Pigment composition for color filter, colored composition, color filter, liquid crystal display device, and solid-state imaging element

Abstract

An object of the present application is to provide a pigment composition for a color filter, a colored composition, a color filter, a liquid crystal display device, and a solid-state imaging element, which have excellent storage stability and allow formation of pixels having good lightness, contrast ratio, heat resistance, solvent resistance, and bleeding. The object can be achieved by a pigment composition for a color filter containing diketopyrrolopyrrole pigments represented by general formula (1) and diketopyrrolopyrrole pigments represented by general formula (2), and the mass ratio of general formula (1) to general formula (2) is 99.9:0.1 to 90.0:10.0.

Description

TECHNICAL FIELD

[0001] The present application relates to a coloring composition for manufacturing a color filter used in a color liquid crystal display device, a solid-state imaging element represented by a complementary metal oxide semiconductor (C-MOS), a charge coupled device (CCD), an organic electroluminescence (EL) display device, and electronic paper, and a color filter including a filter segment formed using the coloring composition. BACKGROUND

[0002] On a color filter used in a color liquid crystal display device, a transparent electrode for driving liquid crystal is generally formed by evaporation or sputtering, and further, an alignment film for aligning liquid crystal in a certain direction is formed on the transparent electrode. In order to sufficiently obtain the properties of these transparent electrode and alignment film, it is necessary to perform the formation steps at a high temperature of usually 230°C or higher, and heat resistance is required for the color filter.

[0003] As important quality items required for a color filter, contrast ratio and brightness can be listed. If a color filter having a low contrast ratio is used, the degree of polarization controlled by liquid crystal is disturbed, light leaks in a state where light must be shielded (OFF state), and light attenuation occurs in a state where light must be transmitted (ON state), and thus a blurred image is caused. Therefore, in order to realize a high-quality liquid crystal display device, it is indispensable to increase the contrast ratio. In addition, if a color filter having a low brightness is used, the transmittance of light is low, and thus a dark image is caused, and in order to set a bright image, the number of backlights as light sources needs to be increased. However, from the viewpoint of suppressing power consumption, high brightness of a color filter is a trend.

[0004] As a colorant for forming a red filter segment, C.I. Pigment Red 254, C.I. Pigment Red 291, C.I. Pigment Red 242, and C.I. Pigment Red 177 are generally widely used. C.I. Pigment Red 254 or C.I. Pigment Red 291, which is a diketopyrrolopyrrole pigment, is a pigment having particularly excellent brightness, but in recent years, the expectation for high contrast of a color filter is also strong, and thus it is necessary to make the primary particle diameter of the diketopyrrolopyrrole pigment as small as possible. However, the diketopyrrolopyrrole pigment which is made fine has a property of easily growing crystals through intermolecular hydrogen bonds, and thus there is a problem that foreign matter is generated by crystallization in a heating step at the time of forming a color filter.

[0005] In Patent Literature 1, it is disclosed that crystallization during a heating step can be inhibited by using C.I. Pigment Red 291 in combination with a diketopyrrolopyrrole pigment having a specific structure, but further improvement in terms of brightness, contrast ratio, heat resistance, solvent resistance, and the like is required.

[0006] Prior Art Documents

[0007] Patent Literature

[0008] Patent Literature 1: Japanese Patent Laid-Open No. 2012-155232 SUMMARY

[0009] Problems to be Solved by the Invention

[0010] An object of the present application is to provide a pigment composition for a color filter, a colored composition, and a color filter formed using the colored composition, which have excellent storage stability and allow formation of pixels having good brightness, contrast ratio, heat resistance, solvent resistance, and bleeding.

[0011] Technical Means for Solving the Problems

[0012] As a result of repeated diligent studies by the present inventors, it has been found that the above problems can be solved by a pigment composition containing two kinds of diketopyrrolopyrrole pigments having different structures at a specific mass ratio, and the present application has been achieved.

[0013] That is, the present application relates to a pigment composition for a color filter, which contains a diketopyrrolopyrrole pigment represented by General Formula (1) and a diketopyrrolopyrrole pigment represented by General Formula (2), and the mass ratio of General Formula (1) to General Formula (2) is 99.9:0.1 to 90.0:10.0.

[0014] General Formula (1)

[0015] [Chemical Formula 1]

[0016]

[0017] [In General Formula (1), X represents a halogen atom]

[0018] General Formula (2)

[0019] [Chemical Formula 2]

[0020]

[0021] [In General Formula (2), Y and Z are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group having a carbon number of 1 to 20 which can have a substituent, or a phenyl group which can have a substituent; at least one of Y and Z is an alkyl group having a carbon number of 3 to 18]

[0022] Further, the present application relates to the color filter pigment composition, which further contains a pigment derivative.

[0023] Further, the present application relates to a color filter coloring composition, which contains a colorant, a resin, and a solvent, and the colorant contains the color filter pigment composition.

[0024] Further, the present application relates to the color filter coloring composition, which further contains a photopolymerizable monomer and / or a photopolymerization initiator.

[0025] Further, the present application relates to a color filter, which includes a filter segment formed from the color filter coloring composition.

[0026] Further, the present application relates to a liquid crystal display device, which includes the color filter.

[0027] Further, the present application relates to a solid-state imaging element, which includes the color filter.

[0028] Effects of the Invention

[0029] According to the present application, it is possible to provide a color filter pigment composition for a color filter, a coloring composition, and a color filter formed using the coloring composition, which have excellent storage stability and allow formation of a pixel having excellent lightness, contrast ratio, heat resistance, solvent resistance, and bleeding. DETAILED DESCRIPTION

[0030] Hereinafter, each component of the color filter pigment composition for a color filter and the color filter coloring composition according to the present application will be described in detail. Further, "C.I." in the present application means Colour Index (C.I.). Further, in the case of expressions of "(meth)acryl", "(meth)acrylic acid", "(meth)acrylate", and "(meth)acryloxy", unless otherwise specified, they respectively mean "acryl and / or methacryl", "acrylic acid and / or methacrylic acid", "acrylate and / or methacrylate", and "acryloxy and / or methacryloxy".

[0031] <color filter pigment composition>

[0032] The color filter pigment composition according to the present application has excellent effects of lightness, contrast ratio, heat resistance, solvent resistance, and bleeding by containing diketopyrrolopyrrole pigments of general formula (1) and general formula (2) in a range of 99.9:0.1 to 90.0:10.0 by mass ratio.

[0033] (Diketopyrrolopyrrole pigment (A1) of general formula (1))

[0034] The diketopyrrolopyrrole pigment (A1) represented by general formula (1) as an essential component of the pigment composition of the present application is described.

[0035] General formula (1)

[0036] [Chemical formula 3]

[0037]

[0038] [In general formula (1), X represents a halogen atom]

[0039] Among X, as the "halogen atom", fluorine, bromine, chlorine, iodine can be exemplified, and from the viewpoint of brightness and contrast ratio, chlorine and bromine are preferable. As specific examples of the diketopyrrolopyrrole pigment of general formula (1) that can be used in the present application, C.I. Pigment Red 254, 291 can be exemplified, but are not limited thereto. From the viewpoint of brightness, C.I. Pigment Red 291 is preferable.

[0040] (Diketopyrrolopyrrole pigment (A2) of general formula (2))

[0041] The diketopyrrolopyrrole pigment (A2) represented by general formula (2) as an essential component of the pigment composition of the present application is described.

[0042] General formula (2)

[0043] [Chemical formula 4]

[0044]

[0045] [In general formula (2), Y and Z are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group having a substituent having a carbon number of 1 to 20, a phenyl group having a substituent; wherein at least one of Y and Z is an alkyl group having a carbon number of 3 to 18]

[0046] Among Y and Z, as the "halogen atom", fluorine, bromine, chlorine, iodine can be exemplified.

[0047] Among Y and Z, as the "alkyl group having a substituent having a carbon number of 1 to 20", there are un-substituted or oxidized alkylene group having an ether bond and the like, and can be linear or branched, and specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, octadecyl group, eicosyl group, 1,5-dimethylhexyl group, 1,6-dimethylheptyl group, 2-ethylhexyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, polyoxyethylene group and the like can be exemplified, but are not limited thereto.

[0048] As the "phenyl group which can have a substituent" in Y and Z, a phenyl group having an alkyl group having a carbon number of 1 to 4, a trifluoromethyl group, a halogen atom, a nitro group, a cyano group, a carbamoyl group, a sulfamoyl group, an alkoxy group having a carbon number of 1 to 4, or the like can be exemplified. More specifically, a phenyl group, a p-methylphenyl group, a 4-tert-butylphenyl group, a p-nitrophenyl group, a p-methoxyphenyl group, a p-chlorophenyl group, a 2,4-dichlorophenyl group, a 3-carbamoylphenyl group, and the like can be exemplified, but are not limited thereto.

[0049] At least one of Y and Z is "an alkyl group having a carbon number of 3 to 18". As the "alkyl group having a carbon number of 3 to 18", a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a dodecyl group, an octadecyl group, a 1,5-dimethylhexyl group, a 1,6-dimethylheptyl group, a 2-ethylhexyl group, a cyclohexyl group, an isobornyl group, and the like can be exemplified, but are not limited thereto. From the viewpoint of heat resistance (crystallization during a processing step), contrast ratio, and solvent resistance, the carbon number of the alkyl group is preferably a carbon number of 4 to 12, and more preferably a carbon number of 4 to 8. If the length of the alkyl group is long, the aggregation caused by heat of the diketopyrrolopyrrole pigment of general formula (1) can be suppressed by a steric effect, and the contrast ratio or the heat resistance becomes good. On the other hand, if the alkyl group is too long, the dispersion stability becomes poor, and the solubility in a solvent is improved, and thus there is a tendency that the solvent resistance or the migration is deteriorated.

[0050] Specific examples of the diketopyrrolopyrrole pigment of general formula (2) which can be used in the present application are exemplified below, but are not limited thereto.

[0051] [Chemical Formula 5]

[0052]

[0053] In the present application, the content of the diketopyrrolopyrrole pigment represented by general formula (2) is in the range of 0.1 mass% to 10 mass% based on the total mass of the diketopyrrolopyrrole pigments of general formula (1) and general formula (2). It is preferable that the content be in the range of 0.1 mass% to 5.0 mass%, and more preferably in the range of 0.1 mass% to 3.0 mass%.

[0054] If the ratio of the diketopyrrolopyrrole pigment of general formula (2) exceeds 10 mass%, the effect of improving heat resistance (crystallization inhibition) is obtained, but the excellent brightness of the diketopyrrolopyrrole pigment of general formula (1) is impaired, and the storage stability or solvent resistance also becomes poor. On the other hand, if the ratio of the diketopyrrolopyrrole pigment represented by general formula (2) is not 0.1 mass%, the high contrast ratio and heat resistance (crystallization inhibition) are not sufficient. In the case where the crystallization inhibition effect is not sufficient, light scattering due to crystalline foreign matter precipitated to the surface of the coating film in the heating step is caused, and thus the brightness and the contrast ratio are reduced. Therefore, by using the coloring composition containing the diketopyrrolopyrrole pigment of general formula (2) at the ratio, high brightness and high contrast ratio can be achieved, and the crystallization of the diketopyrrolopyrrole pigment of general formula (1) can be inhibited even with the heating step.

[0055] (Method for producing diketopyrrolopyrrole pigment)

[0056] The diketopyrrolopyrrole pigment represented by general formula (1) or general formula (2) can be produced by a succinic acid diester synthesis method. That is, 1 mole of succinic acid diester is subjected to condensation reaction with 2 moles of any one of the benzonitrile compounds of general formula (50) or general formula (60) in an inert organic solvent such as tert-pentanol in the presence of an alkali metal or an alkali metal alcoholate at a high temperature of 80°C to 110°C, to produce an alkali metal salt of a diketopyrrolopyrrole compound, and then, the alkali metal salt of the diketopyrrolopyrrole compound is subjected to protonation using water, an alcohol, an acid, or the like, whereby the diketopyrrolopyrrole pigment of general formula (1) or general formula (2) is obtained. At this time, the size of the primary particle diameter obtained can be controlled by the temperature in the protonation, the kind, ratio, or amount of water, an alcohol, or an acid. The method for producing the diketopyrrolopyrrole pigment represented by general formula (1) or general formula (2) is not limited to the method.

[0057] General formula (50)

[0058] [Chemical formula 6]

[0059]

[0060] [In general formula (50), X represents a halogen atom]

[0061] General formula (60)

[0062] [Chemical formula 7]

[0063]

[0064] [In General Formula (60), Y and Z are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group which can have a substituent, or a phenyl group which can have a substituent; at least one of Y and Z is an alkyl group which can have a substituent and has 3 to 18 carbon atoms]

[0065] (other colorants)

[0066] The pigment composition and the coloring composition of the present application can contain various pigments and dyes in addition to the diketopyrrolopyrrole pigments represented by General Formula (1) and General Formula (2) as essential components, and can contain them as colorants. Representative pigments and dyes which can be used in the present application are listed below.

[0067] Red pigments which can be used in the present application include, for example, C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48: 1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 57:1, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 221, 224, 226, 242, 246, 255, 264, 270, 272, 273, 274, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 295, 296, and the like, but are not particularly limited thereto. In addition, xanthene-based, cyanine-based, azo-based, anthraquinone-based, and the like red dyes can also be used. Specifically, for example, C.I. Acid Red 52, 87, 92, 289, 338, and the like xanthene-based acid dyes, and the like can be used.

[0068] Orange pigments which can be used in the present application include, for example, C.I. Pigment Orange 38, 43, or 71, but are not particularly limited thereto.

[0069] The yellow pigment usable in the present application can be exemplified by C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 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, 128, 129, 137, 138, 139, 147, 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, quinophthalone pigments described in Japanese Patent No. 4993026, or the like, but is not particularly limited thereto. In addition, quinoline-based, azo-based, methine-based, coumarin-based, isoindoline-based, or the like yellow dye can also be used.

[0070] The green pigment usable in the present application can be exemplified by C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, zinc phthalocyanine pigments described in Japanese Patent Application Publication No. 2008-19383, Japanese Patent Application Publication No. 2007-320986, Japanese Patent Application Publication No. 2004-70342, International Publication No. 2015 / 118720, aluminum phthalocyanine pigments described in Japanese Patent No. 4893859, or the like, but is not particularly limited thereto. In addition, triarylmethane-based, phthalocyanine-based, squarylium-based, or the like green dye can also be used.

[0071] The blue pigment usable in the present application can be exemplified by C.I. Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 60, 64, aluminum phthalocyanine pigments described in Japanese Patent Application Publication No. 2004-333817, Japanese Patent No. 4893859, or the like, but is not particularly limited thereto.

[0072] The violet pigment usable in the present application can be exemplified by C.I. Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50, etc., but is not particularly limited to these.

[0073] In the pigment composition of the present application, titanium oxide, iron oxide, antimony pentoxide, zinc oxide, silicon dioxide and the like metal oxides, cadmium sulfide, calcium carbonate, barium carbonate, barium sulfate, clay, talc, yellow lead, carbon black and the like inorganic pigments can also be used.

[0074] In the case of using the pigment composition of the present application in combination with other colorants, red pigments or yellow pigments are mostly used in combination in terms of the relationship with color characteristics. Specifically, as the red pigments used in combination, C.I. Pigment Red 177, C.I. Pigment Red 242, C.I. Pigment Red 269, C.I. Pigment Red 296 are preferable in terms of color characteristics. As the yellow pigments, C.I. Pigment Yellow 138 or quinophthalone pigments described in Japanese Patent No. 4993026, C.I. Pigment Yellow 139, C.I. Pigment Yellow 185, C.I. Pigment Yellow 150 are preferable in terms of color characteristics.

[0075] <Colorant Derivative>

[0076] In the pigment composition or the coloring composition of the present application, a colorant derivative can be contained for the purpose of inhibiting the growth of pigment crystals and improving the dispersibility of pigments. As the colorant derivative usable in the present application, existing colorant derivatives having an acidic group, a basic group, a neutral group or the like in an organic colorant residue can be used. For example, compounds having an acidic functional group such as a sulfonic group, a carboxyl group, a phosphoric acid group and amine salts of these, or compounds having a basic functional group such as a sulfonamide group or a tertiary amino group at the terminal, or compounds having a neutral functional group such as a phenyl group or a phthalimide alkyl group can be exemplified. As the organic colorant, for example, diketopyrrolopyrrole pigments; copper phthalocyanine, zinc phthalocyanine, aluminum phthalocyanine, halogenated copper phthalocyanine, halogenated zinc phthalocyanine, halogenated aluminum phthalocyanine, metal-free phthalocyanine and the like phthalocyanine pigments; aminoanthraquinone, diaminoanthraquinone, anthrapyrimidine, flavanthrone, anthanthrone, indanthrone, pyranthrone, violanthrone and the like anthraquinone pigments; quinacridone pigments; dioxazine pigments; perinone pigments; perylene pigments; thiazine indigo pigments; triazine pigments; benzimidazolone pigments; indole pigments such as benzisoindole; isoindoline pigments; isoindolinone pigments; quinophthalone pigments; naphthol pigments; threne pigments; metal complex pigments; azo, disazo, polyazo and the like azo pigments and the like can be exemplified.

[0077] More specifically, the existing pigment derivatives described in Japanese Patent Laid-Open No. 61-246261, Japanese Patent Laid-Open No. 63-264674, Japanese Patent Laid-Open No. 09-272812, Japanese Patent Laid-Open No. 10-245501, Japanese Patent Laid-Open No. 10-265697, Japanese Patent Laid-Open No. 11-199796, Japanese Patent Laid-Open No. 2001-172520, Japanese Patent Laid-Open No. 2001-220520, Japanese Patent Laid-Open No. 2002-201377, Japanese Patent Laid-Open No. 2003-165922, Japanese Patent Laid-Open No. 2003-168208, Japanese Patent Laid-Open No. 2003-171594, Japanese Patent Laid-Open No. 2004-217842, Japanese Patent Laid-Open No. 2005-213404, Japanese Patent Laid-Open No. 2006-291194, Japanese Patent Laid-Open No. 2007-079094, Japanese Patent Laid-Open No. 2007-226161, Japanese Patent Laid-Open No. 2007-314681, Japanese Patent Laid-Open No. 2007-314785, Japanese Patent Laid-Open No. 2008-31281, Japanese Patent Laid-Open No. 2009-57478, WO 2009 / 025325, WO 2009 / 081930, Japanese Patent Laid-Open No. 2011-162662, WO 2011 / 052617, Japanese Patent Laid-Open No. 2012-172092, Japanese Patent Laid-Open No. 2012-208329, Japanese Patent Laid-Open No. 2012-226110, WO 2012 / 102399, Japanese Patent Laid-Open No. 2014-5439, WO 2016 / 163351, Japanese Patent Laid-Open No. 2017-156397, Japanese Patent No. 5753266, and the like can be cited, and these can be used alone or in combination of two or more. Further, in these documents, there are cases where the pigment derivative is described as a derivative, a pigment derivative, a pigment dispersant, or only as a compound, and the like, but the compound having a functional group such as an acidic group, a basic group, a neutral group, and the like in an organic pigment residue is the same meaning as the pigment derivative.

[0078] In the case where the pigment derivative is used in the present application, the pigment derivative having a basic substituent is preferable in terms of the effect of inhibiting the aggregation of pigments with each other. Further, as the organic pigment residue, the pigment derived from diketopyrrolopyrrole-based pigments, anthraquinone-based pigments, thiazine indigo-based pigments, quinophthalone-based pigments, or azo-based pigments is preferable in terms of the color tone or the contrast ratio.

[0079] <Refinement of Pigments>

[0080] In the case where the colorant used in the colored composition of the present application is a pigment, it is preferable to be used after being micronized. The method of micronization is not particularly limited, and for example, any one of wet milling, dry milling, and dissolution precipitation method can be used, and the pigment can be micronized by, for example, a kneader method which is one of wet milling, salt milling treatment, and the like, as exemplified in the present application. The average primary particle diameter of the pigment, which is obtained by transmission electron microscope (TEM), is preferably in the range of 5 nm to 90 nm. If less than 5 nm, it is difficult to disperse in an organic solvent, and if more than 90 nm, a sufficient contrast ratio cannot be obtained. For this reason, the more preferable average primary particle diameter is in the range of 10 nm to 70 nm.

[0081] The salt milling treatment is a treatment 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 type kneader such as a kneader, a two-rod roll mill, a three-rod roll mill, a ball mill, a grinder, a sand mill, a planetary mixer, and the like, and then the water-soluble inorganic salt and the water-soluble organic solvent are removed by water washing. The water-soluble inorganic salt functions as a crushing aid, and the pigment is crushed by the high hardness of the inorganic salt during the salt milling. By optimizing the conditions during the salt milling treatment of the pigment, a pigment having a very fine primary particle diameter, a narrow distribution range, and a sharp particle size distribution can be obtained.

[0082] As the water-soluble inorganic salt, sodium chloride, barium chloride, potassium chloride, sodium sulfate, and the like can be used, and from the price aspect, it is preferable to use sodium chloride (table salt). From the aspects of treatment efficiency and production efficiency, the water-soluble inorganic salt is preferably used in an amount of 50 parts by mass to 2000 parts by mass, and most preferably in an amount of 300 parts by mass to 1000 parts by mass, with respect to 100 parts by mass of the pigment.

[0083] The water-soluble organic solvent functions to wet the pigment and the water-soluble inorganic salt. If it is an organic solvent that dissolves (mixes) in water and does not substantially dissolve the inorganic salt used, there is no particular limitation. Among them, since the temperature rises during salt milling, it becomes a state in which the solvent easily evaporates, and therefore from the aspect of safety, a high-boiling solvent having a boiling point of 120°C or higher is preferred. 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 glycol, and the like can be used. The water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by mass, and most preferably 50 to 500 parts by mass, with respect to 100 parts by mass of the pigment.

[0084] In the salt milling treatment, a pigment derivative can also be used in order to improve the kneading efficiency. It is very effective for the fine particle and the particle size adjustment of the pigment. In the fine particle of the diketopyrrolopyrrole-based pigment composition used in the present application, the pigment derivative is preferably used, but is not limited to these. The amount of the pigment derivative used is preferably in the range of 0.5 to 30% by mass with respect to 100% by mass of the pigment, in a range that does not affect the color tone.

[0085] In addition, in the salt milling treatment, a resin can also be added as necessary. The kind of the resin used is not particularly limited, and a natural resin, a modified natural resin, a synthetic resin, a synthetic resin modified with a natural resin, and the like can be used. The resin used is preferably solid at room temperature and water-insoluble, and further preferably soluble in part in the organic solvent. The amount of the resin used is preferably in the range of 5 to 200 parts by mass with respect to 100 parts by mass of the pigment.

[0086] <Colored filter coloring composition>

[0087] The colored filter coloring composition of the present application contains at least a coloring agent containing the colored filter pigment composition of the present application, a resin, and a solvent. In addition, a resin-type dispersant or a photopolymerizable monomer, a photopolymerization initiator, or the like to impart photosensitivity can be used as necessary.

[0088] <Resin-type dispersant>

[0089] The coloring composition of the present application can be used in combination with a resin-type dispersant. The dispersant includes a coloring agent-affinity site having a property of adsorbing an added coloring agent or pigment derivative, and a site having compatibility with a coloring agent carrier, and functions to adsorb the added coloring agent to stabilize dispersion in the coloring agent carrier. As the resin-type dispersant, specifically, a polycarbamic acid ester, a polyacrylic acid ester, or the like; an unsaturated polyamide, a polycarboxylic acid, a (partial) amine salt of a polycarboxylic acid, an ammonium salt of a polycarboxylic acid, an alkylamine salt of a polycarboxylic acid, a polysiloxane, a long-chain polyaminoamide phosphate, a polycarboxylic acid ester containing a hydroxyl group, or a modified product of these; an oily dispersant such as an amide or a salt thereof formed by the reaction of a poly(lower alkylene imine) with a polyester having a free carboxyl group; a water-soluble resin such as a (meth)acrylic acid-styrene copolymer, a (meth)acrylic acid-(meth)acrylic acid ester copolymer, a styrene-maleic acid copolymer, a polyvinyl alcohol, a polyvinylpyrrolidone, or a water-soluble high-molecular compound; a polyester-based, a modified polyacrylate-based, an ethylene oxide / propylene oxide addition compound, a phosphate-based, or the like can be used alone or in combination with two or more, but is not necessarily limited to these.

[0090] Among the resin-type dispersants, a graft copolymer containing a nitrogen atom; or an acrylic block copolymer containing a nitrogen atom having a functional group such as a tertiary amino group, a quaternary ammonium base, a nitrogen-containing heterocycle, or the like in a side chain, and a urethane-based high-molecular dispersant are known to lower the viscosity of a dispersion at a small amount of addition and to exhibit a high contrast ratio.

[0091] In the case of using the resin-type dispersant in the present application, a resin-type dispersant having an acidic substituent is preferred, and a resin-type dispersant having an aromatic carboxyl group or a phosphoric acid group is particularly preferred because of its particularly large effect of preventing re-agglomeration of the coloring agent after dispersion. As the resin-type dispersant having an aromatic carboxyl group, resin-type dispersants described in WO 2008 / 007776, Japanese Patent Application Publication No. 2008-029901, Japanese Patent Application Publication No. 2009-155406, Japanese Patent Application Publication No. 2009-155406, Japanese Patent Application Publication No. 2010-185934, and Japanese Patent Application Publication No. 2011-157416 can be mentioned, but are not limited to these.

[0092] The resin-type dispersant is preferably used in an amount of 5 to 200 parts by mass, and more preferably 5 to 100 parts by mass, relative to 100 parts by mass of the total amount of the coloring agent, from the viewpoint of film formability.

[0093] <Resin>

[0094] As the resin which is an essential component of the colored composition of the present application, a thermoplastic resin or the like can be exemplified which disperses, dyes, or penetrates the colorant. In the case of using in the form of an alkali developing type colored resist material, an alkali soluble vinyl resin which is copolymerized with an ethylenically unsaturated monomer containing an acidic group is preferably used. In addition, in order to further improve the photosensitivity, a living energy ray hardenable resin having an ethylenically unsaturated double bond can also be used.

[0095] In particular, by using a living energy ray hardenable resin having an ethylenically unsaturated double bond in the side chain in an alkali developing type colored resist material, when a coating film is formed by exposure with a living energy ray, the resin is three-dimensionally crosslinked, whereby the colorant is fixed, the heat resistance becomes good, and the discoloration (deterioration of the spectral characteristics) of the colorant due to heat can be suppressed. In addition, the following effect is also obtained: in the developing step, the aggregation and precipitation of the colorant component is also suppressed.

[0096] As the resin, a resin having a transmittance of preferably 80% or more, more preferably 95% or more in all wavelength regions of the visible light region of 400 nm to 700 nm is preferable.

[0097] In order to preferably disperse the colorant, the weight average molecular weight (Mw) of the resin is preferably in the range of 2,000 to 80,000, more preferably in the range of 3,000 to 40,000. In addition, the number average molecular weight (Mn) is preferably in the range of 3,000 to 40,000, and the value of Mw / Mn is preferably 10 or less.

[0098] In the case of using the resin as a photosensitive colored composition for a color filter, the balance between the carboxyl group which functions as a colorant adsorption base and an alkali soluble base at the time of development, and the aliphatic group and the aromatic group which function as an affinity base for the colorant carrier and the solvent is important for the dispersibility, the penetrability, the developability, and the durability of the colorant, and a resin having an acid value of 20 mgKOH / g to 300 mgKOH / g is preferably used. If the acid value is less than 20 mgKOH / g, there is a case where the solubility to the developing solution is poor and it is difficult to form a fine pattern. If it exceeds 300 mgKOH / g, there is a case where a fine pattern is not left.

[0099] Regarding the resin, in terms of the film formability and each of the good resistances, it is preferable to use in an amount of 20 parts by mass or more with respect to 100 parts by mass of the total mass of the colorant, and in terms of the high colorant concentration and the good color characteristics which can be exhibited, it is preferable to use in an amount of 1,000 parts by mass or less.

[0100] As the thermoplastic resin used in the resin, for example, acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, chloroethylene-vinyl acetate copolymer, polyvinyl acetate, polyurethane-based resin, polyester resin, ethylene-based resin, alkyd resin, polystyrene resin, polyamide resin, rubber-based resin, cyclized rubber-based resin, cellulose, polyethylene (High Density Polyethylene (HDPE), Low Density Polyethylene (LDPE)), polybutadiene, and polyimide resin, etc. can be exemplified. Among them, use of acrylic resin is preferred.

[0101] As the ethylene-based alkali-soluble resin obtained by copolymerizing an ethylenically unsaturated monomer containing an acidic group, for example, a resin having a carboxyl group, a sulfonic group, or the like can be exemplified.

[0102] As the alkali-soluble resin, specifically, acrylic resin having an acidic group, α-olefin / maleic acid (anhydride) copolymer, styrene / styrene sulfonic acid copolymer, ethylene / (meth)acrylic acid copolymer, or isobutylene / maleic acid (anhydride) copolymer, etc. can be exemplified. Among them, at least one resin selected from the group consisting of acrylic resin having an acidic group and styrene / styrene sulfonic acid copolymer, and particularly, acrylic resin having an acidic group is high in heat resistance and transparency, and thus can be suitably used.

[0103] As the active energy ray-curable resin having an ethylenically unsaturated double bond, for example, a resin into which an unsaturated ethylenic double bond is introduced by a method of (i) or (ii) shown below can be exemplified.

[0104] [Method (i)]

[0105] As the method (i), for example, a method in which, to a side chain epoxy group of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having an epoxy group with other one or more monomers, a carboxyl group of an unsaturated monobasic acid having an unsaturated ethylenic double bond is added, and further, the generated hydroxyl group is reacted with a polybasic anhydride, thereby introducing an unsaturated ethylenic double bond and a carboxyl group, can be exemplified.

[0106] As the unsaturated ethylenic monomer having an epoxy group, for example, glycidyl (meth)acrylate, methyl glycidyl (meth)acrylate, 2-glycidyloxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate can be exemplified, and these can be used alone or in combination of two or more. From the viewpoint of reactivity with the unsaturated monobasic acid of the next step, glycidyl (meth)acrylate is preferred.

[0107] As the unsaturated monobasic acid, there can be mentioned (meth)acrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, p-vinylbenzoic acid, α-haloalkyl, alkoxy, halogen, nitro, cyano-substituted (meth)acrylic acid, and the like, which can be used alone or in combination of two or more.

[0108] As the polybasic anhydride, there can be mentioned tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride, and the like, which can be used alone or in combination of two or more. In order to increase the number of carboxyl groups, etc., trimellitic anhydride, or pyromellitic dianhydride can be used as necessary, or the residual anhydride group can be hydrolyzed. In addition, as the polybasic anhydride, tetrahydrophthalic anhydride or maleic anhydride having an unsaturated ethylenic double bond can be used to further increase the unsaturated ethylenic double bond.

[0109] As the similar method to the method (i), there can be mentioned a method in which a part of the side chain carboxyl group of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having a carboxyl group with other one or more monomers is reacted with an unsaturated ethylenic monomer having an epoxy group, thereby introducing an unsaturated ethylenic double bond and a carboxyl group.

[0110] [Method (ii)]

[0111] As the method (ii), there can be mentioned a method in which the isocyanate group of an unsaturated ethylenic monomer having an isocyanate group is reacted with the side chain hydroxyl group of a copolymer obtained by using an unsaturated ethylenic monomer having a hydroxyl group and copolymerizing with other unsaturated monobasic acid monomer having a carboxyl group, or other monomer.

[0112] As the unsaturated ethylenic monomer having a hydroxyl group, there can be mentioned 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate or 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate or 3-hydroxybutyl (meth)acrylate or 4-hydroxybutyl (meth)acrylate, glycerol (meth)acrylate or cyclohexane dimethanol mono(meth)acrylate, and the like, which can be used alone or in combination of two or more. In addition, polyether mono(meth)acrylate obtained by addition polymerization of ethylene oxide, propylene oxide and / or butylene oxide, etc. to the above (meth)acrylic acid hydroxyalkyl ester, or (poly)ester mono(meth)acrylate obtained by addition of (poly)γ-valerolactone, (poly)ε-caprolactone and / or (poly)12-hydroxystearic acid, etc. can also be used. From the viewpoint of suppressing foreign matter in the coating film, 2-hydroxyethyl (meth)acrylate or glycerol (meth)acrylate is preferred.

[0113] As the unsaturated ethylenic monomer having an isocyanate group, 2- (meth) acryloyloxyethyl isocyanate or 1, 1-bis ( (meth) acryloyloxy) ethyl isocyanate, etc. can be exemplified, but are not limited thereto, and two or more kinds thereof can be used in combination.

[0114] <thermosetting compound>

[0115] The colored composition of the present application can contain a thermosetting compound. As the thermosetting compound, for example, an epoxy compound and / or resin, a benzoguanamine compound and / or resin, a rosin-modified maleic compound and / or resin, a rosin-modified fumaric compound and / or resin, a melamine compound and / or resin, a urea compound and / or resin, a phenol compound and / or resin can be exemplified, but the present application is not limited thereto.

[0116] In the case where a thermosetting compound is used in the present application, from the viewpoint of heat resistance, solvent resistance, etc., an epoxy compound is preferred. As the epoxy compound, there is no particular limitation as long as it has an epoxy group, and it can be a low molecular compound or a high molecular weight compound such as a resin, and a multifunctional epoxy compound is particularly preferred in order to obtain a coating film having a high crosslinking density.

[0117] As the preferred weight average molecular weight of the epoxy compound, it is preferably 200 or more and 100,000 or less. A more preferred molecular weight is 300 or more and 10,000 or less, and further preferably 500 or more and 5000 or less.

[0118] As the epoxy compound, a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a cresol novolak type epoxy compound, a biphenyl type epoxy compound, an alicyclic epoxy compound, etc. can be used. A novolak type epoxy compound and an alicyclic epoxy compound are preferred, and an alicyclic epoxy compound is particularly preferred. The number of functional groups is preferably two or more, and from the aspect that the thermal crosslinking property is excellent, three or more is more preferred.

[0119] As the difunctional epoxy compound, DIC manufactured EPICLON 830, 840, 850, 860, 1050, 2050, 3050, 4050, 7050, HM-091, 101; Nagase Chemtex manufactured Denacol EX-211, 212, 252, 711, 721, etc. can be exemplified.

[0120] As the multifunctional epoxy compound of three or more functions, there are mentioned novolac type epoxy compounds, EHPE 3150 (manufactured by Daicel Chemical Industries, Ltd.) and the like as a high molecular cycloaliphatic backbone epoxy compound. As the novolac type epoxy compound, there are specifically mentioned EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, EOCN-4500, EOCN-4600, XD-1000, XD-1000-L, XD-1000-2L, NC-3000, NC-3000-H (all manufactured by Nippon Kayaku Co., Ltd.), YDPN-638, YDCN-700-2, YDCN-700-3, YDCN-700-5, YDCN-700-7, YDCN-700-10, YDCN-704, YDCN-704A (all manufactured by Nippon Steel Chemical Co., Ltd.), N-660, N-665, N-670, N-673, N-680, N-690, N-695, N-665-EXP, N-672-EXP, N-655-EXP-S, N-662-EXP-S (all manufactured by DIC Corporation), and the like. Further, there are mentioned Techmore VG3101 (manufactured by Printec Corporation) as a trifunctional epoxy compound, TETRAD-C, TETRAD-X (both manufactured by Mitsubishi Gas Chemical Co., Inc.) as a tetrafunctional epoxy compound, and the like. Further, there are mentioned Denacol EX-313, 314, 321, 411, 421, 512, 521, 611, 612, 614, 614B, 622, and the like (manufactured by Nagase Chemtex Corporation). Further, there are mentioned JER1031S, 1302H60, 604, 630, 630LSD, and the like (manufactured by Mitsubishi Chemical).

[0121] <Organic solvent>

[0122] The coloring composition of the present application contains an organic solvent in order to easily perform the operation of making the colorant sufficiently dispersed and impregnated in the colorant carrier and coating on a substrate such as a glass substrate in a manner that the dry film thickness becomes 0.2 μm to 5 μm to form a colored film. The organic solvent is selected in consideration of the solubility of each component of the coloring composition and safety in addition to the good coatability of the coloring composition.

[0123] As the organic solvent, for example, ethyl lactate, benzyl alcohol, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-l,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-l-one, 3,3,5-trimethylcyclohexanone, 3-ethoxypropyl acetate, 3-methyl-l,3-butanediol, 3-methoxy-3-methyl-l-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-diethylbenzene, m-diethylbenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-butanol, n-butylbenzene, n-propyl acetate, o-diethylbenzene, o-diethylbenzene, p-diethylbenzene, sec-butylbenzene, t-butylbenzene, γ-butyrolactone, isobutanol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol mono-t-butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetonol, glycerol triacetate, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isopentyl acetate, isobutyl acetate, propyl acetate, dibasic acid ester, and the like can be exemplified.

[0124] These solvents can be used alone or two or more of them can be used in any ratio as needed.

[0125] Among them, in terms of the dispersibility of the colorant, the penetrability, and the coatability of the colored composition, it is preferable to use ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, or the like ethylene glycol acetate, benzyl alcohol, diacetonol, 3-methoxybutanol, propylene glycol monomethyl ether, or the like alcohol, or cyclohexanone, or the like ketone.

[0126] In addition, as to the organic solvent, in terms of adjusting the colored composition to an appropriate viscosity and forming a colored film of a uniform film thickness as a target, it is preferable to use it in an amount of 500 parts by mass to 4000 parts by mass, relative to 100 parts by mass of the colorant.

[0127] <Photopolymerizable monomer>

[0128] The colored composition of the present application can also contain a photopolymerizable monomer. The photopolymerizable monomer includes a monomer or oligomer that is hardened by ultraviolet rays or heat, etc. and generates a transparent resin.

[0129] As the monomer or oligomer that is hardened by ultraviolet rays or heat, etc. and generates a transparent resin, for example, there can be mentioned methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,6-hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, tricyclodecane (meth)acrylate, ester acrylate, (meth)acrylate of hydroxymethylated melamine, epoxy (meth)acrylate, urethane acrylate, and various acrylates and methacrylates, (meth)acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, N-vinylformamide, acrylonitrile, and the like, but are not necessarily limited to these.

[0130] These photopolymerizable monomers can be used singly or, as necessary, two or more kinds can be used in an arbitrary ratio.

[0131] The amount of the photopolymerizable monomer is preferably 5 parts by mass to 400 parts by mass, and more preferably 10 parts by mass to 300 parts by mass, based on the total mass of the colorant (100 parts by mass), from the viewpoints of light hardenability and developability.

[0132] <Photopolymerization initiator>

[0133] In order to harden the composition by ultraviolet irradiation and form a filter section using a photolithographic method, a photopolymerization initiator can also be contained in the colored composition of the present application. Furthermore, it can be produced in the form of a solvent-developable or alkali-developable photosensitive colored composition.

[0134] As photopolymerization initiators, the following acetophenone compounds can be used: 4-phenoxydichloroacetophenone, 4-tert-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]-1-butanone, or 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butane-1-one; benzoin, benzoin methyl ether, etc. Benzoin-based compounds such as benzoin ether, benzoin isopropyl ether, or benzyl dimethyl ketal; benzophenone-based compounds such as benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4′-methyl diphenyl sulfide, or 3,3′,4,4′-tetra(tert-butylperoxycarbonyl)benzophenone; thioxanthones such as 2-chlorothioxanthones, 2-methylthioxanthones, isopropylthioxanthones, 2,4-diisopropylthioxanthones, or 2,4-diethylthioxanthones; 2,4,6-trichloro-triazine, 2... -Phenylacetyl-4,6-bis(trichloromethyl)-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-triazine, 2-piperyl-4,6-bis(trichloromethyl)-triazine, 2,4-bis(trichloromethyl)-6-styryl-triazine, 2-(naphtho-1-yl)-4,6-bis(trichloromethyl)-triazine, 2-(4-methoxy-naphtho-1-yl)-4,6-bis(trichloromethyl)-triazine, 2,4-trichloromethyl-(piperyl)-6-triazine or 2,4-trichloromethyl-(4′) Triazine compounds such as 1,2-octanedione, 1-[4-(phenylthio)-,2-(O-benzoyl oxime)] or O-(acetyl)-N-(1-phenyl-2-oxo-2-(4′-methoxy-naphthyl)ethylene)hydroxylamine, phosphine compounds such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide or 2,4,6-trimethylbenzoyl diphenylphosphine oxide, quinone compounds such as 9,10-phenanthroquinone, camphorquinone, ethylanthraquinone, borate esters, carbazole compounds, imidazole compounds, or titanium cephalodecyl compounds, etc.

[0135] These photopolymerization initiators can be used alone, or two or more can be mixed in any ratio as needed.

[0136] The content of the photopolymerization initiator is preferably 2 to 200 parts by mass, more preferably 3 to 150 parts by mass, relative to 100 parts by mass of the colorant 100, from the viewpoints of light hardening and developability.

[0137] <photosensitizer>

[0138] Further, a photosensitizer can be contained in the colored composition of the present application.

[0139] As the photosensitizer, the following can be exemplified: unsaturated ketones represented by chalcone derivatives, dibenzalacetone, and the like; 1,2-diketone derivatives represented by benzil or camphorquinone, and the like; benzoin derivatives; fluorene derivatives; naphthoquinone derivatives; anthraquinone derivatives; xanthone derivatives; thioxanthone derivatives; xanthone derivatives; thioxanthone derivatives; coumarin derivatives; ketocoumarin derivatives; cyanine derivatives; merocyanine derivatives; oxonol derivatives; polyformazan pigments such as polymethine pigments represented by acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetraphenylporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetrapyrazinoporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphyrin derivatives, annulene derivatives, spiro-pyrane derivatives, spiro-oxazine derivatives, spiro-thiopyran derivatives, metalloaromatic complex compounds, organoruthenium complex compounds, or Michler's ketone derivatives; bisimidazole derivatives; α-acyloxyester; acylphosphine oxide; methyl phenyl glyoxylate; 9,10-phenanthrenequinone; ethyl anthraquinone; 4,4'-diethyl isophthalophenone; 3,3'-tetra(tert-butylperoxycarbonyl)benzophenone or 4,4'-tetra(tert-butylperoxycarbonyl)benzophenone; 4,4'-diethylaminobenzophenone; and the like.

[0140] These photosensitizers can be used singly or two or more kinds can be used in admixture as necessary, in any ratio.

[0141] Further specifically, mention can be made of the sensitizer described in "Color Handbook" (1986, Kodansha) edited by Shin Tarai et al., "Chemistry of Functional Dyes" (1981, CMC) edited by Shin Tarai et al., and "Special Functional Materials" (1986, CMC) edited by Tadashi Morisato et al., but the present application is not limited to these. In addition, a sensitizer that exhibits absorption of light in the ultraviolet to near-infrared region can also be contained.

[0142] The content of the sensitizer is preferably 3 parts by mass to 60 parts by mass, and more preferably 5 parts by mass to 50 parts by mass, relative to 100 parts by mass of the photopolymerization initiator contained in the colored composition, from the viewpoints of light hardening and development.

[0143] <Thiol compound>

[0144] The colored composition of the present application can contain a thiol compound that functions as a chain transfer agent.

[0145] As the thiol compound, a multifunctional thiol compound having two or more thiol groups is preferable, and mention can be made of, for example, hexanedithiol, decanedithiol, 1,4-butanediol bistrithio-propionate, 1,4-butanediol bistrithio-glycolate, ethylene glycol bistrithio-glycolate, ethylene glycol bistrithio-propionate, trimethylolpropane tristrithio-glycolate, trimethylolpropane tristrithio-propionate, trimethylolpropane tris(3-mercapto butyrate), pentaerythritol tetratrithio-glycolate, pentaerythritol tetratrithio-propionate, tris(2-hydroxyethyl) isocyanurate trithiopropionate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, 2-(N,N-dibutylamino)-4,6-dimercapto-s-triazine, and the like. These multifunctional thiol compounds can be used singly or two or more kinds can be used in an arbitrary ratio as needed.

[0146] The content of the thiol compound is preferably 0.1% by mass to 30% by mass, and more preferably 0.1% by mass to 20% by mass, based on the mass of the total solid components of the colored composition for color filters (100% by mass). If the content of the thiol compound is less than 0.1% by mass, the effect of the addition of the thiol compound is insufficient, and if it exceeds 30% by mass, there is a case where the sensitivity is excessively high and the resolution is rather reduced.

[0147] <Antioxidant>

[0148] The colored composition of the present application can contain an antioxidant. The antioxidant prevents the photopolymerization initiator or the thermohardening compound contained in the colored composition from being oxidized and yellowed due to the heat step at the time of thermal hardening or indium tin oxide (ITO) annealing, and thus the transmittance of the coating film can be improved. Therefore, by including the antioxidant, the yellowing due to oxidation at the time of the heat step can be prevented and a high transmittance of the coating film can be obtained.

[0149] The "antioxidant" in the present application is a compound having ultraviolet absorbing function, radical capturing function or peroxide decomposing function, and specifically, as the antioxidant, hindered phenol-based, hindered amine-based, phosphorus-based, sulfur-based, benzotriazole-based, benzophenone-based, hydroxylamine-based, salicylate-based and triazine-based compounds can be exemplified, and existing ultraviolet absorbers, antioxidants and the like can be used.

[0150] Among these antioxidants, from the viewpoint of balancing the transmittance and the sensitivity of the coating film, as the preferred antioxidant, hindered phenol-based antioxidant, hindered amine-based antioxidant, phosphorus-based antioxidant or sulfur-based antioxidant can be exemplified. Further, hindered phenol-based antioxidant, hindered amine-based antioxidant or phosphorus-based antioxidant is more preferred.

[0151] These antioxidants can be used singly or two or more kinds can be used in an arbitrary ratio as needed.

[0152] In the case where the content of the antioxidant is 0.1 to 5.0 mass% based on the solid content of the color filter coloring composition (100 mass%), the brightness and the sensitivity are good, and therefore this is more preferred.

[0153] <Amine-based compound>

[0154] Further, an amine-based compound having an effect of reducing dissolved oxygen can be contained in the coloring composition of the present application.

[0155] As such an amine-based compound, triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine and the like can be exemplified.

[0156] <Leveling agent>

[0157] In order to make the leveling property of the composition on the transparent substrate good, a leveling agent can be added to the colored composition of the present application. As the leveling agent, a dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable. As a specific example of the dimethylsiloxane having a polyether structure in the main chain, FZ-2122 manufactured by Toray Dow Corning, BYK-333 manufactured by BYK-Chemie, and the like can be given. As a specific example of the dimethylsiloxane having a polyester structure in the main chain, BYK-310, BYK-370 manufactured by BYK-Chemie, and the like can be given. The dimethylsiloxane having a polyether structure in the main chain and the dimethylsiloxane having a polyester structure in the main chain can also be used in combination. The content of the leveling agent is usually preferably 0.003 to 0.5 mass% based on the total mass of the colored composition (100 mass%).

[0158] The leveling agent particularly preferable as the leveling agent is one of so-called surfactants having a hydrophobic group and a hydrophilic group in the molecule, and it is useful to have a feature that although containing the hydrophilic group, the solubility in water is small, the surface tension reducing ability is low in the case of being added to the colored composition, and further, even if the surface tension reducing ability is low, the wettability to the glass plate is good, and the leveling agent which can sufficiently suppress the electrification at the addition amount at which the coating film defects due to foaming do not occur can be preferably used. As the leveling agent having such preferable features, a dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. As the polyalkylene oxide unit, a polyethylene oxide unit, a polypropylene oxide unit, and the dimethylpolysiloxane can have both the polyethylene oxide unit and the polypropylene oxide unit.

[0159] In addition, the bonding form of the polyalkylene oxide unit to the dimethylpolysiloxane can be any one of a pendant type in which the polyalkylene oxide unit is bonded to the side of the repeating unit of the dimethylpolysiloxane, a terminal modification type in which the polyalkylene oxide unit is bonded to the terminal of the dimethylpolysiloxane, and a straight-chain block copolymer type in which the polyalkylene oxide unit is alternately and repeatedly bonded to the dimethylpolysiloxane. The dimethylpolysiloxane having a polyalkylene oxide unit is commercially available from Toray Dow Corning, Inc., and for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ-2207 can be given, but is not limited to these.

[0160] An anionic, cationic, nonionic, or amphoteric surfactant can also be added as an auxiliary to the leveling agent. Two or more kinds of surfactants can be used in combination.

[0161] As anionic surfactants to be added to the leveling agent as an auxiliary, there can be mentioned polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, lauryl sulfate ammonium, stearic acid monoethanolamine, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate, and the like.

[0162] As cationic surfactants to be added to the leveling agent as an auxiliary, there can be mentioned alkyl quaternary ammonium salts or ethylene oxide adducts of these. As nonionic surfactants to be added to the leveling agent as an auxiliary, there can be mentioned polyoxyalkylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate, and other polyoxyalkylene-based surfactants; alkyl betaines such as alkyl dimethyl aminoethyl betaine, and amphoteric surfactants such as alkyl imidazoline; and fluorine-based or silicone-based surfactants.

[0163] <Hardening agent, hardening accelerator>

[0164] In addition, in order to assist the hardening of the thermosetting resin, a hardening agent, a hardening accelerator, and the like can be contained in the colored composition of the present application as necessary. As the hardening agent, phenol-based resins, amine-based compounds, acid anhydrides, active esters, carboxylic acid-based compounds, sulfonic acid-based compounds, and the like are effective, but are not particularly limited to these, and any hardening agent can be used as long as it is a hardening agent that can react with the thermosetting resin. In addition, among these, compounds having two or more phenolic hydroxyl groups in one molecule, amine-based hardening agents can be preferably cited. As the hardening accelerator, for example, amine compounds (such as dicyandiamide, benzyldimethylamine, 4-(dimethylamino)-N,N-dimethylbenzylamine, 4-methoxy-N,N-dimethylbenzylamine, 4-methyl-N,N-dimethylbenzylamine, and the like), quaternary ammonium salt compounds (such as triethylbenzylammonium chloride, and the like), blocked isocyanate compounds (such as dimethylamine, and the like), imidazole derivative bicyclic amidine compounds and salts thereof (such as imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2-ethyl-4-methylimidazole, and the like), phosphorus compounds (such as triphenylphosphine, and the like), guanamine compounds (such as melamine, guanamine, acetoguanamine, benzoguanamine, and the like), S-triazine derivatives (such as 2,4-diamino-6-methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine isocyanuric acid adduct, 2,4-diamino-6-methacryloyloxyethyl-S-triazine isocyanuric acid adduct, and the like), and the like can be used. These can be used alone or in combination of two or more. The content of the hardening accelerator is preferably 0.01 to 15 parts by mass with respect to 100 parts by mass of the thermosetting resin.

[0165] <Other additive components>

[0166] In order to stabilize the viscosity over time, a storage stabilizer can be contained in the colored composition of the present application. In addition, in order to improve the adhesion to a transparent substrate, an adhesion improver such as a silane coupling agent can also be contained.

[0167] As the storage stabilizer, for example, quaternary ammonium chlorides such as benzyldimethylammonium chloride, diethylhydroxylamine, and the like; organic acids such as lactic acid, oxalic acid, and the like, and methyl ethers thereof; t-butylcatechol; organic phosphines such as tetraethylphosphonium, tetraphenylphosphonium, and the like; phosphite salts, and the like can be cited. The storage stabilizer can be used in an amount of 0.1 to 10 parts by mass with respect to 100 parts by mass of the colorant.

[0168] As the adhesion improver, there can be mentioned vinylsilane-based compounds such as vinyltris(β-methoxyethoxy)silane, vinyl ethoxy silane, vinyltrimethoxysilane, and the like; (meth)acrylsilane-based compounds such as γ-methacryloxypropyltrimethoxysilane, and the like; epoxysilane-based compounds such as β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, β-(3,4-epoxycyclohexyl)methyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltriethoxysilane, β-(3,4-epoxycyclohexyl)methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, and the like; aminosilane-based compounds such as N-β(aminoethyl)γ-aminopropyltrimethoxysilane, N-β(aminoethyl)γ-aminopropyltriethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltriethoxysilane, and the like; thiosilane-based compounds such as γ-mercaptopropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, and the like; and the like. The adhesion improver can be used in an amount of 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, relative to 100 parts by mass of the colorant in the colored composition.

[0169] <Method for producing the colored composition>

[0170] The colored composition of the present application is preferably produced by finely dispersing the colorant in a colorant carrier such as a resin and / or a solvent, 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, a ring-type bead mill, or a grinder, together with a dispersing aid such as a pigment derivative or a resin-based dispersant. At this time, two or more kinds of colorants and the like can be simultaneously dispersed in the colorant carrier, or the resulting products obtained by dispersing in the colorant carrier can be mixed. In the case where the solubility of the colorant such as a dye is high, specifically, if the solubility in the solvent used is high, the colorant is dissolved by stirring, and no foreign matter is confirmed, it is not necessary to finely disperse as described above to produce.

[0171] In addition, in the case of use as a photosensitive colored composition (resist material), it can be produced as a solvent developing type or an alkali developing type colored composition. The solvent developing type or the alkali developing type colored composition can be produced by mixing the colorant dispersion, a photopolymerizable monomer and / or a photopolymerization initiator, an optional solvent, other dispersing aids, and additives, and the like. The photopolymerization initiator can be added at the stage of production of the colored composition, or can be added to the produced colored composition thereafter.

[0172] <Dispersing aid>

[0173] When dispersing the colorant in the colorant carrier, it is appropriate to contain a pigment derivative, a resin-type dispersant, a surfactant, and the like as a dispersing aid. The dispersing aid has a large effect of preventing re-agglomeration of the dispersed colorant, and thus the brightness and viscosity stability of the colorant composition obtained by dispersing the colorant in the colorant carrier using the dispersing aid becomes good. As for the pigment derivative and the resin-type dispersant, as explained above.

[0174] <surfactant>

[0175] As the surfactant, anionic surfactants such as sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate ester, and the like; nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonyl phenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate, and the like; cationic surfactants such as alkyl quaternary ammonium salt or an ethylene oxide adduct of these; alkyl betaine such as alkyl dimethyl amino ethyl betaine, amphoteric surfactants such as alkyl imidazoline, and the like can be used alone or in combination of two or more, but are not necessarily limited to these.

[0176] In the case where the surfactant is added, it is preferable to be 0.1 parts by mass to 55 parts by mass, and further preferable to be 0.1 parts by mass to 45 parts by mass, with respect to 100 parts by mass of the colorant. In the case where the blending amount of the surfactant is less than 0.1 parts by mass, it is difficult to obtain the effect after the addition, and if the content is more than 55 parts by mass, there is a case where the dispersion is affected due to the excess dispersant.

[0177] <removal of coarse particles>

[0178] The colorant composition of the present application is preferably subjected to removal of coarse particles of 5 μm or more, preferably 1 μm or more, and further preferably 0.5 μm or more, and dust mixed therewith, by means of centrifugal separation, filtration using a sintered filter or a membrane filter, and the like. As described above, the colorant composition is preferably substantially free of particles of 0.5 μm or more. It is more preferable to be 0.3 μm or less.

[0179] <color filter>

[0180] Next, the color filter of the present application is described.

[0181] The color filter of the present application includes a red filter section, a green filter section, and a blue filter section. In addition, the color filter can further include a magenta filter section, a cyan filter section, and a yellow filter section. With regard to the color filter of the present application, at least one of the red filter sections is formed from the pigment composition of the present application.

[0182] <Method for manufacturing color filter>

[0183] The color filter can be manufactured using a printing method or a photolithography method. With regard to the formation of the filter sections using the printing method, patterning can be achieved simply by repeating printing and drying of the colored composition prepared as a printing ink, and thus the manufacturing method is low in cost and excellent in mass productivity as a color filter. Furthermore, fine patterning with high dimensional accuracy and smoothness can be performed due to the development of printing technology. In order to perform printing, it is preferable that the composition be such that the ink does not dry or cure on a printing plate or on a blanket. In addition, control of the flowability of the ink on a printing machine is also important, and adjustment of the viscosity of the ink can also be performed using a dispersant or a body pigment.

[0184] In the case where the filter sections are formed using the photolithography method, the colored composition prepared as the solvent-developable or alkali-developable colored resist material is applied to a transparent substrate in a dry film thickness of 0.2 μm to 5 μm using a coating method such as spray coating or spin coating, slit coating, roll coating, or the like. The dried film, as necessary, is subjected to exposure (irradiation of a radiation) via a mask having a prescribed pattern disposed in contact with or not in contact with the film. Then, the unhardened portions are removed by immersion in a solvent or an alkali developing solution, or by spraying the developing solution by spraying or the like, to form the desired pattern, and the same operation is repeated for other colors to manufacture the color filter. Furthermore, heating can also be performed as necessary in order to promote polymerization of the colored resist material. According to the photolithography method, a color filter with higher precision than the printing method can be manufactured.

[0185] At the time of development, as the alkali developing solution, an aqueous solution of sodium carbonate, sodium hydroxide, or the like can be used, and an organic base such as dimethylbenzylamine, triethanolamine, or the like can also be used. In addition, a defoaming agent or a surfactant can also be added to the developing solution.

[0186] Furthermore, in order to improve the exposure sensitivity, a water-soluble or alkali-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin, or the like can also be applied and dried after the colored resist is applied and dried, to form a film that prevents polymerization inhibition by oxygen, and then exposure is performed.

[0187] In addition to the method, the color filter of the present application can also be manufactured using an electrodeposition method, a transfer method, an inkjet method, or the like, and the coloring composition of the present application can be used in any of the methods. Furthermore, the electrodeposition method is a method in which, using a transparent conductive film formed on a substrate, each color filter segment is electrodeposited on the transparent conductive film by electrophoresis of colloidal particles, thereby manufacturing a color filter. In addition, the transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet, and the filter segment is transferred to a desired substrate.

[0188] A black matrix can be formed in advance before each color filter segment is formed on a transparent substrate or a reflective substrate. As the black matrix, an inorganic film of chromium or a multilayer film of chromium / chromium oxide, titanium nitride, or the like, or a resin film in which a light shielding agent is dispersed can be used, but is not limited to these. In addition, a thin film transistor (TFT) can also be formed in advance on the transparent substrate or the reflective substrate, and then each color filter segment can be formed. In addition, on the color filter of the present application, an overcoat film or a transparent conductive film, or the like can be formed as needed.

[0189] <liquid crystal display device>

[0190] The liquid crystal display device of the present application includes the color filter of the present application. The color filter of the present application is attached to an opposing substrate using a sealant, liquid crystal is injected from an injection port provided in a seal portion, after which the injection port is sealed, and a polarizing film or a phase difference film is attached to the outside of the substrate as needed, thereby manufacturing a color liquid crystal display device. The color liquid crystal display device can be used in a liquid crystal display mode in which a color filter is used to colorize, such as a Twisted Nematic (TN), a Super Twisted Nematic (STN), an In-Plane Switching (IPS), a Vertically Alignment (VA), an Optically Compensated Bend (OCB), or the like.

[0191] <solid-state imaging element>

[0192] The solid-state imaging element of the present application includes the color filter of the present application. The structure of the solid-state imaging element of the present application is a structure including the color filter for a solid-state imaging element of the present application, and is not particularly limited as long as it functions as a solid-state imaging element, and for example, a structure such as the following can be cited.

[0193] The structure is as follows: a plurality of photodiodes constituting a light-receiving region of a solid-state imaging element (a CCD sensor, a CMOS sensor, an organic CMOS sensor, or the like) and a transfer electrode including polycrystalline silicon or the like are provided on a substrate, a light-shielding film including tungsten or the like that is open only to a light-receiving portion of the photodiode is provided on the photodiode and the transfer electrode, a device protective film including silicon nitride or the like that is formed so as to cover the entire surface of the light-shielding film and the light-receiving portion of the photodiode is provided on the light-shielding film, and a color filter for a solid-state imaging element of the present application is provided on the device protective film.

[0194] Further, it can also be a structure in which a light condensing unit (for example, a microlens or the like; the same applies hereafter) is provided on the device protective film and below the color filter (on the substrate side) or a structure in which a light condensing unit is provided on the color filter or the like.

[0195] Furthermore, the organic CMOS sensor is configured by a full-color photosensitive organic photoelectric conversion film including a thin film as a photoelectric conversion layer and a CMOS signal readout substrate, and is a hybrid structure of two layers in which an organic material carries and converts light into an electric signal and an inorganic material carries and outputs the electric signal to the outside, and in principle, can have an opening ratio of 100% with respect to incident light. The organic photoelectric conversion film is a structure-free continuous film and can be laid on the CMOS signal readout substrate, and thus does not require a fine processing process that is expensive, and is suitable for the fine processing of the filter section.

[0196] The arrangement of the color filter section is not particularly limited, and an existing method can be used.

[0197] In addition, the color filter of the present application can be used not only for a color liquid crystal display device, but also for the manufacture of a color imaging element, an organic EL display device, electronic paper, or the like.

[0198] Embodiment

[0199] Hereinafter, the present application will be described based on an embodiment, but the present application is not limited thereto. Furthermore, in the embodiment, "parts" and "%" respectively mean "mass parts" and "mass %". In addition, the average primary particle diameter of the pigment and the weight average molecular weight (Mw) of the resin are as described below.

[0200] (Average primary particle diameter of pigment)

[0201] The average primary particle diameter of the pigment was determined by using a transmission electron microscope (TEM) and directly measuring the size of the primary particles from the electron micrograph. Specifically, the short axis diameter and the long axis diameter of the primary particles of each pigment were measured, and the average was taken as the particle diameter of the primary particles of the pigment. Next, the volume (mass) of each particle was calculated as a cube approximating the particle diameter, and the volume average particle diameter was taken as the average primary particle diameter, for 100 or more pigment particles.

[0202] (weight average molecular weight (Mw) of the resin)

[0203] The weight average molecular weight (Mw) of the resin was the polystyrene-converted weight average molecular weight (Mw) determined using a TSKgel column (manufactured by Tosoh Corporation) and a gel permeation chromatograph (GPC) equipped with an RI detector (manufactured by Tosoh Corporation, HLC-8120 GPC), using tetrahydrofuran (THF) as the developing solvent.

[0204] Next, the method for producing the resin solution, the resin-type dispersant solution, the pigment derivative, and the colorant used in the examples and comparative examples will be described.

[0205] <Production of the Acrylic Resin Solution>

[0206] (Preparation of Acrylic Resin Solution 1)

[0207] Into a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas introducing tube, a stirring device in a separable four-port flask, 100 parts of propylene glycol monomethyl ether acetate was placed, while injecting nitrogen gas into the vessel, it was heated to 120°C, at the temperature, a mixture of 16.2 parts of styrene, 35.5 parts of glycidyl methacrylate, 25.0 parts of dicyclopentyl methacrylate, 16 parts of methyl methacrylate and 1.0 part of azobisisobutyronitrile as a catalyst required for the reaction as a precursor in this stage was dropped from a dropping tube over 2.5 hours, a polymerization reaction was performed. Next, the inside of the flask was subjected to air replacement, 17.0 parts of acrylic acid and 0.3 parts of tris-dimethylaminomethylphenol and 0.3 parts of hydroquinone as a catalyst required for the reaction as a precursor in this stage were put in, and a reaction was performed at 120°C for 5 hours, a resin solution having a weight average molecular weight of about 12000 (determined by GPC) was obtained. The acrylic acid put in and the epoxy group end of the glycidyl methacrylate constituting unit were ester-bonded, and thus a carboxyl group was not generated in the resin structure. Further, 30.4 parts of tetrahydrophthalic anhydride and 0.5 parts of triethylamine as a catalyst required for the reaction as a precursor in this stage were added, and a reaction was performed at 120°C for 4 hours. One of the two carboxyl groups generated by cleavage of the carboxylic anhydride site of the tetrahydrophthalic anhydride added was ester-bonded with the hydroxyl group in the resin structure, and the other generated a carboxyl end. Propylene glycol monomethyl ether acetate was added so that the non-volatile content became 20%, and thus an acrylic resin solution 1 was obtained.

[0208] (Preparation of Acrylic Resin Solution 2)

[0209] A separable flask with a cooling tube was charged with 100 parts by mass of propylene glycol monomethyl ether acetate, and after nitrogen substitution, the temperature was raised to 90°C. On the other hand, dimethyl-2,2'-[oxybis(methylenebis)]-2-propionate 10.0 parts, cyclohexyl methacrylate 40.1 parts, tetrahydrofurfuryl methacrylate 24.2 parts, methacrylic acid 24.7 parts, t-butyl peroxy-2-ethylhexanoate 2.0 parts, and propylene glycol monomethyl ether acetate 80 parts were mixed in dropping tank 1. Separately, β-mercaptopropionic acid 3.1 parts and propylene glycol monomethyl ether acetate 6 parts were mixed in dropping tank 2. While maintaining the reaction temperature at 90°C, dropping from dropping tank 1 and dropping tank 2 was performed at a constant rate over 2.5 hours. After the dropping was completed, the temperature was maintained at 90°C for 30 minutes, and then t-butyl peroxy-2-ethylhexanoate 0.5 parts was added, and further, the reaction was continued at 90°C for 30 minutes. Then, the reaction temperature was raised to 115°C, and the reaction was continued for 1.5 hours. After temporary cooling to room temperature, glycidyl methacrylate 24.7 parts, 6-t-butyl-2,4-dimethylphenol 0.038 parts, and dimethylbenzylamine 0.38 parts were added, and while bubbling nitrogen-air mixed gas adjusted to an oxygen concentration of 7%, the temperature was raised to 110°C, and the reaction was performed for 6 hours. Then, the temperature was raised to 115°C and the reaction was continued for 2 hours, and the reaction was completed, and the temperature was cooled to room temperature, and about 2 g of a resin solution was sampled and dried by heating at 180°C for 20 minutes, and the nonvolatile content was measured, and propylene glycol monomethyl ether acetate was added to the resin solution synthesized previously so that the nonvolatile content became 20 mass%, and thus an acrylic resin solution 2 was obtained. The weight average molecular weight of the resin was 9000, and the acid value per unit solid content was 70 mgKOH / g.

[0210] <Manufacture of Resin Type Dispersant Solution>

[0211] (Preparation of Resin Type Dispersant Solution 1)

[0212] A flask including a cooling tube, a stirrer was charged with 2,2'-azobisisobutyronitrile (AIBN) 1.0 parts by mass and propylene glycol monomethyl ether acetate 186 parts by mass, and then, methyl methacrylate 27 parts by mass, butyl methacrylate 27 parts by mass, 2-ethylhexyl methacrylate 21 parts by mass, benzyl methacrylate 18 parts by mass, and cumyl phenyl dithioacetate 3.6 parts by mass were charged, and nitrogen substitution was performed for 30 minutes. Then, the temperature of the reaction solution was raised to 60°C while slowly stirring, and active radical polymerization was performed by keeping the temperature for 24 hours. Then, a solution in which AIBN 1.0 parts by mass and dimethylaminoethyl methacrylate 35 parts by mass were dissolved in propylene glycol monomethyl ether acetate 70 parts by mass and nitrogen substitution was performed for 30 minutes was added to the reaction solution, and active radical polymerization was performed at 60°C for 24 hours, whereby a solution of a block copolymer was obtained. To the obtained block copolymer solution, benzyl chloride 25 parts by mass and propylene glycol monomethyl ether 50 parts by mass were added, and a reaction was performed at 80°C for 2 hours, and the solid content concentration was adjusted to 40%, whereby a resin-type dispersant solution 1 was obtained. The resin-type dispersant 1 was a block copolymer including an A block having repeating units derived from methacryloyloxyethyl benzyl dimethyl ammonium chloride and dimethylaminoethyl methacrylate, and a B block having repeating units derived from methyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, and benzyl methacrylate. As a result of proton nuclear magnetic resonance (NMR) measurement, the copolymerization ratio of each repeating unit was methyl methacryloyloxyethyl benzyl dimethyl ammonium chloride / dimethylaminoethyl methacrylate / methyl methacrylate / butyl methacrylate / 2-ethylhexyl methacrylate / benzyl methacrylate = 34 / 4 / 18 / 18 / 14 / 12 (mass ratio).

[0213] (Preparation of resin-type dispersant solution 2)

[0214] A reaction vessel including a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 3-mercapto-1,2-propanediol 6.5 parts, pyromellitic anhydride 4.0 parts, dimethylbenzylamine 0.01 part, and methoxypropyl acetate 41.8 parts, and the inside of the reaction vessel was substituted with nitrogen. The inside of the reaction vessel was heated to 100°C, and the reaction was carried out for 7 hours. It was confirmed by acid value measurement that 98% or more of the anhydride was half-esterified, and then the temperature inside the system was cooled to 70°C, and methyl methacrylate 67 parts, methacrylic acid 5.0 parts, t-butyl acrylate 16.0 parts, (3-ethyloxetane-3-yl)methyl methacrylate 10.0 parts, ethyl acrylate 2.0 parts, and 2,2'-azobisisobutyronitrile 0.10 part and methoxypropyl acetate 60.0 parts were added, and the reaction was carried out for 10 hours. It was confirmed by solid content measurement that 95% was polymerized, and the reaction was ended, and thus a polyester dispersant having an acid value of 47 mgKOH / g and a number average molecular weight of 15000 was obtained. To this, methoxypropyl acetate was added so that the solid content became 40% by solid content measurement, and thus a resin-type dispersant solution 2 having an aromatic carboxyl group was obtained.

[0215] (Preparation of Resin-Type Dispersant Solution 3)

[0216] As the resin-type dispersant solution 3, commercially available "Disperbyk-110 (solid content 52%) manufactured by BYK-Chemie was used.

[0217] <Manufacture of Pigment Derivative>

[0218] (Manufacture of Pigment Derivative 1)

[0219] The pigment derivative 1 represented by the following structure was manufactured with reference to Synthesis Example 3 of Japanese Patent No. 5748665.

[0220] [Chemical Formula 8]

[0221]

[0222] (Manufacture of Pigment Derivative 2)

[0223] As the pigment derivative 2, the organic pigment derivative (D4) of Japanese Patent Laid-Open No. 2010-163500 was used.

[0224] [Chemical Formula 9]

[0225]

[0226] (Manufacture of Pigment Derivative 3)

[0227] The pigment derivative 3 was obtained according to the synthesis method described in Japanese Patent Laid-Open No. 2004-067715.

[0228] [Chemical 10]

[0229]

[0230] (Production of Pigment Derivative 4)

[0231] Pigment derivative 4 represented by the following structure was produced with reference to Production Example 6 of Japanese Patent No. 4983061.

[0232] [Chemical 11]

[0233]

[0234] <Method for Producing a Colorant>

[0235] <Production of Diketopyrrolopyrrole Pigment of General Formula (2)>

[0236] (Production of Diketopyrrolopyrrole Pigment (A2-1))

[0237] Under a nitrogen atmosphere, a solution of an alkoxide was prepared by adding 200 parts of t-amyl alcohol, which had been dehydrated with molecular sieves, and 140 parts of sodium t-amylate into a stainless steel reaction vessel equipped with a reflux condenser, and heating to 100°C while stirring. Separately, a solution of these components was prepared by adding 88 parts of diisopropyl succinate and 122.5 parts of 4-propylbenzonitrile into a glass flask, heating to 90°C while stirring, and dissolving. To the heated solution of these components, the solution of the alkoxide heated to 100°C was added dropwise at a constant rate over a period of 2 hours while stirring vigorously. After the completion of the dropwise addition, heating and stirring were continued at 90°C for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole compound. Further, methanol 600 parts, water 600 parts, and acetic acid 304 parts were added to a reaction vessel equipped with a glass jacket, and cooled to -10°C. To the cooled mixture, the previously obtained solution of the alkali metal salt of the diketopyrrolopyrrole compound cooled to 75°C was added little by little over a period of about 120 minutes while rotating a shearing disc having a diameter of 8 cm at 4000 rpm using a high-speed stirring disperser. At this time, the temperature of the mixture of methanol, acetic acid, and water was kept at a temperature of -5°C or lower, and the addition rate of the alkali metal salt of the diketopyrrolopyrrole compound at 75°C was adjusted, and the addition was carried out little by little over a period of about 120 minutes. After the addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed using an ultrafiltration device at 5°C, and then filtered to obtain a red paste. The paste was redispersed in methanol 3500 parts cooled to 0°C to form a suspension having a methanol concentration of about 90%, and stirred at 5°C for 3 hours to perform particle size adjustment and washing with crystallization transfer. Subsequently, the obtained aqueous paste of the diketopyrrolopyrrole compound was filtered using an ultrafiltration device, dried at 80°C for 24 hours, and pulverized to obtain 129.6 parts of a diketopyrrolopyrrole pigment of the following formula (A2-1).

[0238] [Chemical Formula 12]

[0239]

[0240] (Production of diketopyrrolopyrrole pigment (A2-2))

[0241] The production was carried out in the same manner as in the production of diketopyrrolopyrrole pigment (A2-1), except that 4-propylbenzonitrile 122.5 parts was changed to 4-tert-butylbenzonitrile 134.4 parts, to obtain 135.4 parts of a diketopyrrolopyrrole pigment represented by the following formula (A2-2).

[0242] [Chemical Formula 13]

[0243]

[0244] (Production of diketopyrrolopyrrole pigment (A2-3))

[0245] Except that 4-propylbenzonitrile 122.5 parts is changed to 3-tert-butylbenzonitrile 134.4 parts, the same as the production of diketopyrrolopyrrole pigment (A2-1) is performed, and diketopyrrolopyrrole pigment represented by the following formula (A2-3) 133.4 parts is obtained.

[0246] [Chemical 14]

[0247]

[0248] (Production of diketopyrrolopyrrole pigment (A2-4))

[0249] Except that 4-propylbenzonitrile 122.5 parts is changed to 4-(2-ethylhexyl)benzonitrile 181.7 parts, the same as the production of diketopyrrolopyrrole pigment (A2-1) is performed, and diketopyrrolopyrrole pigment represented by the following formula (A2-4) 173.3 parts is obtained.

[0250] [Chemical 15]

[0251]

[0252] (Production of diketopyrrolopyrrole pigment (A2-5))

[0253] Except that 4-propylbenzonitrile 122.5 parts is changed to 4-dodecylbenzonitrile 229.1 parts, the same as the production of diketopyrrolopyrrole pigment (A2-1) is performed, and diketopyrrolopyrrole pigment represented by the following formula (A2-5) 206.2 parts is obtained.

[0254] [Chemical 16]

[0255]

[0256] (Production of diketopyrrolopyrrole pigment (A2-6))

[0257] Except that 4-propylbenzonitrile 122.5 parts is changed to 4-octadecylbenzonitrile 300.1 parts, the same as the production of diketopyrrolopyrrole pigment (A2-1) is performed, and diketopyrrolopyrrole pigment represented by the following formula (A2-6) 238.8 parts is obtained.

[0258] [Chemical 17]

[0259]

[0260] (Production of other diketopyrrolopyrrole pigments)

[0261] (Production of diketopyrrolopyrrole pigment (A3-1))

[0262] To a reaction vessel 1, tert-amyl alcohol 220 parts was added, while performing water bath cooling, 60% NaH 32 parts was added and heated and stirred at 90°C. Next, in a reaction vessel 2, tert-amyl alcohol 100 parts, a compound of the following formula (700) 99.2 parts synthesized by the method of "Tetrahedron", 58 (2002) 5547-5565, and a benzonitrile compound of formula (N-1) 71.8 parts were heated and dissolved, and the resultant was added dropwise to the reaction vessel 1 over 2 hours. After reaction at 120°C for 10 hours, and cooling to 60°C, methanol 400 parts and acetic acid 50 parts were added, and filtration separation and methanol washing were performed, to obtain diketopyrrolopyrrole pigment represented by formula (A3-1) 79.1 parts.

[0263] [Chemical 18]

[0264]

[0265] [Chemical 19]

[0266]

[0267] (Production of diketopyrrolopyrrole pigment composition)

[0268] [Example 1]

[0269] (Production of diketopyrrolopyrrole pigment composition (P-1))

[0270] C.I. Pigment Red 254 ("Cinilex DPP Red ST" by CINIC Corporation) 97.0 parts, formula (A2-1) 3.0 parts, sodium chloride 1000 parts, and diethylene glycol 120 parts were charged into a stainless 1 gallon kneader (manufactured by Inoue Mfg.) and mixed at 60°C for 12 hours. Next, the mixed mixture was put into warm water, stirred while heating to about 80°C for 1 hour to make a slurry, and filtration and water washing were performed to remove sodium chloride and diethylene glycol, and then dried at 80°C for one day and night, and pulverized, to thereby obtain diketopyrrolopyrrole pigment composition (P-1) 98.3 parts. The average primary particle diameter was 28.5 nm.

[0271] [Examples 2 to 14]

[0272] (Production of diketopyrrolopyrrole pigment composition (P-2 to P-14))

[0273] The diketopyrrolopyrrole pigment composition (P-2 to P-14) was obtained by the same method as in Example 1 except that "C.I. Pigment Red 254 (Cinilex DPP Red ST by CINIC Corporation) 97.0 parts, formula (A2-1) 3.0 parts" was changed to the kind and amount of diketopyrrolopyrrole pigment and pigment derivative described in Table 1. The average primary particle diameter of each pigment composition was as described in Table 1.

[0274] [Comparative Examples 1 to 6]

[0275] (Production of diketopyrrolopyrrole pigment composition (P-S1 to P-S6))

[0276] The diketopyrrolopyrrole pigment composition (P-S1 to P-S6) was obtained by the same method as in Example 1 except that "C.I. Pigment Red 254 (Cinilex DPP Red ST by CINIC Corporation) 97.0 parts, formula (A2-1) 3.0 parts" was changed to the kind and amount of diketopyrrolopyrrole pigment and pigment derivative described in Table 1. The average primary particle diameter of each pigment composition was as described in Table 1.

[0277]

[0278] <Production of diketopyrrolopyrrole colorant composition>

[0279] [Example 101]

[0280] (Production of diketopyrrolopyrrole colorant composition (DR-1))

[0281] A mixture of the following composition was mixed in a uniform manner, then dispersed for 5 hours using zirconia beads of 0.5 mm in diameter and an Eiger-mill (minimodel M-250MKII by Eiger Japan Co., Ltd.), and then filtered using a filter with a pore size of 5.0 μm, thereby producing the colorant composition (DR-1).

[0282]

[0283] [Examples 102 to 114, Comparative Examples 101 to 106]

[0284] (Production of diketopyrrolopyrrole colorant composition (DR-2 to DR-14, DR-S1 to DR-S6))

[0285] The colored composition (DR-2 to DR-14, DR-S1 to DR-S6) was produced in the same manner as the colored composition (DR-1), except that the diketopyrrolopyrrole pigment composition (P-1) was changed to the pigment composition shown in Table 2.

[0286] <Production of Other Colored Compositions>

[0287] (Production of PR177 Colored Composition (DR-177A) for Tinting)

[0288] The following mixture was mixed by stirring in a uniform manner, then dispersed using zirconium oxide beads of 0.5 mm in diameter and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan) for 5 hours, and then filtered using a filter having a pore size of 5.0 μm, thereby producing the PR177 colored composition (DR-177A).

[0289]

[0290] <Evaluation of Colored Compositions>

[0291] The obtained colored compositions (DR-1 to DR-14, DR-S1 to DR-S6) were evaluated by the following methods. The results are shown in Table 2.

[0292] (Evaluation of Contrast Ratio)

[0293] Using a spin coater, the colored composition (DR-1 to DR-14, DR-S1 to DR-S6) was coated on a 100 mm x 100 mm, 1.1 mm thick glass substrate, warmed at 80°C for 15 minutes in a clean oven to remove the solvent, heated at 230°C for 60 minutes in a clean oven, and after standing to cool, a red colored film substrate was obtained. Further, the red colored film substrate after heat treatment at 230°C conformed to a chromaticity of x = 0.660 under a C light source. Next, the measuring method of the contrast ratio will be explained. Light emitted from a backlight unit for liquid crystal displays is polarized by a polarizing plate and reaches the polarizing plate through the dried coating film of the colored composition coated on the glass substrate. If the polarizing plate and the polarizing plane of the polarizing plate are parallel, the light passes through the polarizing plate, but in the case of being orthogonal, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the dried coating film of the colored composition, scattering and the like caused by the pigment particles occur, and if a shift occurs in a part of the polarizing plane, the amount of light passing through the polarizing plate when the polarizing plates are parallel decreases, and a part of the light passes through the polarizing plate when the polarizing plates are orthogonal. The passing light was measured as the luminance on the polarizing plate, and the ratio of the luminance when the polarizing plates are parallel to the luminance when the polarizing plates are orthogonal (contrast ratio) was calculated. Further, as a luminance meter, a color luminance meter ("BM-5A" manufactured by Topcon Corporation) was used, and as a polarizing plate, a polarizing plate ("NPF-G1220DUN" manufactured by Nitto Electric Industrial Co., Ltd.) was used. Further, at the time of measurement, in order to block unnecessary light, a black mask having a 1 cm square hole was interposed in the measurement portion.

[0294] (Contrast ratio) = (luminance when parallel) / (luminance when orthogonal)

[0295] The contrast ratio was evaluated in the following 4 stages.

[0296] ◎: 5000 or more (excellent)

[0297] O: 4000 or more but less than 5000 (good: practicality possible)

[0298] Δ: 3000 or more but less than 4000 (poor)

[0299] X: less than 3000 (very poor)

[0300] (Evaluation of storage stability)

[0301] For the colored compositions (DR-1 to DR-14, DR-S1 to DR-S6), the initial viscosity at 25°C was measured using a type E viscometer ("ELD type viscometer" manufactured by Tokimec, Inc.). Subsequently, the viscosity after the lapse of time was measured using the same method as the viscosity measurement after the mixture was stored in a thermostat at 40°C for two weeks and the lapse of time was promoted, the rate of change in the viscosity before and after the mixture was stored at 40°C for two weeks was calculated, and the evaluation was performed in three stages by the following criteria.

[0302] : The absolute value of the rate of change in the viscosity was not more than 10% (good)

[0303] : The absolute value of the rate of change in the viscosity was 10% to 20% (ordinary)

[0304] : The absolute value of the rate of change in the viscosity was more than 20% (poor)

[0305] [Table 2]

[0306]

[0307] As shown in Table 2, the colored compositions using diketopyrrolopyrrole pigment compositions of the present application were good in both the contrast ratio and the storage stability.

[0308] [Method for producing a photosensitive colored composition]

[0309] [Example 201]

[0310] (Production of a photosensitive colored composition (RR-1))

[0311] A mixture having the following composition was uniformly mixed by stirring, and then filtered using a filter having a pore size of 1.0 μm, thereby obtaining a red photosensitive colored composition (RR-1).

[0312]

[0313]

[0314] [Examples 202 to 214, Comparative Examples 201 to 206]

[0315] (Production of photosensitive colored compositions (RR-2 to RR-14, RR-S1 to RR-S6))

[0316] The total content of the coloring composition in the photosensitive coloring composition was fixed at 50.00 parts, and the types and mixing ratios of the coloring compositions were varied. Otherwise, the photosensitive coloring compositions (RR-2 to RR-14, RR-S1 to RR-S6) were obtained in the same manner as in Example 201. The types of coloring compositions were set as shown in Table 3, and the mixing ratios of the coloring compositions were set to the ratio of the chromaticity of the substrate after fabrication to (x = 0.660, y = 0.324) under a C light source.

[0317] [Example 215]

[0318] (Preparation of the photosensitive coloring composition (RR-15))

[0319] The mixture of the following components is stirred and mixed evenly, and then filtered through a filter with a pore size of 1.0 μm to obtain a red photosensitive coloring composition (RR-15).

[0320]

[0321] Evaluation of Photosensitive Coloring Compositions

[0322] The obtained photosensitive coloring compositions were evaluated using the methods described below. The results are shown in Table 3.

[0323] (Brightness rating)

[0324] Using a spin coater, photosensitive coloring compositions (RR-1 to RR-15, RR-S1 to RR-S6) were coated onto 100mm × 100mm, 1.1mm thick glass substrates. The solvent was removed by heating at 80°C for 15 minutes in a clean oven to obtain the coating. Subsequently, an ultra-high pressure mercury lamp with a cumulative light intensity of 100mJ / cm² was used. 2 The substrate was exposed to ultraviolet light and developed using an alkaline developer at 23°C to obtain a coated substrate. Subsequently, it was heated at 230°C for 30 minutes in a clean oven, cooled, and the lightness Y(C) of the obtained coated substrate was measured using a microspectrophotometer (OSP-SP100, Olympus Optical Co., Ltd.). Furthermore, the red coated substrate, after heat treatment at 230°C, met the colorimetric standard of (x = 0.660, y = 0.324) under C light. The alkaline developer used contained 1.5% by mass sodium carbonate, 0.5% by mass sodium bicarbonate, 8.0% by mass anionic surfactant (Pelex NBL, Kao Corporation), and 90% by mass water. The lightness was evaluated using the following four stages.

[0325] ◎: 18.5 or above (Extremely good)

[0326] O: 18.3 or more but less than 18.5 (good)

[0327] Δ: 18.1 or more but less than 18.3 (poor)

[0328] X: less than 18.1 (very poor)

[0329] (Evaluation of contrast ratio)

[0330] The contrast ratio measurement was performed using the substrate used in the evaluation of the brightness. The evaluation of the contrast ratio was performed in the following 4 stages.

[0331] O: 4000 or more but less than 5000 (good)

[0332] O: 4000 or more but less than 5000 (good)

[0333] Δ: 3000 or more but less than 4000 (poor)

[0334] X: less than 3000 (very poor)

[0335] (Evaluation of storage stability)

[0336] For the obtained photosensitive colored composition, the initial viscosity at 25°C was measured using an E-type viscometer ("ELD-type viscometer" manufactured by Tokimec, Inc.). Subsequently, the viscosity after the lapse of time was measured after the storage for two weeks in a constant temperature chamber at 40°C, and the rate of change of the viscosity before and after the storage for two weeks at 40°C was calculated, and the evaluation was performed in 3 stages by the following criteria.

[0337] O: 4000 or more but less than 5000 (good)

[0338] O: 4000 or more but less than 5000 (good)

[0339] X: less than 3000 (very poor)

[0340] (Evaluation of heat resistance)

[0341] Using a spin coater, the photosensitive colored composition (RR-1 to RR-15, RR-S1 to RR-S6) was coated on a glass substrate of 100 mm x 100 mm and 1.1 mm thick, and the solvent was removed by heating at 70°C for 15 minutes in a clean oven to obtain a dried coating film. At this time, the coating was performed in such a manner that the dried coating film becomes 2.5 μm. Subsequently, using an ultrahigh pressure mercury lamp, light was irradiated through a photomask having a 100 μm wide (pitch 200 μm) stripe pattern at a cumulative light amount of 100 mJ / cm 2The substrate was subjected to ultraviolet exposure and developed with an alkaline developer at 23°C to obtain a striped coating film substrate. Subsequently, the substrate was subjected to a heat treatment at 230°C for 60 minutes, and then further subjected to a heat treatment at 240°C for 60 minutes and a heat treatment at 280°C for 60 minutes. The coating film surface of the substrate after the heat treatment was observed with an optical microscope, and the presence or absence of crystallization was determined based on the following four-stage criteria.

[0342] ◎...No crystallization after the heat treatment at 230°C for 60 minutes, the heat treatment at 240°C for 60 minutes, and the heat treatment at 280°C for 60 minutes

[0343] ○...No crystallization after the heat treatment at 230°C for 60 minutes and the heat treatment at 240°C for 60 minutes, but crystallization after the heat treatment at 280°C for 60 minutes

[0344] △...No crystallization after the heat treatment at 230°C for 60 minutes, but crystallization after the heat treatment at 240°C for 60 minutes

[0345] ×...Crystallization after the heat treatment at 230°C for 60 minutes

[0346] (Evaluation of Solvent Resistance)

[0347] A photosensitive colored composition (RR-1 to RR-15, RR-S1 to RR-S6) was applied to a glass substrate of 100 mm x 100 mm and 1.1 mm thick using a spin coater, and the substrate was warmed at 70°C for 15 minutes in a clean oven to remove the solvent, thereby obtaining a dried coating film. At this time, the application was performed in such a manner that the dried coating film became 2.5 μm. Subsequently, the substrate was subjected to ultraviolet exposure using an ultrahigh pressure mercury lamp through a photomask having a 100 μm wide (pitch: 200 μm) striped pattern at a cumulative light quantity of 100 mJ / cm 2 The substrate was subjected to ultraviolet exposure and developed with an alkaline developer at 23°C to obtain a striped coating film substrate. Subsequently, the substrate was subjected to a heat treatment at 230°C for 60 minutes in a clean oven. At this time, the colorimetric values (L*(1), a*(1), b*(1)) under a C light source were measured, and then the substrate was immersed in N-methyl pyrrolidone (NMP) at 40°C for 30 minutes, and then the colorimetric values (L*(2), a*(2), b*(2)) under a C light source were measured. The color difference ΔE*ab was calculated from the colorimetric values before and after the immersion in NMP according to the following calculation formula, and the solvent resistance of the coating film was evaluated according to the following three stages.

[0348] Calculation formula: ΔE*ab = [[L*(2) - L*(1)] 2 + [a*(2) - a*(1)]2 +[b*(2)-b*(1)] 2 ] 1 / 2

[0349] ◎: ΔE*ab is less than 1.0 (extremely good)

[0350] ○: ΔE*ab is 1.0 or higher but less than 3.0 (Good)

[0351] △: ΔE*ab is 3.0 or higher but less than 5.0 (unacceptable)

[0352] ×: ΔE*ab is 5.0 or higher (extremely poor)

[0353] (Evaluation of transmissibility)

[0354] The photosensitive coloring composition was coated onto a glass substrate using a slit-plate coater, followed by pre-baking at 90°C for 2 minutes to form a 2.4 μm thick coating. The coated substrate was then cooled to room temperature, and a high-pressure mercury lamp was used with a striped photomask at 1000 J / m². 2 The exposure amount for the coating included radiation at wavelengths of 365 nm, 405 nm, and 436 nm. Alkali development was performed, followed by rinsing with ultrapure water, and then baking at 230°C for 20 minutes to form red striped pixels on the substrate. The transmittance (T1) at 520 nm on a glass substrate 8 μm away from the red striped pixels was then measured. Next, acrylic resin solution 2 was coated onto the substrate using a slot die coater, followed by pre-baking at 90°C for 2 minutes to form a coating with a thickness of 2.5 μm. This was then baked at 230°C for 20 minutes. The transmittance (T2) at 520 nm on a glass substrate 8 μm away from the red striped pixels was then measured. The difference between T1 and T2 was taken as ΔT (%) and evaluated in four stages as described below. The smaller the ΔT value, the less the brightness reduction caused by color migration to adjacent color filter segments, which can be said to suppress color migration.

[0355] ◎: ΔT less than 1.0% (Extremely good)

[0356] ○: ΔT is 1.0% or higher but less than 2.0% (Good)

[0357] △: ΔT is 2.0% or higher but less than 3.0% (unfavorable)

[0358] ×: ΔT is above 3.0% (extremely poor)

[0359] [Table 3]

[0360]

[0361]

[0362] As shown in Table 3, the brightness, contrast ratio, storage stability, heat resistance, solvent resistance, and bleeding of the photosensitive coloring compositions of Examples 201 to 215, which contain diketopyrrolopyrrole pigments of General Formula (1) and General Formula (2) in a mass ratio ranging from 99.9:0.1 to 90.0:10.0, as a feature of the present application, were all particularly good results without any practical problems. On the other hand, Comparative Example 210, Comparative Examples 203 to 205, which do not contain diketopyrrolopyrrole pigments of General Formula (2), were inferior to the Examples in the crystallization precipitation in the heating step, and the brightness or contrast ratio was also inferior to the results of the Examples due to the influence of the crystallization precipitation. In addition, Comparative Example 202 or Comparative Example 206, which contains diketopyrrolopyrrole pigments of General Formula (2) in an amount of more than 10 mass%, was inferior to the Examples in the stability, solvent resistance, and bleeding. It is considered that the reason for this is that the dispersion stability, solvent resistance, and bleeding of diketopyrrolopyrrole pigments of General Formula (2) themselves are inferior to those of diketopyrrolopyrrole pigments of General Formula (1).

[0363] <Manufacture of color filter>

[0364] First, a photosensitive coloring composition for green and blue for manufacturing a color filter was manufactured.

[0365] (Manufacture of green photosensitive coloring composition (RG-100))

[0366] A mixture of the following composition was mixed by stirring in a uniform manner, and then dispersed for 5 hours using zirconia beads of 0.5 mm in diameter and an Eiger-mill ("minimodel M-250 MKII" manufactured by Eiger Japan Co.) and then filtered using a filter with a pore size of 5.0 μm, thereby manufacturing a green coloring composition (DG-100).

[0367]

[0368] Subsequently, a mixture of the following composition was mixed by stirring in a uniform manner, and then filtered using a filter with a pore size of 1.0 μm, thereby manufacturing a green photosensitive coloring composition (RG-100).

[0369]

[0370]

[0371] (Preparation of blue photosensitive coloring composition (RB-100))

[0372] The mixture of the following components was stirred and mixed in a homogeneous manner, and then dispersed for 5 hours using 0.5 mm diameter zirconia beads in an Eiger mill (M-250MKII minimodel manufactured by Eiger Japan). The mixture was then filtered using a 5.0 μm pore size filter to produce a blue coloring composition (DB-100).

[0373]

[0374] The mixture of the following components was then stirred and mixed in a homogeneous manner, and then filtered using a filter with a pore size of 1.0 μm to prepare a blue photosensitive coloring composition (RB-100).

[0375]

[0376] (Fabrication of color filters for liquid crystal display devices)

[0377] A black matrix is ​​patterned on a glass substrate, and the red photosensitive coloring composition (RR-14) of the present invention is coated onto the substrate using a spin coater to form a colored film. The film is then protected by a photomask and irradiated with an ultra-high pressure mercury lamp at 200 mJ / cm². 2 The substrate is then exposed to ultraviolet light. Next, it is spray-developed using an alkaline developer containing 0.2% sodium carbonate aqueous solution to remove unexposed areas. After washing with deionized water, the substrate is heated at 230°C for 30 minutes to form a red filter segment. Here, the red filter segment is designed to have a chromaticity of x = 0.660 under a C light source after heat treatment at 230°C. Similarly, using the same method, a green filter segment is formed with a green photosensitive coloring composition (RG-100) to achieve a chromaticity of y = 0.570, and a blue filter segment is formed with a blue photosensitive coloring composition (RB-100) to achieve a chromaticity of y = 0.045, thus obtaining a color filter.

[0378] By using the photosensitive coloring composition (RR-14) of the present invention in the formation of the red filter section, high brightness and high contrast of the color filter can be achieved, and it is suitable for use without any problems in other physical properties. In addition, by using a sealant to bond the color filter of the present invention to the opposing substrate, injecting liquid crystal through the injection port provided in the sealing part, sealing the injection port, and bonding the polarizing film or retardation film to the outside of the substrate, a liquid crystal display device with excellent brightness and contrast ratio is obtained.

[0379] (Manufacture of color filter for solid-state image pickup element)

[0380] On a 6-inch silicon wafer, a resist liquid for planarization film (HL-18s; manufactured by Nippon Steel Chemical Co., Ltd.) was coated by a spin coating method, and as a pre-baking, a heating treatment was performed using a hot plate at 100°C for 6 minutes. Further, a treatment was performed using an oven at 230°C for 1 hour to harden the coated film, thereby forming a planarization film of 1.0 μm, and thus a wafer with a planarization film was obtained.

[0381] A green photosensitive coloring composition (RG-100) was coated on the silicon wafer with a planarization film using a spin coater, and as a pre-baking, a heating treatment was performed using a hot plate at 100°C for 1 minute. The film thickness after the pre-baking was adjusted to 0.9 μm.

[0382] Subsequently, an i-ray stepper exposure device FPA-3000i5+ (manufactured by Canon, Inc.) was used to perform an exposure at a wavelength of 365 nm with an exposure amount of 150 mJ / cm 2 Pattern exposure was performed.

[0383] The coated film after the exposure was subjected to a 1-minute spin immersion development using an organic alkali developer. After the spin immersion development, a 20-second rinsing was performed using pure water in a spin spray manner, and further, a 20-second water washing was performed using pure water. Then, the water droplets remaining on the wafer were blown away using high-pressure air, and the substrate was naturally dried, and further, a heating treatment was performed on a hot plate at a surface temperature of 230°C for 5 minutes to form a square pixel pattern. The film thickness of the green pattern after the heating treatment was 0.80 μm.

[0384] Next, a red photosensitive coloring composition (RR-12) was used to form a red coloring pixel layer in the same manner as the green coloring pixel layer, and further, a blue photosensitive coloring composition (RB-100) was used to form a blue coloring pixel layer, thereby obtaining a color filter for a solid-state image pickup element. The color filter for a solid-state image pickup element manufactured in the described manner has very good spectral characteristics of red and excellent heat resistance, and thus the skin color reproduction of a solid-state image pickup element using the color filter for a solid-state image pickup element is particularly excellent.

Claims

1. A pigment composition for color filters, comprising a diketylpyrrolopyrrole pigment (A1) represented by general formula (1) and a diketylpyrrolopyrrole pigment (A2) represented by general formula (2), characterized in that, The diketopyrrolopyrrole pigment (A2) is at least one compound selected from the group of chemical formulas 1, and the mass ratio of the diketopyrrolopyrrole pigment (A1) to the diketopyrrolopyrrole pigment (A2) is 99.9:0.1 to 90.0:10.0; General formula (1) In general formula (1), X represents a halogen atom. General formula (2) In general formula (2), Y and Z independently represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group with 1 to 20 carbon atoms that may have substituents, or a phenyl group that may have substituents; wherein at least one of Y and Z is an alkyl group with 3 to 18 carbon atoms. Chemical Formula Group 1 2. The pigment composition for color filters according to claim 1, characterized in that, It also contains pigment derivatives.

3. A coloring composition for a color filter, characterized in that, It contains a colorant, a resin, and a solvent, wherein the colorant contains a pigment composition for color filters as described in claim 1 or 2.

4. The coloring composition for a color filter according to claim 3, characterized in that, It also contains one or more of a photopolymerizable monomer and a photopolymerization initiator.

5. A color filter, characterized in that, Includes filter segments formed from the coloring composition for color filters as described in claim 3 or 4.

6. A liquid crystal display device, characterized in that, Includes the color filter as described in claim 5.

7. A solid-state imaging element, characterized in that, Includes the color filter as described in claim 5.

Images