Color Filter Coloring Composition, Color Filter, Liquid Crystal Display Device, and Solid-State Imaging Device

Abstract

To form a pixel which has superior storage stability, and is excellent in lightness, contrast ratio, heat resistance, and resistance to a solvent.SOLUTION: A coloring composition for color filter includes a red pigment, a diketopyrrolopyrrole pigment dispersant (A), a resin type dispersant (B) having a basic group, and a binder resin (C). Here, (A) includes a pigment dispersant expressed by Formula (1).SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] The present invention relates to a color filter used in the manufacture of a color liquid crystal display device, a solid-state imaging device typified by a C-MOS (Complementary Metal Oxide Semiconductor), a CCD (Charge Coupled Device), an organic EL display device, and electronic paper, a color filter including a filter segment formed using the same, and a liquid crystal display device and a solid-state imaging device including the color filter.

Background Art

[0002] On the color filter used in a color liquid crystal display device, a transparent electrode for driving liquid crystal is generally formed by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is further formed thereon. In order to sufficiently obtain the performance of these transparent electrodes and alignment films, the forming process generally needs to be performed at a high temperature of 230°C or higher, and heat resistance is required for the color filter.

[0003] Important quality items required for a color filter include contrast ratio and brightness. When a color filter with a low contrast ratio is used, the degree of polarization controlled by the liquid crystal is disturbed, and light leaks when the light should be blocked (OFF state), or the transmitted light attenuates when the light should be transmitted (ON state), resulting in a blurred screen. Therefore, in order to realize a high-quality liquid crystal display device, it is essential to increase the contrast ratio. In addition, when a color filter with low brightness is used, since the light transmittance is low, the screen becomes dark, and in order to obtain a bright screen, it is necessary to increase the number of backlights as the light source. However, from the viewpoint of suppressing power consumption, increasing the brightness of the color filter has become a trend.

[0004] As colorants used for forming red filter segments, C.I. Pigment Red 254, C.I. Pigment Red 291, C.I. Pigment Red 242, and C.I. Pigment Red 177 have been generally widely used. C.I. Pigment Red 254 and C.I. Pigment Red 291, which are diketopyrrolopyrrole pigments, are particularly excellent in lightness. However, in recent years, there has been a strong demand for higher contrast in color filters, and for this purpose, it is necessary to minimize the primary particle size of diketopyrrolopyrrole-based pigments as much as possible. However, the refined diketopyrrolopyrrole-based pigments have the property of being prone to crystal growth due to intermolecular hydrogen bonding, so crystallization occurs in the heating process when forming a color filter, and the generation of foreign matter has become a problem.

[0005] Patent Document 1 discloses that by using C.I. Pigment Red 291 and a diketopyrrolopyrrole pigment with a specific structure in combination, crystal precipitation in the heating process can be suppressed. However, further improvement has been required in terms of lightness, contrast ratio, heat resistance, and solvent resistance.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0007] An object of the present invention is to provide a color filter coloring composition capable of forming pixels with excellent storage stability, good lightness, contrast ratio, heat resistance, and solvent resistance, a color filter including a filter segment formed using the same, and a liquid crystal display device and a solid-state imaging device including the color filter.

Means for Solving the Problems

[0008] As a result of intensive studies, the inventors of the present invention have found that by using a specific diketopyrrolopyrrole-based pigment dispersant and a basic resin-type dispersant, a color filter coloring composition excellent in storage stability, high brightness, high contrast ratio, and suppressed crystal precipitation during the heating process and having good solvent resistance can be obtained, leading to the present invention.

[0009] That is, the present invention relates to a color filter coloring composition containing a red pigment, a diketopyrrolopyrrole-based pigment dispersant (A), a resin-type dispersant (B) having a basic group, and a binder resin (C), wherein the diketopyrrolopyrrole-based pigment dispersant (A) contains a pigment dispersant represented by the following general formula (1).

[0010] General formula (1) [Chemical formula] [In general formula (1), R1 to R 10 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a cyano group, an unsubstituted alkyl group having 1 to 20 carbon atoms, an alkyl group having an ether bond and 1 to 20 carbon atoms, a phenyl group which may have a substituent, -CF3, -OR 11 , -SR 12 , -N(R 13 )R 14 , -SO3M, -SO2NHR 15 , or -SO2N(R 16 )R 17 , and R 11 to R 17 are each independently an unsubstituted alkyl group having 1 to 20 carbon atoms, an alkyl group having an ether bond and 1 to 20 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent. Among R1 to R 10 , at least one is an alkyl group having 3 to 18 carbon atoms, -OR 11 , -SR 12 , -N(R 13 )R 14 , -SO2NHR 15 , or -SO2N(R 16 )R17 -SO3M represents a sulfo group or a metal salt or alkylammonium salt of a sulfo group.

[0011] The present invention also relates to the colored composition for a color filter, characterized in that the resin-type dispersant (B) having a basic group has at least one structural unit selected from the group consisting of structural units represented by the following general formula (2), general formula (3) and general formula (4).

[0012] General formula (2) [Chemical formula] [In general formula (2), R 201 ~R 203 each independently represents a hydrogen atom or a linear or cyclic hydrocarbon group which may have a substituent, and two or more of R 201 ~R 203 may be bonded to each other to form a cyclic structure. R 204 represents a hydrogen atom or a methyl group, L represents a divalent linking group, and W- represents a counter anion.

[0013] General formula (3) [Chemical formula]

[0014] [In general formula (3), R 205 and R 206 each independently represents a hydrogen atom or a linear or cyclic hydrocarbon group which may have a substituent, and R 205 and R 206 may be bonded to each other to form a cyclic structure. R 204 represents a hydrogen atom or a methyl group, and L represents a divalent linking group.

[0015] General formula (4) [Chemical formula] [In general formula (4), R 207 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, an acyl group, an oxyradical group, or OR 212 , R 212 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an acyl group, R 208 , R 209 , R 210 , R 211 each independently represents a methyl group, an ethyl group, or a phenyl group. R 204 represents a hydrogen atom or a methyl group, and L represents a divalent linking group.]

[0016] Further, the present invention relates to the color filter coloring composition characterized by containing a pigment dispersant (D) having an acidic substituent (excluding the diketopyrrolopyrrole-based pigment dispersant (A)).

[0017] Further, the present invention relates to the color filter coloring composition, wherein the pigment dispersant (D) having an acidic substituent is a sulfonated dye derivative, or a metal salt or amine salt of a sulfonated dye derivative, and the dye skeleton is at least one selected from the group consisting of quinacridone dyes, isoindoline dyes, quinophthalone dyes, and anthraquinone dyes.

[0018] Further, the present invention relates to the color filter coloring composition characterized by further containing a photopolymerizable monomer and / or a photoinitiator.

[0019] Further, the present invention relates to a color filter comprising a filter segment formed from the color filter coloring composition.

[0020] Further, the present invention relates to a liquid crystal display device comprising the color filter.

[0021] The present invention also relates to a solid-state imaging device comprising the color filter.

Advantages of the Invention

[0022] According to the present invention, it is possible to provide a coloring composition for a color filter that can form pixels excellent in storage stability, brightness, contrast ratio, heat resistance, and solvent resistance, a color filter including a filter segment formed using the same, a liquid crystal display device including the color filter, and a solid-state imaging device.

Brief Description of the Drawings

[0023]

Figure 1

Embodiments for Carrying Out the Invention

[0024] Hereinafter, each component constituting the pigment composition for a color filter and the coloring composition for a color filter of the present invention will be described in detail. In the present application, "C.I." means Color Index (C.I.). In addition, when expressed as "(meth)acryloyl", "(meth)acrylic", "(meth)acrylic acid", "(meth)acrylate", and "(meth)acryloyloxy", unless otherwise specified, they represent "acryloyl and / or methacryloyl", "acrylic and / or methacrylic", "acrylic acid and / or methacrylic acid", "acrylate and / or methacrylate", and "acryloyloxy and / or methacryloyloxy", respectively.

[0025] <Diketopyrrolopyrrole-based Pigment Dispersant (A)> The diketopyrrolopyrrole-based pigment dispersant (A) represented by the general formula (1), which is an essential component of the coloring composition for a color filter of the present invention, will be described.

[0026] General formula (1)

Chemical formula

[0027] In general formula (1), the "substituent" in "which may have a substituent" for R1 to R 10 , and R 11 to R 17 is preferably a neutral substituent from the viewpoint of the crystal precipitation inhibiting effect.

[0028] Examples of the unsubstituted alkyl group having 1 to 20 carbon atoms include unsubstituted linear or branched alkyl groups. 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, 1,5-dimethylhexyl group, 1,6-dimethylheptyl group, 2-ethylhexyl group, etc. may be mentioned, but are not limited thereto. From the viewpoint of the crystal precipitation inhibitory effect, those having 3 to 18 carbon atoms are preferable, and those having 4 to 18 carbon atoms are more preferable.

[0029] Examples of the alkyl group having an ether bond and having 1 to 20 carbon atoms include, specifically, 2-methoxyethyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, polyoxyethylene group, etc., but are not limited thereto. From the viewpoint of the crystal precipitation inhibitory effect, those having 3 to 18 carbon atoms are preferable, and those having 4 to 18 carbon atoms are more preferable.

[0030] Examples of the phenyl group which may have the above-mentioned substituent include phenyl groups having substituents such as an alkyl group having 1 to 20 carbon atoms, trifluoromethyl group, halogen atom, nitro group, cyano group, carbamoyl group, sulfamoyl group, and alkoxyl group having 1 to 4 carbon atoms. More specifically, phenyl group, p-methylphenyl group, 4-tert-butylphenyl group, p-nitrophenyl group, p-methoxyphenyl group, p-chlorophenyl group, 2,4-dichlorophenyl group, 3-carbamoylphenyl group, etc. may be mentioned, but are not limited thereto.

[0031] Examples of the aralkyl group which may have the above-mentioned substituent include, specifically, benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2,4-dichlorobenzyl group, etc., but are not limited thereto.

[0032] In the above -SO3M, examples of the metal that forms a sulfonate group and a metal salt include, but are not limited to, sodium, potassium, magnesium, calcium, manganese, iron, cobalt, nickel, copper, zinc, silver, aluminum, etc.

[0033] In the above -SO3M, examples of the amine that forms a sulfonate group and an alkylammonium salt include, but are not limited to, lower amines such as dimethylamine, trimethylamine, diethylamine, triethylamine, hydroxyethylamine, dihydroxyethylamine, 2 - ethylhexylamine, N,N - dimethylaminopropylamine, N,N - diethylaminopropylamine, N,N - dibutylaminopropylamine, etc., long - chain alkylamines having an alkyl group with 2 or more carbon atoms such as laurylamine, oleylamine, palmitylamine, stearylamine, dimethyllaurylamine, etc., and long - chain alkyl quaternary ammonium ions having an alkyl group with 12 or more carbon atoms such as laurylammonium, stearylammonium, lauryltrimethylammonium, dilauryl dimethylammonium, stearyltrimethylammonium, distearyl dimethylammonium, etc.

[0034] Also, as the diketopyrrolopyrrole - based pigment dispersant (A) in the present invention, structures represented by the following general formulas (5) to (11) are preferred from the viewpoints of hue and contrast, and in particular, structures represented by general formulas (5), (6) or (9) are preferred.

[0035] General formula (5):

Chemical formula

[0036] From the viewpoint of the crystal suppression effect, Y is preferably an alkyl group having 3 to 18 carbon atoms, -OR 11 , -SR 12 , and particularly preferably an alkyl group having 4 to 18 carbon atoms, and further preferably a branched alkyl group.

[0037] General formula (6):

Chemical formula

[0038] General formula (7):

Chemical formula

[0039] General formula (8):

Chemical formula

[0040] General formula (9):

Chemical formula

[0041] General formula (10):

Chemical formula

[0042] General formula (11): [Chemical formula] [In general formulas (6) to (11), R 21 ~R 32 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a cyano group, an unsubstituted alkyl group having 1 to 20 carbon atoms, an alkyl group having an ether bond and 1 to 20 carbon atoms, -CF3, -OR 11 , -SR 12 , -N(R 13 )R 14 , or a phenyl group which may have a substituent. R 11 ~R 14 are each independently an unsubstituted alkyl group having 1 to 20 carbon atoms, an alkyl group having an ether bond and 1 to 20 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent. X1 to X 12 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 20 carbon atoms, an alkyl group having an ether bond and 1 to 20 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent. However, X1 and X2 do not become hydrogen atoms at the same time, X3 and X4 do not become hydrogen atoms at the same time, X5 and X6 do not become hydrogen atoms at the same time, X7 and X8 do not become hydrogen atoms at the same time, X9 and X 10 do not become hydrogen atoms at the same time, and X 11 and X 12 do not become hydrogen atoms at the same time. -SO3M represents a sulfo group or a metal salt or alkylammonium salt of a sulfo group.]

[0043] X1 to X 12From the viewpoints of the suppression effects on lightness, contrast, and crystal precipitation, an unsubstituted alkyl group having 3 to 18 carbon atoms, an alkyl group having an ether bond and 3 to 18 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent is preferable, and particularly, an unsubstituted alkyl group having 4 to 18 carbon atoms and an alkyl group having an ether bond and 4 to 18 carbon atoms are preferable. Further, a branched alkyl group is preferable.

[0044] Specific examples of the diketopyrrolopyrrole pigment dispersant (A) that can be used in the present invention are listed below, but are not limited thereto.

[0045] Specific examples of Y and Z in the general formula (5) are shown in Table 1.

[0046] General formula (5):

Chemical formula

[0047]

Table 1

[0048] R in the general formula (6) 21 , R 22 , specific examples of X1 and X2 are shown in Tables 2 and 3.

[0049] General formula (6):

Chemical formula

[0050]

Table 2

[0051]

Table 3

[0052] R in the general formula (7) 23 、R 24 、Specific examples of X3 and X4 are shown in Table 4.

[0053] General formula (7):

Chemical formula

[0054]

Table 4

[0055] R in the general formula (8) 25 、R 26 、Specific examples of X5 and X6 are shown in Table 5.

[0056] General formula (8):

Chemical formula

[0057]

Table 5

[0058] R in the general formula (9) 27 、R 28 、Specific examples of X7, X8 and -SO3M are shown in Table 6.

[0059] General formula (9):

Chemical formula

[0060]

Table 6

[0061] R in the general formula (10) 29 、R 30 、X9、X 10Specific examples of -SO3M are shown in Table 7.

[0062] General formula (10): [Chemical formula]

[0063] [Table 7]

[0064] R in general formula (11) 31 , R 32 , X 11 , X 12 Specific examples of -SO3M are shown in Table 8.

[0065] General formula (11): [Chemical formula]

[0066] [Table 8]

[0067] From the viewpoints of luminance, contrast, and the effect of suppressing crystal precipitation, among the above structures, in particular, (5-2), (5-5), (5-7), (5-9), (6-5), (6-6), (6-7), (6-10), (6-11), (6-12), (6-13), (6-14), (6-27), (6-28), (9-1), etc. are preferable.

[0068] (Method for producing diketopyrrolopyrrole-based pigment dispersant (A)) Several methods for producing the diketopyrrolopyrrole-based pigment dispersant (A) of the present invention can be mentioned, and it is not particularly limited. For example, it can be produced by the following method.

[0069] The diketopyrrolopyrrole-based pigment dispersant represented by the general formula (5) can be produced by the succinic diester synthesis method. That is, 2 moles of the benzonitrile compound of the following general formula (12) are condensed with 1 mole of succinic diester in an inert organic solvent such as tert-amyl alcohol in the presence of an alkali metal or an alkali metal alkoxide at a high temperature of 80 to 110 °C to form an alkali metal salt of the diketopyrrolopyrrole compound. Subsequently, the alkali metal salt of the diketopyrrolopyrrole compound is protonated using water, alcohol, an acid, etc., whereby the diketopyrrolopyrrole-based pigment dispersant of the general formula (5) can be obtained. At this time, the size of the primary particle diameter obtained can be controlled by the temperature, the type, ratio, and amount of water, alcohol, or acid in the protonation. The production method of the diketopyrrolopyrrole-based pigment dispersant represented by the general formula (5) is not limited to this method.

[0070] General formula (12):

Chemical formula

[0071] The diketopyrrolopyrrole-based pigment dispersants represented by General Formulas (6) to (11) are not particularly limited, but the diketopyrrolopyrrole pigments synthesized by the succinic acid diester synthesis method are sulfonated with fuming sulfuric acid, and further chlorinated with a chlorinating agent to form sulfonyl chloride, and then reacted with an arbitrary amine to perform sulfonamidation. This method can be synthesized most simply.

[0072] Diketopyrrolopyrrole can be produced by the succinic acid diester synthesis method. That is, 2 moles of the benzonitrile compound represented by General Formula (13) with respect to 1 mole of succinic acid diester are subjected to a condensation reaction at a high temperature of 80 to 110 °C in an inert organic solvent such as tert-amyl alcohol in the presence of an alkali metal or an alkali metal alkoxide to form an alkali metal salt of the diketopyrrolopyrrole compound. Subsequently, various diketopyrrolopyrrole pigments can be obtained by protonating the alkali metal salt of this diketopyrrolopyrrole compound using water, alcohol, acid, etc.

[0073] General Formula (13):

Chemical Formula

[0074] Also, in the succinic acid diester synthesis method, diketopyrrolopyrroles having a plurality of structures mixed therein can be produced using at least two structurally different benzonitrile compounds.

[0075] Diketopyrrolopyrrole can be sulfonated by reacting with fuming sulfuric acid. In the diketopyrrolopyrrole pigment dispersant of the present invention, the amount of the sulfonic acid group may be 1 equivalent or 2 equivalents, or may be mixed, per molecule of diketopyrrolopyrrole.

[0076] The sulfonated diketopyrrolopyrrole can be easily reacted with a primary amine or a secondary amine by chlorosulfonylation using a chlorinating agent such as thionyl chloride to form a sulfonamide.

[0077] Examples of the amine used in the production of the diketopyrrolopyrrole-based pigment dispersant of the present invention include methylamine, ethylamine, propylamine, butylamine, amylamine, hexylamine, octylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, dimethylamine, N-ethylisopropylamine, N-methylbutylamine, N-methylisobutylamine, N-butylethylamine, N-tert-butylethylamine, diisopropylamine, dipropylamine, N-sec-butylpropylamine, dibutylamine, di-sec-butylamine, diisobutylamine, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, di(2-ethylhexyl)amine, dioctylamine, N-methyloctadecylamine, didecylamine, diallylamine, N-ethyl-1,2-dimethylpropylamine, N-methylhexylamine, dioleylamine, distearylamine, aniline, 2-methylaniline, 3-methylaniline, 4-methylaniline, 4-ethylaniline, 4-propylaniline, 4-butylaniline, 4-amylaniline, 4-decylaniline, 3,4-dimethylaniline, bis(4-tert-butylphenyl)amine, etc., but are not limited thereto.

[0078] <Other pigment dispersants> The colorant composition for a color filter of the present invention can contain a pigment dispersant other than the diketopyrrolopyrrole-based pigment dispersant (A). As the pigment dispersant that can be used in the present invention, known pigment dispersants having an acidic group, a basic group, a neutral group, etc. in an organic dye residue can be used. For example, compounds having an acidic functional group such as a sulfo group, a carboxy group, a phosphate group, and amine salts thereof, compounds having a basic functional group such as a sulfonamide group and a tertiary amino group at the terminal, and compounds having a neutral functional group such as a phenyl group and a phthalimidoalkyl group can be mentioned. Examples of the organic dye include phthalocyanine-based pigments such as diketopyrrolopyrrole-based pigments, copper phthalocyanine, zinc phthalocyanine, aluminum phthalocyanine, halogenated copper phthalocyanine, halogenated zinc phthalocyanine, halogenated aluminum phthalocyanine, and metal-free phthalocyanine; anthraquinone-based pigments such as aminoanthraquinone, diaminoanthraquinone, anthrapyrimidine, flavanthrone, anthraanthrone, indanthrone, pyranthrone, and violanthrone; quinacridone-based pigments; dioxazine-based pigments; perinone-based pigments; perylene-based pigments; thiazine indigo-based pigments; triazine-based pigments; benzimidazolone-based pigments; indole-based pigments such as benzisoindole; isoindoline-based pigments; isoindolinone-based pigments; quinophthalone-based pigments; naphthol-based pigments; threne-based pigments; metal complex-based pigments; azo-based pigments such as azo, disazo, and polyazo, etc.

[0079] More specifically, known pigment dispersants described in Japanese Patent Application Laid-Open No. Sho 61-246261, Japanese Patent Application Laid-Open No. Sho 63-264674, Japanese Patent Application Laid-Open No. Hei 09-272812, Japanese Patent Application Laid-Open No. Hei 10-245501, Japanese Patent Application Laid-Open No. Hei 10-265697, Japanese Patent Application Laid-Open No. Hei 11-199796, Japanese Patent Application Laid-Open No. 2001-172520, Japanese Patent Application Laid-Open No. 2001-220520, Japanese Patent Application Laid-Open No. 2002-201377, Japanese Patent Application Laid-Open No. 2003-165922, Japanese Patent Application Laid-Open No. 2003-168208, Japanese Patent Application Laid-Open No. 2003-171594, Japanese Patent Application Laid-Open No. 2004-217842, Japanese Patent Application Laid-Open No. 2005-213404, Japanese Patent Application Laid-Open No. 2006-291194, Japanese Patent Application Laid-Open No. 2007-079094, Japanese Patent Application Laid-Open No. 2007-226161, Japanese Patent Application Laid-Open No. 2007-314681, Japanese Patent Application Laid-Open No. 2007-314785, Japanese Patent Application Laid-Open No. 2008-31281, Japanese Patent Application Laid-Open No. 2009-57478, WO2009 / 025325 pamphlet, WO2009 / 081930 pamphlet, Japanese Patent Application Laid-Open No. 2011-162662, WO2011 / 052617 pamphlet, Japanese Patent Application Laid-Open No. 2012-172092, Japanese Patent Application Laid-Open No. 2012-208329, Japanese Patent Application Laid-Open No. 2012-226110, WO2012 / 102399 pamphlet, Japanese Patent Application Laid-Open No. 2014-5439, WO2016 / 163351 pamphlet, Japanese Patent Application Laid-Open No. 2017-156397, Japanese Patent No. 5753266, etc. can be mentioned, and these can be used alone or in combination of two or more. Although these documents may describe the pigment dispersant as a derivative, a pigment derivative, a dye derivative, or simply a compound, etc., a compound having a functional group such as an acidic group, a basic group, or a neutral group in the above-described organic dye residue is synonymous with the pigment dispersant.

[0080] (Pigment dispersant (D) having an acidic substituent) As other pigment dispersants, it is preferable from the viewpoint of the interaction with the basic resin type dispersant to contain a pigment dispersant (D) having an acidic substituent (excluding the diketopyrrolopyrrole type pigment dispersant (A)).

[0081] Examples of the pigment dispersant (D) having an acidic substituent include compounds in which an acidic substituent has been introduced into an organic pigment or triazine, which is a colorant skeleton, and examples of such compounds are described in JP-A-63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469, JP-A-2001-335717, JP-A-2003-123114, and the like. Those described in JP-A-8669, JP-A-2004-091497, JP-A-2007-156395, JP-A-2008-094873, JP-A-2008-094986, JP-A-2008-095007, JP-A-2008-195916, Japanese Patent No. 4585781, etc. can be used, and these can be used alone or in combination of two or more types.

[0082] Among these, from the viewpoint of interaction with the basic resin-type dispersant of the present invention, the acidic substituent of the pigment dispersant (D) having an acidic substituent is preferably either a sulfo group, or a metal salt or alkylammonium salt of a sulfo group, and more preferably a sulfo group.

[0083] Metals that make up metal salts include sodium, potassium, calcium, barium, iron, Examples include various metals such as magnesium, aluminum, nickel, cobalt, and strontium. Among these, the use of aluminum salts improves the isolation properties during production and the pigment composition. Not only does it have excellent dispersibility as a powder, but it also has the lowest viscosity, best flow characteristics, and the best viscosity stability over time. A coloring composition is obtained.

[0084] Examples of the amine constituting the alkylammonium salt include lower amines such as dimethylamine, trimethylamine, diethylamine, triethylamine, hydroxyethylamine, dihydroxyethylamine, 2-ethylhexylamine, N,N-dimethylaminopropylamine, N,N-diethylaminopropylamine, and N,N-dibutylaminopropylamine; long-chain alkylamines having an alkyl group with 2 or more carbon atoms such as laurylamine, oleylamine, palmitylamine, stearylamine, and dimethyllaurylamine; and long-chain alkyl quaternary ammonium ions having an alkyl group with 12 or more carbon atoms such as laurylammonium, stearylammonium, lauryltrimethylammonium, dilauryl dimethylammonium, stearyltrimethylammonium, and distearyl dimethylammonium. Among these, when using a salt with a long-chain alkyl quaternary ammonium ion having an alkyl group with 12 or more carbon atoms such as laurylammonium and stearylammonium, a coloring composition with the most excellent dispersion stability and particularly high storage stability can be obtained.

[0085] The number of introduced sulfo groups is preferably 1 or 2 with respect to the pigment skeleton. When it is 3 or more, the affinity for the organic solvent suitable for use in the color filter is lost and the dispersibility decreases.

[0086] When using a pigment dispersant (D) having an acidic substituent (excluding the diketopyrrolopyrrole-based pigment dispersant (A)) in the present invention, it is preferable that the pigment skeleton is selected from the group consisting of quinacridone pigments, isoindoline pigments, quinophthalone pigments, and anthraquinone pigments.

[0087] <Pigment> The coloring composition for a color filter of the present invention can contain, in addition to a red pigment as an essential component, various conventionally known pigments and dyes optionally selected and used in combination as colorants.

[0088] The red pigments that can be used in the present invention 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, 254, 255, 264, 269, 270, 272, 273, 274, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 291, 295, 296, etc., but are not particularly limited thereto.

[0089] When the diketopyrrolopyrrole-based pigment dispersant is used for pigments having the same or similar chemical structures, it can effectively improve non-aggregation, non-crystallinity, fluidity, etc. Also, in terms of hue, it is preferably used for yellow to red pigments, and more preferably used for orange to red pigments.

[0090] In particular, the diketopyrrolopyrrole-based pigment dispersant is preferably used for red pigments typified by diketopyrrolopyrrole-based red pigments, quinacridone-based red pigments, thiazine indigo-based red pigments, anthraquinone-based red pigments, and azo-based red pigments. Among them, the diketopyrrolopyrrole-based red pigment is particularly preferred.

[0091] The orange pigments that can be used in the present invention include, for example, C.I. Pigment Orange 38, 43, or 71, but are not particularly limited thereto.

[0092] Preferably contains at least one diketopyrrolopyrrole pigment selected from the group consisting of C.I. Pigment Red 254, 255, 264, 272, 291, and C.I. Pigment Orange 71, and further preferably contains at least one pigment selected from the group consisting of C.I. Pigment Red 48:1, 122, 166, 168, 176, 177, 179, 202, 209, 242, 268, 269, 295, 296, C.I. Pigment Orange 38, 43, C.I. Pigment Yellow 138, 139, 150, 185, 231, 233, 234.

[0093] Yellow pigments that can be used in the present invention include, for example, 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 or quinophthalone pigments described in Japanese Patent No. 4993026 Gazette, etc., but are not particularly limited thereto.

[0094] The green pigments that can be used in the present invention include, for example, C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, zinc phthalocyanine pigments described in JP-A-2008-19383, JP-A-2007-320986, JP-A-2004-70342, WO 2015 / 118720 pamphlet, etc., aluminum phthalocyanine pigments described in Patent No. 4893859, etc., but are not particularly limited thereto.

[0095] The blue pigments that can be used in the present invention include, for example, 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 JP-A-2004-333817, Patent No. 4893859, etc., but are not particularly limited thereto.

[0096] The purple pigments that can be used in the present invention include, for example, 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 are not particularly limited thereto.

[0097] In the coloring composition for a color filter of the present invention, metal oxides such as titanium dioxide, iron oxide, antimony pentoxide, zinc oxide, and silica, and inorganic pigments such as cadmium sulfide, calcium carbonate, barium carbonate, barium sulfate, clay, talc, lead yellow, and carbon black can also be used.

[0098] <Other colorants> The coloring composition for a color filter of the present invention can contain colorants such as dyes other than the above-mentioned pigments. As the dyes, any of acid dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, mordant dyes, building dyes, sulfur dyes, etc. can be used. Further, derivatives thereof or lake pigments obtained by lake-forming the dyes may be used.

[0099] Furthermore, in the case of acid dyes or direct dyes having acidic groups such as sulfonic acid and carboxylic acid, in the form of an inorganic salt of an acid dye, or a salt-forming compound of an acid dye and a nitrogen-containing compound such as a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, or a primary amine compound, or a resin component having these functional groups is used for salt formation to be used as a salt-forming compound, or sulfonamidation is carried out to be used as a sulfonic acid amide compound, so that it has excellent resistance and can be made into a coloring composition having excellent fastness, which is preferable. Also, a salt-forming compound of an acid dye and a compound having an onium base is also preferable because it has excellent fastness, and more preferably, the compound having an onium base is a resin having a cationic group in the side chain.

[0100] In the case of basic dyes, salt formation can be carried out using an organic acid, perchloric acid, or a metal salt thereof. Among them, the salt-forming compound of a basic dye is preferable because it has excellent resistance and compatibility with pigments. Furthermore, it is more preferable to use a salt-forming compound obtained by salt formation of a basic dye and an anion compound having a counter component that acts as a counterion, such as an organic sulfonic acid, an organic sulfuric acid, a fluorine group-containing phosphorus anion compound, a fluorine group-containing boron anion compound, a cyano group-containing nitrogen anion compound, an anion compound having a conjugate base of an organic acid having a halogenated hydrocarbon group, or an acid dye.

[0101] Also, when the dye skeleton has a polymerizable unsaturated group, it can be made into a dye having excellent resistance, which is preferable.

[0102] Examples of the chemical structure of the dye include a pigment structure derived from a dye selected from azo dyes, disazo dyes, azomethine dyes (such as indoaniline dyes and indophenol dyes), dipyrromethene dyes, quinone dyes (such as benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, and anthrapyridone dyes), carbonium dyes (such as diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, and acridine dyes), quinoneimine dyes (such as oxazine dyes and thiazine dyes), azine dyes, polymethine dyes (such as oxonol dyes, merocyanine dyes, arylidene dyes, styryl dyes, cyanine dyes, squarylium dyes, and croconium dyes), quinophthalone dyes, phthalocyanine dyes, subphthalocyanine dyes, perinone dyes, indigo dyes, thioindigo dyes, quinoline dyes, nitro dyes, nitroso dyes, rhodamine dyes, and metal complex dyes thereof.

[0103] Among these pigment structures, from the viewpoint of color characteristics such as hue, color separation property, and color unevenness, a pigment structure derived from a pigment selected from azo dyes, xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, squarylium dyes, quinophthalone dyes, phthalocyanine dyes, and subphthalocyanine dyes is preferable, and a pigment structure derived from a pigment selected from xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, and phthalocyanine dyes is more preferable. Specific pigment compounds capable of forming the pigment structure are described in "New Edition Dye Handbook" (edited by the Organic Synthetic Chemistry Association; Maruzen, 1970), "Color Index" (The Society of Dyers and colourists), "Pigment Handbook" (edited by Okawara et al.; Kodansha, 1986), etc.

[0104] <Pigment Composition> The colorant composition for a color filter of the present invention may be prepared by mixing a diketopyrrolopyrrole-based pigment dispersant (A) and a pigment to prepare a pigment composition, and then mixing a resinous dispersant (B) having a basic group and a binder resin (C).

[0105] The amount of the diketopyrrolopyrrole-based pigment dispersant contained in the pigment composition is preferably 0.1 to 30 parts by weight, more preferably 1 to 20 parts by weight, per 100 parts by weight of the pigment. When the content of the diketopyrrolopyrrole-based pigment dispersant is less than 0.1 part by weight, it is difficult to obtain the effect of the added diketopyrrolopyrrole-based pigment dispersant. When it is more than 30 parts by weight, the influence on the hue of the diketopyrrolopyrrole-based pigment dispersant is large, and a decrease in lightness may occur.

[0106] Although a sufficient dispersion effect can be obtained by simply mixing the pigment powder and the powder of the diketopyrrolopyrrole pigment dispersant to prepare the pigment composition, methods of mechanically mixing the pigment powder and the powder of the pigment dispersant using a dissolver, a high-speed mixer, a homomixer, a kneader, a roll mill, an attritor, a sand mill, various grinders, etc., a method of adding a solution containing a pigment dispersant to a suspension system of the pigment with water or an organic solvent to deposit the pigment dispersant on the pigment surface, a method of co-dissolving an organic pigment and a pigment dispersant in a solvent having a strong dissolving power such as sulfuric acid and co-precipitating with a poor solvent such as water, etc. may be used to obtain the pigment composition.

[0107] <Finemilling of Pigment> The red pigment and other pigments used in the coloring composition of the present invention are preferably used after being micronized. The micronization method is not particularly limited, and for example, any of wet grinding, dry grinding, and solvent precipitation methods can be used. As exemplified in the present invention, salt milling treatment by a kneader method, which is a type of wet grinding, can be performed to micronize the pigment. The average primary particle diameter determined by TEM (transmission electron microscope) of the pigment is preferably in the range of 5 to 90 nm. When it is smaller than 5 nm, dispersion in an organic solvent becomes difficult, and when it is larger than 90 nm, a sufficient contrast ratio may not be obtained. For these reasons, a more preferable average primary particle diameter is in the range of 10 to 70 nm.

[0108] Salt milling treatment is a process in which a mixture of a pigment, a water-soluble inorganic salt, and a water-soluble organic solvent is mechanically kneaded while heating using a batch-type or continuous kneader such as a kneader, a two-roll mill, a three-roll mill, a ball mill, an attritor, a sand mill, or a planetary mixer, and then the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water. The water-soluble inorganic salt acts as a crushing aid, and the pigment is crushed by utilizing the high hardness of the inorganic salt during salt milling. By optimizing the conditions for salt milling treatment of the pigment, a pigment with a very fine primary particle diameter, a narrow distribution width, and a sharp particle size distribution can be obtained.

[0109] As the water-soluble inorganic salt, sodium chloride, potassium chloride, sodium sulfate, etc. can be used, but from the viewpoint of price, it is preferable to use sodium chloride (table salt). The water-soluble inorganic salt is preferably used in an amount of 50 to 2000 parts by mass, and most preferably 300 to 1000 parts by mass, based on 100 parts by mass of the pigment, from both the treatment efficiency and the production efficiency aspects.

[0110] The water-soluble organic solvent functions to wet the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt used. However, since the temperature rises during salt milling and the solvent is likely to evaporate, from the viewpoint of safety, a high-boiling solvent with 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, etc. are 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, based on 100 parts by mass of the pigment.

[0111] When performing the salt milling treatment, a dye derivative may be used in combination to improve the kneading efficiency. It is very effective for the refinement and size regularization of the pigment. In the refinement of the diketopyrrolopyrrole-based pigment composition used in the present invention, it is preferable to use the dye derivative, but it is not limited thereto. The amount of the dye derivative used is preferably in the range of 0.5 to 30% by mass with respect to 100% by mass of the pigment, so as not to affect the color tone.

[0112] Also, when performing the salt milling treatment, a resin may be added as necessary. The type of the resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, etc. can be used. The resin used is preferably solid at room temperature, water-insoluble, and more preferably partially soluble in the above 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.

[0113] <Specific metal element> In the coloring composition for a color filter of the present invention, small amounts of Li, Na, K, Mg, Ca, Fe, Al, and Cr (hereinafter also referred to as specific metal elements) may be present in addition to the constituent components of the pigment. If a large amount of these specific metal elements is present, the storage stability may be inhibited, the heat resistance may decrease, or the sensitivity may decrease when the photosensitive coloring composition described later is prepared. In addition, when a color filter is produced using a coloring composition in which such specific metal elements are present in a large amount, foreign matter may be generated, and as a result, the brightness is likely to decrease. The total content of the specific metal elements contained in the coloring composition for a color filter of the present invention is preferably 500 mass ppm or less.

[0114] The total amount of the specific metal elements contained in the coloring composition for a color filter of the present invention is more preferably 300 mass ppm or less, and particularly preferably 200 mass ppm or less. The lower limit of the total amount of the specific metal elements is not particularly limited, but is preferably 1 mass ppm or more, and more preferably 5 mass ppm or more. Within the above range, it is possible to obtain a coloring composition that can suppress costs, has excellent storage stability, and can form a color filter with less generation of foreign matter and less decrease in brightness.

[0115] The amount of each specific metal element contained in the coloring composition for a color filter of the present invention is preferably 100 mass ppm or less for each, and more preferably 50 mass ppm or less for each.

[0116] In addition, when metal elements such as Ni, Zn, Cu, Al, Fe, and Co are contained in a part of the pigment structure, these metal elements that do not constitute a part of the pigment structure may be present. It is better that such metal elements are also less, and they can be removed in the same manner as the specific metal elements by the following method. Furthermore, those mixed in by materials (for example, catalysts) used in the manufacturing process of various raw materials of the coloring composition, such as Mn, Cs, Ti, Co, Si, Pd, etc., are preferably at a low concentration.

[0117] As a method for removing metal elements mixed from a device during the production process of a pigment, methods such as those disclosed in JP-A-2010-83997, JP-A-2018-36521, JP-A-7-198928, JP-A-8-333521, JP-A-2009-7432, etc., which are water washing methods, and methods such as removing magnetic foreign substances using a magnet described in JP-A-2011-48736 can be mentioned, and a single method or a plurality of methods can be appropriately used.

[0118] The content of a specific metal element can be measured by inductively coupled plasma optical emission spectrometry (ICP).

[0119] <Resin type dispersant (B) having a basic group> The colored composition for a color filter of the present invention contains a resin type dispersant (B) having a basic group. The resin type dispersant (B) having a basic group has a pigment affinity site containing a basic group that adsorbs to a colorant and a site compatible with the colorant body, and functions to adsorb to the colorant and stabilize the dispersion of the colorant in the carrier.

[0120] Examples of the resin type dispersant (B) having a basic group include a nitrogen atom-containing graft copolymer, a nitrogen atom-containing acrylic block copolymer having a functional group containing a tertiary amino group, a quaternary ammonium base, a nitrogen-containing heterocyclic ring, etc. in the side chain, a random copolymer, and a urethane resin type dispersant.

[0121] In the present invention, from the viewpoint of affinity with the diketopyrrolopyrrole pigment dispersant represented by the general formula (1), the resin type dispersant (B) having a basic group preferably has at least one structural unit selected from the group consisting of a quaternary ammonium base represented by the general formula (2), and primary, secondary or tertiary amino groups represented by the general formulas (3) and (4).

[0122] General formula (2) [In the general formula (2), R [In general formula (2), R201 ~R 203 each independently represents a hydrogen atom or a linear or cyclic hydrocarbon group which may have a substituent, and two or more of R 201 ~R 203 may be bonded to each other to form a cyclic structure. R 204 represents a hydrogen atom or a methyl group, L represents a divalent linking group, and W− represents a counter anion.]

[0123] General formula (3)

Chemical formula

[0124] General formula (4)

Chemical formula

[0125] R in general formula (2) 201 ~R 203 is more preferably an alkyl group having 1 to 4 carbon atoms which may have a substituent, or an aralkyl group having 7 to 16 carbon atoms which may have a substituent, and particularly preferably a methyl group, an ethyl group, a propyl group, a butyl group, or a benzyl group.

[0126] R in general formula (3) 205 and R 206 is more preferably an alkyl group having 1 to 4 carbon atoms which may have a substituent, and particularly preferably a methyl group, an ethyl group, a propyl group, or a butyl group.

[0127] R in general formula (4) 207 Among them, examples of the alkyl group having 1 to 18 carbon atoms include linear, branched, and cyclic alkyl groups. Specifically, examples thereof include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a cyclohexyl group, an n-octyl group, and a hexadecyl group. Examples of the aryl group having 6 to 20 carbon atoms include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. Examples of the aralkyl group having 7 to 12 carbon atoms include a group in which an alkyl group having 1 to 8 carbon atoms is bonded to an aryl group having 6 to 10 carbon atoms. Specifically, examples thereof include a benzyl group, a phenethyl group, an α-methylbenzyl group, and a 2-phenylpropan-2-yl group. Examples of the acyl group include an alkanoyl group having 2 to 8 carbon atoms and an aroyl group. Specifically, examples thereof include an acetyl group and a benzoyl group. Among them, particularly, a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, and an oxy radical are preferable, a hydrogen atom and a methyl group are more preferable, and a methyl group is most preferable.

[0128] In general formulas (2), (3), and (4), examples of the divalent linking group L include a methylene group, an alkylene group having 2 to 10 carbon atoms, an arylene group, -CONH-R 213 -, -COO-R214 -(provided that R 213 and R 214 is a single bond, a methylene group, an alkylene group having 2 to 10 carbon atoms, or an ether group having 2 to 10 carbon atoms (alkyloxyalkyl group), etc., and preferably -COO-R 214 -. Also, in the above formula (2), as the counter anion W - Examples include Cl - , Br - , I - , ClO4 - , BF4 - , CH3COO - , PF6 - etc.

[0129] Specific examples of the ethylenically unsaturated monomer having a quaternary ammonium base, which is a precursor and partial structure of the structural unit represented by the general formula (2), include, for example, alkyl (meth) acrylate quaternary ammonium salts such as (meth) acryloyloxyethyltrimethylammonium chloride, (meth) acryloyloxyethyltriethylammonium chloride, (meth) acryloyloxyethyldimethylbenzylammonium chloride, (meth) acryloyloxymethylmorpholinoammonium chloride, etc., alkyl (meth) acryloylamide quaternary ammonium salts such as (meth) acryloylaminopropyltrimethylammonium chloride, (meth) acryloylaminoethyltriethylammonium chloride, (meth) acryloylaminoethyldimethylbenzylammonium chloride, etc., dimethyldiallylammonium methyl sulfate, trimethylvinylphenylammonium chloride, etc.

[0130] Specific examples of the ethylenically unsaturated monomer having a tertiary amine group, which is a precursor and partial structure of the structural unit represented by the general formula (3), include N,N-dimethylaminoethyl (meth) acrylate, N,N-diethylaminoethyl ( (meth) acrylate, N,N-dimethylaminopropyl (meth) acrylate, N,N- (Meth)acrylates having a tertiary amino group such as diethylaminopropyl (meth)acrylate ; N,N-dimethylaminoethyl (meth)acrylamide, N,N-diethylaminoethyl (meth)acrylamide, N,N-dimethylaminopropyl (meth)acrylamide, and N,N-diethylaminopropyl (meth)acrylamide and other (meth)acrylamides having a tertiary amino group; etc. can be mentioned.

[0131] Specific examples of the ethylenically unsaturated monomer that is a precursor or partial structure of the structural unit represented by the general formula (4) include, for example, compounds represented by the following compounds (4-1) to (4-11).

[0132] [Chemical formula] (4-1) JPEG0007694133000034.jpg2663(4-2) JPEG0007694133000035.jpg2685(4-3) JPEG0007694133000036.jpg2690(4-4) JPEG0007694133000037.jpg2686(4-5) JPEG0007694133000038.jpg2690(4-6) JPEG0007694133000039.jpg2659(4-7) JPEG0007694133000040.jpg2659(4-8)​ JPEG0007694133000041.jpg2663(4-9) JPEG0007694133000042.jpg2666(4-10) JPEG0007694133000043.jpg2660(4-11)

[0133] In compounds (4-1) to (4-11), R 204 represents a hydrogen atom or a methyl group.

[0134] Among these, 2,2,6,6-tetramethylpiperidyl methacrylate (the compound in which R 204 is a methyl group in the above compound (4-1)), 1,2,2,6,6-pentamethylpiperidyl methacrylate (the compound in which R 204 is a methyl group in the above compound (4-2)) are preferred, and particularly 1,2,2,6,6-pentamethylpiperidyl methacrylate is preferred.

[0135] Also, an ethylenically unsaturated monomer containing an amino group other than the structural units represented by general formulas (2) to (4) may be used in combination within a range not impairing the effects of the present invention.

[0136] The amount of the structural units represented by general formulas (2) to (4) in 1 g of the resinous dispersant (B) having a basic group in the present invention is usually preferably 0.1 to 5 mmol, and within this range, lightness and dispersibility can be better balanced.

[0137] The resinous dispersant (B) having a basic group in the present invention preferably has an amine value of 30 to 350 mgKOH / g, although it depends on the types of the structural units represented by general formulas (2) to (4). When the amine value is 30 mgKOH / g or more, the viscosity and viscosity stability of the pigment dispersion are excellent, and when it is 350 mgKOH / g or less, the lightness is excellent.

[0138] In addition, the molecular weight of the resin type dispersant (B) having a basic group in the present invention is preferably in the range of usually 1,000 or more and 100,000 or less in terms of weight average in terms of polystyrene. When the molecular weight of the resin type dispersant (B) having a basic group is less than 1,000, the dispersion stability decreases, and when it exceeds 100,000, the developability tends to decrease.

[0139] In the coloring composition for a color filter of the present invention, in addition to the resin type dispersant (B) having a basic group, other dispersants and various resins described later may be added.

[0140] (Acrylic block copolymer) The resin type dispersant (B) having a basic group of the present invention is more preferably an acrylic block copolymer composed of an A block having a structural unit represented by the general formulas (2) to (4) and a B block not having a structural unit represented by the general formulas (2) to (4). The configurations of the A block and the B block are not particularly limited, but an A-B block, a B-A-B block, or an A-B-A is preferable, and an A-B block and a B-A-B block can be more preferably used.

[0141] The A block is not particularly limited as long as it has any of the structural units represented by the general formulas (2) to (4), but it is preferably a partial structure derived from an ethylenically unsaturated monomer.

[0142] The partial structure containing the structural units represented by the general formulas (2) to (4) may be contained alone or in two or more kinds in one A block. When two or more kinds are contained, they may be contained in any mode of random copolymerization or block copolymerization.

[0143] In addition, the content of the structural units represented by the general formulas (2) to (4) in the A block is preferably 50 to 100% by mass, more preferably 80 to 100% by mass, and particularly preferably 95 to 100% by mass.

[0144] On one hand, the constituent unit contained in the A block that does not contain the constituent units represented by the general formulas (2) to (4), and as for the B block, it is not particularly limited as long as it is a polymer structure obtained by copolymerizing copolymerizable monomers, and can be appropriately selected according to the application. Copolymerizable monomers are shown below.

[0145] For example, linear or branched alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, tertiary butyl (meth)acrylate, isoamyl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cetyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, isomyristyl (meth)acrylate, stearyl (meth)acrylate, and isostearyl (meth)acrylate; cyclic alkyl (meth)acrylates such as cyclohexyl (meth)acrylate, tertiary butyl cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, and isobornyl (meth)acrylate; (meth)acrylates having a heterocyclic ring such as tetrahydrofurfuryl (meth)acrylate and 3-methyl-3-oxetanyl (meth)acrylate; (Meth)acrylates having an aromatic ring such as benzyl (meth)acrylate and phenoxyethyl (meth)acrylate; (Poly)alkylene glycol monoalkyl ether (meth)acrylates such as 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 2-methoxypropyl (meth)acrylate, diethylene glycol monomethyl ether (meth)acrylate, diethylene glycol monoethyl ether (meth)acrylate, diethylene glycol mono-2-ethylhexyl ether (meth)acrylate, dipropylene glycol monomethyl ether (meth)acrylate, triethylene glycol monomethyl ether (meth)acrylate, triethylene glycol monoethyl ether (meth)acrylate, tripropylene glycol monomethyl ether (meth)acrylate, tetraethylene glycol monomethyl ether (meth)acrylate, polyethylene glycol monomethyl ether (meth)acrylate, polypropylene glycol monomethyl ether (meth)acrylate, polyethylene glycol monolauryl ether (meth)acrylate, polyethylene glycol monostearyl ether (meth)acrylate, and octoxypolyethylene glycol - polypropylene glycol (meth)acrylate; (Poly)alkylene glycol (meth)acrylates having an aromatic ring such as phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxytetraethylene glycol (meth)acrylate, phenoxyhexaethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, parachlorophenylphenoxyethyl (meth)acrylate, parachlorophenylphenoxyethylene glycol (meth)acrylate, parachlorophenylphenoxypolyethylene glycol (meth)acrylate, nonylphenoxypolyethylene glycol (meth)acrylate, nonylphenoxypolypropylene glycol (meth)acrylate, and nonylphenoxypoly(ethylene glycol - propylene glycol)(meth)acrylate; (Meth)acrylates having an alkyloxysilyl group such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltrimethoxysilane; Fluoroalkyl (meth)acrylates such as trifluoroethyl (meth)acrylate, octafluoropentyl (meth)acrylate, perfluorooctylethyl (meth)acrylate, and tetrafluoropropyl (meth)acrylate; (Meth)acryloxy-modified polydimethylsiloxanes (silicone macromers); N-substituted (meth)acrylamides such as (meth)acrylamide, dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, diacetone (meth)acrylamide, and acryloylmorpholine; and nitriles such as (meth)acrylonitrile, etc. are mentioned. Also, styrenes such as styrene and α-methylstyrene; vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether; and fatty acid vinyls such as vinyl acetate and vinyl propionate, etc. are mentioned.

[0146] Furthermore, a carboxyl group-containing ethylenically unsaturated monomer can also be used in combination. Examples of the carboxyl group-containing ethylenically unsaturated monomer include (meth)acrylic acid, (meth)acrylic acid dimer, itaconic acid, maleic acid, fumaric acid, crotonic acid, 2-(meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxypropyl phthalate, 2-(meth)acryloyloxyethyl hexahydrophthalate, 2-(meth)acryloyloxypropyl hexahydrophthalate, β-carboxyethyl (meth)acrylate, and ω-carboxypolycaprolactone (meth)acrylate, etc.

[0147] The B block is preferably a partial structure derived from an ethylenically unsaturated monomer. Further, at least an ethylenically unsaturated monomer selected from the group consisting of benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, and hydroxyethyl (meth) acrylate is preferably used.

[0148] (Production of acrylic block copolymer) In the present invention, a preferred acrylic block copolymer as the resin type dispersant (B) having a basic group is prepared, for example, by the living polymerization method shown below. Here, living polymerization is a polymerization method in which side reactions occurring in general radical polymerization are suppressed, and further, the growth of polymerization occurs uniformly, so that it is easy to synthesize block polymers and resins having a uniform molecular weight. Depending on the charging ratio of the polymerization initiator and the vinyl monomer added during polymerization, the molecular weight of the polymer and the ratio of the monomers forming the block copolymer can be freely controlled, and it can be used for the production of block polymers, gradient polymers, star polymers, comb-shaped polymers, and further terminal functional polymers.

[0149] In the present invention, the acrylic block copolymer can be synthesized by a known radical living polymerization method, and the method described in JP-A-2014-219665 or the like can be used. The atom transfer radical polymerization method (ATRP method) and the nitroxide method (NMP method) are preferable not only from the viewpoint of controlling the molecular weight and molecular weight distribution of the polymer, but also in terms of being applicable to a wide range of monomers and being able to adopt a polymerization temperature adaptable to existing equipment. Further, the nitroxide method (NMP method) is more preferable in that it does not use transition metals or the like that can cause coloring or the like.

[0150] [Atom transfer radical polymerization method (ATRP method)] In the atom transfer radical polymerization method, it is carried out using a transition metal complex such as copper, ruthenium, iron, nickel, etc. as a redox polymerization catalyst. Specific examples of the transition metal complex include low-valent halogenated transition metals such as copper (I) chloride and copper (I) bromide.

[0151] An organic ligand is used for the above transition metal complex. The organic ligand is used to enable solubility in a polymerization solvent and reversible changes in a redox polymerization catalyst. Examples of the coordination atom of the transition metal include a nitrogen atom, an oxygen atom, a phosphorus atom, a sulfur atom, etc.

[0152] As the initiator used in the atom radical polymerization method, known ones can be used, but mainly organic halides having a highly reactive carbon-halogen bond, sulfonyl halide compounds, etc. are used. Specifically, examples include ethyl bromoisobutyrate, ethyl bromobutyrate, ethyl chloroisobutyrate, ethyl chlorobutyrate, p-toluenesulfonyl chloride, 1-bromoethylbenzene, chloroethylbenzene, etc. These can be used alone or in combination.

[0153] [Nitroxide method (NMP method)] The living radical polymerization method via nitroxide is carried out using a stable nitroxyl free radical (=N-O·) as a radical capping agent. The stable nitroxyl free radical is not particularly limited, and examples include 2,2,6,6-tetramethyl-1-piperidinyloxy radical (TEMPO), 2,2,6,6-tetraethyl-1-piperidinyloxy radical, 2,2,6,6-tetramethyl-4-oxo-1-piperidinyloxy radical, 2,2,5,5-tetramethyl-1-pyrrolidinyloxy radical, 1,1,3,3-tetramethyl-2-isoindolininyloxy radical, N,N-di-t-butylamine oxy radical, etc. Instead of the nitroxyl free radical, a stable free radical such as galvinoxyl free radical may be used.

[0154] The above radical capping agent is used in combination with a radical polymerization initiator. The combined ratio of the two is not particularly limited, but 0.1 to 10 moles of the radical initiator is appropriate per 1 mole of the radical capping agent.

[0155] The above radical polymerization initiator is appropriately selected according to the weight average molecular weight (Mw) of the resin to be synthesized. When synthesizing a copolymer, it is used in a proportion of 0.0001 to 1 mole, preferably 0.001 to 0.1 mole, per mole of (meth)acryloyl group in the monomers used.

[0156] As the radical polymerization initiator, known ones can be used, and there is no particular limitation as long as it is a compound capable of generating radicals under the polymerization temperature conditions. For example, dialkyl peroxides such as di-t-butyl peroxide, dicumyl peroxide, t-butyl cumyl peroxide, α,α'-bis(t-butylperoxy-m-isopropyl)benzene, 2,5-di(t-butylperoxy)hexyne-3; Peroxy esters such as t-butyl peroxybenzoate, t-butyl peroxyacetate, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane; Ketone peroxides such as cyclohexanone peroxide, 3,3,5-trimethylcyclohexanone peroxide, methylcyclohexanone peroxide; Peroxyketals such as 2,2-bis(4,4-di-t-butylperoxycyclohexyl)propane, 1,1-bis(t-butylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-butylperoxy)cyclohexane, n-butyl-4,4-bis(t-butylperoxy)valerate; Hydroperoxides such as cumene hydroperoxide, diisopropylbenzene hydroperoxide, 2,5-dimethylcyclohexane-2,5-dihydroperoxide; Diacyl peroxides such as benzoyl peroxide, decanoyl peroxide, lauroyl peroxide, 2,4-dichlorobenzoyl peroxide; Organic peroxides such as peroxy dicarbonates such as bis(t-butylcyclohexyl)peroxydicarbonate, or mixtures thereof can be mentioned.

[0157] In addition, an azo compound can also be used as a radical polymerization initiator. For example, 2,2'-azobisbutyronitriles such as 2,2'-azobisisobutyronitrile (AIBN) and 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobisvaleronitriles such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) and 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobispropionitriles such as 2,2'-azobis(2-hydroxymethylpropionitrile), 1,1'-azobis-1-alkanenitriles such as 1,1'-azobis(cyclohexane-1-carbonitrile) can be used.

[0158] Furthermore, as reported in Macromolecules 1995, 28, 2993 instead of using a radical capping agent and the above radical polymerization initiator in combination, an alkoxyamine compound represented by the following compounds (N-1 to 4) may be used as an initiator.

[0159] (N-1) [Chemical formula]

[0160] (N-2) [Chemical formula]

[0161] (N-3) [Chemical formula]

[0162] (N-4) [Chemical formula]

[0163] In the process of producing the acrylic block copolymer, a solvent may or may not be used. Examples of the solvent include ethyl acetate, n-butyl acetate, isobutyl acetate, toluene, xylene, acetone, hexane, methyl ethyl ketone, cyclohexanone, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, or diethylene glycol monobutyl ether acetate, etc., but are not particularly limited thereto. These polymerization solvents may be used as a mixture of two or more kinds.

[0164] The amount of the solvent used is preferably 0 to 300 parts by mass, more preferably 0 to 100 parts by mass, based on 100 parts by mass of the monomers composed of the A block and the B block. The used solvent can be removed by operations such as distillation after the reaction is completed, or can be used as it is as a part of the product of the composition.

[0165] The content of the A block in the acrylic block copolymer solid content is preferably 1 to 99% by mass, more preferably 20 to 50% by mass, and particularly preferably 20 to 30% by mass. When the A block contains 20 to 30% by mass, the remaining 70 to 80% by mass constitutes the B block. Therefore, since the B block has an affinity for the solvent which is the dispersion medium, the pigment can be stably present in the dispersion medium. <Other dispersants> The colored composition for a color filter of the present invention may be used in combination with other dispersants. Specific examples of other dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, polycarboxylic acid alkylamine salts, polysiloxanes, long-chain polyaminoamidophosphates, hydroxyl group-containing polycarboxylic acid esters, modified products thereof, oil-based dispersants such as amides and salts thereof formed by the reaction of poly(lower alkyleneimine) with a polyester having a free carboxyl group, (meth)acrylic acid-styrene copolymers, (meth)acrylic acid-(meth)acrylate copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, water-soluble resins and water-soluble polymer compounds such as polyvinylpyrrolidone, polyester-based, modified polyacrylate-based, ethylene oxide / propylene oxide adduct compounds, phosphate ester-based, etc. These can be used alone or in combination of two or more, but are not necessarily limited thereto.

[0166] <Binder resin (C)> The binder resin (C) used in the colored composition for a color filter of the present invention disperses, dyes, or penetrates a colorant, and examples thereof include thermoplastic resins. When used in the form of an alkali-developable colored resist material, it is preferable to use an alkali-soluble vinyl-based resin copolymerized with an acidic group-containing ethylenically unsaturated monomer. Further, in order to further improve the photosensitivity, an active energy ray-curable resin having an ethylenically unsaturated double bond can also be used.

[0167] In particular, by using an active energy ray-curable resin having an ethylenically unsaturated double bond in the side chain in an alkali-developable colored resist material, when the coating film is formed by exposure with active energy rays, the resin is three-dimensionally crosslinked to fix the colorant, resulting in good heat resistance and suppressing the discoloration of the colorant due to heat (deterioration of spectral characteristics). In addition, it also has the effect of suppressing the aggregation and precipitation of the colorant component in the developing process.

[0168] As the binder resin (C), it is preferable that the resin has a spectral transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength range of 400 to 700 nm in the visible light region.

[0169] For the weight average molecular weight (Mw) of the binder resin (C), in order to preferably disperse the colorant, the range of 2,000 to 80,000 is preferable, and more preferably the range of 3,000 to 40,000. Also, 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.

[0170] When the binder resin (C) is used as a coloring composition for a color filter, the balance of the colorant adsorption group, the carboxy group that functions as an alkali-soluble group during development, the aliphatic group and the aromatic group that function as an affinity group for the colorant carrier and the solvent is important for the dispersibility, permeability, developability, and further durability of the colorant, and it is preferable to use a resin having an acid value of 20 to 300 mgKOH / g. If the acid value is less than 20 mgKOH / g, the solubility in the developer is poor, and it may be difficult to form a fine pattern. If it exceeds 300 mgKOH / g, a fine pattern may not remain.

[0171] Since the binder resin (C) has good film-forming properties and various resistances, it is preferably used in an amount of 20 parts by mass or more with respect to 100 parts by mass of the total mass of the colorant. Since the colorant concentration is high and good color characteristics can be exhibited, it is preferably used in an amount of 1,000 parts by mass or less.

[0172] Examples of the thermoplastic resin used as the binder resin (C) include acrylic resins, butyral resins, styrene-maleic acid copolymers, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polyvinyl acetate, polyurethane resins, polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, and polyimide resins. Among them, it is preferable to use an acrylic resin.

[0173] Examples of the vinyl-based alkali-soluble resin copolymerized with an acidic group-containing ethylenically unsaturated monomer include resins having acidic groups such as carboxy groups and sulfo groups. Specific examples of the alkali-soluble resin include acrylic resins having acidic groups, α-olefin / (anhydrous) maleic acid copolymers, styrene / styrene sulfonic acid copolymers, ethylene / (meth)acrylic acid copolymers, or isobutylene / (anhydrous) maleic acid copolymers. Among them, at least one resin selected from acrylic resins having acidic groups and styrene / styrene sulfonic acid copolymers, particularly acrylic resins having acidic groups, are preferably used because of their high heat resistance and transparency.

[0174] Examples of the active energy ray-curable resin having an ethylenically unsaturated double bond include resins obtained by introducing an unsaturated ethylenically double bond by the following methods (i) or (ii).

[0175] [Method (i)] As method (i), for example, a carboxy group of an unsaturated monobasic acid having an unsaturated ethylenically double bond is added to the side chain epoxy group of a copolymer obtained by copolymerizing an unsaturated ethylenically monomer having an epoxy group and one or more other monomers, and further, a polybasic acid anhydride is reacted with the generated hydroxyl group to introduce an unsaturated ethylenically double bond and a carboxy group.

[0176] Examples of the unsaturated ethylenic monomer having an epoxy group include glycidyl (meth)acrylate, methyl glycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate. These may be used alone or in combination of two or more. From the viewpoint of reactivity with the unsaturated monobasic acid in the next step, glycidyl (meth)acrylate is preferred.

[0177] Examples of the unsaturated monobasic acid include monocarboxylic acids such as (meth)acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, α-haloalkyl, alkoxyl, halogen, nitro, and cyano-substituted products of (meth)acrylic acid. These may be used alone or in combination of two or more.

[0178] Examples of the polybasic acid anhydride include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride, etc. These may be used alone or in combination of two or more. If necessary, such as increasing the number of carboxy groups, tricarboxylic acid anhydrides such as trimellitic anhydride may be used, or tetracarboxylic dianhydrides such as pyromellitic dianhydride may be used to hydrolyze the remaining anhydride groups. Further, when tetrahydrophthalic anhydride or maleic anhydride having an unsaturated ethylenic double bond is used as the polybasic acid anhydride, the number of unsaturated ethylenic double bonds can be further increased.

[0179] As a method similar to method (i), for example, there is a method of introducing an unsaturated ethylenic double bond and a carboxy group by subjecting an unsaturated ethylenic monomer having a carboxy group and one or more other monomers to a copolymerization reaction and then subjecting a part of the side-chain carboxy groups of the obtained copolymer to an addition reaction with an unsaturated ethylenic monomer having an epoxy group.

[0180] [Method (ii)] As method (ii), there is a method in which an unsaturated ethylenic monomer having a hydroxyl group is used, and an isocyanate group of an unsaturated ethylenic monomer having an isocyanate group is reacted with a side-chain hydroxyl group of a copolymer obtained by copolymerizing with a monomer of an unsaturated monobasic acid having another carboxyl group or with another monomer.

[0181] Examples of the unsaturated ethylenic monomer having a hydroxyl group include hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 2- or 3- or 4-hydroxybutyl (meth) acrylate, glycerol (meth) acrylate, or cyclohexanedimethanol mono (meth) acrylate. These may be used alone or in combination of two or more. Further, polyether mono (meth) acrylate obtained by addition polymerization of ethylene oxide, propylene oxide, and / or butylene oxide, etc. to the above hydroxyalkyl (meth) acrylate, or (poly) ester mono (meth) acrylate added with (poly) γ-valerolactone, (poly) ε-caprolactone, and / or (poly) 12-hydroxystearic acid, etc. can also be used. From the viewpoint of suppressing coating film foreign matters, 2-hydroxyethyl (meth) acrylate or glycerol (meth) acrylate is preferable.

[0182] Examples of the unsaturated ethylenic monomer having an isocyanate group include 2-(meth) acryloyloxyethyl isocyanate, or 1,1-bis [(meth) acryloyloxy] ethyl isocyanate, etc. However, it is not limited thereto, and two or more kinds can also be used in combination.

[0183] <Thermosetting compound> The coloring composition of the present invention can contain a thermosetting compound. Examples of the thermosetting compound include, but are not limited to, epoxy compounds and / or resins, benzoguanamine compounds and / or resins, rosin-modified maleic acid compounds and / or resins, rosin-modified fumaric acid compounds and / or resins, melamine compounds and / or resins, urea compounds and / or resins, and phenol compounds and / or resins. When a thermosetting compound is used in the present invention, an epoxy compound is preferable from the viewpoints of heat resistance, solvent resistance, etc. The epoxy compound is not particularly limited as long as it has an epoxy group, and it may be a low-molecular compound or a high-molecular compound such as a resin. In particular, a polyfunctional epoxy compound is preferable because a coating film with a high crosslink density can be obtained.

[0184] The preferable weight-average molecular weight of the epoxy compound is preferably 200 or more and 100,000 or less. A more preferable molecular weight is 300 or more and 10,000 or less, and even more preferably 500 or more and 5000 or less.

[0185] As the epoxy compound, bisphenol A type epoxy compounds, bisphenol F type epoxy compounds, cresol novolak type epoxy compounds, biphenyl type epoxy compounds, alicyclic epoxy compounds, etc. can all be used. Preferably, novolak type epoxy compounds and alicyclic epoxy compounds are used, and particularly preferably alicyclic epoxy compounds. The number of functional groups is preferably 2 or more, and more preferably 3 or more because of excellent thermal crosslinkability.

[0186] Examples of the bifunctional epoxy compound include EPICLON 830, 840, 850, 860, 1050, 2050, 3050, 4050, 7050, HM-091, 101 manufactured by DIC, and Denacol EX-211, 212, 252, 711, 721 manufactured by Nagase ChemteX.

[0187] Examples of polyfunctional epoxy compounds having three or more functional groups include novolak type epoxy compounds and EHPE3150 (manufactured by Daicel Chemical Industries, Ltd.), which is a polymer alicyclic main chain epoxy compound. Specific examples of novolak type epoxy compounds include 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), etc. Also, Techmoa VG3101 (manufactured by Printec Co., Ltd.), which is a trifunctional epoxy compound, and TETRAD-C, TETRAD-X (both manufactured by Mitsubishi Gas Chemical Company, Inc.), which are tetrafunctional epoxy compounds, etc. are also included. Further, Denacol EX-313, 314, 321, 411, 421, 512, 521, 611, 612, 614, 614B, 622, etc. manufactured by Nagase ChemteX Corporation are also included. Also, JER1031S, 1302H60, 604, 630, 630LSD, etc. manufactured by Mitsubishi Chemical Corporation are also included.

[0188] <Organic solvent> The coloring composition of the present invention contains an organic solvent in order to easily disperse and penetrate the colorant sufficiently into the colorant carrier and form a colored film by coating it on a substrate such as a glass substrate so that the dry film thickness becomes 0.2 to 5 μm. The organic solvent is selected in consideration of good coatability of the coloring composition, solubility of each component of the coloring composition, and further safety.

[0189] Examples of the organic solvent include ethyl lactate, benzyl alcohol, 1,3 - butanediol, 1,3 - butylene glycol, 1,3 - butylene glycol diacetate, 1,4 - dioxane, 2 - heptanone, 2 - methyl - 1,3 - propanediol, 3,5,5 - trimethyl - 2 - cyclohexen - 1 - one, 3,3,5 - trimethylcyclohexanone, ethyl 3 - ethoxypropionate, 3 - methyl - 1,3 - butanediol, 3 - methoxy - 3 - methyl - 1 - butanol, 3 - methoxy - 3 - methylbutyl acetate, 3 - methoxybutanol, 3 - methoxybutyl acetate, 4 - heptanone, m - xylene, m - diethylbenzene, N,N - dimethylacetamide, N,N - dimethylformamide, n - butyl alcohol, n - butylbenzene, n - propyl acetate, o - xylene, o - diethylbenzene, p - diethylbenzene, sec - butylbenzene, tert - butylbenzene, γ - butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary 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, diacetone alcohol, triacetin, 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, benzyl alcohol, methyl isobutyl ketone, methyl cyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, dibasic acid ester, and the like can be mentioned. These solvents can be used alone or in combination of two or more at any ratio as required.

[0190] Among them, since the dispersibility, penetrability of the colorant, and the coatability of the colored composition are good, glycol acetates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, alcohols such as benzyl alcohol, diacetone alcohol, 3-methoxybutanol, propylene glycol monomethyl ether, and ketones such as cyclohexanone are preferably used.

[0191] In addition, since the organic solvent can adjust the colored composition to an appropriate viscosity and form a colored film with a desired uniform film thickness, it is preferably used in an amount of 500 to 4000 parts by mass with respect to 100 parts by mass of the colorant.

[0192] <Photopolymerizable monomer> The colored composition of the present invention may contain a photopolymerizable monomer. The photopolymerizable monomer includes monomers or oligomers that are cured by ultraviolet rays, heat, etc. to produce a transparent resin.

[0193] Examples of monomers and oligomers that are cured by ultraviolet rays, heat, etc. to produce a transparent resin include 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, tricyclodecanyl (meth)acrylate, ester acrylate, (meth)acrylic acid ester of methylolated melamine, epoxy (meth)acrylate, urethane acrylate and other various acrylic acid esters and methacrylic acid esters, (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, etc. However, it is not necessarily limited to these. These photopolymerizable compounds can be used alone or in combination of two or more in any ratio as required.

[0194] The blending amount of the photopolymerizable monomer is preferably 5 to 400 parts by mass, more preferably 10 to 300 parts by mass, based on the total mass of the colorant (100 parts by mass) from the viewpoints of photocurability and developability.

[0195] <Photoinitiator> The coloring composition of the present invention may contain a photoinitiator in order to cure the composition by ultraviolet irradiation and form a filter segment by photolithography. In addition, it can be prepared in the form of a solvent-developable or alkali-developable photosensitive coloring composition.

[0196] As the photoinitiator, acetophenone-based compounds such as 4-phenoxydichloroacetophenone, 4-t-butyldichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, or 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one; benzoin-based compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or benzyl dimethyl ketal; benzophenone-based compounds such as benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, or 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone; thioxanthone-based compounds such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, or 2,4-diethylthioxanthone; triazine-based compounds such as 2,4,6-trichloros-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, or 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine;1,2 - octanedione, 1 - [4 - (phenylthio)-, 2 - (O - benzoyloxime)], or oxime ester compounds such as O - (acetyl)-N - (1 - phenyl - 2 - oxo - 2 - (4’ - methoxynaphthyl)ethylidene)hydroxylamine; phosphine compounds such as bis(2,4,6 - trimethylbenzoyl)phenylphosphine oxide, or 2,4,6 - trimethylbenzoyldiphenylphosphine oxide; quinone compounds such as 9,10 - phenanthrenequinone, camphorquinone, ethylanthraquinone; borate compounds; carbazole compounds; imidazole compounds; or titanocene compounds, etc. are used.; These photoinitiators can be used alone or, if necessary, mixed in any ratio of two or more kinds as required.

[0197] The content of the photoinitiator is preferably 2 to 200 parts by mass, more preferably 3 to 150 parts by mass, based on 100 parts by mass of the colorant, from the viewpoints of photocurability and developability.

[0198] <Sensitizer> Furthermore, the color composition of the present invention can contain a sensitizer. Examples of the sensitizer include chalcone derivatives, unsaturated ketones typified by dibenzalacetone, 1,2-diketone derivatives typified by benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, polymethine dyes such as cyanine derivatives, merocyanine derivatives, oxonol derivatives, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphyllin derivatives, annulene derivatives, spiropyran derivatives, spirooxazine derivatives, thiospiropyran derivatives, metal arene complexes, organic ruthenium complexes, or Michler's ketone derivatives, biimidazole derivatives, α-acyloxy esters, acylphosphine oxides, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethylanthraquinone, 4,4'-diethylisophthalophenone, 3,3', or 4,4'-tetra(t-butylperoxycarbonyl)benzophenone, 4,4'-diethylaminobenzophenone, and the like. These sensitizers can be used alone or in combination of two or more in any ratio as required.

[0199] More specifically, examples include, but are not limited to, the sensitizers described in Noboru Okawara et al., "Dye Handbook" (1986, Kodansha), Noboru Okawara et al., "Chemistry of Functional Dyes" (1981, CMC), Chuuzou Ikemori et al., and "Special Functional Materials" (1986, CMC). In addition, other sensitizers that exhibit absorption for light ranging from ultraviolet to near-infrared regions can also be included.

[0200] The content of the sensitizer is preferably 3 to 60 parts by mass, more preferably 5 to 50 parts by mass, based on 100 parts by mass of the photoinitiator contained in the coloring composition, from the viewpoints of photocurability and developability.

[0201] <Thiol compound> The coloring composition of the present invention can contain a thiol compound that functions as a chain transfer agent. As the thiol compound, a polyfunctional thiol compound having two or more thiol groups is preferable. For example, hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene glycol bisthioglycolate, ethylene glycol bisthiopropionate, trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetrakisthioglycolate, pentaerythritol tetrakisthiopropionate, tris(2-hydroxyethyl) isocyanurate trimercaptopropionate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, 2-(N,N-dibutylamino)-4,6-dimercapto-s-triazine, etc. can be mentioned. These polyfunctional thiol compounds can be used alone or in combination of two or more in any ratio as needed.

[0202] The content of the thiol compound is preferably 0.1 to 30% by mass, more preferably 0.1 to 20% by mass, based on the total solid content (100% by mass) of the coloring composition for color filters. When the content of the thiol compound is less than 0.1% by mass, the addition effect of the thiol compound is insufficient, and when it exceeds 30% by mass, the sensitivity may be too high and the resolution may conversely decrease.

[0203] <Antioxidant> The coloring composition of the present invention can contain an antioxidant. The antioxidant can prevent the photoinitiator and thermosetting compound contained in the coloring composition from being oxidized and yellowed by the heat treatment during thermosetting or ITO annealing, and can increase the transmittance of the coating film. Therefore, by including an antioxidant, yellowing due to oxidation during the heating process can be prevented, and a high transmittance of the coating film can be obtained.

[0204] The "antioxidant" in the present invention may be a compound having an ultraviolet absorption function, a radical scavenging function, or a peroxide decomposing function. Specifically, examples of the antioxidant include hindered phenol-based, hindered amine-based, phosphorus-based, sulfur-based, benzotriazole-based, benzophenone-based, hydroxylamine-based, salicylic acid ester-based, and triazine-based compounds, and known ultraviolet absorbers, antioxidants, etc. can be used.

[0205] Among these antioxidants, from the viewpoint of achieving both the transmittance and sensitivity of the coating film, preferred examples include hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, or sulfur-based antioxidants. More preferably, they are hindered phenol-based antioxidants, hindered amine-based antioxidants, or phosphorus-based antioxidants.

[0206] These antioxidants can be used alone or in combination of two or more in any ratio as needed.

[0207] When the content of the antioxidant is 0.1 to 5.0% by mass based on the solid content mass of the coloring composition for color filters (100% by mass), it is more preferable because the lightness and sensitivity are good.

[0208] <amine-based compound> In addition, the coloring composition of the present invention can contain an amine-based compound having the function of reducing dissolved oxygen. Examples of such amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, and N,N-dimethyl-p-toluidine, etc.

[0209] <Leveling agent> In the coloring composition of the present invention, a leveling agent can be added to improve the leveling property of the composition on a transparent substrate. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferred. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning Co., Ltd., BYK-333 manufactured by BYK Chemie GmbH, etc. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310, BYK-370 manufactured by BYK Chemie GmbH, etc. Dimethylsiloxane having a polyether structure in the main chain and 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% by mass based on the total mass of the coloring composition (100% by mass).

[0210] Particularly preferred as a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule. It has a hydrophilic group but low solubility in water, and when added to a coloring composition, it has the characteristic of low surface tension reduction ability. Furthermore, despite the low surface tension reduction ability, those with good wettability to a glass plate are useful, and those that can sufficiently suppress the chargeability at an addition amount where defects in the coating film due to foaming do not appear can be preferably used. As a leveling agent having such preferable characteristics, dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. Examples of the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.

[0211] In addition, the bonding form of the polyalkylene oxide unit to dimethylpolysiloxane may be any of a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type bonded to the end of dimethylpolysiloxane, and a linear block copolymer type in which dimethylpolysiloxane and the polyalkylene oxide unit are alternately and repeatedly bonded. Dimethylpolysiloxane having a polyalkylene oxide unit is commercially available from Toray Dow Corning Co., Ltd., and examples include, but are not limited to, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, and FZ-2207.

[0212] Anionic, cationic, nonionic, or amphoteric surfactants can also be added to the leveling agent as an auxiliary. Two or more surfactants may be mixed and used. Examples of anionic surfactants that are additionally added to the leveling agent include polyoxyethylene alkyl ether sulfates, sodium dodecylbenzenesulfonate, alkali salts of styrene-acrylic acid copolymers, sodium alkylnaphthalenesulfonate, sodium alkyl diphenyl ether disulfonate, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, stearic acid monoethanolamine, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate esters, and the like.

[0213] Examples of the chaotropic surfactants that are additionally added to the leveling agent include alkyl quaternary ammonium salts and their ethylene oxide adducts. Examples of the nonionic surfactants that are additionally added to the leveling agent include polyoxyalkylene-based surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate esters, polyoxyethylene sorbitan monostearate, and polyethylene glycol monolaurate; alkyl betaines such as alkyl dimethylaminoacetate betaine, amphoteric surfactants such as alkyl imidazoline, and also fluorine-based and silicone-based surfactants.

[0214] <Hardening agent, hardening accelerator> In addition, the coloring composition of the present invention may contain a curing agent, a curing accelerator, etc. as necessary to assist the curing of the thermosetting resin. As the curing agent, phenolic resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds, etc. are effective, but it is not particularly limited thereto, and any curing agent may be used as long as it can react with the thermosetting resin. Among these, compounds having two or more phenolic hydroxyl groups in one molecule and amine-based curing agents are preferably mentioned. As the above curing accelerator, for example, amine compounds (e.g., dicyandiamide, benzyldimethylamine, 4-(dimethylamino)-N,N-dimethylbenzylamine, 4-methoxy-N,N-dimethylbenzylamine, 4-methyl-N,N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (e.g., triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (e.g., dimethylamine, etc.), imidazole derivatives, bicyclic amidine compounds and their salts (e.g., imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2-ethyl-4-methylimidazole, etc.), phosphorus compounds (e.g., triphenylphosphine, etc.), guanamine compounds (e.g., melamine, guanamine, acetoguanamine, benzoguanamine, etc.), S-triazine derivatives (e.g., 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, etc.) can be used. These may be used alone or in combination of two or more. The content of the above curing accelerator is preferably 0.01 to 15 parts by mass with respect to 100 parts by mass of the thermosetting resin.

[0215] <Other additive components> The coloring composition of the present invention can contain a storage stabilizer to stabilize the viscosity over time. Further, an adhesion improver such as a silane coupling agent can also be contained to enhance the adhesion to a transparent substrate.

[0216] Examples of the storage stabilizer include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, organic phosphines such as t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine, and phosphites. The storage stabilizer can be used in an amount of 0.1 to 10 parts by mass with respect to 100 parts by mass of the colorant.

[0217] Examples of the adhesion improver include vinylsilanes such as vinyltris(β-methoxyethoxy)silane, vinylethoxysilane, and vinyltrimethoxysilane, (meth)acrylic silanes such as γ-methacryloxypropyltrimethoxysilane, epoxy silanes such as β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, β-(3,4-epoxycyclohexyl)methyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltriethoxysilane, β-(3,4-epoxycyclohexyl)methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, and γ-glycidoxypropyltriethoxysilane, aminosilanes 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, and N-phenyl-γ-aminopropyltriethoxysilane, and thiolsilanes such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane, i.e., silane coupling agents. 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, with respect to 100 parts by mass of the colorant in the coloring composition.

[0218] <Method for Producing Coloring Composition> The coloring composition of the present invention can be produced by finely dispersing a colorant in a colorant carrier such as a resin and / or a solvent, preferably together with a dispersion aid such as a dye derivative or a resin-type dispersant, using various dispersion means such as a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor (colorant dispersion). At this time, two or more colorants or the like may be dispersed in the colorant carrier simultaneously, or those separately dispersed in the colorant carrier may be mixed. When the solubility of the colorant such as a dye is high, specifically, when the solubility in the solvent to be used is high and dissolution is confirmed by stirring and no foreign matter is observed, it is not necessary to produce it by finely dispersing as described above.

[0219] When used as a photosensitive coloring composition (resist material), it can be prepared as a solvent-developable or alkali-developable coloring composition. The solvent-developable or alkali-developable coloring composition can be prepared by mixing the above-mentioned colorant dispersion, a photopolymerizable monomer and / or a photoinitiator, and, if necessary, a solvent, other dispersion aids, and additives. The photoinitiator may be added at the stage of preparing the coloring composition, or may be added later to the prepared coloring composition.

[0220] <Dispersion Aid> When dispersing the colorant in the colorant carrier, a dispersion aid such as a dye derivative (the above-mentioned pigment dispersant), a resin-type dispersant, or a surfactant may be appropriately contained. Since the dispersion aid has a great effect of preventing re-aggregation of the colorant after dispersion, the coloring composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid has good lightness and viscosity stability. The dye derivative and the resin-type dispersant are as described above.

[0221] <Surfactant> Examples of surfactants include anionic surfactants such as sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salts of styrene-acrylic acid copolymers, sodium stearate, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine styrene-acrylic acid copolymer, and polyoxyethylene alkyl ether phosphate ester; nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate, and polyethylene glycol monolaurate; cationic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; and amphoteric surfactants such as alkyl betaines like alkyldimethylaminoacetic acid betaine and alkylimidazolines. These can be used alone or in combination of two or more, but are not necessarily limited to these.

[0222] When adding a surfactant, it is preferably 0.1 to 55 parts by mass, more preferably 0.1 to 45 parts by mass, based on 100 parts by mass of the colorant. When the blending amount of the surfactant is less than 0.1 part by mass, it is difficult to obtain the added effect, and when the content is more than 55 parts by mass, the dispersion may be affected by the excessive dispersant.

[0223] <Removal of Coarse Particles> The colored composition of the present invention is preferably subjected to removal of coarse particles of 5 μm or more, preferably 1 μm or more, more preferably 0.5 μm or more, and mixed dust by means such as centrifugation, filtration through a sintered filter or a membrane filter. Thus, the colored composition preferably contains substantially no particles of 0.5 μm or more. More preferably, it is 0.3 μm or less.

[0224] <Water content in the coloring composition> In the coloring composition of the present invention, the water content is preferably 2% by mass or less with respect to the total amount of the coloring composition.

[0225] When the water content is within the above range, the dispersion stability and sensitivity are excellent even after the coloring composition is stored over time.

[0226] The water content is preferably 1.8% by mass or less, more preferably 1.6% by mass or less with respect to the total amount of the coloring composition. If the water content is sufficiently small within this range, problems with the dispersion stability and sensitivity of the coloring composition are less likely to occur even after storage over time.

[0227] The method for controlling the water content is not particularly limited, and known methods can be used. For example, a method of producing the coloring composition while blowing in a dried inert gas, or a method of adding molecular sieves for dehydration after production can be mentioned. Among them, a method of producing while blowing in a dried inert gas is preferred.

[0228] The water content can be measured by a known method such as the Karl Fischer method.

[0229] <Color filter> Next, the color filter of the present invention will be described. The color filter of the present invention includes a red filter segment, a green filter segment, and a blue filter segment. Further, the color filter may further include a magenta filter segment, a cyan filter segment, and a yellow filter segment. At least one of the red filter segments of the color filter of the present invention is formed from the pigment composition of the present invention.

[0230] <Method for manufacturing a color filter> The color filter can be manufactured by a printing method or a photolithography method. Since the formation of the filter segment by the printing method can be patterned only by repeating the printing and drying of the coloring composition prepared as printing ink, as a manufacturing method of the color filter, it is low-cost and excellent in mass productivity. Furthermore, due to the development of printing technology, it is possible to print a fine pattern having high dimensional accuracy and smoothness. In order to perform printing, it is preferable that the composition be such that the ink does not dry or solidify on the printing plate or on the blanket. Also, the control of the fluidity of the ink on the printing press is important, and the ink viscosity can be adjusted with a dispersant or an extender pigment.

[0231] When forming a filter segment by the photolithography method, the coloring composition prepared as the above solvent-developable or alkali-developable coloring resist material is applied onto a transparent substrate by a coating method such as spray coating, spin coating, slit coating, roll coating, etc. so that the dry film thickness becomes 0.2 to 5 μm. If necessary, the dried film is exposed (irradiated with radiation) through a mask having a predetermined pattern provided in contact or non-contact with this film. Then, after immersing in a solvent or an alkali developer or spraying the developer such as by spraying to remove the uncured portion to form a desired pattern, the same operation can be repeated for other colors to manufacture a color filter. Furthermore, in order to accelerate the polymerization of the coloring resist material, heating can be applied as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.

[0232] At the time of development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as the alkali developer, and organic alkalis such as dimethylbenzylamine or triethanolamine can also be used. Also, an antifoaming agent or a surfactant can be added to the developer. In addition, in order to increase the exposure sensitivity, after applying and drying the colored resist, a water-soluble or alkali-soluble resin, such as polyvinyl alcohol or a water-soluble acrylic resin, etc., is applied and dried to form a film that prevents polymerization inhibition by oxygen, and then exposure can be performed.

[0233] The color filter of the present invention can be manufactured by an electrodeposition method, a transfer method, an inkjet method, etc. in addition to the above method, but the coloring composition of the present invention can be used in any method. The electrodeposition method is a method of manufacturing a color filter by using a transparent conductive film formed on a substrate and electrodepositing each color filter segment on the transparent conductive film by electrophoresis of colloidal particles. The transfer method is a method in which filter segments are formed in advance on the surface of a peelable transfer base sheet and the filter segments are transferred to a desired substrate.

[0234] Before forming each color filter segment on a transparent substrate or a reflective substrate, a black matrix can be formed in advance. As the black matrix, an inorganic film such as chromium or a multilayer film of chromium / chromium oxide, titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but it is not limited thereto. In addition, a thin film transistor (TFT) can be formed in advance on the above transparent substrate or reflective substrate, and then each color filter segment can be formed. Further, an overcoat film, a transparent conductive film, etc. are formed on the color filter of the present invention as necessary.

[0235] <Liquid crystal display device> The liquid crystal display device of the present invention includes the color filter of the present invention. The color filter of the present invention is bonded to the counter substrate using a sealing agent. After injecting liquid crystal from the injection port provided in the seal portion and then sealing the injection port, a polarizing film or a retardation film is bonded to the outside of the substrate as necessary, whereby a color liquid crystal display device is manufactured. This color liquid crystal display device can be used in a liquid crystal display mode for colorization using a color filter such as Twisted Nematic (TN), Super Twisted Nematic (STN), In-Plane Switching (IPS), Vertical Alignment (VA), Optically Compensated Bend (OCB), etc.

[0236] <Solid-state imaging device> The solid-state imaging device of the present invention includes the color filter of the present invention. As the configuration of the solid-state imaging device of the present invention, it is a configuration provided with the color filter for the solid-state imaging device of the present invention, and there is no particular limitation as long as it functions as a solid-state imaging device. For example, the following configurations can be mentioned. On the substrate, it has a plurality of photodiodes constituting the light-receiving area of a solid-state imaging device (CCD sensor, CMOS sensor, organic CMOS sensor, etc.) and transfer electrodes made of polysilicon, etc. It has a light-shielding film made of tungsten, etc., with only the light-receiving part of the photodiode opened on the photodiodes and the transfer electrodes. It has a device protection film made of silicon nitride, etc., formed so as to cover the entire surface of the light-shielding film and the light-receiving part of the photodiode. On the device protection film, it has the color filter for the solid-state imaging device of the present invention. Furthermore, a configuration having condensing means (for example, a microlens, etc. The same applies hereinafter) on the device protection layer and under the color filter (the side closer to the substrate), or a configuration having condensing means on the color filter may also be possible. Note that the organic CMOS sensor is composed of a thin-film panchromatic photosensitive organic photoelectric conversion film as a photoelectric conversion layer and a CMOS signal readout substrate. An organic material plays the role of capturing light and converting it into an electrical signal, and an inorganic material plays the role of extracting the electrical signal to the outside. It has a two-layer hybrid structure, and in principle, the aperture ratio can be 100% for incident light. Since the organic photoelectric conversion film is a structure-free continuous film that can be laid on the CMOS signal readout substrate, it does not require an expensive microfabrication process and is suitable for miniaturization of filter segments. The arrangement of the color filter segments is not particularly limited, and known methods can be used.

[0237] In addition, the color filter of the present invention can also be used in the manufacture of color imaging devices, organic EL display devices, electronic paper, etc. in addition to color liquid crystal display devices.

Examples

[0238] Hereinafter, the present invention will be described by way of examples. In the examples, "parts" and "%" represent "parts by mass" and "mass%", respectively.

[0239] (Number-average molecular weight of the resin-type dispersant having a basic group) The number-average molecular weight (Mn) and mass-average molecular weight (Mw) of the resin-type dispersant having a basic group were measured in terms of polystyrene conversion using HLC-8320GPC (manufactured by Tosoh Corporation) as the apparatus, SUPER-AW3000 as the column, and a solution of 30 mM triethylamine and 10 mM LiBr in N,N-dimethylformamide as the eluent.

[0240] (Amine value of the resin-type dispersant having a basic group) The amine value of the resin-type dispersant having a basic group is a value obtained by converting the measured total amine value (mgKOH / g) into solid content in accordance with the method of ASTM D 2074.

[0241] (Number-average molecular weight of the binder resin) The number average molecular weight (Mn) and mass average molecular weight (Mw) of the binder resin were measured by gel permeation chromatography (GPC) equipped with an RI detector. As the apparatus, HLC-8220GPC (manufactured by Tosoh Corporation) was used. Two separation columns were connected in series, and for both packing materials, "TSK-GEL SUPER HZM-N" was connected in a pair and used. The measurement was carried out at an oven temperature of 40°C, using a THF solution as the eluent, and at a flow rate of 0.35 ml / min. The sample was dissolved in a solvent composed of 1 wt% of the above eluent, and 20 microliters were injected. All molecular weights are values in terms of polystyrene conversion.

[0242] (Acid value of the binder resin) The acid value of the binder resin is the value obtained by converting the measured acid value (mgKOH / g) into solid content basis in accordance with the potentiometric titration method of JIS K 0070.

[0243] Subsequently, the manufacturing methods of the resin solutions, resin-type dispersant solutions, pigment derivatives, and pigment compositions used in the examples and comparative examples will be described.

[0244] (Manufacture of the resin-type dispersant (B) solution having a basic group) (Production example of the resin-type dispersant (B-1) having a basic group: AB type block polymer) Into a reactor equipped with a gas inlet tube, a condenser, a stirring blade, and a thermometer, 60 parts of methyl methacrylate, 20 parts of n-butyl methacrylate, and 13.2 parts of tetramethylethylenediamine as a catalyst were charged. While flowing nitrogen, it was stirred at 50 °C for 1 hour, and the system was purged with nitrogen. Next, 9.3 parts of ethyl bromoisobutyrate as an initiator, 5.6 parts of cuprous chloride as a catalyst, and 133 parts of methoxypropyl acetate were charged. Under a nitrogen stream, the temperature was raised to 110 °C to initiate the polymerization of the first block (B block). After 4 hours of polymerization, the polymerization solution was sampled for solid content measurement, and it was confirmed that the polymerization conversion rate was 98% or more in terms of non-volatile content. Next, 61 parts of methoxypropyl acetate and 20 parts of dimethylaminoethyl methacrylate as the second block (A block) monomer were added to this reactor, and it was stirred while maintaining the temperature at 110 °C in a nitrogen atmosphere to continue the reaction. Two hours after the addition of dimethylaminoethyl methacrylate, the polymerization solution was sampled for solid content measurement, and it was confirmed that the polymerization conversion rate of the second block (A block) was 98% or more in terms of non-volatile content, and the reaction solution was cooled to room temperature to stop the polymerization. As a result of GPC measurement, the Mw of the polymer was 9900, the molecular weight distribution Mw / Mn was 1.2, and the reaction conversion rate was 98.5%. In this way, an acrylic block copolymer (B-1) with an amine value of 71.4 mgKOH / g per solid content was obtained. After cooling to room temperature, about 2 g of the resin solution was sampled and dried by heating at 180 °C for 20 minutes to measure the non-volatile content. Propylene glycol monomethyl ether acetate was added to the previously synthesized block copolymer solution so that the non-volatile content became 50% by mass to prepare a resin-type dispersant (B-1) solution having a basic group.

[0245] (Production Example of Resin-Type Dispersants (B-2 to B-8, B-10) Having Basic Groups: AB-Type Block Polymers) Synthesis was carried out in the same manner as the acrylic block copolymer (B-1) except that the raw materials and charged amounts described in Table 1 were used, and solutions of resin-type dispersants (B-2) to (B-8), (B-10) having basic groups were obtained.

[0246] (Production Example of Resin-Type Dispersant (B-9) Having Basic Groups: BAB-Type Block Polymer) Into a reactor equipped with a gas inlet tube, a condenser, a stirring blade, and a thermometer, 20 parts of methyl methacrylate, 15 parts of n-butyl methacrylate, and 13.2 parts of tetramethylethylenediamine were charged, and the mixture was stirred at 50 °C for 1 hour while flowing nitrogen to replace the system with nitrogen. Next, 9.3 parts of ethyl bromoisobutyrate, 5.6 parts of cuprous chloride, and 133 parts of methoxypropyl acetate were charged, and the temperature was raised to 110 °C under a nitrogen stream to initiate the polymerization of the first block (B block). After 3 hours of polymerization, the polymerization solution was sampled for solid content measurement, and it was confirmed that the polymerization conversion rate was 98% or more in terms of non-volatile content. Next, 30 parts of methoxypropyl acetate and 25 parts of dimethylaminoethyl methacrylate as the second block (A block) monomer were added to this reactor, and the mixture was stirred while maintaining the temperature at 110 °C under a nitrogen atmosphere to continue the reaction. Two hours after the addition of dimethylaminoethyl methacrylate, the polymerization solution was sampled for solid content measurement, and it was confirmed that the polymerization conversion rate of the second block (A block) was 98% or more in terms of non-volatile content. Next, 31 parts of methoxypropyl acetate, 25 parts of methyl methacrylate as the third block (B block), and 15 parts of n-butyl methacrylate were charged into this reactor, and the temperature was raised to 110 °C under a nitrogen stream to continue the polymerization of the first block (B block). Four hours after the addition of the third block (B block) monomer, the polymerization solution was sampled for solid content measurement, and the reaction solution with a confirmed polymerization conversion rate of 98% or more in terms of non-volatile content was cooled to room temperature to stop the polymerization. After cooling to room temperature, about 2 g of the resin solution was sampled and dried by heating at 180 °C for 20 minutes to measure the non-volatile content. Propylene glycol monomethyl ether acetate was added to the previously synthesized acrylic block copolymer solution so that the non-volatile content became 50% by mass to prepare a resin-type dispersant (B-9) solution having basic groups.

[0247] The amine value and weight average molecular weight of each resin-type dispersant having basic groups were as shown in Table 9.

[0248]

Table 9

[0249] (Production Example of Resin-Type Dispersant (B-11) Having a Basic Group: Random Polymer) 70.0 parts of methoxypropyl acetate was charged into a separable four-necked flask equipped with a thermometer, a condenser, a nitrogen gas inlet tube, and a stirrer, and the temperature was raised to 80 °C. After purging the inside of the reaction vessel with nitrogen, a mixture of 20 parts of dimethylaminoethyl methacrylate, 60 parts of methyl methacrylate, 20 parts of n-butyl methacrylate, and 0.4 part of 2,2'-azobisisobutyronitrile was added dropwise from a dropping funnel over 2 hours. After completion of the dropwise addition, the reaction was continued for another 3 hours to obtain a solution of an acrylic resin having a weight average molecular weight (Mw) of 18,000. After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried at 180 °C for 20 minutes to measure the nonvolatile content. Propylene glycol monoethyl ether acetate was added to the previously synthesized resin solution so that the nonvolatile content became 50 mass% to prepare a resin-type dispersant (B-11) solution having a basic group.

[0250] (Preparation of Acidic Resin-Type Dispersant (F-1) Solution) Into a reaction vessel equipped with a gas inlet tube, a temperature controller, a condenser, and a stirrer, 10 parts of methacrylic acid, 100 parts of methyl methacrylate, 70 parts of i-butyl methacrylate, 20 parts of benzyl methacrylate, and 50 parts of propylene glycol monomethyl ether acetate were charged and replaced with nitrogen gas. The inside of the reaction vessel was heated and stirred at 50 °C, and 12 parts of 3-mercapto-1,2-propanediol were added. The temperature was raised to 90 °C, and a solution prepared by adding 0.1 part of 2,2'-azobisisobutyronitrile to 90 parts of propylene glycol monomethyl ether acetate was added while reacting for 7 hours. It was confirmed by solid content measurement that 95% had reacted. 19 parts of pyromellitic dianhydride, 50 parts of propylene glycol monomethyl ether acetate, 50 parts of cyclohexanone, and 0.4 part of 1,8-diazabicyclo-[5.4.0]-7-undecene as a catalyst were added, and the reaction was carried out at 100 °C for 7 hours. It was confirmed by acid value measurement that 98% or more of the acid anhydride had been half-esterified, and the reaction was terminated. Propylene glycol monomethyl ether acetate was added for dilution so that the solid content became 40% by solid content measurement, and a solution of a carboxylic acid-based resin type dispersant (F-1) with an acid value of 77 and a weight average molecular weight of 8,500 was obtained.

[0251] <Production of Binder Resin (C) Solution> (Preparation of Binder Resin Solution 1) Into a separable four-necked flask equipped with a thermometer, a condenser, a nitrogen gas inlet tube, and a stirring device, 100 parts of propylene glycol monomethyl ether acetate was placed. While injecting nitrogen gas into the flask, it was heated to 120°C, and while maintaining the same temperature, 16.2 parts of styrene, 35.5 parts of glycidyl methacrylate, 25.0 parts of dicyclopentanyl methacrylate, 16 parts of methyl methacrylate, and 1.0 part of azobisisobutyronitrile as a catalyst required for the reaction of the precursor at this stage were dropped from a dropping tube over 2.5 hours to carry out a polymerization reaction. Next, the inside of the flask was purged with air, and 17.0 parts of acrylic acid, 0.3 part of tris(dimethylaminomethyl)phenol as a catalyst required for the reaction of the precursor at this stage, and 0.3 part of hydroquinone were added, and the reaction was carried out at 120°C for 5 hours to obtain a resin solution having a weight average molecular weight of about 12,000 (measured by GPC). The acrylic acid added esterifies with the epoxy group terminal of the glycidyl methacrylate structural unit, so no carboxy group is generated in the resin structure. Further, 30.4 parts of tetrahydrophthalic anhydride and 0.5 part of triethylamine as a catalyst required for the reaction of the precursor at this stage were added, and the reaction was carried out at 120°C for 4 hours. One of the two carboxy groups generated by the cleavage of the anhydrous carboxylic acid site of the added tetrahydrophthalic anhydride esterifies with the hydroxyl group in the resin structure, and the other generates a carboxy group terminal. Propylene glycol monomethyl ether acetate was added so that the nonvolatile content became 20% to obtain Resin Binder Resin Solution 1.

[0252] <Production Example of Pigment Dispersant (D) Having Acidic Substituent> (Production of Quinophthalone Compound (D1) Having Sulfonic Group) In the same production method as the quinophthalone compound (QL-c-1) described in the example of JP-A-2015-172732, as a pigment dispersant (D) having acidic substituents, a quinophthalone compound (D1) having a sulfonic group represented by the following formula (14) was obtained.

[0253] Formula (14)

Chemical Formula

[0254] (Production of Quinophthalone Compound (D2) Having Sulfonic Group) 30 parts of C.I. Pigment Yellow 138 (Paliotol Yellow K0960-HD manufactured by BASF), which is a quinophthalone compound, was dissolved in 300 parts of 101% sulfuric acid, and the mixture was stirred at 70 °C for 8 hours to conduct a sulfonation reaction. The end point of the reaction was determined as the point where no change in the spectral spectrum of the sulfuric acid solution was observed. Subsequently, this reaction solution was poured into 3000 parts of ice water, and the precipitate was filtered off, washed with water, and dried at 80 °C to obtain a quinophthalone compound (D2) having a sulfonic group represented by the following formula (15) as a pigment dispersant (D) having an acidic substituent.

[0255] Formula (15) [Chemical formula]

[0256] (Production of Quinophthalone Compound (D3) Having Aluminum Salt of Sulfonic Group) According to the synthesis method described in Japanese Patent Publication No. 4585781, a quinophthalone compound (D3) having an aluminum salt of a sulfonic group represented by the following formula (16) was obtained as a pigment dispersant (D) having an acidic substituent.

[0257] Formula (16) [Chemical formula]

[0258] (Production of Isoindoline Compound (D4) Having Sulfonic Group) 30 parts of C.I. Pigment Yellow 185 (Paliogen Yellow D1155 manufactured by BASF), which is an isoindoline compound, was dissolved in 300 parts of 101% sulfuric acid, and stirred at 70 °C for 8 hours to carry out a sulfonation reaction. The end point of the reaction was determined as the point where no change in the spectral spectrum of the sulfuric acid solution was observed. Next, this reaction solution was poured into 3000 parts of ice water, the precipitate was filtered off, washed with water, and dried at 80 °C to obtain 31 parts of an isoindoline compound (D4) having a sulfo group represented by the following formula (17) as a pigment dispersant (D) having an acidic substituent.

[0259] Formula (17) [Chemical formula]

[0260] <Method for producing diketopyrrolopyrrole-based pigment dispersant (A)> (Production of diketopyrrolopyrrole-based pigment dispersant (A5-1)) Into a stainless steel reaction vessel equipped with a reflux pipe, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium tert-amylate were added under a nitrogen atmosphere, and the mixture was heated to 100 °C with stirring to prepare an alcoholate solution. On the other hand, 88 parts of diisopropyl succinate and 122.5 parts of 4-propylbenzonitrile were added to a glass flask, and the mixture was heated to 90 °C with stirring to dissolve, thereby preparing a solution of these mixtures. This heated solution of the mixture was slowly added dropwise at a constant rate over 2 hours with vigorous stirring into the above-mentioned alcoholate solution heated to 100 °C. After 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-based compound. Further, 600 parts of methanol, 600 parts of water, and 304 parts of acetic acid were added to a reaction vessel equipped with a glass jacket and cooled to -10 °C. While rotating a 8 cm diameter share disk at 4000 rpm using a high-speed stirring disperser, an alkali metal salt solution of the diketopyrrolopyrrole-based compound obtained above and cooled to 75 °C was added little by little to this cooled mixture. At this time, while cooling and adjusting the addition rate of the alkali metal salt of the diketopyrrolopyrrole-based compound at 75 °C so that the temperature of the mixture composed of methanol, acetic acid, and water always remained at a temperature of -5 °C or lower, it was added little by little over about 120 minutes. After the addition of the alkali metal salt, red crystals precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 °C and then filtered to obtain a red paste. This paste was redispersed in 3500 parts of methanol cooled to 0 °C to form a suspension with a methanol concentration of about 90%, and the mixture was stirred at 5 °C for 3 hours to perform particle size adjustment and washing accompanied by crystal transition. Subsequently, it was filtered off with an ultrafilter, and the obtained water paste of the diketopyrrolopyrrole-based compound was dried at 80 °C for 24 hours and pulverized to obtain 129.6 parts of a diketopyrrolopyrrole-based pigment dispersant (A5-1) represented by the following structure.

[0261] Diketopyrrolopyrrole-based pigment dispersant (A5-1):

Chemical formula

[0262] (Production of diketopyrrolopyrrole-based pigment dispersant (A5-2 to A5-12)) Except for changing 122.5 parts of 4-propylbenzonitrile to the nitrile described in Table 10, the production was carried out in the same manner as the production of diketopyrrolopyrrole-based pigment dispersant (A5-1) to obtain diketopyrrolopyrrole-based pigment dispersants (A5-2 to A5-12).

[0263]

Table 10

[0264] (Production of diketopyrrolopyrrole-based pigment dispersant (A6-1)) 30 parts of C.I. Pigment Red 272 (BASF's "Irgazin Flame Red K3800") was charged at room temperature into 300 parts of 102% fuming sulfuric acid. After stirring at room temperature for 3 hours, it was added dropwise to 1500 parts of cold methyl ethyl ketone over 30 minutes. The precipitated disulfonic acid form was filtered, washed with 3000 parts of ice-cold methyl ethyl ketone, and dried at 80 °C to obtain the disulfonic acid form. 10 parts of the disulfonic acid form was charged into 100 parts of N,N-dimethylformamide, and 10 parts of thionyl chloride was slowly added dropwise. The reaction solution was heated to 60 °C and stirred for 6 hours. The reaction solution was poured into 250 parts of ice and 250 parts of water, the precipitate was filtered, washed 3 times with 500 parts of ice water, and a press cake of chlorosulfonyldiketopyrrolopyrrole was obtained. This press cake was charged into 300 parts of N,N-dimethylformamide and 5.6 parts of propylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) and stirred for 3 hours. This mixed solution was poured into 1500 parts of methanol, the precipitate was filtered, washed with methanol and water, and dried at 80 °C. Thus, 10.8 parts of diketopyrrolopyrrole-based pigment dispersant (A6-1) represented by the following structure was obtained.

[0265] Diketopyrrolopyrrole-based pigment dispersant (A6-1):

Chemical formula

[0266] (Synthesis of diketopyrrolopyrrole-based pigment dispersants (A6-2 to A6-31), (A7-1, A7-2), (A8-1, A8-2)) Except for changing C.I. Pigment Red 272 and 5.6 parts of propylamine to the diketopyrrolopyrrole pigments and amines described in Table 11, diketopyrrolopyrrole-based pigment dispersants (A6-2 to A6-31), (A7-1, A7-2), (A8-1, A8-2) were obtained in the same manner as diketopyrrolopyrrole-based pigment dispersant (6-1).

[0267] Also, in the diketopyrrolopyrrole-based pigment dispersants (A6-2 to A6-31), (A7-1, A7-2), the following diketopyrrolopyrrole pigments (1) to (5) were used to obtain pigment dispersants ((A6-2 to A6-31), (A7-1, A7-2),).

[0268] Diketopyrrolopyrrole pigment (1): [Chemical formula]

[0269] Diketopyrrolopyrrole pigment (2): [Chemical formula]

[0270] Diketopyrrolopyrrole pigment (3): [Chemical formula]

[0271] Diketopyrrolopyrrole pigment (4): [Chemical formula]

[0272] Diketopyrrolopyrrole pigment (5): [Chemical formula]

[0273]

Table 11

[0274] (Production of diketopyrrolopyrrole-based pigment dispersant (A12-1)) 30 parts of C.I. Pigment Orange 73 (CINIC's "Cinilex DPP Orange SJ1C") were charged at room temperature into 300 parts of 102% fuming sulfuric acid. After stirring at room temperature for 3 hours, it was added dropwise to 1500 parts of cold methyl ethyl ketone over 30 minutes. The precipitate was filtered, washed with 3000 parts of ice-cold methyl ethyl ketone, and dried at 80 °C to obtain 10.8 parts of diketopyrrolopyrrole-based pigment dispersant (A12-1). As a result of measuring the purity by high performance liquid chromatography, it was confirmed that 2 sulfo groups were introduced per molecule, and the purity was 98%.

[0275] <Production of micronized red pigment> (Preparation of micronized red pigment (PR254-1)) A mixture of 300 parts of diketopyrrolopyrrole red pigment (C.I. Pigment Red 254, BASF's "Irgazin RED L3630"), 1500 parts of sodium chloride, and 150 parts of diethylene glycol was kneaded at 60 °C for 6 hours using a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho). Next, this kneaded product was put into 5 liters of warm water and stirred for 1 hour while heating to 70 °C to make it into a slurry state. After repeating filtration and washing with water to remove sodium chloride and diethylene glycol, it was dried and pulverized to obtain 290 parts of micronized red pigment (PR254-1).

[0276] (Preparation of micronized red pigment (PR291-1)) A mixture of 300 parts of diketopyrrolopyrrole red pigment (C.I. Pigment Red 291, CINIC's "Cinilex DPP MT-CF"), 1500 parts of sodium chloride, and 150 parts of diethylene glycol was kneaded at 60 °C for 6 hours using a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho). Next, this kneaded product was put into 5 liters of warm water and stirred for 1 hour while heating to 70 °C to make it into a slurry state. After repeating filtration and washing with water to remove sodium chloride and diethylene glycol, it was dried and pulverized to obtain 290 parts of micronized red pigment (PR291-1).

[0277] (Preparation of micronized red pigment (PR272-1)) A mixture of 300 parts of diketopyrrolopyrrole red pigment (C.I. Pigment Red 272, BASF's "Irgazin RED K3800"), 1500 parts of sodium chloride, and 150 parts of diethylene glycol was kneaded at 60 °C for 6 hours using a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho). Next, this kneaded product was put into 5 liters of warm water and stirred for 1 hour while heating to 70 °C to make it into a slurry state. After repeating filtration and washing with water to remove sodium chloride and diethylene glycol, it was dried and pulverized to obtain 290 parts of micronized red pigment (PR272-1).

[0278] (Manufacturing method of micronized pigments of other colors) (Manufacturing of micronized green pigment: PG58-1) 200 parts of phthalocyanine green pigment C.I. Pigment Green 58 (DIC's "FASTOGEN GREENA110"), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 80°C for 6 hours. Next, this kneaded material was put into 8000 parts of warm water, stirred for 2 hours while heating to 80°C to form a slurry, and after repeating filtration and washing to remove sodium chloride and diethylene glycol, it was dried at 85°C for a whole day and night to obtain 190 parts of green micronized pigment · PG58-1.

[0279] (Manufacture of micronized yellow pigment: PY138-1) 500 parts of quinophthalone yellow pigment C.I. Pigment Yellow 138 (BASF's "Paliotol Yellow K0960-HD"), 500 parts of sodium chloride, and 250 parts of diethylene glycol were charged into a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 120°C for 8 hours. Next, this kneaded material was put into 5 liters of warm water, stirred for 1 hour while heating to 70°C to form a slurry, and after repeating filtration and washing to remove sodium chloride and diethylene glycol, it was dried at 80°C for a whole day and night to obtain 490 parts of micronized yellow pigment · Y138-1.

[0280] (Manufacture of micronized blue pigment: PB15:6-1) 200 parts of phthalocyanine-based blue pigment C.I. Pigment Blue 15:6 (Toyo Color Co., Ltd.'s "LIONOL BLUE ES", specific surface area 60 m2 / g), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 80°C for 6 hours. Next, this kneaded material was put into 8000 parts of warm water, stirred for 2 hours while heating to 80°C to form a slurry, and after repeating filtration and washing to remove sodium chloride and diethylene glycol, it was dried at 85°C for a whole day and night to obtain 190 parts of micronized blue pigment PB15:6-1.

[0281] (Manufacture of micronized purple pigment: PV23-1) 200 parts of dioxazine violet pigment C.I. Pigment Violet 23 ("LIONOGEN VIOLET RL" manufactured by Toyo Color Co., Ltd.), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 80°C for 6 hours. Next, this kneaded product was put into 8000 parts of warm water, stirred for 2 hours while heating to 80°C to form a slurry, and filtration and washing were repeated to remove sodium chloride and diethylene glycol. Then, it was dried at 85°C for one day and night to obtain 190 parts of micronized violet pigment · PV23-1.

[0282] <Method for producing colored composition> Subsequently, a colored composition was produced and evaluated. [Example 1] (Colored composition (RP-1)) After stirring and mixing the following mixture to make it uniform, it was dispersed for 3 hours with an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads with a diameter of 0.5 mm, and then filtered through a filter with a pore size of 5.0 μm to prepare a colored composition (RP-1) with a non-volatile component of 20% by mass. Micronized red pigment (PR254-1): 10.8 parts Diketopyrrolopyrrole-based pigment dispersant (A5-1): 0.12 part Quinophthalone compound (D-1) having a sulfo group: 1.08 parts Binder resin solution 1: 25.0 parts Propylene glycol monomethyl ether acetate (PGMAc): 57.0 parts Resin type dispersant (B-1) solution having a basic group: 6.0 parts

[0283] [Examples 2 to 77, Comparative Examples 1 to 5] (Colored compositions (RP-2 to 82)) Hereinafter, colored compositions (RP-2 to 82) were prepared in the same manner as the colored composition (RP-1), except that the micronized red pigment, pigment dispersant, and resin type dispersant were changed to the compositions shown in Table 12.

Table 12

[0284] <Method for preparing other coloring compositions> (Preparation of PR177 coloring composition (RP-83)) After stirring and mixing the following mixture to make it uniform, it was dispersed for 3 hours using zirconia beads with a diameter of 0.5 mm in an Eiger mill (Mini Model M-250 MKII manufactured by Eiger Japan Co., Ltd.), and then filtered through a filter with a pore size of 5.0 μm to prepare a coloring composition (RP-83) with a non-volatile component of 20% by mass. C.I. Pigment Red 177 (Sinilex Red SR3C manufactured by Sinic Co., Ltd.) : 12.0 parts Binder resin solution 1: 40.0 parts Propylene glycol monomethyl ether acetate (PGMAc): 48.0 parts

[0285] Coloring compositions (GP-1) to (VP-1) were prepared in the same manner as (RP-83), except that "Sinilex Red SR3C manufactured by Sinic Co., Ltd." was changed to the micronized pigments shown in Table 13.

Table 13

[0286] <Evaluation of coloring compositions> The following evaluations were performed on coloring compositions (RP-1) to (RP-82). The results are shown in Table 14.

[0287] (Evaluation of contrast ratio (CR) of coating film) The light emitted from the backlight unit for the liquid crystal display passes through the polarizing plate and is polarized, passes through the coating film of the coloring composition applied on the glass substrate, and reaches the other polarizing plate. At this time, if the polarization planes of the polarizing plates are parallel, the light passes through the polarizing plate, but if the polarization planes are orthogonal, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the coloring composition, scattering etc. occurs due to the coloring agent particles, and if a shift occurs in a part of the polarization plane, the amount of light transmitted when the polarizing plates are parallel decreases, and when the polarizing plates are orthogonal, a part of the light is transmitted. This transmitted light was measured as the luminance on the polarizing plate, and the ratio of the luminance when the polarizing plates were parallel to the luminance when they were orthogonal was calculated as the contrast ratio. (Contrast ratio) = (Luminance when parallel) / (Luminance when orthogonal) Therefore, when scattering occurs due to the coloring agent in the coating film, the luminance when parallel decreases and the luminance when orthogonal increases, so the contrast ratio becomes low.

[0288] Note that a color luminance meter ("BM-5A" manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate ("NPF-G1220DUN" manufactured by Nitto Denko Corporation) was used as the polarizing plate. At the time of measurement, the measurement was performed through a black mask with a 1 cm square hole opened in the measurement part.

[0289] Each coloring composition was applied onto a 100 mm × 100 mm, 1.1 mm thick glass substrate using a spin coater, then dried at 70 °C for 20 minutes, and then heated at 230 °C for 60 minutes and allowed to cool to produce a coated film substrate. The contrast ratio (CR) of the obtained coated substrate was measured. The produced coated film substrate was adjusted so that the film thickness became 1.5 μm after heat treatment at 230 °C. The contrast ratio was judged according to the following criteria. ◎: 3000 or more: Extremely good ○: 2000 or more and less than 3000: Good △: 1000 or more and less than 2000: Practicable ×: Less than 1000: Defective

[0290] (Storage stability evaluation) The viscosity of the coloring composition was measured at 25°C for the initial viscosity using an E-type viscometer ("ELD-type viscometer" manufactured by Toki Sangyo Co., Ltd.). Separately, 25 g of the pigment dispersion was allowed to stand in a glass container in a sealed state at 40°C for 24 hours, and then the viscosity was measured in the same manner as above to obtain the viscosity over time. The storage stability was evaluated according to the following criteria using the viscosity change rate = (initial viscosity - viscosity over time) / initial viscosity × 100 (%). The evaluation criteria are shown below. ◎(Very good in practical use): When the viscosity change rate is within ±5% and no sediment is formed. ○(Good in practical use): When the viscosity change rate is within ±10% and no sediment is formed. △(Practicable): When the viscosity change rate is ±10% - 20% and no sediment is formed. ×(Not practicable): When the viscosity change rate exceeds ±20%, or when sediment is formed even though the viscosity change rate is within ±20%.

[0291]

Table 14

[0292] As shown in Table 14, the coloring composition of the present invention is excellent in contrast ratio and storage stability. In the coloring compositions of the comparative examples, it was difficult to achieve both high contrast ratio and good storage stability.

[0293] <Manufacture of photosensitive coloring composition> [Example 78] (Red photosensitive coloring composition (RR-1)) After stirring and mixing the following composition mixture uniformly, it was filtered through a filter with a pore size of 1 μm to prepare a red photosensitive coloring composition (RR-1). Coloring composition (RP-1): 25.0 parts Coloring composition (RP-83): 25.0 parts Binder resin solution 1: 7.5 parts Photopolymerizable monomer ("Aronix M-402" manufactured by Toagosei Co., Ltd.): 2.0 parts Photoinitiator (Irgacure OXE-02 manufactured by BASF): 1.2 parts Sensitizer (EAB-F manufactured by Hodogaya Chemical Co., Ltd.): 0.3 part Cyclohexanone: 39.0 parts

[0294] [Examples 79 to 154, Comparative Examples 6 to 10] (Red photosensitive coloring composition (RR-2 to 82)) Red photosensitive coloring compositions (RR-2) to (RR-82) were prepared in the same manner as in Example 78, except that the components shown in Table 15 were changed respectively.

[0295] >[Evaluation of photosensitive coloring composition] The following evaluations were performed on the obtained red photosensitive coloring compositions. The results are shown in Table 15.

[0296] (Evaluation of contrast) Each of the obtained red photosensitive coloring compositions was applied onto a glass substrate of 100 mm × 100 mm and 1.1 mm thick using a spin coater, then dried at 70°C for 20 minutes, and then heat-treated at 230°C for 60 minutes and allowed to cool to prepare a coated film substrate. The contrast ratio (CR) of the obtained coated substrate was measured. The prepared coated film substrate was adjusted so that the film thickness became 1.5 μm after the heat treatment at 230°C. The contrast ratio was judged according to the following criteria. ◎: 3000 or more: Extremely good ○: 2000 or more and less than 3000: Good △: 1000 or more and less than 2000: Practicable ×: Less than 1000: Poor

[0297] (Evaluation of lightness) The obtained red photosensitive coloring composition was applied onto a glass substrate measuring 100 mm × 100 mm and having a thickness of 1.1 mm using a spin coater, and then heated in a clean oven at 80 °C for 15 minutes to remove the solvent, thereby obtaining a coating film. Subsequently, ultraviolet exposure was performed using an ultra-high pressure mercury lamp with an integrated light amount of 100 mJ / cm2, and development was carried out using an alkaline developer at 23 °C to obtain a coated film substrate. Then, after heating in a clean oven at 230 °C for 30 minutes and allowing it to cool, the brightness Y(C) of the obtained coated film substrate was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.). The red coated film substrate was adjusted to a chromaticity of (x = 0.660, y = 0.324) under a C light source after heat treatment at 230 °C. As the alkaline developer, one composed of 1.5% by mass of sodium carbonate, 0.5% by mass of sodium hydrogen carbonate, 8.0% by mass of an anionic surfactant ("Perirex NBL" manufactured by Kao Corporation), and 90% by mass of water was used. The evaluation of brightness was performed according to the following four grades. ◎: 18.5 or more (extremely good) ○: 18.3 or more and less than 18.5 (good) △: 18.1 or more and less than 18.3 (bad) ×: less than 18.1 (extremely bad)

[0298] (Evaluation of crystal precipitates) The photosensitive coloring compositions (RR-1 to RR-82) were applied onto a glass substrate measuring 100 mm × 100 mm and having a thickness of 1.1 mm using a spin coater, and then heated in a clean oven at 70 °C for 15 minutes to remove the solvent, thereby obtaining a dry coating film. At this time, the coating was performed so that the dry coating film had a thickness of 2.5 μm. Subsequently, ultraviolet exposure was performed using an ultra-high pressure mercury lamp with an integrated light amount of 100 mJ / cm2 through a photomask with a 100-μm width (pitch 200 μm) stripe pattern, and development was carried out using an alkaline developer at 23 °C to obtain a striped coated film substrate. Subsequently, heat treatment was performed at 230 °C for 60 minutes, and then further heat treatments were performed at 240 °C for 60 minutes and at 280 °C for 60 minutes. The surface of the coating film on the substrate after heat treatment was observed with an optical microscope, and the presence or absence of crystal precipitation was determined according to the following four-grade criteria. ◎: No crystal precipitation was observed even after heat treatment at 230°C for 60 minutes, further heat treatment at 240°C for 60 minutes, and further heat treatment at 280°C for 60 minutes. ○ ··· No crystal precipitation was observed after heat treatment at 230°C for 60 minutes and further heat treatment at 240°C for 60 minutes, but crystal precipitation was observed after further heat treatment at 280°C for 60 minutes. △ ··· No crystal precipitation was observed after heat treatment at 230°C for 60 minutes, but crystal precipitation was observed after further heat treatment at 240°C for 60 minutes. × ··· Crystal precipitation was observed after heat treatment at 230°C for 60 minutes.

[0299] (Evaluation of solvent resistance) The obtained red photosensitive coloring composition was applied to a glass substrate on which a black matrix had been previously formed by the spin coating method, and then dried in a clean oven at 70°C for 20 minutes. Next, after cooling this substrate to room temperature, ultraviolet light was irradiated through a photomask using an ultra-high pressure mercury lamp. Then, this substrate was spray-developed with a 0.2 mass% aqueous sodium carbonate solution at 23°C for 30 seconds, washed with ion-exchanged water, and dried. Furthermore, heat treatment was performed in a clean oven at 230°C for 30 minutes to form a striped colored pixel layer on the substrate. The fabricated colored pixel layer was adjusted so that the film thickness became 2.0 μm after heat treatment at 230°C. Regarding the obtained striped colored pixels, using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.), [L * (1), a * (1), b * (1)] was measured. Then, it was immersed in N-methyl-2-pyrrolidone (NMP) or methanol (MeOH) for 15 minutes, and after immersion, the chromaticity [L * (2), a * (2), b * (2)] was measured, and the color difference ΔE * ab was determined. The calculation method of the color difference ΔE * ab and the evaluation criteria for solvent resistance are the same as those for the heat resistance evaluation of the coloring composition for color filters.

[0300]

Table 15

[0301] From Table 15, the photosensitive coloring composition containing the coloring composition of the present invention was excellent in solvent resistance and crystal precipitation. The photosensitive coloring composition of the comparative example had poor results in solvent resistance and crystal precipitation. As for the basic resin type dispersant, better results were obtained when using a block copolymer, and the system using a block copolymer containing repeating units derived from dimethylaminoethyl methacrylate and methacryloyloxyethylbenzyldimethylammonium chloride was good.

[0302] <Fabrication of Color Filter> A color filter was fabricated using the red photosensitive coloring composition containing the coloring composition of the present invention. The green photosensitive coloring composition and the blue photosensitive coloring composition used were prepared as follows.

[0303] (Green Photosensitive Coloring Composition (GR-1)) After stirring and mixing the mixture of the following composition until uniform, it was filtered through a filter with a pore size of 1 μm to prepare a green photosensitive coloring composition (GR-1). PG58 · Coloring Composition (GP-1): 35.0 parts PY138 · Coloring Composition (YP-1): 15.0 parts Binder Resin Solution 1: 7.5 parts Photopolymerizable Monomer ("Aronix M-402" manufactured by Toagosei Co., Ltd.): 2.0 parts Photoinitiator ("Irgacure 907" manufactured by BASF): 1.2 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.): 0.3 part Cyclohexanone: 39.0 parts

[0304] (Blue Photosensitive Coloring Composition (BR-1)) After stirring and mixing the mixture of the following composition until uniform, it was filtered through a filter with a pore size of 1 μm to prepare a blue photosensitive coloring composition (BR-1). PB15: 6 · Coloring Composition (BP-1): 45.0 parts PV23 · Coloring Composition (VP-1): 5.0 parts Binder Resin Solution 1: 7.5 parts Photopolymerizable Monomer (Aronix M-402 manufactured by Toagosei Co., Ltd.): 2.0 parts Photoinitiator (Irgacure 907 manufactured by BASF): 1.2 parts Sensitizer (EAB-F manufactured by Hodogaya Chemical Co., Ltd.): 0.3 parts Cyclohexanone: 39.0 parts

[0305] [Example 155] The red photosensitive coloring composition (RR-1) was spin-coated onto a glass substrate on which a black matrix had been previously formed, and then dried in a clean oven at 70°C for 20 minutes. Next, after cooling this substrate to room temperature, ultraviolet light was irradiated through a photomask using an ultra-high pressure mercury lamp. Thereafter, this substrate was spray-developed for 30 seconds with a 0.2 mass% aqueous sodium carbonate solution at 23°C, then washed with ion-exchanged water and dried. Furthermore, heat treatment was performed in a clean oven at 230°C for 30 minutes to form a striped colored pixel layer on the substrate. Next, using the green photosensitive coloring composition (GR-1), a green colored pixel layer was formed in the same manner as the red colored pixel layer. Furthermore, in the same manner, a blue colored pixel layer was formed using the blue photosensitive coloring composition (BR-1) to obtain a color filter (CF-1). The formed film thickness of each colored pixel layer was 2.0 μm.

[0306] Regarding the obtained color filter, the presence or absence of foreign matter on the pixels was confirmed. The measurement method is the same as in the case of evaluating the coloring composition. It was confirmed that there was no foreign matter in the color filter using the coloring composition of the present invention. From the above, the effect of the coloring composition of the present invention was demonstrated.

[0307] <Fabrication of Color Filter for Solid-State Image Sensor> On a 6-inch silicon wafer, a resist solution for planarization film (HL-18s: manufactured by Nippon Steel Chemical Co., Ltd.) was spin-coated, and as a pre-bake, it was heat-treated on a hot plate at 100 °C for 6 minutes. Furthermore, it was treated in an oven at 230 °C for 1 hour to cure the coating film and form a 1.0-μm planarization film, obtaining a wafer with a planarization film.

[0308] A green photosensitive coloring composition (GR-1) was applied onto the silicon wafer with a planarization film using a spin coater, and as a pre-bake, it was heat-treated on a hot plate at 100 °C for 1 minute. The film thickness after pre-baking was adjusted to 0.9 μm.

[0309] Next, using an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.), through a photomask for forming a 1.0-μm square red pixel at a wavelength of 365 nm, the exposure amount was 150 mJ / cm 2 and pattern exposure was performed.

[0310] The coated film after exposure was paddle-developed with an organic alkaline developer for 1 minute. After paddle development, it was rinsed with pure water in a spin shower for 20 seconds, and further washed with pure water for 20 seconds. Then, the water droplets remaining on the wafer were blown off with high-pressure air, and the substrate was naturally dried. Furthermore, it was heat-treated on a hot plate with a surface temperature of 230 °C for 5 minutes to form a square pixel pattern. The film thickness of the green pattern after heat treatment was 0.80 μm.

[0311] Next, using a red photosensitive coloring composition (RR-20), a red coloring pixel layer was formed in the same manner as the green coloring pixel layer. Furthermore, using a blue photosensitive coloring composition (BR-1), a blue coloring pixel layer was formed, obtaining a color filter (CF-2).

[0312] The color filter for a solid-state imaging device thus fabricated was extremely excellent in spectral characteristics. In particular, the hump near 530 nm in the red filter was suppressed, the spectral characteristics were good, and it was excellent in heat resistance. Therefore, the solid-state imaging device using the color filter for a solid-state imaging device was particularly excellent in the reproducibility of skin color.

Explanation of Symbols

[0313] 10 Liquid crystal display device 11 Transparent substrate 12 TFT array 13 Transparent electrode layer 14 Alignment layer 15 Polarizer 21 Transparent substrate 22 Color filter 23 Transparent electrode layer 24 Alignment layer 25 Polarizer 30 Backlight unit 31 White LED light source LC Liquid crystal

Claims

1. A color filter coloring composition comprising a red pigment, a diketopyrrolopyrrole-based pigment dispersant (A), a resinous dispersant (B) having a basic group, and a binder resin (C), wherein the diketopyrrolopyrrole-based pigment dispersant (A) contains a pigment dispersant represented by any of the following general formulas (5) to (11). General formula (5): 【Chemical formula 1】 [In general formula (5), Y and Z are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a cyano group, an unsubstituted alkyl group having 1 to 20 carbon atoms, an alkyl group having an ether bond having 1 to 20 carbon atoms, a phenyl group which may have a substituent, -CF3, -OR11, -SR12, -N(R13)R14, and R11 to R14 are each independently an unsubstituted alkyl group having 1 to 20 carbon atoms, an alkyl group having an ether bond having 1 to 20 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent. However, at least one of Y and Z is an alkyl group having 3 to 18 carbon atoms, -OR11, -SR12, -N(R13)R14.] General formula (6): 【Chemical formula 2】 General formula (7): 【Chemical formula 3】 General formula (8): 【Chemical formula 4】 General formula (9): 【Chemical formula 5】 General formula (10): 【Chemical formula 6】 General formula (11): 【Chemical formula 7】 [In General Formulas (6) to (11), R21 to R32 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a cyano group, an unsubstituted alkyl group having 1 to 20 carbon atoms, an alkyl group having an ether bond and 1 to 20 carbon atoms, -CF3, -OR11, -SR12, -N(R13)R14, or a phenyl group which may have a substituent. R11 to R14 are each independently an unsubstituted alkyl group having 1 to 20 carbon atoms, an alkyl group having an ether bond and 1 to 20 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent. X1 to X12 are each independently a hydrogen atom, an unsubstituted alkyl group having 4 to 18 carbon atoms, or an alkyl group having an ether bond and 4 to 18 carbon atoms. However, X1 and X2 do not simultaneously become hydrogen atoms, X3 and X4 do not simultaneously become hydrogen atoms, X5 and X6 do not simultaneously become hydrogen atoms, X7 and X8 do not simultaneously become hydrogen atoms, X9 and X10 do not simultaneously become hydrogen atoms, and X11 and X12 do not simultaneously become hydrogen atoms. -SO3M represents a sulfo group or a metal salt or alkylammonium salt of a sulfo group.]

2. The colored composition for a color filter according to claim 1, characterized in that the resin-type dispersant (B) having a basic group has at least one structural unit selected from the group consisting of structural units represented by the following general formula (2), general formula (3), and general formula (4). General formula (2) [Chemical Formula 8] [In General Formula (2), R ２０１ to R ２０３ each independently represent a hydrogen atom or a linear or cyclic hydrocarbon group which may have a substituent, and two or more of R ２０１ to R ２０３ may combine with each other to form a cyclic structure. R ２０４ represents a hydrogen atom or a methyl group, L represents a divalent linking group, and W- represents a counter anion.] General formula (3) [Chemical Formula 9] [In General Formula (3), R ２０５ and R ２０６ each independently represent a hydrogen atom or a linear or cyclic hydrocarbon group which may have a substituent, and R ２０５ and R ２０６ may be bonded to each other to form a cyclic structure. R ２０４ represents a hydrogen atom or a methyl group, and L represents a divalent linking group. ] General Formula (4) [Chemical Formula 10] [In General Formula (4), R ２０７ represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, an acyl group, an oxyradical group, or OR ２１２ represents, R ２１２ represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an acyl group, R ２０８ R ２０９ R ２１０ R ２１１ each independently represent a methyl group, an ethyl group, or a phenyl group. R ２０４ represents a hydrogen atom or a methyl group, and L represents a divalent linking group. ]

3. Further, a coloring composition for a color filter according to claim 1 or 2, comprising a pigment dispersant (D) having an acidic substituent (excluding the diketopyrrolopyrrole-based pigment dispersant (A)).

4. The coloring composition for a color filter according to claim 3, wherein the pigment dispersant (D) having an acidic substituent is a sulfonated dye derivative, or a metal salt or alkylammonium salt of a sulfonated dye derivative, and the dye skeleton of the sulfonated dye derivative is at least one selected from the group consisting of quinacridone dyes, isoindoline dyes, quinophthalone dyes, and anthraquinone dyes.

5. Furthermore, a colored composition for a color filter according to any one of claims 1 to 4, which contains a photopolymerizable monomer and / or a photopolymerization initiator.

6. A color filter, comprising a filter segment formed from the colored composition for a color filter according to any one of claims 1 to 5.

7. A liquid crystal display device, comprising the color filter according to claim 6.

8. A solid-state imaging device, comprising the color filter according to claim 6.

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