0281]

[0282] As a compound having a partial structure represented by the formula (d-2), for example, 2-methyl-2-morpholino-1-(4-methylthiophenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. can be cited. Commercially available products such as Irgacure 369, Irgacure 907, Irgacure 379 (the above are manufactured by BASF) can also be used.

[0283] As a compound having a partial structure represented by the formula (d-3), for example, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, benzil dimethyl ketal, etc. can be cited.

[0284] From the aspect of sensitivity, as an alkyl phenyl ketone compound, a compound having a partial structure represented by the formula (d-2) is preferred.

[0285] As the above-mentioned triazine compounds, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)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. can be cited.

[0286] As the above-mentioned acylphosphine oxide compound, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, etc. can be cited. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can also be used.

[0287] As the above-mentioned benzimidazole compounds, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)benzimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)benzimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)benzimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Laid-Open No. 62-174204, etc.), benzimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carbalkoxy groups (for example, refer to Japanese Patent Laid-Open No. 7-10913, etc.), etc. Among them, compounds represented by the following formula and their mixtures are preferred.

[0288]

[0289] Furthermore, as the polymerization initiator (D), examples thereof include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl phenylglyoxylate, titanocene compounds, etc. These are preferably used in combination with a polymerization initiation aid (D1) (especially an amine compound) described later.

[0290] As the polymerization initiator that generates an acid, for example, 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, etc. salts, nitrobenzyl tosylates, benzoin tosylates, etc.

[0291] As the polymerization initiator (D), a polymerization initiator containing at least one selected from alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds is preferred, a polymerization initiator containing an O-acyl oxime compound and / or a biimidazole compound is more preferred, and a polymerization initiator containing an O-acyl oxime compound is further preferred.

[0292] The content of the polymerization initiator (D) is preferably 0.1 part by mass to 30 parts by mass, more preferably 1 part by mass to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the content of the polymerization initiator (D) is within the above range, there is a tendency to increase sensitivity and shorten the exposure time, so the productivity of the optical filter is improved.

[0293] The content ratios of the resin (B), the polymerizable compound (C), and the polymerization initiator (D) in the total amount of the solid components of the colored curable resin composition are preferably 10% by mass or more and less than 46% by mass, more preferably 12% by mass or more and 44% by mass or less, further preferably 14% by mass to 42% by mass, and still further preferably 16% by mass to 40% by mass.

[0294] If the content ratios of the resin (B), the polymerizable compound (C), and the polymerization initiator (D) satisfy the above range, the residual film ratio of the color filter can be improved even if the curing component is reduced.

[0295] <Polymerization initiator assistant (D1)>

[0296] The polymerization initiator assistant (D1) is a compound or a sensitizer for promoting the polymerization of the polymerizable compound (C) initiated by the polymerization initiator (D). When the polymerization initiator assistant (D1) is included, it is usually used in combination with the polymerization initiator (D).

[0297] Examples of the polymerization initiator assistant (D1) include amine compounds, alkoxy anthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0298] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-(dimethylamino)ethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone. Preferred is 4,4'-bis(diethylamino)benzophenone. In addition, as the amine compound, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) can also be used.

[0299] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, and the like.

[0300] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like.

[0301] Examples of the carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, and the like.

[0302] When using these polymerization initiator aids (D1), the content is preferably 0.1 part by mass to 30 parts by mass, more preferably 1 part by mass to 20 parts by mass, based on 100 parts by mass of the total amount of all resins (B) and polymerizable compounds (C) contained in the colored curable resin composition.

[0303] <Solvent (E)>

[0304] The solvent (E) is not particularly limited, and solvents commonly used in the art can be employed.

[0305] Examples of the solvent (E) include ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing -OH in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like. Two or more of these solvents can be used in combination.

[0306] Examples of the ester solvent 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, cyclohexyl acetate, and γ-butyrolactone, and the like.

[0307] As the ether solvent, examples thereof 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-di alkane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole, etc.

[0308] As the ether ester solvent, examples thereof include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate, etc.

[0309] As the ketone solvent, examples thereof include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone, etc.

[0310] As the alcohol solvent, examples thereof include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol, etc.

[0311] As the aromatic hydrocarbon solvent, examples thereof include benzene, toluene, xylene, mesitylene, etc.

[0312] As the amide solvent, examples thereof include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, etc.

[0313] As the solvent (E), propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and cyclohexanone are preferred, and propylene glycol monomethyl ether acetate and propylene glycol monomethyl ether are more preferred.

[0314] When the solvent (E) is included, the content rate of the solvent (E) is usually 99.99% by mass or less, preferably 40% to 99% by mass, more preferably 50% to 97% by mass, further preferably 70% to 96% by mass, and still more preferably 73% to 95% by mass with respect to the total amount of the colored curable resin composition. In other words, the total amount of the solid components of the colored curable resin composition is usually 0.01% by mass or more, preferably 1% to 60% by mass, more preferably 3% to 50% by mass, further preferably 4% to 30% by mass, and still more preferably 5% to 27% by mass. When the content rate of the solvent (E) is within the above range, the flatness during coating becomes good, and the color density is not insufficient when forming a color filter, so that the display characteristics tend to become good.

[0315] <Mercaptan compound (T)>

[0316] The colored curable resin composition of the present invention may contain a mercaptan compound (T). The mercaptan compound (T) is a compound having a sulfhydryl group (-SH) in the molecule.

[0317] Examples of the compound having one sulfanyl group in the molecule include 2-sulfanyl azole, 2-sulfanylthiazole, 2-sulfanylbenzimidazole, 2-sulfanylbenzothiazole, 2-sulfanylbenzo Oxazoles, 2-mercaptonicotinic acid, 2-mercaptopyridine, 2-mercaptopyridin-3-ol, 2-mercaptopyridine-N-oxide, 4-amino-6-hydroxy-2-mercaptopyrimidine, 4-amino-6-hydroxy-2-mercaptopyrimidine, 4-amino-2-mercaptopyrimidine, 6-amino-5-nitroso-2-thiouracil, 4,5-diamino-6-hydroxy-2-mercaptopyrimidine, 4,6-diamino-2-mercaptopyrimidine, 2,4-diamino-6-mercaptopyrimidine, 4,6-dihydroxy-2-mercaptopyrimidine, 4,6-dimethyl-2-mercaptopyrimidine, 4-hydroxy-2-mercapto-6-methylpyrimidine, 4-hydroxy-2-mercapto-6-propylpyrimidine, 2-mercapto-4-methylpyrimidine, 2-mercaptopyrimidine, 2-thiouracil, 3,4,5,6-tetrahydropyrimidine-2-thiol, 4,5-diphenylimidazole-2-thiol, 2-mercaptoimidazole, 2-mercapto-1-methylimidazole, 4-amino-3-hydrazino-5-mercapto-1,2,4-triazole, 3-amino-5-mercapto-1,2,4-triazole, 2-methyl-4H-1,2,4-triazole-3-thiol, 4-methyl-4H-1,2,4-triazole-3-thiol, 3-mercapto-1H-1,2,4-triazole-3-thiol, 2-amino-5-mercapto-1,3,4-thiadiazole, 5-amino-1,3,4-thiadiazole-2-thiol, 2,5-dimercapto-1,3,4-thiadiazole, (furan-2-yl)methanethiol, 2-mercapto-5-thiazolidinone, 2-mercaptobenzothiazoline, 2-mercapto-4(3H)-quinazolinone, 1-phenyl-1H-tetrazole-5-thiol, 2-quinolinethiol, 2-mercapto-5-methylbenzimidazole, 2-mercapto-5-nitrobenzimidazole, 6-amino-2-mercaptobenzothiazole, 5-chloro-2-mercaptobenzothiazole, 6-ethoxy-2-mercaptobenzothiazole, 6-nitro-2-mercaptobenzothiazole, 2-mercaptonaphthoimidazole, 2-mercaptonaphtho Oxazoles, 3-mercapto-1,2,4-triazole, 4-amino-6-mercapto pyrazolo[2,4-d]pyridine, 2-amino-6-purinethiol, 6-mercaptopurine, 4-mercapto-1H-pyrazolo[2,4-d]pyrimidine, etc.

[0318] Examples of the compounds having two or more mercapto groups in the molecule include hexanedithiol, decanedithiol, 1,4-bis(methylthio)benzene, butanediol bis(3-mercaptopropionate), butanediol bis(3-mercaptoacetate), ethylene glycol bis(3-mercaptoacetate), trimethylolpropane tris(3-mercaptoacetate), butanediol bis(3-mercaptopropionate), trimethylolpropane tris(3-mercaptopropionate), trimethylolpropane tris(3-mercaptoacetate), pentaerythritol tetra(3-mercaptopropionate), pentaerythritol tetra(3-mercaptoacetate), triethanolamine tris(3-mercaptopropionate), pentaerythritol tetra(3-mercaptobutyrate), 1,4-bis(3-mercaptobutoxy)butane, etc.

[0319] The content of the thiol compound (T) is preferably 0.5 to 50 parts by mass, more preferably 5 to 45 parts by mass, and still more preferably 10 to 40 parts by mass with respect to 100 parts by mass of the polymerization initiator (D). If the content of the thiol compound (T) is within this range, there is a tendency for the sensitivity to increase and the developability to become good.

[0320] <Leveling agent (F)>

[0321] Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. They may have a polymerizable group in the side chain.

[0322] Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specifically, 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 Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC) etc.

[0323] As the fluorine-based surfactant, surfactants having a fluorocarbon chain in the molecule can be mentioned. Specifically, FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Limited), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by AGC Inc.), and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.) etc. can be mentioned.

[0324] As the silicone-based surfactant having a fluorine atom, surfactants having a siloxane bond and a fluorocarbon chain in the molecule can be mentioned. Specifically, MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation) etc. can be mentioned.

[0325] When the leveling agent (F) is contained, the content rate of the leveling agent (F) is preferably 0.0005% by mass to 1% by mass, more preferably 0.001% by mass to 0.5% by mass, and further preferably 0.005% by mass to 0.1% by mass with respect to the total amount of the colored curable resin composition. It should be noted that the content does not include the content of the pigment dispersant. If the content rate of the leveling agent (F) is within the above range, the flatness of the color filter can be made good.

[0326] <Other Components>

[0327] The colored curable resin composition may contain, as needed, additives well-known in the art such as fillers, other high molecular compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, etc.

[0328] Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and N-phenyl-3-aminopropyltriethoxysilane, etc.

[0329] <Manufacturing Method of Colored Curable Resin Composition>

[0330] The colored curable resin composition can be prepared by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and, if necessary, a polymerization initiator assistant (D1), a solvent (E), a leveling agent (F), and other components. The mixing can be carried out by known or conventional devices and conditions.

[0331] The colorant (A) can be pre-mixed with a part or all of the solvent (E) and dispersed to an average particle size of about 0.2 μm or less using a bead mill or the like and used in the form of a liquid containing the colorant, and it is preferably used in the form of a liquid containing the colorant. At this time, the above-mentioned dispersant, a part or all of the resin (B) can be blended as needed. By mixing the remaining components in the liquid containing the colorant thus obtained so as to achieve a specified concentration, the target colored curable resin composition can be prepared.

[0332] In addition, when the colorant (A) contains a dye, the dye can be pre-dissolved in a part or all of the solvent (E) to prepare a solution. It is preferable to filter the solution using a filter with a pore size of about 0.01 to 1 μm.

[0333] <Manufacturing Method of Color Filter>

[0334] A color filter can be formed from the color-curable resin composition of the present invention. As a method for manufacturing a colored pattern, there can be mentioned a photolithography method, an inkjet method, a printing method, etc. Among them, the photolithography method is preferred. The photolithography method is a method in which the above-mentioned color-curable resin composition is coated on a substrate, dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the photolithography method, a colored coating film, which is a cured product of the above-mentioned colored composition layer, can be formed by not using a photomask and / or not performing development during exposure. The colored pattern and the colored coating film thus formed are the color filter of the present invention.

[0335] The film thickness of the manufactured color filter is not particularly limited and can be appropriately adjusted according to the purpose, use, etc. For example, it is 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, further preferably 4.5 μm or less, preferably 0.1 μm or more, more preferably 0.2 μm or more, and further preferably 0.3 μm or more.

[0336] As the substrate, glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass with a silica coating on the surface, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, substrates with an aluminum, silver, silver / copper / palladium alloy thin film, etc. formed on the above-mentioned substrates, etc. can be used. Other color filter layers, resin layers, transistors, circuits, etc. can be formed on these substrates. In addition, a substrate subjected to HMDS (hexamethyldisilazane) treatment on a silicon substrate can also be used.

[0337] The formation of each color pixel based on the photolithography method can be carried out under known or conventional devices and conditions. For example, it can be manufactured as follows.

[0338] First, the color-curable resin composition is coated on a substrate, and heated and dried (pre-baked) and / or dried under reduced pressure to remove volatile components such as solvents and make it dry, thereby obtaining a smooth colored composition layer. As the coating method, there can be mentioned a spin coating method, a slit coating method, a slit and spin coating method, etc. The temperature during heating and drying is preferably 30°C to 120°C, more preferably 50°C to 110°C. In addition, as the heating time, it is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

[0339] When drying under reduced pressure, it is preferably carried out under a pressure of 50 Pa to 150 Pa and within a temperature range of 20°C to 25°C. The film thickness of the colored composition layer is not particularly limited and can be appropriately selected according to the film thickness of the target color filter.

[0340] Next, the colored composition layer is exposed through a photomask for forming a target colored pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target use can be used. In addition, in order to be able to uniformly irradiate parallel light onto the entire exposure surface and perform precise alignment of the photomask and the substrate on which the colored composition layer is formed, exposure apparatuses such as a mask aligner and a stepper are preferably used. In the case of forming a colored coating film, it is only necessary not to use a photomask for exposure.

[0341] As the light source used in the exposure, a light source that generates light with a wavelength of 250 nm to 450 nm is preferred. For example, for light with a wavelength less than 350 nm, a filter that cuts off this wavelength region can be used to cut it off, or for light near 436 nm, near 408 nm, or near 365 nm, a band-pass filter that extracts these wavelength regions can be used for selective extraction. Specifically, a mercury lamp, a light-emitting diode, a metal halide lamp, a halogen lamp, etc. can be mentioned.

[0342] The exposed colored composition layer is brought into contact with a developer for development, thereby forming a colored pattern on the substrate. By development, the unexposed portion of the colored composition layer is dissolved in the developer and removed. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Further, the developer may contain a surfactant. The development method can be any one of a puddle method, an immersion method, and a spray method, etc. Further, the substrate can be tilted at an arbitrary angle during development.

[0343] The developed substrate is preferably washed with water.

[0344] It is preferred to further perform post-baking on the obtained colored pattern or colored coating film. The post-baking temperature is preferably 80°C to 250°C, more preferably 100°C to 245°C. The post-baking time is preferably 1 minute to 120 minutes, more preferably 2 minutes to 30 minutes.

[0345] The colored pattern and colored coating film thus obtained are useful as color filters.

[0346] From the viewpoint of solvent resistance, the colored coating film is preferably a colored coating film in which the color difference (ΔE*ab) before and after immersion in propylene glycol monomethyl ether acetate (PGMEA) or propylene glycol monomethyl ether (PGME) at a temperature of 23°C for 5 minutes is small.

[0347] The color difference (ΔE*ab) of the colored coating film with respect to PGME is preferably 5.5 or less, more preferably 5.0 or less, further preferably 4.5 or less, and further more preferably 4.0 or less.

[0348] <Display device, solid-state imaging device>

[0349] The above-described color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state imaging device.

[0350] Examples

[0351] Hereinafter, examples will be given to illustrate the present invention more specifically. However, the present invention is not originally limited to the following examples, and of course, it can also be appropriately modified and implemented within the scope suitable for the above and the following gists, and they are all included in the technical scope of the present invention. It should be noted that hereinafter, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

[0352] <Synthesis Example 1: Preparation of Pigment Dispersion (A-1)>

[0353] The following components were mixed, and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion (A-1).

[0354]

[0355]

[0356] <Synthesis Example 2: Preparation of Pigment Dispersion (A-2)>

[0357] The following components were mixed, and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion (A-2).

[0358]

[0359] <Synthesis Example 3: Preparation of Pigment Dispersion (A-3)>

[0360] The following components were mixed, and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion (A-3).

[0361]

[0362] <Synthesis Example 4: Preparation of Pigment Dispersion (A-4)>

[0363] The following components were mixed, and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion (A-4).

[0364]

[0365] <Synthesis Example 5: Preparation of Resin (B-1)>

[0366] In a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 276.8 parts of propylene glycol monomethyl ether acetate was taken, and while nitrogen replacement was carried out, it was stirred and heated to 120 °C. Next, a substance obtained by adding 35.3 parts of tert-butyl peroxy-2-ethylhexanoate (polymerization initiator) to a monomer mixture composed of 92.4 parts of 2-ethylhexyl acrylate, 184.9 parts of glycidyl methacrylate, and 12.3 parts of dicyclopentanyl methacrylate was added dropwise from the dropping funnel to the above flask over 2 hours. After the addition was completed, the mixture was further stirred at 120 °C for 30 minutes to carry out a copolymerization reaction to form an addition copolymer. Then, the flask was replaced with air, 93.7 parts of acrylic acid, 1.5 parts of triphenylphosphine (catalyst), and 0.8 part of methoquinone (polymerization inhibitor) were added to the above addition copolymer solution, and the reaction was continued at 110 °C for 10 hours. While the epoxy group from glycidyl methacrylate reacted with acrylic acid to break the epoxy group, a polymerizable unsaturated bond was introduced into the side chain of the polymer. Next, 24.2 parts of succinic anhydride was added to the reaction system, and the reaction was continued at 110 °C for 1 hour to react the hydroxyl group generated by the cleavage of the epoxy group with succinic anhydride to introduce a carboxyl group into the side chain, obtaining a polymer. Finally, 383.3 parts of propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a solution of a polymer (resin (B-1)) with a polymer solid content of 40%. The weight average molecular weight Mw of the resulting copolymer (polymer; resin (B-1)) was 6.3×10 3 , and the acid value in terms of solid content was 34 mg-KOH / g. The vinyl double bond equivalent of resin (B-1) was 350 g / mol.

[0367] <Synthesis Example 6: Preparation of Resin (B-2)>

[0368] Nitrogen was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, and a dropping funnel at a rate of 0.02 L / minute to form a nitrogen atmosphere, 268 parts of ethyl lactate was placed, and it was heated to 70 °C while stirring. Next, 55 parts of acrylic acid, 81 parts of N-cyclohexylmaleimide, 224 parts of 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate (a compound represented by the following formula (I-1) and a compound represented by the formula (II-1) were mixed at a molar ratio of 50:50), and 224 parts of tricyclo[5.2.1.0 2,6Dec-8-yl ester (prepared by mixing the compound represented by the following formula (c-1) and the compound represented by formula (c-2) at a molar ratio of 50:50) 7 parts was dissolved in 140 parts of ethyl lactate to prepare a solution, and this solution was added dropwise to a flask maintained at 70 °C over 4 hours using a dropping funnel. On the other hand, a solution prepared by dissolving 30 parts of the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) in 225 parts of ethyl lactate was added dropwise to the flask over 4 hours using another dropping funnel. After the addition of the polymerization initiator solution was completed, it was maintained at 70 °C for 4 hours and then cooled to room temperature to obtain a copolymer (polymer; resin (B-2)) solution having a weight-average molecular weight Mw of 11.2×10 3 , a solid content of 36.7%, and a solution acid value of 44 mg-KOH / g. If the solid content acid value is calculated from the above solid content and solution acid value, it is 119 mg-KOH / g.

[0369]

[0370] <Synthesis Example 7: Preparation of a dispersion resin>

[0371] An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to displace it with a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was placed and heated to 80 °C while stirring. Next, a mixed solution of 38 parts of acrylic acid, 289 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2 ,6 decane-9-yl acrylate (containing a molar ratio of 1:1) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, it was maintained at 80 °C for 4 hours and then cooled to room temperature to obtain a copolymer (polymer; resin (B-X)) solution having a solid content of 35.1% and a viscosity of 125 mPa·s measured by a B-type viscometer (23 °C). The weight-average molecular weight Mw of the resulting copolymer was 9.2×10 3 , the dispersity was 2.08, and the acid value in terms of solid content was 77 mg-KOH / g. Resin (B-X) has the following structural units.

[0372]

[0373] Resin (B-3): Trade name "Ripox (registered trademark) SPC-2000" manufactured by Resonac Co., Ltd.

[0374] <Synthesis Example 9: Preparation of Resin (B-4)>

[0375] 241 parts of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube. While stirring, nitrogen replacement was carried out and the temperature was raised to 130 °C.

[0376] Next, a substance obtained by adding 33.5 parts of tert-butyl peroxy-2-ethylhexanoate to a monomer mixture composed of 72.6 parts of 2-ethylhexyl acrylate, 145.3 parts of glycidyl methacrylate, and 9.7 parts of dicyclopentanyl methacrylate was added dropwise to the above flask from the dropping funnel over 2 hours. After the addition was completed, stirring was continued for 30 minutes to carry out a copolymerization reaction.

[0377] Then, the inside of the flask was replaced with air, 73.7 parts of acrylic acid, 0.9 part of triphenylphosphine, and 0.9 part of methyl quinone were added, and the reaction was continued at 120 °C for 10 hours. Next, 65.2 parts of succinic anhydride was added to the reaction system, and the reaction was further continued for 1.5 hours to obtain a polymer. Finally, 300 parts of propylene glycol monomethyl ether acetate was added to the reaction solution, and then propylene glycol monomethyl ether acetate was added so that the polymer solid content concentration became 40%, to obtain a solution of the polymer (resin (B-4)). The vinyl double bond equivalent of resin (B-4) was 400 g / mol.

[0378] <Synthesis Example 10: Preparation of Resin (B-5)>

[0379] 258 parts of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube. While stirring, nitrogen replacement was carried out and the temperature was raised to 120 °C.

[0380] Next, a substance obtained by adding 10.9 parts of tert-butyl peroxy-2-ethylhexanoate to a monomer mixture composed of 89.5 parts of 2-ethylhexyl acrylate, 180.0 parts of glycidyl methacrylate, and 11.9 parts of dicyclopentanyl methacrylate was added dropwise to the above flask from the dropping funnel over 2 hours. After the addition was completed, stirring was continued for 30 minutes to carry out a copolymerization reaction.

[0381] Then, the inside of the flask was replaced with air, 90.8 parts of acrylic acid, 1.1 part of triphenylphosphine, and 1.1 part of methyl quinone were added, and the reaction was continued at 120 °C for 10 hours. Next, 18.0 parts of succinic anhydride was added to the reaction system, and the reaction was further continued for 30 minutes to obtain a polymer. Finally, 330 parts of propylene glycol monomethyl ether acetate was added to the reaction solution, and then propylene glycol monomethyl ether acetate was added so that the polymer solid content concentration became 40%, to obtain a solution of the polymer (resin (B-5)). The vinyl double bond equivalent of resin (B-5) was 330 g / mol.

[0382] <Synthesis Example 11: Preparation of Resin (B-6)>

[0383] 257 parts of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube. While stirring with nitrogen replacement, the temperature was raised to 120 °C.

[0384] Next, a substance obtained by adding 6.8 parts of tert-butyl peroxy-2-ethylhexanoate to a monomer mixture consisting of 90.5 parts of 2-ethylhexyl acrylate, 181.1 parts of glycidyl methacrylate, and 12.0 parts of dicyclopentanyl methacrylate was added dropwise to the above flask from the dropping funnel over 2 hours. After the addition was completed, stirring was continued for 30 minutes for copolymerization reaction.

[0385] Then, the inside of the flask was replaced with air, 91.8 parts of acrylic acid, 1.1 parts of triphenylphosphine, and 1.1 parts of methyl quinone were added, and the reaction was continued at 120 °C for 10 hours. Next, 17.9 parts of succinic anhydride was added to the reaction system, and the reaction was further continued for 30 minutes to obtain a polymer. Finally, 330 parts of propylene glycol monomethyl ether acetate was added to the reaction solution, and propylene glycol monomethyl ether acetate was added so that the polymer solid content concentration became 40%, to obtain a solution of polymer (resin (B-6)). The vinyl double bond equivalent of resin (B-6) was 370 g / mol.

[0386] <Synthesis Example 12: Preparation of Resin (B-7)>

[0387] 178 parts of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube. While stirring with nitrogen replacement, the temperature was raised to 100 °C.

[0388] Next, a substance obtained by adding 47.1 parts of dimethyl 2,2'-azobis(2-methylpropionate) (polymerization initiator) to a monomer mixture consisting of 115.2 parts of 2-ethylhexyl acrylate, 86.0 parts of glycidyl methacrylate, 72.7 parts of methyl methacrylate, and 13.3 parts of dicyclopentanyl methacrylate was added dropwise to the above flask from the dropping funnel over 2 hours. After the addition was completed, stirring was continued at 100 °C for 30 minutes for copolymerization reaction.

[0389] Then, the inside of the flask was replaced with air, 43.8 parts of acrylic acid, 1.0 part of triphenylphosphine (catalyst), and 1.0 part of dibutylhydroxytoluene (polymerization inhibitor) were added, and the reaction was continued at 120 °C for 10 hours. Next, 22.1 parts of succinic anhydride was added to the reaction system, and the reaction was further continued for 1.5 hours to obtain a polymer.

[0390] Finally, 330 parts of propylene glycol monomethyl ether was added to the reaction solution, and then propylene glycol monomethyl ether acetate was added in such a manner that the polymer solid content concentration became 40%, to obtain a polymer (resin (B-7)) solution.

[0391] <Synthesis Example 13: Preparation of Resin (B-8)>

[0392] 349 parts of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, and the mixture was stirred while purging with nitrogen and heated to 120°C.

[0393] Next, a substance obtained by adding 23.4 parts of tert-butyl peroxy-2-ethylhexanoate to a monomer mixture composed of 169.2 parts of benzyl methacrylate, 103.3 parts of methacrylic acid, and 52.9 parts of dicyclopentanyl methacrylate was added dropwise from the dropping funnel to the above flask over 2 hours. After the addition was completed, the mixture was further stirred for 30 minutes to carry out a copolymerization reaction.

[0394] Then, the inside of the flask was replaced with air, 51.2 parts of glycidyl methacrylate, 1.1 parts of triphenylphosphine, and 1.1 parts of methyl quinone were added, and the reaction was continued at 120°C for 10 hours to obtain a polymer. Finally, propylene glycol monomethyl ether acetate was added to the reaction solution in such a manner that the polymer solid content concentration became 40%, to obtain a polymer (resin (B-8)) solution. The vinyl double bond equivalent of resin (B-8) is 1100 g / mol.

[0395] <Synthesis Example 14: Preparation of Resin (B-9)>

[0396] 492.4 parts of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, and the mixture was stirred while purging with nitrogen and heated to 90°C.

[0397] Next, a substance obtained by adding 32.6 parts of dimethyl 2,2'-azobis(2-methylpropionate) and 5.7 parts of mercaptoacetic acid to a monomer mixture composed of 208.1 parts of vinyltoluene, 62.1 parts of acrylic acid, and 13.0 parts of norbornene was added dropwise from the dropping funnel to the above flask over 2 hours. After the addition was completed, the mixture was further stirred for 30 minutes to carry out a copolymerization reaction.

[0398] Then, the inside of the flask was replaced with air, 78.5 parts of glycidyl methacrylate, 1.1 parts of triphenylphosphine, and 1.1 parts of methyl quinone were added, and the reaction was continued at 120°C for 10 hours to obtain a polymer. Finally, propylene glycol monomethyl ether acetate was added to the reaction solution in such a manner that the polymer solid content concentration became 40%, to obtain a polymer (resin (B-9)) solution. The vinyl double bond equivalent of resin (B-9) is 730 g / mol.

[0399] <Synthesis Example 15: Preparation of Resin (B-10)>

[0400] 547 parts of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, and the mixture was stirred while purging with nitrogen and heated to 120°C.

[0401] Next, a substance obtained by adding 4.2 parts of tert-butyl peroxy-2-ethylhexanoate to a monomer mixture composed of 272.0 parts of benzyl methacrylate and 73.8 parts of methacrylic acid was added dropwise from the dropping funnel to the above flask over 2 hours. After the addition was completed, the mixture was further stirred for 30 minutes for copolymerization reaction to obtain a polymer. Propylene glycol monomethyl ether acetate was added to the reaction solution so that the polymer solid content concentration became 35%, and a solution of the polymer (resin (B-10)) was obtained.

[0402] <Synthesis Example 16: Preparation of Resin (B-11)>

[0403] An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 340 parts of propylene glycol monomethyl ether acetate was added. The mixture was heated to 80°C while stirring. Next, a mixed solution of 57 parts of acrylic acid, a mixture of 3,4-epoxytricyclo[5.2.1.0 2，6 decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2 ，6 decane-9-yl acrylate (containing a molar ratio of 1:1) 54 parts, 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution obtained by dissolving 40 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition of the initiator solution was completed, the mixture was maintained at 80°C for 3 hours and then cooled to room temperature to obtain a copolymer (resin (B-11)) solution having a viscosity of 127 mPas measured by a B-type viscometer (23°C) and a solid content of 37.0% by weight. The weight average molecular weight Mw of the resulting resin (B-11) was 9.4×10 3 , the dispersity was 1.89, and the acid value in terms of solid content was 114 mg-KOH / g. Resin (B-11) has the following structural units.

[0404]

[0405] <Synthesis Example 17: Preparation of Resin (B-12)>

[0406] An appropriate amount of nitrogen was introduced into a 1 L flask equipped with a reflux condenser, a dropping funnel, and a stirrer to displace the atmosphere with nitrogen, and 256 parts of propylene glycol monomethyl ether acetate was added. The mixture was heated to 80 °C while stirring. Next, a mixed solution of 44 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2，6 decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2，6 decane-9-yl acrylate, 57 parts of acrylic acid, 249 parts of 3-phenoxybenzyl acrylate, and 159 parts of propylene glycol monomethyl ether acetate was added dropwise over 3 hours.

[0407] On the other hand, a mixed solution of 25 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 210 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the addition was completed, the mixture was maintained at this temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B-12)) solution having a B-type viscosity (23 °C) of 51 mPas and a solid content of 36.0%. The weight-average molecular weight Mw of the resulting copolymer was 11,000, and the dispersity was 1.98.

[0408] The weight-average molecular weight Mw and number-average molecular weight Mn of the resin obtained in the above synthesis example in terms of polystyrene were measured by the GPC method under the following conditions.

[0409] Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)

[0410] Column: TSK-GEL G2000HXL

[0411] Column temperature: 40 °C

[0412] Solvent: Tetrahydrofuran

[0413] Flow rate: 1.0 mL / min

[0414] Concentration of solid content in the test solution: 0.001 to 0.01 mass%

[0415] Injection volume: 50 μL

[0416] Detector: RI

[0417] Standard substance for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0418] The ratio (Mw / Mn) of the weight-average molecular weight to the number-average molecular weight in terms of polystyrene obtained above was used as the dispersity.

[0419] <Examples 1 and Comparative Example 1>

[0420] (1) Preparation of Coloring Curable Resin Composition

[0421] The coloring curable resin composition is obtained by mixing the respective components described in Table 1 in such a manner that the blending amounts described in Table 1 are achieved. It should be noted that when preparing the coloring curable resin composition, propylene glycol monomethyl ether acetate is mixed in such a manner that the solid content of the coloring curable resin composition becomes 23.5% by mass. The unit of the blending amount of each component in Table 1 is "parts by mass", and the blending amounts of the colorant (A), resin (B), polymerizable compound (C), polymerization initiator (D), silane coupling agent, and leveling agent (F) are in terms of solid content conversion.

[0422] The colorant (A), resin (B), polymerizable compound (C), polymerization initiator (D), silane coupling agent as an adhesion promoter, and leveling agent (F) used are as follows.

[0423] Colorant (A): Coloring dispersion liquid (A - 1) (shown as the total amount of each pigment in Table 1)

[0424] Resin (B): Resin (B - 1)

[0425] Polymerizable compound (C): Polymerizable compound (C - 1) (manufactured by Shin-Nakamura Chemical Co., Ltd., trade name "NKEster A - TMPT", trimethylolpropane triacrylate)

[0426]

[0427] Polymerization initiator (D): Polymerization initiator (D - 1) The compound represented by the following formula (manufactured by BASF Co., Ltd., trade name "Irgacure OXE03")

[0428]

[0429] Polymerization initiator (D): Polymerization initiator (D - 2) The compound represented by the following formula

[0430]

[0431] Silane coupling agent: The compound represented by the following formula, 3 - methacryloyloxypropyltrimethoxysilane (trade name "KBM - 503" manufactured by Shin-Etsu Chemical Co., Ltd.)

[0432]

[0433] Leveling agent (F): Polyether-modified silicone oil (trade name "Toray Silicone SH8400" manufactured by Dow Corning Toray Co., Ltd.)

[0434] [Table 1]

[0435]

[0436] (The acrylic pigment dispersant and dispersion resin in Table 1 are expressed as the amounts from the colored dispersion liquid (A-1).)

[0437] 〔Fabrication of Pattern 1〕

[0438] After each colored curable resin composition described in Table 1 was spin-coated onto a 4-inch glass wafer so that the post-baked film thickness became 1.2 μm, a colored composition layer was obtained. Using an exposure machine (NSR-1755i7A; manufactured by Nikon Corporation), light was irradiated onto the substrate having the colored composition layer at an exposure amount of 200 mJ / cm 2 (based on 365 nm). As the photomask, a photomask having a 2.0 μm square dot pattern formed thereon was used. The colored composition layer after light irradiation was immersed and developed in an aqueous developing solution containing tetramethylammonium hydroxide at 23°C for 20 seconds. After washing with water, post-baking was performed at 90°C for 15 minutes, thereby obtaining a pattern. The film thickness of the obtained pattern was measured using a film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Technology Co., Ltd.), and the result was confirmed to be 1.2 μm.)

[0439] <Example 2 and Comparative Example 2>

[0440] (1) Preparation of Colored Curable Resin Composition

[0441] The respective components described in Table 2 were mixed so as to have the blending amounts described in Table 2, thereby obtaining a colored curable resin composition. It should be noted that when preparing the colored curable resin composition, propylene glycol monomethyl ether acetate was mixed so that the solid content of the colored curable resin composition became 14.0%. The unit of the blending amount of each component in Table 2 is "parts by mass", and the blending amounts of the colorant (A), resin (B), polymerizable compound (C), polymerization initiator (D), and leveling agent (F) are in terms of solid content conversion.)

[0442] The colorant (A), resin (B), polymerizable compound (C), polymerization initiator (D), and leveling agent (F) used are as follows.)

[0443] Colorant (A): Colored dispersion liquid (A-2) (expressed as the total amount of each pigment in Table 2)

[0444] Resin (B): Resin (B-2)

[0445] Polymerizable compound (C): Polymerizable compound (C-2) (manufactured by Toagosei Co., Ltd., trade name "ARONIX (registered trademark) M-930", glycerol triacrylate)

[0446]

[0447] Polymerization initiator (D): Polymerization initiator (D-1) A compound represented by the following formula (manufactured by BASF Corporation, trade name "Irgacure OXE03")

[0448]

[0449] Polymerization initiator (D): Polymerization initiator (D-2) A compound represented by the following formula

[0450]

[0451] Leveling agent (F): Polyether-modified silicone oil (trade name "Toray Silicone SH8400" manufactured by Dow Corning Toray Co., Ltd.)

[0452] [Table 2]

[0453]

[0454] (The acrylic pigment dispersant and dispersion resin in Table 2 are expressed as the amounts from the colored dispersion liquid (A-2).)

[0455] [Fabrication of Pattern 2]

[0456] Each of the colored curable resin compositions described in Table 2 was spin-coated on a 2-inch square glass substrate (EAGLE XG; manufactured by Corning Incorporated) so that the post-baked film thickness became 2.0 μm, and then pre-baked at 70°C for 2 minutes to form a composition layer. After cooling, the distance between the substrate with the composition layer formed thereon and a quartz glass photomask was set to 50 μm, and light irradiation was performed at an exposure dose of 100 mJ / cm 2 (based on 365 nm) in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by TOPCON Corporation). Incidentally, as the photomask, a mask having a 10-μm line and space pattern formed thereon was used. The composition layer after light irradiation was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25°C for 60 seconds for development, washed with water, and then post-baked in an oven at 85°C for 30 minutes to obtain a pattern. The film thickness of the obtained pattern was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.), and the result was confirmed to be 2.0 μm.

[0457] [Evaluation of Solvent Resistance]

[0458] The patterns obtained from Pattern Production 1 and Pattern Production 2 were immersed in propylene glycol monomethyl ether acetate (PGMEA) or propylene glycol monomethyl ether (PGME) at a temperature of 23°C for 5 minutes, and then rinsed with running water for 10 seconds for the solvent resistance test. A colorimeter (OSP-SP-200; manufactured by Olympus Corporation) was used to measure the spectrum, and evaluation based on color difference and measurement of the film thickness retention rate (film thickness change) before and after the solvent resistance test were performed. It should be noted that the film thickness retention rate (film thickness change) refers to the ratio of the film thickness after immersion to the film thickness before immersion. The results are shown in Tables 3 to 4.

[0459] [Table 3]

[0460]

[0461] [Table 4]

[0462]

[0463] <Example 3 and Comparative Example 3>

[0464] (1) Preparation of the colored curable resin composition

[0465] The respective components were mixed in such amounts as to be the amounts shown in Table 5 to obtain the colored curable resin composition. It should be noted that when preparing the colored curable resin composition, propylene glycol monomethyl ether acetate was mixed so that the solid content of the colored curable resin composition became 14.0%. The unit of the amounts of the respective components in Table 5 is "parts by mass", and the amounts of the colorant (A), resin (B), polymerizable compound (C), polymerization initiator (D), and leveling agent (F) are in terms of solid content conversion.

[0466] [Table 5]

[0467]

[0468] The components (A-3), (B-X), (B-1), (C-1), (D-1), and (D-2) are the same as above, and as the leveling agent (F), polyether-modified silicone oil (trade name "Toray Silicone SH8400" manufactured by Dow Corning Toray Co., Ltd.) was used. (The acrylic pigment dispersant and dispersion resin in Table 5 are shown as the amounts from the colored dispersion liquid (A-3).)

[0469] 〔Pattern Production 3〕

[0470] After each colored curable resin composition described in Table 5 was applied onto a 2-inch square glass substrate (EAGLE XG; manufactured by Corning Incorporated) by spin coating so that the film thickness after post-baking became 2.0 μm, it was pre-baked at 70°C for 2 minutes to form a composition layer. After cooling, the distance between the substrate with the composition layer formed thereon and a quartz glass photomask was set to 50 μm, and light irradiation was performed using an exposure machine (TME-150RSK; manufactured by TOPCON CORPORATION) in an atmospheric atmosphere at an exposure dose of 100 mJ / cm 2 (based on 365 nm). Note that as the photomask, a mask having a 10-μm line and space pattern formed thereon was used. The composition layer after light irradiation was immersed and developed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25°C for 60 seconds, washed with water, and then post-baked in an oven at 85°C for 30 minutes to obtain a pattern. The film thickness of the obtained pattern was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.), and as a result, it was confirmed to be 2.0 μm.

[0471] [Evaluation of Solvent Resistance]

[0472] The pattern obtained in Pattern Formation 3 was immersed in propylene glycol monomethyl ether acetate (PGMEA) or propylene glycol monomethyl ether (PGME) at a temperature of 23°C for 5 minutes, and a solvent resistance test was performed by rinsing with running water for 10 seconds. A colorimeter (OSP-SP-200; manufactured by Olympus Corporation) was used to measure the spectrum, and evaluation based on color difference and measurement of the film thickness retention rate (film thickness change) before and after the solvent resistance test were performed. Note that the film thickness retention rate (film thickness change) refers to the ratio of the film thickness after immersion to the film thickness before immersion. The results are shown in Table 6.

[0473] [Table 6]

[0474]

[0475] <Test Examples 1 to 11>

[0476] (1) Preparation of Colored Curable Resin Composition

[0477] Each component was mixed in the amounts shown in Table 7 to obtain a colored curable resin composition. Note that when preparing the colored curable resin composition, propylene glycol monomethyl ether acetate was mixed so that the solid content of the colored curable resin composition became 14.0%. The unit of the amount of each component in Table 7 is "parts by mass", and the amounts of the colorant (A), resin (B), polymerizable compound (C), polymerization initiator (D), and leveling agent (F) are in terms of solid content conversion.

[0478] [Table 7]

[0479]

[0480] For (A-4), (B-X), (B-1), (B-3) to (B-12), (C-1), and (D-2) of each component, they are the same as above. As the leveling agent (F), polyether-modified silicone oil (trade name "Toray Silicone SH8400" manufactured by Dow Corning Toray Co., Ltd.) is used. (The acrylic pigment dispersant and dispersion resin in Table 7 are expressed as the amount from the colored dispersion liquid (A-4).)

[0481] [Fabrication of Pattern 4]

[0482] After each colored curable resin composition described in Table 7 was spin-coated on a 2-inch square glass substrate (EAGLE XG; manufactured by Corning Inc.) so that the post-baked film thickness became 2.0 μm, it was pre-baked at 70°C for 2 minutes to form a composition layer. After cooling, the distance between the substrate with the composition layer formed and a quartz glass photomask was set to 50 μm, and using an exposure machine (TME-150RSK; manufactured by TOPCON Corp.), light irradiation was performed in an atmospheric atmosphere with an exposure amount of 100 mJ / cm 2 (based on 365 nm standard). It should be noted that as the photomask, a mask with a 10-μm line and space pattern was used. The composition layer after light irradiation was immersed and developed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25°C for 60 seconds, washed with water, and then post-baked in an oven at 85°C for 30 minutes to obtain a pattern. The film thickness of the obtained pattern was measured using a film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Technology Co., Ltd.), and the result was confirmed to be 2.0 μm.

[0483] [Evaluation of Solvent Resistance]

[0484] The pattern obtained from Pattern Fabrication 4 was immersed in propylene glycol monomethyl ether acetate (PGMEA) or propylene glycol monomethyl ether (PGME) at a temperature of 23°C for 5 minutes, and subjected to a solvent resistance test by flushing with running water for 10 seconds. A colorimeter (OSP-SP-200; manufactured by Olympus Corp.) was used to measure the spectrum, and evaluation based on color difference and measurement of the film thickness retention rate (film thickness change) before and after the solvent resistance test were performed. It should be noted that the film thickness retention rate (film thickness change) refers to the ratio of the film thickness after immersion to the film thickness before immersion. The results are shown in Table 8.

[0485] [Table 8]

[0486]

Claims

1. A colored curable resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator, wherein the polymerization initiator comprises a compound represented by formula (I), In the formula, R 1 , R 2 , R 3 , R 4 and R 5 Each independently represents a hydrocarbon group which may have a substituent, n represents any integer from 0 to 4, The -CH 2 - contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -OCO-.

2. The colored curable resin composition according to claim 1, wherein, the resin is at least one selected from the following resins [K1] to [K6], Resin [K1]: A copolymer having a structural unit derived from at least one monomer (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides and a structural unit derived from a monomer (b) having a cyclic ether structure and an ethylenic unsaturated bond with 2 to 4 carbon atoms; Resin [K2]: A copolymer having a structural unit derived from the monomer (a), a structural unit derived from the monomer (b), and a structural unit derived from a monomer (c) copolymerizable with the monomer (a); Resin [K3]: A copolymer having a structural unit derived from the monomer (a) and a structural unit derived from the monomer (c); Resin [K4]: A copolymer having a structural unit obtained by adding the monomer (b) to a structural unit derived from the monomer (a) and a structural unit derived from the monomer (c); Resin [K5]: A copolymer having a structural unit obtained by adding the monomer (a) to a structural unit derived from the monomer (b) and a structural unit derived from the monomer (c); Resin [K5']: A copolymer having a structural unit obtained by adding the monomer (b) to a structural unit derived from the monomer (a) and a structural unit derived from the monomer (c); Resin [K6]: A copolymer having a structural unit obtained by adding the monomer (a) to a structural unit derived from the monomer (b) and further adding a carboxylic anhydride and a structural unit derived from the monomer (c).

3. The colored curable resin composition according to claim 2, wherein, the resin is resin [K1] and / or resin [K2].

4. The colored curable resin composition according to claim 2, wherein, the resin is any one of resins [K2] to [K6], and is a resin containing at least one selected from (meth)acrylates having a linear or branched aliphatic unsaturated hydrocarbon group, (meth)acrylates having a cyclic unsaturated aliphatic hydrocarbon group, vinyl monomers having an unsaturated aliphatic hydrocarbon ring, vinyl monomers having an unsaturated heterocycle, and vinyl monomers having an aromatic ring as the monomer (c).

5. The colored curable resin composition according to claim 2, wherein, the resin is any one of resins [K4] to [K6].

6. The colored curable resin composition according to claim 2, wherein, the resin has an ethylenic double bond, and the ethylenic double bond equivalent of the resin is 100 to 2000 g / mol.

7. The colored curable resin composition according to claim 2, wherein, The resin is any one of resins [K2] to [K4], and contains (meth)acrylate having an aromatic ring as the monomer (c). In 100 mol% of all structural units, the total of the structural units derived from (meth)acrylate having an aromatic ring and the structural units derived from the (a) is 60 mol% or more.

8. The colored curable resin composition according to claim 2, wherein the colorant contains a green pigment and a yellow pigment, the green pigment contains at least one selected from C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment Green 58, C.I. Pigment Green 59, C.I. Pigment Green 62, and C.I. Pigment Green 63, the yellow pigment contains at least one selected from C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 185, C.I. Pigment Yellow 231, and C.I. Pigment Yellow 233.

9. The colored curable resin composition according to claim 2, wherein the colorant contains a red pigment and a yellow pigment, the red pigment contains at least one selected from C.I. Pigment Red 122, C.I. Pigment Red 177, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264, C.I. Pigment Red 269, C.I. Pigment Red 272, and C.I. Pigment Red 291, the yellow pigment contains at least one selected from C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 185, C.I. Pigment Yellow 231, and C.I. Pigment Yellow 233.

10. The colored curable resin composition according to claim 2, wherein the colorant contains a blue pigment and a purple pigment, the blue pigment contains at least one selected from C.I. Pigment Blue 15, 15:3, 15:4, 15:6, and 16, the purple pigment contains at least one selected from C.I. Pigment Violet 19, 23, and 29.

11. A color filter formed from the colored curable resin composition according to any one of claims 1 to 10.

12. A display device comprising the color filter according to claim 11.

13. A solid-state imaging device comprising the color filter according to claim 11.

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