Coloring curable resin composition, color filter, and display device

Abstract

To provide a colored curable resin composition capable of forming a color filter having haze without adding inorganic fine particles.SOLUTION: The coloring composition comprises a colorant, a resin, a polymerizable compound, a polymerization initiator and a solvent, wherein the polymerizable compound comprises a monofunctional monomer and a polyfunctional monomer, and the monofunctional monomer is represented by formula (1): wherein R1 represents a hydrogen atom or a methyl group, and R2 represents a linear or branched alkyl group having 7 to 22 carbon atoms. The coloring curable resin composition according to claim 1.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] A color filter substrate has a structure in which a black matrix layer and color filters, for example, red (R), green (G), and blue (B), for forming each pixel are formed on a transparent substrate, and in some cases a protective film is laminated on top of them, and is used in liquid crystal display devices, organic electroluminescence (EL) display devices, etc. Such display devices are required to have a sufficient field of view even when viewed from an oblique angle, and for example, Patent Document 1 discloses a colored curable resin composition that contains inorganic fine particles and can form a color filter that can provide a good field of view from an oblique angle. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2023-081304 Summary of the Invention [Problem to be solved by the invention]

[0004] Conventionally known colored curable resin compositions use inorganic fine particles to scatter light transmitted through the display device in all directions, thereby averaging the light in the field of view and widening the viewing angle. However, in compositions that can form color filters with haze by using inorganic fine particles, the scattering effect can be reduced due to the non-uniform dispersion of the inorganic fine particles caused by sedimentation of the inorganic fine particles. Therefore, there is a demand for color filters formed from colored curable resin compositions that further ensure a wide field of view when the display device is viewed obliquely.

[0005] Therefore, an object of the present invention is to provide a colored curable resin composition that can form a color filter having haze without adding inorganic fine particles. [Means for solving the problem]

[0006] The present inventors have found that the above object can be achieved by the colored curable resin composition of the present invention, which will be described below. That is, the present invention includes the following aspects. [1] A composition comprising a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent; the polymerizable compound includes a monofunctional monomer and a polyfunctional monomer, The monofunctional monomer is represented by the formula (1): [ka] [In the formula, R 1 represents a hydrogen atom or a methyl group, R 2 represents a linear or branched alkyl group having 7 to 22 carbon atoms.] A colored curable resin composition comprising a compound represented by the formula: [2] The colored curable resin composition according to [1], wherein the resin content is 15 to 50 mass % based on the solid content of the colored curable resin composition. [3] The colored curable resin composition according to [1] or [2], wherein the content of the monofunctional monomer represented by formula (1) is 40 to 250 parts by mass per 100 parts by mass of the resin. [4] The colored curable resin composition according to any one of [1] to [3], wherein the content of the monofunctional monomer represented by formula (1) is 150 to 700 parts by mass relative to 100 parts by mass of the polyfunctional monomer. [5] A color filter which is a cured film of the colored curable resin composition according to any one of [1] to [4]. [6] The color filter according to [5], which has a haze value of 1 to 50% when converted into a color filter having a thickness of 2.5 μm. [7] A display device comprising the color filter according to [5] or [6]. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a colored curable resin composition that can form a color filter having haze without adding inorganic fine particles. DETAILED DESCRIPTION OF THE INVENTION

[0008] Hereinafter, embodiments of the present invention will be described in detail. Note that the scope of the present invention is not limited to the embodiments described herein, and various modifications can be made without departing from the spirit of the present invention. Furthermore, when multiple upper and lower limit values ​​are listed for a specific parameter, any of these upper and lower limit values ​​can be combined to form a suitable numerical range.

[0009] <Colored curable resin composition> The colored curable resin composition of the present invention contains a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent, and the polymerizable compound contains a monofunctional monomer and a polyfunctional monomer.

[0010] (polymerizable compound) In this specification, the polymerizable compound refers to a compound that can be polymerized by an active radical and / or an acid generated from a polymerization initiator, and examples thereof include a compound having a polymerizable ethylenically unsaturated bond. The polymerizable compound in the colored curable resin composition of the present invention includes a monofunctional monomer and a polyfunctional monomer.

[0011] The monofunctional monomer contained in the polymerizable compound in the colored curable resin composition of the present invention is Formula (1): [ka] [In the formula, R 1 represents a hydrogen atom or a methyl group, R 2 represents a linear or branched alkyl group having 7 to 22 carbon atoms.] The present invention includes compounds represented by the formula:

[0012] Conventionally, inorganic fine particles have been used to impart haze to color filters, as described in Patent Document 1, for example, but problems can arise due to the settling of the inorganic fine particles. In contrast, the colored curable resin composition of the present invention contains a compound represented by formula (1) (hereinafter sometimes referred to as the "monofunctional monomer of formula (1)"), so that a color filter having a desired haze can be formed without adding inorganic fine particles.

[0013] R in Equation (1) 2 has 7 to 22 carbon atoms. 2 When the number of carbon atoms in R is within the above range, a colored curable resin composition capable of forming a color filter having a desired haze can be obtained. 2 When the number of carbon atoms in R in formula (1) is large, the monofunctional monomer of formula (1) is less likely to volatilize if it remains in the cured film as an unreacted product, and therefore, volatile components (outgassing) that may cause display defects are less likely to be produced. 2 When the carbon number of R is large, the haze of the film can be ensured with a smaller amount than when the carbon number of R is small, which is advantageous for reliability such as chemical resistance. 2 If the number of carbon atoms in is too large, the surface condition of the cured film tends to become rough. 2 The number of carbon atoms is preferably 7 to 20, and more preferably 10 to 20.

[0014] In formula (1), R 2 Preferred branched alkyl groups in the above formula are a 2-ethylhexyl group, a 2-hexyldecyl group, and a 2-butyloctyl group.

[0015] Furthermore, from the viewpoint of high reactivity in radical polymerization, R 1 is preferably a hydrogen atom.

[0016] In one embodiment of the present invention, examples of the monofunctional monomer of formula (1) include heptyl acrylate, octyl acrylate, isononyl acrylate, dodecyl acrylate, isodecyl acrylate, hexadecyl acrylate, stearyl acrylate, isostearyl acrylate, docosyl acrylate, dodecyl methacrylate, and 2-ethylhexyl acrylate. When the monofunctional monomer of formula (1) exemplified above is contained, the desired haze in the color filter is ensured, and further, a good surface state of the cured film is easily obtained, and chemical resistance and the like also tend to be excellent. The colored curable resin composition of the present invention may contain one type of monofunctional monomer of formula (1), or may contain two or more types of monofunctional monomers of formula (1) in combination.

[0017] The content of the monofunctional monomer of formula (1) in the colored curable resin composition may be appropriately selected depending on the combination of polyfunctional monomers and / or resins contained in the colored curable resin composition. As described above, the content of the monofunctional monomer of formula (1) in the colored curable resin composition is determined by the R 2 When the content of the monofunctional monomer of formula (1) is small, the polyfunctional monomer and resin component can be contained in larger amounts, which can be advantageous in that it is easy to adjust the curability of the composition and to easily obtain a good cured film shape and reliability such as chemical resistance.

[0018] In one embodiment, the content of the monofunctional monomer of formula (1) is preferably 12 to 45 mass%, more preferably 15 to 40 mass%, and even more preferably 18 to 35 mass%, based on the solid content of the colored curable resin composition. When the content of the monofunctional monomer of formula (1) is within the above range, the desired haze in the color filter is easily obtained. Furthermore, reliability such as high chemical resistance is easily obtained. In this specification, the "solid content" refers to the amount obtained by excluding the solvent content from the total amount of the colored curable resin composition. The solid content and the content of each component relative to the solid content can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0019] The colored curable resin composition of the present invention may contain, as a polymerizable compound, a monofunctional monomer other than that represented by formula (1) (hereinafter, sometimes referred to as "other monofunctional monomers"). Examples of other monofunctional monomers include aliphatic monofunctional monomers (excluding the monofunctional monomer represented by formula (1)), aromatic monofunctional monomers, and epoxy group-containing monofunctional monomers. Among these, aliphatic monofunctional monomers and aromatic monofunctional monomers are preferred because they facilitate the adjustment of the desired haze. The aliphatic monofunctional monomer may be a linear, branched, or alicyclic monofunctional monomer. Examples of the aliphatic monofunctional monomer include hexyl (meth)acrylate, cyclohexyl (meth)acrylate, and tricyclodecyl (meth)acrylate; and examples of the aromatic monofunctional monomer include phenyl (meth)acrylate and benzyl (meth)acrylate. The colored curable resin composition of the present invention may contain one type of other monofunctional monomer, or may contain two or more types of other monofunctional monomers in combination.

[0020] When the colored curable resin composition of the present invention contains other monofunctional monomers, the content of the other monofunctional monomers can be appropriately adjusted depending on the type of each monofunctional monomer used, but the content of the other monofunctional monomers is preferably 50 parts by mass or less, more preferably 20 parts by mass or less, relative to 100 parts by mass of the monofunctional monomer of formula (1). The lower limit of the content of the other monofunctional monomers is not particularly limited, but is usually 1 part by mass relative to 100 parts by mass of the monofunctional monomer of formula (1).

[0021] The polyfunctional monomer contained in the polymerizable compound in the colored curable resin composition of the present invention can be, for example, one having two or more ethylenically unsaturated bonds, and preferably one having three or more ethylenically unsaturated bonds. Examples of such polyfunctional monomers include glycerin triacrylate, 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 nona(meth)acrylate. acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate. As the polyfunctional monomer, only one type may be used, or two or more types may be used in combination.

[0022] From the viewpoint of easily obtaining a desired haze when combined with the monofunctional monomer of formula (1), the polyfunctional monomer is preferably, for example, a chain-type aliphatic polyfunctional monomer. Furthermore, the polyfunctional monomer preferably has 3 to 6 ethylenically unsaturated bonds. When the polyfunctional monomer has 3 to 6 ethylenically unsaturated bonds, it is easy to obtain a desired haze in the color filter when combined with the monofunctional monomer of formula (1), and further, high curability and a good cured film shape are easily obtained. Among the above polyfunctional monomers, glycerin triacrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate are particularly preferred.

[0023] The weight-average molecular weight of the polyfunctional monomer is preferably 150 to 2,900, more preferably 250 to 1,500, from the viewpoint of easily obtaining a desired haze when combined with the monofunctional monomer of formula (1). Furthermore, when the weight-average molecular weight of the polyfunctional monomer is within the above range, it is easy to obtain a good cured film shape and to adjust the curability of the colored curable resin composition to an appropriate range. The weight-average molecular weight (Mw) can be measured, for example, using gel permeation chromatography (GPC). More specifically, it can be measured by the method described in the Examples below.

[0024] The content of the polyfunctional monomer is preferably 1 to 50 mass%, more preferably 3 to 45 mass%, and even more preferably 5 to 30 mass%, based on the solid content of the colored curable resin composition. When the content of the polyfunctional monomer is within the above range, the desired haze is easily obtained in the color filter. Furthermore, when a coating film of the colored curable resin composition is exposed to light and cured, the degree of curing within the coating film is less likely to vary, and sufficient curing can be achieved particularly deep into the coating film, making it easier to obtain a good cured film.

[0025] The content of the monofunctional monomer of formula (1) is preferably 150 to 700 parts by mass, more preferably 150 to 650 parts by mass, even more preferably 170 to 650 parts by mass, and particularly preferably 180 to 500 parts by mass, relative to 100 parts by mass of the polyfunctional monomer. When the content of the monofunctional monomer of formula (1) is within the above range relative to 100 parts by mass of the polyfunctional monomer, a colored curable resin composition capable of forming a color filter having a desired haze can be obtained.

[0026] The content of the monofunctional monomer of formula (1) relative to 100 parts by mass of the polyfunctional monomer is determined by the ratio of R 2 The carbon number of the R 2 The larger the number of carbon atoms in R in the monofunctional monomer of formula (1), the more likely it is that a desired haze can be obtained with a smaller content of the monofunctional monomer of formula (1). 2When the carbon number is 12 to 20, the content is preferably 150 to 450 parts by mass relative to 100 parts by mass of the polyfunctional monomer, which makes it easier to obtain the desired haze in the color filter.

[0027] The content of the polymerizable compound is preferably 10 to 60 mass%, more preferably 15 to 50 mass%, and even more preferably 20 to 45 mass%, based on the solid content of the colored curable resin composition. When the content of the polymerizable compound is within the above range, the desired haze in the color filter is easily obtained. Furthermore, when a coating film of the colored curable resin composition is exposed to light and cured, the degree of curing within the coating film is less likely to vary, and sufficient curing can be achieved particularly deep into the coating film, making it easier to obtain a good cured film.

[0028] (resin) The resin contained in the colored curable resin composition of the present invention is not particularly limited, but is preferably one that can obtain the desired haze when combined with the monofunctional monomer of formula (1), and is preferably an alkali-soluble resin. In this specification, the alkali-soluble resin refers to a resin that has the property of dissolving in a developer, which is an aqueous solution of an alkaline compound. Specific examples include resins having a carboxy group and / or a phenolic hydroxyl group, and preferably a resin having a carboxy group. The alkali-soluble resin can be appropriately selected from resins conventionally known in the art, and may be used alone or in combination of two or more.

[0029] In one embodiment of the present invention, examples of the alkali-soluble resin include the following resins [K1] to [K6].

[0030] Resin [K1]: a copolymer having structural units derived from at least one member (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure and an ethylenically unsaturated bond having 2 to 4 carbon atoms; Resin [K2]: a copolymer having structural units derived from (a), structural units derived from (b), and structural units derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, sometimes referred to as "(c)"); Resin [K3]: a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]: a copolymer having a structural unit derived from (a) to which (b) has been added, and a structural unit derived from (c); Resin [K5]: a copolymer having a structural unit derived from (b) to which (a) has been added and a structural unit derived from (c); Resin [K6]: A copolymer having structural units derived from (c) and structural units obtained by adding (a) to structural units derived from (b) and further adding polycarboxylic acid and / or carboxylic acid anhydride.

[0031] Specifically, (a) includes, for example: Unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among these, acrylic acid, methacrylic acid, etc. are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in an alkaline aqueous solution.

[0032] (b) refers to, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

[0033] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").

[0034] Examples of (b1) include a monomer (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.

[0035] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0036] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (BI), and compounds represented by formula (BII).

[0037] [ka] [In formula (BI) and formula (BII), Ra and R b represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X 1 and X 2 is a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g represents -NH-. R g represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0038] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R a and R b Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0039] 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 2Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).

[0040] Specific examples of the compound represented by formula (BI) include compounds represented by formulas (BI-1) to (BI-15), preferably compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9), and (BI-11) to (BI-15), and more preferably compounds represented by formulas (BI-1), (BI-7), (BI-9), and (BI-15).

[0041] [ka]

[0042] [ka]

[0043] Specific examples of the compound represented by formula (BII) include compounds represented by formulas (BII-1) to (BII-15), preferably compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15), more preferably compounds represented by formulas (BII-1), (BII-7), (BII-9), and (BII-15).

[0044] [ka]

[0045] [ka]

[0046] The compound represented by formula (BI) and the compound represented by formula (BII) can be used alone. They can be used in combination at any ratio. When used in combination, the mixing ratio of formula (BI):formula (BII) [molar ratio] is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

[0047] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like.

[0048] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0049] In the case of resin [K1] or resin [K2], (b) is preferably (b1) in that the reliability of the heat resistance, chemical resistance, etc. of the resulting color filter can be improved.

[0050] Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0] 2,6 ]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters such as ]decen-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the technical field), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene Bicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene 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; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide; Examples 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, and 2,3-dimethyl-1,3-butadiene. Of these, (meth)acrylic acid esters are preferred.

[0051] In the resin [K1], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: When the ratio of the structural units of the resin [K1] is within the above range, it is believed that the desired haze in the color filter is easily obtained when combined with the monofunctional monomer of formula (1). In addition, the colored curable resin composition tends to have excellent storage stability, developability when forming a pattern, and solvent resistance of the resulting cured film.

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

[0053] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, followed by heating and keeping the temperature while stirring. The polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, etc.). Solvents that dissolve the respective monomers are sufficient, and examples of organic solvents that may be optionally contained in the colored curable resin composition of the present invention include the solvents described below.

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

[0055] In the resin [K2], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 45 mol% Structural units derived from (b): 2 to 95 mol% Structural units derived from (c): 1 to 65 mol% Preferably, Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 80 mol% Structural units derived from (c): 5 to 60 mol% It is more preferable that: When the ratio of the structural units of the resin [K2] is within the above range, it is believed that the desired haze in the color filter is easily obtained when combined with the monofunctional monomer of formula (1). In addition, the colored curable resin composition tends to have excellent storage stability, developability when forming a pattern, and the resulting cured film tends to have excellent solvent resistance, heat resistance, and mechanical strength.

[0056] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0057] In the resin [K3], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that: Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

[0058] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].

[0059] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.), a polymerization inhibitor (e.g., hydroquinone, methoquinone, etc.), etc. are placed in the flask, and the reaction is carried out, for example, at 60 to 130°C for 1 to 10 hours, thereby producing the resin [K4]. The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By using (b) in this range, it is believed that the desired haze in a color filter can be easily obtained when combined with the monofunctional monomer of formula (1). Furthermore, the colored curable resin composition tends to have a good balance of storage stability, developability when forming a pattern, pattern shape, low-temperature curability, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern. Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K4], and (b1-1) is even more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

[0060] Resin [K5] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that: When the ratio of the structural units of the resin [K5] is within the above range, it is believed that a desired haze in a color filter can be easily obtained when combined with the monofunctional monomer of formula (1). In addition, the colored curable resin composition tends to have a good balance of storage stability, developability when forming a pattern, pattern shape, low-temperature curability, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern.

[0061] Furthermore, under the same conditions as in the production method of resin [K4], resin [K5] can be obtained by reacting the cyclic ether derived from (b) contained in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used to react with the copolymer is preferably 5 to 100 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.

[0062] Resin [K6] is a resin obtained by further reacting resin [K5] with a polycarboxylic acid and / or a carboxylic anhydride. The hydroxyl group generated by the reaction of the cyclic ether derived from (b) with the carboxylic acid or carboxylic anhydride derived from (a) is further reacted with a polycarboxylic acid and / or a carboxylic anhydride. Examples of polycarboxylic acids include oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, and tricarbanilic acid. Examples of carboxylic acid anhydrides include succinic anhydride, 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. The amount of polycarboxylic acid and / or carboxylic acid anhydride used is preferably 0.05 to 1 mol, and more preferably 0.1 to 0.5 mol, per 1 mol of (a) used.

[0063] As the resin contained in the colored curable resin composition of the present invention, from the viewpoint of good developability and low-temperature curability, a resin having a structural unit having an ethylenically unsaturated bond in a side chain (for example, resin [K4], resin [K5], or resin [K6]) is preferred, and a resin having a structural unit containing a (meth)acryloyl group in a side chain is more preferred. As the resin having a structural unit containing a (meth)acryloyl group in the side chain, for example, resin [K4] using a monomer having a (meth)acryloyl group as (b), such as glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3-methyl-3-methacryloyloxymethyloxetane, or tetrahydrofurfuryl acrylate, and resin [K5] and resin [K6] using a monomer having a (meth)acryloyl group as (a), such as acrylic acid, methacrylic acid, or succinic acid mono[2-(meth)acryloyloxyethyl], are preferred. In the resins [K4], [K5] and [K6], (c) is preferably a (meth)acrylic acid ester.

[0064] Furthermore, when the resin contained in the colored curable resin composition of the present invention is resin [K4], resin [K5], or resin [K6] (having a structural unit containing a (meth)acryloyl group in the side chain), it is considered that the desired haze in the color filter is easily obtained when combined with the monofunctional monomer of formula (1). Among the above, resin [K4] is particularly preferred.

[0065] The polystyrene-equivalent weight-average molecular weight of the resin contained in the colored curable resin composition of the present invention is preferably 3,000 to 100,000, more preferably 4,000 to 50,000, and even more preferably 5,000 to 30,000. When the weight-average molecular weight of the resin is within the above range, the hardness of the cured film of the composition of the present invention is improved, the residual film rate is high, and the solubility of the unexposed area in the developer is good, which tends to improve the pattern shape and pattern resolution. Furthermore, it is presumed that when combined with the monofunctional monomer of formula (1), the desired haze in the color filter is easily obtained.

[0066] The polydispersity of the resin [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

[0067] The acid value of the resin is preferably 10 to 170 mgKOH / g, more preferably 15 to 150 mgKOH / g, and even more preferably 20 to 135 mgKOH / g, calculated as solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin, and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0068] The resin content is preferably 15 to 50 mass %, more preferably 20 to 45 mass %, and even more preferably 25 to 40 mass %, based on the solid content of the colored curable resin composition. When the resin content is within the above range, a desired haze in the color filter is easily obtained, the curability of the colored curable resin composition is easily increased, a cured film is easily formed, and the pattern resolution and film remaining rate tend to be improved.

[0069] When the total mass of the resin and polymerizable compound contained in the colored curable resin composition is taken as 100 mass%, the content of the polymerizable compound is preferably 75 mass% or less, more preferably 65 mass% or less, even more preferably 60 mass% or less, and even more preferably 50 mass% or less. When the content of the polymerizable compound is within the above range, a desired haze in the color filter is easily obtained. When the content of the polymerizable compound is equal to or less than the above upper limit, when a coating film of the colored curable resin composition is exposed to light and cured, the degree of curing within the coating film is less likely to vary, and sufficient curing can be achieved particularly deep into the coating film, making it easier to obtain a good cured film shape.

[0070] The content of the monofunctional monomer of formula (1) is preferably 40 to 250 parts by mass, more preferably 45 to 200 parts by mass or 50 to 250 parts by mass, and even more preferably 50 to 150 parts by mass, relative to 100 parts by mass of the resin. When the content of the monofunctional monomer of formula (1) is within the above range, a color filter having haze is easily obtained.

[0071] (Polymerization initiator) A polymerization initiator is a compound that generates active radicals, acids, etc. under the action of light or heat, thereby initiating polymerization. Examples of the polymerization initiator include, but are not limited to, O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds. Of these, O-acyloxime compounds are preferred. From the viewpoint of easily improving the curability of the colored curable resin composition, the polymerization initiator preferably has a maximum absorption wavelength in the range of 365 to 390 nm, more preferably in the range of 370 to 390 nm. The colored curable resin composition of the present invention may contain one type of polymerization initiator, or may contain two or more types of polymerization initiators.

[0072] The polymerization initiator is preferably an O-acyloxime compound, and is also preferably a compound having a nitro group.

[0073] The O-acyloxime compound has the formula (c1): [ka] It is a compound having a structure represented by the following formula: In the following, * represents a bond.

[0074] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N- Examples thereof include acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one. Commercially available products such as Irgacure OXE01, OXE02, and OXE03 (all manufactured by BASF), N-1919, NCI-730, NCI-831, and NCI-930 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, and PBG-329 (all manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used.Among them, the O-acyloxime compound is preferably at least one selected from the group consisting of N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine. These O-acyloxime compounds tend to produce color filters with high brightness.

[0075] The alkylphenone compound is a compound having a partial structure represented by formula (d4) or (d5). In these partial structures, the benzene ring may have a substituent.

[0076] [ka]

[0077] Examples of compounds having a 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, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used. Examples of compounds having a 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-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. In terms of sensitivity, the alkylphenone compound is preferably a compound having a structure represented by formula (d4).

[0078] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and the like. Examples of suitable biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B No. 48-38403 and JP-A No. 62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A No. 7-10913). Among these, compounds represented by the following formula and mixtures thereof are preferred:

[0079] [ka]

[0080] 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-(

[0033] 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0081] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

[0082] The content of the polymerization initiator is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, even more preferably 1 to 12 parts by mass, and particularly preferably 1 to 8 parts by mass, relative to 100 parts by mass of the total amount of the resin and polymerizable compound contained in the colored curable resin composition. When the content of the polymerization initiator is within the above range, a pattern with a good shape can be easily formed by exposure and development, and curing properties at low temperatures can be easily improved. In addition, the sensitivity is increased, and exposure time tends to be shortened, thereby improving productivity of color filters and the like.

[0083] (coloring agent) The colored curable resin composition of the present invention contains at least one colorant. The colored curable resin composition of the present invention containing at least one colorant can be suitably used as a colored curable resin composition for forming a resist layer in a color filter. Furthermore, the colored curable resin composition of the present invention having the above-described composition can be darkened when used as a color resist composition, making it easy to achieve a desired color. The colorant may be either a dye or a pigment, but preferably contains a pigment. Known pigments can be used as the pigment, and examples include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0084] Specifically, yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231, 235, and 236; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 272, 273, 291, 297; Blue pigments such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 37, 38; Green pigments of CI Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, 67; Brown pigments such as CI Pigment Brown 23 and 25; Examples include black pigments such as CI Pigment Black 1, 7, 31, and 32.

[0085] The pigment may be subjected, as necessary, to a rosin treatment, a surface treatment using a pigment derivative into which an acidic group or a basic group has been introduced, a graft treatment onto the pigment surface using a polymer compound or the like, a microparticle treatment using a sulfuric acid microparticle method or the like, a washing treatment using an organic solvent or water to remove impurities, a treatment to remove ionic impurities using an ion exchange method or the like, or the like. The pigment preferably has a uniform particle size. Furthermore, by adding a pigment dispersant and carrying out a dispersion treatment, a pigment dispersion liquid in which the pigment is uniformly dispersed in the solution can be obtained.

[0086] Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of the pigment dispersant include trade names such as KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Lubrizol Corporation), EFKA (manufactured by CIBA), AJISPER (manufactured by Ajinomoto Fine-Techno Co., Ltd.), and Disperbyk (manufactured by BYK-Chemie).

[0087] When a pigment dispersant is used, the amount used is preferably 1% by mass or more and 100% by mass or less, and more preferably 5% by mass or more and 50% by mass or less, based on the total amount of pigment. When the amount of pigment dispersant used is within this range, a pigment dispersion in a uniformly dispersed state tends to be obtained.

[0088] The content of the pigment in the colorant is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 90% by mass or more, particularly preferably 95% by mass or more, and may be 100% by mass.

[0089] The colorant may contain a dye. The dye is not particularly limited and any known dye can be used, including solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as non-pigment dyes with hues in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in Dyeing Notes (Shikisensha). Further, based on chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Among these, organic solvent-soluble dyes are preferred.

[0090] Specifically, CI Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, and 35; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 177, 178, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 23 82, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 388, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 1 23, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324, 335, 340; CI Acid Dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, and 82; CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, and 60, CI Basic Red 1, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic Red 9; CI Basic dyes such as CI Basic Green 1, CI Reactive Yellow 2,76,116; CI Reactive Orange 16; CI reactive dyes such as CI Reactive Red 36, CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Mordant dyes such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, and 53; Examples include CI Vat dyes such as CI Vat Green 1.

[0091] The content of the dye in the colorant is preferably 50% by mass or less, more preferably 30% by mass or less, even more preferably 10% by mass or less, particularly preferably 5% by mass or less, and may be 0% by mass.

[0092] The content of the colorant is preferably 5 to 60 mass%, more preferably 8 to 55 mass%, and even more preferably 10 to 50 mass%, based on the solid content of the colored curable resin composition. When the content of the colorant is within the above range, the color density when made into a color filter is sufficient, and since the necessary amount of colored curable resin can be contained in the composition, a cured film with sufficient mechanical strength can be formed.

[0093] In colored curable resin compositions that are particularly required to be deeply colored, the colorant content is preferably 15 to 60 mass %, more preferably 18 to 55 mass %, and even more preferably 20 to 50 mass %, based on the solid content of the colored curable resin composition. When the colorant content is within this range, a particularly high color density can be achieved when made into a color filter, and since the necessary amount of curable resin can be contained in the composition, a cured film with sufficient mechanical strength can be formed.

[0094] (Polymerization initiator aid) The colored curable resin composition of the present invention may further contain at least one polymerization initiation aid. The polymerization initiation aid is a compound used to promote polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator, or a sensitizer. When a polymerization initiation aid is contained, it is usually used in combination with a polymerization initiator. Examples of the polymerization initiator aid include 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, and N-phenylglycine.

[0095] When these polymerization initiation aids are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin and the polymerizable compound. When the amount of the polymerization initiation aid is within this range, patterns can be formed with higher sensitivity during exposure, and the productivity of color filters and the like tends to improve.

[0096] (solvent) The colored curable resin composition of the present invention may further contain at least one solvent. The solvent is not particularly limited, and solvents commonly used in the relevant field can be used. Examples include ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, or -COO-), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide.

[0097] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0098] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

[0099] Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, and 2-ethoxy-2-methylpropionate. ethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

[0100] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, diacetone alcohol, and isophorone.

[0101] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0102] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0103] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0104] The solvent preferably includes one or more solvents selected from the group consisting of ether solvents, ether ester solvents, and ketone solvents, more preferably includes an ether solvent and an ether ester solvent, and even more preferably includes propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate.

[0105] The solvent content is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, relative to the total amount of the colored curable resin composition of the present invention. In other words, the solid content of the colored curable resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the solvent content is within the above range, the flatness during application is good, and further, when a color filter is formed, for example, the color density is not insufficient, so that the display characteristics tend to be good.

[0106] (Leveling agent) The colored curable resin composition of the present invention may further contain at least one leveling agent. Examples of the leveling agent include silicone surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms. These may have a polymerizable group in the side chain.

[0107] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule, such as Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade names: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).

[0108] Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule, such as Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), Ftop (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by AGC Corporation (formerly Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemical Research Institute, Ltd.).

[0109] Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0110] When a leveling agent is contained, the content of the leveling agent is preferably 0.0005 to 0.5 mass%, more preferably 0.001 to 0.2 mass%, relative to the total amount of the colored curable resin composition. This content does not include the content of the pigment dispersant. When the content of the leveling agent is within the above range, the flatness of the cured film of the colored curable resin composition of the present invention used for color filters and the like can be improved.

[0111] (Other ingredients) The colored curable resin composition of the present invention may contain additives known in the technical field, such as other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as needed.

[0112] <Method for producing colored curable resin composition> The colored curable resin composition of the present invention can be prepared, for example, by mixing a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent, as well as a polymerization initiator aid, a leveling agent, and other components that are used as needed. The colorant may be prepared using the pigment dispersion liquid described above. The target curable resin composition can be prepared by mixing the remaining components with the pigment dispersion liquid to a predetermined concentration. Furthermore, it is preferable to filter the curable resin composition after mixing through a filter with a pore size of about 0.01 to 10 μm.

[0113] The colored curable resin composition of the present invention allows for the formation of a color filter having haze without the addition of inorganic fine particles. Therefore, the colored curable resin composition does not require a step of stirring inorganic fine particles to uniformly disperse them in the composition, which is expected to improve productivity and has excellent storage stability. The content of inorganic fine particles in the colored curable resin composition of the present invention is, for example, 2% by mass or less, preferably 1.5% by mass or less, and more preferably 1% by mass or less, based on the solid content of the colored curable resin composition. In one embodiment of the present invention, the colored curable resin composition of the present invention is substantially free of inorganic fine particles. In this specification, "substantially" means that the content of inorganic fine particles is 0.1% by mass or less, based on the solid content of the colored curable resin composition.

[0114] <Color filter manufacturing method> Methods for producing a cured film such as a colored pattern from the colored curable resin composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography method is a method in which the colored curable resin composition is applied to a substrate and dried to form a colored composition layer, and the colored composition layer is exposed to light through a photomask and developed. In the photolithography method, a colored coating film, which is a cured film of the colored curable resin composition layer, can be formed by not using a photomask during exposure and / or not developing. The colored pattern or cured film such as a colored coating film formed in this way can be used as a color filter.

[0115] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or silica-coated soda lime glass, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. A separate color filter layer, a resin layer, a transistor, a circuit, or the like may be formed on these substrates.

[0116] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be produced as follows. First, a colored resin composition is applied onto a substrate, and then dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as solvents, thereby obtaining a smooth colored composition layer. Examples of the coating method include spin coating, slit coating, and slit and spin coating. The temperature when drying by heating is preferably 30 to 120° C., more preferably 50 to 110° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying is carried out under reduced pressure, it is preferable to carry out the drying under a pressure of 50 to 150 Pa at a temperature in the range of 20 to 25°C. The thickness of the colored composition layer is not particularly limited and may be appropriately selected depending on the desired thickness of the color filter.

[0117] When forming a pattern, the colored composition layer can be exposed to light through a photomask for forming a desired colored pattern, and then developed to form the pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended use is used. The light source used for exposure is preferably a light source that emits light with a wavelength of 250 to 450 nm. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples of light sources include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. Furthermore, the exposure dose based on a wavelength of 365 nm is 50 to 300 J / cm. 2 is preferably 60 to 200 J / cm 2 More preferably, it is 65 to 180 J / cm 2 It is more preferable that: It is preferable to use an exposure device such as a mask aligner or a stepper, since it is possible to uniformly irradiate the entire exposure surface with parallel light rays and to accurately align the photomask with the substrate on which the colored composition layer is formed.

[0118] A colored pattern is formed on the substrate by bringing the exposed colored composition layer into contact with a developer and developing it. The unexposed portions of the colored composition layer are dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Furthermore, the developer may contain a surfactant. The developing method may be any of a puddle method, a dipping method, a spray method, etc. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferable to wash with water.

[0119] Furthermore, it is preferable to post-bake the obtained colored pattern. In order to form a color filter to be used in an organic EL display device, the post-bake temperature may be 200°C or lower, but is preferably 170°C or lower, and more preferably 150°C or lower. In the present invention, it is preferable to perform post-bake at a lower temperature, for example, a temperature of 130°C or lower. The lower limit of the post-bake temperature is preferably 70°C or higher, and more preferably 75°C or higher. The post-bake time is preferably 1 to 120 minutes, and more preferably 5 to 60 minutes.

[0120] <Color filter> The present invention also provides a color filter that is a cured film of the colored curable resin composition of the present invention. The color filter of the present invention may be a cured film in which a pattern is formed in the colored curable resin composition of the present invention as described above.

[0121] The thickness of the cured film is not particularly limited and can be adjusted appropriately depending on the purpose and use, and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, more preferably 0.3 to 6 μm, and even more preferably 0.5 to 3 μm.

[0122] A color filter that is a cured film of the colored curable resin composition of the present invention preferably has a haze value of 1 to 50%, more preferably 3 to 45%, even more preferably 5 to 40%, and even more preferably 7 to 38%, calculated as a film having a thickness of 2.5 μm. The haze value of the cured film can be measured using a haze meter. The present invention also provides a cured film of the colored curable resin composition of the present invention.

[0123] The present invention also provides a display device including the color filter. The display device of the present invention including at least one color filter of the present invention as a component is useful as a display device with few display defects. Furthermore, the colored curable resin composition of the present invention can form a color filter having haze, and is therefore particularly suitable as a color filter for an organic EL display device. [Example]

[0124] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the examples, % and parts representing the content or amount used are by mass unless otherwise specified.

[0125] <Weight average molecular weight> The weight average molecular weight (Mw) and number average molecular weight (Mn) were measured using a GPC method under the following conditions. Apparatus: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40°C Solvent: Tetrahydrofuran [THF] Flow rate: 1.0mL / min Test liquid solid content concentration: 0.001~0.01% by mass Injection volume: 50μL Detector: RI Calibration standard material ;TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (Manufactured by Tosoh Corporation)

[0126] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the examples, % and parts representing the content or amount used are by mass unless otherwise specified.

[0127] <Preparation Example 1: Preparation of pigment dispersion (A1)> CI Pigment Red 291 19.1 parts CI Pigment Yellow 139 2.9 parts Acrylic pigment dispersant 6.8 parts Propylene glycol monomethyl ether acetate 71.2 parts The above ingredients were mixed, and the pigment was thoroughly dispersed using a bead mill to obtain a pigment dispersion (A1).

[0128] <Preparation Example 2: Preparation of Pigment Dispersion Liquid (A2)> CI Pigment Green 36 5.6 parts CI Pigment Yellow 150 6.8 parts Acrylic liquid pigment dispersant 4.4 parts Propylene glycol monomethyl ether acetate 83.2 parts The pigment dispersion (A2) was obtained by mixing the above ingredients and thoroughly dispersing the pigment using a bead mill. When preparing the colored curable resin composition in Example 7, 242 parts of the pigment dispersion (A2) was used.

[0129] <Preparation Example 2: Preparation of Pigment Dispersion Liquid (A3)> CI Pigment Blue 15:6 9.5 parts CI Pigment Violet 23 1.7 parts Acrylic liquid pigment dispersant 3.1 parts Propylene glycol monomethyl ether acetate 85.8 parts The pigment dispersion (A3) was obtained by mixing the above ingredients and thoroughly dispersing the pigment using a bead mill. When preparing the colored curable resin composition in Example 8, 134 parts of the pigment dispersion (A3) was used.

[0130] <Synthesis Example 1: Preparation of Resin (B)> Into a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 349 parts of propylene glycol monomethyl ether acetate was added, and the mixture was stirred while replacing the atmosphere with nitrogen and heated to 120°C. Next, a monomer mixture consisting of 169.2 parts of benzyl methacrylate, 103.3 parts of methacrylic acid, and 52.9 parts of dicyclopentanyl methacrylate, to which 23.4 parts of t-butylperoxy-2-ethylhexanoate had been added, was added dropwise from the dropping funnel to the flask over 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes to carry out the copolymerization reaction. The flask was then purged with air, and 51.2 parts of glycidyl methacrylate, 1.1 parts of triphenylphosphine, and 1.1 parts of methoquinone were added. The reaction was continued for 10 hours at 120°C to obtain a polymer. Finally, propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a polymer solids concentration of 40%, yielding a resin (B) solution with a weight average molecular weight of 10,300. The acid value per solid of resin (B) was 20.9 mg KOH / g.

[0131] <Examples 1 to 8 and Comparative Examples 1 and 2> (1) Preparation of Colored Curable Resin Composition A colored curable resin composition was obtained by mixing the components shown in Table 1 in the amounts shown in Table 1. In preparing the colored curable resin composition, propylene glycol monomethyl ether acetate was added so that the solids content of the colored curable resin composition was 18%. The unit of the amount of each component in Table 1 is "parts by mass," and the amounts of colorants (A1) to (A3), dispersant (A), resin (B), polymerizable compounds (C1) to (C8), polymerization initiator (D), and leveling agent (E) are calculated as solids content.

[0132] The polymerizable compounds (C1) to (C8), polymerization initiator (D), and leveling agent (E) used in the examples and comparative examples are as follows. Polymerizable compound (C1): glycerin triacrylate (Aronix (registered trademark) M-930; manufactured by Toagosei Co., Ltd.) Polymerizable compound (C2): n-octyl acrylate (Tokyo Chemical Industry Co., Ltd.) Polymerizable compound (C3): dodecyl acrylate (Tokyo Chemical Industry Co., Ltd.) Polymerizable compound (C4): hexadecyl acrylate (Tokyo Chemical Industry Co., Ltd.) Polymerizable compound (C5): docosyl acrylate (Tokyo Chemical Industry Co., Ltd.) Polymerizable compound (C6): dodecyl methacrylate (manufactured by Tokyo Chemical Industry Co., Ltd.) Polymerizable compound (C7): 2-ethylhexyl acrylate (Tokyo Chemical Industry Co., Ltd.) Polymerizable compound (C8): Hexyl acrylate (Tokyo Chemical Industry Co., Ltd.) Polymerization initiator (D): ADEKA ARCLES (registered trademark) NCI-831E (manufactured by ADEKA Corporation) Leveling agent (E): Polyether-modified silicone oil (trade name "Toray Silicone SH8400" manufactured by Toray Dow Corning Co., Ltd.).

[0133] [Table 1]

[0134] <Creating a cured film> The colored curable resin compositions of the Examples and Comparative Examples prepared as described above were applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated) so that the film thickness after post-baking was 2.5 μm, and then pre-baked at 85° C. for 2 minutes to form a colored composition layer. After cooling, the colored composition layer formed on the substrate was exposed to 100 mJ / cm 2 in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). 2 After the light irradiation, the coating was post-baked in an oven at 85° C. for 30 minutes to obtain a colored cured film.

[0135] <Haze measurement> The haze of the resulting colored cured film was measured using a haze meter HZ-2 (manufactured by Suga Test Instruments Co., Ltd.).

[0136] [Table 2]

[0137] The cured films obtained in Examples 1 to 8, in which a specific polymerizable compound (monofunctional monomer) was added, had a large haze and exhibited good scattering properties.

Claims

1. The composition includes a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent, the polymerizable compound includes a monofunctional monomer and a polyfunctional monomer, The monofunctional monomer is represented by the formula (1): 【Chemistry 1】 [In the formula, R １ represents a hydrogen atom or a methyl group, R ２ represents a linear or branched alkyl group having 7 to 22 carbon atoms. A colored curable resin composition comprising a compound represented by the formula:

2. 2. The colored curable resin composition according to claim 1, wherein the resin content is 15 to 50 mass% based on the solid content of the colored curable resin composition.

3. 2. The colored curable resin composition according to claim 1, wherein the content of the monofunctional monomer represented by formula (1) is 40 to 250 parts by mass per 100 parts by mass of the resin.

4. 2. The colored curable resin composition according to claim 1, wherein the content of the monofunctional monomer represented by formula (1) is 150 to 700 parts by mass relative to 100 parts by mass of the polyfunctional monomer.

5. A color filter which is a cured film of the colored curable resin composition according to claim 1.

6. 6. The color filter according to claim 5, which has a haze value of 1 to 50% when converted into a color filter having a thickness of 2.5 μm.

7. A display device comprising the color filter according to claim 5 .

Images