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. More specifically, it relates to a colored resin composition for red color.

Background Art

[0002] An organic EL (Electro-Luminescence) display device using an OLED (Organic Light Emitting Diode) or the like does not require a backlight, so it can be made lighter and thinner than a liquid crystal display device or the like, and high image quality with a fast response speed and high contrast can be achieved. It is power-saving and can be bent, so it is adopted in various fields such as mobile phones, portable information terminals, and televisions.

[0003] As a colored resin composition for forming a color filter used in an organic EL display device, a colored resin composition for red color with good color reproducibility is required. As a colored resin composition for red color, for example, a composition containing C.I. Pigment Violet 19, a red pigment, a yellow pigment, a dye multimer, and C.I. Solvent Orange 62 as a colorant in Patent Document 1 is known.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems 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, as a colored resin composition for forming a color filter used in an organic EL display device, it is preferably cured at a low temperature such as 130 ° C or lower. 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 manufacturing a color filter suitable for an organic EL display device, has excellent low-temperature curability, and further has excellent red color reproducibility.

Means for Solving the Problems

[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, wherein the colorant is composed only of pigments, and the pigment is a colored resin composition containing C.I. Pigment Violet 19, a red pigment, and a yellow pigment. [2] The colored resin composition according to [1], wherein the red pigment contains 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] The colored resin composition according to [1] or [2], wherein the red pigment contains C.I. Pigment Red 269. [4] The colored resin composition according to any one of [1] to [3], wherein the yellow pigment contains C.I. Pigment Yellow 139. [5] A color filter formed from the colored resin composition according to any one of [1] to [4]. [6] An organic EL display device including 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 manufacturing a color filter suitable for an organic EL display device, has excellent low-temperature curability, and further has excellent red color reproducibility.

Modes for Carrying Out the Invention

[0008] The colored resin composition of the present invention contains a colorant, a resin (hereinafter sometimes referred to as resin (B)), a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)), and the colorant (A) is composed only of a pigment (hereinafter sometimes referred to as pigment (A1)). Further, the colored resin composition according to the present invention preferably further contains a solvent (hereinafter sometimes referred to as solvent (E)). Further, the colored resin composition according to the present invention may further contain a polymerization initiation aid (hereinafter sometimes referred to as polymerization initiation aid (D1)). Further, the colored resin composition according to the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)). In this specification, the compounds exemplified as each component can be used alone or in combination of a plurality of kinds 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 the colorant (A) being composed only of the pigment (A1), a colored resin composition excellent in low-temperature curability can be obtained as compared with a colored resin composition containing a dye as a colorant as well. Note that being excellent in low-temperature curability means that, for example, a good color filter without stickiness or the like can be obtained even by a curing treatment at a low temperature such as 130°C or lower. Further, as the colored resin composition according to the present invention, it is preferable that a color filter excellent in solvent resistance can be formed even when a curing treatment is performed at a low temperature as described above. A color filter excellent in solvent resistance means a color filter with little change in color before and after solvent immersion.

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

[0011] Examples of the red pigment include C.I. 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, 273, etc. The red pigment preferably contains at least one selected from C.I. Pigment Red 177, 254, 269 and 291, and more preferably contains C.I. Pigment Red 269. In the total amount of the red pigment, preferably 50% by mass or more is C.I. Pigment Red 177, 254, 269 and / or 291, more preferably 80% by mass or more is C.I. Pigment Red 177, 254, 269 and / or 291, still more preferably the total amount of the red pigment is C.I. Pigment Red 177, 254, 269 and / or 291, and even more preferably the total amount of the red pigment is C.I. Pigment Red 269.

[0012] Examples of the yellow pigment include C.I. 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, etc. The yellow pigment preferably contains C.I. Pigment Yellow 139. In the total amount of the yellow pigment, more preferably 50% by mass or more is C.I. Pigment Yellow 139, still more preferably 80% by mass or more is C.I. Pigment Yellow 139, and even more preferably the total amount of the yellow pigment is C.I. Pigment Yellow 139.

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

[0014] The content rate of C.I. Pigment Violet 19 is preferably 2% by mass or more, more preferably 5% by mass or more, still more preferably 8% by mass or more, and preferably 35% by mass or less, more preferably 30% by mass or less, still more preferably 25% by mass or less, with respect to the total amount of the solid content of the colored resin composition.

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

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

[0017] The content rate of the red pigment is preferably 5% by mass or more, more preferably 8% by mass or more, still more preferably 10% by mass or more, preferably 45% by mass or less, more preferably 40% by mass or less, still more preferably 35% by mass or less, even more preferably 30% by mass or less, and even more preferably 25% by mass or less, based on the total amount of the solid content of the colored resin composition.

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

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

[0020] The content of C.I. Pigment Violet 19 is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, still more preferably 20 parts by mass or more, and preferably 150 parts by mass or less, more preferably 120 parts by mass or less, still more preferably 100 parts by mass or less, based on 100 parts by mass in total of the red pigment and the yellow pigment.

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

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

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

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

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

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

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

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

[0029] In addition, the total content rate of C.I. Pigment Violet 19, red pigment, and yellow pigment contained in the colorant (A) is preferably 80% by mass or more, more preferably 85% by mass or more, still more preferably 90% by mass or more, and may be 100% by mass, based on the total amount of the colorant (A).

[0030] C.I. Pigment Violet 19, red pigment, yellow pigment, and pigment (A1-1) may be subjected to surface treatment using rosin treatment, derivatives with acidic or basic groups introduced, etc., graft treatment on the pigment surface with a polymer compound, etc., micronization treatment by the sulfuric acid micronization method, etc., washing treatment with an organic solvent, water, etc. for removing impurities, removal treatment by an ion exchange method for ionic impurities, etc. The particle size of the pigment is preferably substantially uniform. By performing a dispersion treatment while containing a dispersant, a pigment dispersion in a state of being uniformly dispersed in the dispersant solution can be obtained.

[0031] Examples of the dispersant include surfactants, and any of cationic, anionic, nonionic, and amphoteric surfactants may be used. Specifically, surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants can be mentioned. These dispersants may be used alone or in combination of two or more. When represented by trade names, examples of the dispersant include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK Chemie GmbH), BYK (registered trademark) (manufactured by BYK Chemie GmbH), etc. As the dispersant, the resin (B) described later may be used.

[0032] When using a dispersant, the amount of the dispersant (solid content) used is usually 10 to 200 parts by mass, preferably 13 to 180 parts by mass, 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 with a more uniform dispersion state tends to be obtained.

[0033] <Resin (B)> Resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of Resin (B) include the following resins [K1] to [K6]. Resin [K1]; a copolymer having a structural unit derived from at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)") and a structural unit derived from a monomer (b) having a cyclic ether structure and an ethylenically unsaturated bond having 2 to 4 carbon atoms (hereinafter sometimes referred to as "(b)"); Resin [K2]; a copolymer having a structural unit derived from (a), a structural unit derived from (b), and a structural unit 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 a structural unit derived from (a) and a structural unit derived from (c); Resin [K4]; a copolymer having a structural unit obtained by adding (b) to a structural unit derived from (a) and a structural unit derived from (c); Resin [K5]; a copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and a structural unit derived from (c); Resin [K6]; a copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a polyvalent carboxylic acid and / or a carboxylic anhydride and a structural unit derived from (c).

[0034] Specific examples of (a) include, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, 1,4-cyclohexenedicarboxylic acid; Bicyclic unsaturated compounds containing carboxy groups such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Anhydrides of unsaturated dicarboxylic acids 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, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of polyvalent carboxylic acids with a valency of 2 or more such as succinic acid mono[2-(meth)acryloyloxyethyl] and phthalic acid mono[2-(meth)acryloyloxyethyl]; 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 preferable from the viewpoints of copolymerization reactivity and solubility of the resulting resin in an aqueous alkali solution.

[0035] (b) refers to a polymerizable compound having, for example, 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 the present specification, “(meth)acrylic acid” represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Expressions such as “(meth)acryloyl” and “(meth)acrylate” also have the same meaning.

[0036] (b) includes, for example, monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), and the like.

[0037] (b1) includes, for example, monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)"), and monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").

[0038] (b1-1) includes 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(glycidyloxymethyl)styrene, 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, 2,4,6-tris(glycidyloxymethyl)styrene, and the like.

[0039] (b1-2) includes vinyl cyclohexene monooxide, 1,2-epoxy-4-vinyl cyclohexane (e.g., Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), 3,4-epoxytricyclo[5.2.1.0 2,6 decyl (meth)acrylate, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl oxyethyl (meth)acrylate, etc.

[0040] (b2) is more preferably a monomer having an oxetanyl group and a (meth)acryloyloxy group. 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, etc.

[0041] (b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group. Specifically, examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Biscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0042] (b) is preferably (b1) in that the reliability such as heat resistance and chemical resistance of the resulting color filter can be further enhanced.

[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 dec-8-yl (meth)acrylate (in the art, it is commonly known as "dicyclopentanyl (meth)acrylate" and may also be referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 dec-8-en-8-yl (meth)acrylate (in the art, it is commonly known as "dicyclopentenyl (meth)acrylate"), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate and other (meth)acrylic acid esters; 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, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; Dicarbonylimide 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, N-(9-acridinyl)maleimide; Examples include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like. Among these, (meth)acrylic esters are preferred.

[0044] In resin [K1], the ratio of the structural units derived from each is among all the structural units constituting resin [K1], Structural units derived from (a); 2 to 60 mol% Structural units derived from (b); 40 to 98 mol% It is preferably such that, Structural units derived from (a); 10 to 50 mol% Structural units derived from (b); 50 to 90 mol% More preferably, it is such that. When the ratio of the structural units of resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.

[0045] Resin [K1] can be produced, for example, with reference to the methods described in the literature "Experimental Methods of Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, issued on March 1, 1972) and the cited references described in the said literature.

[0046] Specifically, a method includes putting predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. into a reaction vessel, creating a deoxygenated atmosphere, for example, by replacing oxygen with nitrogen, and heating and maintaining the temperature while stirring. Note that the polymerization initiator, solvent, etc. used here are not particularly limited, and those commonly used in the art can be used. For example, as the polymerization initiator, azo compounds (such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (such as benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, etc.) can be mentioned. As the solvent, any solvent that can dissolve each monomer may be used, and solvents such as those described later as the organic solvent (E) of the colored resin composition of the present invention can be mentioned.

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

[0048] In resin [K2], the ratio of the structural units derived from each is among all the structural units constituting resin [K2], (structural unit) derived from (a); 2 to 45 mol% (structural unit) derived from (b); 2 to 95 mol% (structural unit) derived from (c); 1 to 65 mol% is preferably, (structural unit) derived from (a); 5 to 40 mol% (structural unit) derived from (b); 5 to 80 mol% (structural unit) derived from (c); 5 to 60 mol% is more preferably. When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the resulting color filter tend to be excellent.

[0049] The resin [K2] can be produced, for example, in the same manner as the method described for the production method of the resin [K1].

[0050] In the resin [K3], the ratio of the structural units derived from each is among all the structural units constituting the resin [K3], (a) the structural unit derived from; 2 to 60 mol% (c) the structural unit derived from; 40 to 98 mol% It is preferably that, (a) the structural unit derived from; 10 to 50 mol% (c) the structural unit derived from; 50 to 90 mol% More preferably, it is that. The resin [K3] can be produced, for example, in the same manner as the method described for the production method of the resin [K1].

[0051] The resin [K4] can be produced by obtaining a copolymer of (a) and (c) and adding the cyclic ether having 2 to 4 carbon atoms of (b) to the carboxylic acid and / or carboxylic anhydride of (a). First, a copolymer of (a) and (c) is produced in the same manner as the method described for the production method of the resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that mentioned for the resin [K3].

[0052] Next, a cyclic ether having 2 to 4 carbon atoms of (b) is reacted with a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer. Subsequent to the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced from nitrogen to air, and (b), a reaction catalyst for a carboxylic acid or carboxylic anhydride and a cyclic ether (for example, tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.) and a polymerization inhibitor (for example, hydroquinone, methoxyquinone, etc.) are placed into the flask, and reacted at, for example, 60 to 130 °C for 1 to 10 hours, whereby resin [K4] can be produced. The usage amount of (b) is preferably 5 to 80 moles, more preferably 10 to 75 moles, relative to 100 moles of (a). By setting it within 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. Since the cyclic ether has high reactivity and unreacted (b) hardly remains, (b1) is preferable as (b) used for resin [K4], and further (b1-1) is preferable. The usage amount of the reaction catalyst is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b), and (c). The usage amount of the polymerization inhibitor is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b), and (c). 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 polymerization, etc. Note that, similar to the polymerization conditions, in consideration of the production equipment, the amount of heat generated by polymerization, etc., the charging method and reaction temperature can be appropriately adjusted.

[0053] As a first step, resin [K5] is obtained in the same manner as the production method of resin [K1] described above for a copolymer of (b) and (c). Similar to the above, the obtained copolymer may be used as the reaction solution as it is, or a concentrated or diluted solution may be used, or a solid (powder) taken out by a method such as reprecipitation may be used. The ratios of the structural units derived from (b) and (c) are respectively structural units derived from (b); 5 to 95 mol% structural units derived from (c); 5 to 95 mol% It is preferably, structural units derived from (b); 10 to 90 mol% structural units derived from (c); 10 to 90 mol% more preferably so.

[0054] Furthermore, under the same conditions as the production method of resin [K4], by reacting the carboxylic acid or carboxylic anhydride of (a) with the cyclic ether derived from (b) in the copolymer of (b) and (c), resin [K5] can be obtained. The amount of (a) used for reacting with the copolymer is preferably 5 to 100 mol with respect to 100 mol of (b). Since the cyclic ether has high reactivity and unreacted (b) hardly remains, (b1) is preferable as (b) used for resin [K5], and (b1-1) is more preferable.

[0055] Resin [K6] is a resin obtained by further reacting a polycarboxylic acid and / or carboxylic anhydride with resin [K5]. The polycarboxylic acid and / or carboxylic anhydride is reacted with the hydroxy group generated by the reaction between the cyclic ether derived from (b) and the carboxylic acid or carboxylic anhydride derived from (a). Examples of the polycarboxylic acid include oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, tricarballylic acid, etc. Examples of the carboxylic anhydride 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, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the polycarboxylic acid and / or carboxylic anhydride used is preferably 0.05 to 1 mol, more preferably 0.1 to 0.5 mol, with respect to 1 mol of the amount 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 preferable, and a resin having a structural unit containing a (meth)acryloyl group in the side chain is more preferable. Examples of the resin having a structural unit containing a (meth)acryloyl group in the side chain include, for example, resin [K4] using a monomer having a (meth)acryloyl group such as glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3-methyl-3-methacryloyloxymethyloxetane, and tetrahydrofurfuryl acrylate as (b), resin [K5] using a monomer having a (meth)acryloyl group such as acrylic acid, methacrylic acid, and succinic acid mono[2-(meth)acryloyloxyethyl] as (a), or resin [K6] using a monomer having a (meth)acryloyl group such as acrylic acid, methacrylic acid, and succinic acid mono[2-(meth)acryloyloxyethyl] as (a). As the resin having a structural unit containing a (meth)acryloyl group in the side chain, resin [K6] using a monomer having a (meth)acryloyl group such as acrylic acid, methacrylic acid, and succinic acid mono[2-(meth)acryloyloxyethyl] as (a) is preferable.

[0057] The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 4,000 to 50,000, and still 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 ratio is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern tends to be improved.

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

[0059] The acid value of 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 in terms of solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0060] The content of resin (B) is preferably 5 to 50% by mass, more preferably 8 to 40% by mass, and even more preferably 10 to 35% by mass based on the total amount of the solid content of 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 ratio of the colored pattern tend to improve.

[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 preferably (meth)acrylate compounds.

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

[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% by mass, more preferably 5 to 25% by mass, and even more preferably 8 to 20% by mass based on the total amount of the solid content of 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 any known polymerization initiator 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): In the following, * 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 the following formula (d2) (hereinafter, sometimes referred to as compound (d2)), and a compound represented by the following formula (d3) (hereinafter, sometimes referred to as compound (d3)).

[0069] [ka]

[0070] [In formulas (d1) to (d3), R d1represents a group which may have a substituent and is a combination of 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 an alkane diyl group derived from an aromatic hydrocarbon group and the alkyl group, and a methylene group (-CH2-) contained in the alkyl group may be replaced by -O-, -CO-, -S-, -SO2- or -NR d5 - and may be replaced. 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. A methylene group (-CH2-) contained in the aliphatic hydrocarbon group may be replaced by -O-, -CO- or -S-, a methine group (-CH<) contained in the aliphatic hydrocarbon group may be replaced by -PO3<, and a hydrogen atom contained in the aliphatic hydrocarbon group may be replaced by an OH group. 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 by -O- or -CO-.

[0071] R d1 The number of carbon atoms of the aromatic hydrocarbon group represented by is preferably 6 to 15, more preferably 6 to 12, and still 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, a terphenyl group, etc. A phenyl group and a naphthyl group are more preferable, and a phenyl group is particularly preferable. Also, R d1The aromatic hydrocarbon group represented by 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 substituted at the γ-position. Examples of the substituent include alkyl groups having 1 to 15 carbon atoms such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group; halogen atoms such as fluorine atom, chlorine atom, iodine atom, bromine atom; and the like. The number of carbon atoms of 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 a group combining a chain group and a cyclic group. The methylene group (-CH2-) contained in the alkyl group as the substituent may be replaced by -O- or -S-. Further, the hydrogen atom contained in the alkyl group may be substituted by a halogen atom such as fluorine atom, chlorine atom, iodine atom, bromine atom, and is preferably substituted by a fluorine atom.

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

[0073]

Chemical formula

[0074]

Chemical formula

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

[0076]

Chemical formula

[0077] [Chemical formula]

[0078] R d1 As the aromatic hydrocarbon group which may have a substituent represented by the following formula, the group represented by the following formula is preferable.

[0079] [Chemical formula]

[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 the hydrogen atom contained in R d6 may be substituted with a halogen atom. m2 represents an integer of 1 to 5.]

[0081] R d6 As the alkyl group represented by, the same groups as the alkyl groups exemplified as the substituents of the aromatic hydrocarbon group represented by R d1 can be mentioned. The number of carbon atoms of R d6 is preferably 2 to 7, and more preferably 2 to 5. Further, the alkyl group represented by R d6 may be linear, branched, or cyclic, and is preferably linear. R d6 Examples of the halogen atom which may substitute the hydrogen atom contained in include a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom, and a fluorine atom is particularly preferable. Further, it is preferable that 2 or more and 10 or less of the hydrogen atoms contained in R d6 are substituted with a halogen atom, and it is preferable that 3 or more and 6 or less are substituted with a halogen atom. The substitution position of the R d6 O-group is preferably the ortho position or the para position, and particularly preferably the para position. Also, m2 is preferably 1 to 2, and particularly preferably 1.

[0082] R d1 The number of carbon atoms of the heterocyclic group represented by d1 is preferably 3 to 20, more preferably 3 to 10, and still 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 d1 may have one or more substituents. Examples of the substituents include the same groups as those exemplified as the substituents that the aromatic hydrocarbon group represented by R d1 may have.

[0083] R d1 The number of carbon atoms of the alkyl group represented by d1 is preferably 1 to 12. Examples of the alkyl group represented by R d1 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, a decyl group, an 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 a group combining a linear group and a cyclic group. Also, in the alkyl group represented by R d1 the methylene group (-CH2-) may be replaced by -O-, -CO-, -S-, -SO2-, or -NR d5 -, 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 linear (straight-chain or branched-chain), cyclic, or any of linear, branched, and cyclic, or a group combining a linear group and a cyclic group. Also, in the alkyl group of R d5 the methylene group (-CH2-) may be replaced by -O- or -CO-.

[0085] R d1Examples of the alkyl group which may have a substituent represented by include groups represented by the following formulae. * represents a bond.

[0086]

Chemical formula

[0087] Furthermore, the carbon number of the group combined with the aromatic hydrocarbon group represented by R d1 and the alkanediyl group derived from the alkyl group represented by the above R d1 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 substituent include the same groups as those exemplified as the substituents that the aromatic hydrocarbon group and the alkyl group may have. The R d1 Examples of the group combined with the aromatic hydrocarbon group represented by and the alkanediyl group derived from the alkyl group represented by the above R d1 include aralkyl groups, and specifically, groups represented by the following formulae can be mentioned. In the formula, * represents a bond.

[0088]

Chemical formula

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

[0090] R d2 The carbon number of the aromatic hydrocarbon group represented by is preferably 6 to 15, more preferably 6 to 12, and even more preferably 6 to 10. Examples of the aromatic hydrocarbon group include phenyl group, naphthyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group and the like. R d2The number of carbon atoms of the heterocyclic group represented by is preferably from 3 to 20, more preferably from 3 to 10, and still more preferably from 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 of the alkyl group represented by is preferably from 1 to 7, more preferably from 1 to 5, and still more preferably from 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 a group combining a linear group and a cyclic group.

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

[0092] R d3 The number of carbon atoms of the aromatic hydrocarbon group represented by is preferably from 6 to 15, more preferably from 6 to 12, and still more preferably from 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, and a phenyl group and a naphthyl group are more preferable. Also, R d3 The aromatic hydrocarbon group represented by may have one or more substituents. The substituent is preferably substituted at the α-position or γ-position of the aromatic hydrocarbon group. Examples of the substituent include an aliphatic hydrocarbon group having 1 to 15 carbon atoms, specifically, an alkyl group having 1 to 15 carbon atoms such as 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; an alkenyl group having 1 to 15 carbon atoms such as an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, a nonenyl group, and a decenyl group; and the like. R d3The number of carbon atoms of the aliphatic hydrocarbon group which may be possessed by the aromatic hydrocarbon group represented by is more preferably 1 to 7. The aliphatic hydrocarbon group may be linear, branched, or cyclic, or may be a group combining a chain-like group and a cyclic group. Further, the methylene group (-CH2-) contained in the aliphatic hydrocarbon group may be replaced by -O-, -CO-, or -S-, and the methine group (-CH<) may be replaced by -N<.

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

[0094]

Chemical formula

[0095] R d3 Examples of the aromatic hydrocarbon group which may have a substituent represented by include groups represented by the following formula. In the formula, * represents a bond.

[0096]

Chemical formula

[0097] R d3 The number of carbon atoms of the heterocyclic group represented by is preferably 3 to 20, more preferably 3 to 10, and still 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. Further, the heterocyclic group represented by R d3 may have one or more substituents. Examples of the substituents include the same groups as those exemplified as the substituents which may be possessed by the aromatic hydrocarbon group represented by R d1 Among them, R

[0098] Among them, R d3is preferably an aromatic hydrocarbon group having a substituent, and as the substituent, a linear alkyl group having 1 to 7 carbon atoms (more preferably 1 to 3 carbon atoms) is preferable, and the number of substituents is preferably 2 or more and 5 or less.

[0099] R d4 The aromatic hydrocarbon group represented by is preferably 6 to 15 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms. 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, etc., a phenyl group and a naphthyl group are more preferable, and a phenyl group is even more preferable. Also R d4 The aromatic hydrocarbon group represented by may have one or more substituents. Examples of the substituent include the same groups as those that the aromatic hydrocarbon group of R d1 may have.

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

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

[0102]

Chemical formula

[0103] R d4 is preferably a linear aliphatic hydrocarbon group which may have a substituent, more preferably a linear alkyl group having no substituent, and still more preferably a branched-chain alkyl group having no substituent.

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

[0105] Compound (d2) is preferably a compound in which R d1 is an alkyl group having 1 to 15 carbon atoms which may have a substituent, R d2 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, and R d4 is an aliphatic hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, more preferably, a compound in which R d1 represents a methyl group, an ethyl group or a propyl group, R d2 represents a methyl group, an ethyl group or a propyl group, 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, even more preferably, a compound in which R d1 and R d2 are methyl groups, R d3 is an o-tolyl group and R d4 is an ethyl group.

[0106] Compound (d3) is such that R d1an alkyl group having 1 to 15 carbon atoms which may have a substituent and R d2 a compound in which d2 is an aromatic hydrocarbon group having 6 to 18 carbon atoms is preferable, more preferably, R d1 is a hexyl group and R d2 is a phenyl group.

[0107] Examples of such O-acyl oxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, and the like. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (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 a partial structure represented by formula (d5). In these partial structures, the benzene ring may have a substituent.

[0109]

Chemical formula

[0110] Examples of the compound having the structure represented by formula (d4) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907, 379 (manufactured by BASF) may also be used. Examples of the compound having the structure represented by formula (d5) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, an oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, benzyl dimethyl ketal, etc. In terms of sensitivity, as the alkylphenone compound, a compound having the structure represented by formula (d4) is preferred.

[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, JP-A-6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 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-48-38403, JP-A-62-174204, etc.), an imidazole compound in which the phenyl groups at the 4,4',5,5'-positions are substituted by carboxyalkoxy groups (see, for example, JP-A-7-10913, etc.). Among them, the compounds represented by the following formula and mixtures thereof are preferred.

[0112]

Chem.

[0113] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine and the like.

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

[0115] Furthermore, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetrakis(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, titanocene compounds, and the like. These may be used in combination with a polymerization initiation aid (D1) described later.

[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 still more preferably 1 to 12 parts by mass with respect 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, the sensitivity is increased and the exposure time tends to be shortened, so that the productivity of the color filter is improved.

[0117] <Polymerization initiation aid (D1)> The polymerization initiation aid (D1) is a compound or a sensitizer used to promote the polymerization of the polymerizable compound whose polymerization has been initiated by the polymerization initiator. When the polymerization initiation aid (D1) is included, 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, N-phenylglycine, and the like.

[0118] When using these polymerization initiation aids (D1), their content is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, based on 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 more sensitive coloring pattern can be formed, and the productivity of the color filter tends to improve.

[0119] <Solvent (E)> The solvent (E) is not particularly limited, and solvents commonly used in the art can be used. For example, ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing both -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. can be mentioned.

[0120] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, 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, 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, methyl anisole, and the like.

[0122] Examples of the ether ester solvent 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, ethyl 2-ethoxy-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, diethylene glycol monobutyl ether acetate, and the like.

[0123] Examples of the ketone solvent 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 the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0125] Examples of the aromatic hydrocarbon solvent 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 at least one selected from the group consisting of an ether solvent, an ether ester solvent, and a ketone solvent, more preferably contains an ether solvent and an ether ester solvent, and even more 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, based on 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 coating is good, and the display characteristics tend to be good because the color density is not insufficient when forming a color filter.

[0129] <Leveling agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorosurfactants, and silicone surfactants having fluorine atoms. These may have a polymerizable group in the side chain. Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC) etc. are included.

[0130] Examples of the above-mentioned fluorosurfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by AGC Inc. (formerly Asahi Glass Co., Ltd.)) and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.) etc. are included.

[0131] Examples of the silicone surfactant having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation) etc. are included.

[0132] When the leveling agent (F) is included, the content of the leveling agent (F) is preferably 0.0005 to 0.2% by mass, more preferably 0.0008 to 0.1% by mass, based on the total amount of the colored resin composition. Note that 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 components> 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, chain transfer agents, etc., as necessary.

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

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

[0136] As the substrate, a glass plate such as quartz glass, borosilicate glass, aluminosilicate glass, or soda lime glass with a silica-coated surface, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or a substrate with an aluminum, silver, silver / copper / palladium alloy thin film or the like formed thereon is used. Another color filter layer, resin layer, transistor, circuit, etc. may be formed on these substrates.

[0137] The formation of each color pixel by photolithography can be performed with known or conventional devices and conditions. For example, it can be fabricated as follows. First, a colored resin composition is applied onto the substrate, and volatile components such as solvents are removed by heating and drying (pre-baking) and / or drying under reduced pressure to obtain a smooth colored composition layer. Examples of the coating method include spin coating, slit coating, slit and spin coating, etc. When performing heating and drying, the temperature is preferably 30 to 120°C, more preferably 50 to 110°C. Also, the heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When performing drying under reduced pressure, it is preferably performed in a temperature range of 20 to 25°C under a pressure of 50 to 150 Pa. The film thickness of the colored composition layer is not particularly limited and may be appropriately selected according to the film thickness of the target color filter.

[0138] Next, the colored composition layer is exposed through a photomask for forming the target colored pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target application is used. As the light source used for exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferable. For example, light with a wavelength of less than 350 nm can be cut using a filter that cuts this wavelength range, or light near 436 nm, near 408 nm, or near 365 nm can be selectively extracted using a band-pass filter that extracts these wavelength ranges. Specifically, examples of the light source include a mercury lamp, a light-emitting diode, a metal halide lamp, and a halogen lamp. Also, the exposure amount based on a wavelength of 365 nm is preferably 50 to 300 J / cm 2 and more preferably 60 to 200 J / cm 2 and even more preferably 65 to 180 J / cm 2 is even more preferable. Since it is possible to irradiate the entire exposure surface with parallel light rays uniformly or to perform accurate alignment between the photomask and the substrate on which the coloring composition layer is formed, it is preferable to use an exposure apparatus such as a mask aligner and a stepper.

[0139] By bringing the exposed coloring composition layer into contact with a developer and developing it, a colored pattern is formed on the substrate. By development, the unexposed portion of the coloring composition layer is dissolved and removed by the developer. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration in the aqueous solution of these alkaline compounds is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. Further, the developer may contain a surfactant. The developing method may be any of a paddle method, a dipping method, a spray method, etc. Further, the substrate may be tilted at an arbitrary angle during development. After development, it is preferable to perform water washing.

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

[0141] The film thickness of the coating film after post-baking is preferably, for example, 3 μm or less, and more preferably 2.5 μm or less. The lower limit of the film 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 coloring resin composition of the present invention, it is possible to provide a coloring resin composition having excellent low-temperature curability, which is useful for manufacturing a color filter suitable for an organic EL display device.

[0143] In addition, the coloring resin composition of the present invention is useful for producing a red color filter. As the red color filter, for example, in a C light source, the CIE chromaticity coordinates in a 2-degree field of view are preferably in the range of 0.600 ≦ x ≦ 0.720 and 0.280 ≦ y ≦ 0.360, more preferably in the range of 0.630 ≦ x ≦ 0.710 and 0.290 ≦ y ≦ 0.340, and even more preferably in the range of 0.660 ≦ x ≦ 0.710 and 0.290 ≦ y ≦ 0.330. In the above range of x and y chromaticity coordinates, since a color filter having better red color reproducibility can be obtained as x is closer to 0.710, it is even more preferable.

Examples

[0144] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited by the following examples. In the examples, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass". In the following, the structure of the compound was confirmed by mass spectrometry (LC; Agilent 1200 series, MASS; Agilent LC / MSD series) or elemental analysis (VARIO-EL; manufactured by Elementar Japan Co., Ltd.).

[0145] (Synthesis Example 1) To a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 276.8 g of propylene glycol monomethyl ether acetate was added, 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, to which 35.3 g of t-butyl peroxy-2-ethylhexanoate (a polymerization initiator) was added, was dropped into the flask from the dropping funnel over 2 hours. After completion of the dropping, the mixture was further stirred at 120°C for 30 minutes to conduct a copolymerization reaction to produce an addition copolymer. Thereafter, the inside of the flask was replaced with air, 93.7 g (0.70 mol) of acrylic acid, 1.5 g of triphenylphosphine (a catalyst), and 0.8 g of methoquinone (a polymerization inhibitor) were added to the above addition copolymer solution, and the reaction was continued at 110°C for 10 hours. The epoxy group derived from glycidyl methacrylate was cleaved by the reaction with acrylic acid, and at the same time, a polymerizable unsaturated bond was introduced into the side chain of the polymer. 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 hydroxy group generated by the cleavage of the epoxy group was reacted with succinic anhydride to introduce a carboxy group into the side chain, thereby obtaining a copolymer (resin (B-1)). Finally, 383.3 g of propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a resin (B-1) solution having a solid content concentration of 40% of the copolymer. The weight average molecular weight Mw of the produced copolymer was 6.3×10 3 , and the acid value in terms of solid content was 34.3 mg-KOH / g.

[0146] (Preparation of Dispersion 1) The following components were mixed and the pigment was sufficiently dispersed using a bead mill to obtain Pigment Dispersion 1. 14.0 parts of C.I. Pigment Red 269 (pigment) 4.2 parts of acrylic pigment dispersant 4.2 parts of acrylic pigment dispersion resin (resin (B-1)) 69.8 parts of propylene glycol monomethyl ether acetate 7.8 parts of propylene glycol monomethyl ether

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

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

[0149] (Preparation of Dispersion Liquid 4) The following components were mixed and the pigment was sufficiently dispersed using a bead mill to obtain Pigment Dispersion Liquid 4. 10.8 parts of C.I. Pigment Red 254 (pigment) 3.8 parts of acrylic pigment dispersant 5.5 parts of acrylic pigment dispersion resin (resin (B-1)) 77.1 parts of propylene glycol monomethyl ether acetate 2.9 parts of propylene glycol monomethyl ether

[0150] (Preparation of Dispersion 5) The following components were mixed and the pigment was sufficiently dispersed using a bead mill to obtain Pigment Dispersion 5. 13.0 parts of C.I. Pigment Red 291 (pigment) 3.5 parts of an acrylic pigment dispersant 4.0 parts of an acrylic pigment dispersion resin (resin (B-1)) 74.8 parts of propylene glycol monomethyl ether acetate 4.7 parts of propylene glycol monomethyl ether

[0151] (Preparation of Dispersion 6) The following components were mixed and the pigment was sufficiently dispersed using a bead mill to obtain Pigment Dispersion 6. 14.8 parts of C.I. Pigment Red 177 (pigment) 5.7 parts of an acrylic pigment dispersant 1.4 parts of an acrylic pigment dispersion resin (resin (B-1)) 78.0 parts of propylene glycol monomethyl ether acetate

[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, each component is as follows. Resin (B): Resin (B-1) (in terms of solid content) Polymerizable compound (C): Dipentaerythritol polyacrylate ("A9550" manufactured by Shin-Nakamura Chemical Co., Ltd., in terms of solid content) Polymerization initiator (D): Irgacure (registered trademark) OXE-03; manufactured by BASF; a compound represented by formula (d1-x)

[0156] [Chemical formula] Leveling agent (F): Polyether-modified silicone oil (SH8400; manufactured by Toray Dow Corning Co., Ltd., a propylene glycol monomethyl ether acetate solution with a solid content of 10%) Solvent (E): Propylene glycol monomethyl ether acetate

[0157] (Fabrication of colored pattern) On a 5 cm square glass substrate (Eagle 2000; manufactured by Corning), a colored resin composition was spin-coated so that the final film thickness was 2.5 μm, and then pre-baked at 70 °C for 1 minute to form a colored composition layer. After cooling, with the distance between the substrate on which the colored composition layer was formed and a photomask made of quartz glass set at 100 μm, using an exposure machine (TME-150RSK; manufactured by Topcon Corporation), under an air atmosphere, light was irradiated with an exposure amount of 100 mJ / cm 2 (based on 365 nm standard). After irradiation, post-baking was performed at 100 °C for 15 minutes using a hot plate to obtain a colored plate with a colored pattern formed thereon.

[0158] (Spectral evaluation) For the colored plate with the obtained colored pattern formed thereon, spectroscopy was measured using a colorimeter (V-630; manufactured by JASCO Corporation) to evaluate color characteristics. The results of the xy chromaticity coordinates (x, y) in the CIE XYZ color system are shown in Tables 3 and 4. In the range where x is 0.600 or more and 0.720 or less, and y is 0.280 or more and 0.360 or less, the larger x is (especially the closer it is to 0.710), the better the red color reproducibility is indicated.

[0159] (Preparation of Colored Coating Film) On a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Inc.), a colored resin composition was spin-coated so that the final film thickness would be 1.5 μm, and then pre-baked at 70 °C for 1 minute to form a colored composition layer. After cooling to room temperature, using an exposure machine (TME-150RSK; manufactured by Topcon Corporation), under an air atmosphere, light was irradiated at an exposure dose of 200 mJ / cm 2 (based on 365 nm). After irradiation, post-baking was carried out 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 with post-baking at a low temperature of 100 °C, curing could be achieved without generating uncured portions and without stickiness on the surface, and the low-temperature curability was good.

[0160] (Solvent Resistance Evaluation) Regarding the colored plate on which the obtained colored coating film was formed, it was immersed in propylene glycol monomethyl ether acetate (PGMEA) or propylene glycol monomethyl ether (PGME) for 5 minutes, and the spectra before and after immersion were measured using a colorimeter (V-630; manufactured by JASCO Corporation). Tables 3 and 4 show the results represented by ΔEab for the color change due to immersion. A smaller value of ΔEab means a smaller 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, wherein the colorant is composed only of pigments, the pigments include C.I. Pigment Violet 19, a red pigment, and a yellow pigment, and the red pigment includes C.I. Pigment Red 269. A colored resin composition.

2. The colored resin composition according to claim 1, wherein the yellow pigment includes C.I. Pigment Yellow 139.

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

4. An organic EL display device including the color filter according to claim 3.

Images