Coloring resin composition

Abstract

To provide a coloring resin composition which allows for providing a color filter that meets requirements of high color reproducibility and thinness and has a reduced dielectric loss tangent.SOLUTION: A coloring resin composition comprising at least a colorant and a resin is provided. The coloring resin composition contains a cyclic ether structure-containing component. The colorant comprises at least a green colorant. A total colorant content is 45.5 mass% or more with respect to the solid content of the coloring resin composition.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This invention relates to a colored resin composition containing a cyclic ether structure component and a green coloring agent. [Background technology]

[0002] In recent years, development of display devices has progressed to expand the color gamut they can display, and as part of this, there is a demand for color filters with darker colors. One way to meet this demand is to increase the density of the colorant in the color filter, but this is undesirable because it degrades the performance of the color filter formed from the colored resin composition, such as by worsening electrical properties (e.g., dielectric loss tangent). Furthermore, in order to achieve the desired color characteristics, it is necessary to manufacture the color filter as a thick film, but when applied to liquid crystal display devices, thick films are also undesirable because they cause mixing of light with adjacent pixels.

[0003] In particular, green colorants are known to cause deterioration of electrical properties (e.g., dielectric loss tangent) and consequently display defects in display devices (e.g., screen flicker). Therefore, it is desirable to improve the electrical properties and display defects in a green photosensitive resin composition (Patent Document 1) containing a green colorant, resin, polymerizable compound, polymerization initiator, and solvent. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2016-191747 [Overview of the project] [Problems that the invention aims to solve]

[0005] Therefore, the present invention aims to provide a colored resin composition and the like that can provide a color filter that satisfies the conditions of high color reproducibility and thin film, and has a reduced dielectric loss tangent. [Means for solving the problem]

[0006] In other words, the colored resin composition, color filter, display device, and solid-state image sensor according to the present invention have the following characteristics. [1] A colored resin composition comprising at least a coloring agent and a resin, wherein the colored resin composition comprises a cyclic ether structure-containing component, the coloring agent comprises at least a green coloring agent, and the total coloring agent content is 45.5% by mass or more relative to the solid content of the colored resin composition. [2] The colored resin composition according to [1], wherein the resin comprises a resin having a solid content acid value of 85 mg-KOH / g or more. [3] The colored resin composition according to [1] or [2], wherein the content of the green coloring agent is 5% by mass or more and 60% by mass or less with respect to the solid content of the colored resin composition. [4] The colored resin composition according to any one of [1] to [3], wherein the green coloring agent is zinc phthalocyanine. [5] The colored resin composition according to any one of [1] to [4], wherein the green coloring agent comprises at least one of CI Pigment Green 58 and CI Pigment Green 59. [6] The colored resin composition according to any one of [1] to [5], wherein the coloring agent further comprises a yellow coloring agent. [7] The colored resin composition according to any one of [1] to [6], wherein the content of the cyclic ether structure-containing component is 0.1% by mass or more and 40% by mass or less with respect to the solid content of the colored resin composition. [8] A colored coating film is formed from the colored resin composition such that the film thickness after post-baking at 230°C for 30 minutes is 1 to 4 μm, and this is measured in 2.8 × 10 5 A colored resin composition according to any one of [1] to [7], wherein the dielectric loss tangent tanδ at a frequency of 20 Hz when illuminated with an illuminance of lux (lx) is 0.20 or less. A color filter formed from any of the colored resin compositions described in [9][1] to [8]. A display device including the color filter described in

[10] [9]. A solid-state image sensor including the color filter described in

[11] [9]. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a colored resin composition that yields a color filter having reduced dielectric loss tangent while satisfying the conditions for high color reproducibility and thin film. [Modes for carrying out the invention]

[0008] The colored resin composition of the present invention comprises a coloring agent (hereinafter sometimes referred to as coloring agent (A)) and a resin (hereinafter sometimes referred to as resin (B)). The colored resin composition of the present invention may contain a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)), a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)), a solvent (hereinafter sometimes referred to as solvent (E)), and a polymerization initiator aid (hereinafter sometimes referred to as polymerization initiator aid (D1)). The colored resin composition of the present invention may contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)).

[0009] The colored resin composition according to the present invention is characterized in that the colored resin composition contains a cyclic ether structure-containing component, the colorant contains at least a green colorant, and the total colorant content is 45.5% by mass or more relative to the solid content of the colored resin composition.

[0010] The colored resin composition contains a cyclic ether structure-containing component. The cyclic ether structure-containing component may be a resin (polymer) containing a cyclic ether structure, or a compound containing a cyclic ether structure. The cyclic ether structure-containing component preferably has a cyclic ether structure with 2 to 4 carbon atoms (for example, an oxirane ring (epoxy ring), an oxetane ring, and a tetrahydrofuran ring (oxolane ring)), and more preferably has an oxirane ring or an oxetane ring. Examples of cyclic ether structure-containing components include resins having cyclic ether structures and compounds that can undergo ring-opening polymerization (sometimes referred to as compounds having a cyclic ether structure) as described in resin (B) and polymerizable compound (C) below. In this specification, a resin having a cyclic ether structure means one that has repeating structural units in its molecule and has a weight-average molecular weight of 3000 or more. A compound that can undergo ring-opening polymerization means a compound other than a resin having a cyclic ether structure, and includes monomers and oligomers. Unless otherwise specified, the compounds exemplified as components in this specification may be used individually or in combination.

[0011] In the present invention, the content of the cyclic ether structure-containing component (either or both of the resin containing the cyclic ether structure and the compound containing the cyclic ether structure) is preferably 0.1% to 50% by mass per 100% by mass of the solid content of the colored resin composition, more preferably 0.1% to 40% by mass, even more preferably 0.5% to 38% by mass, and even more preferably 1% to 35% by mass, from the viewpoint of reduced dielectric loss tangent and coating film processability.

[0012] <Coloring agent (A)> The colored resin composition according to the present invention comprises a colorant (A), the colorant (A) comprising at least a green colorant. The green colorant may be either a pigment or a dye, but is preferably a pigment, more preferably zinc phthalocyanine, even more preferably polyhalogenated zinc phthalocyanine, even more preferably polychlorinated zinc phthalocyanine or polybrominated zinc phthalocyanine, and is particularly preferably comprising at least one of CI Pigment Green 58 and CI Pigment Green 59. In the present invention, green can be defined in the XYZ color system as 0≦x≦0.40, 0.40≦y≦0.85 (preferably 0≦x≦0.30, 0.50≦y≦0.85, more preferably 0≦x≦0.20, 0.55≦y≦0.70).

[0013] The green coloring agent (preferably zinc phthalocyanine, more preferably polyhalogenated zinc phthalocyanine) may, if necessary, be subjected to rosin treatment, surface treatment using pigment derivatives into which acidic or basic groups have been introduced, grafting treatment of the pigment surface with polymer compounds, atomization treatment by sulfuric acid atomization method, washing treatment with organic solvents or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc.

[0014] The green coloring agent (preferably zinc phthalocyanine, more preferably polyhalogenated zinc phthalocyanine) is preferably used in the form of a dispersion in which it is uniformly dispersed in a solvent. This dispersion can be obtained by mixing the green coloring agent (preferably zinc phthalocyanine, more preferably polyhalogenated zinc phthalocyanine) in a solvent. A dispersant may be added as needed.

[0015] The dispersant may be cationic, anionic, nonionic, or amphoteric, and examples include polyester, polyamine, and acrylic dispersants. These dispersants may be used individually or in combination of two or more. Examples of dispersants include those traded as KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers (manufactured by Zeneca Corporation), EFKA (manufactured by BASF), Azisper (manufactured by Ajinomoto Fine Techno Co., Ltd.), and Disperbyk (manufactured by Bic Chemie). When a dispersant is used, the amount used is preferably 100 parts by mass or less, and more preferably 5 parts by mass or more and 50 parts by mass or less, per 100 parts by mass of pigment. When the amount of pigment dispersant used is within the above range, a pigment dispersion in which the pigment is uniformly dispersed in the solvent tends to be obtained.

[0016] The solvent is not particularly limited and can be any solvent similar to solvent (E) in the colored resin composition of the present invention. Among these, 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, 3-methoxybutyl acetate, 3-methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone, N,N-dimethylformamide, etc. are preferred, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, dipropylene glycol methyl ether acetate, ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol, ethyl 3-ethoxypropionate, etc. are more preferred. The amount of solvent used is not particularly limited, but it is preferable to use the solvent in such a way that the solid content concentration in the pigment dispersion is adjusted to 3 to 30% by mass, more preferably 5 to 25% by mass.

[0017] The coloring agent (A) may also contain a second coloring agent other than a green coloring agent (preferably zinc phthalocyanine, more preferably polyhalogenated zinc phthalocyanine), such as a yellow coloring agent or a blue coloring agent, which may be a pigment and / or dye. It is preferable that the coloring agent (A) further contains a yellow coloring agent.

[0018] Pigments include organic and inorganic pigments, as well as compounds classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of organic 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, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, and 214; CI Pigment Blue: Blue pigments such as 15, 15:3, 15:4, 15:6, 60; CI Pigment Violet: Violet pigments such as 1, 19, 23, 29, 32, 36, 38; Green pigments other than zinc phthalocyanine polyhalogenates, such as CI Pigment Green 7 and 36; These are some examples.

[0019] In particular, the pigment preferably includes at least one selected from the group consisting of green pigments other than zinc phthalocyanine, yellow pigments, and blue pigments, and it is preferable that the blue pigment is included together with the yellow pigment. Other than zinc phthalocyanine, preferred green, yellow, and blue pigments are CI Pigment Yellow 138, 139, 150, 185, CI Pigment Blue 15:3, 15:6, and CI Pigment Green 7, 36. Two or more of these pigments may be used.

[0020] The pigment may, if necessary, be subjected to rosin treatment, surface treatment using pigment derivatives or pigment dispersants into which acidic or basic groups have been introduced, grafting treatment of the pigment surface with polymer compounds, atomization treatment by sulfuric acid atomization method, washing treatment with organic solvents or water to remove impurities, removal treatment by ion exchange method for ionic impurities, etc. Furthermore, it is preferable that the pigment has a uniform particle size. By dispersing with a pigment dispersant, a pigment dispersion can be obtained in which the pigment is uniformly dispersed in the solution.

[0021] As the pigment dispersant, commercially available surfactants can be used, including silicone-based, fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric, polyester-based, polyamine-based, and acrylic-based surfactants. Examples of such surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid modified polyesters, tertiary amine-modified polyurethanes, polyethyleneimines, and other trade names such as KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solpers (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by BASF Japan Ltd.), Azisper (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), and Disperbyk (manufactured by Bic Chemie). These can be used individually or in combination of two or more.

[0022] When a pigment dispersant is used, the amount used is preferably 100% by mass or less, and more preferably 5 to 50% by mass, relative to the pigment. When the amount of pigment dispersant used is within the above range, a pigment dispersion with a uniform dispersion state tends to be obtained.

[0023] The dyes are not particularly limited and any known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as having hue other than pigments in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in Dyeing Notes (Irozome-sha). In addition, based on chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squalyllium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Of these, organic solvent-soluble dyes are preferred.

[0024] From the viewpoint of high color reproducibility, the total colorant content is 45.5% by mass or more relative to the solid content of the colored resin composition, preferably 46.0% by mass or more, more preferably 46.5% by mass or more, and also preferably 65% ​​by mass or less, more preferably 63% by mass or less, and even more preferably 61% by mass or less.

[0025] The content of the green coloring agent can be adjusted as appropriate to achieve the desired chromaticity. From the viewpoint of high color reproducibility, it is preferably 35% by mass or more and 99.9% by mass or less relative to the solid content of the total coloring agent. The lower limit of the green coloring agent content is more preferably 40% by mass or more, even more preferably 50% by mass or more, and especially preferably 60% by mass or more. The upper limit of the green coloring agent content is more preferably 98% by mass or less, even more preferably 95% by mass or less, and especially preferably 90% by mass or less. From the viewpoint of high color reproducibility, the content of the green coloring agent is preferably 5% to 60% by mass, more preferably 10% to 55% by mass, even more preferably 15% to 50% by mass, and even more preferably 20% to 45% by mass, relative to the solid content of the colored resin composition.

[0026] When the coloring agent contains both CI Pigment Green 59 and CI Pigment Green 58, the content ratio of CI Pigment Green 59 to CI Pigment Green 58, expressed as "Content of CI Pigment Green 59:Content of CI Pigment Green 58," should be in the range of 0.1 to 99.9:99.9 to 0.1, preferably 1 to 99:99 to 1. These content ratios can be adjusted as appropriate to the desired color.

[0027] When a green pigment other than zinc phthalocyanine is included, the amount of the green pigment other than zinc phthalocyanine used is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, even more preferably 10 parts by mass or more, preferably 2000 parts by mass or less, more preferably 300 parts by mass or less, and even more preferably 100 parts by mass or less, per 100 parts by mass of zinc phthalocyanine.

[0028] The yellow coloring agent may be either a yellow pigment or a yellow dye, but a yellow pigment is preferred. The content of the total yellow pigment is preferably 5% by mass or more and 40% by mass or less, more preferably 10% by mass or more, even more preferably 15% by mass or more, and even more preferably 20% by mass or more, relative to the solid content of the total colorant. The total yellow pigment content is preferably 1% to 30% by mass, more preferably 25% by mass or less, and even more preferably 20% by mass or less, relative to the solid content of the total colored resin composition.

[0029] The blue coloring agent may be either a blue pigment or a blue dye, but a blue pigment is preferred. The total blue pigment content is preferably 0.1% to 30% by mass, more preferably 1% to 25% by mass, and even more preferably 3% to 20% by mass, relative to the solid content of the total colorants. The total blue pigment content is preferably 1% to 30% by mass, more preferably 25% by mass or less, and even more preferably 20% by mass or less, relative to the solid content of the total colored resin composition.

[0030] The total amount of coloring agent (A) is preferably 25 to 65% by mass, more preferably 30 to 60% by mass, and even more preferably 35 to 55% by mass, based on 100% by mass of the solid content of the colored resin composition.

[0031] <Resin (B)> The resin containing the cyclic ether structure is preferably a copolymer containing structural units derived from monomers having an oxiranyl group and an ethylenically unsaturated bond (preferably (b1), (b2) described later). Furthermore, the resin may be a copolymer containing structural units derived from monomers that do not contain a cyclic ether structure, in which case the colored resin composition will contain a compound having a cyclic ether structure.

[0032] The following description collectively includes resins containing a cyclic ether structure and resins not containing a cyclic ether structure. The resin (B) used in this invention may be an alkali-soluble resin. Examples of resin (B) include the following resins [K1] to [K6]. A copolymer of resin [K1] at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "(a)") and a monomer (b) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)"). A copolymer of resin [K2](a) and (b) and monomer (c) copolymerizable with (a) (however different from (a) and (b)) (hereinafter sometimes referred to as "(c)"). A copolymer of resin [K3](a) and (c). A resin obtained by reacting a copolymer of resin [K4](a) and (c) with (b). A resin obtained by reacting (a) with a copolymer of resin [K5](b) and (c). A resin obtained by reacting a copolymer of resin [K6](b) and (c) with (a), and then reacting it with a carboxylic acid anhydride.

[0033] (a) specifically includes unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing carboxyl groups, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride (Hymic anhydride);

[0034] Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate; Examples include unsaturated acrylates containing both a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Of these, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred in terms of copolymerization reactivity and solubility in alkaline aqueous solutions.

[0035] (b) refers to a polymerizable compound having a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring (epoxy ring), an oxetane ring, and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. Preferred (b) is a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group. Examples of (b) include the monomer (b1) having this epoxy group and an ethylenically unsaturated bond, as well as the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (b2) (hereinafter sometimes referred to as "(b2)"), the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (b3) (hereinafter sometimes referred to as "(b3)"), and so on. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0036] (b1) includes monomers having an epoxidized structure of unsaturated aliphatic hydrocarbons (b1-1) (hereinafter sometimes referred to as "(b1-1)") and monomers having an epoxidized structure of unsaturated alicyclic hydrocarbons (b1-2) (hereinafter sometimes referred to as "(b1-2)").

[0037] (b1-1) includes glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis(glycidyl Examples include oxymethylstyrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0038] Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (I), and compounds represented by formula (II).

[0039] [ka]

[0040] [In equations (I) and (II), R a and R b Each of these independently 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 hydroxyl group. X 1 and X 2each independently represents a single bond, *-R c -, *-R c -O-, *-R c -S- or *-R c -NH-. R c represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bonding site to O.]

[0041] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R a and R b are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

[0042] 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 1 and X 2 are preferably a single bond, a methylene group, an ethylene group, a *-CH2-O- group, or a *-CH2CH2-O- group, and more preferably a single bond or a *-CH2CH2-O- group. * represents a bonding site to O.

[0043] Compounds represented by formula (I) include those represented by formulas (I-1) to (I-15). Preferably, these are formulas (I-1), (I-3), (I-5), (I-7), (I-9), (I-11) to (I-15). More preferably, these are formulas (I-1), (I-7), (I-9), and (I-15).

[0044] [ka]

[0045] [ka]

[0046] Compounds represented by formula (II) include those represented by formulas (II-1) to (II-15). Preferably, these include formulas (II-1), (II-3), (II-5), (II-7), (II-9), and (II-11) to (II-15). More preferably, these include formulas (II-1), (II-7), (II-9), and (II-15).

[0047] [ka]

[0048] [ka]

[0049] The compound represented by formula (I) and the compound represented by formula (II) can each be used individually. They can also be mixed in any ratio. When mixed, the mixing ratio is preferably 5:95 to 95:5 in the form of formula (I):(II), more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

[0050] As the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, and 3-ethyl-3-acryloyloxyethyl oxetane.

[0051] As the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Specifically, examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0052] (c) includes methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] Decane-8-yl(meth)acrylate (in the relevant technical field, it is commonly called "dicyclopentanyl(meth)acrylate". It is also sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6Decen-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the relevant art), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate, and other (meth)acrylic acid esters; Hydroxyl group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Diethyl maleate, diethyl fumarate, diethyl itaconate, and other dicarboxylic acid diesters; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybic Chlo[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- Bicyclounsaturated compounds such as ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl)maleimide; Examples include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like. Of these, benzyl (meth)acrylate, tricyclodecyl (meth)acrylate, styrene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, and bicyclo[2.2.1]hepto-2-ene are preferred in terms of copolymerization reactivity and heat resistance. Furthermore, benzyl (meth)acrylate and tricyclodecyl (meth)acrylate are more preferred due to their excellent developability during pattern formation.

[0053] In resin [K1], the ratio of structural units derived from each is preferably within the following ranges among all structural units constituting resin [K1]. (a) Structural units derived from (a); 2-50 mol% (more preferably 10-45 mol%) Structural units derived from (b), particularly structural units derived from (b1); 50-98 mol% (more preferably 55-90 mol%) When the ratio of structural units of resin [K1] falls within the above range, the resulting pattern tends to exhibit superior storage stability, developability, and solvent resistance.

[0054] The resin [K1] can be manufactured by the method described in the literature "Experimental Methods for Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and by referring to the cited literature.

[0055] Specifically, a method involves charging predetermined amounts of (a) and (b) (especially (b1)), a polymerization initiator, and a solvent into a reaction vessel, and then stirring, heating, and maintaining the temperature under a deoxygenated atmosphere. The polymerization initiator and solvent used here are not particularly limited, and any commonly used in this field can be used. Examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.). As for the solvent, any solvent that dissolves each monomer is acceptable, and solvent (E), described later, can be used as the solvent for the colored resin composition.

[0056] The resulting copolymer may be used as is after the reaction, as a concentrated or diluted solution, or as a solid (powder) obtained by methods such as reprecipitation. In particular, by using solvent (E), described later, as the solvent during polymerization, the reaction solution can be used as is, simplifying the manufacturing process.

[0057] In resin [K2], the ratio of structural units derived from each is preferably within the following ranges among all structural units constituting resin [K2]. (a) Structural units derived from (a); 4-45 mol% (more preferably 10-30 mol%) Structural units derived from (b), particularly structural units derived from (b1); 2-95 mol% (more preferably 5-80 mol%) (c) Structural units derived from (c); 1-65 mol% (more preferably 5-60 mol%) When the ratio of structural units of resin [K2] falls within the above range, the resulting pattern tends to exhibit superior storage stability, developability, solvent resistance, heat resistance, and mechanical strength.

[0058] Resin [K2] can be manufactured in the same manner as described for the manufacturing method of resin [K1]. Specifically, a method involves charging predetermined amounts of (a), (b) (especially (b1)), and (c), a polymerization initiator, and a solvent into a reaction vessel, and then stirring, heating, and maintaining the temperature under a deoxygenated atmosphere. The resulting copolymer may be used as is from the reaction solution, from a concentrated or diluted solution, or from a solid (powder) obtained by methods such as reprecipitation.

[0059] In resin [K3], the ratio of structural units derived from each is preferably within the following ranges among all structural units constituting resin [K3]. (a) 2-55 mol%, more preferably 10-50 mol% (c) 45-98 mol%, more preferably 50-90 mol% Resin [K3] can be manufactured in the same manner as described for the manufacturing method of resin [K1].

[0060] The 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 of (b), particularly the oxirane ring of (b1), to the carboxylic acid and / or carboxylic acid anhydride of (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 structural units derived from each is preferably within the following ranges of all structural units constituting the copolymer of (a) and (c). (a) 5-50 mol%, more preferably 10-45 mol% (c) 50-95 mol%, more preferably 55-90 mol%

[0061] Next, a portion of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms in (b), particularly the oxirane ring of (b1). Following the production of the copolymer of (a) and (c), the atmosphere inside the flask is replaced from nitrogen to air, and (b) (especially (b1)), a reaction catalyst for the reaction between a carboxylic acid or carboxylic acid anhydride and a cyclic ether (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone) are added to the flask and reacted at 60 to 130°C for 1 to 10 hours to obtain the resin [K4]. The amount of (b) used, particularly the amount of (b1), is preferably 5 to 80 moles, and more preferably 10 to 75 moles, per 100 moles of (a). This range tends to result in a good balance of storage stability, developability, solvent resistance, heat resistance, mechanical strength, and sensitivity. Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K4], and (b1-1) is even more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5% by mass relative to the total amount of (a), (b) (especially (b1)), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5% by mass relative to the total amount of (a), (b), and (c). The reaction conditions, such as the preparation method, reaction temperature, and time, can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization. Similarly, the preparation method and reaction temperature can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization.

[0062] As a first step, resin [K5] is produced in the same manner as the method for producing resin [K1] described above, to obtain a copolymer of (b) (especially (b1)) and (c). As described above, the obtained copolymer may be used as is after the reaction, or a concentrated or diluted solution may be used, or it may be used after being extracted as a solid (powder) by methods such as reprecipitation. The ratio of structural units derived from (b) (especially (b1)) and (c) is preferably within the following range with respect to the total number of moles of all structural units constituting the copolymer. Structural units derived from (b), particularly structural units derived from (b1); 5-95 mol% (more preferably 10-90 mol%) (c) Structural units derived from (c); 5-95 mol% (more preferably 10-90 mol%)

[0063] Furthermore, resin [K5] can be obtained by reacting a cyclic ether derived from (b) in a copolymer of (b) (particularly (b1)) and (c) with a carboxylic acid or carboxylic acid anhydride from (a) under the same conditions as for the production of resin [K4]. The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b) (especially (b1)). Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K5], and (b1-1) is even more preferred.

[0064] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of carboxylic acid anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride (Hymic anhydride). Of the resins [K1] to [K6], the preferred resin is resin [K1] or [K2].

[0065] Resin (B) (preferably a resin containing a cyclic ether structure) specifically includes 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.02,6 Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer [K2]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, and resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer [K4]; Examples of resins include those obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid [K5], and resins obtained by reacting a tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate copolymer with (meth)acrylic acid [K6], among which resins obtained by reacting a resin obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then further reacting it with tetrahydrophthalic anhydride [K1]. Other resins (B) besides those mentioned above include, specifically, resins such as 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer [K2]; and resins such as benzyl(meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, and benzyl(meth)acrylate / tricyclodecyl(meth)acrylate / (meth)acrylic acid copolymer [K3]. These resins may be used individually or in combination of two or more types.

[0066] The weight-average molecular weight of resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. When the molecular weight is within the above range, the solubility in the developer of the unexposed areas is high, and the residual film rate and hardness of the resulting pattern tend to be high. The molecular weight distribution of resin (B) [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] is preferably 1.1 to 6, and more preferably 1.2 to 4.

[0067] The solid content acid value of resin (B) is preferably 85 mg-KOH / g or more, more preferably 100 mg-KOH / g or more, and even more preferably 110 mg-KOH / g or more. Furthermore, the solid content acid value is preferably 200 mg-KOH / g or less, more preferably 180 mg-KOH / g or less, and even more preferably 160 mg-KOH / g or less. When the solid content acid value of resin (B) is within the above range, a good coloring pattern with good shape tends to be obtained from the colored resin composition. Here, the acid value is measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0068] The content of resin (B) is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and even more preferably 15 to 30% by mass, based on 100% by mass of the solid content of the colored resin composition. When the content of resin (B) is within the above range, the solubility of the unexposed areas in the developer tends to be high.

[0069] <Polymerizable compound (C)> The polymerizable compound (C) is not particularly limited as long as it is a compound having a group that can undergo polymerization, and examples include compounds that can undergo ring-opening polymerization and compounds that can undergo addition polymerization.

[0070] (Compounds that can undergo ring-opening polymerization) Compounds capable of ring-opening polymerization include those having a cyclic ether structure with approximately 2 to 4 carbon atoms (for example, an oxirane ring (also called an epoxy ring), an oxetane ring, and a tetrahydrofuran ring (also called an oxolane ring)). More preferably, compounds capable of ring-opening polymerization are those having an oxirane ring or an oxetane ring, and even more preferably are compounds containing an epoxy group.

[0071] The epoxy compound (hereinafter also referred to as the epoxy compound) can have one or more oxiranyl groups. However, the epoxy compound is different from resin (B). When a predetermined amount of such an epoxy compound or the aforementioned epoxy-containing resin is used, the thickness of the colored coating can be reduced and the dielectric loss tangent can be reduced even if the total colorant content is high. The number of oxiranyl groups in the epoxy compound may be one or more, two or more, or three or more.

[0072] The acid value of the epoxy compound is preferably less than 30 mg-KOH / g, more preferably 20 mg-KOH / g or less, even more preferably 10 mg-KOH / g or less, and particularly preferably 0 mg-KOH / g.

[0073] Examples of the epoxy compounds include ring-less epoxy compounds such as epoxidized isoprene (co)polymers and epoxidized butadiene (co)polymers, as well as ring-containing epoxy compounds. Examples of the ring include alicyclic hydrocarbon rings and aromatic hydrocarbon rings. These may be heterocyclic rings, but hydrocarbon rings are preferred.

[0074] Alicyclic hydrocarbon rings include cycloalkane rings with 3 to 10 carbon atoms such as cyclopropane rings, cyclobutane rings, cyclopentane rings, cyclohexane rings, cycloheptane rings, and cyclooctane rings; cycloalkene rings with 5 to 10 carbon atoms such as cyclopentene rings, cyclohexene rings, cycloheptene rings, and cyclooctene rings; bicyclo[2.2.1]heptane rings (norbornane rings), 1,7,7-trimethylbicyclo[2.2.1]heptane rings (isobornane rings), bicyclo[2.2.2]octane rings, and tricyclo[5.2.1.0 2,6 ] Decane ring, tricyclo[3.3.1.1 3,7 Examples include polycyclic alicyclic hydrocarbon rings with 7 to 15 carbon atoms, such as decane rings (adamantane rings). The alicyclic hydrocarbon ring is preferably a cycloalkane ring having 4 to 9 carbon atoms, more preferably a cycloalkane ring having 5 to 8 carbon atoms. Among these, cyclohexane is more preferred.

[0075] Examples of aromatic hydrocarbon rings include benzene rings, naphthalene rings, and anthracene rings.

[0076] As for the ring-containing epoxy compound, compounds having one or more rings and two or more oxiranyl groups are preferred, and epoxy compounds having two or more rings and two or more oxiranyl groups are more preferred. In the ring-containing epoxy compound, the number of oxiranyl groups per ring is preferably 0.8 to 1.2, and more preferably 0.9 to 1.1.

[0077] Examples of epoxy compounds having an alicyclic hydrocarbon ring and two or more oxiranyl groups include the 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol. Examples of the epoxy compounds include 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (Celoxide 2021P, manufactured by Daicel Corporation) and ε-caprolactone-modified 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (Celoxide 2081, manufactured by Daicel Corporation).

[0078] Examples of epoxy compounds having an aromatic hydrocarbon ring and two or more oxyranyl groups include bisphenol-type epoxy compounds such as bisphenol A-type epoxy compounds, bisphenol F-type epoxy compounds, brominated bisphenol A-type epoxy compounds, and brominated bisphenol F-type epoxy compounds; novolac-type epoxy compounds such as phenol novolac-type epoxy compounds and cresol novolac-type epoxy compounds; biphenyl-type epoxy compounds; trishydroxyphenylmethane-type epoxy compounds; tetraphenolethane-type epoxy compounds; and epoxidized styrene polymers such as epoxidized styrene-butadiene copolymers and epoxidized styrene-isoprene copolymers. Among these, bisphenol A-type epoxy compounds and orthocresol novolac-type epoxy compounds are particularly preferred.

[0079] The (weight) average molecular weight of the epoxy compound is preferably less than 3000, more preferably 2900 or less, also preferably 50 or more, more preferably 200 or more, and even more preferably 350 or more.

[0080] The epoxy equivalent of the epoxy compound is preferably 30 g / equivalent to 400 g / equivalent, more preferably 50 g / equivalent to 350 g / equivalent, even more preferably 100 g / equivalent to 300 g / equivalent, and particularly preferably 150 g / equivalent to 250 g / equivalent. The epoxy equivalent can be measured by the method specified in JIS K7236.

[0081] The content of the ring-opening polymerization compound is preferably 0.01% to 10% by mass, more preferably 0.1% to 5% by mass, and even more preferably 0.2% to 5% by mass, based on 100% by mass of the colored resin composition (solids).

[0082] (Compounds that can undergo addition polymerization) The polymerizable compound (hereinafter also referred to as the polymerizable compound (C1)) is not particularly limited as long as it is a compound that can be polymerized by active radicals generated from the polymerization initiator (D) upon irradiation with light, and examples include compounds having polymerizable ethylenically unsaturated bonds. The weight-average molecular weight of the polymerizable compound (C1) is preferably 3,000 or less.

[0083] In particular, the polymerizable compound (C1) is preferably a photopolymerizable compound having three or more ethylenically unsaturated bonds, such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, and tetrapentaerythritol Examples include ethanol (meth)acrylate, tris(2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate. Among these, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are particularly noteworthy.

[0084] The polymerizable compound (C1) content is preferably 20 to 150 parts by mass, and more preferably 80 to 120 parts by mass, per 100 parts by mass of resin (B) in the colored resin composition.

[0085] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc., upon the action of light or heat and can initiate polymerization; any known polymerization initiator can be used. Examples of polymerization initiators (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds. Only one polymerization initiator (D) may be used, or two or more may be used. A preferred polymerization initiator (D) is an O-acyloxime compound.

[0086] The O-acyloxime compound is a compound having the structure represented by formula (d). Hereinafter, * represents a bond.

[0087] [ka]

[0088] The O-acyloxime compound is preferably at least one selected from the group consisting of, for example, the compound represented by formula (d1) below (hereinafter sometimes referred to as compound (d1)), the compound represented by formula (d2) below (hereinafter sometimes referred to as compound (d2)), and the compound represented by formula (d3) below (hereinafter sometimes referred to as compound (d3)).

[0089] [ka]

[0090] [In equations (d1) to (d3), R d1 This represents an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, an optionally substituted heterocyclic group having 3 to 36 carbon atoms, an optionally substituted alkyl group having 1 to 15 carbon atoms, or an optionally substituted group formed by combining an aromatic hydrocarbon group with an alkanediyl group derived from the alkyl group, wherein the methylene group (-CH2-) contained in the alkyl group is -O-, -CO-, -S-, -SO2-, or -NR d5- may be replaced with this. R d2 This represents an aromatic hydrocarbon group having 6 to 18 carbon atoms, a heterocyclic group having 3 to 36 carbon atoms, or an alkyl group having 1 to 10 carbon atoms. R d3 This represents an aromatic hydrocarbon group having 6 to 18 carbon atoms, which may have substituents, or a heterocyclic group having 3 to 36 carbon atoms, which may have substituents. R d4 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms, which may have substituents, or an aliphatic hydrocarbon group having 1 to 15 carbon atoms, which may have substituents, wherein the methylene group (-CH2-) contained in the aliphatic hydrocarbon group may be replaced with -O-, -CO-, or -S-, the methine group (-CH<) contained in the aliphatic hydrocarbon group may be replaced with -PO3<, and the hydrogen atoms contained in the aliphatic hydrocarbon group may be substituted with OH groups. R d5 This represents an alkyl group having 1 to 10 carbon atoms, and the methylene group (-CH2-) contained in the alkyl group may be replaced with -O- or -CO-.

[0091] R d1 The number of carbon atoms in the aromatic hydrocarbon group represented is preferably 6 to 15, more preferably 6 to 12, and even more preferably 6 to 10. Examples of the aromatic hydrocarbon group include phenyl, naphthyl, anthryl, phenanthryl, biphenyl, and terphenyl groups, with phenyl and naphthyl groups being more preferred, and phenyl groups being particularly preferred. Also R d1 The aromatic hydrocarbon group represented by may have one or more substituents. The substituents are preferably substituted at the α or γ position of the aromatic hydrocarbon group, and more preferably at the γ position. Examples of substituents include C1-C15 alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, and pentadecyl groups; halogen atoms such as fluorine, chlorine, iodine, and bromine atoms; and the like. The alkyl group as a substituent preferably has 1 to 10 carbon atoms, and more preferably 1 to 7 carbon atoms. The alkyl group as a substituent may be linear, branched, or cyclic, or it may be a combination of a linear group and a cyclic group. The methylene group (-CH2-) contained in the alkyl group as a substituent may be replaced with -O- or -S-. Furthermore, the hydrogen atoms contained in the alkyl group may be substituted with halogen atoms such as fluorine, chlorine, iodine, or bromine, and are preferably substituted with fluorine atoms.

[0092] R d1 Examples of alkyl groups as substituents on the aromatic hydrocarbon group represented by include the group represented by the following formula. In the formula, * represents a bond.

[0093] [ka]

[0094] [ka]

[0095] R d1 Examples of aromatic hydrocarbon groups that may have substituents represented by the formula shown below include the group represented by the formula shown below. In the formula, * represents a bond.

[0096] [ka]

[0097] [ka]

[0098] R d1 As an aromatic hydrocarbon group which may have substituents represented by the formula shown below, the group represented by the formula shown below is preferred.

[0099] [ka]

[0100] [In the formula, R d6 R represents an alkyl group having 1 to 10 carbon atoms, which may be substituted with a halogen atom. d6 The hydrogen atoms contained in may be substituted with halogen atoms. m2 represents an integer from 1 to 5.

[0101] R d6 The alkyl group represented by R is d1 Examples of substituents on the aromatic hydrocarbon group represented by R include groups similar to the alkyl groups exemplified above. d6 The number of carbon atoms is preferably 2 to 7, and more preferably 2 to 5. Also, R d6 The alkyl group represented by may be linear, branched, or cyclic, but is preferably linear (linear or branched). R d6 Examples of halogen atoms that may substitute for hydrogen atoms include fluorine atoms, chlorine atoms, iodine atoms, and bromine atoms, with fluorine atoms being particularly preferred. Also, R d6 Preferably, two to ten hydrogen atoms in the compound are replaced by halogen atoms, and preferably three to six hydrogen atoms are replaced by halogen atoms. d6 The substitution position of the O-group is preferably the ortho position or the para position, with the para position being particularly preferred. Furthermore, m2 is preferably 1 to 2, and particularly preferably 1.

[0102] R d1 The number of carbon atoms in the heterocyclic group represented by is preferably 3 to 20, more preferably 3 to 10, and even more preferably 3 to 5. Examples of such heterocyclic groups include pyrrolyl, furyl, thienyl, indolyl, benzofuryl, and carbazolyl groups. Also R d1 The heterocyclic group represented by may have one or more substituents. The substituents include R d1Examples of substituents that the aromatic hydrocarbon group represented by may have include groups similar to those exemplified above.

[0103] R d1 The number of carbon atoms in the alkyl group represented is preferably 1 to 12. d1 Examples of alkyl groups represented by R include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, and pentadecyl groups. These alkyl groups may be linear, branched, or cyclic, and may be a combination of a linear (linear or branched) group and a cyclic group. d1 In the alkyl group represented by , the methylene group (-CH2-) is -O-, -CO-, -S-, -SO2-, or -NR d5 It may be replaced by -, and the hydrogen atom may be substituted with an OH group or an SH group.

[0104] R d5 R represents an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms. The alkyl group may be linear (linear or branched) or cyclic, and may be any of linear, branched, or cyclic, or it may be a group that combines a linear group and a cyclic group. d5 In the alkyl group, the methylene group (-CH2-) may be replaced with -O- or -CO-.

[0105] R d1 Specific examples of alkyl groups that may have substituents represented by the formula below include the group represented by the formula below. * represents a bond.

[0106] [ka]

[0107] Furthermore, R d1Represented by an aromatic hydrocarbon group and the above R d1 The number of carbon atoms in the group combined with the alkanediyl group derived from the alkyl group represented by is preferably 7 to 33, more preferably 7 to 18, and even more preferably 7 to 12. The combined group may have one or more substituents, and examples of substituents include aromatic hydrocarbon groups and groups similar to those exemplified as substituents that the alkyl group may have. d1 Represented by an aromatic hydrocarbon group and the above R d1 An example of a group formed by combining an alkyl group represented by with an alkanediyl group is the aralkyl group, specifically the group represented by the following formula. In the formula, * represents a bond.

[0108] [ka]

[0109] Among them, R d1 Preferably, the atom is an aromatic hydrocarbon group that may have substituents or an alkyl group that may have substituents, and more preferably, an aromatic hydrocarbon group that may have substituents.

[0110] R d2 The number of carbon atoms in the aromatic hydrocarbon group represented is preferably 6 to 15, more preferably 6 to 12, and even more preferably 6 to 10. Examples of the aromatic hydrocarbon group include phenyl, naphthyl, anthryl, phenanthryl, biphenyl, and terphenyl groups. R d2 The number of carbon atoms in the heterocyclic group represented by is preferably 3 to 20, more preferably 3 to 10, and even more preferably 3 to 5. Examples of such heterocyclic groups include pyrrolyl, furyl, thienyl, indolyl, benzofuryl, and carbazolyl groups. R d2The number of carbon atoms in the alkyl group represented by is preferably 1 to 7, more preferably 1 to 5, and even more preferably 1 to 3. Examples of the alkyl group include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups. The alkyl group may be linear, branched, or cyclic, or it may be a combination of a linear group and a cyclic group.

[0111] R d2 Preferably, the group is a linear alkyl group, more preferably a linear alkyl group having 1 to 5 carbon atoms, and even more preferably a linear alkyl group having 1 to 3 carbon atoms, and is particularly preferably a methyl group.

[0112] R d3 The number of carbon atoms in the aromatic hydrocarbon group represented is preferably 6 to 15, more preferably 6 to 12, and even more preferably 6 to 10. Examples of the aromatic hydrocarbon group include phenyl, naphthyl, anthryl, phenanthryl, biphenyl, and terphenyl groups, with phenyl and naphthyl groups being more preferred. Also, R d3 The aromatic hydrocarbon group represented by may have one or more substituents. Preferably, the substituents are substituted at the α or γ position of the aromatic hydrocarbon group. Preferred substituents are aliphatic hydrocarbon groups having 1 to 15 carbon atoms, specifically alkyl groups having 1 to 15 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups; and alkenyl groups having 1 to 15 carbon atoms such as ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, nonenyl, and decenyl groups. R d3The aliphatic hydrocarbon group that the aromatic hydrocarbon group represented by may have is more preferably 1 to 7 carbon atoms, and the aliphatic hydrocarbon group may be linear, branched, or cyclic, or may be a combination of a linear group and a cyclic group. Furthermore, the methylene group (-CH2-) contained in the aliphatic hydrocarbon group may be replaced with -O-, -CO-, or -S-, and the methine group (-CH<) may be replaced with -N<.

[0113] R d3 Examples of aliphatic hydrocarbon groups that the aromatic hydrocarbon group represented by may have include the group represented by the following formula. In the formula, * represents a bond.

[0114] [ka]

[0115] R d3 Examples of aromatic hydrocarbon groups that may have substituents represented by the formula shown below include the group represented by the formula shown below. In the formula, * represents a bond.

[0116] [ka]

[0117] R d3 The number of carbon atoms in the heterocyclic group represented by is preferably 3 to 20, more preferably 3 to 10, and even more preferably 3 to 5. Examples of such heterocyclic groups include pyrrolyl, furyl, thienyl, indolyl, benzofuryl, and carbazolyl groups. Also, R d3 The heterocyclic group represented by may have one or more substituents, and the substituents may be R d1 Examples of substituents that the aromatic hydrocarbon group represented by may have include groups similar to those exemplified above.

[0118] Among them, R d3The substituent is preferably an aromatic hydrocarbon group having substituents, and the substituent is preferably a chain alkyl group having 1 to 7 carbon atoms (more preferably 1 to 3 carbon atoms), and the number of substituents is preferably 2 to 5.

[0119] R d4 The number of carbon atoms in the aromatic hydrocarbon group represented is preferably 6 to 15, more preferably 6 to 12, and even more preferably 6 to 10. Examples of the aromatic hydrocarbon group include phenyl, naphthyl, anthryl, phenanthryl, biphenyl, and terphenyl groups, with phenyl and naphthyl groups being more preferred, and phenyl being even more preferred. Also R d4 The aromatic hydrocarbon group represented by may have one or more substituents. The substituents include R d1 Examples of substituents that may be present on the aromatic hydrocarbon group include groups similar to those mentioned above.

[0120] R d4 The number of carbon atoms in the aliphatic hydrocarbon group represented is preferably 1 to 13, more preferably 2 to 10, and even more preferably 4 to 9. d4 Examples of aliphatic hydrocarbon groups represented by include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, and pentadecyl groups; and alkenyl groups such as ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, butadecenyl, and pentadecenyl groups. These aliphatic hydrocarbon groups may be linear (linear or branched), cyclic, or a combination of a linear and a cyclic group. d4 In the aliphatic hydrocarbon group, the methylene group (-CH2-) may be replaced with -O-, -CO-, or -S-, the methine group (-CH<) may be replaced with -PO3<, and the hydrogen atoms contained in the aliphatic hydrocarbon group may be substituted with OH groups.

[0121] R d4 Examples of aliphatic hydrocarbon groups that may have substituents represented by the formula shown below include the group represented by the formula shown below. In the formula, * represents a bond.

[0122] [ka]

[0123] R d4 It is preferably a chain-like aliphatic hydrocarbon group which may have substituents, more preferably a chain-like alkyl group which has no substituents, and even more preferably a branched chain-like alkyl group which has no substituents.

[0124] Compound (d1) refers to compounds represented by formula (d1), specifically compounds represented by formula (d1-1) to (d1-67). In Tables 1-7, * represents a bond.

[0125] [ka]

[0126] [Table 1]

[0127] [Table 2]

[0128] [Table 3]

[0129] [Table 4]

[0130] [Table 5]

[0131] [Table 6]

[0132] [Table 7]

[0133] Among these, compounds represented by formula (d1-3) to (d1-6), compounds represented by formula (d1-18) to (d1-52), compounds represented by formula (d1-55), compounds represented by formula (d1-56), compounds represented by formula (d1-60), and compounds represented by formula (d1-61) are preferred. More preferably are compounds represented by formula (d1-3) to (d1-6), compounds represented by formula (d1-18) to (d1-41), even more preferably compounds represented by formula (d1-24), compounds represented by formula (d1-36) to (d1-40), and particularly preferably compounds represented by formula (d1-24).

[0134] Compound (d1) can be produced by the manufacturing method described in Japanese Patent Publication No. 2014-500852.

[0135] Compound (d2) is, R d1 A C1-C15 alkyl group which may have substituents, R d2 These are alkyl groups having 1 to 10 carbon atoms. R d3 A C6-C18 aromatic hydrocarbon group which may have substituents, R d4 A compound in which the group is an aliphatic hydrocarbon group having 1 to 15 carbon atoms, which may have substituents, is preferred. Comfortable, R d1 This represents a methyl group, an ethyl group, or a propyl group. R d2 represents a methyl group, an ethyl group or a propyl group, and R d3 represents a phenyl group substituted with a methyl group, R d4 is a compound in which is a methyl group, an ethyl group or a propyl group, more preferably, R d1 and R d2 are methyl groups, R d3 is o-tolyl group and R d4 is a compound in which is an ethyl group.

[0136] Compound (d3) is a compound wherein R d1 is an optionally substituted alkyl group having 1 to 15 carbon atoms and R d2 is preferably a compound in which is an aromatic hydrocarbon group having 6 to 18 carbon atoms, more preferably, R d1 is a hexyl group and R d2 is a compound in which is a phenyl group.

[0137] Examples of such O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy Examples include -1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (all from BASF) and N-1919 (from ADEKA) may also be used. These O-acyloxime compounds tend to yield color filters with excellent lithography performance.

[0138] Alkylphenone compounds are compounds having a substructure represented by formula (d4) or formula (d5). In these substructures, the benzene ring may have substituents.

[0139] [ka]

[0140] Compounds having the structure represented by formula (d4) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used. Compounds having the structure represented by formula (d5) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyldimethyl ketal. In terms of sensitivity, alkylphenone compounds having the structure represented by formula (d4) are preferred.

[0141] Examples of biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Publication No. 6-75372, Japanese Patent Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2-chloro Examples include phenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and imidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group (see, for example, Japanese Patent Application Publication No. 7-10913, etc.). Among these, compounds represented by the following formula and mixtures thereof are preferred.

[0142] [ka]

[0143] Examples of triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-( Examples include 5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0144] Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

[0145] Furthermore, examples of polymerization initiators (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with polymerization initiators (D1) (especially amines) described later.

[0146] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 5 to 25 parts by mass, and even more preferably 10 to 20 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C1). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to increase and exposure time tends to be shortened, thus improving the productivity of color filters.

[0147] <Polymerization initiator (D1)> Polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When polymerization initiator (D1) is included, it is used in combination with the polymerization initiator (D). Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds. Thioxanthone compounds are preferred among these. Two or more polymerization initiators (D1) may be included.

[0148] Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michla's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.

[0149] Examples of alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0150] Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0151] Examples of carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0152] The content of the polymerization initiator (D1) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C1). When the amount of polymerization initiator (D1) is within this range, it is possible to form a colored pattern with even higher sensitivity, and the productivity of color filters tends to improve.

[0153] <Solvent (E)> The colored resin composition of the present invention preferably contains a solvent (E). Examples of solvent (E) include ester solvents (solvents containing -COO-), ether solvents other than ester solvents (solvents containing -O-), ether ester solvents (solvents containing both -COO- and -O-), ketone solvents other than ester solvents (solvents containing -CO-), alcohol solvents, aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxides.

[0154] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0155] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethole, and methylanisole.

[0156] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxy-2-methylpropionate Examples include ethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

[0157] 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.

[0158] Examples of alcoholic solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin. Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene. Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0159] Solvent (E) may be used in combination of two or more types. From the viewpoint of applicability and drying properties, organic solvents having a boiling point of 120°C to 180°C at 1 atm are preferred. Among these, 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, 3-methoxybutyl acetate, 3-methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide are preferred, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, dipropylene glycol methyl ether acetate, ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol, and ethyl 3-ethoxypropionate are more preferred.

[0160] The solvent (E) content is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, relative to the colored resin composition. In other words, the solid content of the colored resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. When the solvent (E) content is within the above range, the flatness during coating is good, and the display characteristics tend to be good because there is no shortage of color density when a color filter is formed.

[0161] <Leveling agent (F)> Examples of leveling agents (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants containing fluorine atoms. These may have polymerizable groups in their side chains.

[0162] Examples of silicone-based surfactants include surfactants that have siloxane bonds in their molecules. Specifically, examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0163] Examples of fluorine-based surfactants include surfactants having fluorocarbon chains in their molecules. Specifically, these include Florard® FC430 and FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac® F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), F-Top® EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon® S381, S382, SC101, and SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

[0164] Examples of silicone-based surfactants containing fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in their molecules. Specifically, examples include Megafac® R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0165] The content of the leveling agent (F) is preferably 0.001% by mass or more and 0.2% by mass or less, preferably 0.002% by mass or more and 0.1% by mass or less, and more preferably 0.005% by mass or more and 0.05% by mass or less, based on the total amount of the colored resin composition. Note that this content does not include the content of the pigment dispersant.

[0166] <Method for producing colored resin composition> The colored resin composition of the present invention contains a colorant (A) and a resin (B), and can be prepared by mixing a polymerizable compound (C1), a polymerization initiator (D), and optionally a solvent (E), a leveling agent (F), a polymerization initiator aid (D1), and other components.

[0167] <How to manufacture color filters> Methods for producing a colored pattern from the colored resin composition of the present invention include photolithography, inkjet printing, and other printing methods. Among these, photolithography is preferred. Photolithography is a method in which the colored resin composition is applied to a substrate, dried to form a colored composition layer, and then exposed to light through a photomask for development. In photolithography, by not using a photomask during exposure and / or by not developing, a colored coating film, which is a cured product of the colored composition layer, can be formed. The colored pattern or colored coating film formed in this way is the color filter of the present invention.

[0168] As substrates, glass plates such as quartz glass, borosilicate glass, aluminasilate glass, and soda-lime glass with a silica coating on the surface, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, and substrates on which aluminum, silver, or silver / copper / palladium alloy thin films are formed can be used. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates. Alternatively, a silicon substrate treated with HMDS (1,1,1,3,3,3-hexamethyldisilazane) may be used.

[0169] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be manufactured as follows. First, a colored resin composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying, and then dried to obtain a smooth colored composition layer. Coating methods include spin coating, slit coating, and slit and spin coating. The temperature for heat drying is preferably 30 to 120°C, and more preferably 50 to 110°C. The heating time is preferably 10 seconds to 5 minutes, and more preferably 30 seconds to 3 minutes. When performing vacuum drying, it is preferable to do so under a pressure of 50 to 150 Pa and at a temperature range of 20 to 25°C. The thickness of the colored composition layer is not particularly limited and can be appropriately selected according to the desired thickness of the color filter.

[0170] Next, the colored composition layer is exposed through a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate to the intended application is used. For exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferred. For example, light below 350 nm can be filtered out using a filter that cuts out this wavelength range, or light around 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specifically, examples of light sources include mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, etc. It is preferable to use exposure equipment such as a mask aligner (proximity exposure machine) and a stepper (reduction projection exposure machine) because they can uniformly irradiate the entire exposure surface with parallel light rays and accurately align the photomask with the substrate on which the colored composition layer is formed. A colored pattern is formed on the substrate by developing the colored composition layer after exposure by contacting it with a developer. During development, the unexposed parts of the colored composition layer are dissolved and removed by the developer. As the developer, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. Furthermore, the developer may also contain a surfactant. The development method can be any of the following: paddle method, dipping method, or spray method. Furthermore, the substrate may be tilted to any angle during development. After developing, it is preferable to wash the film with water. Furthermore, it is preferable to perform post-baking on the obtained coloring pattern. The post-baking temperature is preferably 80 to 250°C, more preferably 100 to 250°C, even more preferably 150 to 250°C, and even more preferably 160 to 235°C. The post-baking time is preferably 1 to 120 minutes, more preferably 2 to 120 minutes, even more preferably 10 to 60 minutes, and even more preferably 10 to 30 minutes.

[0171] Since the thickness of the resulting coating film affects adjacent pixels, it is preferable that the coating film be as thin as possible. In particular, if the film is thick, when the liquid crystal panel is manufactured, light from the light source may leak through two or more pixels, and when the panel is viewed from an angle, the vividness of the colors may be lost. The coating film after post-baking is preferably 4 μm or less or 3 μm or less, more preferably 2.8 μm or less, even more preferably 2.5 μm or less, and even more preferably 2.3 μm or less. The lower limit of the coating film is not particularly limited, but is usually 0.1 μm or more, preferably 0.2 μm or more, 0.5 μm or more, or 1 μm or more, and may be 1.5 μm or more.

[0172] The colored coating film is formed such that the film thickness after post-baking at 230°C for 30 minutes is 1 to 4 μm (preferably 1 to 3 μm, more preferably 2.8 μm or less, even more preferably 2.5 μm or less, and even more preferably 2.3 μm or less), and this is used in 2.8 × 10 5 When illuminated with an illuminance of lux (lx), it is preferable that the dielectric loss tangent tanδ at a frequency of 20 Hz is 0.20 or less. More preferably, the tanδ of the colored coating film is 0.18 or less, and even more preferably 0.15 or less. The closer the tanδ value is to 0, the better. The tanδ of the colored coating film is preferably measured on the surface opposite to the irradiated surface while the coating film is irradiated with a light, and a suitable commercially available light can be used. The irradiation of the colored coating film is, for example, at an illuminance of 1.5 × 10⁻⁶ 5 ~3.0×10 5This can be done within the range of lux (lx), and the brightness and irradiation distance of the light should be adjusted so that the illuminance falls within this range. In the embodiment described later, the illuminance is 2.8 × 10⁻¹⁰ 5 Measurements are taken in lux (lx). By irradiating the colored coating, it is possible to measure tanδ in an environment similar to when the colored coating (color filter) is actually applied to a display device. Without irradiation of the colored coating, the tanδ tends to be measured as small, for example, less than 0.04, making it difficult to evaluate or predict screen display problems that may occur when the colored coating is applied to a display device. When the colored coating (color filter) satisfies the above range of tanδ, screen flicker tends to be suppressed, making it suitable for use in mobile LCD screens, for example. The colored coating preferably satisfies the dielectric loss tangent and film thickness described above, and in the XYZ color system, satisfies 0 ≤ x ≤ 0.40 and 0.40 ≤ y ≤ 0.85 (preferably 0 ≤ x ≤ 0.35 and 0.50 ≤ y ≤ 0.85, more preferably 0 ≤ x ≤ 0.30 and 0.55 ≤ y ≤ 0.70).

[0173] By using the colored resin composition of the present invention, a color filter with particularly reduced dielectric loss tangent can be manufactured. This color filter is useful as a color filter for display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors. [Examples]

[0174] The present invention will be described in more detail below with reference to examples, but the present invention is not limited by the following examples, and it is certainly possible to implement it with appropriate modifications within the scope that is consistent with the spirit of the preceding and following descriptions, and all such modifications are included within the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "percent mass".

[0175] Synthesis Example 1 Into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel and a nitrogen inlet tube, 340 parts of propylene glycol monomethyl ether acetate was charged, the atmosphere in the flask was changed from air to nitrogen, and then the flask was heated to 80°C. Next, a mixed solution of 30 parts of acrylic acid, 60 parts of benzyl methacrylate, 10 parts of tricyclodecanyl methacrylate and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution obtained by dissolving 40 parts of a polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition of the initiator solution, the mixture was kept at 80°C for 3 hours and then cooled to room temperature, to obtain a copolymer (resin B1) solution having a viscosity of 210 mPas measured by a B-type viscometer (23°C) and a solid content of 33.9% by mass (hereinafter may be referred to as resin solution (B1)). The weight average molecular weight Mw of the obtained copolymer is 10.2×10 3 , the dispersity (molecular weight distribution) was 2.10, and the acid value in terms of solid content was 110 mg-KOH / g.

[0176] Synthesis Example 2 A proper amount of nitrogen was flowed into a 1 L flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with a nitrogen atmosphere, 362 parts by mass of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C while stirring. Subsequently, 58 parts by mass of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6A mixed solution of 167 parts by mass of a mixture of decan-9-yl acrylate (content ratio is 1:1 by molar ratio), 65 parts by mass of 2-ethylhexyl acrylate, and 111 parts by mass of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a mixed solution obtained by dissolving 27 parts by mass of 2,2-azobis(2,4-dimethylvaleronitrile) in 210 parts by mass of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was maintained at the same temperature for 5.5 hours and then cooled to room temperature, to obtain a copolymer (resin B2) solution having a B-type viscosity (23°C) of 43 mPas, a solid content of 29.8% by mass, and an acid value based on solid content of 148 mg-KOH / g (hereinafter sometimes referred to as resin solution (B2)). The weight average molecular weight Mw of the obtained copolymer was 1.09×10 4 , and the dispersity (molecular weight distribution) was 2.25.

[0177] Synthesis Example 3 An appropriate amount of nitrogen was flowed into a 1 L flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the inside with a nitrogen atmosphere, 280 parts by mass of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C while stirring. Next, 38 parts by mass of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 289 parts by mass of a mixture of decan-8 and / or 9-yl acrylate and 125 parts by mass of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a mixed solution obtained by dissolving 33 parts by mass of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts by mass of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was maintained at the same temperature for 4 hours and then cooled to room temperature, to obtain a copolymer (resin B3) solution having a B-type viscosity (23°C) of 125 mPas, a solid content of 37.0% by mass, and an acid value based on solid content of 77 mg-KOH / g (hereinafter sometimes referred to as resin solution (B3)). The weight average molecular weight Mw of the obtained copolymer was 9200, and the dispersity (molecular weight distribution) was 2.08. Almost no absorption was observed for the obtained copolymer solution at 500 to 600 nm.

[0178] The polystyrene-based weight-average molecular weight Mw and number-average molecular weight Mn of the resins obtained in the above synthesis examples were measured using the GPC method under the following conditions. Equipment: HLC-8120GPC (manufactured by Tosoh Corporation) Column; TSK-GELG2000HXL Column temperature: 40°C Solvent; THF Flow rate: 1.0mL / min Test liquid solid content concentration: 0.001~0.01% by mass Injection volume: 50μL Detector; RI Calibration standard material ;TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0179] [Preparation of dispersion] Dispersions (A-1) to (A-8) were prepared by mixing the following components and thoroughly dispersing the pigment using a bead mill. The resins (B1) to (B3) used were the resin solutions (B1) to (B3) described above.

[0180] [Preparation of dispersion (A-1)] CI Pigment Green 58 14.9 parts Acrylic pigment dispersant 2.2 parts Resin (B1) 17.7 parts Propylene glycol monomethyl ether acetate 65.2 parts

[0181] [Preparation of dispersion (A-2)] CI Pigment Green 59 10.9 parts Acrylic pigment dispersant 4.1 parts Resin (B1) 9.1 parts Propylene glycol monomethyl ether acetate 75.2 parts

[0182] [Preparation of dispersion (A-3)] CI Pigment Yellow 150 12.1 parts Acrylic pigment dispersant 5.4 parts Resin (B1) 12.4 parts Propylene glycol monomethyl ether acetate 70.1 parts

[0183] Preparation of Dispersion (A-4) C.I. Pigment Green 58 14.0 parts Acrylic pigment dispersant 1.9 parts Resin (B2) 21.8 parts Propylene glycol monomethyl ether acetate 62.3 parts

[0184] Preparation of Dispersion (A-5) C.I. Pigment Green 59 14.0 parts Acrylic pigment dispersant 1.9 parts Resin (B2) 21.8 parts Propylene glycol monomethyl ether acetate 62.3 parts

[0185] Preparation of Dispersion (A-6) C.I. Pigment Yellow 150 12.1 parts Acrylic pigment dispersant 5.4 parts Resin (B2) 14.1 parts Propylene glycol monomethyl ether acetate 68.4 parts

[0186] Preparation of Dispersion (A-7) C.I. Pigment Green 58 14.0 parts Acrylic pigment dispersant 1.9 parts Resin (B3) 17.6 parts Propylene glycol monomethyl ether acetate 66.5 parts

[0187] Preparation of Dispersion (A-8) C.I. Pigment Yellow 185 8.1 parts Acrylic pigment dispersant 5.3 parts Resin (B3) 7.7 parts Propylene glycol monomethyl ether acetate 78.9 parts

[0188] Examples 1-6 and Comparative Examples 1-2 [Preparation of colored resin composition] A colored resin composition was obtained by mixing the components listed in Table 8.

[0189] [Table 8]

[0190] The components listed in Table 8 are as follows. The amounts shown in the table refer to the amounts used for each component. Dispersion (A-1) to (A-8): Dispersion prepared as described above Resin (B1): Copolymer solution obtained in Synthesis Example 1 Resin (B2): Copolymer solution obtained in Synthesis Example 2 (component containing cyclic ether structure) Resin (B3): Copolymer solution obtained in Synthesis Example 3 (component containing cyclic ether structure) Polymerizable compound (C1) (cyclic ether structure (epoxy group) containing component): 1,2-epoxy-4-(2-oxyranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol (EHPE3150; manufactured by Daicel Corporation, 50% solids propylene glycol monomethyl ether acetate solution) Polymerizable compound (C1): Dipentaerythritol polyacrylate (A-9570W; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) Polymerization initiator (D): Irgacure® OXE-03; manufactured by BASF; compound represented by formula (d1-24).

[0191] [ka]

[0192] Solvent (E): Propylene glycol monomethyl ether acetate Leveling agent (F): Polyether-modified silicone oil (SH8400; manufactured by Toray Dow Corning Co., Ltd., propylene glycol monomethyl ether acetate solution with 10% solids content)

[0193] [Pattern creation] A colored resin composition was applied to a 2-inch square glass substrate (Eagle XG; Corning Corporation) by spin coating, and then pre-baked at 100°C for 3 minutes. After cooling, the substrate coated with the colored resin composition was placed at a distance of 100 μm from a quartz glass photomask with a pattern, and exposed using an exposure unit (TME-150RSK; Topcon Corporation) under an atmospheric atmosphere at a concentration of 150 mJ / cm². 2 The surface was irradiated with light at the specified exposure level (based on 365 nm). A mask with a 50 μm line and space pattern was used as the photomask. After light irradiation, the coating was developed by immersion in an aqueous developer containing 0.12% nonionic surfactant and 0.04% potassium hydroxide at 24°C for 60 seconds. After rinsing with water, post-baking was performed in an oven at 230°C for 30 minutes to obtain the pattern.

[0194] [Film thickness measurement] The film thickness FT (μm) of the obtained patterns was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.). The patterns obtained in Examples 1-4 and Comparative Examples 1 and 2 had x and y values ​​of 0.270 and 0.638 in the XYZ color system, respectively. The pattern obtained in Example 5 had x and y values ​​of 0.214 and 0.638 in the XYZ color system, respectively. The pattern obtained in Example 6 also had x and y values ​​of 0.270 and 0.638 in the XYZ color system. The results are shown in Table 8.

[0195] [Measurement of dielectric loss tangent (tanδ)] The dielectric loss tangent was measured using the following method. First, a colored resin composition was applied by spin coating to a glass substrate (resistance: 10Ω) on which a transparent conductive film (ITO film) had been formed, and pre-baked at 100°C for 3 minutes. After cooling, the glass substrate coated with this colored resin composition was exposed to 80 mJ / cm² in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). 2The surface was irradiated with light at an exposure level of 365 nm (based on 365 nm) and post-baked at 230°C for 30 minutes. A Pd / Pt-based deposition material was deposited onto the coating using a magnetron sputtering apparatus (MSP-1S: manufactured by Vacuum Device Co., Ltd.) to a diameter of 1.5 cm, creating an electrode section. One drop of silver-based conductive paint (TreeBond 3350C) was dropped onto the center of the electrode section, and then dried at 100°C for 3 minutes to obtain a measurement substrate. The illuminance of the surface irradiated from the opposite side of the coating surface of this measurement substrate was 2.8 × 10⁻¹⁴. 5 The coating surface was illuminated with light under conditions of lux (lx), and the dielectric loss tangent value at a frequency of 20 Hz was measured using an LCR meter / impedance analyzer (Precision Component Analyzer 6440B; manufactured by Wayne Kerr Electronics). [Industrial applicability]

[0196] The colored resin composition of the present invention can be suitably used in the manufacture of color filters, display devices, and solid-state image sensors.

Claims

1. A colored resin composition comprising at least a coloring agent and a cyclic ether structure-containing component, The cyclic ether structure-containing component includes a resin having a cyclic ether structure and a polymerizable compound having a cyclic ether structure (however, the polymerizable compound does not include those having repeating structural units within the molecule and having a weight-average molecular weight of 3000 or more). The resin having the cyclic ether structure is a copolymer containing structural units derived from monomers having an oxyranyl group and an ethylenically unsaturated bond, and having a weight-average molecular weight of 3000 or more. The polymerizable compound having the cyclic ether structure is a compound having an oxirane ring, The coloring agent contains at least a green coloring agent, and the total coloring agent content is 45.5% by mass or more relative to the solid content of the colored resin composition. A colored resin composition characterized in that the content of the green coloring agent is 60% by mass or more and 95% by mass or less of the total solid content of the coloring agent.

2. The colored resin composition according to claim 1, wherein the resin having the cyclic ether structure comprises a resin having a solid content acid value of 85 mg-KOH / g or more.

3. The colored resin composition according to claim 1 or 2, wherein the content of the green coloring agent is 60% by mass or less relative to the solid content of the colored resin composition.

4. The colored resin composition according to any one of claims 1 to 3, wherein the green coloring agent is zinc phthalocyanine.

5. The colored resin composition according to any one of claims 1 to 4, wherein the coloring agent further comprises a yellow coloring agent.

6. The colored resin composition according to any one of claims 1 to 5, wherein the content of the cyclic ether structure-containing component is 0.1% by mass or more and 40% by mass or less with respect to the solid content of the colored resin composition.

7. A colored coating film is formed from the aforementioned colored resin composition such that the film thickness after post-baking at 230°C for 30 minutes is 1 to 4 μm, and this is 2.8 × 10 5 A colored resin composition according to any one of claims 1 to 6, wherein the dielectric loss tangent tanδ at a frequency of 20 Hz is 0.20 or less when illuminated with an illuminance of lux (lx).

8. A color filter formed from a colored resin composition according to any one of claims 1 to 7.

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

10. A solid-state image sensor including the color filter described in claim 8.

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