Curable composition, inkjet ink using the same, cured film, color filter, solid-state imaging element, and image display device

Abstract

To provide a curable composition that exhibits excellent properties such as a low rate of particle size change over time, high storage stability, excellent ejection performance, and a low rate of particle generation.SOLUTION: A curable composition comprises a colorant (A), a pigment derivative (B1) having a quinophthalone skeleton represented by General Formula (1), a pigment derivative (B2) having a quinophthalone skeleton, a polymerizable compound (C), and a polymerization initiator (D).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a curable composition, and an ink-jet ink, a cured film, a color filter, a solid-state imaging device, and an image display device each using the curable composition. [Background technology]

[0002] In recent years, a solventless inkjet recording method has been attracting attention, in which an ink that can be cured by irradiation with radiation such as ultraviolet light is applied to a desired material in an imagewise manner, and the applied ink is cured to record an image. In a curable composition used in an inkjet, it is important to ensure the dispersion stability of a colorant. If there is a problem with the dispersion stability, various problems occur, such as the deposition of aggregated foreign matter on a film and the deterioration of the ejection property of the inkjet ink. As a method for obtaining a stable inkjet ink, for example, Patent Document 1 proposes a composition using a pigment derivative. Also, Patent Document 2 discloses an inkjet ink using a quinophthalone derivative. However, although the inkjet inks disclosed in these documents have dispersion stability, there is room for improvement in terms of ejection stability and rate of change in particle size over time. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2004-18656 A [Patent Document 2] JP 2006-348205 A Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide a curable composition and an ink-jet ink that exhibit excellent properties such as a small rate of change in particle diameter over time, high storage stability, excellent dischargeability, and a low rate of foreign matter generation, as well as a film and a color filter using the same, and a solid-state imaging device and an image display device that are equipped with the color filter. [Means for solving the problem]

[0005] As a result of extensive research into solving the above-mentioned problems, the inventors have found that the above-mentioned problems can be solved by including two types of pigment derivatives having specific structures in a curable composition having a solvent content of 5.0 mass % or less, and have thus arrived at the present invention.

[0006] That is, the present invention provides a curable composition comprising a colorant (A), a pigment derivative (B1) represented by general formula (1), a pigment derivative (B2) represented by general formula (2), a polymerizable compound (C), and a polymerization initiator (D), wherein the content of a solvent in the curable composition is 5.0 mass% or less. The present invention relates to a curable composition.

[0007] The present invention also relates to the curable composition, wherein the polymerizable compound (C) contains a difunctional (meth)acrylate.

[0008] The present invention also relates to the curable composition, wherein the colorant (A) contains at least one pigment selected from the group consisting of phthalocyanine pigments, isoindoline pigments, azo metal complex pigments, quinophthalone pigments, diketopyrrolopyrrole pigments, and anthraquinone pigments.

[0009] The present invention also relates to the curable composition, wherein a mass ratio of the pigment derivative (B1) represented by general formula (1) to the pigment derivative (B2) represented by general formula (2) is 99.9:0.1 to 50.0:50.0.

[0010] In addition, the present invention relates to a pigment derivative (B1), wherein R 101 ~R 108At least one of the groups represented by the general formula (2) is a halogen atom, and the pigment derivative (B2) is 114 ~R 121 wherein one or more of the following is a halogen atom:

[0011] The present invention also relates to an inkjet ink comprising the curable composition.

[0012] The present invention also relates to a cured film formed from the curable composition.

[0013] The present invention also relates to a color filter having the cured film.

[0014] The present invention also relates to a solid-state imaging device comprising the above-mentioned color filter.

[0015] The present invention also relates to an image display device comprising the above color filter. Effect of the Invention

[0016] The present invention can provide a curable composition and an ink-jet ink that exhibit excellent properties such as a small rate of change in particle diameter over time, high storage stability, excellent dischargeability, and a low rate of foreign matter generation, as well as a film and a color filter using the same, and a solid-state imaging device and an image display device that are equipped with the color filter. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] Hereinafter, the embodiment for carrying out the curable composition of the present invention will be described in detail. Note that the present invention is not limited to the following embodiment, and can be modified within the scope of the problem that can be solved.

[0018] In this specification, unless otherwise specified, "(meth)acryloyl", "(meth)acrylic", "(meth)acrylic acid", "(meth)acrylate", "(meth)acryloyloxy", or "(meth)acrylamide" means "acryloyl and / or methacryloyl", "acrylic and / or methacrylic", "acrylic acid and / or methacrylic acid", "acrylate and / or methacrylate", "acryloyloxy and / or methacryloyloxy", or "acrylamide and / or methacrylamide", respectively. "CI" means "Color Index" (published by The Society of Dyers and Colourists).

[0019] <Colorant (A)> The curable composition of the present invention contains a colorant (A). The colorant (A) can be selected from various conventionally known pigments and dyes. Specific examples of the colorant (A) that can be used in the curable composition are shown below with their color index numbers.

[0020] Examples of red pigments include CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53:3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243 , 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 291, 295, or 296, pigments described in JP-A-2014-134712, pigments described in JP-A-6368844, and other red pigments can be used. Red dyes such as xanthene, azo, disazo, and anthraquinone dyes can also be used. Specific examples include salt-forming compounds of xanthene acid dyes such as CI Acid Red 52, 87, 92, 289, and 338. Among these, CI Pigment Red 177, 254, and 291 are preferred from the viewpoints of coloring power and storage stability.

[0021] As the orange pigment, orange pigments such as CI Pigment Orange 34, 36, 38, 43, 51, 55, 59, 61, 62, 64, 71, or 73 can be used.

[0022] Yellow pigments include CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, Yellow pigments such as 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 198, 199, 213, 214, 218, 219, 220, 221, 231, 233, or 234 can be used. Quinoline, azo, disazo, methine, and other yellow dyes can also be used. Among these, CI Pigment Yellow 138, 139, 150, 185, and 231 are preferred from the viewpoints of coloring power and storage stability.

[0023] Examples of green pigments that can be used include CI Pigment Green 7, 10, 36, 37, 58, 59, 62, and 63, zinc phthalocyanine pigments described in JP-A-2008-19383, JP-A-2007-320986, JP-A-2004-70342, and WO 2015 / 118720, and aluminum phthalocyanine pigments described in Japanese Patent No. 4893859. Among these, C. Green 7, I. Pigment 36, 58, 59, 62, and 63 are preferred from the viewpoint of coloring power and storage stability.

[0024] Blue pigments include, for example, CI Pigment Blue 1, 1:2, 1:3, 2, 2: Blue pigments such as 1, 2:2, 3, 8, 9, 10, 10:1, 11, 12, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 18, 19, 22, 24, 24:1, 53, 56, 56:1, 57, 58, 59, 60, 61, 62, 64, etc. can be used.

[0025] Purple pigments include, for example, CI Pigment Violet 1, 1:1, 2, 2:2, Examples of such ribozymes include, but are not limited to, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, and 50.

[0026] Inorganic pigments include titanium oxide, barium sulfate, zinc oxide, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron oxide (III)), cadmium red, ultramarine, iron blue, chromium oxide green, cobalt Examples of inorganic pigments include amber, red, and synthetic iron black. Inorganic pigments are used in combination with organic pigments to ensure good coatability, sensitivity, developability, and the like while maintaining a good balance between saturation and brightness.

[0027] From the viewpoint of storage stability, the colorant (A) preferably contains at least one selected from the group consisting of phthalocyanine pigments, isoindoline pigments, azo metal complex pigments, quinophthalone pigments, diketopyrrolopyrrole pigments, and anthraquinone pigments, and is particularly preferably a phthalocyanine pigment, an isoindoline pigment, an azo metal complex pigment, a quinophthalone pigment, or an anthraquinone pigment.

[0028] (Micronization of pigments) When the colorant (A) used in the curable composition of the present invention is a pigment, it is preferable to use it after it has been finely divided. The method of finely dividing is not particularly limited, and for example, any of wet grinding, dry grinding, and dissolution precipitation methods can be used. As exemplified in the present invention, it can be finely divided by carrying out salt milling treatment using a kneader method, which is a type of wet grinding. The average primary particle size of the pigment determined by TEM (transmission electron microscope) is preferably in the range of 5 to 90 nm. If it is smaller than 5 nm, dispersion becomes difficult, and if it is larger than 90 nm, the transmittance may decrease. For these reasons, the average primary particle size is more preferably in the range of 10 to 70 nm.

[0029] Salt milling is a process in which a mixture of a pigment, a water-soluble inorganic salt, and a water-soluble organic solvent is mechanically kneaded while being heated using a batch or continuous kneader such as a kneader, a two-roll mill, a three-roll mill, a ball mill, an attritor, a sand mill, or a planetary mixer, and then the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water. The water-soluble inorganic salt acts as a crushing aid, and the pigment is crushed during salt milling by utilizing the high hardness of the inorganic salt. By optimizing the conditions for salt milling the pigment, it is possible to obtain a pigment with a very fine primary particle size, a narrow distribution width, and a sharp particle size distribution.

[0030] As the water-soluble inorganic salt, sodium chloride, barium chloride, potassium chloride, sodium sulfate, etc. can be used, but sodium chloride (table salt) is preferred from the viewpoint of cost. From the viewpoints of both treatment efficiency and production efficiency, the water-soluble inorganic salt is preferably used in an amount of 50 to 2000 parts by weight, and most preferably 300 to 1000 parts by weight, per 100 parts by weight of the pigment.

[0031] The water-soluble organic solvent is a solvent that functions to wet the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (is miscible with) water and does not substantially dissolve the inorganic salt used. However, since the temperature rises during salt milling and the solvent becomes prone to evaporate, a high boiling point solvent with a boiling point of 120°C or more is preferable from the viewpoint of safety. For example, 2-methoxyethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene ...ethyl ether, liquid polypropylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol The water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by weight, and most preferably 50 to 500 parts by weight, based on 100 parts by weight of the pigment.

[0032] When the pigment is subjected to salt milling, a resin may be added as necessary. The type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, etc. can be used. The resin used is preferably solid at room temperature and insoluble in water, and more preferably partially soluble in the above organic solvents. The amount of the resin used is preferably in the range of 5 to 200 parts by weight per 100 parts by weight of the pigment.

[0033] <Pigment derivatives> The curable composition of the present invention contains a pigment derivative (B1) represented by general formula (1) and a pigment derivative (B2) represented by general formula (2). The pigment derivative (B1) and the pigment derivative (B2) are pigment derivatives having a quinophthalone skeleton.

[0034] Most of the pigment derivative is adsorbed to the colorant (A), but some may be free in the composition without being adsorbed. Here, the pigment derivative (B1) having a sulfonic acid group and the pigment derivative (B2) having a sulfonic acid group and a carboxyl group have different acidities. It is presumed that by including two types of pigment derivatives (B1) and (B2) having different acidities, the pigment derivatives interact with each other, and less pigment derivative is released, resulting in a curable composition with good dischargeability and storage stability. Furthermore, since the pigment derivatives (B1) and (B2) have the same quinophthalone skeleton, the interaction is stronger than when two types of pigment derivatives with different skeletons are used, so it is presumed that there is less aggregated foreign matter and the rate of change in particle size over time is also smaller.

[0035] (Pigment derivatives (B1)) The pigment derivative (B1) contained in the curable composition of the present invention is represented by the following general formula (1).

[0036] General formula (1) [ka] [In general formula (1), R 101 ~R 113 R each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO3H, or a metal salt or alkylammonium salt of -SO3H. 101 ~R 104 , and / or R 105 ~R 108 Adjacent groups of R may be joined together to form an aromatic ring which may have a substituent. 101 ~R 113 At least one of these is -SO3H or a metal salt or alkylammonium salt of -SO3H.

[0037] R in general formula (1) 101 ~R 113 This article explains:

[0038] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine.

[0039] Examples of the alkyl group which may have a substituent include linear or branched alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group, an n-octyl group, a stearyl group, and a 2-ethylhexyl group, as well as alkyl groups having a substituent such as a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2-dibromoethyl group, a 2,2,3,3-tetrafluoropropyl group, a 2-ethoxyethyl group, a 2-butoxyethyl group, a 2-nitropropyl group, a benzyl group, a 4-methylbenzyl group, a 4-tert-butylbenzyl group, a 4-methoxybenzyl group, a 4-nitrobenzyl group, and a 2,4-dichlorobenzyl group.

[0040] Examples of alkoxyl groups which may have a substituent include linear or branched alkoxyl groups such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutyloxy, tert-butyloxy, neopentyloxy, 2,3-dimethyl-3-pentoxy, n-hexyloxy, n-octyloxy, stearyloxy, and 2-ethylhexyloxy groups, as well as alkoxyl groups having a substituent such as trichloromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2,2,3,3-tetrafluoropropyloxy, 2,2-ditrifluoromethylpropoxy, 2-ethoxyethoxy, 2-butoxyethoxy, 2-nitropropoxy, and benzyloxy groups.

[0041] Examples of the aryl group which may have a substituent include aryl groups such as a phenyl group, a naphthyl group, and an anthranyl group, as well as aryl groups having a substituent such as a p-methylphenyl group, a p-bromophenyl group, a p-nitrophenyl group, a p-methoxyphenyl group, a 2,4-dichlorophenyl group, a pentafluorophenyl group, a 2-aminophenyl group, a 2-methyl-4-chlorophenyl group, a 4-hydroxy-1-naphthyl group, a 6-methyl-2-naphthyl group, a 4,5,8-trichloro-2-naphthyl group, an anthraquinonyl group, and a 2-aminoanthraquinonyl group.

[0042] R 101 ~R 113 At least one of these is SO3H or a metal salt or alkylammonium salt of -SO3H.

[0043] Examples of metal salts of -SO3H include salts of various metals such as sodium, potassium, calcium, barium, copper, zinc, magnesium, aluminum, nickel, cobalt, strontium, etc. Among these, aluminum salts are not only excellent in isolation properties during production and dispersibility as a pigment derivative, but also exhibit the most excellent effects in terms of low viscosity, flow properties, and viscosity stability over time.

[0044] Examples of the alkyl ammonium salt of -SO3H include lower amines such as dimethylamine, trimethylamine, diethylamine, triethylamine, hydroxyethylamine, dihydroxyethylamine, 2-ethylhexylamine, N,N-dimethylaminopropylamine, N,N-diethylaminopropylamine, and N,N-dibutylaminopropylamine; long-chain alkylamines having an alkyl group of 12 or more carbon atoms such as laurylamine, oleylamine, palmitylamine, stearylamine, and dimethyllaurylamine; and long-chain alkylamines having an alkyl group of 12 or more carbon atoms such as lauryltrimethylammonium, dilauryldimethylammonium, stearyltrimethylammonium, and distearyldimethylammonium. Among these, the most effective method is to use a long-chain alkylamine having an alkyl group of 12 or more carbon atoms, such as lauryl ammonium or stearyl ammonium.

[0045] The pigment derivative (B1) may have any structure as long as it has a structure represented by the general formula (1). 101 ~R 108 Preferably, the group has a halogen atom.

[0046] Examples of the pigment derivative (B1) include those shown below, but the present invention is not limited to these.

[0047] [ka]

[0048] (Pigment derivatives (B2)) The pigment derivative (B2) contained in the curable composition of the present invention is represented by the following general formula (2).

[0049] General formula (2) [ka] [In general formula (2), R 114 ~R 126 R each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO3H, or a metal salt or alkylammonium salt of -SO3H. 114 ~R 117 , and / or R 118 ~R 121 Adjacent groups of R may be joined together to form an aromatic ring which may have a substituent. 114 ~R 126 At least one of these is -SO3H or a metal salt or alkylammonium salt of -SO3H.

[0050] R 114 ~R 126 The alkyl group which may have a substituent, the alkoxy group which may have a substituent, and the aryl group which may have a substituent are each represented by R 101 ~R 113 This is similar to the description above.

[0051] The pigment derivative (B2) may have any structure as long as it has a structure represented by chemical formula (2). 114 ~R 121 Preferably, the group has a halogen atom.

[0052] Examples of the pigment derivative (B2) include those shown below, but the present invention is not limited to these.

[0053] [ka]

[0054] The mass ratio of the pigment derivative (B1) to the pigment derivative (B2) is preferably from 99.9:0.1 to 50.0:50.0, and from the viewpoints of storage stability and agglomerated foreign matter, is more preferably from 99.5:0.5 to 70.0:30.0.

[0055] The total content of the pigment derivative (B1) and the pigment derivative (B2) is preferably from 0.5 to 30 parts by mass, and more preferably from 1 to 20 parts by mass, based on 100 parts by mass of the colorant (A).

[0056] The curable composition of the present invention may contain a pigment derivative other than the pigment derivative (B1) and the pigment derivative (B2).

[0057] Pigment derivatives other than pigment derivative (B1) and pigment derivative (B2) are compounds having an acidic group, a basic group, a neutral group, etc. in the organic dye residue. Examples of pigment derivatives include compounds having an acidic substituent such as a sulfo group, a carboxy group, or a phosphate group, as well as amine salts thereof, sulfonamide groups, or compounds having basic substituents such as a tertiary amino group at the terminal, and compounds having a neutral substituent such as a phenyl group or a phthalimidoalkyl group. Examples of organic pigments include diketopyrrolopyrrole pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiazine indigo pigments, triazine pigments, benzimidazolone pigments, indole pigments such as benzoisoindole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments (excluding pigment derivative (B1) and pigment derivative (B2)), naphthol pigments, threne pigments, phthalocyanine pigments, metal complex pigments, and azo pigments such as azo, disazo, and polyazo.

[0058] <Polymerizable compound (C)> The curable composition of the present invention contains a polymerizable compound (C). The polymerizable compound (C) is not particularly limited, and conventionally known monofunctional, bifunctional, and trifunctional or higher polyfunctional monomers and oligomers can be used. The polymerizable compound (C) may be used alone or in combination of two or more kinds.

[0059] Examples of the monofunctional monomer include a monofunctional acrylic monomer and a monofunctional vinyl monomer. Specific examples of the compound include benzyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, (ethoxylated (or propoxylated) 2-phenoxyethyl (meth)acrylate, dicyclopentenyl (oxyethyl) (meth)acrylate, ... Diethylene glycol (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, 2-methoxyethyl (methacrylate, methoxytriethylene glycol Chole(meth)acrylate, 2-ethoxyethyl(methacrylate, ethoxyethoxyethyl(methacrylate, methoxydipropylene glycol(meth)acrylate , dipropylene glycol (meth)acrylate, nonylphenol EO modified acrylate, nonylphenol PO modified acrylate, o-phenylphenol EO modified acrylate, 2-ethylhexyl EO modified acrylate, β-carboxyethyl (meth)acrylate, trimethylolpropane formal (meth)acrylate, isoamyl (meth)acrylate, cyclohexyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isobornyl (meth)acrylate, norbornyl (meth)acrylate acrylate, dicyclopentanyl (meth)acrylate, isooctyl (meth)acrylate, Lauryl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 1,4-cyclohexanedimethanol (meth)acrylate, 2-hydroxy Monofunctional acrylic monomers such as diethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, acryloylmorpholine, and N-acryloyloxyethylhexahydrophthalimide, as well as N-vinylcaproic acid, Examples of the vinyl monomer include monofunctional vinyl monomers such as lactam, N-vinylpyrrolidone, and N-vinylformamide. These compounds may be used alone or in combination of two or more.

[0060] The polyfunctional monomer includes a compound having two or more polymerizable functional groups in the molecule, such as polyfunctional acrylic monomers other than 2-(2-vinyloxyethoxy)ethyl acrylate, vinyl monomers, and the like. Specific examples of the compound include dimethyloltricyclodecane di(meth)acrylate, ethoxylated bisphenol A di(meth)acrylate, and propoxylated bisphenol A. Di(meth)acrylate, cyclohexanedimethanol di(meth)acrylate, (poly ) Ethylene glycol di(meth)acrylate, (ethoxylated (or propoxylated)) 1 ,6-hexanediol di(meth)acrylate, 1,9-nonanediol acrylate, 1,10-decanediol diacrylate, (ethoxylated (or propoxylated)) neopentyl glycol di(meth)acrylate, hydroxypivalic acid neopentyl glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, (neopentyl glycol modified) trimethylolpropane di(meth)acrylate, tripropylene glycol di(meth)acrylate, dicyclopentanyl di(meth)acrylate, pentaerythritol tri(or tetra)(meth)acrylate, trimethylolpropane tri(or tetra)(meth)acrylate, tetramethylolmethane tri(or tetra)(meth)acrylate, and dipentaerythritol hexa(meth)acrylate. Another example of the polyfunctional monomer is a polyfunctional vinyl monomer containing a plurality of vinyl groups in the molecule.Specific examples of the compound include butanediol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, cyclohexane dimethanol divinyl ether, trimethylolpropane divinyl ether, pentaerythritol tri(or tetra)vinyl ether, trimethylolpropane diallyl ether, pentaerythritol tri(or tetra)allyl ether, etc.These compounds may be used alone or in combination of two or more kinds. "EO modified" means ethylene oxide modified, and "PO modified" means propylene oxide modified.

[0061] In particular, polymerizable compounds that dissolve polymeric dispersants and / or pigment derivatives are preferred. Specific examples include 2-phenoxyethyl acrylate, acryloylmorpholine, ethoxylated neopentyl glycol di(meth)acrylate, propoxylated neopentyl glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, isobornyl acrylate, phenoxydiethylene glycol acrylate, vinyl caprolactam, vinyl pyrrolidone, N-vinyl formamide, and 2-hydroxy-3-phenoxypropyl acrylate. Among these, 2-phenoxyethyl acrylate is preferred from the viewpoint of storage stability. It is preferred to include a functional (meth)acrylate, with dipropylene glycol diacrylate being particularly preferred.

[0062] In addition, from the viewpoint of storage stability and agglomerated foreign matter, when the pigment, pigment derivative, etc. are mixed and dispersed, it is preferable to add a bifunctional (meth)acrylate and allow it to adhere to the surface of the pigment, pigment derivative, etc. During the dispersion treatment, it is preferable that the mixture does not substantially contain a monofunctional (meth)acrylate.

[0063] The curable composition of the present invention preferably contains 2-(2-vinyloxyethoxy)ethyl acrylate as the polymerizable compound (C). 2-(2-vinyloxyethoxy)ethyl acrylate is commercially available as, for example, "VEEA" and "VEEA-AI" manufactured by Nippon Shokubai Co., Ltd. 2-(2-vinyloxyethoxy)ethyl acrylate has low viscosity and high reactivity. Therefore, it is excellent as a material for producing a curable composition with low viscosity and high sensitivity. The content of 2-(2-vinyloxyethoxy)ethyl acrylate is preferably 5 to 50 mass %, more preferably 5 to 35 mass %, based on the total weight of the curable composition.

[0064] <Polymerization initiator (D)> The curable composition of the present invention contains a polymerization initiator (D). The polymerization initiator that can be used in the present invention may be a known polymerization initiator. For example, it is preferable to use a polymerization initiator that generates radicals by molecular cleavage or hydrogen abstraction. In the present invention, the polymerization initiator (D) may be used alone or in combination of two or more kinds. In addition, a polymerization initiator that generates radicals and a polymerization initiator that generates cations may be used in combination.

[0065] Specific examples of the polymerization initiator (D) include 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 1-[4- (2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1-{ 4-[ 4-( 2-hydroxy-2-methyl-prop propionyl)-benzyl]-phenyl}-2-methyl-propan-1-one, phenyl α-Hydroxyalkylphenone compounds such as glyoxylic acid methyl ester; 2-Methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane- 1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butanon-1-one, 2-(dimethylamino)-2-[ α-Aminoalkylphenone compounds such as (4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone; acylphosphine oxide compounds such as bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide and 2,4,6-trimethylbenzoyl-diphenylphosphine oxide; 1,2-octanedione, 1-[4-(phenylthio)-2-(O-benzoyloxime), Oxime ester compounds such as 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1- (O-acetyloxime); Benzophenone 4 -phenylbenzophenone, isophthalphenone, 4-benzoyl-4'-methyl-diphenyl sulfide and other benzophenone compounds; 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-biphenyl-4,6-bis(trichloromethyl)-s-triazine, and triazine-based compounds such as 2-(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, and 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine.

[0066] Commercially available products include α-hydroxyalkylphenone compounds such as Omnirad 127, 184, 1173, and 2959 manufactured by IGM Resins, aminoalkylphenone compounds such as Omnirad 907, 369E, and 379EG manufactured by IGM Resins, acylphosphine oxide compounds such as Omnirad 819 and TPO manufactured by IGM Resins, and oxime ester compounds such as IRGACURE OXE-01, 02, 03, 04, and 05 manufactured by BASF Japan, ADEKA Arcles N-1919, NCI-730, 831E, and 930 manufactured by ADEKA, and TRONLY TR-PBG-301, 304, 305, 309, 314, 345, 358, and 359 manufactured by Changzhou Strong New Materials Co., Ltd. 80, 365, 610, 3054, 3057, Omnirad 1312, 1314, 1316 manufactured by IGM Resins, SPI-02, 03, 04, 05, 06, 07 manufactured by Samyang Corporation, DFI-020, 306, EOX-01 manufactured by Daito Chemistryx Co., Ltd., and the like. Among these, oxime ester compounds are preferred.

[0067] (Oxime ester compounds) When oxime ester compounds absorb ultraviolet light, the NO bond of the oxime is cleaved, generating iminyl radicals and alkyloxy radicals. These radicals further decompose to generate highly active radicals, making it possible to form patterns with a small amount of exposure. Oxime ester compounds have high quantum efficiency, resulting in coatings with high curing properties and few foreign matter.

[0068] Examples of the oxime ester compound include the oxime ester compounds described in JP 2007-210991 A, JP 2009-179619 A, JP 2010-037223 A, JP 2010-215575 A, JP 2011-020998 A, and WO 2021 / 175855.

[0069] The content of the polymerization initiator (D) in the curable composition is preferably from 2 to 20% by mass, and more preferably from 5 to 15% by mass. When an appropriate amount is added, the photocurability is further improved.

[0070] <Dispersant> The curable composition of the present invention may contain a dispersant for dispersing the colorant (A). For the dispersant, the descriptions in known documents such as JP2011-225848A can be appropriately referred to. Specifically, for example, Lubrizol's SOLSPERSE series (e.g. SOL SPERSE16000, 21000, 32000, 33000, 41000, J18 0, J200, etc.), BYK's DISPERBYK series (e.g. DISPE RBYK102, 110, 111, 118, 165, 168, 190, etc.), Evonik Examples include the TEGO Dispers series from the company (e.g. TEGO Dispers 610, 630, 651, 655 750W, 755W, etc.).

[0071] <Solvent> In order to reduce the viscosity of the curable composition and improve the wetting and spreading properties on the substrate, a small amount of solvent may be contained in the curable composition. The solvent is selected in consideration of the solubility of each component of the curable composition and further safety. The content of the solvent is 5.0 mass% or less in the curable composition from the viewpoint of curability. From the viewpoint of discharge stability, it is preferably 0.2 to 5.0 mass%, more preferably 0.5 to 4.0 mass%.

[0072] Of the above solvents, the boiling point of the solvent is preferably 120°C to 300°C, more preferably 140°C to 270°C. More preferred are monoacetates of glycol compounds, diacetates, etc. Examples of the monomer include acetates, diols, monoalkyl ethers, dialkyl ethers, and lactates. Among them, the monomers of glycol compounds, monoacetates, monoalkyl ethers, and dialkyl ethers, are preferred. More specifically, tetraethylene glycol dialkyl ether, ethylene glycol monobutyl ether acetate, and diethylene glycol diethyl ether are preferred.

[0073] <Sensitizer> The curable composition of the present invention may contain a sensitizer. Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, Polymethine dyes such as 1,2-diketone derivatives represented by benzil and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, and oxonol derivatives, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrin derivatives, Examples of the compound include pyrirazine derivatives, tetraquinoxalylporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine derivatives, thiospiropyran derivatives, metal arene complexes, organic ruthenium complexes, Michler's ketone derivatives, α-acyloxy esters, acylphosphine oxides, methylphenyl glyoxylates, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethyl anthraquinone, 4,4'-diethylisophthalophenone, 3,3' or 4,4'-tetra(t-butylperoxycarbonyl)benzophenone, and 4,4'-bis(diethylamino)benzophenone.

[0074] Among the above sensitizers, particularly suitable sensitizers include thioxanthone derivatives, Michler's ketone derivatives, and carbazole derivatives. More specifically, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole, and 3,6-dibenzoyl-N-ethylcarbazole are used.

[0075] More specifically, sensitizers described in "Dye Handbook" edited by Okawara Makoto et al. (Kodansha, 1986), "Chemistry of Functional Dyes" edited by Okawara Makoto et al. (CMC, 1981), "Tokushu No Futon Zairyo" edited by Ikemori Chuzaburo et al., and "Tokushu No Futon Zairyo" (CMC, 1986) are included, but are not limited to these. In addition, sensitizers that absorb light from ultraviolet to near infrared regions can also be contained. The sensitizers can be used alone or in combination of two or more types.

[0076] <Polymerization inhibitor> The curable composition of the present invention may contain a polymerization inhibitor in order to improve viscosity stability over time, ejection stability after aging, and viscosity stability in an inkjet recording device. As the polymerization inhibitor, a hindered phenol compound, a phenothiazine compound, a hindered amine compound, or a phosphorus compound is particularly preferably used. Specifically, 4-methoxyphenol, hydroquinone, methylhydroquinone, t-butylhydroquinone, 2,6 -di-t-butyl-4-methylphenol, phenothiazine, aluminum salt of N-nitrosophenylhydroxylamine, etc. From the viewpoint of maintaining the curability while improving the stability over time, it is preferably blended in a proportion of 0.01 to 2 mass % based on the entire curable composition.

[0077] <Antioxidants> The curable composition of the present invention may contain an antioxidant. The antioxidant prevents the polymerization initiator contained in the curable composition from being oxidized and yellowed, and therefore can improve the transmittance of the coating film.

[0078] Examples of the antioxidant include hindered phenol-based, hindered amine-based, phosphorus-based, sulfur-based, and hydroxylamine-based compounds. In the present invention, the antioxidant is preferably a compound that does not contain a halogen atom.

[0079] Among these, from the viewpoint of achieving both the transmittance and the sensitivity of the coating film, hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants are preferred.

[0080] The antioxidants can be used alone or in combination of two or more kinds.

[0081] The content of the antioxidant is more preferably 0.5 to 5.0% by mass relative to 100% by mass of the solid content of the curable composition, since this leads to good transmittance and spectral characteristics.

[0082] <Surface conditioner> The curable composition of the present invention may contain a surface conditioner. The surface conditioner described in this specification means a substance that reduces the surface tension of the curable composition by adding it. Examples of the surface conditioner include silicone-based surface conditioners, fluorine-based surface conditioners, acrylic surface conditioners, and acetylene glycol-based surface conditioners. From the viewpoint of the ability to reduce surface tension and compatibility with polymerizable compounds, it is preferable to use silicone-based surface conditioners.

[0083] Specific examples of silicone-based surface conditioners include modified dimethylsiloxane skeletons. Among them, polyether-modified siloxane-based surface conditioners are preferred. The polyether may be, for example, polyethylene oxide and polypropylene oxide. In one embodiment of the present invention, commercially available polyether-modified silicone-based surfactants can be used. Representative examples of products that can be preferably used include polyether-modified siloxanes such as BYK (registered trademark-378, 348, and 349) from BYK-Chemie; and Examples of the polyether-modified polydimethylsiloxane include BYK-UV3500 and UV3510. Also, TEGO (registered trademark) GLIDE450 and 450 from Evonik Degussa are listed. Examples of the polyether-modified siloxane copolymers include BYK-331, 378, 348, UV3510, TEGOGLIDE 450, 435, 432, 410, 406, 130, 110, and 100. Among these, from the viewpoint of forming a good image, BYK-331, 378, 348, UV3510, TEGOGLIDE 450, 4 Polyether modified silicone surface conditioners such as 40, 432, and 410 are preferred.

[0084] The content of the silicone surface conditioner is 0.1 to 5.0% by weight based on the total weight of the curable composition. The range of % by weight is preferable. By making the content 0.1% by weight or more, the wettability of the curable composition to the substrate can be easily improved. On the other hand, by making the content 5.0% by weight or less, the storage stability of the curable composition can be easily ensured.

[0085] <Storage stabilizer> The curable composition of the present invention may contain a storage stabilizer to stabilize the viscosity of the composition over time. Examples of storage stabilizers include quaternary ammonium chlorides such as benzyl trimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, organic phosphines such as t-butylpyrocatechol, tetraethylphosphine and tetraphenylphosphine, and phosphites. The storage stabilizer may be used in an amount of 0.1 to 10% by mass based on the total amount of the colorant (A) (100% by mass).

[0086] <Other ingredients> The curable composition of the present invention may contain other components in addition to those described above. The other components may include, for example, , a binder resin, a thermal crosslinking agent, a curing agent, a curing accelerator, an acid generator, a curing catalyst, a chain transfer agent, a silane coupling agent, and a near infrared absorbing agent. The content of the other components can be appropriately set within a range in which the problem of the present invention can be solved.

[0087] <Method of preparing curable composition> The curable composition of the present invention can be prepared by adding a polymerizable compound (C), a polymerization initiator (D), etc. to a colorant dispersion prepared by finely dispersing the colorant (A), the pigment derivative (B1), and the pigment derivative (B2) together with a colorant carrier such as a dispersant and a polymerizable compound (C) using various dispersing means such as a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor, and diluting the colorant dispersion. When preparing a colorant dispersion, two or more types of colorants may be dispersed simultaneously in a colorant carrier, or the colorants separately dispersed in colorant carriers may be mixed. When the solubility of a colorant such as a dye is high, specifically, when the solubility in the polymerizable compound (C) used is high, and the colorant is dissolved by stirring and no foreign matter is confirmed, it is not necessary to prepare the colorant dispersion by finely dispersing it as described above.

[0088] <Water content> From the viewpoint of stability, the curable composition of the present invention preferably has a water content of 2.0% by mass or less.

[0089] The water content in the curable composition is more preferably 1.5 mass % or less, particularly preferably 1.0 mass % or less. The lower limit of the water content is preferably as low as possible, and there is no particular restriction.

[0090] The method for controlling the water content is not particularly limited, and a known method can be used. For example, the above-mentioned components are sufficiently dried to reduce the amount of water contained in the components. In addition, a method of producing a curable composition while blowing in dry air, an inert gas, or a mixed gas thereof can be used.

[0091] <Specific metal atoms> The curable composition of the present invention may contain small amounts of metal components including Li, Na, Mg, K, Cs, Co, Ca, Fe, Si and Zr (hereinafter also referred to as specific metal atoms) in addition to the constituents of the colorant (A), the pigment derivatives (B1) and (B2), the polymerizable compound (C) and the polymerization initiator (D). If a large amount of metal components including these specific metal atoms are present, the storage stability may be impaired, the heat resistance may be reduced, or the dischargeability may be deteriorated. In addition, a color filter produced using a curable composition containing a large amount of metal components containing such specific metal atoms may generate foreign matter, which may result in a decrease in transmittance. The total content of the specific metal atoms in the metal components contained in the curable composition of the present invention is preferably 1 to 1000 ppm by mass with respect to the entire curable composition.

[0092] <Average dispersed particle size> The average dispersed particle size (secondary particle size) of the particles in the curable composition is preferably from 10 to 300 nm, more preferably from 30 to 250 nm. If the particles have an appropriate particle size, a curable composition having high dispersion stability is easily obtained.

[0093] The average dispersed particle size (secondary particle size) is measured, for example, using Nikkiso Microtrack UPA-EX150, which employs dynamic light scattering (FFT power spectrum method), with particle permeability set to absorption mode, particle shape set to non-spherical, and D50 particle size set to average size. The dilution solvent used for measurement is the same as that used for dispersion, and it is preferable to measure samples treated with ultrasound immediately after sample preparation, as this tends to give results with less variation.

[0094] <Removal of large particles> The curable composition is preferably subjected to removal of coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably coarse particles of 0.5 μm or more, and mixed dust by means of centrifugation, filtration with a sintered filter or membrane filter, etc. The curable composition of the present invention preferably does not substantially contain particles of 0.5 μm or more, and more preferably does not contain particles of 0.3 μm or less.

[0095] <Inkjet ink> The curable composition of the present invention can be made into an inkjet ink by appropriately adjusting the composition. There is no particular limitation on the use of the inkjet ink, but it is preferably used as an inkjet ink for color filters.

[0096] The inkjet ink of the present invention is preferably adjusted to have a viscosity of 5 to 50 mPa·s at 25° C. If the viscosity is in this range, the inkjet ink has excellent discharge followability and stability.

[0097] <Printing method> The inkjet ink of the present invention has excellent curing properties and can be used in a single-pass printing method, which successively comprises, for example, an ink ejection mechanism having one or more inkjet heads, a mechanism for transporting the substrate on which the ink has landed at a desired speed, and a mechanism for curing the ink by irradiating it with active energy rays such as a UV lamp or electron beam.

[0098] The optimum ink film thickness is preferably from 2 μm to 30 μm, more preferably from 3 μm to 25 μm, and even more preferably from 4 μm to 20 μm. Within the above range, good color development and curing properties are obtained.

[0099] Inkjet head The inkjet head used in the inkjet printing method may be of an on-demand type or a continuous type. In addition, the ejection method may be an electro-mechanical conversion method. type (e.g., single cavity type, double cavity type, bender type, piston type, share mode type, shared wall type, etc.), electric-thermal conversion type (e.g., thermal inkjet type, bubble jet (registered trademark type, etc.), electrostatic attraction type (e.g., electric field Control type, slit jet type, discharge type (e.g. spark jet type, etc.) As a concrete example, any ejection method may be used.

[0100] Ink Droplet Size The volume of the ink droplets ejected from the inkjet head is within the range of 0.5 to 100 pL. From the viewpoint of reducing unevenness in coating and increasing the printing speed, it is preferable to set the range of 2 to 100%. More preferably, it is in the range of 20 pL.

[0101] <Printing method> There are two types of printing methods using inkjet printing: one-pass printing and multi-pass printing. One-pass printing is a method in which multiple inkjet heads are fixedly positioned in a specified printing area and printing is performed with one head scan. In contrast, multi-pass printing (also called the serial printing method) is a method in which a specified printing area is printed with multiple head scans.

[0102] In the one-pass printing method, it is preferable to use a wide head in which nozzles are arranged in a row over a width equal to or greater than the width of the desired coating pattern. When forming a plurality of independent coating patterns that are not continuous with each other on the same substrate, it is preferable to use a wide head in which nozzles are arranged in a row over a width equal to or greater than the width of each coating pattern. Simply use the wide head above.

[0103] The active energy rays for curing the inkjet ink may be any energy rays that can affect the electron orbit of the irradiated object and induce polymerization reactions of radicals, cations, anions, etc. Although not particularly limited, specific examples include electron beams, ultraviolet rays, and infrared rays. In the present invention, ultraviolet rays are preferably used.

[0104] Examples of light sources that can be used for ultraviolet rays include high-pressure mercury lamps, metal halide lamps, low-pressure mercury lamps, ultra-high-pressure mercury lamps, ultraviolet lasers, LEDs, and sunlight. In terms of convenience and cost, high-pressure mercury lamps, metal halide lamps, and LEDs are used. The maximum emission wavelength is preferably 200 to 600 nm, more preferably 300 to 450 nm, and further preferably 320 to 420 nm. It is particularly preferable that the ultraviolet light be in the range of 340 to 400 nm.

[0105] <Color filters> The color filter of the present invention has a substrate and the cured film of the present invention. The color filter of the present invention comprises at least one red filter segment, at least one green filter segment, and at least one blue filter segment, and may further comprise a yellow filter segment in addition to the above three color filter segments.

[0106] <Manufacturing method for color filters> The color filter of the present invention can be produced by a printing method.

[0107] The formation of filter segments by printing method is excellent in terms of low cost and mass productivity as a method for producing color filters, since a pattern can be formed by printing a curable composition prepared as an inkjet ink. Furthermore, the development of printing technology has made it possible to print fine patterns with high dimensional accuracy and smoothness. In order to perform printing, it is preferable to use a composition that does not allow the ink to dry or solidify on the printing plate or blanket. In addition, control of the fluidity of the ink on the printing machine is also important, and the ink viscosity can be adjusted by using a dispersant or an extender pigment.

[0108] <Solid-state imaging element> The solid-state imaging element of the present invention has the color filter. The form used for the solid-state imaging element is not particularly limited, but for example, a substrate is provided with a plurality of photodiodes constituting a light receiving area of ​​a solid-state imaging element (CCD image sensor, CMOS image sensor, etc.) and a transfer electrode made of polysilicon or the like, a light-shielding film having an opening only for the light receiving portion of the photodiode on the photodiode and the transfer electrode, a device protection film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire light-shielding film and the light receiving portion of the photodiode, and a filter on the device protection film. Furthermore, the device protection film may have a configuration in which a light-collecting means (e.g., a microlens, etc., the same below) is provided on the device protection film and below the filter (the side closer to the substrate), or a configuration in which a light-collecting means is provided on the filter. The filter may have a structure in which a cured film forming each color pixel is embedded in a space partitioned, for example, in a lattice shape by partition walls. In this case, the partition walls preferably have a low refractive index with respect to each color pixel. An imaging device including a solid-state imaging element of the present invention can be used for various purposes such as digital cameras, electronic devices with imaging functions (smartphones, tablet terminals, etc.), vehicle-mounted cameras, surveillance cameras, and optical sensors.

[0109] <Image display device> The image display device of the present invention has the above-mentioned color filter. Examples of the display device include a liquid crystal display and an organic EL display. The form of the display device is not particularly limited, and the display device can be used as a color filter, a black matrix, a light-shielding filter, an infrared cut filter, or an infrared transmission filter. The form of the image display device is not particularly limited as long as it functions as an image display device. For example, the configuration described in "Next Generation Liquid Crystal Display Technology" (by Tatsuo Uchida, published by Kogyo Chosakai Co., Ltd. in 1994) can be mentioned. The definition of image display devices and details of each image display device are described, for example, in "Electronic Display Devices" (written by Sasaki Akio, published by Kogyo Chosakai Co., Ltd. in 1990) and "Display Devices" (written by Ibuki Yoshiaki, published by Sangyo Tosho Co., Ltd. in 1989). EXAMPLES

[0110] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these. In addition, "parts" means "parts by mass" and "%" means "% by mass".

[0111] (Method of Identifying Compounds (Q-1) and (Q-2)) To identify the compounds (Q-1) and (Q-2) of the present invention, MALDI TOF-MS spectroscopy (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry) was used. The MALDI TOF-MS spectrum was obtained using a Bruker Daltonics MALDI mass spectrometer Autoflex III, and the molecular ion peaks of the obtained mass spectrum and the calculated The compound obtained was identified based on the match of the mass number obtained by the above method.

[0112] (Method of identifying pigment derivatives) The pigment derivative (B1) and pigment derivative (B2) used in the examples of the present invention were dissolved in DMF and analyzed using an LC / MS analyzer manufactured by Nihon Waters, Inc. The obtained compounds were identified based on the agreement between the chromatographic peak at 420 nm and the mass number obtained by calculation. The LC measurement conditions are as follows. Equipment: Japan Waters ACQUITY UPLC H-Class Japan Waters Xevo TQD Column: ACQUITY UPLC BEH C18 (Nihon Waters Co., Ltd.) Eluent: (A) 0.05 mol / l CH3COONH4 aqueous solution, adjusted to pH 4.5 with acetic acid (B)DMF Gradient conditions: After holding the ratio at (A):(B) = 80 / 20 (volume ratio) for 1 minute, the ratio was changed from (A):(B) = 80 / 20 (volume ratio) to (A):(B) = 5 / 95 (volume ratio) over the course of 5 minutes, held at (A):(B) = 5 / 95 (volume ratio) for 3 minutes, and then held at (A):(B) = 80 / 20 (volume ratio) for 7 minutes. Flow rate: 0.40ml / min Flow time: 15 minutes Injection volume: 1μl Column temperature: 40℃

[0113] (Weight average molecular weight (Mw) of dispersant) The weight average molecular weight (Mw) of the dispersant is the polystyrene-equivalent weight average molecular weight (Mw) measured using a TSKgel column (manufactured by Tosoh Corporation) and a GPC (manufactured by Tosoh Corporation, HLC-8120GPC) equipped with an RI detector, using a solution of 3 mM triethylamine and 10 mM LiBr in N,N-dimethylformamide as the developing solvent.

[0114] (Amine value of dispersant) The amine value of the dispersant was determined by potentiometric titration using a 0.1N aqueous hydrochloric acid solution, and then converted into the equivalent amount of potassium hydroxide. The amine value of the dispersant indicates the amine value of the non-volatile portion.

[0115] (Quaternary ammonium salt value of dispersant) The quaternary ammonium salt value of the dispersant was determined by titration with 0.1N silver nitrate solution using 5% potassium chromate solution as an indicator, and then converted into the potassium hydroxide equivalent. The quaternary ammonium salt value of the dispersant below indicates the quaternary ammonium salt value of the non-volatile content.

[0116] <Synthesis of pigment derivatives> (Synthesis of pigment derivative (B1-1)) 50 parts of quinophthalone-based yellow pigment CI Pigment Yellow 138 (BASF's "Paliotol Yellow K0960-HD") was dissolved in 500 parts of 101% sulfuric acid and stirred at 70°C for 8 hours to carry out a sulfonation reaction. The end point of the reaction was determined by measuring the spectroscopic spectrum of the sulfuric acid solution and determining the point at which no change in the spectrum was observed. Next, this reaction solution was poured into 5,000 parts of stirred ice water, and the precipitate was filtered and washed with water. It was dried at 80°C to obtain a pigment derivative (B1-1). Identification was performed by mass spectrometry using LC-MS.

[0117] Pigment derivatives (B1-1) [ka]

[0118] (Synthesis of pigment derivative (B1-2)) 69.0 parts of the aqueous paste of the pigment derivative (B1-1) (water content: 85.5%) was added to 500 parts of water, stirred and redispersed, and then dissolved by adjusting the pH to 10 using 25% caustic soda solution. 9.6 parts of an 8% aqueous solution of aluminum chloride hexahydrate was gradually added to this solution. Precipitates appeared one after another from the dropwise addition points, and the pH gradually decreased with the addition. No bleeding was observed after the addition was completed. The precipitates were filtered out of the slurry, washed with water, and dried at 80°C to obtain the pigment derivative (B1-2).

[0119] (Synthesis of pigment derivative (B1-3)) Pigment derivative (B1-3) was obtained by carrying out the same procedure as in the synthesis of pigment derivative (B1-2), except that 12.3 parts of 8% aqueous zinc chloride hydrate solution was used instead of 9.6 parts of the 8% aqueous aluminum chloride hexahydrate solution used in the synthesis of pigment derivative (B1-2).

[0120] (Synthesis of pigment derivative (B1-4)) 200 parts of methyl benzoate were added with 47.5 parts of 8-aminoquinaldine, 90.1 parts of tetrachlorophthalic anhydride, and 183.2 parts of benzoic acid, and the mixture was heated to 120°C and stirred for 4 hours while distilling off water. Next, 62.4 parts of 2,3-naphthalenedicarboxylic anhydride were added to the reaction mixture, and the mixture was heated to 180°C and stirred for 4 hours while distilling off water. After cooling to room temperature, the reaction mixture was poured into 1200 parts of ethanol and stirred at room temperature for 1 hour. The precipitated crystals were filtered, washed with ethanol, and dried under reduced pressure to obtain 74.6 parts of compound (Q-1) (yield: 96%). Identification was performed by mass spectrometry using TOF-MS. Ta.

[0121] Compound (Q-1) [ka]

[0122] Pigment derivative (B1-4) was obtained by carrying out the same procedure as in the synthesis of pigment derivative (B1-1), except that 50 parts of compound (Q-1) obtained above was used instead of 50 parts of CI Pigment Yellow 138 (BASF's "Paliotol Yellow K0960-HD") used in the synthesis of pigment derivative (B1-1).

[0123] Pigment derivatives (B1-4) [ka]

[0124] (Synthesis of pigment derivative (B1-5)) 70.0 parts of the water paste of the pigment derivative (B1-4) (water content: 83.0%) was added to 500 parts of water, stirred and redispersed, and then dissolved by adjusting the pH to 10 using 25% caustic soda solution. 5.2 parts of an 8% aqueous solution of coconut oil amine acetate (product name: Acetamine 2-4, manufactured by Kao Corporation) was gradually added to this solution. Precipitates appeared one after another from the dropwise addition points, and the pH gradually decreased with the addition. No bleeding was observed after the addition was completed. The precipitates were filtered out of the slurry, washed with water, and dried at 80°C to obtain the pigment derivative (B1-5).

[0125] (Synthesis of pigment derivative (B1-6)) 200 parts of methyl benzoate were added with 47.5 parts of 8-aminoquinaldine, 120.2 parts of 5,7,8-trichloro-6-sulfo-2,3-naphthalenedicarboxylic anhydride, and 183.2 parts of benzoic acid, and the mixture was heated to 120°C and stirred for 6 hours while distilling off water. Next, 51.1 parts of 4-methylphthalic anhydride were added to the reaction mixture, and the mixture was heated to 180°C and stirred for 5 hours while distilling off water. After cooling to room temperature, the reaction mixture was poured into 1200 parts of ethanol and stirred at room temperature for 1 hour. The precipitated crystals were filtered off, washed with ethanol and then with water, and dried at 80°C to obtain a pigment derivative (B1-6). Identification was performed by mass spectrometry using LC-MS.

[0126] Pigment derivatives (B1-6) [ka]

[0127] (Synthesis of pigment derivative (B1-7)) 200 parts of methyl benzoate were added with 47.5 parts of 8-aminoquinaldine, 97.8 parts of phthalic anhydride, and 183.2 parts of benzoic acid, and the mixture was heated to 180°C and stirred for 5 hours while distilling off water. After cooling to room temperature, the reaction mixture was poured into 1200 parts of ethanol and stirred at room temperature for 1 hour. The precipitated crystals were filtered off, washed with ethanol, and dried under reduced pressure to obtain 111.7 parts of compound (Q-2) (yield: 89%). Identification was performed by mass spectrometry using TOF-MS.

[0128] Compound (Q-2) [ka]

[0129] 50 parts of the compound (Q-2) obtained above was dissolved in 500 parts of 100% sulfuric acid, and the mixture was stirred at 80°C for 10 hours to carry out a sulfonation reaction. The end point of the reaction was determined by measuring the spectroscopic spectrum of the sulfuric acid solution, and the point at which no change in the spectrum was observed was determined. Next, this reaction solution was poured into 5,000 parts of stirred ice water, and the precipitate was filtered off, washed with water, and dried under reduced pressure to obtain a pigment derivative (B1-7). Identification was performed by mass spectrometry using LC-MS.

[0130] Pigment derivatives (B1-7) [ka]

[0131] (Synthesis of pigment derivative (B2-1)) 69.0 parts of the aqueous paste of the pigment derivative (B1-1) (water content: 85.5%) was added to 500 parts of water and stirred to redisperse, after which 25% caustic soda solution was added with stirring to adjust the pH to 11. The pH was adjusted to 11.5. During the pH adjustment, the reaction mixture changed from a yellow slurry to a red solution. The pH was finely adjusted every 5 minutes and the reaction was continued for 1 hour. The pH was then adjusted to 11.5 at 50 °C. The mixture was heated to 50° C. and stirred for 3 hours. A 25% aqueous hydrochloric acid solution was gradually added dropwise to this red solution to adjust the pH to 3.5, obtaining a yellow precipitate. The yellow precipitate was filtered, washed with a large amount of water, and then dried at 80° C. to obtain 40 parts of a pigment derivative (B2-1). Identification was performed using LC-MS. This was analyzed by mass spectrometry using MS.

[0132] (Pigment derivatives (B2-1)) [ka]

[0133] (Synthesis of pigment derivative (B2-2)) 69.0 parts of the aqueous paste of the pigment derivative (B1-1) (water content: 85.5%) was added to 500 parts of water, stirred and redispersed, and then the pH was adjusted to 11.5 using 25% caustic soda solution. During the pH adjustment, the reaction solution changed from a yellow slurry state to a red solution state. Every 5 minutes The pH was finely adjusted and the stirring was continued for 1 hour. The solution was then heated to 50°C at pH 11.5 and stirred for 3 hours. 18.2 parts of an 8% aqueous solution of aluminum chloride hexahydrate was gradually added to this red solution. Precipitates appeared one after another from the dropwise addition points, and the pH gradually decreased to 3.8 with the addition. The precipitate was filtered off, washed with a large amount of water, and then dried at 80°C, and 44 parts of pigment were added. The derivative (B2-2) was obtained.

[0134] (Synthesis of pigment derivative (B2-3)) 69.0 parts of the aqueous paste of the pigment derivative (B1-1) (water content: 85.5%) was added to 500 parts of water, stirred and redispersed, and then adjusted to pH 11.5 using 25% caustic soda solution. During the pH adjustment, the reaction liquid changed from a yellow slurry state to a red solution state. The pH was finely adjusted every 5 minutes and the reaction was continued for 1 hour. The mixture was then heated to 50°C at pH 11.5 and stirred for 3 hours. 24.0 parts of an 8% aqueous zinc chloride solution was gradually added to this red solution. Precipitates appeared one after another from the dropwise addition points, and the pH gradually decreased to 3.7 with the addition. The precipitates were filtered off, washed with a large amount of water, and dried at 80°C to obtain 42 parts of the pigment derivative (B2 -3).

[0135] (Synthesis of pigment derivative (B2-4)) 70.0 parts of water paste of compound (Q-1) (water content: 85.0%) was added to 500 parts of water, stirred and redispersed, and then adjusted to pH 11.5 using 25% caustic soda solution. During the pH adjustment, the reaction solution changed from a yellow slurry state to a red solution state. The pH was finely adjusted every 5 minutes and continued for 1 hour. The mixture was then heated to 50°C at pH 11.5 and stirred for 3 hours. A 25% aqueous hydrochloric acid solution was gradually added dropwise to this red solution to adjust the pH to 3.5. The yellow precipitate was filtered off, washed with a large amount of water, and then dried at 80 °C. After drying, 41 parts of pigment derivative (B2-4) was obtained. Identification was performed by mass spectrometry using LC-MS.

[0136] (Pigment derivatives (B2-4)) [ka]

[0137] (Synthesis of pigment derivative (B2-5)) 70.0 parts of an aqueous paste of compound (Q-1) (water content: 85.0%) was added to 500 parts of water, stirred and redispersed, and then the pH was adjusted to 11.5 using 25% caustic soda solution. During the pH adjustment, the reaction solution changed from a yellow slurry state to a red solution state. The pH was finely adjusted every 5 minutes and the reaction was continued for 1 hour. The mixture was then heated to 50°C at pH 11.5 and stirred for 3 hours. 10.5 parts of an 8% aqueous solution of coconut oil amine acetate (trade name: Acetamine 24, Kao Corporation) was gradually added to this red solution. Precipitates appeared one after another from the points where the drops were added. The pH gradually decreased to 3.9 with the addition. The yellow precipitate was filtered off, washed with a large amount of water, and dried at 80° C. to obtain 43 parts of a pigment derivative (B2-5).

[0138] (Synthesis of pigment derivative (B2-6)) 70.0 parts of the aqueous paste of the pigment derivative (B1-6) (water content: 84.5%) was added to 500 parts of water and stirred to redisperse, after which 25% caustic soda solution was added with stirring to adjust the pH to 11.5. During the pH adjustment, the reaction solution changed from a yellow slurry state to a red solution state. The pH was finely adjusted every 5 minutes and continued for 1 hour. The reaction was then continued for 50 minutes at pH 11.5. The mixture was heated to ℃ and stirred for 3 hours. 25% hydrochloric acid solution was gradually added dropwise to the red solution. The pH was adjusted to 3.5 to obtain a yellow precipitate. The yellow precipitate was filtered off, washed with a large amount of water, and then dried at 80°C to obtain 40 parts of a pigment derivative (B2-6). The analysis was performed using mass spectrometry by -MS.

[0139] (Pigment derivatives (B2-6)) [ka]

[0140] (Synthesis of pigment derivative (B2-7)) 67.0 parts of the aqueous paste of the pigment derivative (B1-7) (water content: 85.2%) was added to 500 parts of water and stirred to redisperse, after which 25% caustic soda solution was added with stirring to adjust the pH to 11.5. During the pH adjustment, the reaction solution changed from a yellow slurry state to a red solution state. The pH was finely adjusted every 5 minutes and continued for 1 hour. The reaction was then continued for 50 minutes at pH 11.5. The mixture was heated to ℃ and stirred for 3 hours. A 25% aqueous solution of hydrochloric acid was added dropwise to the red solution. The mixture was cooled to room temperature, and the pH was adjusted to 3.5 to obtain a yellow precipitate. The yellow precipitate was filtered off, washed with a large amount of water, and then dried at 80° C. to obtain 40 parts of a pigment derivative (B2-7). Identification was performed by mass spectrometry using LC-MS.

[0141] (Pigment derivatives (B2-7)) [ka]

[0142] (Synthesis of Dispersant (E-1)) In a reaction vessel equipped with a stirrer and a thermometer, 41 parts of N,N-dimethylpropanediamine and 120 parts of chloroform were charged and stirred at room temperature, and 50 parts of methacrylic acid chloride were added dropwise over 1 hour. After stirring at room temperature for 3 hours, 1 After confirming the completion of the reaction by H-NMR, the reaction solution was washed successively with 300 parts of ion-exchanged water and 200 parts of saturated saline, and then 20 g of magnesium sulfate was added to the organic layer, stirred, and then filtered. The solvent in the obtained solution was distilled off with a rotary evaporator, and 58 parts of compound [B] represented by the following formula (15) was obtained as a pale yellow transparent liquid (yield 85%). The obtained compound was identified as follows: 1 H-NMR was performed.

[0143] Formula (15) [ka]

[0144] In a reaction vessel equipped with a gas inlet tube, a condenser, an agitator, and a thermometer, 15.7 parts of methyl methacrylate, 47.2 parts of n-butyl methacrylate, and 13.2 parts of tetramethylethylenediamine were charged, and the mixture was stirred at 50°C for 1 hour while flowing nitrogen, and the inside of the system was replaced with nitrogen. Next, 2.6 parts of ethyl bromoisobutyrate, 5.6 parts of cuprous chloride, and 100 parts of propylene glycol monomethyl ether acetate (hereinafter, PGMAc) were charged, and the temperature was raised to 110°C under a nitrogen stream to initiate polymerization of the first block. After polymerization for 4 hours, the polymerization solution was sampled and the solid content was measured, and it was confirmed that the polymerization conversion rate was 98% or more based on the non-volatile content. Next, 25 parts of PGMAc and 30.3 parts of the above compound [B] as the second block monomer were added to the reaction vessel, and the reaction was continued by stirring while maintaining the temperature at 110°C under a nitrogen atmosphere. Two hours after the addition of the compound [B] represented by the above formula (15), a sample of the polymerization solution was taken and the solid content was measured, and it was confirmed that the polymerization conversion rate of the second block was 98% or more, calculated from the non-volatile content. Further, 6.8 parts of benzyl chloride was added to the reaction vessel, and the mixture was stirred for 3 hours while maintaining the temperature at 110° C. under a nitrogen atmosphere, and then cooled. The block copolymer solution synthesized above was vacuum dried at 40°C to obtain a dispersant (E-1) in the form of a white powder having an amine value of 70 mgKOH / g, a quaternary ammonium salt value of 30 mgKOH / g, and a weight average molecular weight (Mw) of 9,800.

[0145] <Production of Curable Composition> [Production Example 1] (Pigment Dispersion (d-1)) A mixture of the following composition was stirred and mixed uniformly using a high-speed mixer or the like, and the resulting mill base was then dispersed in a horizontal sand mill for about 1 hour to prepare a pigment dispersion. CI Pigment Yellow 139 13.5 parts Pigment derivative (B1-1) 1.2 parts Pigment derivative (B1-2) 0.3 parts SOLSPERSE32000 7.5 copies Dipropylene glycol diacrylate 47.5 parts

[0146] [Production Examples 2 to 33, Comparative Production Examples 1 to 3] (Pigment Dispersions (d-2) to (d-36)) The following pigment dispersions (d-2) to (d-36) were prepared in the same manner as for the pigment dispersion (d-1), except that the colorant (A), pigment derivative, dispersant, and polymerizable compound (C) were changed to the compositions and amounts shown in Table 1.

[0147] [Table 1]

[0148] Meaning of abbreviations in Table 1 <Colorant (A)> "PY139"; CI Pigment Yellow 139 "PR177"; CI Pigment Red 177 "PR254"; CI Pigment Red 254 "PY150"; CI Pigment Yellow 150 "PY138"; CI Pigment Yellow 138 "PY231"; CI Pigment Yellow 231 "PG36"; CI Pigment Green 36 "PG62"; CI Pigment Green 62 "PG62"; CI Pigment Green 63 "PG58"; CI Pigment Green 58 "PG59"; CI Pigment Green 59 <Dispersant> "SP32000": Basic pigment dispersion resin "Solsperse 32000" (manufactured by Lubrizol Japan) · "PX4701": Basic pigment dispersion resin "EFKA PX4701" (manufactured by BASF) · "BYK111": Acidic pigment dispersion resin "BYK111" (manufactured by BYK) Pigment Derivatives <Polymerizable compound (C)> DPGDA: Dipropylene glycol diacrylate, manufactured by BASF mer DPGDA」 PEA: Phenoxyethyl acrylate, Sartomer "SR339"

[0149] [Example 1] (Curable composition (D-1)) The mixture of the polymerizable compound, photopolymerization initiator, and stabilizer was slowly added to the pigment dispersion previously prepared so as to obtain the composition shown in Table 2, and the resulting mixture was stirred. Next, a surface tension adjuster was added to the mixture, and the mixture was shaken for 6 hours with a shaker to prepare a curable composition (D-1). The obtained curable composition (D-1) was mixed with 0.5 mm thick cellulose ether with a pore diameter of 0.5 mm. The mixture was filtered through a 1.0 micron PTFE filter to remove dust and coarse particles, and used as an evaluation ink. Note that the order of adding and mixing the raw materials to obtain the above mixture may be random.

[0150] [Examples 2 to 44, Comparative Examples 1 to 4] (Curable composition (D-2)~(D-48)) Curable compositions (D-2) to (D-48) were prepared in the same manner as curable composition (D-1), except that the material types and masses were changed as shown in Table 2.

[0151] <Polymerizable compound (C)> VEEA: 2-(2-vinyloxyethoxy)ethyl acrylate, "VEEA" manufactured by Nippon Shokubai Co., Ltd. PEA: Phenoxyethyl acrylate, Sartomer "SR339" DPGDA: Dipropylene glycol diacrylate, manufactured by BASF mer DPGDA」 <Stabilizer> ·BHT: “H-BHT” manufactured by Honshu Kagaku Co., Ltd. Phenothiazine: Seiko Chemical's "Phenothiazine" <Surface conditioner> BYK-UV3510: BYK Chemie, polyether modified polydimethylsiloxane Roxanne <Polymerization initiator (D)> Omnirad819: IGM Resins, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide OmniradTPO: IGM Resins, 2,4,6-trimethylbenzo Il-diphenyl-phosphine oxide Omnirad369: 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1 ·KAYACURE BMS: 4-benzoyl-4'-methyl-diphenyl sulfide manufactured by Nippon Kayaku Co., Ltd. Irgacure OXE-04: Manufactured by BASF Japan, D-1: The following compound [ka] D-2: The following compound [ka] <solvent> DEDG: Diethylene glycol diethyl ether Butycel acetate: Ethylene glycol monobutyl ether acetate

[0152] <Ink evaluation method> The evaluation inks prepared in each of the Examples and Comparative Examples were printed using a single-pass inkjet printer (OnePass Jet manufactured by Tritec Corp.) having an inkjet ejection mechanism equipped with a Kyocera head (KJ4A), a mechanism for transporting the substrate on which the ink has landed at a desired speed, and a mechanism for irradiating the substrate with a UV lamp, under printing conditions of an ink droplet volume of 14 pL and 600 x 600 dpi, and various characteristics were evaluated. The UV lamp used was a GEW UV lamp (240 W) with an integrated light output of 200 mJ / cm 2 The cured film samples were created under the following conditions. The printing speed and printed images were changed for each performance evaluation.

[0153] [Storage stability] The viscosity of the obtained curable composition was measured and recorded as the initial viscosity. An aging test was carried out to measure the accelerated aging viscosity. The accelerated aging viscosity / initial viscosity was calculated as the rate of change due to accelerated aging, and the viscosity was evaluated according to the following criteria. ◎: Change rate less than 5% ○: Change rate is 5% or more and less than 10% △: Change rate is 10% or more but less than 20% ×: Change rate 20% or more

[0154] [50% diameter change rate] For each of the curable compositions prepared above, the curable composition was diluted 200 to 1000 times with methyl ethyl ketone, and the 50% diameter D1 based on volume was measured using a Microtrack UPA150 (Nikkiso Co., Ltd., wet particle size distribution meter). Next, 100 ml of each curable composition was placed in a sample bottle to prevent evaporation and sealed, and stored in a thermostatic chamber at 60 ° C. for one week, and then the 50% diameter D2 based on volume after storage was measured in the same manner as above, and the rate of change in the average particle size was calculated according to the following formula, and the storage stability was evaluated according to the following evaluation criteria. 50% diameter change rate based on volume = {(D2-D1) / D1}×100% ◎: The rate of change in the average particle size of the curable composition is less than 5%. ○: The rate of change in the average particle size of the curable composition is 5% or more and less than 10%. △: The rate of change in the average particle size of the curable composition is 10% or more and less than 30%. ×: The rate of change in the average particle size of the curable composition is 30% or more.

[0155] [Discharge stability] The prepared curable composition was printed with a nozzle check pattern by an inkjet printer, and after printing 100,000 times, the nozzle check pattern was printed again and the dischargeability was evaluated by the number of nozzles that were missing. The evaluation criteria were as follows. The conveyor speed was 35 m / min. ○: No missing nozzles after 100,000 prints △: 1 to 5 nozzles missing after 100,000 prints × : 6 or more nozzles missing after 100,000 prints

[0156] [Evaluation of agglomerated foreign matter] The ink to be evaluated was printed on a 1.1 mm thick glass substrate using an inkjet printer to obtain a cured film sample. The conveyor speed was 35 m / min. The surface of the obtained sample was then observed. An Olympus Systems BX60 metallurgical microscope was used for the evaluation. The magnification was 500x, and the number of particles observable in any five visual fields in transmission was counted and evaluated. ◎ indicates a very good level, ○ indicates a good level, △ indicates a practical level, and × indicates a level not suitable for practical use. ◎: The number of foreign objects is less than 10 ○: The number of foreign objects is 10 or more but less than 20 △: The number of foreign objects is 20 or more and less than 60. ×: 60 or more foreign objects

[0157] [Table 2-1]

[0158] [Table 2-2]

[0159] [Table 2-3]

[0160] The results of Tables 2-1 to 2-3 show that Examples 1 to 44, which contain colorant (A), pigment derivative (B1), and pigment derivative (B2), have a small rate of change in particle size over time, high storage stability, excellent ejection properties, and a low rate of foreign matter generation.

[0161] [Example 101] (Curable composition (DD-1)) A mixture of a polymerizable compound, a photopolymerization initiator, and a polymerization inhibitor was slowly added to the pigment dispersion previously prepared so as to obtain the composition shown in Table 3, and the resulting mixture was stirred. Next, a surface tension adjuster was added to the mixture, and the mixture was shaken for 6 hours with a shaker to prepare a curable composition (DD-1). The obtained curable composition (DD-1) was diluted with 0.0% cellulose acetate and 1.0% cellulose acetate. The ink was filtered through a 0.5 micron PTFE filter to remove dust and coarse particles, and then the ink was The raw materials may be added and mixed in any order to obtain the above mixture.

[0162] [Examples 102 to 105, Comparative Example 101] (Curable composition (DD-2)~(DD-6)) Curable compositions (DD-2) to (DD-6) were prepared in the same manner as curable composition (DD-1), except that the material types and masses were changed as shown in Table 3.

[0163] <Evaluation of Coloring Composition> The obtained curable compositions (DD-1) to (DD-6) were evaluated in the same manner as the curable compositions (D-1) to (D-48). The test results are shown in Table 3.

[0164] [Table 3]

[0165] As can be seen from the results in Table 3, Examples 101 to 105 containing colorant (A), pigment derivative (B1), and pigment derivative (B2) had a small rate of change in particle size over time, high storage stability, excellent ejection properties, and a low rate of foreign matter generation.

Claims

1. A curable composition comprising a colorant (A), a pigment derivative (B1) represented by general formula (1), a pigment derivative (B2) represented by general formula (2), a polymerizable compound (C), and a polymerization initiator (D), wherein the content of a solvent in the curable composition is 5.0 mass% or less. General formula (1) 【Chemistry 1】 [In general formula (1), R １０１ ~R １１３ each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, SO ３ H, or -SO ３ R represents a metal salt or an alkyl ammonium salt of H. １０１ ~R １０４ and / or R １０５ ~R １０８ Adjacent groups of may be joined together to form an aromatic ring which may have a substituent. １０１ ~R １１３ At least one of them is SO ３ H, or -SO ３ H is a metal salt or an alkylammonium salt. General formula (2) 【Chemistry 2】 [In general formula (2), R １１４ ~R １２６ each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, SO ３ H, or -SO ３ R represents a metal salt or an alkyl ammonium salt of H. １１４ ~R １１７ and / or R １１８ ~R １２１ Adjacent groups of may be joined together to form an aromatic ring which may have a substituent. １１４ ~R １２６ of At least one of them is SO ３ H, or -SO ３ H is a metal salt or an alkylammonium salt.

2. The curable composition according to claim 1 , wherein the polymerizable compound (C) comprises a difunctional (meth)acrylate.

3. The curable composition according to claim 1, wherein the colorant (A) comprises at least one selected from the group consisting of phthalocyanine pigments, isoindoline pigments, azo metal complex pigments, quinophthalone pigments, diketopyrrolopyrrole pigments, and anthraquinone pigments.

4. The curable composition according to claim 1, wherein a mass ratio of the pigment derivative (B1) represented by the general formula (1) to the pigment derivative (B2) represented by the general formula (2) is 99.9:0.1 to 50.0:50.

0.

5. The pigment derivative (B1) is represented by the general formula (1), R １０１ ~R １０８ At least one of the groups represented by the general formula (2) is a halogen atom, and the pigment derivative (B2) is １１４ ~R １２１ The curable composition of claim 1 , wherein one or more of is a halogen atom.

6. The curable composition of claim 1 , wherein the polymerization initiator (D) comprises an oxime ester compound.

7. An inkjet ink comprising the curable composition of claim 1.

8. A cured film formed from the curable composition according to any one of claims 1 to 6 or the inkjet ink according to claim 7.

9. A color filter comprising a substrate and the cured film according to claim 8.

10. A solid-state imaging device comprising the color filter according to claim 9.

11. An image display device comprising the color filter according to claim 9.

Images