Colored curable resin composition, color filter and display device

Abstract

To provide a colored curable resin composition which enables formation of a color filter that enhances at least one of such pattern formability as to form a good pattern shape even when a prebaking temperature is low and developing time is long, light resistance and solvent resistance.SOLUTION: A colored curable resin composition contains a coloring agent, a resin, a polymerizable compound and a polymerization initiator, wherein a percentage content of the coloring agent is 10 to 60 mass% in the total amount of a solid content of the colored curable resin composition, and the polymerization initiator contains a compound represented by formula (X). In the formula (X), R1, R2 and R3 each independently represents an alkyl group having 1 to 17 carbon atoms, Ar represents a divalent heterocyclic group having 4 or 5 carbon atoms, and n represents 0 or 1.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a colored curable resin composition, a color filter, and a display device. [Background technology]

[0002] Organic EL (Electro-Luminescence) display devices using OLEDs (Organic Light Emitting Diodes) and other elements do not require backlighting, and therefore can be made lighter and thinner than liquid crystal display devices and other devices. They also achieve high image quality with fast response speeds and high contrast, are energy-efficient, and are foldable, which is why they are used in a variety of fields, including mobile phones, personal digital assistants, and televisions.

[0003] Color filters used in organic EL display devices can be produced by applying a colored curable resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator to a substrate, drying the composition by heating (pre-baking) to remove volatile components such as the solvent, and then forming a desired pattern by a method such as exposing the composition through a photomask, developing, and heating (post-baking). A compound represented by the following formula (Z) is known as a polymerization initiator for the colored curable resin composition (Patent Document 1), and a colored curable resin composition containing this compound is specifically pre-baked at 100°C, then exposed to light through a photomask for curing, and developed for 60 seconds to form a color filter.

[0004] [ka] [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Publication No. 2022-153270 Summary of the Invention [Problem to be solved by the invention]

[0006] Because the heat resistance of the organic light-emitting layer used in an organic EL display device is generally low, it may be necessary to form a pattern at a lower temperature when forming a color filter for use in an organic EL display device. Furthermore, the development time may be extended to eliminate development residues. However, the colored curable resin composition described in Patent Document 1 does not use a lower pre-bake temperature or a long development time. The inventors' investigations revealed that there is a concern that lowering the pre-bake temperature or lengthening the development time may result in a deterioration in the pattern shape (for example, an inverted tapered shape). Furthermore, color filters may be required to have improved light resistance and solvent resistance. Therefore, an object of the present invention is to provide a colored curable resin composition that can form a color filter having improved pattern formability, i.e., improved light resistance and solvent resistance, and that can form a good pattern shape even when the pre-bake temperature is low or the development time is prolonged. [Means for solving the problem]

[0007] The gist of the present invention is as follows. [1] A colored curable resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, the content of the colorant is 10 to 60 mass% of the total amount of solids in the colored curable resin composition, The colored curable resin composition, wherein the polymerization initiator comprises a compound represented by formula (X): [ka] [In formula (X), R 1 , R 2 and R 3 each independently represents an alkyl group having 1 to 17 carbon atoms, Ar represents a divalent heterocyclic group having 4 or 5 carbon atoms; n represents 0 or 1. [2] The colored curable resin composition according to [1], wherein the content of the compound represented by formula (X) is 0.1 to 50 parts by mass relative to 100 parts by mass of the colorant. [3] A color filter formed from the colored curable resin composition according to [1] or [2]. [4] A display device comprising the color filter according to [3]. [Effects of the Invention]

[0008] The colored curable resin composition of the present invention can improve at least one of the following: pattern formability, i.e., a good pattern shape, even when the pre-baking temperature is low or the development time is prolonged; the light resistance of the resulting color filter; and the solvent resistance of the resulting color filter. Preferably, the colored curable resin composition of the present invention can improve the solvent resistance of the resulting color filter, more preferably the solvent resistance and light resistance of the resulting color filter, and even more preferably the pattern formability of the resulting color filter in addition to the solvent resistance and light resistance. The colored curable resin composition of the present invention is also preferable in that it can improve the pattern formability and the light resistance of the resulting color filter. [Brief explanation of the drawings]

[0009] [Figure 1] FIG. 1 is a schematic diagram illustrating the cross-sectional shape of a colored pattern. DETAILED DESCRIPTION OF THE INVENTION

[0010] <<Colored curable resin composition>> The colored curable resin composition of the present invention contains a predetermined amount of a colorant (hereinafter may be referred to as colorant (A)), a resin (hereinafter may be referred to as resin (B)), a polymerizable compound (hereinafter may be referred to as polymerizable compound (C)), and a polymerization initiator containing a compound represented by formula (X) (hereinafter may be referred to as polymerization initiator (D)). The colored curable resin composition of the present invention may further contain a solvent (hereinafter, may be referred to as solvent (E)). The colored curable resin composition of the present invention may further contain a polymerization initiation aid (hereinafter, may be referred to as polymerization initiation aid (D1)). The colored curable resin composition of the present invention may further contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, each component can be used alone or in combination unless otherwise specified.

[0011] <Colorant (A)> Examples of the colorant (A) include dyes (hereinafter sometimes referred to as dyes (A1)) and pigments (hereinafter sometimes referred to as pigments (A2)), of which pigments (A2) are preferred. These may be used alone or in combination of two or more.

[0012] The dye (A1) is not particularly limited, and known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used include azo dyes, cyanine dyes, triarylmethane dyes, xanthene dyes, thiazole dyes, oxazine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, and isoindoline dyes. Among these, azo dyes, triarylmethane dyes, xanthene dyes, and phthalocyanine dyes are preferred, with triarylmethane dyes and xanthene dyes being more preferred.

[0013] Specifically, the dyes are: CI Solvent Yellow 4 (hereinafter, the notation CI Solvent Yellow will be omitted and only the numbers will be listed. The same applies to the others.), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189; CI Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; 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, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; 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, 177, 178, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 23 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, 149, 162, 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, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; CI Acid dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; 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, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166 6, 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 Dyes, such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, 60, etc. CI Basic Red 1, 9, 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 dyes, such as CI Basic Green 1; 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 Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant 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 Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Mordant dyes, such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; Examples include CI Vat dyes such as CI Vat Green 1; These dyes (A1) may be appropriately selected according to the optical spectrum of the desired color filter.

[0014] As the pigment (A2), known pigments can be used, including those classified as pigments in the Color Index (published by The Society of Dyers and Colourists). In addition, according to chemical structure, examples include azo pigments, cyanine pigments, triphenylmethane pigments, xanthene pigments, diketopyrrolopyrrole pigments, anthraquinone pigments, dioxazine pigments, naphthoquinone pigments, quinoneimine pigments, methine pigments, azomethine pigments, squarylium pigments, acridine pigments, styryl pigments, coumarin pigments, quinoline pigments, nitro pigments, phthalocyanine pigments, perylene pigments, quinophthalone pigments, and isoindoline pigments.

[0015] Specifically, pigments classified as pigments include: 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; Red pigments such as 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; Blue pigments such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60; Purple pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 37, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, 67; Brown pigments such as CI Pigment Brown 23 and 25; Black pigments such as CI Pigment Black 1, 7, 31, and 32; These pigments (A2) may be appropriately selected according to the optical spectrum of the desired color filter.

[0016] Among these, the pigment (A2) preferably includes phthalocyanine pigments such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, and CI Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, and 67. Of the phthalocyanine pigments, at least one selected from the group consisting of CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, and CI Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, and 67 is more preferred. The content of the phthalocyanine pigment in the pigment (A2) is, for example, 20 to 100 mass%, preferably 40 to 100 mass%, more preferably 50 to 100 mass%, even more preferably 80 to 100 mass%, and particularly preferably 90 to 99 mass%.

[0017] The pigment (A2) may be optionally subjected to a rosin treatment, a surface treatment using a pigment derivative having an acidic or basic group introduced therein, a grafting treatment onto the pigment surface using a polymer compound, a particle size reduction treatment using a sulfuric acid atomization method, a washing treatment using an organic solvent or water to remove impurities, or a treatment to remove ionic impurities using an ion exchange method. The particle size of the pigment (A2) is preferably substantially uniform. The pigment (A2) can be dispersed in a solvent to form a pigment dispersion in which the pigment is uniformly dispersed. The pigments (A2) may be dispersed individually or in combination.

[0018] Examples of pigment dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of pigment dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Corporation), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark), and BYK (registered trademark) (manufactured by BYK-Chemie).

[0019] When a pigment dispersant is used, the amount used is preferably 10 to 200 parts by mass, more preferably 15 to 150 parts by mass, and even more preferably 20 to 80 parts by mass, relative to 100 parts by mass of the pigment (A2). When the amount of the pigment dispersant used is within the above range, a pigment dispersion in a more uniformly dispersed state tends to be obtained.

[0020] The colorant (A) preferably contains a pigment (A2). The content of the pigment (A2) in the colorant (A) is, for example, 20 to 100 mass %, preferably 50 to 100 mass %, and more preferably 80 to 100 mass %.

[0021] When producing a blue color filter, the colorant (A) preferably contains a blue pigment, more preferably contains a blue phthalocyanine pigment, even more preferably contains 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, and particularly preferably contains CI Pigment Blue 15:6. When producing a blue color filter, the colorant (A) preferably contains at least one selected from the group consisting of triarylmethane dyes; xanthene dyes; and violet pigments such as CI Pigment Violet 19, 23, and 37, in addition to a blue pigment.

[0022] The content of the blue pigment in the colorant (A) is, for example, 20 to 100% by mass, preferably 50 to 95% by mass, and more preferably 60 to 90% by mass.

[0023] When producing a red color filter, the colorant (A) preferably contains a red pigment, more preferably contains at least one red pigment selected from the group consisting of CI Pigment Red 242, 254, 264, 269, 272, and 291, still more preferably contains at least one red pigment selected from the group consisting of CI Pigment Red 254, 269, 272, and 291, and particularly preferably contains at least one red pigment selected from the group consisting of CI Pigment Red 254, 272, and 291. Furthermore, when producing a red color filter, the colorant (A) also preferably contains a diketopyrrolopyrrole pigment (for example, CI Pigment Red 254, 272, or 291) as the red pigment. Furthermore, when producing a red color filter, the colorant (A) preferably contains, in addition to a red pigment, at least one selected from the group consisting of xanthene dyes; azo dyes; yellow pigments such as CI Pigment Yellow 139, 150, 235, and 236; and orange pigments such as CI Pigment Orange 13. The content of the red pigment in the colorant (A) is, for example, 20 to 100% by mass, preferably 50 to 95% by mass, and more preferably 60 to 90% by mass.

[0024] When producing a green color filter, the colorant (A) preferably contains a green pigment, more preferably contains a green phthalocyanine pigment, further preferably contains at least one green pigment selected from the group consisting of CI Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, and 67, and particularly preferably contains at least one green pigment selected from the group consisting of CI Pigment Green 58, 59, 62, 63, 64, 65, 66, and 67. When preparing a green color filter, the colorant (A) preferably contains at least one selected from the group consisting of phthalocyanine dyes; azo dyes; and yellow pigments such as CI Pigment Yellow 139, 150, 235, and 236, in addition to a green pigment. The content of the green pigment in the colorant (A) is, for example, 20 to 100% by mass, preferably 50 to 95% by mass, and more preferably 60 to 90% by mass.

[0025] The content of the colorant (A) in the colored curable resin composition is 10 to 60 mass %, preferably 12 to 55 mass %, and more preferably 15 to 50 mass %, of the total amount of solids. When the content of the colorant (A) is within the above range, it becomes easier to obtain spectrum and color density suitable for a color filter. In this specification, the term "total amount of solids" refers to the total amount of components excluding the solvent from the colored curable resin composition of the present invention. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0026] <Resin (B)> Resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of resin (B) include the following resins [K1] to [K6], and it is preferably at least one selected from resins [K1] to [K6]. Resin [K1]: a copolymer having structural units derived from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]: a copolymer having structural units derived from (a), structural units derived from (b), and structural units derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, sometimes referred to as "(c)"); Resin [K3]: a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]: a copolymer having a structural unit derived from (a) to which (b) has been added and a structural unit derived from (c), and which contains a structural unit derived from (a) to which (b) has not been added; Resin [K4']: a copolymer having a structural unit derived from (a) to which (b) has been added and a structural unit derived from (c), but not containing a structural unit derived from (a) to which (b) has not been added; Resin [K5]: a copolymer having structural units derived from (b) to which (a) has been added and structural units derived from (c) (which may contain, but preferably does not contain, structural units derived from (b) to which (a) has not been added); Resin [K6]: A copolymer having a structural unit obtained by adding the (a) to a structural unit derived from the (b) and further adding a carboxylic acid anhydride, and a structural unit derived from the (c).

[0027] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution.

[0028] (b) refers to, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group. In this specification, "(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" also have the same meaning.

[0029] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").

[0030] Examples of (b1) include a monomer (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.

[0031] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0032] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (BI), and compounds represented by formula (BII).

[0033] [ka]

[0034] [In formula (BI) and formula (BII), R e and R f represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X e and X fis a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g represents -NH-. R g represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0035] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R e and R f Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0036] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. X e and X f Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).

[0037] Examples of compounds represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formula (BI-1), (BI-3), (BII-5), (BI-7), (BI-9) or (BI-11) to (BI-15) are preferred, and compounds represented by formula (BI-1), (BI-7), (BI-9) or (BI-15) are more preferred.

[0038] [ka]

[0039] Examples of the compound represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15). Among these, compounds represented by formula (BII-1), (BII-3), (BII-5), (BII-7), (BII-9) or (BII-11) to (BII-15) are preferred, and compounds represented by formula (BII-1), (BII-7), (BII-9) or (BII-15) are more preferred.

[0040] [ka]

[0041] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio thereof [compound represented by formula (BI) : compound represented by formula (BII)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20 on a molar basis.

[0042] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like.

[0043] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0044] As (b), (b1) is preferred in that it can further increase the reliability of the obtained color filter in terms of heat resistance, chemical resistance, etc. Furthermore, (b1-2) is more preferred in that it provides excellent storage stability to the colored curable resin composition.

[0045] Examples of (c) include (meth)acrylic acid ester monomers, unsaturated carboxylic acid esters such as unsaturated dicarboxylic acid esters, and vinyl monomers having an unsaturated aliphatic hydrocarbon ring, an unsaturated heterocyclic ring, or an aromatic ring. Examples of the (meth)acrylic acid ester monomer include (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group, such as methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, and stearyl (meth)acrylate; (meth)acrylic acid esters having a linear or branched aliphatic unsaturated hydrocarbon group, such as allyl (meth)acrylate and propargyl (meth)acrylate; Cyclohexyl (meth)acrylate, cyclopentyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, such as decan-8-yl (meth)acrylate (commonly known in the technical field as "dicyclopentanyl (meth)acrylate" and sometimes called "tricyclodecyl (meth)acrylate"), isobornyl (meth)acrylate, and adamantyl (meth)acrylate; Tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, such as decene-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the technical field), and dicyclopentanyloxyethyl (meth)acrylate; (meth)acrylic acid esters having an aromatic ring, such as phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate, and phenoxybenzyl (meth)acrylate; Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; and the like. Examples of the unsaturated dicarboxylic acid ester include dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate.

[0046] Among these unsaturated carboxylic acid esters, C esters such as methyl (meth)acrylate and 2-ethylhexyl (meth)acrylate are 1-10 Alkyl (meth)acrylate; Tricyclo[5.2.1.0 2,6 ] (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, such as decan-8-yl (meth)acrylate; Tricyclo[5.2.1.0 2,6 ](meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, such as decene-8-yl(meth)acrylate; Preferred are (meth)acrylic acid esters having an aromatic ring, such as benzyl (meth)acrylate and phenoxybenzyl (meth)acrylate.

[0047] Vinyl monomers having an unsaturated aliphatic hydrocarbon ring include bicyclo[2.2.1]hept-2-ene (also called 2-norbornene), 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxy ethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6- Dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1 ]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene, and other bicyclounsaturated compounds. Examples of vinyl monomers having an unsaturated heterocycle include dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide. Examples of vinyl monomers having an aromatic ring include styrene-based monomers such as styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene. Other vinyl monomers include nitrile group-containing monomers such as acrylonitrile and methacrylonitrile; Halogen atom-containing monomers such as vinyl chloride and vinylidene chloride; Examples include acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Among these vinyl monomers, from the viewpoints of copolymerization reactivity and heat resistance, styrene-based monomers such as styrene and vinyltoluene, dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide and N-benzylmaleimide, and bicyclounsaturated compounds such as bicyclo[2.2.1]hept-2-ene (also called 2-norbornene) are preferred.

[0048] The structural unit obtained by adding (b) to a structural unit derived from (a) refers to a unit formed by adding (b) to a structural unit derived from (a) that constitutes the main chain of the copolymer, and has a pendant unsaturated group derived from (b). In this structural unit, (a) may be any of the above-mentioned examples, and (b) may also be any of the above-mentioned examples. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred.

[0049] The structural unit obtained by adding (a) to a structural unit derived from (b) refers to a unit formed by adding (a) to a structural unit derived from (b) that constitutes the main chain of the copolymer, and has a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above-mentioned examples, and (a) may also be any of the above-mentioned examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred.

[0050] A structural unit obtained by adding (a) to a structural unit derived from (b) and then further adding a carboxylic acid anhydride refers to a structural unit in which (a) is added to a structural unit derived from (b) constituting the main chain of the copolymer, resulting in the formation of a hydroxyl group, to which a carboxylic acid anhydride is attached through half-esterification. This structural unit has a pendant carboxy group derived from the carboxylic acid anhydride and a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above-mentioned examples, and (a) may also be any of the above-mentioned examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. Examples of carboxylic acid anhydrides include saturated aliphatic polycarboxylic acid anhydrides such as malonic anhydride, succinic anhydride, glutaric anhydride, and adipic anhydride; unsaturated aliphatic polycarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, and itaconic anhydride; aromatic polycarboxylic acid anhydrides such as 3-vinylphthalic anhydride and 4-vinylphthalic anhydride; and alicyclic polycarboxylic acid anhydrides such as 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride.

[0051] In the resin [K1], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: It is also preferable that the structural unit derived from (c) is not substantially contained. The total of the structural units derived from (a) and the structural units derived from (b) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K1]. When the ratio of the structural units of the resin [K1] is within the above range, the colored curable resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the resulting color filter.

[0052] Resin [K1] can be produced, for example, by the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and by reference to the references described in said literature.

[0053] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, followed by heating and keeping the temperature while stirring. The polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, etc.). The solvent may be any solvent that dissolves each monomer, such as the solvent (E) described below.

[0054] The resulting copolymer may be used as a solution after the reaction as is, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. In particular, by using the solvent contained in the colored curable resin composition of the present invention as the solvent during the polymerization, the solution after the reaction can be used as is for preparing the colored curable resin composition of the present invention, thereby simplifying the production process for the colored curable resin composition of the present invention.

[0055] In the resin [K2], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 1 to 70 mol% Structural units derived from (b): 1 to 60 mol% Structural units derived from (c): 20 to 95 mol% Preferably, Structural units derived from (a): 3 to 50 mol% Structural units derived from (b): 3 to 40 mol% Structural units derived from (c): 30 to 90 mol% It is more preferable that Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 30 mol% Structural units derived from (c): 40 to 80 mol% It is even more preferable that: The total of the structural units derived from (a), the structural units derived from (b), and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K2]. When the ratio of the structural units of the resin [K2] is within the above range, the colored curable resin composition tends to have excellent storage stability, developability when forming a colored pattern, and the obtained color filter tends to have excellent solvent resistance, heat resistance, and mechanical strength.

[0056] In the resin [K2], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. (b) is preferably a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond, and more preferably a monomer (b1-2) having an epoxidized alicyclic unsaturated hydrocarbon. (c) is preferably a (meth)acrylic acid ester having a cyclic unsaturated aliphatic hydrocarbon group, a (meth)acrylic acid ester having an aromatic ring, or a dicarbonyl imide derivative.

[0057] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0058] In the resin [K3], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 70 mol% Structural units derived from (c): 30 to 98 mol% Preferably, Structural units derived from (a): 10 to 60 mol% Structural units derived from (c): 40 to 90 mol% It is more preferable that Structural units derived from (a): 35 to 60 mol% Structural units derived from (c): 40 to 65 mol% It is even more preferable that: It is also preferable that the polymer contains substantially no structural units derived from (b). The total of the structural units derived from (a) and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all structural units constituting the resin [K3].

[0059] In the resin [K3], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid, and (c) is preferably a (meth)acrylic acid ester having an aromatic ring. Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

[0060] In the resin [K4], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a) (without addition of (b)): 1 to 60 mol% Structural units in which (b) is added to structural units derived from (a): 1 to 50 mol% Structural units derived from (c): 30 to 90 mol% Preferably, Structural units derived from (a) (without addition of (b)): 5 to 50 mol% Structural units in which (b) is added to structural units derived from (a): 5 to 40 mol% Structural units derived from (c): 35 to 80 mol% It is more preferable that Structural units derived from (a) (without addition of (b)): 10 to 40 mol% Structural units in which (b) is added to structural units derived from (a): 10 to 25 mol% Structural units derived from (c): 40 to 75 mol% It is even more preferable that: The total of the structural units derived from (a) (without the addition of (b)), the structural units derived from (a) with the addition of (b), and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K4].

[0061] The structural unit derived from (a) (without the addition of (b)) is preferably a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit obtained by adding (b) to a structural unit derived from (a) is preferably a structural unit obtained by adding a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, (meth)acrylic acid esters having an aromatic ring, bicyclounsaturated compounds, and styrene-based monomers, more preferably two or more. When (c) has two or more types of structural units derived from (c), it is preferable that two or more types be selected from unsaturated carboxylic acid esters such as (meth)acrylic acid esters, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and (meth)acrylic acid esters having an aromatic ring, and it is more preferable that (c) includes (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and (meth)acrylic acid esters having an aromatic ring.

[0062] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].

[0063] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.), a polymerization inhibitor (e.g., hydroquinone, methoquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 20 hours to produce the resin [K4]. The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 55 mol, per 100 mol of (a). By using this range, the storage stability of the colored curable resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be better. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

[0064] In the resin [K4'], the ratio of the structural units derived from each of these is as follows, among all the structural units constituting the resin [K4']: Structural units in which (b) is added to structural units derived from (a): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units obtained by adding (b) to structural units derived from (a): 15 to 90 mol% Structural units derived from (c): 10 to 85 mol% It is more preferable that Structural units obtained by adding (b) to structural units derived from (a): 20 to 80 mol% Structural units derived from (c): 20 to 80 mol% It is even more preferable that: Furthermore, structural units derived from (a) to which (b) is not added are not substantially included. The total of the structural units obtained by adding (b) to the structural units derived from (a) and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K4'].

[0065] The structural unit obtained by adding (b) to a structural unit derived from (a) is preferably a structural unit obtained by adding a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, more preferably two or more selected from these. The resin [K4'] may be produced by referring to the production method of the resin [K4] described above, and the amount of (b) used is preferably 100 mol per 100 mol of (a).

[0066] In resin [K5], the ratio of structural units derived from each of these is as follows among all structural units constituting resin [K5]: Structural units derived from (b) (without (a) added): 0 to 30 mol% Structural units in which (a) is added to structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units derived from (b) (without (a) added): 0 to 10 mol% Structural units obtained by adding (a) to structural units derived from (b): 15 to 90 mol% Structural units derived from (c): 10 to 85 mol% It is more preferable that Structural units derived from (b) (without (a) added): 0 to 5 mol% Structural units in which (a) is added to structural units derived from (b): 20 to 80 mol% Structural units derived from (c): 20 to 80 mol% It is even more preferable that: The total of the structural units derived from (b) (without (a) added), the structural units derived from (b) with (a) added, and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K5].

[0067] The structural unit derived from (b) (without (a) added) is preferably a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized. The structural unit in which (a) has been added to a structural unit derived from (b) is preferably a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid has been added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, more preferably two or more selected from these.

[0068] Resin [K5] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0069] Furthermore, under the same conditions as in the production method of resin [K4] or resin [K4'], resin [K5] can be obtained by reacting a cyclic ether derived from (b) contained in a copolymer of (b) and (c) with a carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used to react with the copolymer is preferably 5 to 100 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.

[0070] In the resin [K6], the ratio of structural units derived from each of these is as follows: Structural units derived from (b) (without (a) added): 0 to 30 mol% Structural units in which (a) is added to structural units derived from (b) (no carboxylic acid anhydride is added); 20 to 85 mol% Structural units obtained by adding (a) to structural units derived from (b) and then adding a carboxylic acid anhydride thereto: 2 to 40 mol% Structural units derived from (c): 10 to 60 mol% Preferably, Structural units derived from (b) (without (a) added): 0 to 10 mol% Structural units in which (a) is added to structural units derived from (b) (no carboxylic acid anhydride is added); 40 to 80 mol% a structural unit obtained by adding (a) to a structural unit derived from (b) and then adding a carboxylic acid anhydride thereto; 3 to 30 mol% Structural units derived from (c): 15 to 50 mol% It is more preferable that Structural units derived from (b) (without (a) added): 0 to 5 mol% Structural units in which (a) is added to structural units derived from (b) (no carboxylic acid anhydride is added); 50 to 70 mol% Structural units obtained by adding (a) to structural units derived from (b) and then adding a carboxylic acid anhydride thereto: 5 to 20 mol% Structural units derived from (c): 20 to 40 mol% It is even more preferable that:

[0071] The total of the structural units derived from (b) (to which (a) is not added), the structural units in which (a) is added to the structural units derived from (b) (to which carboxylic acid anhydride is not added), the structural units in which (a) is added to the structural units derived from (b) and then a carboxylic acid anhydride is added, and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K6].

[0072] As the structural unit derived from (b) (without (a) added), a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched-chain aliphatic unsaturated hydrocarbon has been epoxidized is preferred. As the structural unit in which (a) has been added to a structural unit derived from (b) (without carboxylic acid anhydride added), a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid has been added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched-chain aliphatic unsaturated hydrocarbon has been epoxidized is preferred. As the structural unit in which (a) has been added to a structural unit derived from (b) and a carboxylic acid anhydride has been further added, a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid has been added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched-chain aliphatic unsaturated hydrocarbon has been epoxidized is preferred, The structural unit derived from (c) is preferably one or more types selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and more preferably two or more types.

[0073] Resin [K6] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0074] Furthermore, under the same conditions as in the production of resin [K4], the cyclic ether derived from (b) contained in the copolymer of (b) and (c) is reacted with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used is preferably 80 to 100 moles per 100 moles of (b).

[0075] The hydroxyl group generated by the reaction of the cyclic ether with the carboxylic acid or carboxylic acid anhydride contained in (a) is reacted with the carboxylic acid anhydride. The amount of the carboxylic acid anhydride used is preferably 0.05 to 1 mol, more preferably 0.10 to 0.8 mol, and even more preferably 0.13 to 0.7 mol, per 1 mol of the amount of (a) used (in other words, per 1 mol of the hydroxyl group generated by the use of (a)).

[0076] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid copolymer and other resins [K1]; Glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / tricyclo[5.2.1.0 2,6 ]decene-8-yl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / benzyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / phenoxybenzyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, and other resins [K2]; Resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; Resins such as a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a benzyl (meth)acrylate / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a benzyl (meth)acrylate / dicyclopentanyl (meth)acrylate / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a norbornene / vinyltoluene / (meth)acrylic acid copolymer, and a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a norbornene / styrene / (meth)acrylic acid copolymer [K4]; Resins such as a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / (meth)acrylic acid with glycidyl (meth)acrylate, and a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid with glycidyl (meth)acrylate [K4']; Resins such as resins obtained by reacting tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymers with (meth)acrylic acid, and resins obtained by reacting tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate copolymers with (meth)acrylic acid [K5]; Examples of such resins include a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate with (meth)acrylic acid and then reacting the resulting resin with tetrahydrophthalic anhydride, a resin obtained by reacting a copolymer of 2-ethylhexyl (meth)acrylate, tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate with (meth)acrylic acid and then reacting the resulting resin with succinic anhydride, and a resin obtained by reacting a copolymer of methyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate with (meth)acrylic acid and then reacting the resulting resin with succinic anhydride [K6].

[0077] The resin (B) is preferably at least one selected from the group consisting of the resin [K1], the resin [K2], and the resin [K4], and is more preferably the resin [K4].

[0078] The polystyrene-equivalent weight average molecular weight of resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed areas in the developer is good, and the resolution of the colored pattern tends to be improved. The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

[0079] The acid value of the resin (B) is preferably 20 to 170 mg-KOH / g, more preferably 25 to 150 mg-KOH / g, and even more preferably 30 to 135 mg-KOH / g, calculated as solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0080] The content of resin (B) is preferably 2 to 70 mass %, more preferably 10 to 65 mass %, and even more preferably 30 to 60 mass %, of the total amount of solids in the colored curable resin composition. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[0081] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

[0082] Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 2-ethylhexylcarbitol (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N-vinylpyrrolidone, and the above-mentioned monomers (a), (b) and (c).

[0083] Examples of polymerizable compounds having two ethylenically unsaturated bonds include glycerin di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

[0084] The polymerizable compound (C) is particularly preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylate (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylate (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylate, ... ) acrylates (e.g., tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylates (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl)isocyanurate, alkoxylated pentaerythritol poly(meth)acrylates (e.g., ethoxylated pentaerythritol tri(meth)acrylate), Acrylates, ethoxylated pentaerythritol tetra(meth)acrylate, propoxylated pentaerythritol tri(meth)acrylate, propoxylated pentaerythritol tetra(meth)acrylate), alkoxylated dipentaerythritol poly(meth)acrylates (e.g., ethoxylated dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol penta(meth)acrylate, propoxylated dipentaerythritol caprolactone-modified pentaerythritol poly(meth)acrylates (e.g., caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylates (e.g., caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate), and the like. Among these, it is preferable to include at least one selected from the group consisting of glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, and dipentaerythritol poly(meth)acrylate, and it is more preferable to include at least one selected from the group consisting of glycerin triacrylate, trimethylolpropane triacrylate, and dipentaerythritol polyacrylate.

[0085] The weight average molecular weight of the polymerizable compound (C) is preferably 50 to 4,000, more preferably 70 to 3,500, even more preferably 100 to 3,000, still more preferably 150 to 2,900, and particularly preferably 250 to 1,500.

[0086] The content of the polymerizable compound (C) is, for example, 1 to 80 mass %, preferably 5 to 50 mass %, and more preferably 10 to 30 mass %, of the total amount of solids in the colored curable resin composition.

[0087] <Polymerization initiator (D)> The polymerization initiator (D) contains a compound represented by formula (X) (hereinafter, sometimes referred to as compound (X)). During the production of a color filter, residues of the polymerization initiator that have released active species such as active radicals or acids, or unreacted polymerization initiator, may remain in the film. If the residues of the polymerization initiator are unstable to light, they may discolor and cause a color change in the color filter after light irradiation. Perhaps because residues of compound (X) are not easily discolored by light irradiation, the present invention can suppress color change in the color filter after light irradiation, and the resulting color filter is thought to have excellent light resistance. Furthermore, by including compound (X) in the colored curable resin composition, a good pattern shape can be formed even if the pre-bake temperature is lowered or the development time is extended (i.e., regardless of the color filter production conditions). Furthermore, by including compound (X) in the colored curable resin composition, the solvent resistance of the resulting color filter can be improved.

[0088] [ka] [In formula (X), R 1 , R 2 and R 3 each independently represents an alkyl group having 1 to 17 carbon atoms, Ar represents a divalent heterocyclic group having 4 or 5 carbon atoms; n represents 0 or 1.

[0089] R 1 , R 2 and R 3 Examples of the alkyl group represented by the formula: straight-chain alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, and n-heptadecyl groups; Isopropyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1,1-dimethylpropyl, 1,1,2-trimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, 2-propylpentyl, 1-ethyl-1,2-dimethylpropyl, 1-methylpentyl, 4-methylpentyl branched alkyl groups such as 4-methylhexyl, 5-methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl, and 1-butylhexyl groups;

[0090] In formula (X), two R 1may be the same or different, but are preferably the same, and two R 2 may be the same or different, but are preferably the same, and two R 3 may be the same or different, but are preferably the same.

[0091] R 1 is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 2 to 8 carbon atoms, even more preferably an alkyl group having 2 to 4 carbon atoms, and particularly preferably an ethyl group.

[0092] R 2 is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, even more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group.

[0093] R 3 is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group.

[0094] The divalent heterocyclic group having 4 or 5 carbon atoms represented by Ar is a heterocyclic group having 4 or 5 carbon atoms in which two hydrogen atoms directly bonded to atoms constituting the ring are replaced with bonds.

[0095] The heterocycle constituting the divalent heterocyclic group may be either an aromatic heterocycle (i.e., an aromatic heterocycle) or a non-aromatic heterocycle (i.e., a non-aromatic heterocycle), but is preferably an aromatic heterocycle. Specific examples of the heterocycle constituting the divalent heterocyclic group include five-membered aromatic heterocycles such as a furan ring, a pyrrole ring, a thiophene ring, a 1,2,3-triazole ring, an imidazole ring, a pyrazole ring, a thiazole ring, and an oxazole ring; and six-membered aromatic heterocycles such as a pyrazine ring, a pyrimidine ring, a pyridazine ring, and a 1,3,5-triazine ring.

[0096] In formula (X), the two Ar may be the same or different, but are preferably the same.

[0097] The Ar is preferably a group in which two hydrogen atoms directly bonded to atoms constituting a carbon atom in an aromatic heterocycle having 4 or 5 carbon atoms are replaced with hand bonds, more preferably a group in which two hydrogen atoms directly bonded to atoms constituting a 5-membered aromatic heterocycle are replaced with hand bonds, still more preferably a group in which two hydrogen atoms directly bonded to atoms constituting a furan ring or a thiophene ring are replaced with hand bonds, and particularly preferably a group in which two hydrogen atoms directly bonded to atoms constituting a thiophene ring are replaced with hand bonds.

[0098] n represents 0 or 1, and is preferably 0. In formula (X), the two n's may be the same or different, but are preferably the same.

[0099] Specific examples of the compound (X) include compounds (X-1) to (X-48) shown in Table 1.

[0100] [Table 1]

[0101] In Table 1, ar-1 represents a group represented by the following formula (ar-1), and ar-2 represents a group represented by the following formula (ar-2): In the following formulas, * represents a bond.

[0102] [ka]

[0103] The content of compound (X) in polymerization initiator (D) is, for example, 10 to 100% by mass, and preferably 20 to 100% by mass. The lower limit of the content may be 30% by mass or more, 50% by mass or more, or 80% by mass or more. From the viewpoint of achieving particularly excellent light resistance of the resulting color filter, the content of compound (X) in polymerization initiator (D) is preferably 10 to 100% by mass, more preferably 20 to 60% by mass, and even more preferably 20 to 40% by mass.

[0104] The content of the compound (X) is preferably 0.1 to 50 parts by mass, more preferably 1 to 40 parts by mass, even more preferably 1 to 35 parts by mass, and particularly preferably 3 to 25 parts by mass, relative to 100 parts by mass of the colorant (A).

[0105] The content of the compound (X) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and even more preferably 2 to 10 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C).

[0106] The polymerization initiator (D) may contain a polymerization initiator other than the compound (X) (hereinafter, sometimes referred to as "other polymerization initiators") as long as the other polymerization initiator is a compound other than the compound (X) that generates active radicals, acids, etc. by the action of light or heat and can initiate polymerization.

[0107] Other examples of the polymerization initiator include O-acyloxime compounds other than the compound (X), alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0108] The O-acyloxime compound is a compound having a partial structure represented by formula (d-1): In the formula, * represents a bond.

[0109] [ka]

[0110] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl)-2-methylbenzoyl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl) ...

[0033] N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and the like. Commercially available products such as Irgacure (registered trademark) OXE01, OXE02, and OXE03 (all manufactured by BASF), Adeka Arcles (registered trademark) N-1919, NCI-730, NCI-831, and NCI-930 (all manufactured by ADEKA), and TR-PBG327 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used.

[0111] The alkylphenone compound is a compound having a partial structure represented by formula (d-2) or a partial structure represented by formula (d-3). In these partial structures, the benzene ring may have a substituent. In the formula, * represents a bond.

[0112] [ka]

[0113] Examples of compounds having a partial structure represented by formula (d-2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure (registered trademark) 369, 907, and 379 (all manufactured by BASF) may also be used.

[0114] Examples of compounds having a partial structure represented by formula (d-3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d-2).

[0115] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0116] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

[0117] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, ... Examples of suitable biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B No. 48-38403 and JP-A No. 62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A No. 7-10913). Among these, compounds represented by the following formula and mixtures thereof are preferred:

[0118] [ka]

[0119] Further examples of other polymerization initiators include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) described below (especially an amine compound).

[0120] Other examples of the polymerization initiator include polymerization initiators that generate acid, such as onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl tosylates; and benzoin tosylates.

[0121] The other polymerization initiator is preferably at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds, more preferably O-acyloxime compounds and / or biimidazole compounds, and even more preferably O-acyloxime compounds.

[0122] When other polymerization initiators are used, the content thereof is preferably 10 to 500 parts by mass, more preferably 20 to 400 parts by mass, and even more preferably 50 to 250 parts by mass, relative to 100 parts by mass of compound (X).

[0123] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and even more preferably 2 to 10 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving productivity of the color filter.

[0124] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound used to promote the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D), or is a sensitizer.

[0125] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0126] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, and preferably 4,4'-bis(diethylamino)benzophenone. Alternatively, commercially available amine compounds such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

[0127] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0128] Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0129] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0130] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and even more preferably 2 to 10 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored curable resin composition.

[0131] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the relevant field can be used. Examples of the solvent (E) include ester solvents (solvents containing -COO- in the molecule but not -O-), ether solvents (solvents containing -O- in the molecule but not -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule but not -COO-), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, or -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. Two or more of these solvents may be used in combination.

[0132] Examples of the ester solvent 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.

[0133] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

[0134] 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, and 2-ethoxy-2-methylpropionate. 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.

[0135] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0136] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0137] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0138] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0139] Among the above solvents, from the viewpoints of coatability and drying property, preferred are organic solvents having a boiling point at 1 atm of 120° C. or higher and 180° C. or lower. The organic solvent is preferably at least one selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide, and more preferably at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate, and ethyl 3-ethoxypropionate.

[0140] When the colored curable resin composition contains a solvent (E), the content of the solvent (E) is typically 99.99% by mass or less, preferably 40 to 99% by mass, more preferably 50 to 97% by mass, even more preferably 70 to 96% by mass, and even more preferably 73 to 95% by mass, based on the total amount of the colored curable resin composition. In other words, the total amount of solids in the colored curable resin composition is typically 0.01% by mass or more, preferably 1 to 60% by mass, more preferably 3 to 50% by mass, even more preferably 4 to 30% by mass, and even more preferably 5 to 27% by mass. When the content of the solvent (E) is within the above range, the flatness during application is good, and when a color filter is formed, the color density is not insufficient, which tends to result in good display characteristics.

[0141] <Leveling Agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms, which may have a polymerizable group in the side chain.

[0142] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule, including polyether-modified silicone oils. Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade names: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0143] Examples of fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule, such as Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by AGC Corporation), and E5844 (manufactured by Daikin Fine Chemical Research Institute, Ltd.).

[0144] Examples of silicone surfactants having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0145] When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005 to 1 mass%, more preferably 0.001 to 0.5 mass%, and even more preferably 0.005 to 0.1 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 (F) is within the above range, the flatness of the color filter can be improved.

[0146] <Other ingredients> The colored curable resin composition of the present invention may contain additives known in the technical field, such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, and chain transfer agents, as necessary.

[0147] <Method for producing colored curable resin composition> The colored curable resin composition of the present invention can be prepared by mixing the colorant (A), resin (B), polymerizable compound (C), polymerization initiator (D), and optionally the polymerization initiator aid (D1), solvent (E), leveling agent (F), and other components. Mixing can be carried out using known or conventional equipment and conditions. When using the pigment (A2) as the colorant (A), the pigment (A2) may be mixed with part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size becomes approximately 0.2 μm or less, to prepare a pigment dispersion. It is preferable to use the pigment dispersion. In this case, the pigment dispersant and part or all of the resin (B) may be blended as needed. The remaining components are mixed with the pigment dispersion thus obtained to obtain a predetermined concentration, thereby preparing the desired colored curable resin composition. When a dye is contained as the colorant (A), the dye may be dissolved in advance in part or all of the solvent (E) to prepare a solution, which may then be used to prepare the colored curable resin composition. The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

[0148] <Color filter> Methods for producing a colored pattern of a color filter from the colored curable resin composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography is a method in which the colored curable resin composition is applied to a substrate, dried to form a composition layer, and then exposed to light through a photomask and developed. In the photolithography, a colored coating film, which is a cured product of the composition layer, can be formed by not using a photomask during exposure and / or not developing.

[0149] The film thickness of the color filter (cured film) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, even more preferably 3 μm or less, and may be 1.5 μm or less or 0.5 μm or less, and is preferably 0.1 μm or more, more preferably 0.2 μm or more, even more preferably 0.3 μm or more.

[0150] Examples of substrates that can be used include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and silica-coated soda lime glass; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and substrates having aluminum, silver, or silver / copper / palladium alloy thin films formed thereon. These substrates may also have other color filter layers, resin layers, transistors, circuits, etc. formed thereon. Alternatively, a silicon substrate that has been subjected to HMDS treatment may also be used.

[0151] Formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be produced as follows. First, a colored curable resin composition is applied to a substrate, and then the composition is dried by heating and drying (pre-baking) and / or drying under reduced pressure to remove volatile components such as solvents, thereby obtaining a smooth composition layer. Examples of the coating method include spin coating, slit coating, and slit and spin coating.

[0152] The temperature for heat drying (pre-baking temperature) is preferably 30 to 120°C, more preferably 50 to 110°C. When pattern formation is performed at a low temperature, the pre-baking temperature also tends to be low. If the pre-baking temperature is low (for example, 30 to 90°C), solvent is likely to remain in the composition layer, and in the development described below, not only the unexposed areas but also the bottom of the exposed areas are likely to dissolve, which may result in poor pattern shape or peeling. However, with the colored curable resin composition of the present invention, even if the pre-baking temperature is lower than the temperature required in the production of organic EL display devices and the like (for example, 30 to 90°C, preferably 50 to 90°C), a colored pattern having a good shape can be formed, which is preferable. The heating time (pre-baking time) is preferably from 10 seconds to 60 minutes, and more preferably from 30 seconds to 30 minutes.

[0153] When drying is carried out under reduced pressure, it is preferable to carry out the drying under a pressure of 50 to 150 Pa at a temperature of 20 to 25°C.

[0154] The thickness of the composition layer is not particularly limited and may be appropriately selected depending on the desired thickness of the color filter.

[0155] Next, the composition layer is exposed through a photomask to form a desired color pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended application is used. The light source used for exposure is preferably a light source that emits light with a wavelength of 250 to 450 nm. For example, light less than 250 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, or 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. It is preferable to use a reduction projection exposure device or proximity exposure device such as a mask aligner or stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light and allows for accurate alignment of the photomask and substrate.

[0156] A colored pattern is formed on the substrate by contacting the exposed composition layer with a developer and developing it. The unexposed portions of the composition layer are dissolved and removed by the development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The developer may also contain a surfactant. The development method may be any of a puddle method, a dipping method, and a spray method. Furthermore, the substrate may be tilted at any angle during development. The development time is not particularly limited, but is preferably 10 seconds to 10 minutes, more preferably 20 seconds to 5 minutes, even more preferably 30 seconds to 2 minutes, and particularly preferably 70 seconds to 2 minutes. After development, it is preferable to wash with water.

[0157] Furthermore, it is preferable to post-bake the obtained colored pattern. The post-bake temperature may be 200°C or lower, but is preferably 170°C or lower, and more preferably 150°C or lower. When forming a color filter to be used in an organic EL display device, it is preferable to perform post-bake at a lower temperature (for example, 130°C or lower, preferably 100°C or lower, and more preferably 90°C or lower). The lower limit of the post-bake temperature is preferably 30°C or higher, and more preferably 50°C or higher. The post-bake time is preferably 1 to 120 minutes, and more preferably 5 to 60 minutes.

[0158] The colored pattern and colored coating film thus obtained are useful as color filters, and the color filters are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc. [Example]

[0159] 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, % and parts representing the content or amount used are by mass unless otherwise specified.

[0160] <Pigment Dispersion Liquid Preparation Example 1: Preparation of Pigment Dispersion Liquid (A-1)> 14.1 parts of CI Pigment Blue 15:6, 0.5 parts of CI Pigment Violet 23, 4.0 parts of an acrylic pigment dispersant, and 81 parts of propylene glycol monomethyl ether acetate were mixed, and the pigment was thoroughly dispersed using a bead mill to obtain a pigment dispersion (A-1).

[0161] <Pigment Dispersion Liquid Preparation Example 2: Preparation of Pigment Dispersion Liquid (A-2)> 7.2 parts of CI Pigment Green 36, 0.8 parts of CI Pigment Yellow 139, 7.0 parts of CI Pigment Yellow 150, 4.0 parts of an acrylic pigment dispersant, and 81 parts of propylene glycol monomethyl ether acetate were mixed, and the pigment was thoroughly dispersed using a bead mill to obtain a pigment dispersion (A-2).

[0162] <Pigment Dispersion Liquid Preparation Example 3: Preparation of Pigment Dispersion Liquid (A-3)> 7.8 parts of CI Pigment Red 291, 6.2 parts of CI Pigment Red 269, 1.1 parts of CI Pigment Yellow 139, 4.0 parts of an acrylic pigment dispersant, and 81 parts of propylene glycol monomethyl ether acetate were mixed, and the pigment was thoroughly dispersed using a bead mill to obtain a pigment dispersion (A-3).

[0163] <Resin Synthesis Example 1: Preparation of Resin (B-1)> Into a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 349 parts of propylene glycol monomethyl ether acetate was added, and the mixture was stirred while replacing the atmosphere with nitrogen and heated to 120°C. Next, a monomer mixture consisting of 169.2 parts of benzyl methacrylate, 103.3 parts of methacrylic acid, and 52.9 parts of dicyclopentanyl methacrylate, to which 23.4 parts of t-butylperoxy-2-ethylhexanoate had been added, was added dropwise from the dropping funnel to the flask over 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes to carry out the copolymerization reaction. The flask was then 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 a polymer (resin (B-1)). Finally, propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a polymer solids concentration of 40%, thereby obtaining a resin solution. The weight-average molecular weight of the resin (B-1) contained in the resin solution was 10,300, and the acid value per solid of the resin (B-1) was 120.9 mg-KOH / g.

[0164] The polystyrene-equivalent weight average molecular weight (Mw) of the resin was measured by GPC under the following conditions. Apparatus: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: tetrahydrofuran Flow rate: 1.0mL / min Solid concentration of the analytical sample: 0.001 to 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)

[0165] <Examples 1 to 7 and Comparative Examples 1 and 2> (1) Preparation of Colored Curable Resin Composition A colored curable resin composition was obtained by mixing a pigment dispersion, a resin solution, a polymerizable compound, a polymerization initiator, a leveling agent, and a solvent so as to obtain the composition shown in Table 2. The solvent was mixed so that the solid content of the colored curable resin composition would be 18%. The amount of each component in Table 2 is expressed in parts.

[0166] [Table 2]

[0167] In Table 2, the components are as follows: Colorant (A-1): CI Pigment Blue 15:6 and CI Pigment Violet 23 Colorant (A-2): CI Pigment Green 36, CI Pigment Yellow 139 and CI Pigment Yellow 150 Colorant (A-3): CI Pigment Red 291, CI Pigment Red 269, and CI Pigment Yellow 139 Resin (B-1): Resin (B-1) (solid content conversion) Polymerizable compound (C-1): glycerin triacrylate (Aronix (registered trademark) M-930; manufactured by Toagosei Co., Ltd.) Polymerization initiator (D-1): a compound represented by the following formula (X-1): [ka] Polymerization initiator (D-2): ADEKA ARCLES (registered trademark) NCI-831E (manufactured by ADEKA Corporation), a compound represented by the following formula (Z): [ka] Polymerization initiator (D-3): ADEKA ARCLES (registered trademark) NCI-730 (manufactured by ADEKA Corporation) Leveling agent (F-1): Polyether-modified silicone oil (manufactured by Toray Dow Corning Co., Ltd. under the trade name "Toray Silicone SH8400") Solvent (E-1): Propylene glycol monomethyl ether acetate

[0168] (2) Preparation of colored patterns (color filters) A colored curable resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated) so that the film thickness after post-baking would be 3.0 μm, and then pre-baked at 85° C. for 2 minutes to form a colored composition layer. After cooling, the substrate on which the colored composition layer was formed was spaced apart from a quartz glass photomask at a distance of 50 μm, and the layer was exposed to light at 100 mJ / cm 2 in the air using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). 2 The photoresist was irradiated with light at an exposure dose of 1000 nm (based on 365 nm). A photomask with a 30 μm line and space pattern was used. The colored composition layer after light irradiation was immersed and developed in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23° C. for 80 seconds, washed with water, and post-baked at 85° C. for 60 minutes to obtain a colored pattern.

[0169] (3) Film thickness measurement The film thickness of the resulting colored pattern was measured using a film thickness measuring device (DEKTAK3, manufactured by Nippon Shinku Gijutsu Co., Ltd.).

[0170] (4) Chromaticity evaluation The resulting colored pattern was subjected to spectral measurement using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) and stimulus value Y in the CIE XYZ color system were measured using the characteristic function of Illuminant C. In addition, the xy chromaticity coordinates (x, y) and stimulus value Y were also measured using the same procedure for the colored pattern after irradiation with xenon lamp light in the lightfastness evaluation described below.

[0171] (5) Pattern shape evaluation The shape of the obtained colored pattern was observed using a scanning electron microscope (S-4000; manufactured by Hitachi High-Technologies Corporation). The shape shown in (p1) of Figure 1 (a so-called forward tapered shape) was marked with a ◎, the shape shown in (p2) was marked with a ○, and the shape shown in (p3) (a so-called reverse tapered shape) was marked with an ×. The shapes shown in (p1) and (p2) tend to further enhance the adhesion of the colored pattern to the substrate. In particular, the shape shown in (p1) further enhances the adhesion of the colored pattern to the substrate, and when a film is laminated on the colored pattern, the film tends to be less likely to crack or peel. The results are shown in Table 3.

[0172] (6) Lightfastness evaluation An ultraviolet-cutting filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co., Ltd.; cuts light below 380 nm) was placed on the obtained colored pattern, and the pattern was irradiated with xenon lamp light for 48 hours using a light resistance tester (Suntest CPS+; manufactured by Toyo Seiki Co., Ltd.). Before and after irradiation, the xy chromaticity coordinates (x, y) and Y are measured using the method described in "(4) Chromaticity evaluation," and the color difference ΔE is calculated from the measured values ​​using the method described in JIS Z 8730:2009 (7. Calculation method for color difference). * ab was calculated and the results are shown in Table 3. △E * The smaller ab is, the smaller the color change is, i.e., △E * The smaller the ab, the better the light resistance. * If ab is 3 or less, it can be said that there is no practical problem as a color filter, but if △E * The smaller the value of ab, the more preferable.

[0173] (7) Solvent resistance evaluation The resulting colored pattern was immersed in propylene glycol monomethyl ether acetate at room temperature for 10 minutes and then thoroughly washed with water. The film thickness was measured before and after immersion using the method described in "(3) Film Thickness Measurement," and the change in film thickness before and after immersion was calculated as ΔFT (the film thickness before immersion was taken as 100%), and the results are shown in Table 3. The smaller the absolute value of ΔFT, the smaller the change in film thickness; if ΔFT is ±3% or less, the colored pattern can be said to be practically satisfactory as a color filter.

[0174] [Table 3]

[0175] The blue colored pattern obtained in Comparative Example 1 (a composition similar to that of Patent Document 1) had a poor shape and was insufficient in light fastness and solvent resistance. In contrast, the blue colored patterns obtained in Examples 1 to 5 had a good shape and exhibited high light fastness and high solvent resistance. Furthermore, compared with the green colored pattern obtained in Comparative Example 2, the green colored pattern obtained in Example 6 had a good shape and enhanced light fastness and solvent resistance. Furthermore, the red colored pattern obtained in Example 7 also had a good pattern shape and exhibited high light fastness and high solvent resistance.

Claims

1. A colored curable resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, the content of the colorant is 10 to 60 mass% of the total amount of solids in the colored curable resin composition, The colored curable resin composition, wherein the polymerization initiator comprises a compound represented by formula (X): 【Chemical 1】 [In formula (X), R 1 , R 2 and R 3 each independently represents an alkyl group having 1 to 17 carbon atoms, Ar represents a divalent heterocyclic group having 4 or 5 carbon atoms; n represents 0 or 1.

2. 2. The colored curable resin composition according to claim 1, wherein the content of the compound represented by formula (X) is 0.1 to 50 parts by mass relative to 100 parts by mass of the colorant.

3. A color filter formed from the colored curable resin composition according to claim 1 or 2.

4. A display device comprising the color filter according to claim 3 .

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