A color-curable resin composition, a color filter, a display device containing the same, and a method for manufacturing the color filter.

Abstract

The object of this invention is to provide a color-curable resin composition that can form a color filter with a good pattern shape even when heated at low temperatures. [Solution] A colored curable resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator, wherein the resin is a resin (BQ) having a group represented by formula (Q) and having a weight-average molecular weight (Mw) of 17,000 or more on a polystyrene basis. TIFF2026148471000016.tif1971 [In formula (Q), R Q1 represents an isocyanate protecting group. * represents a bond.

Description

[Technical Field]

[0001] The present invention relates to a color-curable resin composition, a color filter, a display device containing the same, and a method for manufacturing the color filter. [Background technology]

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state image sensors such as CCDs and CMOS sensors, are manufactured from a color-curable resin composition as a patterned cured product, for example, by photolithography. Such color-curable resin compositions typically contain alkali-soluble resins. For example, an example is known in which an alkali-soluble resin having a blocked isocyanate group-containing monomer unit is used as a low-temperature curable color resist for RGB-OLED (Organic Light-Emitting Diode) (Patent Document 1). [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2024-078787 [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] However, in order to respond to changes in performance requirements such as darker colors and higher standards for required shapes, there is a need for a color-curable resin composition that can produce a better shape than conventional compositions. Therefore, the object of the present invention is to provide a color-curable resin composition that can form a color filter with a good pattern shape even when heated at low temperatures. [Means for solving the problem]

[0005] The inventors have found that the above objective can be achieved by the colored curable resin composition of the present invention, as described below. That is, the present invention includes the following embodiments. [1] comprising a colorant, resin, polymerizable compound and polymerization initiator, A colorable curable resin composition comprising a resin (BQ) having a group represented by formula (Q) and having a weight-average molecular weight (Mw) of 17,000 or more on a polystyrene basis. [ka] [In formula (Q), R Q1 represents an isocyanate protecting group. * represents a bond. [2] The colored curable resin composition according to [1], wherein the resin (BQ) is an alkali-soluble resin. [3] The resin (BQ) further comprises structural units derived from monomers represented by formula (1) as described in [1] or [2]. [ka] [In formula (1), R 1 R represents a hydrogen atom or a methyl group. 2 [This represents a linear or branched alkyl group having 6 to 25 carbon atoms.] [4] The colored curable resin composition according to any one of [1] to [3], wherein the resin (BQ) further comprises structural units derived from monomers having hydroxyl groups and ethylenically unsaturated bonds. [5] A colored curable resin composition according to any one of [1] to [4], further comprising a silane coupling agent. [6] The colored curable resin composition according to [5], wherein the silane coupling agent is a nitrogen-containing silane coupling agent. [7] A color filter which is a cured film of a colored curable resin composition described in any one of [1] to [6]. A display device including the color filter described in [8] [7]. A step of applying the colored curable resin composition according to any one of [9] [1] to [6], and pre-baking the composition to form a composition layer, A step of exposing the obtained composition layer through a mask, A step of developing the exposed composition layer to form a pattern, and A step of post-baking the obtained pattern, A method for producing a color filter, comprising The production method, wherein the post-baking temperature is 50 to 120° C.

Effects of the Invention

[0006] According to the present invention, there is provided a colored curable resin composition capable of forming a color filter having a favorable pattern shape even when heated at a low temperature.

Brief Description of Drawings

[0007] [Figure 1] FIG. 1 is a schematic diagram illustrating a method for measuring a taper angle.

Mode for Carrying Out the Invention

[0008] Hereinafter, embodiments of the present invention will be described in detail. The scope of the present invention is not limited to the embodiments described herein, and various modifications can be made without departing from the spirit and scope of the present invention. In addition, when a plurality of upper limit values and lower limit values for specific parameters are described, any combination of an upper limit value and a lower limit value among these upper limit values and lower limit values can be selected to form a suitable numerical range.

[0009] <Colored Curable Resin Composition> The colored curable resin composition of the present invention comprises a colorant, a resin, a polymerizable compound and a polymerization initiator. In the present specification, unless otherwise specified, the compounds exemplified as each component may be used alone or in combination of two or more.

[0010] (Colorant) The color-curable resin composition of the present invention contains at least one colorant. The color-curable resin composition of the present invention containing at least one colorant can be suitably used as a color-curable resin composition for creating a resist layer in a color filter. Furthermore, the color-curable resin composition of the present invention having the above composition can be darkened when used as a color resist composition, making it easier to achieve the desired color. The colorant may be either a dye or a pigment, but it is preferable to include a pigment. As the pigment, known pigments can be used, for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0011] Specifically, yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231, 235, 236; orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 272, 273, 291, 297, and other red pigments; CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, and other blue pigments; CI Pigment Violet 1, 19, 23, 29, 32, 36, 37, 38, and other violet color pigments; CI Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, 67 green pigments; CI Pigment Brown 23, 25, and other brown pigments; Examples include black pigments such as CI Pigment Black 1, 7, 31, and 32.

[0012] The pigment may be subjected to rosin treatment, surface treatment using pigment derivatives into which acidic or basic groups have been introduced, grafting treatment of the pigment surface with polymer compounds, atomization treatment by sulfuric acid atomization method, washing treatment with organic solvents or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc., as needed. It is preferable that the pigment has a uniform particle size. Furthermore, by dispersing the pigment with a pigment dispersant, a pigment dispersion can be obtained in which the pigment is uniformly dispersed in the solution.

[0013] Examples of pigment dispersants include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. Examples of pigment dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers (manufactured by Lubrizol), EFKA (manufactured by CIBA), Azisper (manufactured by Ajinomoto Fine Techno Co., Ltd.), and Disperbyk (manufactured by Bic Chemie).

[0014] When a 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, relative to the total amount of pigment. When the amount of pigment dispersant used is within the above range, a pigment dispersion liquid with a uniform dispersion state tends to be obtained.

[0015] The colored resin composition is preferably used as a colored resin composition for forming a red color filter, a green color filter, or a blue color filter. For a red color filter, it is preferable to have a colored resin composition having maximum absorption in the wavelength region of 485 to 530 nm; for a green color filter, it is preferable to have a colored resin composition having maximum absorption in the wavelength region of 610 to 800 nm; and for a blue color filter, it is preferable to have a colored resin composition having maximum absorption in the wavelength region of 570 to 600 nm.

[0016] When producing a green color filter, the colorant (A) preferably contains a green pigment, more preferably a green phthalocyanine-based pigment, and even more preferably at least one green pigment selected from CI Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, 67. Furthermore, when producing a green color filter, the colorant (A) preferably contains, in addition to the green pigment, at least one selected from the group consisting of phthalocyanine dyes, azo dyes, yellow pigments, and blue pigments, more preferably a yellow pigment and / or a blue pigment, and even more preferably both a yellow pigment and a blue pigment. As a yellow pigment used in combination with the green pigment, at least one selected from CI Pigment Yellow 139, 150, 185, 235, 236 is preferred. As a blue pigment used in combination with the green pigment, at least one selected from CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16 is preferred. Furthermore, from the viewpoint of improving color intensity and contrast, black pigments such as carbon black may be further included. The pigments preferably include yellow pigments or green pigments, and more preferably include one or more selected from the group consisting of CI Pigment Yellow 139, CI Pigment Yellow 150, and CI Pigment Green 36. When producing a green color filter, the content of green pigment in the colorant (A) is, for example, 10 to 100% by mass, preferably 20 to 90% by mass, more preferably 25 to 80% by mass, and even more preferably 30 to 60% by mass.

[0017] When producing a red color filter, the coloring agent (A) preferably contains a red pigment, and more preferably contains at least one red pigment selected from the group consisting of CI Pigment Red 242, 254, 264, 269, 272, and 291. Furthermore, when producing a red color filter, the coloring agent (A) preferably contains, in addition to the red pigment, at least one selected from the group consisting of xanthene dyes, azo dyes, yellow pigments (CI Pigment Yellow 139, 150, 235, 236, etc.), and orange pigments (CI Pigment Orange 13, etc.). When producing a red color filter, the content of the red pigment in the coloring agent (A) is, for example, 20 to 100% by mass, preferably 50 to 95% by mass, and more preferably 60 to 90% by mass.

[0018] When producing a blue color filter, the colorant (A) preferably contains a blue pigment, more preferably a blue phthalocyanine-based pigment, and even more preferably at least one blue pigment selected from the group consisting of CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, and 15:6. Furthermore, when producing a blue color filter, the colorant (A) preferably contains, in addition to the blue pigment, at least one selected from the group consisting of triarylmethane dyes, xanthene dyes, and purple pigments (CI Pigment Violet 19, 23, 37, etc.). When producing a blue color filter, the content of the blue pigment in the colorant (A) is, for example, 20 to 100% by mass, preferably 30 to 95% by mass, and more preferably 50 to 90% by mass.

[0019] The pigment content is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 90% by mass or more, particularly preferably 95% by mass or more, and may also be 100% by mass, based on 100% by mass of the coloring agent.

[0020] The coloring agent may contain a dye. The dye is not particularly limited and any known dye can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as having hue other than pigments in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in the Dyeing Notebook (Irozome-sha). In addition, based on chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Of these, organic solvent-soluble dyes are preferred.

[0021] Specifically, CI Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 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; CI 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, 1 82, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 388, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119 ,120,123,126,127,129,130,131,138,140,142,143,147,150,151,154,158,161,166,167,168,170,171,175,182,183,184,187,192,199,203,204,205,210,213,229,234,236,242,243,256,259,267,269,278,280,285,290,296,315,32 4:1, 335, 340; CI Acid Green dyes such as 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, etc. CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 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; CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other CI Direct dyes, CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse Blue 1, 14, 56, 60 and other CI disperse dyes, CI Basic Red 1, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic Red 9; CI Basic Green 1 and other CI Basic dyes, CI Reactive Yellow 2,76,116; CI Reactive Orange 16; CI Reactive Dyes such as CI Reactive Red 36, CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Modant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI 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; CI Modant Green dyes such as 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. Examples include CI bat dyes such as CI bat green 1.

[0022] The dye content is preferably 50% by mass or less, more preferably 30% by mass or less, even more preferably 10% by mass or less, particularly preferably 5% by mass or less, and may even be 0% by mass.

[0023] The colorant content is preferably 5 to 60% by mass, more preferably 8 to 55% by mass, and even more preferably 10 to 50% by mass, relative to the total amount of solids in the colored curable resin composition. When the colorant content is within the above range, the color density when used as a color filter is sufficient, and the required amount of curable resin can be included in the composition, so that a pattern with sufficient mechanical strength can be formed.

[0024] In colored curable resin compositions where particularly deep coloring is required, the colorant content is preferably 15 to 60% by mass, more preferably 20 to 55% by mass, and even more preferably 23 to 50% by mass, relative to the total amount of solids in the colored curable resin composition. When the colorant content is within the above range, a particularly high color density can be achieved when used as a color filter, and the required amount of curable resin can be included in the composition, so that a pattern with sufficient mechanical strength can be formed.

[0025] (resin) The resin includes a resin (BQ) having a group represented by formula (Q) (hereinafter sometimes referred to as a "blocked isocyanate group") and having a weight-average molecular weight (Mw) of 17,000 or more on a polystyrene basis. Because the resin (BQ) has a blocked isocyanate group, the color-curable resin composition of the present invention has excellent storage stability at room temperature and is advantageous for low-temperature curing. In addition, because the resin (BQ) has a specific Mw, the pattern shape of the color filter formed from the color-curable resin composition is good.

[0026] [ka]

[0027] [In formula (Q), R Q1 represents an isocyanate protecting group. * represents a bond.

[0028] The resin (BQ) is preferably an alkali-soluble resin. Alkali solubility refers to the property of dissolving in a developing solution, which is an aqueous solution of an alkali compound. Specifically, examples include resins having carboxyl groups and / or phenolic hydroxyl groups, and resins having carboxyl groups are preferred.

[0029] The resin (BQ) has a group represented by formula (Q), preferably an isocyanate compound (α) containing the group represented by formula (Q) and an ethylenically unsaturated bond (hereinafter referred to as "compound (α)"). It has a structural unit (I) derived from (in some cases). Specifically, isocyanate compound (α) is an isocyanate compound (β) (hereinafter referred to as "compound (β)") in which the isocyanate group is not blocked, and the blocking agent R Q1 This is a compound blocked by -H. The isocyanate protecting group R is present in the blocked isocyanate group. Q1 The active isocyanate group is regenerated by heating, which deblocks the compound. The deblocking temperature is preferably 50 to 120°C, more preferably 60 to 100°C. Examples of ethylenically unsaturated groups contained in compound (α) include vinyl groups and (meth)acryloyloxy groups.

[0030] Blocking agent R Q1-H can be, for example, lactam compounds such as ε-caprolactam, δ-valerolactam, γ-butyrolactam, β-propiolactam; methanol, ethanol, propanol, 1-methoxy-2-propanol, butanol, ethylene glycol, methyl cellosolve, butyl cellosolve, methyl carbitol, benzyl alcohol, phenyl cellosolve, furfuryl alcohol, cyclohexanol, malate esters, 2-methylmalate ester, 3-methylmalate ester, 2,3-dimethylmalate ester, Alcohols such as tartaric acid esters and citrate esters; phenols such as 2,6-dimethylphenol, cresol, 3,5-xylenol, ethylphenol, o-isopropylphenol, p-tert-butylphenol, p-tert-octylphenol, nonylphenol, dinonylphenol, styrene phenol, methyl 2-hydroxybenzoate, methyl 4-hydroxybenzoate, thymol, p-naphthol, p-nitrophenol, p-chlorophenol, and other phenolic compounds; Active methylene compounds such as dimethyl malonate, diethyl malonate, methyl acetoacetate, ethyl acetoacetate, and acetylacetone; mercaptan compounds such as butyl mercaptan, thiophenol, and tert-dodecyl mercaptan; amine compounds such as diisopropylamine, diphenylamine, phenylnaphthylamine, aniline, and carbazole; acid amide compounds such as acetanilide, acetanisidide, acetamide, and benzamide; acid imide compounds such as succinimide and maleimide; imidazole, 2-methylimidazole, and 2-ethylimidazole. Examples include imidazoles such as dazole; pyrazoles such as pyrazole and 3,5-dimethylpyrazole; ureas such as urea, thiourea, and ethyleneurea; carbamidates such as phenyl N-phenylcarbamate and 2-oxazolidone; imines such as ethyleneimine and polyethyleneimine; oximes such as formaldehyde oxime, acetaldehyde oxime, acetoxime, methyl ethyl ketoxime, methyl isobutyl ketoxime, and cyclohexanone oxime; and bisulfites such as sodium bisulfite and potassium bisulfite.From the viewpoints of ease of availability, cost, and neutrality after elimination, alcohol-based, activated methylene-based, pyrazole-based, and oxime-based blocking agents are preferred, with malonic acid diesters, malic acid esters, pyrazole-based, and oxime-based agents being particularly preferred, and dimethyl malonate, diethyl malonate, diethyl malate, 3,5-dimethylpyrazole, and methyl ethyl ketoxime being particularly preferred. These blocking agents may be used alone or in combination of two or more.

[0031] Examples of compound (β) include, specifically, 2-isocyanatoethyl (meth)acrylate, 2-isocyanatopropyl (meth)acrylate, 3-isocyanatopropyl (meth)acrylate, 2-isocyanato-1-methylethyl (meth)acrylate, 2-isocyanato-1,1-dimethylethyl (meth)acrylate, 4-isocyanatocyclohexyl (meth)acrylate, and methacryloyl isocyanates; and reaction products obtained by reacting 2-hydroxyalkyl (meth)acrylate with a diisocyanate compound in equimolar amounts (2-hydroxyalkyl (meth)acrylate:diisocyanate compound = 1 mole:1 mole).

[0032] Compound (α) is specifically 2-[[[[2-[1-oxo-2-propenyl]oxy]ethyl]amino]carbonyl]-1,3-diethyl malonate, 2-[[[[2-[2-methyl-1-oxo-2-propenyl]oxy]ethyl]amino]carbonyl]-1,3-diethyl malonate, 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl acrylate, 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl methacrylate, 2-[0 Preferably, the acrylates are -(1'-methylpropyrideneamino)carboxyamino]ethyl acrylate, 2-[0-(1'-methylpropyrideneamino)carboxyamino]ethyl methacrylate, 2-[(diethyl malate)carbonylamino]ethyl acrylate, 2-[(diethyl malate)carbonylamino]methyl acrylate, 2-[(diethyl malate)carbonylamino]propyl acrylate, and 2-[(diethyl malate)carbonylamino]butyl acrylate.

[0033] Compound (α) is commercially available, for example, AOI-DEM: Karenz® AOI-DEM (reaction product of 2-isocyanatoethyl acrylate and diethyl malonate, 2-[[[[2-[1-oxo-2-propenyl]oxy]ethyl]amino]carbonyl]-1,3-diethyl malonate, manufactured by Resonaq Corporation), MOI-DEM: Karenz (registered trademark) MOI-DEM (reaction product of 2-isocyanatoethyl methacrylate and diethyl malonate, 2-[[[[2-[2-methyl-1-oxo-2-propenyl]oxy]ethyl]amino]carbonyl]-1,3-diethyl malonate, manufactured by Resonaq Corporation), AOI-BP: Karenz® AOI-BP (reaction product of 2-isocyanatoethyl acrylate and 3,5-dimethylpyrazole, 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl acrylate, manufactured by Resonaq Corporation), MOI-BP: Karenz (registered trademark) MOI-BP (reaction product of 2-isocyanatoethyl methacrylate and 3,5-dimethylpyrazole, 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl methacrylate, manufactured by Resonaq Corporation) AOI-BM: Karenz (registered trademark) AOI-BM (reaction product of 2-isocyanatoethyl acrylate and methyl ethyl ketoxime, 2-[0-(1'-methylpropyleneamino)carboxyamino]ethyl acrylate, manufactured by Resonaq Corporation), MOI-BM: Karenz (registered trademark) MOI-BM (reaction product of 2-isocyanatoethyl methacrylate and methyl ethyl ketoxime, 2-[0-(1'-methylpropyrideneamino)carboxyamino]ethyl methacrylate, manufactured by Resonaq Corporation), Examples include AOI-MDE: Karenz® AOI-MDE (a reaction product of 2-isocyanatoethyl acrylate and diethyl malate, 2-[(diethyl malate)carbonylamino]ethyl acrylate, manufactured by Resonaq Corporation).

[0034] From the viewpoint of storage stability, availability, and neutrality after desorption of the colored curable resin composition, compound (α) is particularly preferably 2-[[[[2-[1-oxo-2-propenyl]oxy]ethyl]amino]carbonyl]-1,3-diethyl malonate or 2-[[[[2-[2-methyl-1-oxo-2-propenyl]oxy]ethyl]amino]carbonyl]-1,3-diethyl malonate.

[0035] The proportion of constituent unit (I) is preferably 2 to 98 mol%, more preferably 5 to 60 mol%, and even more preferably 10 to 45 mol%, of the total structural units constituting the resin [BQ]. Within this range, curing by post-bake at low temperatures is facilitated.

[0036] Examples of resins (BQ) include the following resins [BQ1] to [BQ4]. Resin [BQ1]; a copolymer having structural unit (I) and structural units derived from at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "(a)"); Resin [BQ2]; a copolymer having structural unit (I), structural units derived from (a), and structural units derived from monomers having a hydroxyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)"); Resin [BQ3]; a copolymer having structural unit (I), structural units derived from (a), and structural units derived from monomers copolymerizable with (a) (however different from (a) and (b)) (hereinafter sometimes referred to as "(c)"); Examples include resins [BQ4]; copolymers having structural unit (I), structural unit derived from (a), structural unit derived from (b), and structural unit derived from (c).

[0037] (a) Specifically, for example, Unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing carboxyl groups, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride; Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate; Examples include unsaturated acrylates containing both a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Of these, acrylic acid, methacrylic acid, and the like are preferred from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions.

[0038] The hydroxyl group in (b) is favorable for reaction with the isocyanate group after dissociation of the isocyanate protecting group in formula (Q). Therefore, the presence of structural units derived from (b) in the resin (BQ) facilitates the formation of a good pattern shape in the color filter. Furthermore, in terms of forming a good pattern shape, it is preferable that the hydroxyl group is an alcoholic hydroxyl group. Specifically, (b) includes, for example, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 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, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5, Examples include 6-di(2'-hydroxyethyl)bicyclo[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, and 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, with 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate being preferred, and 2-hydroxyethyl (meth)acrylate being more preferred. With these, a colored curable resin composition that can easily form a color filter with sufficient chemical resistance can be obtained.

[0039] When the resin (BQ) has structural units derived from (b), the proportion of structural units derived from (b) is preferably 2 to 90 mol%, more preferably 5 to 60 mol%, and even more preferably 8 to 30 mol% of the total structural units constituting the resin [BQ]. Within this range, a good pattern shape is more easily formed in the color filter.

[0040] (c) For example, Monomers having a cyclic ether structure with 2 to 4 carbon atoms and ethylenically unsaturated bonds (hereinafter sometimes referred to as "(d)"); Methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 decan-8-yl (meth)acrylate (commonly known as "dicyclopentanyl (meth)acrylate" in the art, and may also be referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 decen-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the art), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate and other (meth)acrylic acid esters; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and 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-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-tert-butoxy Bicyclounsaturated compounds such as carbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl)maleimide; Examples include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like. Of these, (meth)acrylic acid esters are preferred.

[0041] (d) refers to a polymerizable compound having, for example, a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (d) is preferably a monomer having a cyclic ether structure with 2 to 4 carbon atoms and a (meth)acryloyloxy group. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0042] Examples of (d) include monomers having an oxyranyl group and an ethylenically unsaturated bond (d1) (hereinafter sometimes referred to as "(d1)"), monomers having an oxetanyl group and an ethylenically unsaturated bond (d2) (hereinafter sometimes referred to as "(d2)"), and monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (d3) (hereinafter sometimes referred to as "(d3)").

[0043] Examples of (d1) include monomers having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized (d1-1) (hereinafter sometimes referred to as "(d1-1)") and monomers having a cyclic unsaturated hydrocarbon structure that has been epoxidized (d1-2) (hereinafter sometimes referred to as "(d1-2)").

[0044] (d1-1) includes glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis(glycidyl Examples include oxymethylstyrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0045] (d1-2) includes vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), and 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decane-8-yl (meth)acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 Examples include decane-9-yl(meth)acrylate.

[0046] For (d2), monomers having an oxetanyl group and a (meth)acryloyloxy group are more preferred. Examples of (d2) include 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, and 3-ethyl-3-acryloyloxyethyl oxetane.

[0047] For (d3), monomers having a tetrahydrofurfuryl group and a (meth)acryloyloxy group are more preferred. Specifically, examples of (d3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0048] In particular, (c) is preferably a monomer represented by formula (1). That is, the resin (BQ) may have structural units derived from the monomer represented by formula (1).

[0049] [ka]

[0050] [In formula (1), R 1 R represents a hydrogen atom or a methyl group. 2 [This represents a linear or branched alkyl group having 6 to 25 carbon atoms.]

[0051] R 2 The number of carbon atoms is preferably 6 to 25, more preferably 7 to 20, and even more preferably 8 to 18. 2 When the number of carbon atoms is within the above range, a colored curable resin composition capable of forming a color filter with sufficient haze can be obtained.

[0052] R 2 It is preferable that R is a branched alkyl group. 2 Preferred branched alkyl groups in this product include 2-ethylhexyl group, 2-hexyldecyl group, and 2-butyloctyl group.

[0053] Examples of monomers represented by formula (1) include heptyl (meth)acrylate, octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isononyl (meth)acrylate, dodecyl (meth)acrylate, isodecyl (meth)acrylate, hexadecyl (meth)acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate, and docosyl (meth)acrylate, with 2-ethylhexyl (meth)acrylate being preferred. Using these, a colored curable resin composition that can easily form a color filter with sufficient haze can be obtained.

[0054] When the resin (BQ) has structural units derived from the monomer represented by formula (1), the proportion of structural units derived from the monomer represented by formula (1) is preferably 2 to 100 mol%, more preferably 20 to 95 mol%, and even more preferably 55 to 90 mol%, of the total structural units derived from (c). Within this range, a colored curable resin composition capable of forming a color filter with sufficient haze can be obtained.

[0055] In resin [BQ1], the ratio of structural units derived from each is, among all structural units constituting resin [BQ1], Structural unit (I); 2-98 mol% (a) Structural units derived from (a); 2-98 mol% It is preferable that this be the case. Structural unit (I); 5-60 mol% (a) Structural units derived from (a); 40-95 mol% It is preferable that it be so. When the ratio of structural units of the resin [BQ1] falls within the above range, good pattern shapes are more easily formed in the color filter. Furthermore, the colored curable resin composition tends to have excellent storage stability, developability when forming patterns, and the resulting cured film exhibits superior solvent resistance, heat resistance, and mechanical strength.

[0056] The resin [BQ1] can be manufactured, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited literature.

[0057] Specifically, a method involves placing predetermined amounts of compounds (α) and (a), a polymerization initiator, and a solvent into a reaction vessel, creating a deoxygenated atmosphere by, for example, replacing oxygen with nitrogen, and heating and maintaining the temperature while stirring. The polymerization initiator and solvent used here are not particularly limited and can be those commonly used in the field. For example, examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, tert-butylperoxy-2-ethylhexanoate, etc.), and the solvent can be any solvent that dissolves each monomer. Examples of solvents that can be included in the colored curable resin composition of the present invention include those described later.

[0058] The resulting copolymer may be used as is after the reaction, or after being concentrated or diluted, or after being extracted as a solid (powder) by methods such as reprecipitation. In particular, by using the solvent contained in the colored curable resin composition of the present invention as the solvent during polymerization, the solution after the reaction can be used directly in the preparation of the colored curable resin composition of the present invention, thereby simplifying the manufacturing process of the colored curable resin composition of the present invention.

[0059] In resin [BQ2], the ratio of structural units derived from each is, among all structural units constituting resin [BQ2], Structural unit (I); 2-98 mol% (a) Structural units derived from (a); 2-55 mol% (b) Structural units derived from (b); 2-85 mol% It is preferable that this be the case. Structural unit (I); 5-45 mol% (a) Structural units derived from (a); 5-45 mol% (b) Structural units derived from (b); 5-60 mol% It is preferable that it be so. When the ratio of structural units of the resin [BQ2] falls within the above range, good pattern shapes are more easily formed in the color filter. Furthermore, the colored curable resin composition tends to have excellent storage stability, developability when forming patterns, and the resulting cured film exhibits superior solvent resistance, heat resistance, and mechanical strength.

[0060] Resin [BQ2] can be manufactured in the same manner as described for the manufacturing method of resin [BQ1], except that the raw materials are changed to compounds (α), (a), and (b).

[0061] In resin [BQ3], the ratio of structural units derived from each is, among all structural units constituting resin [BQ3], Structural unit (I); 2-98 mol% (a) Structural units derived from (a); 2-55 mol% (c) Structural units derived from (c) 2-98 mol% It is preferable that this be the case. Structural unit (I); 5-45 mol% (a) Structural units derived from (a); 5-45 mol% (c) Structural units derived from (c); 55-90 mol% It is preferable that it be so. When the ratio of structural units of the resin [BQ3] falls within the above range, good pattern shapes are more easily formed in the color filter. Furthermore, the colored curable resin composition tends to have excellent storage stability, developability when forming patterns, and the resulting cured film exhibits superior solvent resistance, heat resistance, and mechanical strength.

[0062] Resin [BQ3] can be manufactured in the same manner as described for the manufacturing method of resin [BQ1], except that the raw materials are changed to compounds (α), (a), and (c).

[0063] In resin [BQ4], the ratio of structural units derived from each is, among all structural units constituting resin [BQ4], Structural unit (I); 2-98 mol% (a) Structural units derived from (a); 2-55 mol% (b) Structural units derived from (b); 2-85 mol% (c) Structural units derived from (c) 2-98 mol% It is preferable that this be the case. Structural unit (I); 5-45 mol% (a) Structural units derived from (a); 5-45 mol% (b) Structural units derived from (b); 5-60 mol% (c) Structural units derived from (c); 55-90 mol% It is preferable that it be so. When the ratio of structural units of the resin [BQ4] falls within the above range, good pattern shapes are more easily formed in the color filter. Furthermore, the colored curable resin composition tends to have excellent storage stability, developability when forming patterns, and the resulting cured film exhibits superior solvent resistance, heat resistance, and mechanical strength.

[0064] Resin [BQ4] can be manufactured in the same manner as described for the manufacturing method of resin [BQ1], except that the raw materials are changed to compounds (α), (a), (b), and (c).

[0065] The color-curable resin composition of the present invention may contain one type of resin (BQ), or it may contain a combination of two or more types of resins (BQ).

[0066] Among these, resin [BQ4] is preferred as the resin [BQ] due to its storage stability and ability to form a good pattern shape.

[0067] The resin may also include other resins different from resin (BQ) (hereinafter sometimes referred to as "other resins (BR)"). Examples of other resins (BR) include resins having a group represented by formula (Q) and a polystyrene-based weight-average molecular weight (Mw) of less than 17,000, and resins that do not have a group represented by formula (Q). Resins that do not have a group represented by formula (Q) are preferably alkali-soluble resins, and examples include the following resins [K1] to [K6]. As resins [K1] to [K6], for example, the resins described in Japanese Patent Publication No. 2024-129724 may be appropriately referenced. When other resins (BR) are included, they may be used individually or in combination of two or more types. Resin [K1]; a copolymer having structural units derived from (a) and structural units derived from (d); Resin [K2]; a copolymer having structural units derived from (a), structural units derived from (d), and structural units derived from (c); Resin [K3]; a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]; a copolymer having structural units obtained by adding (d) to structural units derived from (a) and structural units derived from (c), and containing structural units derived from (a) to which (d) is not added; Resin [K4']; a copolymer having structural units derived from (a) to which (d) is added, and structural units derived from (c), and not containing structural units derived from (a) to which (d) is not added; Resin [K5]; Copolymer having structural units obtained by adding (a) to structural units derived from (d) and structural units derived from (c) (may include structural units derived from (d) to which (a) is not added, but it is preferable that they are not included); A copolymer having a structural unit obtained by adding (a) to a structural unit derived from resin [K6] (d), and further adding a carboxylic acid anhydride, and a structural unit derived from (c). The resins [K1] to [K6] may optionally contain structural units derived from (b).

[0068] A structural unit obtained by adding (d) to a structural unit derived from (a) is a unit formed by adding (d) to a structural unit derived from (a) that constitutes the main chain of the copolymer, and has a pendant unsaturated group derived from (d). In this structural unit, (a) and (d) may be any of the examples above. Unsaturated monocarboxylic acids are preferred as (a). (d) is preferred as (d1), and (d1-1) is more preferred.

[0069] A structural unit obtained by adding (a) to a structural unit derived from (d) is a unit formed by adding (a) to a structural unit derived from (d) that constitutes the main chain of the copolymer, and has a pendant unsaturated group derived from (a). In this structural unit, (a) and (d) may be any of the examples above. As (a), unsaturated monocarboxylic acids are preferred. As (d), (d1) is preferred, and (d1-1) is more preferred.

[0070] A structural unit obtained by adding (a) to a structural unit derived from (d) and then adding a carboxylic acid anhydride is a structural unit in which a hydroxyl group formed by the addition of (a) to a structural unit derived from (d) that constitutes the main chain of the copolymer is bonded to by the carboxylic acid anhydride through half-esterification, and has a pendant carboxyl group derived from the carboxylic acid anhydride and a pendant unsaturated group derived from (a). In this structural unit, (a) and (d) may be any of the examples above. Unsaturated monocarboxylic acids are preferred as (a). (d1) is preferred as (d), and (d1-1) is more preferred.

[0071] Examples of carboxylic acid anhydrides include saturated aliphatic polycarboxylic acid anhydrides such as malonic acid anhydride, succinic acid anhydride, glutaric acid anhydride, and adipic acid anhydride; unsaturated aliphatic polycarboxylic acid anhydrides such as maleic acid anhydride, citraconic acid anhydride, and itaconic acid anhydride; aromatic polycarboxylic acid anhydrides such as 3-vinylphthalic acid anhydride and 4-vinylphthalic acid anhydride; and polycarboxylic acid anhydrides such as alicyclic polycarboxylic acid anhydrides such as 3,4,5,6-tetrahydrophthalic acid anhydride, 1,2,3,6-tetrahydrophthalic acid anhydride, dimethyltetrahydrophthalic acid anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, with saturated aliphatic polycarboxylic acid anhydrides being preferred.

[0072] The resin (BR) preferably contains at least one selected from the group consisting of resins [K1] to resins [K6], more preferably contains at least one selected from the group consisting of resins [K1] to resins [K4] from the viewpoint of curability, and even more preferably contains resin [K2] and / or resin [K4].

[0073] Specifically, the resin (BR) is a copolymer of 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resins such as decyl (meth)acrylate / (meth)acrylic acid copolymer [K1]; Glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl (meth)acrylate / (meth)acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / tricyclo[5.2.1.0 2,6 ] Decen-8-yl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl (meth)acrylate / (meth)acrylic acid / benzyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resins such as decyl (meth)acrylate / (meth)acrylic acid / phenoxybenzyl (meth)acrylate copolymer and 3-methyl-3-(meth)acryloyloxymethyl oxetane / (meth)acrylic acid / styrene copolymer [K2]; Resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymers and styrene / (meth)acrylic acid copolymers [K3]; Resins such as those obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a benzyl (meth)acrylate / dicyclopentanyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a norbornene / vinyltoluene / (meth)acrylic acid copolymer, and resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a norbornene / styrene / (meth)acrylic acid copolymer [K4]; Resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / (meth)acrylic acid copolymer with glycidyl (meth)acrylate, and resins obtained by reacting a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer with glycidyl (meth)acrylate [K4']; Resins such as resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, and resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid [K5]; Examples of resins include those obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then reacting that with tetrahydrophthalic anhydride; a resin obtained by reacting a 2-ethylhexyl (meth)acrylate / tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then reacting that with succinic anhydride; and a resin obtained by reacting a methyl (meth)acrylate / 2-ethylhexyl (meth)acrylate / tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then reacting that with succinic anhydride [K6].

[0074] The weight-average molecular weight of the resin (BQ) in terms of polystyrene is 17,000 or more, preferably 17,000 to 100,000, more preferably 18,000 to 70,000, even more preferably 19,000 to 50,000, and even more preferably 25,000 to 40,000. When the weight-average molecular weight is within the above range, a color filter with a good pattern shape can be easily formed. In addition, the hardness of the color filter (cured film) is improved, the residual film rate is high, the solubility of the unexposed areas in the developer is good, and the resolution of the pattern tends to improve.

[0075] The weight-average molecular weight of the resin (BR) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 60,000, and even more preferably 5,000 to 40,000. When the molecular weight is within the above range, the hardness of the color filter improves, the residual film rate increases, the solubility of the unexposed areas in the developer solution improves, and the resolution of the color pattern tends to improve.

[0076] The weight-average molecular weight (Mw) of resin (BQ) and resin (BR) in terms of polystyrene is measured by the GPC method. More specifically, it can be measured by the method described in the examples below.

[0077] The degree of dispersion of the resin (BQ) [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] is preferably 1.1 to 6, and more preferably 1.2 to 4. The weight-average molecular weight (Mw) of the resin (BQ) in terms of polystyrene was measured by the GPC method. More specifically, it can be measured by the method described in the examples below.

[0078] The acid value of the resin (BQ) is preferably 10 to 170 mg-KOH / g, more preferably 20 to 150 mg-KOH / g, and even more preferably 30 to 135 mg-KOH / g, based on solid content. Here, the acid value is measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0079] The acid value of the resin (BR) is preferably 20 to 170 mg-KOH / g, more preferably 25 to 150 mg-KOH / g, and even more preferably 30 to 135 mg-KOH / g, based on solid content. By setting the acid value of the resin (BR) within the above range, good developability can be achieved.

[0080] The resin content is preferably 20 to 60% by mass, more preferably 30 to 55% by mass, and even more preferably 40 to 50% by mass, relative to the total amount of solids in the colored curable resin composition. When the resin content is within the above range, a good pattern shape is easily formed in the color filter. It also tends to improve the curability of the colored curable resin composition, and the resolution of the pattern and the residual film rate tend to improve. In this specification, "total amount of solids" refers to the amount obtained by subtracting the solvent content from the total amount of the colored curable resin composition. The total amount of solids and the content of each component therein can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0081] The resin (BQ) content is preferably 60 to 100% by mass, more preferably 70 to 100% by mass, even more preferably 80 to 100% by mass, and even more preferably 90 to 100% by mass, relative to 100% by mass of the resin, and may also be 100% by mass. When the resin (BQ) content is within the above range, a good pattern shape is easily formed in the color filter.

[0082] The content of other resins is preferably 0 to 40% by mass, more preferably 0 to 20% by mass, and even more preferably 0 to 10% by mass, relative to the total amount of solids in the colored curable resin composition. Other resins do not need to be included in the resins constituting the colored curable resin composition (i.e., they may be 0% by mass). When the content of other resins is within the above range, a good pattern shape is easily formed in the color filter.

[0083] (polymerizable compound) In this specification, polymerizable compounds are compounds that can be polymerized by active radicals and / or acids generated from polymerization initiators, and examples include compounds having polymerizable ethylenically unsaturated bonds (preferably (meth)acryloyl groups). Polymerizable compounds containing (meth)acryloyl groups are typically compounds that can be polymerized by active radicals generated from polymerization initiators, such as those resulting from light irradiation.

[0084] As polymerizable compounds, for example, those having two or more ethylenically unsaturated bonds can be used, and those having three or more ethylenically unsaturated bonds are preferred. 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, tripentaerythritol hexa(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, and tris(2-(meth)acrylo Examples include yloxyethyl 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, glycerin tri(meth)acrylate, glycerin di(meth)acrylate, and compounds represented by formula (z).

[0085] [ka]

[0086] [In equation (z), m+n ≈ 2~30]

[0087] In particular, from the viewpoint of availability and surface hardness, polymerizable compounds are preferably, for example, chain-type aliphatic polymerizable compounds. Furthermore, it is preferable that the polymerizable compound has 2 to 8 (preferably 3 to 8) ethylenically unsaturated bonds. When the polymerizable compound has 2 to 8 (preferably 3 to 8) ethylenically unsaturated bonds, a good pattern shape is easily formed in the color filter. From this perspective, it is preferable that the polymerizable compound includes one or more selected from the group consisting of trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, and the compound represented by formula (z). It is more preferable that the polymerizable compound includes one or more selected from the group consisting of dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, and tripentaerythritol hepta(meth)acrylate.

[0088] The number-average molecular weight of the polymerizable compound is preferably 150 to 2,900, more preferably 200 to 2,000, and even more preferably 250 to 1,500. Within this range, cracks and peeling are less likely to occur in the coloring pattern, and the curability of the colored curable resin composition can be easily adjusted to an appropriate range. The number-average molecular weight (Mn) can be measured, for example, using gel permeation chromatography (GPC). More specifically, it can be measured by the method described in the examples below.

[0089] The hydroxyl value of the polymerizable compound should preferably be less than 100 mg / KOH. When it is within this range, when the coating film of the colored curable resin composition is exposed to light and cured, variations in the degree of curing within the coating film are less likely to occur, and in particular, it becomes possible to cure the coating film thoroughly to its depths, making it easier to obtain a good coloring pattern.

[0090] The polymerizable compound content is preferably 5 to 50% by mass, more preferably 8 to 45% by mass, and even more preferably 12 to 40% by mass, relative to the total amount of solids in the colored curable resin composition. When the polymerizable compound content is within the above range, when the coating film of the colored curable resin composition is exposed and cured, variations in the degree of curing within the coating film are less likely to occur, and in particular, it becomes possible to cure the coating film sufficiently to its depths, making it easier to obtain a good coloring pattern.

[0091] The polymerizable compound content is preferably 10 to 85 parts by mass, more preferably 20 to 65 parts by mass, and even more preferably 30 to 45 parts by mass, per 100 parts by mass of resin. When the polymerizable compound content is within the above range per 100 parts by mass of resin, when the coating film of the colored curable resin composition is exposed and cured, variations in the degree of curing within the coating film are less likely to occur, and in particular, it becomes possible to sufficiently cure the coating film to its depths, making it easier to obtain a good coloring pattern.

[0092] (Polymerization initiator) Polymerization initiators are compounds that generate active radicals, acids, etc., upon the action of light or heat, thereby initiating polymerization. Polymerization initiators are not particularly limited, but examples include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds. Among these, O-acyloxime compounds are preferred. From the viewpoint of further improving the curability of the colored curable resin composition, polymerization initiators preferably have a maximum absorption wavelength in the range of 365 to 390 nm, and more preferably in the range of 370 to 390 nm.

[0093] O-acyloxime compounds are preferred as polymerization initiators. Furthermore, it is also preferable that the polymerization initiator is a compound having a nitro group.

[0094] O-acyloxime compounds are given by formula (c1): [ka] This is a compound having the structure represented by . Hereafter, * represents a bond.

[0095] Examples of the O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N- Examples include acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (all manufactured by BASF), N-1919, NCI-730, NCI-831, NCI-930 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, PBG-329 (all manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), Nikkacure YJ-04(T), Nikkacure IW-15, Nikkacure TG-10, Nikkacure TG-05 (all manufactured by Nippon Chemical Industries, Ltd.) may also be used.In particular, the O-acyloxime compound is preferably at least one selected from the group consisting of N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and NikkacureIW-15. These O-acyloxime compounds tend to produce high-brightness color filters.

[0096] Alkylphenone compounds are compounds having a substructure represented by formula (d4) or formula (d5). In these substructures, the benzene ring may have substituents.

[0097] [ka]

[0098] Compounds having the structure represented by formula (d4) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used. Compounds having the structure represented by formula (d5) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyldimethyl ketal. In terms of sensitivity, alkylphenone compounds having the structure represented by formula (d4) are preferred.

[0099] Examples of biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Publication No. 6-75372, Japanese Patent Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2-chlorophenyl Examples include phenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group (see, for example, Japanese Patent Application Publication No. 7-10913, etc.). Among these, compounds represented by the following formula and mixtures thereof are preferred.

[0100] [ka]

[0101] Examples of triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-( Examples include 5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0102] Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

[0103] The polymerization initiator content is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, even more preferably 1 to 12 parts by mass, and particularly preferably 1 to 7 parts by mass, based on 100 parts by mass of the total amount of resin and polymerizable compound contained in the colored curable resin composition. When the polymerization initiator content is within the above range, it is easier to form a pattern with a good shape by exposure and development, and it is easier to improve curability at low temperatures. In addition, since sensitivity tends to be increased and exposure time is shortened, the productivity of color filters and the like is improved.

[0104] (Potassium initiation aid) The colored curable resin composition of the present invention may further contain at least one polymerization initiator. A polymerization initiator is a compound or sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When a polymerization initiator is included, it is usually used in combination with a polymerization initiator. Examples of polymerization initiators include 4,4'-bis(dimethylamino)benzophenone (commonly known as Michlaz's ketone), 4,4'-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, and N-phenylglycine.

[0105] When these polymerization initiators are used, their content is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, per 100 parts by mass of the total amount of resin and polymerizable compound. When the amount of polymerization initiator is within this range, patterns can be formed with even higher sensitivity during exposure, and the productivity of color filters and the like tends to improve.

[0106] (Silane coupling agent) The color-curable resin composition of the present invention may further contain at least one silane coupling agent to promote adhesion to the substrate. Examples of silane coupling agents include those having vinyl groups, epoxy groups, styryl groups, methacryloyloxy groups, acryloyloxy groups, amino groups, ureido groups, isocyanate groups, isocyanurate groups, mercapto groups, chloropropyl groups, and sulfide groups. The silane coupling agent may be of the methoxy type or ethoxy type, and may be of the dialkoxy type or trialkoxy type.

[0107] As a silane coupling agent, Vinyl group-containing silane coupling agents such as vinyltrimethoxysilane, vinyltriethoxysilane, and vinyltris(2-methoxyethoxy)silane; Epoxy group-containing silane coupling agents such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropyltriethoxysilane; Styryl group-containing silane coupling agents such as p-styryltrimethoxysilane; 3-Methacryloyloxypropylmethyldimethoxysilane, 3-Methacryloyloxypropyltrimethoxysilane, 3-Methacryloyloxypropylmethyldiethoxysilane, 3-Methacryloyloxypropyltriethoxysilane, and other methacryloyloxy group-containing silane coupling agents; 3-Acryloyloxypropylmethyldimethoxysilane, 3-Acryloyloxypropyltrimethoxysilane, 3-Acryloyloxypropylmethyldiethoxysilane, 3-Acryloyloxypropyltriethoxysilane, and other silane coupling agents containing acryloyloxy groups; N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriisopropoxysilane, N-(2-aminoethyl)-3-aminopropyltributoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldiisopropoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldibutoxysilane, N-(2-aminoethyl)-3-aminopropylethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropylethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropylethyldiisopropoxysilane, N-(2-aminoethyl)-3-aminopropylethyldibutoxy silane coupling agents containing amino groups, such as silane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyltriisopropoxysilane, 3-aminopropyltributoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-aminopropylmethyldiisopropoxysilane, 3-aminopropylmethyldibutoxysilane, 3-aminopropylethyldimethoxysilane, 3-aminopropylethyldiethoxysilane, 3-aminopropylethyldiisopropoxysilane, 3-aminopropylethyldibutoxysilane, 3-aminopropyltriacetoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, and hydrochloride salts of N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane; Ureido group-containing silane coupling agents such as 3-ureidopropylmethyldimethoxysilane, 3-ureidopropyltrimethoxysilane, 3-ureidopropylmethyldiethoxysilane, and 3-ureidopropyltriethoxysilane; Isocyanato group-containing silane coupling agents such as 3-isocyanatopropylmethyldimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropylmethyldiethoxysilane, and 3-isocyanatopropyltriethoxysilane; Isocyanurate group-containing silane coupling agents such as tris-(trimethoxysilylpropyl)isocyanurate; Mercapto group-containing silane coupling agents such as 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldiethoxysilane, and 3-mercaptopropyltriethoxysilane; Chloropropyl group-containing silane coupling agents such as 3-chloropropylmethyldimethoxysilane and 3-chloropropyltrimethoxysilane; Examples include sulfide group-containing silane coupling agents such as bis(triethoxysilylpropyl)tetrasulfide, bis(methyldimethoxysilylpropyl)tetrasulfide, and bis(methyldiethoxysilylpropyl)tetrasulfide. Furthermore, as mentioned above, amino group-containing silane coupling agents also include silane coupling agents that contain an amino group after deprotection. Specifically, examples include ketimine structure-containing silane coupling agents such as 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine. Among these, epoxy group-containing silane coupling agents, methacryloyloxy group-containing silane coupling agents, acryloyloxy group-containing silane coupling agents, amino group-containing silane coupling agents, ureido group-containing silane coupling agents, isocyanate group-containing silane coupling agents, and isocyanurate group-containing silane coupling agents are preferred.

[0108] As a silane coupling agent, nitrogen-containing silane coupling agents that contain nitrogen atoms in their molecule are preferred. Nitrogen-containing silane coupling agents can improve the chemical resistance of color filters. Examples of nitrogen-containing silane coupling agents include amino group-containing silane coupling agents, ureido group-containing silane coupling agents, isocyanate group-containing silane coupling agents, and isocyanurate group-containing silane coupling agents.

[0109] The nitrogen-containing silane coupling agent preferably has a molecular weight of 310 or less. Within this range, the chemical resistance of the color filter is good, and it tends to develop well and produce less residue.

[0110] Examples of silane coupling agents include 3-methacryloyloxypropylmethyldimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, and 3-isocyanatopropylmethyldiethyl Toxysilane and 3-isocyanatopropyltriethoxysilane are preferred, and N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, 3-isocyanatopropylmethyldiethoxysilane, and 3-isocyanatopropyltriethoxysilane are more preferred.

[0111] The silane coupling agent content is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass, and even more preferably 0.5 to 5% by mass, relative to the total amount of solids in the colored curable resin composition of the present invention. Within this range, adhesion between the resist layer and the substrate is improved.

[0112] Furthermore, the nitrogen-containing silane coupling agent content is preferably 60 to 100% by mass, more preferably 70 to 100% by mass, even more preferably 80 to 100% by mass, and even more preferably 90 to 100% by mass, based on 100% by mass of the silane coupling agent. Within this range, the chemical resistance of the color filter can be improved.

[0113] (solvent) The color-curable resin composition of the present invention may further contain at least one solvent. The solvent is not particularly limited, and solvents commonly used in the art can be used. Examples include ester solvents (solvents containing -COO- in the molecule but not -O-), ether solvents (solvents containing -O- in the molecule but not -COO-), ether ester solvents (solvents containing both -COO- and -O- in the molecule), ketone solvents (solvents containing both -CO- in the molecule but not -COO-), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxides, and the like.

[0114] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0115] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethole, and methylanisole.

[0116] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxy-2-methylpropionate Examples include ethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

[0117] 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, diacetone alcohol, and isophorone.

[0118] Examples of alcoholic solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0119] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0120] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0121] The solvent preferably contains one or more selected from the group consisting of ether solvents, ether ester solvents, and ketone solvents, more preferably contains an ether solvent or an ether ester solvent, and even more preferably contains propylene glycol monomethyl ether or propylene glycol monomethyl ether acetate.

[0122] The solvent content is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, relative to the total amount of the colored curable resin composition of the present invention. In other words, the solid content of the colored curable resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. When the solvent content is within the above range, the flatness during application is good, and the display characteristics tend to be good because, for example, there is no shortage of color density when a color filter is formed.

[0123] (Leveling agent) The colored curable resin composition of the present invention may further contain at least one leveling agent. Examples of leveling agents include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having a fluorine atom. These may have polymerizable groups in their side chains.

[0124] Examples of silicone-based surfactants include surfactants that have siloxane bonds in their molecules. Specifically, examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0125] Examples of the aforementioned fluorine-based surfactants include surfactants having fluorocarbon chains in their molecules. Specifically, these include Florard® FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac® F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top® EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon® S381, S382, SC101, SC105 (manufactured by AGC Inc. (formerly Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

[0126] Examples of silicone-based surfactants containing fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in their molecules. Specifically, examples include Megafac® R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0127] When a leveling agent is included, the content of the leveling agent is preferably 0.0005 to 0.2% by mass, and more preferably 0.0008 to 0.1% by mass, relative to the total amount of the colored curable resin composition. This content does not include the content of the pigment dispersant. When the content of the leveling agent is within the above range, the flatness of the cured film of the colored curable resin composition of the present invention, which is used as a color filter or the like, can be improved.

[0128] (Other ingredients) The colored curable resin composition of the present invention may optionally contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents.

[0129] (Method for producing a colored curable resin composition) The colored curable resin composition of the present invention can be prepared, for example, by mixing a colorant, a resin, a polymerizable compound, and a polymerization initiator, and optionally a polymerization initiator aid, a silane coupling agent, a solvent, a leveling agent, and other components. The coloring agent may be prepared using the pigment dispersion described above. In this case, the desired colored curable resin composition can be prepared by mixing the remaining components with the pigment dispersion to a predetermined concentration. It is also preferable to filter the mixed colored curable resin composition through a filter with a pore size of approximately 0.01 to 10 μm.

[0130] (How to manufacture color filters) A color filter of the present invention can be obtained as a cured film of the color curable resin composition of the present invention. The color filter of the present invention can be obtained, for example, by a manufacturing method that includes the steps of applying the color curable resin composition of the present invention and pre-baking to form a composition, exposing the obtained composition layer through a mask, developing the exposed composition layer to form a pattern, and performing post-baking on the obtained pattern. Methods for forming the pattern from the colored curable resin composition of the present invention include, for example, photolithography, inkjet printing, and printing, with photolithography being preferred.

[0131] The aforementioned patterns (e.g., each color pixel) can be formed using, for example, known or conventional apparatus and conditions. For example, they can be fabricated by photolithography as follows.

[0132] First, a colored curable resin composition is applied to a substrate, and volatile components such as solvents are removed by pre-baking (heat drying and / or vacuum drying), followed by drying to obtain a smooth composition layer. As substrates, glass plates such as quartz glass, borosilicate glass, aluminasilate glass, and soda-lime glass with a silica coating on the surface are used; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and substrates on which aluminum, silver, or silver / copper / palladium alloy thin films are formed. Other cured films (e.g., other color filters), resin layers, transistors, circuits, etc. may be formed on these substrates. Coating methods include spin coating, slit coating, and slit and spin coating. The temperature for heat drying is preferably 30 to 120°C, and more preferably 50 to 110°C. 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 do so under a pressure of 50 to 150 Pa and at a temperature range of 20 to 25°C. The thickness of the composition layer is not particularly limited and can be appropriately selected according to the desired thickness of the cured film.

[0133] Next, the composition layer is exposed through a photomask to form the desired pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate to the intended application is used. For exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferred. For example, light below 350 nm can be filtered out using a filter that cuts out this wavelength range, or light around 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specifically, examples of light sources include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. Furthermore, the exposure dose based on a wavelength of 365 nm is 50 to 300 mJ / cm². 2 Preferably, the concentration is 60-200 mJ / cm². 2 It is more preferable that the concentration be between 65 and 180 mJ / cm². 2 It is even more preferable that this be the case. It is preferable to use an exposure apparatus such as a mask aligner and a stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light rays and precise alignment between the photomask and the substrate on which the resin composition layer is formed.

[0134] A (developed) pattern is formed on the substrate by bringing the exposed resin composition layer into contact with a developer solution for development. During development, the unexposed portions of the resin composition layer are dissolved and removed by the developer solution. As the developer solution, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. Furthermore, the developer solution may also contain a surfactant. The development method can be any of the following: paddle method, dipping method, or spray method. Furthermore, the substrate may be tilted to any angle during development. After developing, it is preferable to wash the film with water.

[0135] Furthermore, the obtained (developed) pattern is subjected to post-baking. The post-baking temperature is preferably 50 to 250°C, more preferably 50 to 120°C, even more preferably 60 to 100°C, and even more preferably 70 to 90°C. According to the color-curable resin composition of the present invention, even when used in organic light-emitting diodes (OLEDs) that cannot be processed at high temperatures, a color filter (cured film) with a good pattern shape can be obtained by post-baking at a low temperature, for example, 50°C to 120°C. The post-baking time is preferably 1 to 120 minutes, and more preferably 5 to 60 minutes.

[0136] (Color filter) The present invention also provides a color filter, which is a cured film of the color-curable resin composition of the present invention. The color filter of the present invention may be a cured film in which a pattern is formed on the color-curable resin composition of the present invention as described above. The thickness of the cured film is not particularly limited and can be adjusted as appropriate depending on the purpose and application, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, more preferably 0.3 to 6 μm, and even more preferably 0.5 to 4 μm. Furthermore, according to the present invention, a display device including the color filter can also be provided. A display device of the present invention that includes at least one color filter of the present invention as a component is useful as a display device with fewer display defects. Moreover, the color-curable resin composition of the present invention can form a good pattern shape by post-baking at low temperatures, making it particularly suitable as a color filter for an organic EL display device. [Examples]

[0137] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the examples, percentages and parts representing content or usage are by mass unless otherwise specified.

[0138] <Weight average molecular weight> The weight-average molecular weight (Mw) and number-average molecular weight (Mn) were measured using the GPC method under the following conditions. Equipment: HLC-8120GPC (manufactured by Tosoh Corporation) Column; TSK-GELG2000HXL Column temperature: 40°C Solvent: Tetrahydrofuran [THF] Flow rate: 1.0mL / min Test liquid solid content concentration: 0.001~0.01% by mass Injection volume: 50μL Detector; RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0139] <Acid value> 3 g of the resin solution was accurately weighed and dissolved in a mixed solvent of 90 g of acetone and 10 g of water. The acid value of the resin solution was measured using an automatic titrator (Hiranuma Sangyo Co., Ltd., product name: COM-555) with a 0.1 N KOH aqueous solution as the titrant. The acid value per gram of solids was then determined from the acid value of the solution and the solids content of the solution.

[0140] <Preparation Example 1: Preparation of Pigment Dispersion (A1)> CI Pigment Green 36 6.9 parts CI Pigment Yellow 139 1.9 parts CI Pigment Yellow 150 3.8 parts Acrylic pigment dispersant 4.2 parts Propylene glycol monomethyl ether acetate 79 parts A pigment dispersion (A1) was obtained by mixing the ingredients and thoroughly dispersing the pigment using a bead mill.

[0141] <Preparation Example 2: Preparation of Pigment Dispersion (A2)> CI Pigment Red 269 10.5 bu CI Pigment Yellow 139 2.1 parts Acrylic pigment dispersant 4.2 parts Propylene glycol monomethyl ether acetate 79 parts A pigment dispersion (A2) was obtained by mixing the ingredients and thoroughly dispersing the pigment using a bead mill.

[0142] <Preparation Example 3: Preparation of Pigment Dispersion (A3)> CI Pigment Blue 15:6 8.6 parts CI Pigment Violet 23 4.0 parts Acrylic pigment dispersant 4.2 parts Propylene glycol monomethyl ether acetate 79 parts A pigment dispersion (A3) was obtained by mixing the ingredients and thoroughly dispersing the pigment using a bead mill.

[0143] <Synthesis Example 1: Preparation of Resin (B1)> 1181 parts of propylene glycol monomethyl ether were added to a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube. The mixture was stirred while purging with nitrogen and the temperature was raised to 90°C. Next, 515 parts of 2-[[[[2-[1-oxo-2-propenyl]oxy]ethyl]amino]carbonyl]-1,3-diethyl malonate (Karenz® AOI-DEM; manufactured by Resonaq Co., Ltd.), 997 parts of 2-ethylhexyl acrylate, 173 parts of 2-hydroxyethyl methacrylate, 90 parts of methacrylic acid, 639 parts of propylene glycol monomethyl ether, and 817 parts of propylene glycol monoethyl ether acetate were mixed with 44.4 parts of dimethyl 2,2'-azobis(2-methylpropionate), and this mixture was added dropwise to the flask from a dropping funnel over a period of 1 hour. After the addition was complete, the mixture was stirred for a further 2 hours to carry out the copolymerization reaction and obtain the polymer. Finally, propylene glycol monomethyl ether acetate was added to the reaction solution to achieve a polymer solids concentration of 35%, yielding a resin (B1) solution with a weight-average molecular weight of 31600. The acid value per solids of resin (B1) was 35.7 mgKOH / g. It has the following structural units:

[0144] [ka]

[0145] <Synthesis Example 2: Preparation of Resin (B2)> 1195 parts of propylene glycol monomethyl ether were added to a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube, and the mixture was stirred while purging with nitrogen and heated to 90°C. Next, 83.4 parts of dimethyl 2,2'-azobis(2-methylpropionate) were added to a monomer mixture consisting of 504 parts of 2-[[[[2-[1-oxo-2-propenyl]oxy]ethyl]amino]carbonyl]-1,3-diethyl malonate (Karenz® AOI-DEM; manufactured by Resonaq Co., Ltd.), 975 parts of 2-ethylhexyl acrylate, 169 parts of 2-hydroxyethyl methacrylate, 88 parts of methacrylic acid, 625 parts of propylene glycol monomethyl ether, and 799 parts of propylene glycol monoethyl ether acetate. This mixture was then added dropwise to the flask from a dropping funnel over a period of 1 hour. After the dropwise addition was complete, the mixture was stirred for a further 2 hours to carry out the copolymerization reaction and obtain the polymer. Finally, propylene glycol monomethyl ether acetate was added to the reaction solution to achieve a polymer solids concentration of 35%, yielding a resin (B2) solution with a weight-average molecular weight of 19200. The acid value per solids of resin (B2) was 30.7 mgKOH / g.

[0146] <Synthesis Example 3: Preparation of Resin (B3)> 386 parts of propylene glycol monomethyl ether were added to a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube, and the mixture was stirred while purging with nitrogen, and the temperature was raised to 90°C. Next, 61.5 parts of dimethyl 2,2'-azobis(2-methylpropionate) were added to a monomer mixture consisting of 147 parts of 2-[[[[2-[1-oxo-2-propenyl]oxy]ethyl]amino]carbonyl]-1,3-diethyl malonate (Karenz® AOI-DEM; manufactured by Resonaq Co., Ltd.), 285 parts of 2-ethylhexyl acrylate, 50 parts of 2-hydroxyethyl methacrylate, 26 parts of methacrylic acid, 183 parts of propylene glycol monomethyl ether, and 234 parts of propylene glycol monoethyl ether acetate. This mixture was then added dropwise from a dropping funnel to the flask over a period of 1 hour. After the addition was complete, the mixture was stirred for a further 2 hours to carry out the copolymerization reaction and obtain the polymer. Finally, propylene glycol monomethyl ether acetate was added to the reaction solution to achieve a polymer solids concentration of 35%, yielding a resin (B3) solution with a weight-average molecular weight of 9000. The acid value per solids of resin (B3) was 32.7 mgKOH / g.

[0147] <Synthesis Example 4: Preparation of Resin (B4)> 349 parts of propylene glycol monomethyl ether acetate were added to a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube, and the mixture was stirred while purging with nitrogen, and the temperature was raised to 120°C. Next, 23.4 parts of t-butyl peroxy-2-ethylhexanoate were added to a monomer mixture consisting of 169.2 parts benzyl methacrylate, 103.3 parts methacrylic acid, and 52.9 parts dicyclopentanyl methacrylate, and this mixture was added dropwise to the flask from a dropping funnel over a period of 2 hours. After the addition was complete, the mixture was stirred for another 30 minutes to carry out the copolymerization reaction. Subsequently, the flask was purged with air, and 51.2 parts of glycidyl methacrylate, 1.1 parts of triphenylphosphine, and 1.1 parts of methoquinone were added. The reaction was continued at 120°C for 10 hours to obtain resin (B4). Finally, propylene glycol monomethyl ether acetate was added to the reaction solution to a solid content concentration of 40% to obtain resin (B4) solution. The weight-average molecular weight of resin (B4) was 10300, and the acid value per solid content was 38.2 mgKOH / g.

[0148] <Synthesis Example 5: Preparation of Resin (B5)> The flask, equipped with a reflux condenser, dropping funnel, and stirrer, was purged with nitrogen, and 371 parts of propylene glycol monomethyl ether acetate were introduced into the flask and heated to 85°C while stirring. Then, 54 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution consisting of 225 parts of decane-9-yl acrylate (trade name "E-DCPA", manufactured by Daicel Corporation), 81 parts of vinyltoluene (isomer mixture), and 80 parts of propylene glycol monomethyl ether acetate was added dropwise over 4 hours. Meanwhile, a solution prepared by dissolving the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the addition of the initiator solution was complete, the mixture was kept at the same temperature for 4 hours, and then cooled to room temperature. Finally, propylene glycol monomethyl ether acetate was added to the reaction solution to a solid content concentration of 37.5% to obtain resin (B5) solution. The weight-average molecular weight of resin (B5) was 10420, and the acid value per solid content was 112 mgKOH / g.

[0149] <Examples 1-14 and Comparative Example 1> (1) Preparation of a colored curable resin composition A colored curable resin composition was obtained by mixing the pigment dispersions (A1) to (A3) and each component listed in Table 1 in the amounts specified in Table 1. In preparing the colored curable resin composition, propylene glycol monomethyl ether acetate was mixed in so that the solid content of the colored curable resin composition was 18% by mass. In Table 1, the unit of each component's amount is "parts by mass," and the amounts of colorant, dispersant, resin, polymerizable compound, polymerization initiator, silane coupling agent, and leveling agent are expressed on a solid content basis. The colorant and dispersant are derived from the pigment dispersions (A1) to (A3).

[0150] [Table 1]

[0151] In Table 1, the components are as follows: Polymerizable compound (C1): Tripentaerythritol polyacrylate (NK ester A-TPE-30-NS; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; hydroxyl value 30 mg KOH / g) Polymerizable compound (C2): Mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate (NK Ester A-9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.; hydroxyl value 70 mg KOH / g) Polymerizable compound (C3): Trimethylolpropane triacrylate (NK ester A-TMPT; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) Polymerizable compound (C4): Ethoxylated bisphenol A diacrylate (NK ester ABE-300; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) Polymerizable compound (C5): Ethoxylated pentaerythritol tetraacrylate (NK ester ATM-35E; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) Polymerization initiator (D1): ADEKA ARCULUS® NCI-730 (manufactured by ADEKA Corporation) Polymerization initiator (D2): Nikkacure IW-15 (manufactured by Nippon Chemical Industrial Co., Ltd.; O-acyloxime compound) Silane coupling agent (E1): 3-methacryloyloxypropyltrimethoxysilane (KBM-503; manufactured by Shin-Etsu Silicone Co., Ltd.) Silane coupling agent (E2): N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (KBM-603; manufactured by Shin-Etsu Silicone Co., Ltd.) Silane coupling agent (E3): 3-aminopropyltriethoxysilane (KBE-903; manufactured by Shin-Etsu Silicone Co., Ltd.) Silane coupling agent (E4): 3-Isocyanatopropyltriethoxysilane (KBE-9007N; manufactured by Shin-Etsu Silicone Co., Ltd.) Silane coupling agent (E5): 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine (KBE-9103P; manufactured by Shin-Etsu Silicone Co., Ltd.) Leveling agent (F1): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0152] <Creating colored patterns (color filters)> The colored curable resin compositions of Examples 1-14 and Comparative Example 1, prepared as described above, were applied by spin coating onto a 5cm square glass substrate (Eagle 2000 (Corning)) to a post-baking film thickness of 3.0 μm. The substrate was then pre-baked at 85°C for 2 minutes to form a colored coating. After cooling, the colored coating formed on the substrate was exposed to 100 mJ / cm² of air using an exposure unit (TME-150RSK (Topcon Corporation)) under atmospheric conditions. 2 The samples were irradiated with light at an exposure level of 365 nm. A photomask with a 30 μm line-and-space pattern was used. After light irradiation, the colored composition layer was immersed in an aqueous developer containing 0.12% nonionic surfactant and 0.04% potassium hydroxide at 23°C for 70 seconds, rinsed with water, and post-baked at 85°C for 60 minutes to obtain a colored pattern.

[0153] <Evaluation of the taper angle of the colored pattern> The taper angle (θ) of the obtained colored patterns was measured using a scanning electron microscope (S-4000; Hitachi High-Technologies Corporation). Figure 1 shows a schematic diagram illustrating the method for measuring the taper angle. The taper angle (θ) is the angle between the line L connecting the point α where the tapered portion 2 touches surface S1 and the point β where the tapered portion 2 touches surface S2, when S1 and S2 are the surfaces that constitute the uniform thickness of the colored pattern 1, and surface S2. The smaller the taper angle is or the closer it is to 90°, the less likely cracks and peeling of the colored pattern are to occur. The results are shown in Table 2. It was found that the colored pattern obtained in Comparative Example 1 had a poor taper angle. In contrast, the taper angles of the colored patterns obtained in Examples 1 to 14 were good, ranging from 50° to 110°, which is close to 90°.

[0154] [Table 2]

[0155] <Evaluation of chemical resistance of colored patterns> The obtained colored patterns were immersed in propylene glycol monomethyl ether acetate at 23°C for 10 minutes, and then thoroughly washed with water. The xy chromaticity coordinates (x, y) and Y were measured before and after immersion, and the color difference △E*ab was calculated from these measurements using the method described in JIS Z 8730:2009 (7. Method for calculating color difference). The results are shown in Table 3. A smaller △E*ab indicates a smaller color change, and if △E*ab is 5.0 or less, the colored pattern can be considered practically acceptable as a color filter.

[0156] [Table 3] [Explanation of Symbols]

[0157] 1. Coloring pattern, 2. Tapered section, 3. Substrate

Claims

1. It contains a colorant, resin, polymerizable compound and polymerization initiator, A colorable curable resin composition comprising a resin (BQ) having a group represented by formula (Q) and having a polystyrene-based weight-average molecular weight (Mw) of 17,000 or more. 【Chemistry 1】 [In formula (Q), R Ｑ１ represents an isocyanate protecting group. * represents a bond.

2. The colored curable resin composition according to claim 1, wherein the resin (BQ) is an alkali-soluble resin.

3. The colored curable resin composition according to claim 1, wherein the resin (BQ) further comprises structural units derived from a monomer represented by formula (1). 【Chemistry 2】 [In formula (1), R １ R represents a hydrogen atom or a methyl group. ２ [This represents a linear or branched alkyl group having 6 to 25 carbon atoms.]

4. The colored curable resin composition according to claim 1, wherein the resin (BQ) further comprises structural units derived from monomers having hydroxyl groups and ethylenically unsaturated bonds.

5. The colored curable resin composition according to claim 1, further comprising a silane coupling agent.

6. The colored curable resin composition according to claim 5, wherein the silane coupling agent is a nitrogen-containing silane coupling agent.

7. A color filter which is a cured film of a colored curable resin composition according to any one of claims 1 to 6.

8. A display device including the color filter described in claim 7.

9. A step of applying a colored curable resin composition according to any one of claims 1 to 6 and pre-baking it to form a composition layer, A step of exposing the obtained composition layer through a mask, A step of developing the composition layer after exposure to form a pattern, and A step of performing a post-bake on the obtained pattern, A method for manufacturing a color filter, including, A manufacturing method wherein the post-bake temperature is 50 to 120°C.

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