Colored resin composition

Abstract

To provide a colored resin composition which is useful for manufacturing a color filter suitable for an organic EL display device, has excellent low-temperature curability, and further, is excellent in color reproducibility of red color.SOLUTION: Disclosed is a colored resin composition which contains: a colorant; a resin; a polymerizable compound; and a polymerization initiator. The colorant is composed of only a pigment, and the pigment contains C. I. pigment violet 19, a red pigment and a yellow pigment.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a colored resin composition, and more particularly to a colored resin composition for red color. [Background technology]

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

[0003] As a colored resin composition for forming a color filter used in an organic EL display device, a red colored resin composition having good color reproducibility is desired. For example, a composition containing CI Pigment Violet 19, a red pigment, a yellow pigment, a dye polymer, and CI Solvent Orange 62 as colorants is known, as disclosed in Patent Document 1. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2017-201003 Summary of the Invention [Problem to be solved by the invention]

[0005] Since the heat resistance of the organic light-emitting layer used in an organic EL display device is generally low, it is preferable that a colored resin composition for forming a color filter used in an organic EL display device be cured at a low temperature, for example, at 130° C. or less. However, when the composition described in Cited Document 1 was cured at a low temperature, a good color filter could not be obtained. An object of the present invention is to provide a colored resin composition that is useful for producing a color filter suitable for an organic EL display device, has excellent low-temperature curing properties, and also has excellent red color reproducibility. [Means for solving the problem]

[0006] That is, the gist of the present invention is as follows. [1] A colored resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant is composed solely of pigments, The colored resin composition, wherein the pigment comprises CI Pigment Violet 19, a red pigment, and a yellow pigment. [2] The colored resin composition according to [1], wherein the red pigment comprises at least one selected from CI Pigment Red 177, CI Pigment Red 254, CI Pigment Red 269, and CI Pigment Red 291. [3] The colored resin composition according to [1] or [2], wherein the red pigment comprises CI Pigment Red 269. [4] The colored resin composition according to any one of [1] to [3], wherein the yellow pigment comprises CI Pigment Yellow 139. [5] A color filter formed from the colored resin composition according to any one of [1] to [4]. [6] An organic electroluminescence display device comprising the color filter according to [5]. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a colored resin composition that is useful for producing a color filter suitable for an organic EL display device, has excellent low-temperature curing properties, and also has excellent red color reproducibility. DETAILED DESCRIPTION OF THE INVENTION

[0008] The colored resin composition of the present invention contains a colorant, a resin (hereinafter, may be referred to as resin (B)), a polymerizable compound (hereinafter, may be referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter, may be referred to as polymerization initiator (D)), and the colorant (A) is composed only of a pigment (hereinafter, may be referred to as pigment (A1)). Moreover, it is preferable that the colored resin composition according to the present invention further contains a solvent (hereinafter, may be referred to as solvent (E)). The colored resin composition according to the present invention may further contain a polymerization initiation aid (hereinafter, may be referred to as polymerization initiation aid (D1)). The colored resin composition according to the present invention may further contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as components can be used alone or in combination unless otherwise specified.

[0009] <Colorant (A)> In the colored resin composition according to the present invention, the colorant (A) is composed only of the pigment (A1). By comprising the colorant (A) only of the pigment (A1), the colored resin composition can have better low-temperature curing properties than a colored resin composition that also contains a dye as a colorant. Here, "excellent low-temperature curing properties" means that a good color filter without stickiness can be obtained even when cured at a low temperature, such as 130°C or lower. Furthermore, it is preferable that the colored resin composition according to the present invention can form a color filter with excellent solvent resistance even when cured at the low temperature described above. A color filter with excellent solvent resistance refers to a color filter that shows little change in color before and after immersion in a solvent.

[0010] The colored resin composition according to the present invention contains, as the pigment (A1), CI Pigment Violet 19, a red pigment, and a yellow pigment.

[0011] Examples of the red pigment include CI Pigment Red 9, 97, 105, 122, 144, 149, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, and 273. The red pigment preferably contains at least one selected from CI Pigment Red 177, 254, 269, and 291. It is more preferable that the red pigment contains CI Pigment Red 269. Of the total amount of red pigment, it is preferable that 50 mass % or more is CI Pigment Red 177, 254, 269 and / or 291, and more preferably 80 mass % or more is CI Pigment Red 177, 254, 269 and / or 291. It is even more preferable that the entire amount of red pigment is CI Pigment Red 177, 254, 269 and / or 291, and even more preferably that the entire amount of red pigment is CI Pigment Red 269.

[0012] Examples of the yellow pigment include 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, and 231. The pigment preferably contains CI Pigment Yellow 139, and of the total amount of yellow pigment, it is more preferable that CI Pigment Yellow 139 accounts for 50 mass % or more, even more preferable that 80 mass % or more of CI Pigment Yellow 139, and even more preferable that the entire amount of yellow pigment is CI Pigment Yellow 139.

[0013] The content of CI Pigment Violet 19 is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 13% by mass or more, still more preferably 15% by mass or more, and is preferably 60% by mass or less, more preferably 55% by mass or less, even more preferably 52% by mass or less, and still more preferably 50% by mass or less, based on the total amount of colorant (A). Increasing the content of CI Pigment Violet 19 in colorant (A) makes it possible to obtain a colored resin composition with better color reproducibility.

[0014] The content of CI Pigment Violet 19 is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 8% by mass or more, relative to the total amount of solids in the colored resin composition, and is preferably 35% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less.

[0015] Here, the "total amount of solids" in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the colored resin composition. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0016] The content of the red pigment in the total amount of colorant (A) is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, still more preferably 20% by mass or more, and is preferably 85% by mass or less, more preferably 80% by mass or less, even more preferably 75% by mass or less, still more preferably 70% by mass or less, even more preferably 60% by mass or less, even more preferably 55% by mass or less, even more preferably 50% by mass or less, and particularly preferably 45% by mass or less.

[0017] The content of the red pigment is preferably 5% by mass or more, more preferably 8% by mass or more, even more preferably 10% by mass or more, and is preferably 45% by mass or less, more preferably 40% by mass or less, even more preferably 35% by mass or less, even more preferably 30% by mass or less, and even more preferably 25% by mass or less, relative to the total amount of solids in the colored resin composition.

[0018] The content of the yellow pigment in the total amount of colorant (A) is preferably 3 mass% or more, more preferably 5 mass% or more, even more preferably 10 mass% or more, still more preferably 13 mass% or more, even more preferably 15 mass% or more, still more preferably 20 mass% or more, even more preferably 25 mass% or more, and is preferably 55 mass% or less, more preferably 50 mass% or less, even more preferably 45 mass% or less, and still more preferably 40 mass% or less.

[0019] The content of the yellow pigment is preferably 3% by mass or more, more preferably 5% by mass or more, even more preferably 6% by mass or more, still more preferably 8% by mass or more, and even more preferably 10% by mass or more, and is preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less, relative to the total amount of solids in the colored resin composition.

[0020] The content of CI Pigment Violet 19 is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and even more preferably 20 parts by mass or more, relative to 100 parts by mass of the total of the red pigment and the yellow pigment, and is preferably 150 parts by mass or less, more preferably 120 parts by mass or less, and even more preferably 100 parts by mass or less.

[0021] The content ratio of CI Pigment Violet 19 to the red pigment (CI Pigment Violet 19 / red pigment), on a mass basis, is preferably 0.2 or more, more preferably 0.25 or more, even more preferably 0.3 or more, still more preferably 0.4 or more, and is preferably 2.0 or less, more preferably 1.8 or less, even more preferably 1.6 or less.

[0022] The content ratio of CI Pigment Violet 19 to the yellow pigment (CI Pigment Violet 19 / yellow pigment), on a mass basis, is preferably 0.2 or more, more preferably 0.3 or more, even more preferably 0.4 or more, and is preferably 2.2 or less, more preferably 2.0 or less, even more preferably 1.9 or less, even more preferably 1.8 or less, even more preferably 1.6 or less, and even more preferably 1.4 or less.

[0023] The content ratio of the red pigment to the yellow pigment (red pigment / yellow pigment), on a mass basis, is preferably 0.4 or more, more preferably 0.5 or more, even more preferably 0.6 or more, and is preferably 6.0 or less, more preferably 5.0 or less, even more preferably 4.6 or less, even more preferably 1.7 or less, even more preferably 1.5 or less, and even more preferably 1.3 or less.

[0024] The pigment (A1) may further contain a pigment (A1-1) other than CI Pigment Violet 19, red pigments, and yellow pigments. The pigment (A1-1) is not particularly limited and any known pigment can be used, including, for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0025] Examples of the pigment (A1-1) include orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, and 73; Blue pigments such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60; Violet pigments other than CI Pigment Violet 19, such as CI Pigment Violet 1, 23, 32, 36, and 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; Brown pigments such as CI Pigment Brown 23 and 25; Black pigments such as CI Pigment Black 1 and 7;

[0026] When the pigment (A1-1) is contained, its content is preferably 0.1 mass % or more, more preferably 0.5 mass % or more, and even more preferably 1 mass % or more, based on the total amount of the colorant (A), and is preferably 40 mass % or less, more preferably 30 mass % or less, and even more preferably 20 mass % or less.

[0027] The content of the colorant (A) is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 20% by mass or more, still more preferably 25% by mass or more, and is preferably 70% by mass or less, more preferably 65% ​​by mass or less, even more preferably 60% by mass or less, based on the total amount of solids in the colored resin composition. When the content of the colorant (A) is within the above range, the color density when made into a color filter is sufficient, and since the necessary amount of the resin (B) can be contained in the composition, a pattern with sufficient mechanical strength can be formed, which is preferable.

[0028] The content ratio of the colorant (A) to the resin (B) described below (colorant (A) / resin (B)) is, on a mass basis, preferably 1.5 or more, more preferably 1.8 or more, and even more preferably 2.0 or more, and is preferably 4.0 or less, more preferably 3.5 or less, and even more preferably 3.2 or less.

[0029] Furthermore, the total content of CI Pigment Violet 19, the red pigment, and the yellow pigment in the colorant (A) is preferably 80% by mass or more, more preferably 85% by mass or more, and even more preferably 90% by mass or more, and may be 100% by mass, based on the total amount of the colorant (A).

[0030] CI Pigment Violet 19, the red pigment, the yellow pigment, and the pigment (A1-1) may be subjected to, as necessary, rosin treatment, surface treatment using a derivative having an acidic or basic group introduced therein, grafting treatment onto the pigment surface using a polymer compound, atomization treatment using a sulfuric acid atomization method, washing treatment using an organic solvent or water to remove impurities, or treatment to remove ionic impurities using an ion exchange method. The particle size of the pigment is preferably substantially uniform. By adding a dispersant and performing a dispersion treatment, the pigment can be made into a pigment dispersion in which the pigment is uniformly dispersed in the dispersant solution.

[0031] Examples of dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more. Examples of dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLORENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Corporation), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK), and BYK (registered trademark) (manufactured by BYK). Resin (B), which will be described later, may also be used as the dispersant.

[0032] When a dispersant is used, the amount of the dispersant (solid content) used is usually 10 to 200 parts by mass, preferably 13 to 180 parts by mass, and more preferably 15 to 160 parts by mass, per 100 parts by mass of the pigment (A1). When the amount of the dispersant used is within the above range, a pigment dispersion in a more uniformly dispersed state tends to be obtained.

[0033] <Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6]. 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 structural unit derived from (a) plus (b) and a structural unit derived from (c). a copolymer having the following structural units: 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.

[0034] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among these, acrylic acid, methacrylic acid, etc. are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in an alkaline aqueous solution.

[0035] (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.

[0036] 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)").

[0037] 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.

[0038] 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.

[0039] 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), 3,4-epoxytricyclo[5.2.1.0] 2,6 ] decyl (meth)acrylate, 3,4-epoxytricyclo[5.2 .1.0 2,6 ]decyloxyethyl (meth)acrylate, and the like.

[0040] 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.

[0041] 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.

[0042] As for (b), (b1) is preferred in that it can further increase the reliability of the heat resistance, chemical resistance, etc. of the obtained color filter.

[0043] 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 ]Decen-8-yl(meth)a acrylate (commonly referred to as "dicyclopentenyl (meth)acrylate" in the technical field), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, (meth)acrylic acid esters such as 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.

[0044] 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, the colored resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the resulting color filter.

[0045] The resin [K1] can be prepared 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 the method described in the literature. These compounds can be prepared by referring to the cited references.

[0046] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. 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, etc. 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 each monomer can be used, and examples of the solvents include those described below as the organic solvent (E) for the colored resin composition of the present invention.

[0047] The obtained copolymer may be used as a solution after the reaction as it is, or may be used as a concentrated or diluted solution, or may be used as a solid (powder) extracted by a method such as reprecipitation. In particular, by using the solvent contained in the colored resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for preparing the colored resin composition of the present invention, and therefore the manufacturing process of the colored resin composition of the present invention can be simplified.

[0048] 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, the colored resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance, heat resistance, and mechanical strength of the resulting color filter.

[0049] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0050] 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].

[0051] 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].

[0052] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.), a polymerization inhibitor (e.g., hydroquinone, methoquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours to produce 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 this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. 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 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.

[0053] 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:

[0054] 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.

[0055] 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. Polycarboxylic acids include oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, and Examples of suitable 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.

[0056] As the resin (B), a resin having a structural unit having an ethylenically unsaturated bond in the side chain (resin [K4], resin [K5], or resin [K6]) is preferred, and a resin having a structural unit containing a (meth)acryloyl group in the side chain is more preferred. Examples of resins having a structural unit containing a (meth)acryloyl group in the side chain include resins [K4] using as (b) a monomer having a (meth)acryloyl group such as glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3-methyl-3-methacryloyloxymethyloxetane, and tetrahydrofurfuryl acrylate; resins [K5] using as (a) a monomer having a (meth)acryloyl group such as acrylic acid, methacrylic acid, and succinic acid mono[2-(meth)acryloyloxyethyl]; and resins [K6] using as (a) a monomer having a (meth)acryloyl group such as acrylic acid, methacrylic acid, and succinic acid mono[2-(meth)acryloyloxyethyl]. As a resin having a structural unit containing a (meth)acryloyl group in the side chain, a resin [K6] using a monomer having a (meth)acryloyl group such as acrylic acid, methacrylic acid, or succinic acid mono[2-(meth)acryloyloxyethyl] as (a) is preferred.

[0057] The polystyrene-equivalent weight-average molecular weight of resin (B) 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 molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, and the solubility of the unexposed areas in the developer is good, which tends to improve the resolution of the colored pattern.

[0058] The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

[0059] The acid value of the resin (B) is preferably 10 to 170 mg-KOH / g, more preferably 20 to 150 mg-KOH / g, and even more preferably 30 to 135 mg-KOH / g, calculated as solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0060] The content of resin (B) is preferably 5 to 50 mass %, more preferably 8 to 40 mass %, and even more preferably 10 to 35 mass %, based on the total amount of solids in the colored resin composition. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[0061] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

[0062] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such a polymerizable compound include trimethylolpropane, Examples thereof include pentaerythritol tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate.

[0063] The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.

[0064] The content of the polymerizable compound (C) is preferably 3 to 30 mass %, more preferably 5 to 25 mass %, and even more preferably 8 to 20 mass %, based on the total amount of solids in the colored resin composition.

[0065] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and known polymerization initiators can be used. Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, acylphosphine oxide compounds, etc. A preferred polymerization initiator (D) is an O-acyloxime compound.

[0066] The O-acyloxime compound is a compound having a structure represented by formula (d): Hereinafter, * represents a bond.

[0067] [ka]

[0068] The O-acyloxime compound is preferably at least one selected from the group consisting of a compound represented by the following formula (d1) (hereinafter, sometimes referred to as compound (d1)), a compound represented by formula (d2) (hereinafter, sometimes referred to as compound (d2)), and a compound represented by formula (d3) (hereinafter, sometimes referred to as compound (d3)).

[0069] [ka]

[0070] [In formulas (d1) to (d3), R d1represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, a heterocyclic group having 3 to 36 carbon atoms which may have a substituent, an alkyl group having 1 to 15 carbon atoms which may have a substituent, or a group which may have a substituent, which is a combination of an aromatic hydrocarbon group and an alkanediyl group derived from the alkyl group, and the methylene group (-CH2-) contained in the alkyl group is -O-, -CO-, -S-, -SO2- or -NR d5 - has been replaced by That's fine. R d2 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 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or a heterocyclic group having 3 to 36 carbon atoms which may have a substituent. R d4 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or an aliphatic hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, and a methylene group (-CH2-) contained in the aliphatic hydrocarbon group may be replaced by -O-, -CO- or -S-. The methine group (-CH<) contained in the aliphatic hydrocarbon group is replaced with -PO3<. The hydrogen atoms contained in the aliphatic hydrocarbon groups may be substituted with OH groups. R d5 represents an alkyl group having 1 to 10 carbon atoms, and a methylene group (—CH2—) contained in the alkyl group may be replaced with —O— or —CO—.]

[0071] R d1 The number of carbon atoms in the aromatic hydrocarbon group represented by the formula (I) is preferably 6 to 15, more preferably 6 to 12, and even more preferably 6 to 10. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, and a terphenyl group, with a phenyl group and a naphthyl group being more preferred, and a phenyl group being particularly preferred. Also R d1The aromatic hydrocarbon group represented by the formula (I) may have one or more substituents. The substituent is preferably substituted at the α-position or γ-position of the aromatic hydrocarbon group, and more preferably at the γ-position. Examples of the substituent include alkyl groups having 1 to 15 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, and pentadecyl; and halogen atoms, such as fluorine, chlorine, iodine, and bromine. The number of carbon atoms in the alkyl group as the substituent is preferably 1 to 10, and more preferably 1 to 7. The alkyl group as the substituent may be linear, branched, or cyclic, or may be a group that combines a linear group and a cyclic group. The methylene group (-CH2-) contained in the alkyl group as the 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 atoms, chlorine atoms, iodine atoms, and bromine atoms, and are preferably substituted with fluorine atoms.

[0072] R d1 Examples of the alkyl group as a substituent of the aromatic hydrocarbon group represented by the formula include groups represented by the following formula: In the formula, * represents a bond.

[0073] [ka]

[0074] [ka]

[0075] R d1 Examples of the aromatic hydrocarbon group represented by the formula (I) which may have a substituent include groups represented by the following formula: In the formula, * represents a bond.

[0076] [ka]

[0077] [ka]

[0078] R d1 As the aromatic hydrocarbon group which may have a substituent represented by the formula:

[0079] [ka]

[0080] [In the formula, R d6 represents an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, and R d6 The hydrogen atoms contained in may be substituted with halogen atoms. m2 represents an integer of 1 to 5.]

[0081] R d6 The alkyl group represented by R d1 Examples of the substituent of the aromatic hydrocarbon group represented by the formula R include the same groups as those of the alkyl group exemplified above. d6 The number of carbon atoms in R is preferably 2 to 7, and more preferably 2 to 5. d6 The alkyl group represented by the formula (I) may be linear, branched, or cyclic, and is preferably linear. R d6 Examples of the halogen atom which may substitute a hydrogen atom contained in R include a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom, and a fluorine atom is particularly preferred. d6 Preferably, 2 to 10 of the hydrogen atoms contained in R are substituted with halogen atoms, and more preferably 3 to 6 of the hydrogen atoms are substituted with halogen atoms. d6 The substitution position of the O-group is preferably the ortho-position or the para-position, and particularly preferably the para-position. Furthermore, m2 is preferably 1 or 2, and 1 is particularly preferred.

[0082] R d1 The number of carbon atoms in the heterocyclic group represented by the formula (I) is preferably 3 to 20, more preferably 3 to 10, and even more preferably 3 to 5. Examples of the heterocyclic group include a pyrrolyl group, a furyl group, a thienyl group, an indolyl group, a benzofuryl group, and a carbazolyl group. Also R d1 The heterocyclic group represented by the formula (I) may have one or more substituents. The substituents include R d1 Examples of the substituent that the aromatic hydrocarbon group represented by the following formula may have include the same groups as those exemplified above.

[0083] R d1 The alkyl group represented by the formula (R) preferably has 1 to 12 carbon atoms. d1 Examples of the alkyl group represented by the formula (I) include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. Examples of the alkyl group include a silyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, and a pentadecyl group. These alkyl groups may be linear, branched, or cyclic, or may be a combination of a linear group and a cyclic group. d1 In the alkyl group represented by the formula: d5 The hydrogen atom may be replaced by -, and the hydrogen atom may be replaced by an OH group or an SH group.

[0084] R d5 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 chain-shaped (linear or branched) or cyclic, and may be any of linear, branched, and cyclic, or may be a group that combines a chain-shaped group and a cyclic group. d5 In the alkyl group, the methylene group (-CH2-) is replaced by -O- or -CO-. It's okay to know.

[0085] R d1 Specific examples of the alkyl group represented by the formula (I) which may have a substituent include groups represented by the following formula: * represents a bond.

[0086] [ka]

[0087] Furthermore, R d1 and the aromatic hydrocarbon group represented by the above R d1 The number of carbon atoms in the group obtained by combining an alkyl group represented by the formula (I) with an alkanediyl group derived from the alkyl group represented by the formula (I) 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 the substituents include the same groups as those exemplified as the substituents that the aromatic hydrocarbon group and the alkyl group may have. d1 and the aromatic hydrocarbon group represented by the above R d1 Examples of groups formed by combining an alkyl group represented by the formula with an alkanediyl group include aralkyl groups, and specific examples include groups represented by the following formula: In the formula, * represents a bond.

[0088] [ka]

[0089] Among them, R d1 As the alkyl group, an aromatic hydrocarbon group which may have a substituent or an alkyl group which may have a substituent is preferred, and an aromatic hydrocarbon group which may have a substituent is more preferred. preferable.

[0090] R d2The number of carbon atoms in the aromatic hydrocarbon group represented by the formula (I) is preferably 6 to 15, more preferably 6 to 12, and even more preferably 6 to 10. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, and a terphenyl group. R d2 The number of carbon atoms in the heterocyclic group represented by the formula (I) is preferably 3 to 20, more preferably 3 to 10, and even more preferably 3 to 5. Examples of the heterocyclic group include a pyrrolyl group, a furyl group, a thienyl group, an indolyl group, a benzofuryl group, and a carbazolyl group. R d2 The number of carbon atoms in the alkyl group represented by the formula (I) is preferably 1 to 7, more preferably 1 to 5, and even more preferably 1 to 3. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group. The alkyl group may be linear, branched, or cyclic, or may be a group in which a linear group and a cyclic group are combined.

[0091] R d2 As the alkyl group, a chain alkyl group is preferable, more preferably a chain alkyl group having 1 to 5 carbon atoms, still more preferably a chain alkyl group having 1 to 3 carbon atoms, and a methyl group is particularly preferable.

[0092] R d3 The number of carbon atoms in the aromatic hydrocarbon group represented by the formula (I) is preferably 6 to 15, more preferably 6 to 12, and even more preferably 6 to 10. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, and a terphenyl group, with a phenyl group and a naphthyl group being more preferred. Also, R d3The aromatic hydrocarbon group represented by the formula (I) may have one or more substituents. The substituent is preferably substituted at the α-position or the γ-position of the aromatic hydrocarbon group. The substituent is preferably an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and specific examples thereof include 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 d3 The aliphatic hydrocarbon group which may be contained in the aromatic hydrocarbon group represented by the formula (I) preferably has 1 to 7 carbon atoms, and the aliphatic hydrocarbon group may be linear, branched, or cyclic, or may be a group in which a linear group and a cyclic group are combined. In addition, the methylene group (-CH2-) contained in the aliphatic hydrocarbon group may be substituted with -O-, -CO-, or -S-. They may be substituted, and the methine group (-CH<) may be replaced by -N<.

[0093] R d3 Examples of the aliphatic hydrocarbon group that may be contained in the aromatic hydrocarbon group represented by the formula include groups represented by the following formula: In the formula, * represents a bond.

[0094] [ka]

[0095] R d3 Examples of the aromatic hydrocarbon group represented by the formula (I) which may have a substituent include groups represented by the following formula: wherein * represents a bond.

[0096] [ka]

[0097] R d3The number of carbon atoms in the heterocyclic group represented by the formula (I) is preferably 3 to 20, more preferably 3 to 10, and even more preferably 3 to 5. Examples of the heterocyclic group include a pyrrolyl group, a furyl group, a thienyl group, an indolyl group, a benzofuryl group, and a carbazolyl group. Also, R d3 The heterocyclic group represented by the formula (I) may have one or more substituents, and the substituents include R d1 Examples of the substituent that the aromatic hydrocarbon group represented by the following formula may have include the same groups as those exemplified above.

[0098] Among them, R d3 is preferably an aromatic hydrocarbon group having a substituent, 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 or more and 5 or less.

[0099] R d4 The number of carbon atoms in the aromatic hydrocarbon group represented by the formula (I) is preferably 6 to 15, more preferably 6 to 12, and even more preferably 6 to 10. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, and a terphenyl group, with a phenyl group and a naphthyl group being more preferred, and a phenyl group being even more preferred. Also R d4 The aromatic hydrocarbon group represented by the formula (I) may have one or more substituents. The substituents include R d1 Examples of the substituents include the same groups as those which the aromatic hydrocarbon group may have.

[0100] R d4 The number of carbon atoms in the aliphatic hydrocarbon group represented by R is preferably 1 to 13, more preferably 2 to 10, and even more preferably 4 to 9. d4Examples of the aliphatic hydrocarbon group represented by the formula (I) include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, and pentadecyl; alkenyl groups such as ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, butadecenyl, and pentadecenyl; and the like. These aliphatic hydrocarbon groups may be chain-like (linear or branched), cyclic, or may be a combination of a chain-like group and a cyclic group. In addition, R d4 In the aliphatic hydrocarbon group, a methylene group (-CH2- ) may be replaced by -O-, -CO- or -S-, a methine group (-CH<) may be replaced by -PO3<, and a hydrogen atom contained in the aliphatic hydrocarbon group may be replaced by O It may be substituted with an H group.

[0101] R d4 Examples of the aliphatic hydrocarbon group represented by the formula (I) which may have a substituent include groups represented by the following formula: In the formula, * represents a bond.

[0102] [ka]

[0103] R d4 is preferably a chain aliphatic hydrocarbon group which may have a substituent, more preferably a chain alkyl group which has no substituent, and even more preferably a chain alkyl group which has no substituent. It is a branched alkyl group.

[0104] Compound (d1) can be produced by the production method described in JP-A-2014-500852.

[0105] Compound (d2) is R d1 is an alkyl group having 1 to 15 carbon atoms which may have a substituent, Rd2 is an alkyl group having 1 to 10 carbon atoms, R d3 is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, R d4 is an aliphatic hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, More preferably, R d1 represents a methyl group, an ethyl group, or a propyl group, and 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, and R d4 is a methyl group, an ethyl group, or a propyl group, More preferably, R d1 and R d2 is a methyl group, R d3 is an o-tolyl group and R d4 is an ethyl group.

[0106] Compound (d3) is R d1 is an alkyl group having 1 to 15 carbon atoms which may have a substituent, and R d2 is an aromatic hydrocarbon group having 6 to 18 carbon atoms, More preferably, R d1 is a hexyl group and R d2 is a phenyl group.

[0107] 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-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1 ... Examples include N-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine. Commercially available products such as Irgacure OXE01, OXE02, and OXE03 (all manufactured by BASF) and N-1919 (manufactured by ADEKA) may also be used.

[0108] 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.

[0109] [ka]

[0110] 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).

[0111] 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, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole. phenyl)-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), imidazole 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:

[0112] [ka]

[0113] 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.

[0114] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

[0115] Further, examples of the polymerization initiator (D) include benzoin, benzoin methyl ether, benzoin Examples of suitable initiators include benzoin compounds such as benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These may be used in combination with the polymerization initiator aid (D1) described below.

[0116] The content of the polymerization initiator (D) is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, and even more preferably 1 to 12 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving productivity of the color filter.

[0117] <Polymerization initiator aid (D1)> The polymerization initiation aid (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 the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiation aid (D1) 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.

[0118] When these polymerization initiation aids (D1) 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 (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with even higher sensitivity, and the productivity of the color filter tends to improve.

[0119] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the art can be used. Examples thereof 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.

[0120] 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.

[0121] 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, and propylene glycol monomethyl ether. propyl 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.

[0122] 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 ... Examples of the alkyl ether acetate include ethyl 2-methoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0123] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0124] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0125] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0126] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0127] The solvent (E) preferably contains one or more solvents selected from the group consisting of ether solvents, ether ester solvents, and ketone solvents, more preferably contains an ether solvent and an ether ester solvent, and further preferably contains propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate.

[0128] The content of the solvent (E) is preferably 30 to 80% by mass, more preferably 35 to 75% by mass, relative to the total amount of the colored resin composition of the present invention. In other words, the solid content of the colored resin composition is preferably 20 to 70% by mass, more preferably 25 to 65% by mass. When the content of the solvent (E) is within the above range, the flatness during application is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics tend to be good.

[0129] <Leveling Agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms, which may have a polymerizable group in the side chain. 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).

[0130] 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.).

[0131] 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).

[0132] When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005 to 0.2 mass%, more preferably 0.0008 to 0.1 mass%, relative to the total amount of the colored resin composition. This content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0133] <Other ingredients> The colored resin composition of the present invention may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as needed.

[0134] <Method of producing colored resin composition> The colored resin composition of the present invention can be prepared, for example, by mixing the colorant (A), the resin (B), the polymerizable compound (C), the polymerization initiator (D), and optionally the solvent (E), the leveling agent (F), and other components. The colorant (A) may be prepared using the pigment dispersion liquid described above. The desired colored resin composition can be prepared by mixing the remaining components with the pigment dispersion liquid to a predetermined concentration. Furthermore, the colored resin composition after mixing is preferably filtered through a filter having a pore size of about 0.01 to 10 μm.

[0135] <Color filter manufacturing method> Methods for producing a colored pattern from the colored resin composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography is a method in which the colored resin composition is applied to a substrate, dried to form a colored composition layer, and then exposed to light through a photomask and developed. In the photolithography, a colored coating film, which is a cured product of the colored composition layer, can be formed by not using a photomask during exposure and / or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.

[0136] 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.

[0137] 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 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.

[0138] Next, the colored composition layer is exposed to light through a photomask to form a desired colored 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 It is preferable that the irradiation intensity is 60 to 200 J / cm. 2 It is more preferable that the temperature 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.

[0139] 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.

[0140] Furthermore, it is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature may be 200° C. or less to form a color filter to be used in an organic EL display device, but is preferably 170° C. or less, and more preferably 150° C. or less. In the present invention, it is preferable to perform post-baking at a lower temperature, for example, a temperature of 130° C. or less. The lower limit of the post-baking temperature is preferably at least 70° C., more preferably at least 75° C. The post-baking time is preferably from 1 to 120 minutes, more preferably from 5 to 60 minutes.

[0141] The thickness of the coating film after post-baking is, for example, preferably 3 μm or less, more preferably 2.5 μm or less. The lower limit of the thickness of the coating film is not particularly limited, but is usually 0.3 μm or more, and may be 0.5 μm or more.

[0142] According to the colored resin composition of the present invention, it is possible to provide a colored resin composition having excellent low-temperature curing properties, which is useful for producing a color filter suitable for an organic EL display device.

[0143] The colored resin composition of the present invention is also useful for producing a red color filter. For example, the CIE chromaticity coordinates of a red color filter under a C light source and a 2-degree field of view are preferably in the ranges of 0.600≦x≦0.720 and 0.280≦y≦0.360, more preferably 0.630≦x≦0.710 and 0.290≦y≦0.340, and even more preferably 0.660≦x≦0.710 and 0.290≦y≦0.330. In the above range of x and y chromaticity coordinates, the closer x is to 0.710, the more excellent the red color reproducibility of the resulting color filter can be, and therefore, more preferable. [Example]

[0144] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples. In the examples, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass". In the following, the structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD model) or elemental analysis (VARIO-EL; Elemental).

[0145] (Synthesis Example 1) A flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube was charged with 276.8 g of propylene glycol monomethyl ether acetate, and the mixture was stirred while purging with nitrogen and heated to 120°C. Next, a monomer mixture consisting of 92.4 g (0.27 mol) of 2-ethylhexyl acrylate, 184.9 g (0.70 mol) of glycidyl methacrylate, and 12.3 g (0.03 mol) of dicyclopentanyl methacrylate, plus 35.3 g of t-butylperoxy-2-ethylhexanoate (polymerization initiator), was added dropwise from the dropping funnel to the flask over 2 hours. After the dropwise addition, the mixture was stirred for an additional 30 minutes at 120°C to carry out the copolymerization reaction, producing an addition copolymer. The flask was then purged with air, and 93.7 g (0.70 mol) of acrylic acid, 1.5 g of triphenylphosphine (catalyst), and 0.8 g of methoquinone (polymerization inhibitor) were added to the addition copolymer solution. The reaction was continued at 110°C for 10 hours. The epoxy groups derived from glycidyl methacrylate reacted with the acrylic acid, cleaving the epoxy groups and simultaneously introducing polymerizable unsaturated bonds into the polymer side chains. Next, 24.2 g (0.13 mol) of succinic anhydride was added to the reaction system, and the reaction was continued at 110°C for 1 hour. The hydroxyl groups generated by the cleavage of the epoxy groups reacted with the succinic anhydride, introducing carboxyl groups into the side chains, yielding a copolymer (Resin (B-1)). Finally, 383.3 g of propylene glycol monomethyl ether acetate was added to the reaction solution, yielding a resin (B-1) solution with a copolymer solids concentration of 40%. The weight average molecular weight Mw of the copolymer was 6.3 × 10 3 The acid value of the solid content is 34.3m g-KOH / g.

[0146] (Preparation of Dispersion 1) The following ingredients are mixed and the pigment is thoroughly dispersed using a bead mill to obtain the pigment component. Dispersion 1 was obtained. CI Pigment Red 269 (pigment) 14.0 parts Acrylic pigment dispersant 4.2 parts Acrylic pigment dispersion resin (resin (B-1)) 4.2 parts Propylene glycol monomethyl ether acetate 69.8 parts Propylene glycol monomethyl ether 7.8 parts

[0147] (Preparation of Dispersion 2) The following components were mixed, and the pigment was thoroughly dispersed using a bead mill to obtain pigment dispersion 2. CI Pigment Yellow 139 (pigment) 12.0 parts Acrylic pigment dispersant 4.2 parts Acrylic pigment dispersion resin (resin (B-1)) 4.2 parts Propylene glycol monomethyl ether acetate 74.8 parts Propylene glycol monomethyl ether 4.8 parts

[0148] (Preparation of Dispersion 3) The following components were mixed, and the pigment was thoroughly dispersed using a bead mill to obtain Pigment Dispersion 3. CI Pigment Violet 19 (pigment) 13.0 parts Acrylic pigment dispersant 3.7 parts Acrylic pigment dispersion resin (resin (B-1)) 4.3 parts Propylene glycol monomethyl ether acetate 76.6 parts Propylene glycol monomethyl ether 2.5 parts

[0149] (Preparation of Dispersion 4) The following components were mixed, and the pigment was thoroughly dispersed using a bead mill, thereby obtaining Pigment Dispersion Liquid 4. CI Pigment Red 254 (pigment) 10.8 parts Acrylic pigment dispersant 3.8 parts Acrylic pigment dispersion resin (resin (B-1)) 5.5 parts Propylene glycol monomethyl ether acetate 77.1 parts Propylene glycol monomethyl ether 2.9 parts

[0150] (Preparation of Dispersion 5) The following components were mixed, and the pigment was thoroughly dispersed using a bead mill, thereby obtaining Pigment Dispersion Liquid 5. CI Pigment Red 291 (pigment) 13.0 parts Acrylic pigment dispersant 3.5 parts Acrylic pigment dispersion resin (resin (B-1)) 4.0 parts Propylene glycol monomethyl ether acetate 74.8 parts Propylene glycol monomethyl ether 4.7 parts

[0151] (Preparation of Dispersion 6) The following components were mixed, and the pigment was thoroughly dispersed using a bead mill, thereby obtaining Pigment Dispersion Liquid 6. CI Pigment Red 177 (pigment) 14.8 parts Acrylic pigment dispersant 5.7 parts Acrylic pigment dispersion resin (resin (B-1)) 1.4 parts Propylene glycol monomethyl ether acetate 78.0 parts

[0152] Examples 1 to 8 (Preparation of Colored Resin Composition) The components shown in Tables 1 and 2 were mixed to obtain each colored resin composition.

[0153] [Table 1]

[0154] [Table 2]

[0155] In Tables 1 and 2, the components are as follows: Resin (B): Resin (B-1) (solid content conversion) Polymerizable compound (C): dipentaerythritol polyacrylate ("A9550" manufactured by Shin-Nakamura Chemical Co., Ltd., solid content equivalent) Polymerization initiator (D): Irgacure (registered trademark) OXE-03; manufactured by BASF; a compound represented by formula (d1-x)

[0156] [ka] Leveling agent (F): Polyether-modified silicone oil (SH8400; manufactured by Dow Corning Toray Co., Ltd., 10% solids solution in propylene glycol monomethyl ether acetate) Solvent (E): Propylene glycol monomethyl ether acetate

[0157] (Production of colored patterns) A colored resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated) so that the final film thickness was 2.5 μm, and then prebaked at 70° C. for 1 minute to form a colored composition layer. After cooling, the substrate on which the colored composition layer was formed was placed at a distance of 100 μm from a quartz glass photomask, and the resulting layer was exposed to light at 100 mJ / cm 2 in the air using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). 2 At an exposure dose of (365 nm standard) After the irradiation, the substrate was post-baked at 100° C. for 15 minutes using a hot plate to obtain a colored plate on which a colored pattern was formed.

[0158] (spectral evaluation) The colored plate on which the colored pattern was formed was subjected to spectral measurement using a colorimeter (V-630; manufactured by JASCO Corporation) to evaluate its color characteristics. The results of the xy chromaticity coordinates (x, y) in the CIE XYZ color system are shown in Tables 3 and 4. Within the range of x being 0.600 to 0.720 and y being 0.280 to 0.360, the larger x (especially closer to 0.710) indicates better red color reproducibility.

[0159] (Preparation of colored coating film) The colored resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; Corning Incorporated) so that the final film thickness was 1.5 μm, and then prebaked at 70°C for 1 minute to form a colored composition layer. After cooling, the colored resin composition was exposed to light at 200 mJ / cm2 in the air using an exposure machine (TME-150RSK; Topcon Corporation). 2 exposure (based on 365 nm) After the irradiation, the substrate was post-baked at 100° C. for 15 minutes using a hot plate to obtain a colored plate on which a colored coating film was formed. In all of Examples 1 to 8, even when post-baked at a low temperature of 100° C., the composition was cured without leaving any uncured areas or stickiness on the surface, and the low-temperature curability was excellent.

[0160] (Solvent resistance evaluation) The resulting colored plate on which the colored coating film was formed was immersed in propylene glycol monomethyl ether acetate (PGMEA) or propylene glycol monomethyl ether (PGME) for 5 minutes, and the spectral reflectance before and after immersion was measured using a colorimeter (V-630; manufactured by JASCO Corporation). The results of the color change due to immersion, expressed as ΔEab, are shown in Tables 3 and 4. The smaller the value, the smaller the color change, indicating good solvent resistance.

[0161] [Table 3]

[0162] [Table 4]

Claims

1. A colored resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant is composed solely of pigments, The colored resin composition, wherein the pigment comprises C.I. Pigment Violet 19, a red pigment, and a yellow pigment.

2. The colored resin composition according to claim 1, wherein the red pigment comprises at least one selected from C.I. Pigment Red 177, C.I. Pigment Red 254, C.I. Pigment Red 269, and C.I. Pigment Red 291.

3. 3. The colored resin composition according to claim 1, wherein the red pigment comprises C.I. Pigment Red 269.

4. The colored resin composition according to any one of claims 1 to 3, wherein the yellow pigment comprises C.I. Pigment Yellow 139.

5. A color filter formed from the colored resin composition according to any one of claims 1 to 4.

6. An organic EL display device comprising the color filter according to claim 5 .

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