JP6098113B2 - Colored photosensitive resin composition - Google Patents

Description

  The present invention relates to a colored photosensitive resin composition.

Colored photosensitive resin compositions are used in the production of color filters used in display devices such as liquid crystal display panels, electroluminescence panels, and plasma display panels. As such a colored photosensitive resin composition, a colored photosensitive resin composition comprising a copolymer of methacrylic acid and 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate as a resin. A thing is known (patent document 1).

JP 2010-211198 A

  In order to form a colored pattern using a colored photosensitive resin composition, a colored photosensitive resin composition is applied to a substrate to form a composition layer, and the composition layer is exposed through a photomask and developed. Thus, a photolithography method is used in which a colored pattern is obtained. However, when the conventionally proposed colored photosensitive resin composition is used, when the unexposed portion of the composition layer is removed by development, the unexposed portion of the composition layer is removed so as to peel off. In some cases, the peeled pieces adhere to the colored pattern and become foreign matters.

［式（ｘ）中、Ｒ^ａ１は、水素原子又は炭素数１〜４のアルキル基を表す。
Ｒ^ａ２は、炭素数３〜１８の脂環式炭化水素基又は炭素数６〜１８の芳香族炭化水素基を表し、該脂環式炭化水素基及び該芳香族炭化水素基に含まれる水素原子は、炭素数１〜１０のアルキル基で置換されていてもよい。
Ｘ^ａ１は、単結合、−Ｘ^ａ２−、＊−（Ｘ^ａ２−Ｏ）_ｋ−、＊−Ｘ^ａ２−Ｓ−又は＊−Ｘ^ａ２−ＮＨ−を表す。＊はＯとの結合手を表す。
Ｘ^ａ２は、炭素数１〜６のアルカンジイル基を表す。
ｋは、１〜４の整数を表す。］
で表される単量体に由来する構造単位とを含む共重合体を含む樹脂であり、
式（ｘ）で表される単量体に由来する構造単位の含有量が、該共重合体を構成する構造単位全量に対して、１モル％以上８０モル％以下である着色感光性樹脂組成物。
［２］ 着色剤が、さらに顔料を含む［１］記載の着色感光性樹脂組成物。
［３］ ［１］又は［２］記載の着色感光性樹脂組成物により形成されるカラーフィルタ。
［４］ ［３］記載のカラーフィルタを含む表示装置。 The present invention includes the following inventions.
[1] including a colorant, a resin, a polymerizable compound, and a polymerization initiator,
The colorant contains a dye,
A monomer having a structural unit derived from at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride, a cyclic ether structure having 2 to 4 carbon atoms, and an ethylenically unsaturated bond A structural unit derived from the formula (x)

[In formula (x), R ^a1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
R ^a2 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group and the aromatic hydrocarbon group May be substituted with an alkyl group having 1 to 10 carbon atoms.
X ^a1 represents a single _{^{bond, -X a2 -, * - (}} X a2 -O) k -, * - X a2 -S- or ^* -X represents an a2 -NH-. * Represents a bond with O.
X ^a2 represents an alkanediyl group having 1 to 6 carbon atoms.
k represents an integer of 1 to 4. ]
A resin including a copolymer containing a structural unit derived from a monomer represented by:
Colored photosensitive resin composition wherein the content of structural units derived from the monomer represented by formula (x) is 1 mol% or more and 80 mol% or less with respect to the total amount of structural units constituting the copolymer object.
[2] The colored photosensitive resin composition according to [1], wherein the colorant further contains a pigment.
[3] A color filter formed from the colored photosensitive resin composition according to [1] or [2].
[4] A display device including the color filter according to [3].

  ADVANTAGE OF THE INVENTION According to this invention, it becomes possible to provide the coloring photosensitive resin composition which can reduce the foreign material on a coloring pattern.

［式（ｘ）中、Ｒ^ａ１は、水素原子又は炭素数１〜４のアルキル基を表す。
Ｒ^ａ２は、炭素数３〜１８の脂環式炭化水素基又は炭素数６〜１８の芳香族炭化水素基を表し、該脂環式炭化水素基及び該芳香族炭化水素基に含まれる水素原子は、炭素数１〜１０のアルキル基で置換されていてもよい。
Ｘ^ａ１は、単結合、−Ｘ^ａ２−、＊−（Ｘ^ａ２−Ｏ）_ｋ−、＊−Ｘ^ａ２−Ｓ−又は＊−Ｘ^ａ２−ＮＨ−を表す。＊はＯとの結合手を表す。
Ｘ^ａ２は、炭素数１〜６のアルカンジイル基を表す。
ｋは、１〜４の整数を表す。］
で表される単量体に由来する構造単位とを含む共重合体を含む樹脂である。
本発明の着色感光性樹脂組成物は、さらに、溶剤（Ｅ）を含むことが好ましい。
また、本発明の着色感光性樹脂組成物は、必要に応じて、重合開始助剤（Ｄ１）及び界面活性剤（Ｆ）からなる群から選ばれる少なくとも１種の成分を含んでもよい。
本明細書において、各成分として例示する化合物は、特に断りのない限り、単独で又は複数種を組合せて使用することができる。 The colored photosensitive resin composition of the present invention contains a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D).
The colorant (A) contains a dye (A1).
The resin (B) has a structural unit derived from at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride, a cyclic ether structure having 2 to 4 carbon atoms, and an ethylenically unsaturated bond. A structural unit derived from a monomer and the formula (x)

[In formula (x), R ^a1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
R ^a2 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group and the aromatic hydrocarbon group May be substituted with an alkyl group having 1 to 10 carbon atoms.
X ^a1 represents a single _{^{bond, -X a2 -, * - (}} X a2 -O) k -, * - X a2 -S- or ^* -X represents an a2 -NH-. * Represents a bond with O.
X ^a2 represents an alkanediyl group having 1 to 6 carbon atoms.
k represents an integer of 1 to 4. ]
It is resin containing the copolymer containing the structural unit derived from the monomer represented by these.
The colored photosensitive resin composition of the present invention preferably further contains a solvent (E).
Moreover, the colored photosensitive resin composition of this invention may contain the at least 1 sort (s) of component chosen from the group which consists of a polymerization start adjuvant (D1) and surfactant (F) as needed.
In this specification, unless otherwise indicated, the compound illustrated as each component can be used individually or in combination of multiple types.

<Colorant (A)>
The colorant (A) preferably contains a dye (A1) and further contains a pigment (A2).

The dye (A1) is not particularly limited, and a known dye can be used. Examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes, and dyes that can be dissolved in an organic solvent are preferable.
Examples of the dye (A1) include compounds classified as dyes by the Color Index (published by The Society of Dyers and Colorists) and known dyes described in Dyeing Notes (Color Dyeing). Also, according to chemical structure, azo dye, cyanine dye, triphenylmethane dye, phthalocyanine dye, anthraquinone dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine dye, styryl dye, coumarin dye, quinoline Examples thereof include dyes and nitro dyes. Of these, organic solvent-soluble dyes are preferred.

Specifically, C.I. I. Solvent Yellow 4 (hereinafter, description of CI Solvent Yellow is omitted, and only the number is described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99 117, 162, 163, 167, 189;
C. I. Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Solvent orange 2, 7, 11, 15, 26, 56, 77, 86;
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, 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 Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. I. Solvent dyes,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 41 , 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, 169, 173;
C. I. Acid Violet 6B, 7, 9, 17, 19, 30, 34, 102;
C. I. Acid Blue 1, 7, 9, 15, 18, 22, 23, 25, 27, 29, 40, 41, 42, 43, 45, 51, 54, 59, 60, 62, 70, 72, 74, 78, 80, 82, 83, 86, 87, 90, 92, 93, 96, 100, 102, 103, 104, 112, 113, 117, 120, 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, 229, 234, 236, 242, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340;
C. I. Acid Green 1, 3, 5, 9, 16, 25, 27, 28, 41, 50, 58, 63, 65, 80, 104, 105, 106, 109, etc. I. Acid dyes,
C. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141;
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, 6, 8, 15, 22, 25, 40, 41, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 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 green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, etc. I. Direct dyes,
C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse violet 26, 27;
C. I. Disperse Blue 1, 14, 56, 60, etc. I. Disperse dyes,
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;
C. I. C. such as Basic Green 1; I. Basic dyes,
C. I. Reactive Yellow 2, 76, 116;
C. I. Reactive Orange 16;
C. I. Reactive Red 36; I. Reactive dyes,
C. I. Modern yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modern Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 30, 32, 33, 36, 37, 38, 39 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95;
C. I. Modern 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. Modern violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58;
C. I. Modern 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. Modern Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, 53, etc. I. Modern dyes,
C. I. C. of Bat Green 1 etc. I. Examples include vat dyes.
These dyes can be used by appropriately selecting these dyes according to the desired spectral spectrum of the color filter.

As the dye (A1), a xanthene dye (Aa) is preferable.
The xanthene dye (Aa) is a dye containing a compound having a xanthene skeleton in the molecule. Examples of the xanthene dye (Aa) include C.I. I. Acid Red 51 (hereinafter, the description of CI Acid Red is omitted and only the number is described. Others are also the same), 52, 87, 91, 92, 94, 95, 98, 289, 388. , C.I. I. Acid Violet 9, 30, 102, C.I. I. Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, C.I. I. Basic Red 1, 10 (Rhodamine B), 11, C.I. I. Basic violet 10, 11, 25, C.I. I. Solvent Red 218, C.I. I. Modern Tread 27, C.I. I. Reactive red 36 (rose bengal B), sulforhodamine G, xanthene dyes described in JP 2010-32999 A, xanthene dyes described in Japanese Patent No. 4492760, and the like. Those that are soluble in organic solvents are preferred.

  Among these, as the xanthene dye (Aa), a dye containing a compound represented by the formula (1a) (hereinafter sometimes referred to as “compound (1a)”) is preferable. When using the compound (1a), the content of the compound (1a) in the xanthene dye (Aa) is preferably 50% by mass or more, more preferably 70% by mass or more, and further preferably 90% by mass or more. In particular, it is preferable to use only the compound (1a) as the xanthene dye (Aa).

［式（１ａ）中、Ｒ¹〜Ｒ⁴は、それぞれ独立に、水素原子、−Ｒ⁸又は置換基を有していてもよい炭素数６〜１０の１価の芳香族炭化水素基を表す。Ｒ¹及びＲ^２は、窒素原子と一緒になって窒素原子を含む環を形成してもよく、Ｒ^３及びＲ^４は、窒素原子と一緒になって窒素原子を含む環を形成してもよい。
Ｒ⁵は、−ＯＨ、−ＳＯ₃ ^-、−ＳＯ₃Ｈ、−ＳＯ₃ ^-Ｚ⁺、−ＣＯ₂Ｈ、−ＣＯ₂ ^-Ｚ⁺、−ＣＯ₂Ｒ⁸、−ＳＯ₃Ｒ⁸又は−ＳＯ₂ＮＲ⁹Ｒ¹⁰を表す。
Ｒ⁶及びＲ⁷は、それぞれ独立に、水素原子又は炭素数１〜６のアルキル基を表す。
ｍは、０〜５の整数を表す。ｍが２以上の整数である場合、複数のＲ⁵は同一であっても異なっていてもよい。
ａは、０又は１の整数を表す。
Ｘは、ハロゲン原子を表す。
Ｒ⁸は、炭素数１〜２０の１価の飽和炭化水素基を表し、該飽和炭化水素基に含まれる水素原子は、ハロゲン原子で置換されていてもよい。
Ｚ⁺は、⁺Ｎ（Ｒ¹¹）₄、Ｎａ⁺又はＫ⁺を表す。
Ｒ⁹及びＲ¹⁰は、それぞれ独立に、水素原子又は置換基を有していてもよい炭素数１〜２０の１価の飽和炭化水素基を表し、Ｒ⁹及びＲ¹⁰は、互いに結合して窒素原子と一緒に３〜１０員環の窒素含有複素環を形成していてもよい。
Ｒ¹¹は、それぞれ独立に、水素原子、炭素数１〜２０の１価の飽和炭化水素基又は炭素数７〜１０のアラルキル基を表す。］

[In Formula (1a), R ^{1 to} R ⁴ each independently represents a hydrogen atom, —R ^8, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms that may have a substituent. . R ¹ and R ² may be combined with a nitrogen atom to form a ring containing a nitrogen atom, and R ³ and R ⁴ may be combined with a nitrogen atom to form a ring containing a nitrogen atom. Good.
R ^{5 _{is, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8, -SO 3 R 8 or -SO ₂ represents NR ⁹ R ¹⁰
R ⁶ and R ⁷ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R ⁵ may be the same or different.
a represents an integer of 0 or 1.
X represents a halogen atom.
R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
Z ⁺ represents ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ .
R ⁹ and R ¹⁰ each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ⁹ and R ¹⁰ are bonded to each other. A 3- to 10-membered nitrogen-containing heterocyclic ring may be formed together with the nitrogen atom.
R ¹¹ each independently represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms. ]

Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms representing R ^{1 to} R ⁴ include a phenyl group, a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group.

In the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms representing R ^{1 to} R ⁴ , the hydrogen atom contained in the aromatic hydrocarbon group is a halogen atom, —R ⁸ , —OH, —OR ⁸ , _{^{-SO 3 -, -SO 3 H,}} -SO 3 - Z +, -CO 2 H, -CO 2 R 8, -SR 8, -SO 2 R 8, -SO 3 R 8 or -SO ₂ NR ⁹ R ^It may be substituted with ¹⁰ . Among these _{^{substituents, -SO 3 -, -SO 3 H}} , -SO 3 - is preferably at least one selected from Z ⁺ and the group consisting of _{^{-SO 2 NR 9 R 10, -SO}} 3 - Z + and More preferred is at least one selected from the group consisting of —SO ₂ NR ⁹ R ¹⁰ . In this case, —SO ₃ ^{− +} N (R ¹¹ ) ₄ is preferable as —SO ₃ ⁻ Z ⁺ . When R ^{1 to} R ⁴ are these groups, it is possible to form a color filter with less generation of foreign matter and excellent heat resistance from the colored curable resin composition containing the compound (1a).
R ¹ and R ² may be combined with a nitrogen atom to form a ring containing a nitrogen atom, and R ³ and R ⁴ may be combined with a nitrogen atom to form a ring containing a nitrogen atom. Good. Examples of the ring containing a nitrogen atom include the following.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms representing R ^{8 to} R ¹¹ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, Linear alkyl groups such as decyl group, dodecyl group, hexadecyl group, icosyl group; branched alkyl groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, 2-ethylhexyl group; cyclopropyl group, cyclopentyl group, C3-C20 alicyclic saturated hydrocarbon groups, such as a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a tricyclodecyl group, are mentioned.

Examples of —OR ⁸ include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, icosyloxy group and the like.

Examples of —CO ₂ R ⁸ include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.

Examples of —SR ⁸ include a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, and an icosylsulfanyl group.
Examples of —SO ₂ R ⁸ include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group.
Examples of —SO ₃ R ⁸ include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group.

—SO ₂ NR ⁹ R ¹⁰ includes, for example, a sulfamoyl group;
N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-methylbutyl) sulfamoyl group, N- (2-methylbutyl) sulfamoyl group, N- (3 -Methylbutyl) sulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl N- (1,3-dimethylbutyl) sulfamoyl group, N- (3,3-dimethylbutyl) sulfamoyl group, N-heptylsulfamoyl group, N- (1-methylhexyl) sulfamoyl group, N- (1 , 4-Dimethylpentyl) sulfamoyl group, N-octylsulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- (1,5-dimethyl) hexylsulfamoyl group, N- (1,1,2, , 2-tetramethylbutyl) sulfamoyl group and the like N-1 substituted sulfamoyl group;
N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-propylmethylsulfamoyl group, N, N-isopropylmethylsulfa Moyl group, N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis (1-methylpropyl) sulfamoyl group, N, N-heptylmethylsulfamoyl And N, N-2 substituted sulfamoyl groups such as a group.

In the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms representing R ⁹ and R ¹⁰ , a hydrogen atom contained in the saturated hydrocarbon group may be substituted with —OH or a halogen atom, and the saturated —CH ₂ — contained in the hydrocarbon group may be replaced by —O—, —CO—, —NH— or —NR ⁸ —.

R ⁹ and R ¹⁰ may be bonded to each other to form a 3- to 10-membered nitrogen-containing heterocycle together with the nitrogen atom. Examples of the heterocyclic ring include the following.

The alkyl group having 1 to 6 carbon atoms that represents the R ⁶ and R ^7, of the linear alkyl groups and branched alkyl groups listed above, include those having 1 to 6 carbon atoms.

Examples of the aralkyl group having 7 to 10 carbon atoms representing R ¹¹ include a benzyl group, a phenylethyl group, and a phenylbutyl group.

Z ⁺ is ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ¹¹ ) ₄ .
As the ⁺ N (R ¹¹ ) ₄ , at least two of the four R ¹¹ are preferably monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. The total number of carbon atoms of the four R ¹¹ is preferably 20 to 80, 20 to 60 is more preferable. When ⁺ N (R ¹¹ ) ₄ is present in the compound (1a), when R ¹¹ is any of these groups, the colored curable resin composition containing the compound (1a) can form a color filter with few foreign matters. .

  m is preferably 1 to 4, and more preferably 1 or 2.

  As the xanthene dye (Aa), a dye containing a compound represented by the formula (2a) (hereinafter sometimes referred to as “compound (2a)”) is more preferable. When the compound (2a) is used, the content of the compound (2a) in the xanthene dye (Aa) is preferably 50% by mass or more, more preferably 70% by mass or more, and further preferably 90% by mass or more.

［式（２ａ）中、Ｒ²¹〜Ｒ²⁴は、それぞれ独立に、水素原子、−Ｒ²⁶又は置換基を有していてもよい炭素数６〜１０の１価の置換基を有していてもよい芳香族炭化水素基を表す。Ｒ²¹及びＲ²²は、窒素原子と一緒になって窒素原子を含む環を形成してもよく、Ｒ²³及びＲ²⁴は、窒素原子と一緒になって窒素原子を含む環を形成してもよい。
Ｒ²⁵は、−ＳＯ₃ ^-、−ＳＯ₃Ｈ、−ＳＯ₃ ^-Ｚ１⁺又は−ＳＯ₂ＮＨＲ²⁶を表す。
ｍ１は、０〜５の整数を表す。ｍ１が２以上の整数である場合、複数のＲ²⁵は同一であっても異なっていてもよい。
ａ１は、０又は１の整数を表す。
Ｘ１は、ハロゲン原子を表す。
Ｒ²⁶は、炭素数１〜２０の１価の飽和炭化水素基を表す。
Ｚ１⁺は、⁺Ｎ（Ｒ²⁷）₄、Ｎａ⁺又はＫ⁺を表す。
Ｒ²⁷は、それぞれ独立に、炭素数１〜２０の１価の飽和炭化水素基又はベンジル基を表す。］

[In Formula (2a), R ^{21 to} R ²⁴ each independently have a hydrogen atom, —R ^26, or a monovalent substituent having 6 to 10 carbon atoms that may have a substituent. Represents a good aromatic hydrocarbon group. R ²¹ and R ²² may form a ring containing a nitrogen atom together with a nitrogen atom, and R ²³ and R ²⁴ may form a ring containing a nitrogen atom together with a nitrogen atom. Good.
R ²⁵ is, -SO ₃ ^- represents a Z1 ⁺ or _{^{-SO 2 NHR 26 -, -SO 3}} H, -SO 3.
m1 represents the integer of 0-5. When m1 is an integer of 2 or more, the plurality of R ²⁵ may be the same or different.
a1 represents an integer of 0 or 1.
X1 represents a halogen atom.
R ²⁶ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
Z1 ⁺ represents ⁺ N (R ²⁷ ) ₄ , Na ⁺ or K ⁺ .
R ²⁷ each independently represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a benzyl group. ]

Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms representing R ^{21 to} R ²⁴ include the same groups as those exemplified as the aromatic hydrocarbon group in R ^{1 to} R ⁴ . Hydrogen atoms contained in the aromatic hydrocarbon _{^{group, -SO 3 -, -SO 3 H}} , -SO 3 - Z1 +, may be substituted by -SO ₃ R ²⁶ or -SO ₂ NHR ^26.
As a combination of R ^{21 to} R ²⁴ , R ²¹ and R ²³ are hydrogen atoms, R ²² and R ²⁴ are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and the aromatic hydrocarbons hydrogen atoms contained in the _{^{groups, -SO 3 -, -SO 3 H}} , -SO 3 - Z1 +, those substituted by -SO ₃ R ²⁶ or -SO ₂ NHR ²⁶ preferred. A more preferred combination is that R ²¹ and R ²³ are hydrogen atoms, R ²² and R ²⁴ are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and hydrogen contained in the aromatic hydrocarbon group atom, -SO ₃ ^- in which are substituted with Z1 ⁺ or -SO ₂ NHR ^26.
R ²¹ and R ²² together with the nitrogen atom form an aliphatic heterocycle containing a nitrogen atom, and R ²³ and R ²⁴ together with the nitrogen atom contain an aliphatic heterocycle containing a nitrogen atom. Those forming a ring are preferred.
When R ^{21 to} R ²⁴ are these groups, a color filter having excellent heat resistance can be formed from the colored curable resin composition containing the compound (2a).

Examples of the aliphatic heterocycle include the following.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms representing R ²⁶ and R ²⁷ include the same groups as those exemplified as the saturated hydrocarbon group in R ^{8 to} R ¹¹ .
When R ^{21 to} R ²⁴ are —R ²⁶ , each of —R ²⁶ is preferably independently a methyl group or an ethyl group. As the R ²⁶ in -SO ₃ R ²⁶ and -SO ₂ NHR ^26, preferably branched alkyl group having 3 to 20 carbon atoms, more preferably a branched alkyl group having 6 to 12 carbon atoms, A 2-ethylhexyl group is more preferred. When R ²⁶ is these groups, a color filter with less generation of foreign matters can be formed from the colored curable resin composition containing the compound (2a).

Z1 ⁺ is ⁺ N (R ²⁷ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ²⁷ ) ₄ .
As the ⁺ N (R ²⁷ ) ₄ , at least two of the four R ²⁷ are preferably monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. The total number of carbon atoms of the four R ²⁷ is preferably 20 to 80, 20 to 60 is more preferable. When ⁺ N (R ²⁷ ) ₄ is present in the compound (2a), the colored curable resin composition containing the compound (2a) in which R ²⁷ is any of these groups can form a color filter with less generation of foreign matters. .

  m1 is preferably 1 to 4, and more preferably 1 or 2.

Examples of the compound (2a) include compounds represented by the formula (1-1) to the formula (1-25). In the formula, R ²⁶ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched alkyl group having 6 to 12 carbon atoms, and more preferably a 2-ethylhexyl group. Among these, C.I. I. Acid red 289 sulfonamidation product, C.I. I. Quaternary ammonium salt of Acid Red 289, C.I. I. Acid violet 102 sulfonamidate or C.I. I. The quaternary ammonium salt of Acid Violet 102 is preferred. Examples of such a compound include compounds represented by formula (1-1) to formula (1-8), formula (1-11), and formula (1-12).

  Moreover, as a xanthene dye (Aa), the dye containing the compound (henceforth "compound (3a)") represented by Formula (3a) is also more preferable. When the compound (3a) is used, the content of the compound (3a) in the xanthene dye (Aa) is preferably 50% by mass or more, more preferably 70% by mass or more, and further preferably 90% by mass or more.

［式（３ａ）中、Ｒ³¹及びＲ³²は、互いに独立に、炭素数１〜４のアルキル基を表す。
Ｒ³³及びＲ³⁴は、互いに独立に、炭素数１〜４のアルキル基、炭素数１〜４のアルキルスルファニル基又は炭素数１〜４のアルキルスルホニル基を表す。
Ｒ³¹及びＲ³³は、窒素原子と一緒になって窒素原子を含む環を形成してもよく、Ｒ³²及びＲ³⁴は、窒素原子と一緒になって窒素原子を含む環を形成してもよい。
ｐ及びｑは、互いに独立に、０〜５の整数を表す。ｐが２以上である場合、複数のＲ³³は同一でも異なってもよく、ｑが２以上である場合、複数のＲ³⁴は同一でも異なってもよい。］

[In formula (3a), R ³¹ and R ³² each independently represent an alkyl group having 1 to 4 carbon atoms.
R ^<33> and R ^<34 > represent a C1-C4 alkyl group, a C1-C4 alkylsulfanyl group, or a C1-C4 alkylsulfonyl group mutually independently.
R ³¹ and R ³³ may form a ring containing a nitrogen atom together with a nitrogen atom, and R ³² and R ³⁴ may form a ring containing a nitrogen atom together with a nitrogen atom. Good.
p and q represent the integer of 0-5 mutually independently. When p is 2 or more, the plurality of R ³³ may be the same or different, and when q is 2 or more, the plurality of R ³⁴ may be the same or different. ]

Examples of the alkyl group having 1 to 4 carbon atoms representing R ³¹ , R ³² , R ³³ and R ³⁴ include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Groups and the like.
Examples of the alkylsulfanyl group having 1 to 4 carbon atoms representing R ³³ and R ³⁴ include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, a butylsulfanyl group, and an isopropylsulfanyl group.
Examples of the alkylsulfonyl group having 1 to 4 carbon atoms representing R ³³ and R ³⁴ include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, and an isopropylsulfonyl group.
R ³¹ and R ³² are preferably each independently an alkyl group having 1 to 3 carbon atoms. R ³³ and R ³⁴ are preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
p and q are each independently preferably an integer of 0 to 2, and more preferably 1 or 2.

  Examples of compound (3a) include compounds represented by formula (1-26) to formula (1-35), respectively. Especially, the compound represented by Formula (1-26)-Formula (1-32) is preferable at the point which is excellent in the solubility to an organic solvent.

  As the xanthene dye (Aa), a commercially available xanthene dye (for example, “Chugai Aminol Fast Pink RH / C” manufactured by Chugai Kasei Co., Ltd., “Rhodamin 6G” manufactured by Taoka Chemical Industry Co., Ltd.) may be used. it can. Moreover, it can also synthesize | combine with reference to Unexamined-Japanese-Patent No. 2010-32999 using the commercially available xanthene dye as a starting material.

The pigment (A2) is not particularly limited, and a known pigment can be used, and examples thereof include compounds classified as pigments by the color index (published by The Society of Dyers and Colorists).
Examples of the pigment include C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 180, 185, 194, 214, 219;
C. I. Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 175, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, etc. Pigments;
C. I. Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60, 80; I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38;
C. I. Green pigments such as CI Pigment Green 7, 36, 58;
C. I. Brown pigments such as CI Pigment Brown 23 and 25;
C. I. And black pigments such as CI Pigment Black 1 and 7.

  Examples of the pigment include C.I. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 (blue pigment), C.I. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 (violet color pigment) are preferable, and C.I. I. Pigment blue 15: 3, 15: 6, C.I. I. Pigment Violet 23 is more preferable, and C.I. I. Pigment Blue 15: 6 is more preferable. By including the pigment, the transmission spectrum can be easily optimized, and the light resistance and chemical resistance of the color filter are improved.

Pigment (A2) is optionally treated with rosin, surface treatment using a pigment derivative having an acidic group or basic group introduced, grafting onto the pigment surface with a polymer compound, sulfuric acid atomization method, etc. May be subjected to the atomization treatment by, cleaning treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method, or the like.
The pigment (A2) preferably has a uniform particle size. By carrying out a dispersion treatment by containing a pigment dispersant, a pigment dispersion in which the pigment is uniformly dispersed in the solution can be obtained.

Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. As the pigment dispersant, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Geneca Co., Ltd.), EFKA (manufactured by CIBA), Ajispur (Ajinomoto Fine) (Techno Co., Ltd.), Disperbyk (Bic Chemie) and the like.
When the pigment dispersant is used, the amount used is preferably 1% by mass or more and 100% by mass or less, and more preferably 5% by mass or more and 50% by mass or less with respect to the pigment (A2). When the amount of the pigment dispersant used is in the above range, there is a tendency that a pigment dispersion in a uniform dispersion state is obtained.

  The colorant (A) preferably contains a dye (A1) and a pigment (A2). In this case, the content ratio of the dye (A1) and the pigment (A2) is preferably from 1:99 to 99: 1, more preferably from 3:97 to 90:10, based on mass. By setting such a ratio, the transmission spectrum can be easily optimized, and the resulting color filter tends to be excellent in contrast, brightness, heat resistance, and chemical resistance.

  In particular, the colorant (A) is preferably a colorant containing a xanthene dye (Aa) and a blue pigment. I. A coloring agent containing CI Pigment Blue 15: 6 is more preferable. The content ratio of the xanthene dye (Aa) and the blue pigment is, on a mass basis, preferably 1:99 to 90:10, more preferably 2:98 to 70:30, and further preferably 2:98 to 50:50.

The content of the colorant (A) is preferably 5 to 60% by mass, more preferably 8 to 50% by mass, and further preferably 10 to 40% by mass with respect to the total amount of the solid content. When the content of the colorant (A) is within the above range, the color density when it is used as a color filter is sufficient, and the resin (B) and the polymerizable compound (C) are contained in a necessary amount in the composition. Therefore, a color filter having sufficient mechanical strength can be formed.
Here, the “total amount of solids” in this specification refers to an amount obtained by removing the content of the solvent from the total amount of the colored photosensitive resin composition of the present invention. The total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography, for example.

［式（ｘ）中、Ｒ^ａ１は、水素原子又は炭素数１〜４のアルキル基を表す。
Ｒ^ａ２は、炭素数３〜１８の脂環式炭化水素基又は炭素数６〜１８の芳香族炭化水素基を表し、該脂環式炭化水素基及び該芳香族炭化水素基に含まれる水素原子は、炭素数１〜１０のアルキル基で置換されていてもよい。
Ｘ^ａ１は、単結合、−Ｘ^ａ２−、＊−（Ｘ^ａ２−Ｏ）_ｋ−、＊−Ｘ^ａ２−Ｓ−又は＊−Ｘ^ａ２−ＮＨ−を表す。＊はＯとの結合手を表す。
Ｘ^ａ２は、炭素数１〜６のアルカンジイル基を表す。
ｋは、１〜４の整数を表す。］
で表される単量体（以下「（ｘ）」という場合がある）に由来する構造単位とを含む共重合体（以下「共重合体（Ｂ１）」という場合がある）を含み、（ｘ）に由来する構造単位の含有量は、該共重合体（Ｂ１）を構成する構造単位全量に対して、１モル％以上８０モル％以下である。 <Resin (B)>
The resin (B) is a structural unit derived from at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (hereinafter sometimes referred to as “(a)”), and has 2 to 4 carbon atoms. A structural unit derived from a monomer having a cyclic ether structure and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”), and the formula (x)

[In formula (x), R ^a1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
R ^a2 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group and the aromatic hydrocarbon group May be substituted with an alkyl group having 1 to 10 carbon atoms.
X ^a1 represents a single _{^{bond, -X a2 -, * - (}} X a2 -O) k -, * - X a2 -S- or ^* -X represents an a2 -NH-. * Represents a bond with O.
X ^a2 represents an alkanediyl group having 1 to 6 carbon atoms.
k represents an integer of 1 to 4. ]
And a copolymer (hereinafter sometimes referred to as “copolymer (B1)”) containing a structural unit derived from a monomer represented by (hereinafter also referred to as “(x)”), (x The content of the structural unit derived from) is 1 mol% or more and 80 mol% or less with respect to the total amount of the structural unit constituting the copolymer (B1).

  Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group.

炭素数１〜１０のアルキル基を有する脂環式炭化水素基としては、３，３，５−トリメチルシクロヘキシル基、イソボルニル基、メチルアダマンチル基等が挙げられる。 Examples of the alicyclic hydrocarbon group having 3 to 18 carbon atoms representing R ^a2 include a monocyclic alicyclic carbon group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. A hydrogen group;
Examples thereof include polycyclic alicyclic hydrocarbon groups such as groups represented by the following formulae.

Examples of the alicyclic hydrocarbon group having an alkyl group having 1 to 10 carbon atoms include 3,3,5-trimethylcyclohexyl group, isobornyl group, and methyladamantyl group.

Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms include a phenyl group, a naphthyl group, an anthryl group, and a phenanthryl group.
Examples of the aromatic hydrocarbon group having an alkyl group having 1 to 10 carbon atoms include a toluyl group, a xylyl group, a mesityl group, a butylphenyl group, and a nonylphenyl group. When the hydrogen atom bonded to the aromatic ring of the aromatic hydrocarbon group is substituted with an alkyl group having 1 to 10 carbon atoms, the carbon number of the aromatic hydrocarbon group includes the carbon number of the alkyl group. Absent.

Examples of the alkanediyl group having 1 to 6 carbon atoms 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, and a pentane-1,5. -A diyl group, a hexane-1, 6-diyl group, etc. are mentioned.
_{^{* - (X a2 -O) k}} -, * - X a2 -S- and ^* -X a2 ^{X a2} in the -NH- is an ethylene group or propane-1,2-diyl group are preferable.
When X ^a1 is —X ^a2 —, X ^a2 is preferably a methylene group or an ethylene group, and more preferably a methylene group.

R ^a1 is preferably a hydrogen atom or a methyl group.
R ^a2 is preferably an alicyclic hydrocarbon group having 5 to 18 carbon atoms or an aralkyl group having 7 to 18 carbon atoms, and a polycyclic alicyclic hydrocarbon group having 5 to 18 carbon atoms or 7 carbon atoms. It is more preferably a -18 aralkyl group, and further preferably a polycyclic alicyclic hydrocarbon group having 5 to 10 carbon atoms or an aralkyl group having 7 to 11 carbon atoms.
X ^a1 is preferably a single bond, —X ^a2 — or * — (X ^a2 —O) _k —, more preferably a single bond or —X ^a2 —, and a single bond or a methylene group. Is more preferable.

Examples of (x) in which R ^a2 is an alicyclic hydrocarbon group having 3 to 18 carbon atoms include cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, 3,3,5- Trimethylcyclohexyl (meth) acrylate, bicyclo [2.2.1] heptan-2-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate In the field, it is referred to as “dicyclopentanyl (meth) acrylate” as a common name, and sometimes referred to as “tricyclodecyl (meth) acrylate”), tricyclo [5.2.1.0 ^{2, 6]} decene-8-yl (meth) acrylate (in the art, "dicyclopentenyl (meth) acrylate as a trivial name It is said that.), 2- (tricyclo [5.2.1.0 ^2,6] decan-8-yloxy) ethyl (meth) acrylate, 2- (tricyclo [5.2.1.0 ^2,6 ] Decan-8-ylsulfanyl) ethyl (meth) acrylate, 2- (tricyclo [5.2.1.0 ^2,6 ] decan-8-ylamino) ethyl (meth) acrylate, 4- (tricyclo [5.2 .1.0 ^2,6 ] decan-8-yloxy) butyl (meth) acrylate, 6- (tricyclo [5.2.1.0 ^2,6 ] decan-8-yloxy) hexyl (meth) acrylate, isobornyl ( And meth) acrylate and adamantyl (meth) acrylate.
In the present specification, “(meth) acryloyl” represents at least one selected from the group consisting of acryloyl and methacryloyl. Notations such as “(meth) acrylic acid” and “(meth) acrylate” have the same meaning.

Examples of (x) where R ^a2 is an aromatic hydrocarbon group having 6 to 18 carbon atoms include phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, 2 Examples include-(4-nonylphenoxy) ethyl (meth) acrylate, a compound represented by the following formula, and the like.

(X) includes cyclohexyl (meth) acrylate, bicyclo [2.2.1] heptan-2-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meta ) Acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, and benzyl (meth) acrylate are preferred, and tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate, benzyl (meth). Acrylate is more preferred. When (x) is such a monomer, the film coated with the colored photosensitive resin composition is excellent in solubility in an organic solvent, and therefore, for example, precipitation in a pipe or a discharge part inside the coating apparatus can be suppressed. Tend.

As (a), unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid;
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, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo Bicyclounsaturated compounds containing a carboxy group such as [2.2.1] hept-2-ene, 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Unsaturated dicarboxylic acid anhydrides such as tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride (hymic acid anhydride);
Unsaturated mono [(meth) acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as succinic acid mono [2- (meth) acryloyloxyethyl] and phthalic acid mono [2- (meth) acryloyloxyethyl] Kind;
Examples thereof include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α- (hydroxymethyl) acrylic acid.
Of these, acrylic acid, methacrylic acid, and maleic anhydride are preferred from the viewpoint of copolymerization reactivity and solubility in an aqueous alkali solution.

  As (b), 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. Is mentioned. (B) is preferably a monomer having a C2-C4 cyclic ether and a (meth) acryloyloxy group.

  Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), and a single monomer having an oxetanyl group and an ethylenically unsaturated bond. Monomer (b2) (hereinafter sometimes referred to as “(b2)”), and monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b3)”). It is done.

  (B1) is, for example, a monomer (b1-1) having a structure in which a linear or branched unsaturated aliphatic hydrocarbon is epoxidized (hereinafter referred to as “(b1-1)”) And a monomer (b1-2) having a structure in which an unsaturated alicyclic hydrocarbon is epoxidized (hereinafter may be referred to as “(b1-2)”).

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

  Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide 2000; manufactured by Daicel Chemical Industries, Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate ( For example, Cyclomer A400 (manufactured by Daicel Chemical Industries, Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer M100; manufactured by Daicel Chemical Industries, Ltd.), represented by formula (I) Examples thereof include compounds and compounds represented by the formula (II).

[In Formula (I) and Formula (II), R ^b1 and R ^b2 represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with a hydroxy group. May be.
X ^b1 and X ^b2 represents a single ^{bond, -R b3 -, * - R} b3 -O -, * - R b3 -S- or * -R ^b3 represents a -NH-.
R ^b3 represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with 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 hydroxy include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy Examples include a -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 ^b1 and R ^b2 are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group or a 2-hydroxyethyl group, more preferably a hydrogen atom or a methyl group.

Examples of alkanediyl groups include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane- Examples include 1,6-diyl group.
X ^b1 and X ^b2 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, * —CH _2. CH ₂ —O— can be mentioned. * Represents a bond with O.

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

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

  The compound represented by the formula (I) and the compound represented by the formula (II) may be used singly or as a mixture in any ratio. When used as a mixture, the content ratio of the compound represented by the formula (I) and the compound represented by the formula (II) is preferably 5:95 to 95: 5, more preferably 10:90 to 5 on a molar basis. 90:10, more preferably 20:80 to 80:20.

  (B2) is more preferably a monomer having an oxetanyl group and a (meth) acryloyloxy group. (B2) includes 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane , 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, 3-ethyl-3-acryloyloxyethyl oxetane, and the like.

  (B3) is more preferably a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

  (B) is preferably (b1) in that the color filter obtained can have higher reliability such as heat resistance and chemical resistance. Furthermore, (b1-2) is more preferable in that the storage stability of the colored photosensitive resin composition is excellent.

Further, the copolymer (B1) is different from (a), (b) and (x) and is derived from a monomer copolymerizable with these (hereinafter sometimes referred to as “(c)”). You may have a structural unit.
Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, allyl (meth) acrylate, (Meth) acrylic acid esters such as propargyl (meth) acrylate;
Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconate;

  Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2′-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-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. .1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept-2-ene, 5-phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5,6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept-2-ene, 5,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene Bicyclo unsaturated compounds;

  N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate, N- (9-acridinyl) maleimide;

Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyl toluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene , Isoprene, and 2,3-dimethyl-1,3-butadiene.
Of these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, and bicyclo [2.2.1] hept-2-ene are preferable from the viewpoints of copolymerization reactivity and heat resistance. .

When the copolymer (B1) is a copolymer comprising a structural unit derived from (x), a structural unit derived from (a), and a structural unit derived from (b), The content ratio is based on the total amount of structural units constituting the copolymer.
Structural unit derived from (x); 1 to 80 mol%
Structural unit derived from (a); 2-45 mol%
Structural unit derived from (b); 2 to 95 mol%
Is preferred,
Structural unit derived from (x); 1 to 65 mol%
Structural unit derived from (a); 5 to 40 mol%
Structural unit derived from (b); 5 to 80 mol%
Is more preferred,
Structural unit derived from (x); 5-55 mol%
Structural unit derived from (a); 10 to 40 mol%
Structural unit derived from (b); 5-55 mol%
Is more preferable.
When the ratio of each structural unit is within the above range, in the composition layer formed from the colored photosensitive resin composition, unexposed part peeling at the time of development is suppressed, and the generation of foreign matters tends to be reduced. There is.

The copolymer (B1) is a copolymer comprising a structural unit derived from (x), a structural unit derived from (a), a structural unit derived from (b), and a structural unit derived from (c). In this case, the content ratio of the structural units derived from each is based on the total amount of structural units constituting the copolymer,
Structural unit derived from (x); 1 to 80 mol%
Structural unit derived from (a); 2-45 mol%
Structural unit derived from (b); 2 to 95 mol%
Structural unit derived from (c); 2 to 80 mol%
Is preferred,
Structural unit derived from (x); 1 to 65 mol%
Structural unit derived from (a); 5 to 40 mol%
Structural unit derived from (b); 5 to 80 mol%
Structural unit derived from (c); 2 to 65 mol%
Is more preferred,
Structural unit derived from (x); 5-55 mol%
Structural unit derived from (a); 10 to 40 mol%
Structural unit derived from (b); 5-50 mol%
Structural unit derived from (c); 2 to 40 mol%
Is more preferable.
When the ratio of each structural unit is within the above range, in the composition layer formed from the colored photosensitive resin composition, unexposed part peeling at the time of development is suppressed, and the generation of foreign matters tends to be reduced. There is.

  The copolymer (B1) can be prepared by, for example, the method described in the document “Experimental Method for Polymer Synthesis” (Takayuki Otsu published by Kagaku Dojin Co., Ltd., 1st edition, 1st edition, published on March 1, 1972) and It can manufacture with reference to the cited reference described in the said literature.

  Specifically, a predetermined amount of (x), (a), (b) and, if necessary, (c), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and, for example, nitrogen is substituted with oxygen. Thus, there is a method of heating and keeping warm while stirring in a deoxygenated atmosphere. In addition, the polymerization initiator, the solvent, and the like used here are not particularly limited, and those usually used in the field can be used. Examples of the polymerization initiator include azo compounds (2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.). As the solvent, any solvent that dissolves each monomer may be used, and examples of the solvent for the colored photosensitive resin composition include a solvent (E) described later.

  In addition, the obtained copolymer may use the solution after reaction as it is, a concentrated or diluted solution may be used, and it took out as solid (powder) by methods, such as reprecipitation. Things may be used. In particular, by using a solvent (E) described later as a solvent in the polymerization, the solution after the reaction can be used as it is, and the manufacturing process can be simplified.

The polystyrene equivalent weight average molecular weight of the copolymer (B1) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and further preferably 5,000 to 30,000. It is. When the molecular weight is in the above range, the hardness of the color filter is improved, the residual film ratio is high, the solubility of the unexposed portion in the developer is good, and the resolution tends to be improved.
The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the copolymer (B1) is preferably 1.1 to 6, and more preferably 1.2 to 4.

  The acid value of the copolymer (B1) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150, and still more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin, and can be determined by titration using, for example, an aqueous potassium hydroxide solution.

The resin (B) may include a resin different from the copolymer (B1) (hereinafter sometimes referred to as “resin (B2)”). The resin (B2) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B2) include the following resins [K1] to [K6].
Resin [K1]: Copolymer of (a) and (b);
Resin [K2]: Copolymer of (a), (b) and (c);
Resin [K3]: a copolymer of (a) and a monomer that is copolymerizable with (a) and that is different from (a) and (b) (hereinafter sometimes referred to as “(c ′)”) Polymer;
Resin [K4]: a resin obtained by reacting (b) with a copolymer of (a) and (c ′);
Resin [K5]: a resin obtained by reacting (a) with a copolymer of (b) and (c ′);
Resin [K6]: A resin obtained by reacting (a) with a copolymer of (b) and (c ′) and further reacting with a carboxylic acid anhydride.
Here, examples of (c ′) include the monomers exemplified in the above (x) and (c).

In the resin [K1], the ratio of the structural units derived from each is relative to all the structural units constituting the resin [K1].
Structural unit derived from (a); 2 to 60 mol%
Structural unit derived from (b); 40-98 mol%
Is preferred,
Structural unit derived from (a); 10-50 mol%
Structural unit derived from (b); 50-90 mol%
Is more preferable.
When the ratio of the structural unit of the resin [K1] is in the above range, the colored photosensitive resin composition is excellent in storage stability, developability when forming a colored pattern, and solvent resistance of the resulting colored pattern. Tend.

  Resin [K1] can be produced, for example, in the same manner as described for the production method of copolymer (B1).

In the resin [K2], the ratio of the structural units derived from each of the structural units in the resin [K2]
Structural unit derived from (a); 2-45 mol%
Structural unit derived from (b); 2 to 95 mol%
Structural unit derived from (c); 1 to 65 mol%
It is preferable that
Structural unit derived from (a); 5 to 40 mol%
Structural unit derived from (b); 5 to 80 mol%
Structural unit derived from (c); 5 to 60 mol%
It is more preferable that
When the ratio of the structural unit of the resin [K2] is in the above range, the storage stability of the colored photosensitive resin composition, the developability when forming the colored pattern, and the solvent resistance of the resulting colored pattern, There is a tendency to be excellent in heat resistance and mechanical strength.

  Resin [K2] can be produced, for example, in the same manner as described for the production method of copolymer (B1).

In the resin [K3], the proportion of structural units derived from each of the structural units constituting the resin [K3]
Structural unit derived from (a); 2 to 60 mol%
Structural unit derived from (c ′); 40 to 98 mol%
It is preferable that
Structural unit derived from (a); 10-50 mol%
Structural unit derived from (c ′); 50-90 mol%
It is more preferable that
Resin [K3] can be produced, for example, in the same manner as described in the method for producing copolymer (B1).

Resin [K4] obtains a copolymer of (a) and (c ′), and (b) has a carboxylic acid and / or carboxylic acid anhydride having (a) a cyclic ether having 2 to 4 carbon atoms. It can be manufactured by adding to a product.
First, a copolymer of (a) and (c ′) is produced in the same manner as the method described as the production method of the copolymer (B1). In this case, it is preferable that the ratio of the structural units derived from each is the same as that described for the resin [K3].

Next, the C2-C4 cyclic ether which (b) has is reacted with a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer.
Subsequent to the production of the copolymer of (a) and (c ′), the atmosphere in the flask is replaced with nitrogen to air, and (b) a reaction catalyst (for example, tris) of carboxylic acid or carboxylic anhydride and cyclic ether is used. (Dimethylaminomethyl) phenol, etc.) and a polymerization inhibitor (eg, hydroquinone, etc.) are placed in a flask and reacted, for example, at 60-130 ° C. for 1-10 hours to produce resin [K4]. Can do.
The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By making it in this range, the storage stability of the colored photosensitive resin composition, the developability when forming the colored pattern, and the balance of the solvent resistance, heat resistance, mechanical strength and sensitivity of the resulting colored pattern are good. Tend to be. Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, (b1) is preferable as (b) used for the resin [K4], and (b1-1) is more preferable.
The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b) and (c ′). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b) and (c ′).
The reaction conditions such as the charging method, reaction temperature, and time can be appropriately adjusted in consideration of the production equipment and the amount of heat generated by polymerization. In addition, like the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, and the like.

Resin [K5] obtains a copolymer of (b) and (c ′) as the first step, as in the method described as the method for producing copolymer (B1). Similarly to the above, the obtained copolymer may be used as it is after the reaction, or may be a concentrated or diluted solution, or may be solid (powder) by a method such as reprecipitation. You may use what was taken out as.
The ratio of the structural units derived from (b) and (c ′) is preferably in the following range with respect to the total number of moles of all structural units constituting the copolymer.
Structural unit derived from (b); 5-95 mol%
Structural unit derived from (c ′); 5-95 mol%
It is preferable that
Structural unit derived from (b); 10-90 mol%
Structural unit derived from (c ′); 10 to 90 mol%
It is more preferable that

Furthermore, the carboxylic acid or carboxylic acid possessed by (a) is added to the cyclic ether derived from (b) possessed by the copolymer of (b) and (c ′) under the same conditions as in the resin [K4] production method. Resin [K5] can be obtained by reacting an anhydride.
As for the usage-amount of (a) made to react with the said copolymer, 5-80 mol is preferable with respect to 100 mol of (b). Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, (b1) is preferable as (b) used for the resin [K5], and (b1-1) is more preferable.

Resin [K6] is a resin obtained by further reacting carboxylic anhydride with resin [K5]. Carboxylic anhydride is reacted with a hydroxy group generated by reaction of cyclic ether with carboxylic acid or carboxylic anhydride.
Carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride (highmic acid anhydride) and the like. It is done. As for the usage-amount of carboxylic acid anhydride, 0.5-1 mol is preferable with respect to 1 mol of usage-amount of (a).

Examples of the resin (B2) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate / Resins such as (meth) acrylic acid copolymers [K1];
Glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate / (meth) acrylic acid / N-cyclohexylmaleimide Polymer, resin such as 3-methyl-3- (meth) acryloyloxymethyloxetane / (meth) acrylic acid / N-cyclohexylmaleimide copolymer [K2];
Resins [K3] such as benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer;
Resin prepared by adding glycidyl (meth) acrylate to benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate to tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer Resin such as tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer added with glycidyl (meth) acrylate resin [K4];
Resin obtained by reacting tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate copolymer with (meth) acrylic acid, tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate copolymer ( Resins such as resins reacted with (meth) acrylic acid [K5];
Resin [K6] such as a resin obtained by reacting a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate with (meth) acrylic acid and further reacting with tetrahydrophthalic anhydride. .

  Especially, as resin (B2), resin [K1], resin [K2], and resin [K3] are preferable.

The polystyrene equivalent weight average molecular weight of the resin (B2) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and further preferably 5,000 to 30,000. . When the molecular weight is in the above range, the hardness of the color filter is improved, the residual film ratio is high, the solubility of the unexposed portion in the developer is good, and the resolution tends to be improved.
The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B2) is preferably 1.1 to 6, and more preferably 1.2 to 4.

  The acid value of the resin (B2) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150, and still more preferably 70 to 135 mg-KOH / g.

  The resin (B) may be only the copolymer (B1), but when the resin (B2) is included, the content thereof is preferably 1 to 95% by mass with respect to the total amount of the resin (B). Preferably it is 5-90 mass%.

  Content of resin (B) becomes like this. Preferably it is 7-65 mass% with respect to the total amount of solid content, More preferably, it is 13-60 mass%, More preferably, it is 17-55 mass%. When the content of the resin (B2) is within the above range, the resolution of the colored pattern and the remaining film rate tend to be improved.

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by heat or an active radical and / or acid generated from the polymerization initiator (D). For example, a compound having a polymerizable ethylenically unsaturated bond is used. Preferably, it is a (meth) acrylic acid ester compound.

The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds.
Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa ( (Meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl) ) Isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified dipentaerythritol Hexa (meth) acrylate, propylene glycol modified pentaerythritol tetra (meth) acrylate, propylene glycol modified dipentaerythritol hexa (meth) acrylate, caprolactone modified pentaerythritol tetra (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) acrylate Can be mentioned.
Of these, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate are preferable.

  The weight average molecular weight of the polymerizable compound (C) is preferably from 150 to 2,900, more preferably from 250 to 1,500.

  The content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 55% by mass with respect to the total amount of the solid content. is there. When the content of the polymerizable compound (C) is in the above range, the remaining film ratio and chemical resistance of the colored pattern tend to be improved.

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating an active radical, an acid or the like by the action of light or heat and initiating polymerization, and a known polymerization initiator can be used.
The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of O-acyl oxime compounds, alkylphenone compounds, triazine compounds, acyl phosphine oxide compounds and biimidazole compounds. More preferred is a polymerization initiator containing a sulfur compound.

Ｏ−アシルオキシム化合物としては、例えば、Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）ブタン−１−オン−２−イミン、Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）オクタン−１−オン−２−イミン、Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）−３−シクロペンチルプロパン−１−オン−２−イミン、Ｎ−アセトキシ−１−［９−エチル−６−（２−メチルベンゾイル）−９Ｈ−カルバゾール−３−イル］エタン−１−イミン、Ｎ−アセトキシ−１−［９−エチル−６−｛２−メチル−４−（３，３−ジメチル−２，４−ジオキサシクロペンタニルメチルオキシ）ベンゾイル｝−９Ｈ−カルバゾール−３−イル］エタン−１−イミン、Ｎ−アセトキシ−１−［９−エチル−６−（２−メチルベンゾイル）−９Ｈ−カルバゾール−３−イル］−３−シクロペンチルプロパン−１−イミン、Ｎ−ベンゾイルオキシ−１−［９−エチル−６−（２−メチルベンゾイル）−９Ｈ−カルバゾール−３−イル］−３−シクロペンチルプロパン−１−オン−２−イミンが挙げられる。イルガキュア（登録商標）ＯＸＥ０１、ＯＸＥ０２（以上、ＢＡＳＦ社製）、Ｎ−１９１９（ＡＤＥＫＡ社製）等の市販品を用いてもよい。 The O-acyl oxime compound is a compound having a partial structure represented by the formula (d1). Hereinafter, * 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) octane- 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-2,4) -Dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethane-1-imine, N-acetoxy-1- [9 Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -3-cyclopentylpropane-1-imine, N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl)- 9H-carbazol-3-yl] -3-cyclopentylpropan-1-one-2-imine. Commercial products such as Irgacure (registered trademark) OXE01, OXE02 (above, manufactured by BASF), N-1919 (manufactured by ADEKA) may be used.

The alkylphenone compound is a compound having a partial structure represented by the formula (d2) or a partial structure represented by the formula (d3). In these partial structures, the benzene ring may have a substituent.

Examples of the compound having a partial structure represented by the formula (d2) include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4 -Morpholinophenyl) -2-benzylbutan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butan-1-one Is mentioned. Commercial products such as Irgacure (registered trademark) 369, 907 and 379 (manufactured by BASF) may be used.
Examples of the compound having a partial structure represented by the formula (d3) 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, oligomer of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, α, α-diethoxy Examples include acetophenone and benzyldimethyl ketal.
In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by the formula (d2).

  Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxy Naphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) ) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4- Bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2) -Methylphenyl) Thenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

  Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercial products such as Irgacure 819 (manufactured by Ciba Japan) may be used.

  Examples of the biimidazole compound include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole and 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′-tetraphenylbiimidazole, 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetra (alkoxyphenyl) biimidazole, 2,2′-bis ( 2-chlorophenyl) -4,4 ′, 5,5′-tetra (dialkoxyphenyl) biimidazole, 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetra (trialkoxy) Phenyl) biimidazole (for example, see JP-B-48-38403, JP-A-62-174204, etc.), and the phenyl group at the 4,4′5,5′-position is substituted with a carboalkoxy group. Examples thereof include imidazole compounds (for example, see JP-A-7-10913).

Furthermore, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Examples include quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.
These are preferably used in combination with a polymerization initiation assistant (D1) (particularly amines) described later.

  Examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenyl methyl. Onium salts such as benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyl tosylate, Examples include benzoin tosylate.

  The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Part by mass. When the content of the polymerization initiator (D) is in the above range, the sensitivity is increased and the exposure time tends to be shortened, so that productivity is improved.

In addition to the polymerization initiator (D), a polymerization initiation assistant (D1) may further be included. The polymerization initiation assistant (D1) is a compound or a sensitizer used for accelerating the polymerization of the photopolymerizable compound that has been polymerized by the polymerization initiator.
Examples of the polymerization initiation assistant (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

  Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4- 2-ethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4′-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4′-bis (diethylamino) benzophenone, 4,4′-bis ( Ethylmethylamino) benzophenone and the like, and 4,4′-bis (diethylamino) benzophenone is preferred. Commercial products such as EAB-F (Hodogaya Chemical Co., Ltd.) may be used.

  Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-dibutoxy. Anthracene, 2-ethyl-9,10-dibutoxyanthracene, etc. are mentioned.

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

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, naphthoxyacetic acid and the like.
The polymerization initiation assistant (D1) may be used alone or in combination of two or more.

  When these polymerization initiation assistants (D1) are used, the amount used is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Preferably it is 1-20 mass parts. When the amount of the polymerization initiation assistant (D1) is within this range, a colored pattern can be formed with higher sensitivity and the productivity of the color filter tends to be improved.

<Solvent (E)>
A solvent (E) is not specifically limited, The solvent normally used in the said field | area can be used. For example, an ester solvent (a solvent containing —COO— in the molecule and not containing —O—), an ether solvent (a solvent containing —O— in the molecule and not containing —COO—), an ether ester solvent (intramolecular) Solvent containing -COO- and -O-), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent, aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide, etc. Can be selected and used.

  As ester solvents, 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, γ-butyrolactone and the like.

  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, diethyl Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and the like methyl anisole.

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

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

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

  Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.

  Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.

These solvents may be used alone or in combination of two or more.
Among the above-mentioned solvents, an organic solvent having a boiling point at 1 atm of 120 ° C. or higher and 180 ° C. or lower is preferable from the viewpoints of coating properties and drying properties.
As the solvent (E), propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether and 4-hydroxy-4-methyl- 2-Pentanone is preferable, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and ethyl 3-ethoxypropionate are more preferable.

  Content of a solvent (E) becomes like this. Preferably it is 70-95 mass% with respect to the total amount of a coloring photosensitive resin composition, More preferably, it is 75-92 mass%. In other words, the solid content of the colored photosensitive resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content of the solvent (E) is in the above range, the flatness at the time of coating is good, and when the color filter is formed, the color density does not become insufficient and the display characteristics tend to be good.

<Surfactant (F)>
Examples of the surfactant (F) include silicone surfactants, fluorine surfactants, silicone surfactants having fluorine atoms, and the like. These may have a polymerizable group in the side chain.
Examples of the silicone surfactant include a surfactant having a siloxane bond in the molecule. Specifically, Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade names: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (made by Momentive Performance Materials Japan GK) Can be mentioned.

  Examples of the fluorosurfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), MegaFac (registered trademark) F142D, F171, F172, F173, F177, F183, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals), Surflon (registered trademark) S381, S382, SC101, SC105 (Asahi Glass Co., Ltd.), E5844 (Daikin Fine Chemical Laboratory Co., Ltd.) and the like.

  Examples of the silicone-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation) and the like can be mentioned.

  The content of the surfactant (F) is preferably 0.001% by mass or more and 0.2% by mass or less, and preferably 0.002% by mass or more and 0.00% by mass or less with respect to the total amount of the colored photosensitive resin composition. It is 1 mass% or less, More preferably, it is 0.01 mass% or more and 0.05 mass% or less. This content does not include the content of the pigment dispersant. When the content of the surfactant (F) is in the above range, the flatness of the color filter can be improved.

<Other ingredients>
The colored photosensitive resin composition of the present invention includes additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, etc., if necessary. May be included.

<Method for producing colored photosensitive resin composition>
The colored photosensitive resin composition of the present invention includes, for example, a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a polymerization initiation assistant used as necessary ( D1), the solvent (E), the surfactant (F) and other components can be prepared by mixing by a known method.
When the pigment (A2) is included, the pigment (A2) is preferably mixed with the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size of the pigment is about 0.2 μm or less. Under the present circumstances, you may mix | blend a part or all of the said pigment dispersant and resin (B) as needed. In the obtained pigment dispersion, the remainder of the resin (B) and the polymerizable compound (C), the polymerization initiator (D) used as necessary, the remainder of the solvent (E), the surfactant (F ) And other components and the like are mixed so as to have a predetermined concentration, whereby the desired colored photosensitive resin composition can be prepared.
The dye (A1) may be previously dissolved in the solvent (E). The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.
The colored photosensitive resin composition after mixing is preferably filtered with a filter having a pore size of about 0.01 to 10 μm.

<Color filter manufacturing method>
Examples of a method for producing a color filter color pattern from the colored photosensitive resin composition of the present invention include a photolithographic method, an inkjet method, and a printing method. Of these, the photolithographic method is preferable. The photolithographic method is a method in which the colored photosensitive resin composition is applied to a substrate and dried to form a composition layer, and the composition layer is exposed through a photomask and developed. In the photolithography method, a colored coating film that is a cured product of the composition layer can be formed by not using a photomask and / or not developing during exposure.
The film thickness of the color filter to be produced is not particularly limited, and can be appropriately adjusted according to the purpose and application, and is preferably 0.1 to 30 μm, more preferably 0.1 to 20 μm, and still more preferably 0. .5-6 μm.

  As a substrate, quartz glass, borosilicate glass, alumina silicate glass, glass plate such as soda lime glass coated with silica on the surface, resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, on the substrate What formed aluminum, silver, a silver / copper / palladium alloy thin film, etc. is used. On these substrates, another color filter layer, a resin layer, a transistor, a circuit, and the like may be formed.

Formation of each color pixel by the photolithographic method can be performed by a known or commonly used apparatus and conditions. For example, it can be produced as follows.
First, a colored photosensitive resin composition is applied on a substrate, dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as a solvent, and a smooth composition layer is obtained.
Examples of the coating method include spin coating, slit coating, and slit and spin coating.
30-120 degreeC is preferable and the temperature in the case of performing heat drying has more preferable 50-110 degreeC. In addition, the heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes.
When performing vacuum drying, it is preferable to carry out in the temperature range of 20-25 degreeC under the pressure of 50-150 Pa.
The film thickness of the composition layer is not particularly limited, and can be appropriately adjusted depending on the material used, application, and the like.

Next, the composition layer is exposed through a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
The light source used for exposure is preferably a light source that generates light having a wavelength of 250 to 450 nm. For example, light less than 350 nm can be cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Or you may. Examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp, and a halogen lamp.
It is preferable to use an exposure apparatus such as a mask aligner and a stepper because the entire exposed surface can be irradiated with parallel light rays uniformly and the photomask and the composition layer can be accurately aligned.

By developing the exposed composition layer in contact with a developer, a colored pattern is formed on the substrate. By the development, the unexposed portion of the composition layer is dissolved and removed in the developer. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Further, the developer may contain a surfactant.
The developing method may be any of paddle method, dipping method, spray method and the like. Further, the substrate may be tilted at an arbitrary angle during development.
After development, it is preferable to wash with water.
When the unexposed part of the composition layer is removed so as to peel off, the peeled composition layer floats in the developer without dissolving in the developer, and thus may adhere to the colored pattern and become a foreign substance. However, in the colored photosensitive resin composition of the present invention, since the unexposed portion is dissolved and removed in the developer, the generation of foreign matter on the colored pattern is suppressed.

  Furthermore, it is preferable to post-bake the obtained colored pattern. The post-bake temperature is preferably 150 to 250 ° C, more preferably 160 to 235 ° C. The post-bake time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

The colored pattern and the colored coating film thus obtained are useful as a color filter.
According to the present invention, it is possible to provide a colored photosensitive resin composition capable of producing a color filter in which generation of foreign matter is particularly suppressed. Therefore, the color filter can be suitably used for a display device (for example, a liquid crystal display device, an organic EL device, etc.), electronic paper, a solid-state image sensor, and the like.

  Next, the present invention will be described more specifically with reference to examples. In the examples, “%” and “part” representing the content or amount used are based on mass unless otherwise specified.

[Synthesis Example 1]
A mixture of a compound represented by the formula (A1-1a) and a compound represented by the formula (A1-1b) (trade name Chugai Aminol Fast Pink R; manufactured by Chugai Kasei Co., Ltd.) 15 in a flask equipped with a condenser and a stirrer. Part, 150 parts of chloroform and 8.9 parts of N, N-dimethylformamide were added dropwise and 10.9 parts of thionyl chloride was added dropwise while maintaining at 20 ° C. or lower with stirring. After completion of the dropwise addition, the temperature was raised to 50 ° C., the reaction was continued for 5 hours at the same temperature, and then cooled to 20 ° C. While maintaining the reaction solution after cooling at 20 ° C. or lower with stirring, a mixed solution of 12.5 parts of 2-ethylhexylamine and 22.1 parts of triethylamine was added dropwise. Then, it was made to react by stirring at the same temperature for 5 hours. Next, after the solvent of the obtained reaction mixture was distilled off with a rotary evaporator, a small amount of methanol was added and stirred vigorously. This mixture was added to a mixture of 375 parts of ion exchange water with stirring to precipitate crystals. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, dried under reduced pressure at 60 ° C., and represented by the dye (A1-1) (formula (A1-1-1) to formula (A1-1-8). 11.3 parts of a mixture of compounds to be obtained.

次いで、式（Ａ１−２ｂ）で表される化合物２０．１部、ヨードエタン（東京化成（株）製）２８．７部および炭酸カリウム２５．４部、Ｎ−メチルピロリドン（関東化学（株）製）１３０．７部を混合し、遮光条件下８０℃で４時間攪拌した。得られた反応液を室温まで冷却後に濃縮し、水４６０部中に添加し１０〜１５℃で１時間攪拌したところ、結晶が析出した。生じた結晶を吸引濾過の残渣として取得後、２０％メタノール水５００部、イオン交換水１０００部で洗浄後、１晩６０℃減圧乾燥し、式（Ａ１−２）で表される化合物２０．６部を得た。収率は９３％であった。

式（Ａ１−２）で表される化合物の同定
（質量分析）イオン化モード＝ＥＳＩ＋： ｍ／ｚ＝[Ｍ＋Ｈ]^＋６０３．３
Ｅｘａｃｔ Ｍａｓｓ： ６０２．２ [Synthesis Example 2]
40.5 parts of the compound represented by the formula (A1-2a) and 64.4 parts of 2-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) are mixed, and further N-methylpyridone (manufactured by Kanto Chemical Co., Inc.). 263 parts were added and stirred at 120 ° C. for 8 hours. The obtained reaction solution was cooled to room temperature, then added to a mixed solution of 1200 parts of water and 75 parts of 35% hydrochloric acid and stirred at room temperature for 1 hour, whereby crystals were precipitated. The precipitated crystals were obtained as a residue of suction filtration, washed with 50 parts of tetrahydrofuran and 200 parts of water, and then dried under reduced pressure at 60 ° C. overnight to obtain 49 parts of a compound represented by the formula (A1-2b). The yield was 89%.

Next, 20.1 parts of the compound represented by the formula (A1-2b), 28.7 parts of iodoethane (manufactured by Tokyo Chemical Industry Co., Ltd.) and 25.4 parts of potassium carbonate, N-methylpyrrolidone (manufactured by Kanto Chemical Co., Inc.) ) 130.7 parts were mixed and stirred for 4 hours at 80 ° C. under light shielding conditions. The obtained reaction solution was cooled to room temperature, concentrated, added to 460 parts of water, and stirred at 10 to 15 ° C. for 1 hour to precipitate crystals. The resulting crystals are obtained as a residue of suction filtration, washed with 500 parts of 20% methanol water and 1000 parts of ion-exchanged water, dried at 60 ° C. overnight under reduced pressure, and compound 20.6 represented by formula (A1-2). Got a part. The yield was 93%.

Identification of compound represented by formula (A1-2) (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ 603.3
Exact Mass: 602.2

次いで、式（Ａ１−３ｂ）で表される化合物２８．８部と、１−ブロモプロパン２１．６部および炭酸カリウム２４．２部をＮ−メチルピリドン１４４部中に加え、９０℃で４時間攪拌した。得られた反応液を室温まで冷却後に濃縮し、水５６０部中に添加し１０〜１５℃で１時間攪拌したところ、結晶が析出した。生じた結晶を吸引濾過の残渣として取得後乾燥し、イオン交換水１０００部で洗浄後、１晩６０℃減圧乾燥し、式（Ａ１−３）で表される化合物３０．０部を得た。収率は９１％であった。

式（Ａ１−３）で表される化合物の同定
（質量分析）イオン化モード＝ＥＳＩ＋： ｍ／ｚ＝[Ｍ＋Ｈ]^＋６５９．３
Ｅｘａｃｔ Ｍａｓｓ： ６５８．３ [Synthesis Example 3]
40.5 parts of the compound represented by the formula (A1-3a) and 60.5 parts of 2,6-xylidine (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed under light-shielding conditions, and 150 parts in 200 parts of N-methylpyridone. Stir at 8 ° C. for 8 hours. The obtained reaction solution was cooled to room temperature, then added to a mixed solution of 1200 parts of water and 75 parts of 35% hydrochloric acid and stirred at room temperature for 1 hour, whereby crystals were deposited. The precipitated crystals were obtained as a residue of suction filtration, washed with 100 parts of methanol, and dried overnight at 60 ° C. under reduced pressure to obtain 49 parts of a compound represented by the formula (A1-3b). The yield was 85%.

Subsequently, 28.8 parts of the compound represented by the formula (A1-3b), 21.6 parts of 1-bromopropane and 24.2 parts of potassium carbonate are added to 144 parts of N-methylpyridone, and the mixture is stirred at 90 ° C. for 4 hours. Stir. The obtained reaction solution was cooled to room temperature, concentrated, added to 560 parts of water, and stirred at 10 to 15 ° C. for 1 hour to precipitate crystals. The resulting crystals were obtained as a residue of suction filtration and then dried, washed with 1000 parts of ion-exchanged water, and then dried under reduced pressure at 60 ° C. overnight to obtain 30.0 parts of a compound represented by the formula (A1-3). The yield was 91%.

Identification of compound represented by formula (A1-3) (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ 659.3
Exact Mass: 658.3

一方、重合開始剤２，２’−アゾビス（２，４−ジメチルバレロニトリル）３０部をプロピレングリコールモノメチルエーテルアセテート２２５部に溶解した溶液を、別の滴下ロートを用いて４時間かけてフラスコ内に滴下した。重合開始剤の溶液の滴下が終了した後、４時間、７０℃に保持し、その後室温まで冷却して、重量平均分子量Ｍｗは、１．０４×１０^４、固形分３６．９質量％、固形分酸価９４ｍｇ−ＫＯＨ／ｇの共重合体（Ｂ１−１）溶液を得た。共重合体（Ｂ１−１）は、下記の構造単位を有する。

[Synthesis Example 4]
Nitrogen was allowed to flow at 0.02 L / min in a flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel to form a nitrogen atmosphere. 257 parts of propylene glycol monomethyl ether acetate was added and heated to 70 ° C. with stirring. did. Subsequently, 53 parts of acrylic acid, 166 parts of benzyl methacrylate, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate (compound represented by formula (I-1) and formula (II- 1) The compound represented by 1) is mixed at a molar ratio of 50:50.) A solution is prepared by dissolving 159 parts in 140 parts of propylene glycol monomethyl ether acetate, and the solution is prepared using a dropping funnel. Over time, it was dripped in the flask kept at 70 degreeC.

On the other hand, a solution obtained by dissolving 30 parts of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 225 parts of propylene glycol monomethyl ether acetate was placed in a flask using another dropping funnel over 4 hours. It was dripped. After the addition of the solution of the polymerization initiator is completed, 4 hours, kept at 70 ° C., then cooled to room temperature, and the weight average molecular weight Mw, 1.04 × 10 ^4, solid content 36.9 wt%, solid A copolymer (B1-1) solution having a partial acid value of 94 mg-KOH / g was obtained. The copolymer (B1-1) has the following structural units.

[Synthesis Example 5]
Nitrogen was allowed to flow at 0.02 L / min in a flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel to form a nitrogen atmosphere. 257 parts of propylene glycol monomethyl ether acetate was added and heated to 70 ° C. with stirring. did. Next, 68 parts of methacrylic acid, 159 parts of benzyl methacrylate, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate (compound represented by formula (I-1) and formula (II- 1) The compound represented by 1) is mixed at a molar ratio of 50:50.) A solution is prepared by dissolving 151 parts in 140 parts of propylene glycol monomethyl ether acetate. Over time, it was dripped in the flask kept at 70 degreeC. On the other hand, a solution obtained by dissolving 30 parts of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 225 parts of propylene glycol monomethyl ether acetate was placed in a flask using another dropping funnel over 4 hours. It was dripped. After completion of dropping of the polymerization initiator solution, the solution was kept at 70 ° C. for 4 hours and then cooled to room temperature. The weight average molecular weight Mw was 9.5 × 10 ³ , the solid content was 36.7% by mass, A copolymer (B1-2) solution having a partial acid value of 95 mg-KOH / g was obtained. The copolymer (B1-2) has the following structural units.

[Synthesis Example 6]
Nitrogen was allowed to flow at 0.02 L / min in a flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel to form a nitrogen atmosphere, and 257 parts by mass of propylene glycol monomethyl ether acetate was added and stirred to 70 ° C. Heated. Next, 57 parts of acrylic acid, 178 parts of dicyclopentanyl acrylate, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate (compound represented by formula (I-1) and formula The compound represented by (II-1) is mixed at a molar ratio of 50:50.) A solution is prepared by dissolving 144 parts in 140 parts by mass of propylene glycol monomethyl ether acetate, and the solution is added to a dropping funnel. Was added dropwise to the flask kept at 70 ° C. over 4 hours. On the other hand, a solution obtained by dissolving 30 parts of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 225 parts by mass of propylene glycol monomethyl ether acetate was added to the flask over another 4 hours using another dropping funnel. It was dripped in. After completion of dropping of the polymerization initiator solution, the solution was kept at 70 ° C. for 4 hours and then cooled to room temperature. The weight average molecular weight Mw was 1.14 × 10 ⁴ , solid content 36.5%, solid content. A copolymer (B1-3) solution having an acid value of 111 mg-KOH / g was obtained. The copolymer (B1-3) has the following structural units.

[Synthesis Example 7]
Nitrogen was allowed to flow at 0.02 L / min in a flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel to form a nitrogen atmosphere. 257 parts of propylene glycol monomethyl ether acetate was added and heated to 70 ° C. with stirring. did. Subsequently, 57 parts of acrylic acid, 181 parts of isobornyl acrylate, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate (compound represented by formula (I-1) and formula ( The compound represented by II-1) is mixed at a molar ratio of 50:50.) A solution is prepared by dissolving 144 parts in 140 parts of propylene glycol monomethyl ether acetate, and the solution is added using a dropping funnel. Then, the solution was dropped into a flask kept at 70 ° C. over 4 hours. On the other hand, a solution obtained by dissolving 30 parts of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 225 parts by mass of propylene glycol monomethyl ether acetate was added to the flask over another 4 hours using another dropping funnel. It was dripped in. After the addition of the solution of the polymerization initiator is completed, 4 hours, kept at 70 ° C., then cooled to room temperature, and the weight average molecular weight Mw, 9.6 × 10 ^3, solid content 37.2 wt%, solid A copolymer (B1-4) solution having a partial acid value of 107 mg-KOH / g was obtained. The copolymer (B1-4) has the following structural units.

[Synthesis Example 8]
In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, nitrogen was allowed to flow at 0.02 L / min to form a nitrogen atmosphere, 220 parts of ethyl lactate was added, and the mixture was heated to 70 ° C. with stirring. Next, 84 parts of methacrylic acid and 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate (a compound represented by formula (I-1) and a formula (II-1) The solution is prepared by dissolving 336 parts of the compound to be mixed at a molar ratio of 50:50 in 140 parts of ethyl lactate, and the solution is kept at 70 ° C. for 4 hours using a dropping funnel. The solution was dropped into the flask. On the other hand, a solution obtained by dissolving 30 parts of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 95 parts of ethyl lactate was dropped into the flask using another dropping funnel over 4 hours. After dropping of the solution of the polymerization initiator is completed, the temperature is kept at 70 ° C. for 4 hours, and then cooled to room temperature. The weight average molecular weight Mw is 8.0 × 10 ³ , the molecular weight distribution is 2.5, and the solid content is A resin (B2-1) solution having 48% and a solution acid value of 50 mg-KOH / g (acid value in terms of solid content is 104 mgKOH / g) was obtained.

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin obtained in the synthesis example were measured using the GPC method under the following conditions.
Apparatus; K2479 (manufactured by Shimadzu Corporation)
Column; SHIMADZU Shim-pack GPC-80M
Column temperature: 40 ° C
Solvent; THF (tetrahydrofuran)
Flow rate: 1.0 mL / min
Detector; RI
Standard material for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
The polystyrene-converted weight average molecular weight and number average molecular weight ratio (Mw / Mn) obtained above was defined as molecular weight distribution.

Examples 1 to 4 and Comparative Example 1
[Preparation of pigment dispersion 1]
Colorant (A); C.I. I. Pigment Blue 15: 6 (pigment) 10.1 parts Acrylic pigment dispersant 6.5 parts Solvent (E); Propylene glycol monomethyl ether acetate 59 parts Solvent (E); Ethyl lactate 25 parts are mixed and bead mill is used. The pigment dispersion 1 was obtained by fully dispersing the pigment.
[Preparation of pigment dispersion 2]
Colorant (A); C.I. I. Pigment Blue 15: 6 (pigment) 20 parts Acrylic pigment dispersant 5 parts Solvent (E); 142 parts of propylene glycol monomethyl ether acetate are mixed, and the pigment is sufficiently dispersed using a bead mill, whereby pigment dispersion 2 Got.
[Preparation of colored photosensitive resin composition]
The components shown in Table 1 were mixed to obtain a colored photosensitive resin composition.

In Table 1, each component represents the following.
Colorant (A); (A1-1); Dye (A1-1)
Colorant (A); (A2-1); Pigment dispersion 1
Colorant (A); (A2-2); Pigment dispersion 2
Resin (B); (B1-1); Copolymer (B1-1) Solution Resin (B); (B1-2); Copolymer (B1-2) Solution Resin (B); (B1-3) Copolymer (B1-3) solution resin (B); (B1-4); copolymer (B1-4) solution resin (B); (B2-1); resin (B2-1) solution polymerizability Compound (C); (C-1); dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)
Polymerization initiator (D); (D-1); N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF; -Acyl oxime compound)
Polymerization initiator (D); (D-2); 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one (Irgacure (registered trademark) 907; manufactured by BASF Corp .; alkylphenone compound )
Polymerization initiation aid (D1); (D1-1); 2,4-diethylthioxanthone (KAYACURE® DETX; manufactured by Nippon Kayaku Co., Ltd .; thioxanthone compound)
Solvent (E); (E-1); Propylene glycol monomethyl ether acetate Solvent (E); (E-2); Ethyl lactate Solvent (E); (E-3); Propylene glycol monomethyl ether Surfactant (F) (F-1); polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[Foreign matter evaluation]
After a colored photosensitive resin composition is applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by a spin coating method, the pressure is reduced by 2 at 50 Pa using a vacuum dryer (VCD; manufactured by Microtech Co., Ltd.). It was dried under reduced pressure for 2 seconds. An aqueous developer containing 0.12% of a nonionic surfactant and 2% of sodium carbonate was immersed in the dried film for 20 seconds at 23 ° C. and washed with water. The substrate after washing was observed using a microscope (magnification 250 times; VF-7510; manufactured by Keyence Corporation). If no foreign matter was observed on the substrate after washing, ○, on the substrate after washing. Table 3 shows the case where foreign matter was recognized as x. If no foreign matter is found on the substrate by this test, it can be said that no foreign matter is found on the substrate and the colored pattern even when the colored pattern is formed on the substrate by the photolithographic method.

[Preparation of colored pattern]
A colored photosensitive resin composition was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100 ° C. for 3 minutes to form a composition layer. After standing to cool, the distance between the substrate on which the composition layer is formed and the quartz glass photomask having a pattern is set to 100 μm, and an exposure machine (TME-150RSK; manufactured by Topcon Corporation) is used in an air atmosphere at 150 mJ. Light was irradiated with an exposure amount of / cm ² (based on 365 nm). As a photomask, a mask on which a 100 μm line and space pattern was formed was used. The composition layer after light irradiation is immersed and developed in an aqueous developer containing 0.12% of a nonionic surfactant and 2% of sodium carbonate at 24 ° C. for 60 seconds, washed with water, and then in an oven at 230 ° C. for 30 minutes. Post-baking was performed to obtain a colored pattern.

[Film thickness measurement]
About the obtained coloring pattern, the film thickness was measured using the film thickness measuring apparatus (DEKTAK3; Nippon Vacuum Technology Co., Ltd. product). The results are shown in Table 2.

[Chromaticity evaluation]
About the coloring pattern on the obtained glass substrate, spectrum was measured using a colorimeter (OSP-SP-200; Olympus Co., Ltd.), and CIE XYZ color system using a color matching function of a C light source. Xy chromaticity coordinates (x, y) and tristimulus value Y were measured. The larger the value of Y, the higher the brightness. The results are shown in Table 2.

Examples 5 and 6
[Preparation of colored photosensitive resin composition]
The components listed in Table 3 were mixed to obtain a colored photosensitive resin composition. The evaluation was performed in the same manner as in Example 1. The results are shown in Table 4.

Colorant (A); (A1-2); Dye (A1-2)
Colorant (A); (A1-3); Dye (A1-3)

  In the colored photosensitive resin compositions of the examples, it was confirmed that peeling due to development was suppressed during the formation of the colored pattern, and no foreign matter was observed on the substrate after the colored pattern was formed. From this, a display apparatus can be manufactured with a high yield by using the colored pattern obtained from the colored photosensitive resin composition of the present invention as a color filter.

  ADVANTAGE OF THE INVENTION According to this invention, it becomes possible to provide the colored photosensitive resin composition which can reduce the foreign material on a coloring pattern, and the color filter containing this coloring pattern is a display apparatus (for example, liquid crystal display device, organic EL devices, etc.), electronic paper, solid-state imaging devices and the like.

Claims (5)

Including a colorant, a resin, a polymerizable compound and a polymerization initiator,
The colorant contains a dye,
A monomer having a structural unit derived from at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride, a cyclic ether structure having 2 to 4 carbon atoms, and an ethylenically unsaturated bond A structural unit derived from the formula (x)

[In formula (x), R ^a1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
R ^a2 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group and the aromatic hydrocarbon group May be substituted with an alkyl group having 1 to 10 carbon atoms.
X ^a1 represents a single _{^{bond, -X a2 -, * - (}} X a2 -O) k -, * - X a2 -S- or ^* -X represents an a2 -NH-. * Represents a bond with O.
X ^a2 represents an alkanediyl group having 1 to 6 carbon atoms.
k represents an integer of 1 to 4. ]
A resin containing a copolymer containing a structural unit derived from a monomer represented by:
The monomer having a C2-C4 cyclic ether structure and an ethylenically unsaturated bond is a monomer having a structure in which an unsaturated alicyclic hydrocarbon is epoxidized,
Colored photosensitive resin composition wherein the content of structural units derived from the monomer represented by formula (x) is 1 mol% or more and 80 mol% or less with respect to the total amount of structural units constituting the copolymer object. The coloring according to claim 1, wherein the monomer having an epoxidized structure of unsaturated alicyclic hydrocarbon is at least one monomer selected from the group consisting of formula (I) and formula (II). Photosensitive resin composition.

[In Formula (I) and Formula (II), R ^b1 and R ^b2 represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with a hydroxy group. May be.
X ^b1 and ^{X b2} represents a single ^{bond, -R b3 -, * - R} b3 -O -, * - R b3 -S- or ^* -R b3 represents a -NH-.
R ^b3 represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ] The colored photosensitive resin composition according to claim 1 or 2 , wherein the colorant further contains a pigment. A color filter formed by colored photosensitive resin composition according to any one of claims 1-3. A display device comprising the color filter according to claim 4 .