JP2024069149A - Colored curable resin composition, color filter, display device, and solid-state imaging element - Google Patents

Abstract

To provide a colored curable resin composition with which it is possible to form a color filter with improved solvent resistance.SOLUTION: The present invention relates to a colored curable resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, the polymerization initiator including a compound expressed by formula (I). (In the formula, R1, R2, R3, R4, and R5 each independently represent a hydrocarbon group, which optionally may have a substituent. n represents an integer of 0 to 4. -CH2- included in the hydrocarbon group may be substituted with -O-, -S-, -CO-, or -OCO-).SELECTED DRAWING: None

Description

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

Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored curable resin compositions. It is known that a specific polymerization initiator is used in this colored curable resin composition (Patent Document 1).

International Publication No. 2021/175855

The objective of the present invention is to provide a colored curable resin composition that can form a color filter with improved solvent resistance.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴及びＲ⁵は、それぞれ独立して、置換基を有していてもよい炭化水素基を表す。
ｎは０～４のいずれかの整数を表す。
前記炭化水素基に含まれる－ＣＨ₂－は－Ｏ－、－Ｓ－、－ＣＯ－、又は－ＯＣＯ－に置き換わっていてもよい。）
［２］前記樹脂が、下記樹脂［Ｋ１］から［Ｋ６］から選ばれる少なくとも１つである、［１］に記載の着色硬化性樹脂組成物。
樹脂［Ｋ１］；不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも１種の単量体（ａ）に由来する構造単位と、炭素数２～４の環状エーテル構造とエチレン性不飽和結合とを有する単量体（ｂ）に由来する構造単位とを有する共重合体；
樹脂［Ｋ２］；前記（ａ）に由来する構造単位と前記（ｂ）に由来する構造単位と、前記（ａ）と共重合可能な単量体（ｃ）に由来する構造単位とを有する共重合体；
樹脂［Ｋ３］；前記（ａ）に由来する構造単位と前記（ｃ）に由来する構造単位とを有する共重合体；
樹脂［Ｋ４］；前記（ａ）に由来する構造単位に前記（ｂ）を付加させた構造単位と前記（ｃ）に由来する構造単位とを有する共重合体；
樹脂［Ｋ５］；前記（ｂ）に由来する構造単位に前記（ａ）を付加させた構造単位と前記（ｃ）に由来する構造単位とを有する共重合体；
樹脂［Ｋ５’］；前記（ａ）に由来する構造単位に前記（ｂ）を付加させた構造単位と前記（ｃ）に由来する構造単位とを有する共重合体；
樹脂［Ｋ６］；前記（ｂ）に由来する構造単位に前記（ａ）を付加させ、カルボン酸無水物をさらに付加させた構造単位と前記（ｃ）に由来する構造単位とを有する共重合体。［３］前記樹脂が樹脂［Ｋ１］及び／又は樹脂［Ｋ２］である［２］に記載の着色硬化性樹脂組成物。
［４］前記樹脂が樹脂[Ｋ２］～［Ｋ６］のいずれかであって前記単量体（ｃ）として直鎖又は分岐鎖の脂肪族不飽和炭化水素基を有する（メタ）アクリル酸エステル類、環状不飽和脂肪族炭化水素基を有する（メタ）アクリル酸エステル類、不飽和脂肪族炭化水素環を有するビニルモノマー、不飽和複素環を有するビニルモノマー、及び芳香族環を有するビニルモノマーから選ばれる少なくとも１種を含有する樹脂である［２］に記載の着色硬化性樹脂組成物。
［５］前記樹脂が樹脂［Ｋ４］～［Ｋ６］のいずれかである［２］に記載の着色硬化性樹脂組成物。
［６］前記樹脂がエチレン性二重結合を有し、前記樹脂のエチレン性二重結合当量が１００～２０００ｇ／ｍｏｌである[２]に記載の着色硬化性樹脂組成物。
［７］前記樹脂が樹脂［Ｋ２］～［Ｋ４］のいずれかであって、前記単量体（ｃ）として芳香族環を有する（メタ）アクリル酸エステル類を含み、全構造単位１００モル％中、芳香族環を有する（メタ）アクリル酸エステル類由来の構造単位と前記（ａ）に由来する構造単位の合計が６０モル％以上である［２］に記載の着色硬化性樹脂組成物。
［８］着色剤が、緑色顔料及び黄色顔料を含み、
前記緑色顔料は、Ｃ．Ｉ．ピグメントグリーン７、Ｃ．Ｉ．ピグメントグリーン３６、Ｃ．Ｉ．ピグメントグリーン５８、Ｃ．Ｉ．ピグメントグリーン５９、Ｃ．Ｉ．ピグメントグリーン６２、及びＣ．Ｉ．ピグメントグリーン６３からなる群から選ばれる少なくとも１種を含み、
前記黄色顔料は、Ｃ．Ｉ．ピグメントイエロー１３８、Ｃ．Ｉ．ピグメントイエロー１３９、Ｃ．Ｉ．ピグメントイエロー１５０、Ｃ．Ｉ．ピグメントイエロー１８５、Ｃ．Ｉ．ピグメントイエロー２３１、及びＣ．Ｉ．ピグメントイエロー２３３からなる群から選ばれる少なくとも１種を含む［２］に記載の着色硬化性樹脂組成物。
［９］着色剤が、赤色顔料及び黄色顔料を含み、
前記赤色顔料は、Ｃ．Ｉ．ピグメントレッド１２２、Ｃ．Ｉ．ピグメントレッド１７７、Ｃ．Ｉ．ピグメントレッド２５４、Ｃ．Ｉ．ピグメントレッド２５５、Ｃ．Ｉ．ピグメントレッド２６４、Ｃ．Ｉ．ピグメントレッド２６９、Ｃ．Ｉ．ピグメントレッド２７２、及びＣ．Ｉ．ピグメントレッド２９１からなる群から選ばれる少なくとも１種を含み、
前記黄色顔料は、Ｃ．Ｉ．ピグメントイエロー１３８、Ｃ．Ｉ．ピグメントイエロー１３９、Ｃ．Ｉ．ピグメントイエロー１５０、Ｃ．Ｉ．ピグメントイエロー１８５、Ｃ．Ｉ．ピグメントイエロー２３１、及びＣ．Ｉ．ピグメントイエロー２３３からなる群から選ばれる少なくとも１種を含む［２］に記載の着色硬化性樹脂組成物。
［１０］着色剤が、青色顔料及び紫色顔料を含み、
前記青色顔料は、Ｃ．Ｉ．ピグメントブルー１５、１５：３、１５：４、１５：６、１６からなる群より選ばれる少なくとも１種を含み、
前記紫色顔料は、Ｃ．Ｉ．ピグメントバイオレット１９、２３、２９からなる群より選ばれる少なくとも１種を含む[２]に記載の着色硬化性樹脂組成物。
［１１］［１］～［１０］のいずれかに記載の着色硬化性樹脂組成物から形成されるカラーフィルタ。
［１２］［１１］に記載のカラーフィルタを含む表示装置。
［１３］［１１］に記載のカラーフィルタを含む固体撮像素子。 That is, the gist of the present invention is as follows.
[1] A composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator;
The colored curable resin composition, 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 represent a hydrocarbon group which may have a substituent.
n represents an integer of 0 to 4.
The --CH ₂ -- contained in the hydrocarbon group may be replaced with --O--, --S--, --CO--, or --OCO--.
[2] The colored curable resin composition according to [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 the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond;
Resin [K2]: a copolymer having a structural unit derived from the (a), a structural unit derived from the (b), and a structural unit derived from a monomer (c) copolymerizable with the (a);
Resin [K3]: a copolymer having a structural unit derived from the (a) and a structural unit derived from the (c);
Resin [K4]: a copolymer having a structural unit derived from the (a) and a structural unit derived from the (b) and a structural unit derived from the (c);
Resin [K5]: a copolymer having a structural unit derived from the (b) to which the (a) has been added, and a structural unit derived from the (c);
Resin [K5']: a copolymer having a structural unit derived from the (a) and a structural unit derived from the (b) by addition, and a structural unit derived from the (c);
Resin [K6]: A copolymer having a structural unit obtained by adding the (a) to a structural unit derived from the (b) and further adding a carboxylic acid anhydride, and a structural unit derived from the (c). [3] The colored curable resin composition according to [2], wherein the resin is resin [K1] and/or resin [K2].
[4] The colored curable resin composition according to [2], wherein the resin is any one of resins [K2] to [K6], and the monomer (c) is at least one selected from the group consisting of (meth)acrylic acid esters having a linear or branched aliphatic unsaturated hydrocarbon group, (meth)acrylic acid esters 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.
[5] The colored curable resin composition according to [2], wherein the resin is any one of resins [K4] to [K6].
[6] The colored curable resin composition according to [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 [2], wherein the resin is any one of resins [K2] to [K4], the monomer (c) contains a (meth)acrylic acid ester having an aromatic ring, and the total of the structural units derived from the (meth)acrylic acid ester having an aromatic ring and the structural units derived from the (a) is 60 mol % or more in 100 mol % of all structural units.
[8] The colorant includes a green pigment and a yellow pigment,
The green pigment includes at least one selected from the group consisting of 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 includes at least one selected from the group consisting of 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. The colored curable resin composition according to [2].
[9] The colorant includes a red pigment and a yellow pigment,
The red pigment includes at least one selected from the group consisting of 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 includes at least one selected from the group consisting of 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. The colored curable resin composition according to [2].
[10] The colorant includes a blue pigment and a purple pigment,
The blue pigment includes at least one selected from the group consisting of C.I. Pigment Blue 15, 15:3, 15:4, 15:6, and 16;
The colored curable resin composition according to [2], wherein the purple pigment includes at least one selected from the group consisting of C.I. Pigment Violet 19, 23, and 29.
[11] A color filter formed from the colored curable resin composition according to any one of [1] to [10].
[12] A display device comprising the color filter according to [11].
[13] A solid-state imaging device comprising the color filter according to [11].

The present invention makes it possible to provide a colored curable resin composition that can form a color filter with improved solvent resistance.

The colored curable resin composition of the present invention contains a colorant (hereinafter, may be referred to as colorant (A)), a resin (hereinafter, may be referred to as resin (B)), a polymerizable compound (hereinafter, may be referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter, may be referred to as polymerization initiator (D)).
The colored curable resin composition of the present invention may further contain a solvent (hereinafter, may be referred to as solvent (E)).
The colored curable resin composition of the present invention may further contain a polymerization initiation aid (hereinafter, may be referred to as polymerization initiation aid (D1)).
The colored curable resin composition of the present invention may further contain a thiol compound (hereinafter, may be referred to as thiol compound (T)).
The colored curable resin composition of the present invention may further contain a leveling agent (hereinafter, may be referred to as leveling agent (F)).
In this specification, the compounds exemplified as each component may be used alone or in combination of two or more kinds, unless otherwise specified.

<Colorant (A)>
The colorant (A) may be a dye (A1) or a pigment (A2), and the pigment (A2) is preferred. These may be used alone or in combination of two or more.

The dye (A1) is not particularly limited, and known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used according to their chemical structure include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, and isoindoline dyes. Of these, organic solvent-soluble dyes are preferred.

Specifically, dyes having the following Color Index (C.I.) numbers are included.
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;
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;
C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;
C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
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;
C.I. Solvent dyes such as C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35;
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, 1 57, 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;
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, 18 2, 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;
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;
C.I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;
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;
C. I. Acid dyes such as 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;
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;
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;
C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
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;
C.I. Direct dyes such as C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82;
C.I. Disperse Yellow 51, 54, 76;
C.I. Disperse Violet 26, 27;
C.I. Disperse dyes such as C.I. Disperse Blue 1, 14, 56, 6;0,
C.I. Basic Red 1, 10;
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;
C.I. Basic Violet 2;
C.I. Basic Red 9;
C.I. Basic dyes such as C.I. Basic Green 1;
C.I. Reactive Yellow 2, 76, 116;
C.I. Reactive Orange 16;
C.I. Reactive dyes such as C.I. Reactive Red 36;
C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
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;
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;
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;
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;
C.I. Mordant dyes such as C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53;
C.I. Vat dyes such as C.I. Vat Green 1;

These dyes can be selected appropriately to match the optical spectrum of the desired color filter.

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). In addition, according to the chemical structure, azo pigments, cyanine pigments, triphenylmethane pigments, xanthene pigments, anthraquinone pigments, naphthoquinone pigments, quinoneimine pigments, methine pigments, azomethine pigments, squarylium pigments, acridine pigments, styryl pigments, coumarin pigments, quinoline pigments, nitro pigments, phthalocyanine pigments, perylene pigments, quinophthalone pigments, isoindoline pigments, etc. are listed. Of these, phthalocyanine pigments, quinophthalone pigments, isoindoline pigments, etc. are preferred.

Specific examples of pigments classified as C.I. Pigment include yellow pigments such as C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231;
Orange pigments such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
red pigments such as 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;
blue pigments such as C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60;
Violet pigments such as C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38;
green pigments such as C.I. Pigment Green 7, 36, 58, 59, 62, 63;
Brown pigments such as C.I. Pigment Brown 23 and 25;
black pigments such as C.I. Pigment Black 1, 7, 31, and 32;

These pigments can be selected appropriately to match the desired color filter spectrum.

When preparing a green colored curable resin composition, the colorant (A) preferably contains at least one selected from the group consisting of a yellow dye and a yellow pigment (hereinafter, these may be collectively referred to as "yellow colorant"), a green dye and a green pigment (hereinafter, these may be collectively referred to as "green colorant"), and more preferably contains a yellow pigment and/or a green pigment.

The yellow dye may be any of the above dyes whose hues are classified as yellow, and the yellow pigment may be any of the above pigments whose hues are classified as yellow.
Among the yellow pigments, quinophthalone yellow pigments, metal-containing yellow pigments, and isoindoline yellow pigments are preferred, and at least one selected from the group consisting of C.I. Pigment Yellow 138, 139, 150, 185, 231, and 233 is more preferred, and at least one selected from the group consisting of C.I. Pigment Yellow 138, 139, 150, and 185 is even more preferred.

The green dye may be any of the above dyes whose hue is classified as green, and the green pigment may be any of the above pigments whose hue is classified as green.
Among the green pigments, phthalocyanine pigments are preferred, at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferred, at least one selected from the group consisting of C.I. Pigment Green 7, 36, 58, 59, 62, and 63 is even more preferred, and at least one selected from the group consisting of C.I. Pigment Green 58 and 59 is even more preferred.

In the case of preparing a green colored curable resin composition, the colorant (A) preferably contains a yellow colorant and/or a green colorant in total in an amount of, for example, 50 mass% or more, preferably 70 mass% or more, more preferably 90 mass% or more, and particularly preferably 95 mass% or more, based on 100 mass% of all colorants.
In addition, it is preferable that both a yellow colorant and a green colorant are contained. In the case where both a yellow colorant and a green colorant are contained, the content of the yellow colorant is, for example, 10 mass% or more and 70 mass% or less, preferably 15 mass% or more and 60 mass% or less, and more preferably 20 mass% or more and 55 mass% or less, based on 100 mass% in total of the yellow colorant and the green colorant.
In the case where both a yellow colorant and a green colorant are contained, the content of the green colorant is, for example, 30% by mass or more and 90% by mass or less, preferably 40% by mass or more and 85% by mass or less, and more preferably 45% by mass or more and 80% by mass or less, based on 100% by mass of the total of the yellow colorant and the green colorant.

The green colored curable resin composition may contain a blue colorant, which will be described later, in addition to a green colorant and a yellow colorant.
The content of the blue colorant is, for example, 0 mass% or more and 5 mass% or less, preferably 0.1 mass% or more and 4.5 mass% or less, and more preferably 0.2 mass% or more and 4.0 mass% or less, relative to 100 mass% in total of the green colorant, the yellow colorant, and the blue colorant.

When preparing a red colored curable resin composition, the colorant (A) preferably contains at least one selected from the group consisting of a yellow colorant, a red dye, and a red pigment (hereinafter, these may be collectively referred to as "red colorant"), and more preferably contains a yellow pigment and/or a red pigment.

Examples of yellow colorants include the same as those used to prepare the green colored curable resin composition, and the preferred embodiments are also the same.

The red dye may be any of the above dyes whose hue is classified as red, and the red pigment may be any of the above pigments whose hue is classified as red.
Among the red pigments, at least one selected from the group consisting of C.I. Pigment Red 122, 177, 254, 255, 264, 269, 272, and 291 is preferable, and at least one selected from the group consisting of C.I. Pigment Red 177, 254, 269, 272, and 291 is more preferable.

When preparing a red 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 especially 100% by mass of a yellow colorant and/or a red colorant in total, based on 100% by mass of all colorants. It is also preferable that the colorant (A) contains both a yellow colorant and a red colorant.

When preparing a blue colored curable resin composition, the colorant (A) preferably contains at least one selected from the group consisting of a blue dye and a blue pigment (hereinafter, these may be collectively referred to as "blue colorant"), and more preferably contains a blue pigment.

Examples of blue dyes include those dyes that have a hue classified as blue among the above dyes, and examples of blue pigments include those pigments that have a hue classified as blue among the above pigments.
As the blue pigment, a phthalocyanine pigment is preferable, and at least one selected from the group consisting of C.I. Pigment Blue 15, 15:3, 15:4, 15:6, and 16 is more preferable.

When preparing a blue colored curable resin composition, it is preferable to also contain a violet dye and a violet pigment (hereinafter, these may be collectively referred to as "violet colorant") in addition to the blue colorant.

The violet dye may be any of the above dyes whose hues are classified as violet, and the violet pigment may be any of the above pigments whose hues are classified as violet.
As the violet colorant, a violet pigment is preferable, and among the violet pigments, at least one selected from the group consisting of C.I. Pigment Violet 19, 23, and 29 is more preferable.

When preparing a blue colored curable resin composition, the colorant (A) preferably contains, for example, 30% by mass or more and 99% by mass or less, preferably 50% by mass or more, and more preferably 60% by mass or more, of the blue colorant in 100% by mass of the total colorant. Also, when a violet colorant is included, the content of the blue colorant is, for example, 5% by mass or more and 95% by mass or less, preferably 10% by mass or more and 80% by mass or less, and more preferably 20% by mass or more and 60% by mass or less, in 100% by mass of the total of the blue colorant and the violet colorant.

When preparing a yellow colored curable resin composition, the colorant (A) preferably contains at least one yellow colorant, more preferably contains at least one yellow pigment, and even more preferably contains two or more yellow pigments.

As the yellow pigment, at least one selected from the group consisting of C.I. Pigment Yellow 129, 138, 139, 150, and 185 is preferable, and at least one selected from the group consisting of C.I. Pigment Yellow 138, 139, 150, and 185 is more preferable.

When preparing a yellow colored curable resin composition, the colorant (A) preferably contains a yellow colorant in an amount of, for example, 50% by mass or more, preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly preferably 100% by mass, based on 100% by mass of all colorants.

When the colored curable resin composition contains a solvent (E), a colorant-containing liquid containing the colorant (A) and the solvent (E) may be prepared in advance, and then the colorant-containing liquid may be used to prepare the colored curable resin composition. When the colorant (A) is not soluble in the solvent (E), for example, when the colorant (A) contains a pigment (A2), the colorant-containing liquid can be prepared by dispersing the colorant (A) in the solvent (E) and mixing. The colorant-containing liquid may contain a part or all of the solvent (E) contained in the colored curable resin composition.

The solid content in the colorant-containing liquid is less than 100% by mass, preferably 1% by mass to 80% by mass, more preferably 2% by mass to 70% by mass, and even more preferably 5% by mass to 65% by mass, based on the total amount of the colorant-containing liquid.

The content of colorant (A) in the colorant-containing liquid is less than 100% by mass, preferably 0.5% by mass to 80% by mass, more preferably 1% by mass to 70% by mass, and even more preferably 2.5% by mass to 65% by mass, based on the total amount of solids in the colorant-containing liquid.

If necessary, the colorant (A) may be subjected to a rosin treatment, a surface treatment using a derivative having an acidic or basic group introduced therein, a grafting treatment to the surface of the colorant (A) using a polymer compound, a micronization treatment using a sulfuric acid micronization method or a salt milling method, a washing treatment using an organic solvent or water to remove impurities, a removal treatment using an ion exchange method for ionic impurities, or the like. It is preferable that the particle size of the colorant (A) is approximately uniform.

Colorant (A) can be made to be uniformly dispersed in the solution by adding a dispersant and carrying out a dispersion treatment. When two or more types of colorant (A) are used in combination, each may be dispersed alone, or multiple types may be mixed and dispersed.

Examples of the dispersant include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersant, when expressed by trade name, include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLORENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.). In addition, as the dispersant, a resin (B) described later (preferably resin [K1], more preferably 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid copolymer) may be used. The dispersant preferably contains the above-mentioned acrylic dispersant and resin (B), and preferably does not contain a copper phthalocyanine derivative.

When a dispersant is used, the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10,000 parts by mass or less, preferably 5 parts by mass or more and 5,000 parts by mass or less, more preferably 10 parts by mass or more and 1,000 parts by mass or less, and even more preferably 15 parts by mass or more and 800 parts by mass or less, per 100 parts by mass of colorant (A) in the colorant-containing liquid. When the amount of the dispersant used is within the above range, a colorant-containing liquid (hereinafter sometimes referred to as a colorant dispersion or pigment dispersion) in a more uniformly dispersed state tends to be obtained.

When a colorant-containing liquid containing a colorant (A) and a solvent (E) is prepared in advance and then the colorant-containing liquid is used to prepare a colored curable resin composition, the colorant-containing liquid may already contain a part or all, preferably a part, of the resin (B) contained in the colored curable resin composition. By including the resin (B) in advance, the dispersion stability of the colorant-containing liquid can be further improved.

When the colorant-containing liquid contains resin (B), the content of resin (B) is, for example, 10 parts by mass or more and 10,000 parts by mass or less, preferably 20 parts by mass or more and 5,000 parts by mass or less, and more preferably 25 parts by mass or more and 2,500 parts by mass or less, relative to 100 parts by mass of colorant (A) in the colorant-containing liquid.

The content of the colorant (A) is preferably 1% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 70% by mass or less, even more preferably 15% by mass or more and 65% by mass or less, and even more preferably 18% by mass or more and 50% by mass or less, based on the total amount of solids in the colored curable resin composition. When the content of the colorant (A) is within the above range, the color density when made into a color filter is sufficient, and the necessary amount of the resin (B) can be contained in the composition, so that a pattern with sufficient mechanical strength can be formed, which is preferable.
The content of the colorant (A) is particularly preferably more than 36% by mass and not more than 90% by mass, and most preferably 38% by mass or more and not more than 85% by mass, based on the total amount of solids in the colored curable resin composition. When the content of the colorant (A) is in the above range, the color of the color filter can be darkened.
Here, the "total amount of solids" in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the colored curable resin composition. The total amount of solids and the content of each component relative thereto can be measured by a known analytical means such as liquid chromatography or gas chromatography.

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

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

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

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

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

(b1-1) includes glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

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

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 a hydrogen atom contained in the alkyl group may be substituted with a hydroxy group.
^Xa and ^{Xb each} represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S- or *-R ^c -NH-.
^Rc represents an alkanediyl group having 1 to 6 carbon atoms.
* represents a bond to O.

Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.
R ^a and R ^b are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group.
^Xa and ^Xb are preferably a single bond, a methylene group, an ethylene group, *-CH ₂ -O-, and *-CH ₂ CH ₂ -O-, and more preferably a single bond or *-CH ₂ CH ₂ -O- (* represents a bond to O).

Examples of compounds represented by formula (I) include compounds represented by any of formulas (I-1) to (I-15). Among them, compounds represented by formulas (I-1), (I-3), (I-5), (I-7), (I-9) or (I-11) to (I-15) are preferred, and compounds represented by formulas (I-1), (I-7), (I-9) or (I-15) are more preferred.

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

The compound represented by formula (I) and the compound represented by formula (II) may be used alone or in combination of two or more kinds. When the compound represented by formula (I) and the compound represented by formula (II) are used in combination, the content ratio thereof [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.

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

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

As for (b), (b1) is preferable in that it can further increase the reliability of the heat resistance, chemical resistance, etc. of the obtained color filter. Furthermore, (b1-2) is more preferable in that the storage stability of the colored curable resin composition is excellent.

Examples of (c) include (meth)acrylic acid ester monomers, unsaturated carboxylates such as unsaturated dicarboxylates, and vinyl monomers having an unsaturated aliphatic hydrocarbon ring, an unsaturated heterocycle, or an aromatic ring.
Examples of the (meth)acrylic acid ester monomer include (meth)acrylic acid 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, and cyclopentyl (meth)acrylate (preferably, C _1-10 alkyl (meth)acrylate);
(meth)acrylic acid esters having a linear or branched aliphatic unsaturated hydrocarbon group, such as allyl (meth)acrylate and propargyl (meth)acrylate;
(meth)acrylic acid esters having a cyclic saturated hydrocarbon group, such as cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate (commonly known in the technical field as "dicyclopentanyl (meth)acrylate" and sometimes called "tricyclodecyl (meth)acrylate"), isobornyl (meth)acrylate, and adamantyl (meth)acrylate;
(meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, such as tricyclo[5.2.1.0 ^2,6 ]decen-8-yl(meth)acrylate (commonly known as "dicyclopentenyl(meth)acrylate" in the technical field), and dicyclopentanyloxyethyl(meth)acrylate;
(meth)acrylic acid esters having an aromatic ring, such as phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate, and phenoxybenzyl (meth)acrylate;
Examples of the hydroxyl group-containing (meth)acrylic acid esters include 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate.
Examples of the unsaturated dicarboxylic acid ester include dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate.

Among these unsaturated carboxylic acid esters, C _1-10 alkyl (meth)acrylates such as methyl methacrylate and 2-ethylhexyl acrylate;
(meth)acrylic acid esters having a cyclic saturated hydrocarbon group, such as tricyclo[5.2.1.0 ^2,6 ]decan-8-yl(meth)acrylate;
(meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, such as tricyclo[5.2.1.0 ^2,6 ]decene-8-yl (meth)acrylate;
Preferred are (meth)acrylic acid esters having an aromatic ring, such as benzyl (meth)acrylate and phenoxybenzyl (meth)acrylate.

Examples of vinyl monomers having an unsaturated aliphatic hydrocarbon ring include bicyclo[2.2.1]hept-2-ene (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'-hydroxy 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6- Dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1 ]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene are examples of bicyclo unsaturated compounds.
Examples of vinyl monomers having an unsaturated heterocycle include dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide.
Examples of vinyl monomers having an aromatic ring include styrene-based monomers such as styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene.
Other vinyl monomers include nitrile group-containing monomers such as acrylonitrile and methacrylonitrile;
Halogen atom-containing monomers such as vinyl chloride and vinylidene chloride;
Examples of the monomer include acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene.
Among these vinyl monomers, from the viewpoints of copolymerization reactivity and heat resistance, styrene-based monomers such as styrene and vinyltoluene, dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide and N-benzylmaleimide, and bicyclo unsaturated compounds such as bicyclo[2.2.1]hept-2-ene (also called 2-norbornene) are preferred.

The structural unit obtained by adding (b) to a structural unit derived from (a) refers to a unit formed by bonding (b) by addition to a structural unit derived from (a) constituting the main chain of the copolymer, and has a pendant unsaturated group derived from (b). In this structural unit, (a) may be any of the above-mentioned examples, and (b) may also be any of the above-mentioned examples. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferable. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferable, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferable.

The structural unit in which (a) is added to a structural unit derived from (b) refers to a unit formed by bonding (a) by addition to a structural unit derived from (b) constituting the main chain of the copolymer, and has a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above-mentioned examples, and (a) may also be any of the above-mentioned examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferable, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferable. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferable.

The structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic anhydride refers to a structural unit obtained by half-esterification of a carboxylic anhydride to a hydroxyl group generated by adding (a) to a structural unit derived from (b) constituting the main chain of the copolymer, and has a pendant carboxyl group derived from the carboxylic anhydride and a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above-mentioned examples, and (a) may also be any of the above-mentioned examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferable, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferable. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferable.
Examples of the carboxylic acid anhydride include saturated aliphatic polycarboxylic acid anhydrides such as malonic anhydride, succinic anhydride, glutaric anhydride, and adipic anhydride; unsaturated aliphatic polycarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, and itaconic anhydride; aromatic polycarboxylic acid anhydrides such as 3-vinylphthalic anhydride and 4-vinylphthalic anhydride; and alicyclic polycarboxylic acid 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.

In the resin [K1], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K1] is as follows:
Structural units derived from (a): 2 to 60 mol%
Structural units derived from (b): 40 to 98 mol%
It is preferred that
Structural units derived from (a): 10 to 50 mol%
Structural units derived from (b): 50 to 90 mol%
It is more preferable that:
It is also preferred that the copolymer contains substantially no structural units derived from (c).
The total of the structural units derived from (a) and the structural units derived from (b) is, for example, 90 mol % or more, preferably 95 mol % or more, more preferably 98 mol % or more, and particularly preferably 100 mol % of all the structural units constituting the resin [K1].
When the ratio of the structural units of the resin [K1] is within the above range, the colored curable resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the obtained color filter.

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

Specific examples include a method in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, and the mixture is heated and kept warm while stirring. The polymerization initiator and solvent used here are not particularly limited, and those commonly used in the field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and solvents that dissolve each monomer are sufficient, and examples of the solvent include the solvents described below as the solvent (E) of the colored curable resin composition of the present invention.

The resulting copolymer may be used as it is in the solution after the reaction, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. In particular, by using the solvent contained in the colored curable resin composition of the present invention as the solvent during this polymerization, the solution after the reaction can be used as it is in the preparation of the colored curable resin composition of the present invention, and the manufacturing process of the colored curable resin composition of the present invention can be simplified.

In the resin [K2], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K2] is as follows:
Structural units derived from (a): 2 to 45 mol%
Structural units derived from (b): 2 to 95 mol%
Structural units derived from (c): 1 to 65 mol%
It is preferred that
Structural units derived from (a): 5 to 40 mol%
Structural units derived from (b): 5 to 80 mol%
Structural units derived from (c): 5 to 60 mol%
It is more preferable that
Structural units derived from (a): 10 to 30 mol %
Structural units derived from (b): 10 to 70 mol%
Structural units derived from (c): 10 to 40 mol%
It is even more preferred that:
The total of the structural units derived from (a), the structural units derived from (b), and the structural units derived 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 % of all the structural units constituting the resin [K2].
When the ratio of the structural units of the resin [K2] is within the above range, the colored curable resin composition tends to have excellent storage stability, developability when forming a colored pattern, and the obtained color filter tends to have excellent solvent resistance, heat resistance, and mechanical strength.

In the 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)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, (meth)acrylic acid esters having an aromatic ring, and dicarbonyl imide derivatives are preferred.

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

In the resin [K3], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K3] is as follows:
Structural units derived from (a): 2 to 60 mol%
Structural units derived from (c): 40 to 98 mol%
It is preferred that
Structural units derived from (a): 10 to 50 mol %
Structural units derived from (c): 50 to 90 mol%
It is more preferable that
Structural units derived from (a): 35 to 45 mol%
Structural units derived from (c): 55 to 65 mol%
It is even more preferred that:
It is also preferred that the copolymer is substantially free of structural units derived from (b).
The total of the structural units derived from (a) and the structural units derived 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% of all the structural units constituting the resin [K3].

In the resin [K3], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid, and (c) is preferably a (meth)acrylic acid ester having an aromatic ring.
Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

In the resin [K4], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K4] is as follows:
Structural units derived from (a) (without (b) added): 1 to 60 mol%
Structural units obtained by adding (b) to a structural unit derived from (a): 1 to 50 mol %
Structural units derived from (c): 30 to 90 mol%
It is preferred that
Structural units derived from (a) (without (b) added): 5 to 50 mol %
Structural units obtained by adding (b) to a structural unit derived from (a): 5 to 40 mol%
Structural units derived from (c): 35 to 80 mol%
It is more preferable that
Structural units derived from (a) (without (b) added): 10 to 40 mol%
Structural units obtained by adding (b) to a structural unit derived from (a): 10 to 25 mol%
Structural units derived from (c): 40 to 75 mol%
It is even more preferred that:
The total of the structural units derived from (a) (to which (b) is not added), the structural units obtained by adding (b) to the structural units derived from (a), and the structural units derived 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 % of all the structural units constituting the resin [K4].

As the structural unit derived from (a) (without the addition of (b)), a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As the structural unit in which (b) is added to a structural unit derived from (a), a structural unit in which a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is added to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As the structural unit derived from (c), one or more types selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, (meth)acrylic acid esters having an aromatic ring, bicyclo unsaturated compounds, and styrene-based monomers are preferred, and two or more types are more preferred. When (c) has two types of structural units derived from it, it is preferable to select two types from unsaturated carboxylic acid esters such as (meth)acrylic acid esters, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and (meth)acrylic acid esters having an aromatic ring, and to select two or more types from bicyclo unsaturated compounds and vinyl monomers such as styrene-based monomers.

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

Next, a part of the carboxylic acid and/or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b).
Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air instead of nitrogen, and (b) a catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130° C. for 1 to 10 hours, thereby producing the resin [K4].
The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, relative to 100 mol of (a). By using this range, the storage stability of the colored curable resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern tend to be good.
The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c).
The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

In the resin [K5], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K5] is as follows:
Structural units derived from (b) ((a) is not added): 0 to 30 mol%
Structural units obtained by adding (a) to a structural unit derived from (b): 5 to 95 mol%
Structural units derived from (c): 5 to 95 mol%
It is preferred that
Structural units derived from (b) ((a) is not added): 0 to 10 mol %
Structural units obtained by adding (a) to a structural unit derived from (b): 15 to 90 mol%
Structural units derived from (c): 10 to 85 mol%
It is more preferable that
Structural units derived from (b) ((a) is not added): 0 to 5 mol%
Structural units obtained by adding (a) to a structural unit derived from (b): 20 to 80 mol%
Structural units derived from (c): 20 to 80 mol%
It is even more preferred that:
The total of the structural units derived from (b) (to which (a) is not added), the structural units obtained by adding (a) to the structural units derived from (b), and the structural units derived 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 % of all the structural units constituting the resin [K5].
As the structural unit derived from (b) (without (a) added), 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 the structural unit in which (a) is added to a structural unit derived from (b), a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid is added to 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 the structural unit derived from (c), one or more types selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group are preferred, and two or more types are more preferred.

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

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

In the resin [K5'], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K5'] is as follows:
Structural units derived from (a) (without (b) added): 0 to 30 mol %
Structural units obtained by adding (b) to a structural unit derived from (a): 5 to 95 mol%
Structural units derived from (c): 5 to 95 mol%
It is preferred that
Structural units derived from (a) (without (b) added): 0 to 10 mol %
Structural units obtained by adding (b) to a structural unit derived from (a): 15 to 90 mol%
Structural units derived from (c): 10 to 85 mol%
It is more preferable that
Structural units derived from (a) (without (b) added): 0 to 5 mol %
Structural units obtained by adding (b) to a structural unit derived from (a): 20 to 80 mol%
Structural units derived from (c): 20 to 80 mol%
It is even more preferred that:
The total of the structural units derived from (a) (without (b) added), the structural units derived from (a) with (b) added, and the structural units derived 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% of all structural units constituting the resin [K5'].
As the structural unit derived from (a) (without the addition of (b)), a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As the structural unit obtained by adding (b) to a structural unit derived 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 a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As the structural unit derived from (c), one or more types selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group are preferred, and two or more types are more preferred.
Resin [K5'] may be produced by referring to the production method of resin [K4] described above, and the amount of (b) used may be more than 80 mol and 100 mol or less per 100 mol of (a).

In the resin [K6], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K6] is as follows:
Structural units derived from (b) ((a) is not added): 0 to 30 mol%
A structural unit obtained by adding (a) to a structural unit derived from (b) (no carboxylic acid anhydride is added); 2 to 80 mol%
A structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride thereto: 2 to 60 mol %
Structural units derived from (c): 5 to 95 mol%
It is preferred that
Structural units derived from (b) ((a) is not added): 0 to 10 mol %
A structural unit in which (a) is added to a structural unit derived from (b) (no carboxylic acid anhydride is added); 5 to 70 mol%
A structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride thereto: 5 to 50 mol %
Structural units derived from (c): 10 to 85 mol%
It is more preferable that
Structural units derived from (b) ((a) is not added): 0 to 5 mol%
Structural units in which (a) is added to a structural unit derived from (b) (no carboxylic acid anhydride is added): 10 to 65 mol%
A structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride thereto: 20 to 80 mol %
Structural units derived from (c): 20 to 80 mol%
It is even more preferred that:
The total of the structural unit derived from (b) (to which (a) is not added), the structural unit obtained by adding (a) to the structural unit derived from (b) (to which carboxylic acid anhydride is not added), the structural unit obtained by adding (a) to the structural unit derived from (b) and further adding a carboxylic acid anhydride, and the structural unit derived 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 % of all the structural units constituting the resin [K6].

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

Resin [K6] is produced in the first step by the same method as that for producing resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the copolymer obtained may be used as it is in the form of a solution after the reaction, or a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation.
The ratio of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer is,
Structural units derived from (b): 5 to 95 mol%
Structural units derived from (c): 5 to 95 mol%
It is preferred that
Structural units derived from (b): 10 to 90 mol%
Structural units derived from (c): 10 to 90 mol%
It is more preferable that:

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

The hydroxy group generated by the reaction of the cyclic ether with the carboxylic acid or carboxylic acid anhydride contained in (a) is reacted with the carboxylic acid anhydride.
The amount of the carboxylic acid anhydride used is preferably 0.05 to 1 mol, more preferably 0.10 to 0.8 mol, and even more preferably 0.13 to 0.7 mol, relative to 1 mol of the amount of (a) used (in other words, 1 mol of hydroxy groups generated by the use of (a)).

Specific examples of the resin (B) include resins [K1] such as 3,4-epoxycyclohexylmethyl(meth)acrylate/(meth)acrylic acid copolymer and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid copolymer;
Glycidyl (meth)acrylate/benzyl (meth)acrylate/(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/tricyclo[5.2.1.0 2,6 ] decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/tricyclo[5.2.1.0 ^2,6 ] decene-8-yl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] decyl acrylate/(meth)acrylic acid/benzyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] Decyl acrylate/(meth)acrylic acid/phenoxybenzyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene copolymer, and other resins [K2];
Resins such as benzyl (meth)acrylate/(meth)acrylic acid copolymers and styrene/(meth)acrylic acid copolymers [K3];
Resins [K4] such as a resin in which glycidyl (meth)acrylate is added to a portion of the carboxylic acid groups of a benzyl (meth)acrylate/(meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to a portion of the carboxylic acid groups of a tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to a portion of the carboxylic acid groups of a tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to a portion of the carboxylic acid groups of a norbornene/vinyl toluene/(meth)acrylic acid copolymer, and a resin in which glycidyl (meth)acrylate is added to a portion of the carboxylic acid groups of a norbornene/styrene/(meth)acrylic acid copolymer;
Resins [K5] such as a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate with (meth)acrylic acid, and a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate/styrene/glycidyl (meth)acrylate with (meth)acrylic acid;
Resins [K5'] such as a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate/(meth)acrylic acid with glycidyl (meth)acrylate, and a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid with glycidyl (meth)acrylate;
Examples of the resin [K6] include a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate with (meth)acrylic acid and further reacting the resulting resin with tetrahydrophthalic anhydride, a resin obtained by reacting a copolymer of 2-ethylhexyl (meth)acrylate/tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate with (meth)acrylic acid and further reacting the resulting resin with succinic anhydride, and a resin obtained by reacting a copolymer of methyl (meth)acrylate/2-ethylhexyl (meth)acrylate/tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate with (meth)acrylic acid and further reacting the resulting resin with succinic anhydride.

The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern tends to be improved.
The polydispersity of the resin (B) [weight average molecular weight (Mw)/number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

The acid value of resin (B) is preferably 20 to 170 mg-KOH/g, more preferably 25 to 150 mg-KOH/g, and even more preferably 30 to 135 mg-KOH/g, calculated as solid content. 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 determined, for example, by titration with an aqueous potassium hydroxide solution.

The content of resin (B) is preferably 2 to 65% by mass, more preferably 3 to 60% by mass, even more preferably 5 to 55% by mass, even more preferably 5 to 40% by mass, and particularly preferably 7 to 30% by mass, based on the total amount of solids. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and remaining film rate of the colored pattern tend to be improved.

As the resin (B), a resin having an ethylenic double bond is particularly preferred from the viewpoint of further improving the solvent resistance. When the resin (B) has 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 of the resins [K2] to [K6] containing at least one selected from (meth)acrylic acid esters having a linear or branched aliphatic unsaturated hydrocarbon group, (meth)acrylic acid esters 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). The resins [K4] to [K6] also have an ethylenic double bond derived from an additional component (preferably the monomer (a) or the monomer (b)).

Furthermore, as the resin (B), those having a structural unit derived from the monomer (b), such as the resin [K1] and/or the resin [K2], are particularly preferred.
Furthermore, the resin (B) is particularly preferably any one of the resins [K2] to [K4], which contains a (meth)acrylic acid ester having an aromatic ring as the monomer (c), and in which the total of the structural units derived from the (meth)acrylic acid ester having an aromatic ring and the structural units derived from the (a) is 60 mol % or more, based on 100 mol % of all structural units.

<Polymerizable Compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by active radicals and/or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the above-mentioned monomers (a), (b), and (c).

Examples of polymerizable compounds 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.

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, ethyl Examples of the dipentaerythritol hexa(meth)acrylate include 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, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

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

The content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 3% by mass or more and 90% by mass or less, more preferably 5% by mass or more and 80% by mass or less, and even more preferably 7% by mass or more and 70% by mass or less, based on the total amount of solids in the colored curable resin composition.

<Polymerization initiator (D)>
The polymerization initiator (D) may be any compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and includes compounds represented by the following formula (I).

(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.
n represents an integer of 0 to 4.
The --CH ₂ -- contained in the hydrocarbon group may be replaced with --O--, --S--, --CO--, or --OCO--.

Examples of the hydrocarbon group represented by ^R1 , ^R2 , ^R3 , ^R4 , and ^R5 include saturated hydrocarbon groups having 1 to 20 carbon atoms, unsaturated aliphatic hydrocarbon groups having 1 to 20 carbon atoms, and aromatic hydrocarbon groups having 6 to 20 carbon atoms.

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

Examples of the unsaturated aliphatic hydrocarbon group having 1 to 20 carbon atoms include alkenyl groups such as vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, hexadecenyl, octadecenyl, and icosenyl; alkynyl groups such as ethynyl, propynyl, hexynyl, decynyl, and icosenyl; cycloalkenyl groups such as cyclopentenyl, cyclohexenyl, and cycloheptenyl; and the like. The number of carbon atoms in the unsaturated aliphatic hydrocarbon group is preferably 2 to 18, more preferably 2 to 15, and even more preferably 2 to 10.

Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di(2,2-dimethylpropyl)phenyl group, a naphthyl group, a benzyl group, a phenylethyl group, and a phenylbutyl group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 15, and even more preferably 6 to 12.

Examples of the substituent that the hydrocarbon group represented by R ¹ , R ² , R ³ , R ⁴ , and R ⁵ may have include 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.

n represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably an integer of 0 or 1, and even more preferably 0.
The --CH ₂ -- contained in the hydrocarbon group may be replaced by --O--, --S--, --CO--, or --OCO--, provided that adjacent --CH ₂ -- are not simultaneously replaced by the same type of group, and that the terminal --CH ₂ -- is not replaced.

The hydrocarbon groups represented by R ¹ , R ² , R ³ , R ⁴ , and R ⁵ are preferably saturated hydrocarbon groups having 1 to 20 carbon atoms or unsaturated aliphatic hydrocarbon groups having 1 to 20 carbon atoms, more preferably saturated hydrocarbon groups having 1 to 20 carbon atoms, even more preferably linear or branched saturated hydrocarbon groups having 1 to 10 carbon atoms, and even more preferably linear or branched alkyl groups having 1 to 8 carbon atoms.
The hydrocarbon groups represented by R ¹ , R ² , R ³ , R ⁴ and R ⁵ may be the same or different, and are preferably different.

Among these, it is preferable that R ¹ is a linear 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 are linear alkyl groups having 1 to 8 carbon atoms, and R ⁵ is a linear or branched alkyl group having 1 to 8 carbon atoms, and it is more preferable that R ¹ is a linear 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 are linear alkyl groups having 1 to 3 carbon atoms, and R ⁵ is a linear or branched alkyl group having 1 to 8 carbon atoms.

In addition to the compound represented by formula (I), other polymerization initiators may be used. Examples of other polymerization initiators (D) include O-acyloxime compounds (excluding the compound represented by formula (I) and Irgacure OXE03), alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

The O-acyloxime compound is a compound having a partial structure represented by formula (d-1). In the formula, * represents a bond.

Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl)phenyl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and the like. Commercially available products such as IRGACURE OXE01 (N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine), IRGACURE OXE02 (N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine) (both manufactured by BASF), and N-1919 (manufactured by ADEKA) may also be used. Among them, the O-acyloxime compounds include N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine and N-benzoyloxy- At least one selected from the group consisting of 1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferred, with N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine being more preferred. These O-acyloxime compounds tend to produce optical filters with high brightness.

The alkylphenone compound is a compound having a partial structure represented by formula (d-2) or a partial structure represented by formula (d-3). In these partial structures, the benzene ring may have a substituent. In the formula, * represents a bond.

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

Examples of the compound having a partial structure represented by formula (d-3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.
In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d-2).

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

The acylphosphine oxide compound may be 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

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

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

Examples of polymerization initiators that generate acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate, as well as nitrobenzyl tosylates and benzoin tosylates.

As the polymerization initiator (D), a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound is preferred, a polymerization initiator containing an O-acyloxime compound and/or a biimidazole compound is more preferred, and a polymerization initiator containing an O-acyloxime compound is even more preferred.

The content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass or less, and more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, thereby improving the productivity of the optical filter.

The contents of the resin (B), the polymerizable compound (C), and the polymerization initiator (D) are preferably 10 mass% or more and less than 46 mass%, more preferably 12 mass% or more and 44 mass% or less, even more preferably 14 mass% or more and 42 mass% or less, and still more preferably 16 mass% or more and 40 mass% or less, in the total amount of the solid contents of the colored curable resin composition.
When the contents of the resin (B), the polymerizable compound (C), and the polymerization initiator (D) satisfy the above ranges, the remaining film rate of the color filter can be improved even if the amount of the curable component is reduced.

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

Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-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, and preferably 4,4'-bis(diethylamino)benzophenone. In addition, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used as the amine compound.

Examples of alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

Thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

Examples of carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

When these polymerization initiator aids (D1) are used, the content is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of all the resins (B) and the polymerizable compounds (C) contained in the colored curable resin composition.

<Solvent (E)>
The solvent (E) is not particularly limited, and any solvent commonly used in the relevant field can be used.
Examples of the solvent (E) include ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. Two or more of these solvents may be used in combination.

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

Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2-ethoxy-2-methylpropionate, Examples of such ether acetates include ethyl acetate, 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.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

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

Aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene, etc.

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

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.

When the solvent (E) is included, the content of the solvent (E) is usually 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 97% by mass or less, even more preferably 70% by mass or more and 96% by mass or less, and even more preferably 73% by mass or more and 95% by mass or less, based on the total amount of the colored curable resin composition. In other words, the total amount of solids in the colored curable resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 3% by mass or more and 50% by mass or less, even more preferably 4% by mass or more and 30% by mass or less, and even more preferably 5% by mass or more and 27% by mass or less. When the content of the solvent (E) is within the above range, the flatness during application is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics tend to be good.

<Thiol Compound (T)>
The colored curable resin composition of the present invention may contain a thiol compound (T).
The thiol compound (T) is a compound having a sulfanyl group (-SH) in the molecule.

Examples of compounds having one sulfanyl group in the molecule include 2-sulfanyloxazole, 2-sulfanylthiazole, 2-sulfanylbenzimidazole, 2-sulfanylbenzothiazole, 2-sulfanylbenzoxazole, 2-sulfanylnicotinic acid, 2-sulfanylpyridine, 2-sulfanylpyridin-3-ol, 2-sulfanylpyridine-N-oxide, 4-amino-6-hydroxy-2-sulfanylpyrimidine, 4-amino-6-hydroxy-2-sulfanylpyrimidine, 4-amino-2-sulfanylpyrimidine, 6-amino-5-nitroso-2-thiouracil, and 4,5-diamino-6-hydroxy-2-sulfanylpyrimidine. , 4,6-diamino-2-sulfanylpyrimidine, 2,4-diamino-6-sulfanylpyrimidine, 4,6-dihydroxy-2-sulfanylpyrimidine, 4,6-dimethyl-2-sulfanylpyrimidine, 4-hydroxy-2-sulfanyl-6-methylpyrimidine, 4-hydroxy-2-sulfanyl-6-propylpyrimidine, 2-sulfanyl-4-methylpyrimidine, 2-sulfanylpyrimidine, 2-thiouracil, 3,4,5,6-tetrahydropyrimidine-2-thiol, 4,5-diphenylimidazole-2-thiol, 2-sulfanylimidazole, 2-sulfanyl-1-methylimidazole, 4-amino-3-hydrazino-5-sulfanyl-1, 2,4-triazole, 3-amino-5-sulfanyl-1,2,4-triazole, 2-methyl-4H-1,2,4-triazole-3-thiol, 4-methyl-4H-1,2,4-triazole-3-thiol, 3-sulfanyl-1H-1,2,4-triazole-3-thiol, 2-amino-5-sulfanyl-1,3,4-thiadiazole, 5-amino-1,3,4-thiadiazole-2-thiol, 2,5-disulfanyl-1,3,4-thiadiazole, (furan-2-yl)methanethiol, 2-sulfanyl-5-thiazolidone, 2-sulfanylthiazoline, 2-sulfanyl-4(3H)-quinazolinone, 1-phenyl-1H-tetrazole-5-thiol , 2-quinolinethiol, 2-sulfanyl-5-methylbenzimidazole, 2-sulfanyl-5-nitrobenzimidazole, 6-amino-2-sulfanylbenzothiazole, 5-chloro-2-sulfanylbenzothiazole, 6-ethoxy-2-sulfanylbenzothiazole, 6-nitro-2-sulfanylbenzothiazole, 2-sulfanylnaphthoimidazole, 2-sulfanylnaphthoxazole, 3-sulfanyl-1,2,4-triazole, 4-amino-6-sulfanylpyrazolo[2,4-d]pyridine, 2-amino-6-purinethiol, 6-sulfanylpurine, 4-sulfanyl-1H-pyrazolo[2,4-d]pyrimidine, etc.

Compounds having two or more sulfanyl groups in the molecule include hexanedithiol, decanedithiol, 1,4-bis(methylsulfanyl)benzene, butanediol bis(3-sulfanylpropionate), butanediol bis(3-sulfanyl acetate), ethylene glycol bis(3-sulfanyl acetate), trimethylolpropane tris(3-sulfanyl acetate), butanediol bis(3-sulfanylpropionate), trimethylolpropane tris(3-sulfanyl acetate), Examples include pantos(3-sulfanylpropionate), trimethylolpropane tris(3-sulfanyl acetate), pentaerythritol tetrakis(3-sulfanylpropionate), pentaerythritol tetrakis(3-sulfanyl acetate), trishydroxyethyl tris(3-sulfanylpropionate), pentaerythritol tetrakis(3-sulfanyl butyrate), and 1,4-bis(3-sulfanylbutyloxy)butane.

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 even more preferably 10 to 40 parts by mass, per 100 parts by mass of the polymerization initiator (D). When the content of the thiol compound (T) is within this range, the sensitivity tends to be high and the developability tends to be good.

<Leveling Agent (F)>
Examples of the leveling agent (F) include silicone surfactants, fluorine-based surfactants, and silicone surfactants having fluorine atoms, which may have a polymerizable group in the side chain.

Examples of silicone surfactants include surfactants having a siloxane bond in the molecule. Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (product names: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and 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).

Examples of fluorosurfactants include surfactants having a fluorocarbon chain in the molecule. Specific examples include Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by AGC Corporation), and E5844 (manufactured by Daikin Fine Chemicals Research Institute Ltd.).

Examples of silicone surfactants having fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in the molecule. Specific examples include Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and even more preferably 0.005% by mass or more and 0.1% by mass or less, based on the total amount of the colored curable resin composition. Note that this content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Other ingredients>
The colored curable resin composition may contain additives known in the technical field, such as a filler, another polymer compound, an adhesion promoter, a quencher, an antioxidant, a light stabilizer, and a chain transfer agent, as necessary.
Examples of adhesion promoters include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropylmethyldimethoxysilane, 3-glycidyloxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-sulfur Examples of the silane include anylpropyltrimethoxysilane, 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.

<Method for producing colored curable resin composition>
The colored curable resin composition can be prepared by mixing the colorant (A), the resin (B), the polymerizable compound (C), the polymerization initiator (D), and optionally the polymerization initiator aid (D1), the solvent (E), the leveling agent (F), and other components. The mixing can be carried out using known or conventional equipment and conditions.
The colorant (A) may be used as a colorant-containing liquid obtained by mixing with a part or all of the solvent (E) in advance and dispersing using a bead mill or the like until the average particle size becomes about 0.2 μm or less, and it is preferable to use it as a colorant-containing liquid. In this case, the dispersant and a part or all of the resin (B) may be blended as necessary. The remaining components are mixed into the colorant-containing liquid obtained in this way to a predetermined concentration, whereby the desired colored curable resin composition can be prepared.
In addition, when a dye is contained as the colorant (A), the dye may be dissolved in advance in a part or all of the solvent (E) to prepare a solution. The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

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

The thickness of the color filter to be produced is not particularly limited and can be adjusted as appropriate depending on the purpose and application, and is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, even more preferably 4.5 μm or less, and is preferably 0.1 μm or more, more preferably 0.2 μm or more, even more preferably 0.3 μm or more.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass with a silica-coated surface, resin plates such as polycarbonate, polymethylmethacrylate, and polyethylene terephthalate, silicon, and substrates on which aluminum, silver, and thin films of silver/copper/palladium alloys are formed may be used. On these substrates, other color filter layers, resin layers, transistors, circuits, and the like may be formed. Also, a silicon substrate treated with HMDS (hexamethyldisilazane) may be used.

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

Next, the colored composition layer is exposed through a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended use is used. In addition, it is preferable to use an exposure device such as a mask aligner or stepper, since it is possible to uniformly irradiate the entire exposed surface with parallel light and to accurately align the photomask with the substrate on which the colored composition layer is formed. When a colored coating film is formed, exposure can be performed without using a photomask.

The light source used for exposure is preferably a light source that generates light with a wavelength of 250 nm or more and 450 nm or less. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

The colored composition layer after exposure is brought into contact with a developer and developed to form a colored pattern on the substrate. The unexposed portion of the colored composition layer is dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may contain a surfactant. The development method may be any of a paddle method, a dipping method, and a spray method. Furthermore, the substrate may be tilted at any angle during development.
After development, the substrate is preferably washed with water.

Furthermore, it is preferable to perform post-baking on the obtained colored pattern or colored coating film. The post-baking temperature is preferably from 80° C. to 250° C., and more preferably from 100° C. to 245° C. The post-baking time is preferably from 1 minute to 120 minutes, and more preferably from 2 minutes to 30 minutes.
The colored pattern and colored coating film thus obtained are useful as a color filter.

From the viewpoint of solvent resistance, the colored coating film is preferably a colored coating film that, after immersion in propylene glycol monomethyl ether acetate (PGMEA) or propylene glycol monomethyl ether (PGME) at a temperature of 23° C. for 5 minutes, has a small color difference (ΔE*ab) before and after immersion.
The color difference (ΔE*ab) of the colored coating film to PGME is preferably 5.5 or less, more preferably 5.0 or less, even more preferably 4.5 or less, and even more preferably 4.0 or less.

<Display device, solid-state image sensor>
The color filter is useful as a color filter for use in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.), solid-state imaging devices, and the like.

The present invention will be explained in more detail below with reference to examples. However, the present invention is not limited to the following examples, and it is of course possible to carry out the invention with appropriate modifications within the scope of the above and below-mentioned aims, all of which are included in the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass."

Synthesis Example 1: Preparation of Pigment Dispersion (A-1)
C.I. Pigment Green 59 6.5 parts C.I. Pigment Yellow 139 1.0 parts C.I. Pigment Yellow 185 3.4 parts C.I. Pigment Blue 15:4 0.4 parts Acrylic pigment dispersant 3.2 parts Dispersion resin (resin (B-X)) 3.2 parts Ethylene glycol monobutyl ether 0.8 parts Diacetone alcohol 0.3 parts Propylene glycol monomethyl ether 2.5 parts Propylene glycol monomethyl ether acetate 78.7 parts were mixed and the pigment was thoroughly dispersed using a bead mill to obtain a pigment dispersion (A-1).

Synthesis Example 2: Preparation of Pigment Dispersion (A-2)
C.I. Pigment Blue 15:6 4.8 parts C.I. Pigment Blue 16 4.3 parts C.I. Pigment Violet 23 2.9 parts Acrylic pigment dispersant 4.1 parts Dispersion resin (resin (B-X)) 3.5 parts Diacetone alcohol 6.7 parts Propylene glycol monomethyl ether 2.0 parts Propylene glycol monomethyl ether acetate 71.7 parts were mixed and the pigment was thoroughly dispersed using a bead mill to obtain a pigment dispersion (A-2).

Synthesis Example 3: Preparation of Pigment Dispersion (A-3)
C.I. Pigment Green 36 6.6 parts C.I. Pigment Yellow 139 2.0 parts C.I. Pigment Yellow 150 3.3 parts Acrylic pigment dispersant 3.9 parts Dispersion resin (resin (B-X)) 4.7 parts Ethylene glycol monobutyl ether 1.6 parts Propylene glycol monomethyl ether 2.1 parts Propylene glycol monomethyl ether acetate 75.8 parts were mixed and the pigment was thoroughly dispersed using a bead mill to obtain a pigment dispersion (A-3).

Synthesis Example 4: Preparation of Pigment Dispersion (A-4)
C.I. Pigment Red 254 7.8 parts C.I. Pigment Yellow 139 4.2 parts Acrylic pigment dispersant 3.1 parts Dispersion resin (resin (B-X)) 2.2 parts Propylene glycol monomethyl ether 3.8 parts Propylene glycol monomethyl ether acetate 78.9 parts were mixed and the pigment was thoroughly dispersed using a bead mill to obtain a pigment dispersion (A-4).

Synthesis Example 5: Preparation of Resin (B-1)
276.8 parts of propylene glycol monomethyl ether acetate was placed in a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, and the mixture was stirred while replacing with nitrogen and heated to 120°C. Next, a monomer mixture consisting of 92.4 parts of 2-ethylhexyl acrylate, 184.9 parts of glycidyl methacrylate, and 12.3 parts of dicyclopentanyl methacrylate, to which 35.3 parts of t-butylperoxy-2-ethylhexanoate (polymerization initiator) had been added, was dropped into the flask from the dropping funnel over 2 hours. After the dropwise addition was completed, the mixture was stirred for another 30 minutes at 120°C to carry out a copolymerization reaction, and an addition copolymer was produced. Thereafter, the inside of the flask was replaced with air, and 93.7 parts of acrylic acid, 1.5 parts of triphenylphosphine (catalyst) and 0.8 parts of methoquinone (polymerization inhibitor) were added to the above addition copolymer solution, and the reaction was continued for 10 hours at 110 ° C., and the epoxy group derived from glycidyl methacrylate was reacted with acrylic acid to cleave the epoxy group, and at the same time, a polymerizable unsaturated bond was introduced into the side chain of the polymer. Next, 24.2 parts of succinic anhydride were added to the reaction system, and the reaction was continued for 1 hour at 110 ° C., and the hydroxyl group generated by the cleavage of the epoxy group was reacted with succinic anhydride to introduce a carboxyl group into the side chain, thereby obtaining a polymer. Finally, 383.3 parts of propylene glycol monomethyl ether acetate were added to the reaction solution, and a polymer (resin (B-1)) solution with a polymer solid content of 40% was obtained. The weight average molecular weight Mw of the produced 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 ethylenic double bond equivalent of the resin (B-1) was 350 g/mol.

Synthesis Example 6: Preparation of Resin (B-2)
A flask equipped with a stirrer, a thermometer, a reflux condenser, and a dropping funnel was filled with nitrogen at 0.02 L/min to create a nitrogen atmosphere, and 268 parts of ethyl lactate was added and heated to 70° C. with 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 following formula (II-1) mixed in a molar ratio of 50:50), and 7 parts of tricyclo[5.2.1.0 ^2,6 ]decen-8-yl acrylate (a compound represented by the following formula (c-1) and a compound represented by the following formula (c-2) mixed in a molar ratio of 50:50) were dissolved in 140 parts of ethyl lactate to prepare a solution, which was then dropped into a flask kept at 70° C. using a dropping funnel over a period of 4 hours. On the other hand, a solution of 30 parts of polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) dissolved in 225 parts of ethyl lactate was dropped into the flask over 4 hours using another dropping funnel. After the dropwise addition of the polymerization initiator solution was completed, the temperature was kept 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 x 10 ³ , a solid content of 36.7%, and a solution acid value of 44 mg-KOH/g. The solid content acid value was calculated from the above solid content and solution acid value to be 119 mg-KOH/g.

Synthesis Example 7: Preparation of Dispersion Resin
A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was 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 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-yl acrylate (content ratio: 1:1 by molar ratio), and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was kept 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 with a Brookfield viscometer (23°C). The weight average molecular weight Mw of the produced copolymer was 9.2×10 ³ , the dispersity was 2.08, and the acid value calculated as solid content was 77 mg-KOH/g. Resin (B-X) has the following structural units.

The resin (B-3) used was Lipoxy (registered trademark) SPC-2000 manufactured by Resonac Corporation.

Synthesis Example 8: Preparation of Resin (B-4)
Into a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 241 parts of propylene glycol monomethyl ether acetate was added, and the mixture was stirred while replacing the atmosphere with nitrogen and heated to 130°C.
Next, a monomer mixture consisting of 72.6 parts of 2-ethylhexyl acrylate, 145.3 parts of glycidyl methacrylate, and 9.7 parts of dicyclopentanyl methacrylate, to which 33.5 parts of t-butylperoxy-2-ethylhexanoate had been added, was dropped into the flask from the dropping funnel over a period of 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes to carry out a copolymerization reaction.
Thereafter, the flask was replaced with air, 73.7 parts of acrylic acid, 0.9 parts of triphenylphosphine and 0.9 parts of methoquinone were added, and the reaction was continued for 10 hours at 120°C. Then, 65.2 parts of succinic anhydride were added to the reaction system, and the reaction was continued for another 1.5 hours to obtain a polymer. Finally, 300 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 concentration was 40%, to obtain a polymer solution. The ethylenic double bond equivalent of resin (B-4) was 400 g/mol.

Synthesis Example 9: Preparation of Resin (B-5)
Into a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 258 parts of propylene glycol monomethyl ether acetate was added, and the mixture was stirred while replacing the atmosphere with nitrogen and heated to 120°C.
Next, a monomer mixture consisting of 89.5 parts of 2-ethylhexyl acrylate, 180.0 parts of glycidyl methacrylate, and 11.9 parts of dicyclopentanyl methacrylate, to which 10.9 parts of t-butylperoxy-2-ethylhexanoate had been added, was dropped into the flask from the dropping funnel over a period of 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes to carry out a copolymerization reaction.
Thereafter, the flask was replaced with air, 90.8 parts of acrylic acid, 1.1 parts of triphenylphosphine and 1.1 parts of methoquinone were added, and the reaction was continued for 10 hours at 120°C. Then, 18.0 parts of succinic anhydride were added to the reaction system, and the reaction was continued for another 30 minutes to obtain a polymer. Finally, 330 parts of propylene glycol monomethyl ether acetate were added to the reaction solution, and propylene glycol monomethyl ether acetate was added so that the polymer solid concentration was 40%, to obtain a polymer solution. The ethylenic double bond equivalent of resin (B-5) was 330 g/mol.

Synthesis Example 10: Preparation of Resin (B-6)
Into a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 257 parts of propylene glycol monomethyl ether acetate was added, and the mixture was stirred while replacing the atmosphere with nitrogen and heated to 120°C.
Next, 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, to which 6.8 parts of t-butylperoxy-2-ethylhexanoate had been added, was dropped into the flask from the dropping funnel over a period of 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes to carry out a copolymerization reaction.
Thereafter, the flask was replaced with air, 91.8 parts of acrylic acid, 1.1 parts of triphenylphosphine and 1.1 parts of methoquinone were added, and the reaction was continued for 10 hours at 120°C. Then, 17.9 parts of succinic anhydride were added to the reaction system, and the reaction was continued for another 30 minutes to obtain a polymer. Finally, 330 parts of propylene glycol monomethyl ether acetate were added to the reaction solution, and propylene glycol monomethyl ether acetate was added so that the polymer solid concentration was 40%, to obtain a polymer solution. The ethylenic double bond equivalent of resin (B-6) was 370 g/mol.

Synthesis Example 11: Preparation of Resin (B-7)
Into a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 178 parts of propylene glycol monomethyl ether acetate was added, and the mixture was stirred while replacing the atmosphere with nitrogen and heated to 100°C.
Next, 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, to which 47.1 parts of dimethyl 2,2'-azobis(2-methylpropionate) (polymerization initiator) was added, was dropped into the flask from the dropping funnel over a period of 2 hours. After the dropwise addition was completed, the mixture was stirred at 100°C for an additional 30 minutes to carry out a copolymerization reaction.
Thereafter, the atmosphere in the flask was replaced with air, and 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 for 10 hours at 120°C. Next, 22.1 parts of succinic anhydride were added to the reaction system, and the reaction was continued for another 1.5 hours to obtain a polymer.
Finally, 330 parts of propylene glycol monomethyl ether was added to the reaction solution, and then propylene glycol monomethyl ether acetate was added so that the polymer solid concentration became 40%, to obtain a polymer solution.

Synthesis Example 12: Preparation of Resin (B-8)
Into a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 349 parts of propylene glycol monomethyl ether acetate was added, and the mixture was stirred while replacing the atmosphere with nitrogen and heated to 120°C.
Next, a monomer mixture consisting of 169.2 parts of benzyl methacrylate, 103.3 parts of methacrylic acid, and 52.9 parts of dicyclopentanyl methacrylate, to which 23.4 parts of t-butylperoxy-2-ethylhexanoate had been added, was dropped into the flask from the dropping funnel over a period of 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes to carry out a copolymerization reaction.
Thereafter, the atmosphere in the flask was replaced with air, and 51.2 parts of glycidyl methacrylate, 1.1 parts of triphenylphosphine, and 1.1 parts of methoquinone were added, and the reaction was continued for 10 hours at 120° C. to obtain a polymer. Finally, propylene glycol monomethyl ether acetate was added to the reaction solution so that the polymer solid concentration was 40%, to obtain a polymer solution. The ethylenic double bond equivalent of resin (B-8) was 1100 g/mol.

Synthesis Example 13: Preparation of Resin (B-9)
Into a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 492.4 parts of propylene glycol monomethyl ether acetate was added, and the mixture was stirred while replacing the atmosphere with nitrogen and heated to 90°C.
Next, a monomer mixture consisting of 208.1 parts of vinyltoluene, 62.1 parts of acrylic acid, and 13.0 parts of norbornene, to which 32.6 parts of dimethyl 2,2'-azobis(2-methylpropionate) and 5.7 parts of thioglycolic acid were added, was dropped into the flask from the dropping funnel over a period of 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes to carry out the copolymerization reaction.
Thereafter, the atmosphere in the flask was replaced with air, and 78.5 parts of glycidyl methacrylate, 1.1 parts of triphenylphosphine, and 1.1 parts of methoquinone were added, and the reaction was continued for 10 hours at 120° C. to obtain a polymer. Finally, propylene glycol monomethyl ether acetate was added to the reaction solution so that the polymer solid concentration was 40%, to obtain a polymer solution. The ethylenic double bond equivalent of resin (B-9) was 730 g/mol.

Synthesis Example 14: Preparation of Resin (B-10)
Into a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 547 parts of propylene glycol monomethyl ether acetate was added, and the mixture was stirred while replacing the atmosphere with nitrogen and heated to 120°C.
Next, a monomer mixture consisting of 272.0 parts of benzyl methacrylate and 73.8 parts of methacrylic acid, to which 4.2 parts of t-butylperoxy-2-ethylhexanoate had been added, was dropped into the flask from the dropping funnel over a period of 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes to carry out a copolymerization reaction, thereby obtaining a polymer. Propylene glycol monomethyl ether acetate was added to this reaction solution so that the polymer solid concentration became 35%, thereby obtaining a polymer solution.

Synthesis Example 15: Preparation of Resin (B-11)
A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 340 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C while stirring. Next, a mixed solution of 57 parts of acrylic acid, 54 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-yl acrylate (content ratio is 1:1 in molar ratio), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 40 parts of polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition of the initiator solution, the mixture was kept at 80°C for 3 hours and then cooled to room temperature to obtain a copolymer (resin (B-11)) solution having a solid content of 37.0% and a viscosity of 127 mPa·s measured with a Brookfield viscometer (23°C). The weight average molecular weight Mw of the produced copolymer was 9.4×10 ³ , the dispersity was 1.89, and the acid value calculated as solid content was 114 mg-KOH/g. Resin B-11 has the following structural units.

Synthesis Example 16: Preparation of Resin (B-12)
An appropriate amount of nitrogen was flowed into a 1 L flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 256 parts of propylene glycol monomethyl ether acetate was added and heated to 80° C. with stirring. Next, a mixed solution of 44 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-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.
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 completion of the dropwise addition, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B-12)) having a B-type viscosity (23°C) of 51 mPa·s and a solid content of 36.0%. The weight average molecular weight Mw of the produced copolymer was 11,000 and the dispersity was 1.98.

The polystyrene-equivalent weight average molecular weight Mw and number average molecular weight Mn of the resins obtained in the above Synthesis Examples were measured using a GPC method under the following conditions.
Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG2000HXL
Column temperature: 40°C
Solvent: Tetrahydrofuran Flow rate: 1.0 mL/min
Solids concentration of test solution: 0.001 to 0.01% by mass
Injection volume: 50 μL
Detector: RI
Calibration standard material: TSK STANDARD POLYSTYRENE
F-40, F-4, F-288, A-2500, A-500
(Manufactured by Tosoh Corporation)
The ratio of the weight average molecular weight and the number average molecular weight (Mw/Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

<Example 1 and Comparative Example 1>
(1) Preparation of Colored Curable Resin Composition The components shown in Table 1 were mixed in the amounts shown in Table 1 to obtain colored curable resin compositions. In preparing the colored curable resin composition, propylene glycol monomethyl ether acetate was mixed so that the solid content of the colored curable resin composition was 23.5 mass%. The unit of the amount of each component in Table 1 is "parts by mass", and the amounts of the colorant (A), resin (B), polymerizable compound (C), polymerization initiator (D), silane coupling agent, and leveling agent (F) are calculated as solid content.

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:

Colorant (A): Colored dispersion (A-1) (Table 1 shows the total amount of each pigment)
Resin (B): Resin (B-1)
Polymerizable compound (C): Polymerizable compound (C-1) (manufactured by Shin-Nakamura Chemical Co., Ltd., product name "NK Ester A-TMPT" trimethylolpropane triacrylate)

Polymerization initiator (D): Polymerization initiator (D-1) is a compound represented by the following formula (manufactured by BASF Ltd., product name "Irgacure OXE03")

Polymerization initiator (D): Polymerization initiator (D-2) Compound represented by the following formula

Silane coupling agent: Compound represented by the following formula, 3-methacryloxypropyltrimethoxysilane (trade name "KBM-503" manufactured by Shin-Etsu Chemical Co., Ltd.)

Leveling agent (F): Polyether modified silicone oil (product name "Toray Silicone SH8400" manufactured by Toray Dow Corning Co., Ltd.)

(The amounts of acrylic pigment dispersant and dispersing resin in Table 1 are those derived from colored dispersion (A-1).)

[Pattern Creation 1]
On a 4-inch glass wafer, each of the colored curable resin compositions shown in Table 1 was applied by spin coating so that the film thickness after post-baking was 1.2 μm, and then a colored composition layer was obtained. The substrate on which the colored composition layer was formed was irradiated with light at an exposure dose of 200 mJ/cm ² (based on 365 nm) using an exposure machine (NSR-1755i7A; manufactured by Nikon Corporation). As a photomask, one on which a dot pattern of 2.0 μm square was formed was used. The colored composition layer after light irradiation was immersed and developed in an aqueous developer containing tetramethylammonium hydroxide at 23 ° C. for 20 seconds, washed with water, and then post-baked at 90 ° C. for 15 minutes to obtain a pattern. The film thickness of the obtained pattern was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Shinku Gijutsu Co., Ltd.) and confirmed to be 1.2 μm.

<Example 2 and Comparative Example 2>
(1) Preparation of Colored Curable Resin Composition The components shown in Table 2 were mixed in the amounts shown in Table 2 to obtain colored curable resin compositions. In preparing the colored curable resin composition, propylene glycol monomethyl ether acetate was mixed so that the solid content of the colored curable resin composition was 14.0%. The unit of the amount of each component in Table 2 is "parts by mass", and the amounts of the colorant (A), resin (B), polymerizable compound (C), polymerization initiator (D), and leveling agent (F) are calculated as solid content.

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

Colorant (A): Colored dispersion (A-2) (Table 2 shows the total amount of each pigment)
Resin (B): Resin (B-2)

Polymerizable compound (C): Polymerizable compound (C-2) (manufactured by Toagosei Co., Ltd., product name "Aronix (registered trademark) M-930" glycerin triacrylate)

Polymerization initiator (D): Polymerization initiator (D-1) is a compound represented by the following formula (manufactured by BASF Ltd., product name "Irgacure OXE03")

Polymerization initiator (D): Polymerization initiator (D-2) Compound represented by the following formula

Leveling agent (F): Polyether modified silicone oil (product name "Toray Silicone SH8400" manufactured by Toray Dow Corning Co., Ltd.)

(The amounts of acrylic pigment dispersant and dispersing resin in Table 2 are those derived from colored dispersion (A-2).)

[Pattern Creation 2]
On a 2-inch square glass substrate (Eagle XG; manufactured by Corning), each colored curable resin composition described in Table 2 was applied by spin coating so that the film thickness after post-baking was 2.0 μm, and then pre-baked at 70 ° C. for 2 minutes to form a composition layer. After cooling, the substrate on which the composition layer was formed and a quartz glass photomask were spaced apart from each other by 50 μm, and the substrate was irradiated with light at an exposure dose of 100 mJ / cm ² (based on 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). Note that a photomask on which a 10 μm line and space pattern was formed was used. The composition layer after light irradiation was developed by immersing it in an aqueous solution containing 0.12% nonionic surfactant and 0.04% 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 Shinku Gijutsu Co., Ltd.) and was confirmed to be 2.0 μm.

[Evaluation of Solvent Resistance]
The patterns obtained by Pattern Preparation 1 and Pattern Preparation 2 were immersed in propylene glycol monomethyl ether acetate (PGMEA) or propylene glycol monomethyl ether (PGME) at 23° C. for 5 minutes and rinsed with running water for 10 seconds to conduct a solvent resistance test. Spectroscopic measurements were taken using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and evaluation was performed based on color difference and the film thickness retention (film thickness change) before and after the solvent resistance test was measured. The film thickness retention (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 and 4.

<Example 3 and Comparative Example 3>
(1) Preparation of Colored Curable Resin Compositions Colored curable resin compositions were obtained by mixing the components in the amounts shown in Table 5. In preparing the colored curable resin compositions, propylene glycol monomethyl ether acetate was mixed so that the solid content of the colored curable resin composition was 14.0%. The unit of the amount of each component 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 calculated as solid content.

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

[Pattern Creation 3]
On a 2-inch square glass substrate (Eagle XG; Corning), each colored curable resin composition described in Table 5 was applied by spin coating so that the film thickness after post-baking was 2.0 μm, and then pre-baked at 70 ° C. for 2 minutes to form a composition layer. After cooling, the substrate on which the composition layer was formed and a quartz glass photomask were spaced apart from each other by 50 μm, and the substrate was irradiated with light at an exposure dose of 100 mJ / cm ² (based on 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; Topcon Corporation). Note that a photomask on which a 10 μm line and space pattern was formed was used. The composition layer after light irradiation was developed by immersing it in an aqueous solution containing 0.12% nonionic surfactant and 0.04% 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 Shinku Gijutsu Co., Ltd.) and was confirmed to be 2.0 μm.

[Evaluation of Solvent Resistance]
The pattern obtained by pattern preparation 3 was immersed in propylene glycol monomethyl ether acetate (PGMEA) or propylene glycol monomethyl ether (PGME) at 23° C. for 5 minutes and rinsed with running water for 10 seconds to carry out a solvent resistance test. Spectroscopic measurements were taken using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and evaluation was performed based on color difference and the film thickness retention (film thickness change) before and after the solvent resistance test was measured. The film thickness retention (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.

<Test Examples 1 to 11>
(1) Preparation of Colored Curable Resin Compositions Colored curable resin compositions were obtained by mixing the components in the amounts shown in Table 7. In preparing the colored curable resin compositions, propylene glycol monomethyl ether acetate was mixed so that the solid content of the colored curable resin composition was 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 calculated as solid content.

The components (A-4), (B-X), (B-1), (B-3) to (B-12), (C-1), and (D-2) were the same as those described above, and the leveling agent (F) used was a polyether-modified silicone oil (manufactured by Dow Corning Toray Co., Ltd. under the trade name "Toray Silicone SH8400").
(The amounts of the acrylic pigment dispersant and dispersing resin in Table 7 are shown as amounts derived from the colored dispersion (A-4).)

[Pattern Creation 4]
On a 2-inch square glass substrate (Eagle XG; manufactured by Corning), each colored curable resin composition described in Table 7 was applied by spin coating so that the film thickness after post-baking was 2.0 μm, and then pre-baked at 70 ° C. for 2 minutes to form a composition layer. After cooling, the substrate on which the composition layer was formed and a quartz glass photomask were spaced apart from each other by 50 μm, and the substrate was irradiated with light at an exposure dose of 100 mJ / cm ² (based on 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). Note that a photomask on which a 10 μm line and space pattern was formed was used. The composition layer after light irradiation was developed by immersing it in an aqueous solution containing 0.12% nonionic surfactant and 0.04% 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 Shinku Gijutsu Co., Ltd.) and was confirmed to be 2.0 μm.

[Evaluation of Solvent Resistance]
The pattern obtained by pattern preparation 4 was immersed in propylene glycol monomethyl ether acetate (PGMEA) or propylene glycol monomethyl ether (PGME) at 23° C. for 5 minutes and rinsed with running water for 10 seconds to carry out a solvent resistance test. Spectroscopic measurements were taken using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and evaluation was performed based on color difference and the film thickness retention (film thickness change) before and after the solvent resistance test was measured. The film thickness retention (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.

Claims (13)

The composition includes a colorant, a resin, a polymerizable compound, and a polymerization initiator,
The colored curable resin composition, 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 represent a hydrocarbon group which may have a substituent.
n represents an integer of 0 to 4.
The --CH ₂ -- contained in the hydrocarbon group may be replaced with --O--, --S--, --CO--, or --OCO--. 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 the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond;
Resin [K2]: a copolymer having a structural unit derived from the (a), a structural unit derived from the (b), and a structural unit derived from a monomer (c) copolymerizable with the (a);
Resin [K3]: a copolymer having a structural unit derived from the (a) and a structural unit derived from the (c);
Resin [K4]: a copolymer having a structural unit derived from the (a) and a structural unit derived from the (b) by addition, and a structural unit derived from the (c);
Resin [K5]: a copolymer having a structural unit derived from the (b) to which the (a) has been added, and a structural unit derived from the (c);
Resin [K5']: a copolymer having a structural unit derived from the (a) and a structural unit derived from the (b) by addition, and a structural unit derived from the (c);
Resin [K6]: A copolymer having a structural unit obtained by adding the (a) to a structural unit derived from the (b) and further adding a carboxylic acid anhydride, and a structural unit derived from the (c). The colored curable resin composition according to claim 2, wherein the resin is resin [K1] and/or resin [K2]. The colored curable resin composition according to claim 2, wherein the resin is any one of resins [K2] to [K6] and contains, as the monomer (c), at least one selected from (meth)acrylic acid esters having a linear or branched aliphatic unsaturated hydrocarbon group, (meth)acrylic acid esters 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. The colored curable resin composition according to claim 2, wherein the resin is any one of resins [K4] to [K6]. 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. The colored curable resin composition according to claim 2, wherein the resin is any one of resins [K2] to [K4], the monomer (c) contains a (meth)acrylic acid ester having an aromatic ring, and the total of the structural units derived from the (meth)acrylic acid ester having an aromatic ring and the structural units derived from the (a) is 60 mol % or more out of 100 mol % of all structural units. the colorant comprises a green pigment and a yellow pigment;
The green pigment includes at least one selected from the group consisting of 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 comprises at least one selected from the group consisting of 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. The colored curable resin composition according to claim 2, comprising at least one pigment selected from the group consisting of 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. the colorant comprises a red pigment and a yellow pigment;
The red pigment includes at least one selected from the group consisting of 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 comprises at least one selected from the group consisting of 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. The colored curable resin composition according to claim 2, comprising at least one pigment selected from the group consisting of 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. The colorant includes a blue pigment and a purple pigment;
The blue pigment includes at least one selected from the group consisting of C.I. Pigment Blue 15, 15:3, 15:4, 15:6, and 16;
The colored curable resin composition according to claim 2, wherein the purple pigment comprises at least one selected from the group consisting of C. I. Pigment Violet 19, 23, and 29. A color filter formed from the colored curable resin composition according to any one of claims 1 to 10. A display device including the color filter according to claim 11. A solid-state imaging device including the color filter according to claim 11.