Colored curable resin composition

Abstract

To provide a colored curable resin composition that can form a color filter that has strong absorption at a wavelength of 525 nm and is of a deep color and a thin film.SOLUTION: A colored curable resin composition comprises a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D), wherein the colorant (A) comprises an isoindoline pigment (A1) and a perylene compound (1) having an absorption maximum at 400-560 nm and having no absorption maximum in the range of 560-780 nm (excluding 560 nm).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a colored curable resin composition, and particularly to a colored curable resin composition that can be suitably used for red color applications. [Background technology]

[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored curable resin compositions. As colored curable resin compositions for forming the color filters, colored curable resin compositions capable of forming deep-colored and thin-film color filters, particularly colored curable resin compositions capable of forming deep-colored and thin-film color filters that can be suitably used for red, are in demand. As a colored curable resin composition for red, a composition containing CI Pigment Red 242 as a colorant is known (Patent Document 1). However, CI Pigment Red 242 has low absorption at a wavelength of 525 nm, which exhibits red color characteristics, and therefore has weak coloring power, and in order to obtain a deep-colored color filter to expand the color reproduction range, it was necessary to increase the color material concentration in the color filter. Increasing the color material concentration in the color filter is not preferable because it deteriorates the performance as a colored curable resin composition, such as deteriorating the pattern shape. Furthermore, if the coloring power is weak, it is necessary to fabricate a color filter with a thick film in order to impart the desired color characteristics. However, when the color filter is applied to a liquid crystal display device or a solid-state imaging device, a thick film is not preferable because it causes color mixing of light from adjacent pixels.

[0003] Patent Document 2 describes a photosensitive coloring composition for a color filter substrate, which contains a colorant (A), a binder resin (B), a photopolymerizable compound (C), and a photopolymerization initiator (D), and discloses a red photosensitive coloring composition containing CI Pigment Red 179 and an isoindoline pigment. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2010-24436 A [Patent Document 2] JP 2017-116767 A Summary of the Invention [Problem to be solved by the invention]

[0005] However, the color filters formed from the red photosensitive coloring compositions disclosed in Patent Documents 1 and 2 have weak absorption at a wavelength of 525 nm, which is a required characteristic of a red color filter, and the coloring strength is not fully satisfactory. An object of the present invention is to obtain a colored curable resin composition that has strong absorption at a wavelength of 525 nm and can be used to form a deep-colored, thin-film color filter. [Means for solving the problem]

[0006] That is, the gist of the present invention is as follows. [1] A composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator; The colored curable resin composition includes a colorant comprising a perylene compound having an absorption maximum at 400 nm to 560 nm and not having an absorption maximum at more than 560 nm to 780 nm, and an isoindoline pigment. [2] The colored curable resin composition according to [1], wherein the colorant further contains a pigment other than the perylene compound and the isoindoline pigment. [3] The colored curable resin composition according to [1] or [2], further comprising a solvent. [4] A color filter formed from the colored curable resin composition according to any one of [1] to [3]. [5] A solid-state imaging device comprising the color filter according to [4]. Effect of the Invention

[0007] According to the present invention, it is possible to provide a colored curable resin composition that is useful for producing a deep-colored and thin-film color filter. The colored curable resin composition of the present invention is particularly suitable as a colored curable resin composition for red color. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] The colored curable resin composition of the present invention contains a colorant (hereinafter, may be referred to as colorant (A)), a resin (hereinafter, may be referred to as resin (B)), a polymerizable compound (hereinafter, may be referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter, may be referred to as polymerization initiator (D)). The colorant (A) contains a perylene compound having an absorption maximum at 400 nm to 560 nm and not having an absorption maximum at more than 560 nm to 780 nm (hereinafter, may be referred to as perylene compound (1)) and an isoindoline pigment (hereinafter, may be referred to as isoindoline pigment (A1)). The colorant (A) may contain a colorant (hereinafter, may be referred to as colorant (A2)) other than the perylene compound (1) and the isoindoline pigment (A1). It is preferable that the colorant (A) further contains a pigment other than the perylene compound (1) and the isoindoline pigment (A1) (hereinafter, may be referred to as pigment (A2-2)). It is preferable that the colored curable resin composition of the present invention further contains a solvent (hereinafter, may be referred to as solvent (E)). The colored curable resin composition of the present invention may further contain a polymerization initiation aid (hereinafter, may be referred to as polymerization initiation aid (D1)). The colored curable resin composition of the present invention may further contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as each component may be used alone or in combination, unless otherwise specified.

[0009] <Colorant (A)> The colorant (A) includes a perylene compound (1) and an isoindoline pigment (A1).

[0010] <<Perylene compounds (1)>> The perylene compound (1) is a perylene compound having an absorption maximum at 400 nm to 560 nm and not having an absorption maximum at more than 560 nm to 780 nm, and examples thereof include a compound represented by the following formula (1-A). The perylene compound (1) may be a dye or a pigment. The perylene compound (1) may have absorption maxima in a plurality of wavelength regions from 400 nm to 560 nm, and may have, for example, one absorption maximum at 400 nm to 470 nm, one absorption maximum at more than 470 nm to 510 nm, and one absorption maximum at more than 510 nm to 570 nm.

[0011] [ka] [In formula (1-A), R 1 and R 2 each independently represents a methyl group having a substituent, or a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, R 3 ~R 10 each independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.]

[0012] R 1 and R 2 The hydrocarbon group having 2 to 30 carbon atoms represented by the formula (I) may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0013] R 1 and R 2Examples of the saturated or unsaturated chain hydrocarbon group represented by the formula (I) include linear alkyl groups such as an ethyl group, a propyl group, a butyl group, and a pentyl group; branched alkyl groups such as an isopropyl group, a (2-methyl)propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a (2-ethyl)butyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a (1-methyl)pentyl group, a (1-ethyl)pentyl group, and a (1-hexyl)heptyl group; and alkenyl groups such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), an isopropenyl group, a (1-methyl)ethenyl group, a 2-butenyl group, a 3-butenyl group, and a 1,3-butadienyl group.

[0014] R 1 and R 2 Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by the formula (I) include cycloalkyl groups such as a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a 1-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 2,4,6-trimethylcyclohexyl group, and a 2,2,6,6-tetramethylcyclohexyl group; cycloalkenyl groups such as a cyclohexenyl group (e.g., cyclohex-2-ene, cyclohex-3-ene), a cycloheptenyl group, and a cyclooctenyl group; a norbornane group, an adamantyl group, and the like.

[0015] R 1 and R 2 The saturated or unsaturated hydrocarbon group represented by the formula (I) may be a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are combined, and examples thereof include an alkyl group to which one or more alicyclic hydrocarbon groups, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, or a cyclobutylethyl group, are bonded.

[0016] R 1 and R 2Examples of the aromatic hydrocarbon group represented by the formula (I) include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, an o-isopropylphenyl group, an m-isopropylphenyl group, a p-isopropylphenyl group, a 2,3-dimethylphenyl group, a 2,6-dimethylphenyl group, a 2,6-diisopropylphenyl group, a 2,4,6-trimethylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a fluorenyl group, a phenanthryl group, and an anthryl group.

[0017] R 1 and R 2 The aromatic hydrocarbon group represented by the formula (I) is not particularly limited as long as it is a hydrocarbon group having an aromatic hydrocarbon ring, and may be a group in which at least one of a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group is combined with an aromatic hydrocarbon group, and examples thereof include aralkyl groups such as a benzyl group, a 2-methylbenzyl group, a 3,4-methylbenzyl group, a phenylethyl group, and a phenylpropyl group; arylalkenyl groups such as a phenylethenyl group (phenylvinyl group); arylalkynyl groups such as a phenylethynyl group; phenyl groups to which one or more phenyl groups are bonded, such as a biphenylyl group and a terphenylyl group; a cyclohexylmethylphenyl group, a benzylphenyl group, and a (dimethyl(phenyl)methyl)phenyl group.

[0018] R 1 and R 2 Examples of the substituent that the methyl group represented by the formula (I) may have and that the hydrocarbon group having 2 to 30 carbon atoms may have include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, a bromine atom, etc.; a nitro group; a cyano group; an amino group; a hydroxy group; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, etc.; a sulfanyl group; an alkylsulfanyl group having 1 to 6 carbon atoms such as a methylsulfanyl group, an ethylsulfanyl group, etc.; a carboxy group; a carbamoyl group; an alkoxycarbonyl group having 2 to 6 carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group, etc.; a sulfo group; a sulfamoyl group; and an alkoxysulfonyl group having 1 to 6 carbon atoms such as a methoxysulfonyl group, an ethoxysulfonyl group, etc.

[0019] R 1 and R 2 are each independently preferably a methyl group having a substituent, or a hydrocarbon group having 8 to 20 carbon atoms which may have a substituent, more preferably a methyl group having a substituent, or a hydrocarbon group having 10 to 15 carbon atoms which may have a substituent, even more preferably a methyl group having a substituent, a linear hydrocarbon group having 10 to 15 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 10 to 15 carbon atoms which may have a substituent, even more preferably a methyl group having a substituent, a saturated linear hydrocarbon group having 10 to 15 carbon atoms, or an aromatic hydrocarbon group having 10 to 15 carbon atoms, and particularly preferably a methyl group having a carboxy group as a substituent, a branched alkyl group having 10 to 15 carbon atoms, or a monocyclic aromatic hydrocarbon group having 10 to 15 carbon atoms. Also, R 1 and R 2 are preferably the same group.

[0020] R 3 ~R 10 The hydrocarbon group having 1 to 10 carbon atoms represented by the formula (I) includes a methyl group and does not include a group having 11 or more carbon atoms. 1 and R 2 The hydrocarbon group may be the same as that represented by the following formula:

[0021] R 3 ~R 10 The substituents that the hydrocarbon group represented by the formula (I) may have include R 1 and R 2 The substituents are the same as those which may be contained in the hydrocarbon group represented by the following formula:

[0022] R 3 ~R 10 are each independently preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, even more preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and particularly preferably a hydrogen atom. Also, R 3 ~R 10 are preferably the same group.

[0023] The maximum absorption of a perylene compound can be measured by preparing a chloroform solution containing 0.001% by mass of the perylene compound, then placing the solution in a measurement container (e.g., a cuvette) having an optical path length of 1 cm, and measuring the spectroscopic spectrum.

[0024] The content of the perylene compound (1) is preferably 0.1 to 50 parts by mass, more preferably 0.5 to 40 parts by mass, even more preferably 1 to 35 parts by mass, and even more preferably 5 to 30 parts by mass, relative to 100 parts by mass of the resin (B).

[0025] The content of the perylene compound (1) is preferably 5 to 90 mass%, more preferably 10 to 80 mass%, further preferably 20 to 70 mass%, and particularly preferably 25 to 65 mass%, of the total amount of the colorant (A). When the content of the perylene compound (1) is within the above range, a colored curable resin composition capable of forming a color filter having good red color characteristics can be obtained.

[0026] <<Isoindoline pigment (A1)>> The isoindoline pigment (A1) is not particularly limited as long as it is an isoindoline pigment, and any known isoindoline pigment can be used.

[0027] Examples of the isoindoline pigment (A1) include isoindoline pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists), and specific examples thereof include CI Pigment Yellow 109, 110, 137, 139, 173, 177, 179, 185, CI Pigment Orange 61, 69, and the like.

[0028] The isoindoline pigment (A1) may be an isoindoline pigment other than those classified as pigments in the Color Index (published by The Society of Dyers and Colourists), and examples thereof include compounds represented by the following formula (Y).

[0029] [ka]

[0030] [In formula (Y), R 11 ~R 15 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. R 16 and R 17 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms or an optionally substituted heterocyclic group. L 11 and L 12 represents -CO- or -SO2-.

[0031] R 11 ~R 17 The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) includes a methyl group and does not include a group having 21 or more carbon atoms. 1 and R 2 The hydrocarbon group may be the same as that represented by the following formula:

[0032] R 11 ~R 17 The heterocyclic group represented by the following formula (I) may be a monocyclic group or a polycyclic group.

[0033] R 11 ~R 17 The substituents which may be contained in the hydrocarbon group or heterocyclic group represented by the formula (I) are R 1 and R 2The substituents are the same as those which may be contained in the hydrocarbon group represented by the following formula:

[0034] R 11 ~R 15 is preferably a hydrogen atom.

[0035] R 16 and R 17 As the alkyl group, a substituted aromatic hydrocarbon group having 6 to 20 carbon atoms is preferable, a substituted aromatic hydrocarbon group having 6 to 10 carbon atoms is more preferable, and an aromatic hydrocarbon group having 6 to 10 carbon atoms and a carboxy group as a substituent is even more preferable.

[0036] L 11 and L 12 As the group, -CO- is preferable.

[0037] As the isoindoline pigment (A1), from the viewpoint of obtaining a colored curable resin composition capable of forming a color filter having particularly good red color characteristics, a yellow isoindoline pigment is preferred, CI Pigment Yellow 139, 185 or a compound represented by formula (Y) is more preferred, CI Pigment Yellow 139 or 185 is even more preferred, and CI Pigment Yellow 139 is even more preferred. These isoindoline pigments (A1) may be used alone or in combination of two or more.

[0038] The content of the isoindoline pigment (A1) is preferably from 0.1 to 50 parts by mass, more preferably from 0.5 to 40 parts by mass, and further preferably from 1 to 30 parts by mass, relative to 100 parts by mass of the resin (B).

[0039] The content of the isoindoline pigment (A1) is preferably 10 to 80 mass%, more preferably 20 to 75 mass%, further preferably 30 to 70 mass%, and particularly preferably 35 to 65 mass%, of the total amount of the colorant (A). When the content of the isoindoline pigment (A1) is within the above range, a colored curable resin composition capable of forming a color filter having good red color characteristics can be obtained.

[0040] <<Colorant (A2)>> The colored curable resin composition of the present invention may contain, as the colorant (A2), a dye other than the perylene compound (1) and the isoindoline pigment (A1) (hereinafter, may be referred to as dye (A2-1)) and / or a pigment (A2-2), and preferably contains the pigment (A2-2).

[0041] The dye (A2-1) is not particularly limited, and known dyes can be used as long as it does not include the perylene compound (1), and examples of such dyes include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as having a hue other than pigments in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used according to chemical structure include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, perylene dyes (excluding the perylene compound (1)), and nitro dyes. Among these, organic solvent-soluble dyes are preferred.

[0042] The pigment (A2-2) is not particularly limited, and any known pigment can be used, so long as it does not include the perylene compound (1) and the isoindoline pigment (A1). Examples of the pigment include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments classified as pigments include yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 117, 125, 128, 147, 148, 150, 153, 154, 166, 194, and 214; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 43, 51, 55, 59, 64, 65, 71, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 166, 168, 176, 177, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 269, 291; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 16, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58; Brown pigments such as CI Pigment Brown 23, 25; Examples of black pigments include CI Pigment Black 1 and 7.

[0043] As the pigment (A2-2), from the viewpoint of obtaining a colored curable resin composition capable of forming a color filter having particularly good red color characteristics, a red pigment is preferable, and CI Pigment Red 254 is more preferable.

[0044] When the colored curable resin composition of the present invention contains a colorant (A2), the content of the colorant (A2) (dye (A2-1) and / or pigment (A2-2)) is preferably 0.1% by mass or more, more preferably 1% by mass or more, even more preferably 10% by mass or more, even more preferably 20% by mass or more, preferably 60% by mass or less, more preferably 50% by mass or less, and even more preferably 40% by mass or less in the total amount of the colorant (A). If the content of the colorant (A2) is within the above range, a colored curable resin composition capable of forming a color filter having good red color characteristics can be obtained. In particular, the content of the pigment (A2-2) is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, preferably 60% by mass or less, more preferably 50% by mass or less, and even more preferably 55% by mass or less in the total amount of the colorant (A).

[0045] The perylene compound (1), the isoindoline pigment (A1), and the pigment (A2-2) used as needed preferably have a uniform particle size. By adding a pigment dispersant and carrying out a dispersion treatment, a pigment dispersion in which the pigment is uniformly dispersed in the solution can be obtained.

[0046] The pigment dispersant may be, for example, a surfactant, which may be any of cationic, anionic, nonionic, and amphoteric surfactants. Specific examples include polyester, polyamine, and acrylic dispersants. These dispersants may be used alone or in combination of two or more. Examples of the dispersant include, under the trade names, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (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.), and Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.). Resin (B), which will be described later, may be used as the dispersant. When a pigment dispersant is used, the amount used is preferably 1 part by mass or more and 200 parts by mass or less, and more preferably 10 parts by mass or more and 150 parts by mass or less, relative to 100 parts by mass of the pigment. When the amount of the pigment dispersant used is within the above range, a pigment dispersion in a uniformly dispersed state tends to be obtained.

[0047] When two or more kinds of pigments are used, they may be mixed as a dispersion liquid when used.

[0048] The content of the colorant (A) is preferably 0.1 to 50 mass%, more preferably 0.5 to 40 mass%, and even more preferably 1 to 30 mass%, based on the total amount of solids in the colored curable 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. 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 curable resin composition. The total amount of solids and the content of each component relative thereto can be measured by a known analytical means such as liquid chromatography or gas chromatography.

[0049] <Resin (B)> Resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably a resin having a structural unit derived from at least one type (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides. Resin (B) preferably further has at least one structural unit selected from the group consisting of a structural unit derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, a structural unit derived from a monomer (c) (however different from (a) and (b)) (hereinafter sometimes referred to as "(c)") copolymerizable with (a), and a structural unit having an ethylenically unsaturated bond in a side chain.

[0050] Specific examples of (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and mono[2-(meth)acryloyloxyethyl]succinate, and preferred are acrylic acid, methacrylic acid, and maleic anhydride.

[0051] (b) is preferably a monomer 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 a (meth)acryloyloxy group. In this specification, the term "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning. Examples of (b) include glycidyl (meth)acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl(meth)acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxetane, tetrahydrofurfuryl(meth)acrylate, etc., and preferably, glycidyl(meth)acrylate, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxetane.

[0052] Examples of (c) include methyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]Decan-8-yl (meth)acrylate, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene, etc. are included, and preferably styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, etc. are preferred.

[0053] The resin having a structural unit having an ethylenically unsaturated bond in the side chain can be produced by adding (b) to a copolymer of (a) and (c), or by adding (a) to a copolymer of (b) and (c). The resin may be a resin obtained by adding (a) to a copolymer of (b) and (c) and then reacting with a carboxylic acid anhydride.

[0054] The polystyrene-equivalent weight average molecular weight of resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. 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.

[0055] The acid value of the resin (B) is preferably 30 to 160 mg-KOH / g, more preferably 40 to 140 mg-KOH / g, and further preferably 50 to 130 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.

[0056] The content of the resin (B) is preferably from 5 to 65 mass %, more preferably from 8 to 60 mass %, and further preferably from 10 to 57 mass %, based on the total amount of solids in the colored curable resin composition.

[0057] <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.

[0058] 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, and dipentaerythritol hexa(meth)acrylate.

[0059] The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

[0060] The content of the polymerizable compound (C) is preferably from 10 to 50 mass %, more preferably from 15 to 45 mass %, and further preferably from 20 to 40 mass %, based on the total amount of solids in the colored curable resin composition.

[0061] <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 polymerization initiators that generate active radicals 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-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine. amine, 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and the like.

[0062] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of 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, thereby improving the productivity of the color filter.

[0063] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator, or a sensitizer. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiator 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.

[0064] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, 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 colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to improve.

[0065] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule and not containing -COO-), ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide, etc. can be mentioned.

[0066] Specific examples of the solvent include ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone (solvents that contain -COO- but not -O- in the molecule); Ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, and diethylene glycol methyl ethyl ether (solvents that contain -O- but do not contain -COO- in the molecule); Ether ester solvents (solvents containing -COO- and -O- in the molecule) such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and diethylene glycol monoethyl ether acetate; Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone (hereinafter sometimes referred to as diacetone alcohol), heptanone, 4-methyl-2-pentanone, cyclohexanone, etc. (solvents that contain -CO- in the molecule but do not contain -COO-); Alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents that contain OH in the molecule but do not contain -O-, -CO-, or -COO-); Amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; and the like.

[0067] More preferred solvents are propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and cyclohexanone.

[0068] When the solvent (E) is contained, the content of the solvent (E) is preferably 70 to 95 mass% and more preferably 75 to 92 mass% based on the total amount of the colored curable resin composition of the present invention. In other words, the content of the total amount of solids in the colored curable resin composition is preferably 5 to 30 mass% and more preferably 8 to 25 mass% based on the total amount of the colored curable resin composition of the present invention. 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.

[0069] <Leveling agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants having 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.Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and 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).

[0070] The fluorine-based surfactant may include surfactants having a fluorocarbon chain in the molecule.Specific examples include 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 Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.).

[0071] 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).

[0072] When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.001 to 0.2 mass% and more preferably 0.002 to 0.1 mass% based on the total amount of the colored curable resin composition. This content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0073] <Other ingredients> The colored curable resin composition of the present invention may contain additives known in the technical field, such as a filler, another polymer compound, an adhesion promoter, an antioxidant, a light stabilizer, and a chain transfer agent, as necessary.

[0074] <Method for producing colored curable resin composition> The colored curable resin composition of the present invention can be prepared by mixing the colorant (A), the resin (B), the polymerizable compound (C), and the polymerization initiator (D), as well as the solvent (E), the leveling agent (F), and other components that are used as needed. The perylene compound (1), the isoindoline pigment (A1), and the pigment (A2-2) used as necessary are preferably mixed in advance with a part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle size of the pigment becomes about 0.2 μm or less. At this time, the pigment dispersant and a part or all of the resin (B) may be mixed as necessary. The remaining components are mixed into the pigment dispersion thus obtained to a predetermined concentration, thereby preparing a colored curable resin composition.

[0075] <Manufacturing method of color filters> Examples of methods for producing a colored pattern from the colored curable resin composition of the present invention include a photolithography method, an inkjet method, and a printing method. Among these, the photolithography method is preferred. The photolithography method is a method in which the colored curable resin composition is applied to a substrate, dried to form a colored composition layer, and the colored composition layer is exposed through a photomask and developed. In the photolithography method, 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.

[0076] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or soda lime glass with a silica-coated surface; a resin plate such as polycarbonate, polymethylmethacrylate, or polyethylene terephthalate; silicon; or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. On these substrates, another color filter layer, a resin layer, a transistor, a circuit, or the like may be formed. A silicon substrate treated with HMDS (1,1,1,3,3,3-hexamethyldisilazane) may also be used.

[0077] The formation of each color pixel by photolithography can be carried out using known or conventional devices and conditions. For example, the pixel can be produced as follows. First, the colored composition is applied onto a substrate, and then dried by heating and drying (pre-baking) and / or drying under reduced pressure to remove volatile components such as a solvent, 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 5 minutes, more preferably 30 seconds to 3 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 and at a temperature in the range of 20 to 25°C. The thickness of the colored composition layer is not particularly limited, and may be appropriately selected depending on the intended thickness of the color filter.

[0078] Next, the colored composition layer is exposed through a photomask for forming a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern depending on the intended use is used. The light source used for exposure is preferably a light source that generates 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, around 408 nm, and around 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specifically, the light source may be a mercury lamp, a light-emitting diode, a metal halide lamp, a halogen lamp, etc. It is preferable to use an exposure device because it is possible to uniformly irradiate the entire exposure surface with parallel light and to accurately align the photomask with the substrate on which the colored composition layer is formed. As the exposure device, a mask aligner such as a stepper (reduced projection exposure device) or a proximity exposure device is preferable.

[0079] The colored composition layer after exposure is brought into contact with a developer for development, thereby forming a colored pattern on the substrate. The unexposed portion of the colored composition layer is dissolved in the developer and removed by development. The developer is preferably, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, 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 inclined at an arbitrary angle during the developing. After development, it is preferable to wash with water.

[0080] Furthermore, it is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably 80° C. or more, more preferably 100° C. or more, even more preferably 150° C. or more, even more preferably 160° C. or more, preferably 250° C. or less, and more preferably 235° C. or less. The post-baking time is preferably 1 minute or more, more preferably 2 minutes or more, even more preferably 10 minutes or more, preferably 120 minutes or less, more preferably 60 minutes or less, and even more preferably 30 minutes or less.

[0081] 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 0.1 μm, and may be 0.5 μm or more, or may be 1.0 μm or more.

[0082] The color filter formed from the colored curable resin composition of the present invention is a deep color and a thin film. In particular, the absorption at a wavelength of 525 nm required as a characteristic of a red color filter is stronger than that of a color filter formed from a colored curable resin composition containing CI Pigment Red 242 as a colorant. The strength of absorption at a wavelength of 525 nm of the color filter formed from the colored curable resin composition of the present invention, that is, the absorbance, is preferably 1.1 times or more, more preferably 1.2 times or more, and the upper limit is not particularly limited, and may be, for example, 5.0 times or less, 4.0 times or less, or 3.0 times or less. In addition to having a strong absorption at a wavelength of 525 nm, the colored curable resin composition preferably has a suppressed absorption at a wavelength of more than 560 nm to 780 nm, particularly at a wavelength of 565 nm. By suppressing absorption in the wavelength range of more than 560 nm to 780 nm, good color reproducibility can be achieved. Specifically, the absorbance at 525 nm of the color filter formed from the colored curable resin composition is preferably 0.65 or more, more preferably 0.70 or more, and even more preferably 0.75 or more, and the absorbance at 565 nm of the color filter formed from the colored curable resin composition is preferably 1.0 or less, more preferably 0.8 or less, and even more preferably 0.7 or less.

[0083] Since the colored curable resin composition of the present invention has a strong absorption at a wavelength of 525 nm and a suppressed absorption at a wavelength of more than 560 nm to 780 nm, a deep color filter can be obtained without increasing the color material concentration or thickening the film, particularly when forming a red color filter. The color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state imaging device, and is particularly useful for a solid-state imaging device. EXAMPLES

[0084] 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, "parts" means "parts by mass" and "%" means "% by mass" unless otherwise specified. In the following synthesis examples, compounds were identified by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD model) or elemental analysis (VARIO-EL; Elemental Corporation).

[0085] (Synthesis Example 1) 8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 10 parts of 7-aminotridecane (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto Chemical Industry Co., Ltd.), and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and stirred at 150°C for 3 hours. While keeping the obtained mixture at 20°C or less, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Industry Co., Ltd.) and 1300 parts of water prepared in advance were added, resulting in the formation of an orange-red precipitate. The mixture containing this orange-red precipitate was filtered, and the residue after filtration was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 12 parts of a compound represented by formula (1-1) (hereinafter also referred to as compound (1-1)) (yield 79%).

[0086] [ka]

[0087] <Identification of compound (1-1)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 755 Exact Mass: 754

[0088] (Synthesis Example 2) 8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.8 parts of glycine (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto Chemical Industry Co., Ltd.), and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and stirred at 150°C for 7 hours. While keeping the obtained mixture at 20°C or less, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Industry Co., Ltd.) and 1300 parts of water prepared in advance were added, resulting in the formation of an orange-red precipitate. The mixture containing this orange-red precipitate was filtered, and the residue after filtration was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 9.1 parts of a compound represented by formula (1-2) (also referred to as compound (1-2)) (yield 88%).

[0089] [ka]

[0090] <Identification of compound (1-2)> (Mass spectrometry) Ionization mode = ESI-: m / z = [MH] - 505 Exact Mass: 506

[0091] (Synthesis Example 3) A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80° C. with stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 ] A solution of 289 parts of a mixture of decan-9-yl acrylate (content ratio 1:1) dissolved in 125 parts of propylene glycol monomethyl ether acetate was dropped using a dropping pump over about 5 hours. Meanwhile, a solution of 33 parts of a polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was dropped into the flask using another dropping pump over about 6 hours. After the dropping was completed, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin (B-2)) with a solid content of 35.1%. The weight average molecular weight Mw of the resulting copolymer was 9200, the degree of dispersion was 2.08, and the acid value converted to solid content was 77 mg-KOH / g. Resin (B-2) has the following structural units.

[0092] [ka]

[0093] The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Equipment: K2479 (Shimadzu Corporation) Column: SHIMADZU Shim-pack GPC-80M Column temperature: 40°C Solvent: THF (tetrahydrofuran) Flow rate; 1.0mL / min Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0094] The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

[0095] [Preparation of Dispersion 1] 2.5 parts of Lumogen F Orange 240 (BASF), 2.5 parts of compound (1-2), 5 parts of dispersant (BYK BYKLPN-6919), 4 parts of resin (B-2) (solid content equivalent), and propylene glycol monomethyl ether acetate were mixed, 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 1. The amount of propylene glycol monomethyl ether acetate in dispersion 1 was 186 parts, which is the amount of propylene glycol monomethyl ether acetate derived from resin (B-2).

[0096] [Preparation of Dispersion 2] 12 parts of CI Pigment Red 242, 4.3 parts of dispersant (BYKLPN-6919 manufactured by BYK), 2.7 parts of resin (B-2) (solid content equivalent), and propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). The zirconia beads were then removed by filtration to obtain dispersion 2. The amount of propylene glycol monomethyl ether acetate in dispersion 2 was 81 parts, which is the amount including propylene glycol monomethyl ether acetate derived from resin (B-2).

[0097] [Preparation of Dispersion 3] 15 parts of CI Pigment Red 179, 3.8 parts of dispersant (BYK BYKLPN-6919), 3.0 parts of resin (B-2) (solid content equivalent), and propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 3. The amount of propylene glycol monomethyl ether acetate in dispersion 3 was 78.2 parts, which is the amount including propylene glycol monomethyl ether acetate derived from resin (B-2).

[0098] [Preparation of Dispersion 4] 12 parts of CI Pigment Yellow 139, 4.2 parts of dispersant (BYK BYKLPN-6919), 4.2 parts of resin (B-2) (solid content equivalent), and propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 4. The amount of propylene glycol monomethyl ether acetate in dispersion 4 was 79.6 parts, which is the amount of propylene glycol monomethyl ether acetate derived from resin (B-2).

[0099] [Preparation of Dispersion 5] 14.1 parts of CI Pigment Red 254, 4.2 parts of dispersant (BYK BYKLPN-6919), 4.9 parts of resin (B-2) (solid content equivalent), and propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 5. The amount of propylene glycol monomethyl ether acetate in dispersion 5 was 76.8 parts, which is the amount of propylene glycol monomethyl ether acetate derived from resin (B-2).

[0100] [Preparation of Dispersion 6] 10.3 parts of CI Pigment Yellow 185, 4.1 parts of dispersant (BYKLPN-6919 manufactured by BYK), 4.6 parts of resin (B-2) (solid content equivalent), and propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). The zirconia beads were then removed by filtration to obtain dispersion 6. The amount of propylene glycol monomethyl ether acetate in dispersion 6 was 81.0 parts, which is the amount of propylene glycol monomethyl ether acetate derived from resin (B-2).

[0101] Each compound was dissolved in chloroform to obtain a solution with a concentration of 0.001% by mass. The solution was measured using a UV-Vis-NIR spectrophotometer V-650 (manufactured by JASCO Corporation). The measurement results of the wavelength at the maximum point of the maximum absorption of each compound (maximum absorption wavelength) are shown in Table 1.

[0102] [Table 1]

[0103] [Examples 1 to 4, Comparative Examples 1 to 2] <Preparation of Colored Curable Resin Composition> The components shown in Table 2 were mixed to obtain each colored curable resin composition.

[0104] [Table 2]

[0105] Resin (B): Resin (B-2) (solid content conversion) Polymerizable compound (C): dipentaerythritol polyacrylate ("A9550" manufactured by Shin-Nakamura Chemical Co., Ltd.; solid content equivalent) Polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure® OXE 01; manufactured by BASF) Solvent (E-1): Propylene glycol monomethyl ether acetate Solvent (E-2): Cyclohexanone Leveling agent (F): Polyether modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.; solid content equivalent)

[0106] <Preparation of colored coating film> A colored curable resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; Corning Incorporated), and then prebaked at 100°C for 3 minutes to form a colored composition layer. After cooling, the substrate was exposed to light at 60 mJ / cm2 in the air using an exposure machine (TME-150RSK; Topcon Corporation). 2 The colored composition layer was irradiated with light at an exposure amount (based on 365 nm) of 1000 nm, and then post-baked in an oven at 230° C. for 20 minutes to obtain a colored coating film.

[0107] <Film thickness measurement> The thickness of the resulting colored coating film was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.). The results are shown in Table 3.

[0108] <Color evaluation> The obtained colored coating film on the glass substrate was subjected to spectrometry using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the absorbance at wavelengths of 525 nm and 565 nm was compared with the absorbance of the colored coating film of Comparative Example 1. The results are shown in Table 3. In Table 3, abs(525) represents the absorbance at a wavelength of 525 nm, and abs(565) represents the absorbance at a wavelength of 565 nm.

[0109] [Table 3]

[0110] As shown in Table 3, a colored coating film having strong absorption at a wavelength of 525 nm and extremely suppressed absorption at a wavelength of 565 nm was obtained from the colored curable resin compositions of Examples 1 and 2. Moreover, a colored coating film having very strong absorption at a wavelength of 525 nm while suppressing absorption at a wavelength of 565 nm caused by CI Pigment Red 254 was obtained from the colored curable resin compositions of Examples 3 and 4.

Claims

1. The composition comprises a colorant (A), a resin (B), a polymerizable compound (C) and a polymerization initiator (D), The colorant (A) contains a perylene compound (1) having an absorption maximum at 400 nm to 560 nm and no absorption maximum at more than 560 nm to 780 nm, and an isoindoline pigment (A1); The perylene compound (1) is a compound represented by formula (1-A): 【Chemistry 1】 [In formula (1-A), R 1 and R 2 each independently represent a methyl group having a carboxy group as a substituent, a branched alkyl group having 10 to 15 carbon atoms, or a monocyclic aromatic hydrocarbon group having 10 to 15 carbon atoms; R 3 to R 10 each independently represent a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.] A colored curable resin composition, comprising: a colorant (A) content of 30 mass% or less based on a total amount of solids in the colored curable resin composition.

2. The colored curable resin composition according to claim 1, wherein the colorant (A) further contains a pigment (A2-2) other than the perylene compound (1) and the isoindoline pigment (A1).

3. The colored curable resin composition according to claim 1 or 2, further comprising a solvent (E).

4. A color filter formed from the colored curable resin composition according to any one of claims 1 to 3.

5. A solid-state imaging device comprising the color filter according to claim 4 .

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