Compound and Coloring Composition

Abstract

The present invention provides novel compounds and coloring compositions. A compound represented by formula (I). [In formula (I), R 1 ~R 4 each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be substituted with -O- or -CO-. R 5 and R 6 one of them represents a hydroxyl group, and the other represents a hydrogen atom or a hydroxyl group. R 7 and R 8 each independently represents a monovalent hydrocarbon group having 1 to 16 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be substituted with -O- or -CO-.]#imgabs0#

Description

Technical Field

[0001] The present invention relates to novel compounds and coloring compositions. Background Art

[0002] As colorants contained in coloring resin compositions for forming color filters included in liquid crystal display devices, solid-state imaging elements, etc., various dyes are known. Patent Document 1 describes a coloring resin composition containing a squarylium dye.

[0003] Prior Art Documents

[0004] Patent Documents

[0005] Patent Document 1: Japanese Unexamined Patent Application Publication No. 2015 - 86379 Summary of the Invention

[0006] An object of the present invention is to provide a compound having an excellent absorbance retention rate before and after a light resistance test, a coloring composition containing the compound, a colored curable resin composition containing the coloring composition, a color filter formed from these compositions, and a display device including the color filter.

[0007] The present invention provides a compound, a coloring composition, a colored curable resin composition, a color filter, and a display device as shown below.

[0008] 〔1〕A compound represented by formula (I).

[0009]

[0010] [In formula (I),

[0011] R 1 ~R 4 each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be substituted with -O- or -CO-.

[0012] R 5 and R 6 one of them represents a hydroxyl group, and the other represents a hydrogen atom or a hydroxyl group.

[0013] R 7 and R 8 each independently represents a monovalent hydrocarbon group having 1 to 16 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be substituted with -O- or -CO-.]

[0014] 〔2〕A coloring composition containing a colorant containing the compound described in the above 〔1〕 and a resin.

[0015] [3] A colored curable resin composition comprising the colored composition described in [2] above, a polymerizable compound, and a polymerization initiator.

[0016] [4] A color filter formed from the colored composition described in [2] above or the colored curable resin composition described in [3] above.

[0017] [5] A display device comprising the color filter described in [4] above.

[0018] The colored composition containing the compound of the present invention has an excellent absorbance retention rate before and after the light resistance test. Description of the Drawings

[0019] Figure 1 (a) and (b) in are cross-sectional schematic views showing an example of an optical filter.

[0020] Figure 2 (a) in is a cross-sectional schematic view showing an example of an organic EL display device using an optical filter, and (b) is a cross-sectional schematic view showing an example of a liquid crystal display device using an optical filter.

[0021] Symbol Explanation

[0022] 1, 2 Image display element, 10 Optical filter, 11 Adhesive layer for image display element, 12 Phase difference film, 13 Adhesive layer, 14 First protective film, 15 Polarizing film, 16 Second protective film, 20 Optical filter, 21 Adhesive layer for image display element, 24 First protective film, 25 Polarizing film, 26 Second protective film. Detailed Description

[0023] (Compound represented by formula (I))

[0024] The present invention relates to a compound represented by the following formula (I) (hereinafter, sometimes referred to as "compound (I)").

[0025]

[0026] [In formula (I),

[0027] R 1 ~R 4 Each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be substituted with -O- or -CO-.

[0028] R 5 and R 6 One of them represents a hydroxyl group, and the other represents a hydrogen atom or a hydroxyl group.

[0029] R7 and R 8 each independently represents a monovalent hydrocarbon group having 1 to 16 carbon atoms which may have substituents, and the —CH2— contained in the hydrocarbon group may be substituted with —O— or —CO—.

[0030] When the compound (I) is used in the coloring composition described later, for example, the absorbance retention rate is excellent before and after the light resistance test. The absorbance mentioned here can be, for example, the absorbance at the maximum absorption wavelength. When the compound (I) is used as a coloring composition, for example, the heat resistance is also excellent.

[0031] In the compound (I), in addition to the description represented by the formula (I), there are, for example, tautomeric forms of the resonance structure represented by the following formula. The compound (I) includes all the tautomers.

[0032]

[0033] The hydrocarbon group in the formula (I) refers to a group composed of carbon atoms and hydrogen atoms, and the number of carbon atoms in the hydrocarbon group includes the number of carbon atoms in the substituents.

[0034] The number of carbon atoms in the group after the —CH2— contained in the hydrocarbon group is substituted with —O— or —CO— refers to the number of carbon atoms before being substituted with —O— or —CO—.

[0035] In the formula (I), as R 1 ~R 4 the monovalent hydrocarbon group having 1 to 6 carbon atoms, examples thereof include a monovalent aliphatic hydrocarbon group or a monovalent aromatic hydrocarbon group.

[0036] R 1 ~R 4 The monovalent aliphatic hydrocarbon group in may be a monovalent aliphatic saturated hydrocarbon group or a monovalent aliphatic unsaturated hydrocarbon group. The monovalent aliphatic hydrocarbon group may be a linear, branched chain hydrocarbon group or an alicyclic hydrocarbon group.

[0037] As R 1 ~R 4 the monovalent aliphatic saturated hydrocarbon group, examples thereof include linear alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl and hexyl; branched alkyl groups having 3 to 6 carbon atoms such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl and neopentyl; alicyclic saturated hydrocarbon groups having 3 to 6 carbon atoms such as cyclopropyl, cyclopentyl and cyclohexyl, etc.

[0038] As R 1 ~R 4Examples of the monovalent aliphatic unsaturated hydrocarbon group include linear alkenyl groups having 2 to 6 carbon atoms such as vinyl, propenyl, butenyl, pentenyl, and hexenyl; branched alkenyl groups having 4 to 6 carbon atoms such as sec-buteneyl and isobutenyl; linear alkynyl groups having 3 to 6 carbon atoms such as propynyl, n-butynyl, n-pentynyl, and n-hexynyl; branched alkynyl groups having 4 to 6 carbon atoms such as sec-butynyl and isobutynyl; cycloalkenyl groups having 3 to 6 carbon atoms such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl; and cycloalkynyl groups having 4 to 6 carbon atoms such as cyclobutynyl, cyclopentynyl, and cyclohexynyl, etc.

[0039] R 1 ~R 4 When the monovalent aliphatic hydrocarbon group in ~ contains a cyclic structure, the number of carbon atoms constituting the cyclic structure is preferably 3 to 6, more preferably 5 or 6.

[0040] As R 1 ~R 4 Examples of the monovalent aromatic hydrocarbon group include phenyl.

[0041] In formula (I), examples of the substituents that the hydrocarbon group represented by R 1 ~R 4 may have include halogen atoms, hydroxyl groups, amino groups, nitro groups, aminosulfonyl groups, sulfo groups, etc.

[0042] Examples of the halogen atom include fluorine atom, chlorine atom, bromine atom, or iodine atom.

[0043] As R 1 ~R 4 Examples of the substituents that the hydrocarbon group may have preferably include halogen atoms.

[0044] In formula (I), the -CH2- contained in the hydrocarbon group represented by R 1 ~R 4 may be substituted with -O- or -CO-. Examples of such groups include -C(=O)CH3 and -C(=O)-OCH2CH3.

[0045] R 1 ~R 4 Each independently is preferably a hydrogen atom or an alkyl group, more preferably both are hydrogen atoms.

[0046] In formula (I), as long as one of R 5 and R 6 is a hydroxyl group and the other is a hydrogen atom or a hydroxyl group. R 5 and R 6 may also both be hydroxyl groups, preferably one is a hydroxyl group and the other is a hydrogen atom.

[0047] In formula (I), as R 7 and R 8The monovalent hydrocarbon group having 1 to 16 carbon atoms may be a monovalent aliphatic hydrocarbon group or a monovalent aromatic hydrocarbon group.

[0048] R 7 and R 8 The monovalent aliphatic hydrocarbon group in may be a monovalent aliphatic saturated hydrocarbon group or a monovalent aliphatic unsaturated hydrocarbon group. The monovalent aliphatic hydrocarbon group may be a linear or branched chain hydrocarbon group or an alicyclic hydrocarbon group.

[0049] As R 7 and R 8 Examples of the monovalent aliphatic saturated hydrocarbon group in R and R include linear alkyl groups having 1 to 16 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; branched alkyl groups having 3 to 16 carbon atoms such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl; cycloalkyl groups having 3 to 16 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclopentenyl; alkylcycloalkyl groups having 4 to 16 carbon atoms such as propylcyclohexyl and octylcyclohexyl; and cycloalkylalkyl groups having 4 to 16 carbon atoms such as cyclohexylbutyl and cyclohexyl octyl.

[0050] As R 7 and R 8 Examples of the monovalent aliphatic unsaturated hydrocarbon group in R and R include linear alkenyl groups having 2 to 16 carbon atoms such as vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, and decenyl; branched alkenyl groups such as sec-butenyl and isobutenyl; linear alkynyl groups having 4 to 16 carbon atoms such as propynyl, n-butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n-octynyl, n-nonynyl, and n-decynyl; branched alkynyl groups having 4 to 16 carbon atoms such as sec-butynyl and isobutynyl; cycloalkenyl groups having 3 to 16 carbon atoms such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl; alkenylcycloalkyl groups having 5 to 16 carbon atoms such as propenylcyclohexyl and 1-decenylhexyl; and cycloalkynyl groups having 4 to 16 carbon atoms such as cyclobutynyl, cyclopentynyl, and cyclohexynyl.

[0051] R 7 and R 8 When the monovalent aliphatic hydrocarbon group in R and R contains a cyclic structure, the number of carbon atoms constituting the cyclic structure is preferably 3 to 8, more preferably 4 to 6.

[0052] As R 7 and R 8 Examples of the monovalent aromatic hydrocarbon group in R and R include aryl groups having 6 to 16 carbon atoms such as phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, propylphenyl, butylphenyl, hexylphenyl, 2-ethylhexylphenyl, naphthyl, biphenyl, anthryl, and phenanthryl; and aralkyl groups having 7 to 16 carbon atoms such as benzyl, phenethyl, phenylpropyl, and phenylbutyl.

[0053] Constitute R 7 and R 8 In the monovalent aromatic hydrocarbon group, the number of carbon atoms of the aromatic ring is preferably 6 to 8, more preferably 4 to 6, and still more preferably 6.

[0054] As the aromatic hydrocarbon group having 6 carbon atoms in the aromatic ring, 4-alkylphenyl, 2,4-alkylphenyl, 2,4,6-alkylphenyl, etc. can be mentioned.

[0055] In formula (I), as R 7 and R 8 The substituents that the hydrocarbon group in can have include those exemplified in R 1 ~R 4 The substituents exemplified.

[0056] As R 7 and R 8 The substituents that the hydrocarbon group in can have are preferably halogen atoms.

[0057] In formula (I), -CH2- contained in the hydrocarbon group of R 7 and R 8 Can be substituted with -O- or -CO-. As such groups, for example, -C(=O)CH3, -C(=O)-OCH2CH3 can be mentioned.

[0058] R 7 and R 8 Are preferably each a chain hydrocarbon group, or one is a chain hydrocarbon group and the other is an aromatic hydrocarbon group. When R 7 and R 8 Are each a chain hydrocarbon group, R 7 and R 8 Can be the same as or different from each other. As the chain hydrocarbon group, an alkyl group is preferred, and as the aromatic hydrocarbon group, an aryl group is preferred.

[0059] As compound (I), for example, the compounds represented by the following formula can be mentioned.

[0060]

[0061] (Manufacturing method (1) of compound (I))

[0062] The compound (I) of the present invention can be produced, for example, by reacting a compound represented by the following formula (IV-1) (hereinafter, sometimes referred to as "compound (IV-1)"), a compound represented by the following formula (IV-2) (hereinafter, sometimes referred to as "compound (IV-2)") with squaric acid (3,4-dihydroxy-3-cyclobutene-1,2-dione) represented by the following formula (IV-3).

[0063]

[0064] [In formulas (IV-1) and (IV-2), R 1 ~R 8 represents the same meaning as described above.]

[0065] As the compound (IV-1), for example, the compounds represented by the following formulas can be cited.

[0066]

[0067] As the compound (IV-2), for example, the compounds represented by the following formulas can be cited.

[0068]

[0069] In the process of manufacturing the compound (I), from the aspect of yield, it is preferably to adopt the method of dehydrative condensation of the compound (IV-1), the compound (IV-2) and squaric acid in an organic solvent.

[0070] As the organic solvent, aromatic hydrocarbon solvents such as toluene and xylene can be cited; hydrocarbon solvents such as hexane, cyclohexane and decalin, ether solvents such as tetrahydrofuran, 1,4-d ane and dimethoxyethane; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; alcohol solvents such as methanol, ethanol, isopropanol and butanol; nitrohydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; amide solvents such as N,N-dimethylformamide and 1-methyl-2-pyrrolidone, etc., and these can also be used in combination. Among them, a mixed solvent of butanol and toluene is preferred. The usage amount of the organic solvent is preferably 10 parts by mass to 200 parts by mass, more preferably 20 parts by mass to 160 parts by mass, relative to 1 part by mass of squaric acid.

[0071] The usage amount of squaric acid in the process of manufacturing the compound (I) is preferably 0.45 mol to 0.6 mol, more preferably 0.47 mol to 0.55 mol, relative to 1 mol in total of the compound (IV-1) and the compound (IV-2).

[0072] The reaction temperature is preferably 30°C to 180°C, more preferably 80°C to 140°C. The reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.

[0073] The method for obtaining the compound (I) as the target compound from the reaction mixture is not particularly limited, and various known methods can be adopted. For example, the method of filtering the precipitated crystals after cooling can be cited. The filtered crystals are preferably washed with water or the like and then dried. In addition, further purification can also be carried out by known methods such as recrystallization and column chromatography as needed.

[0074] Compound (IV-1) can be prepared by reacting the compound represented by the following formula (IV-4) with the compound represented by the following formula (IV-5) to obtain the compound represented by the following formula (IV-6), and then reacting the compound represented by formula (IV-6) with the compound represented by the following formula (IV-7).

[0075]

[0076] [In formula (IV-4), formula (IV-5), formula (IV-6), and formula (IV-7), R 3 ~R 8 represents the same meaning as described above.]

[0077] As a method for preparing the compound represented by formula (IV-6) from the compound represented by the following formula (IV-4) and the compound represented by the following formula (IV-5), various known methods can be cited. For example, the method described in Eur. J. Org. Chem. 2012, 3105 - 3111 can be used.

[0078] As a method for preparing the compound represented by compound (IV-1) from the compound represented by formula (IV-6) and the compound represented by formula (IV-7), various known methods can be cited. For example, the method described in J. Polymer Sciene Science Part A: Polymer Chemistry 2012, 50, 3788 - 3796 can be used.

[0079] (Method for preparing compound (I) (2))

[0080] The compound (I) of the present invention can be prepared by reacting the above-mentioned compound (IV-2) with the reaction product obtained by reacting squaric acid represented by the above formula (IV-3) with the above-mentioned compound (IV-1) (hereinafter, sometimes referred to as "reaction product (IV-9a)").

[0081] As compound (IV-1) and compound (IV-2), the above-mentioned compounds can be cited.

[0082] The reaction of squaric acid represented by formula (IV-3) with compound (IV-1) and the reaction of reaction product (IV-9a) with compound (IV-2) are preferably carried out in an organic solvent.

[0083] As the organic solvent, the above-mentioned organic solvents can be cited.

[0084] In the process for producing compound (I), the amount of compound (IV-1) used is preferably 0.7 mol to 3 mol, more preferably 1 mol to 2 mol, relative to 1 mol of squaric acid represented by formula (IV-3).

[0085] In the process for producing compound (I), the amount of compound (IV-2) used is preferably 0.7 mol to 3 mol, more preferably 1 mol to 2 mol, relative to 1 mol of the reaction product (IV-9a).

[0086] The reaction temperature is preferably 30°C to 180°C, more preferably 80°C to 140°C. The reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.

[0087] The method for obtaining compound (I) as the target compound from the reaction mixture is not particularly limited, and various known methods can be employed, such as the above-mentioned methods.

[0088] (Method for producing compound (I) (3))

[0089] Compound (I) of the present invention can be produced by reacting the above-mentioned compound (IV-1) with the reaction product (hereinafter sometimes referred to as "reaction product (IV-9b)") obtained by reacting squaric acid represented by the above formula (IV-3) with the above-mentioned compound (IV-2).

[0090] Examples of compound (IV-1) and compound (IV-2) include the above-mentioned compounds.

[0091] In the process for producing compound (I), the amount of compound (IV-2) used is preferably 0.7 mol to 3 mol, more preferably 1 mol to 2 mol, relative to 1 mol of squaric acid represented by formula (IV-3).

[0092] In the process for producing compound (I), the amount of compound (IV-1) used is preferably 0.7 mol to 3 mol, more preferably 1 mol to 2 mol, relative to 1 mol of the reaction product (IV-9b).

[0093] The reaction temperature is preferably 30°C to 180°C, more preferably 80°C to 140°C. The reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.

[0094] The method for obtaining compound (I) as the target compound from the reaction mixture is not particularly limited, and various known methods can be employed, such as the above-mentioned methods.

[0095] (Coloring composition)

[0096] The coloring composition of the present invention contains a colorant (A) containing a compound (I) and a resin (B). The coloring composition may further contain a solvent (E), a leveling agent (F), etc. In this specification, the compounds exemplified as each component can be used alone or in combination of two or more without special mention.

[0097] The coloring composition of the present invention has an excellent absorbance retention rate before and after the light resistance test. The coloring composition also has excellent heat resistance.

[0098] (Colorant (A))

[0099] In addition to the compound (I), the colorant (A) contained in the coloring composition may also contain other dyes as the dye (A1). Examples of such dyes include oil-soluble dyes, acid dyes, amine salts of acid dyes, sulfonamide derivatives of acid dyes, etc. For example, compounds classified as solvent, acid, basic, reactive, direct, disperse, mordant or vat dyes in The Society of Dyers and Colourists publication, and known dyes described in Dyeing Notes (Color Dyeing Society) can be cited. In addition, according to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes and phthalocyanine dyes, etc. can be cited. These dyes can be used alone or in combination of two or more.

[0100] Specifically, C.I. Solvent Yellow 4 (hereinafter, the description of C.I. Solvent Yellow is omitted, and only the number is recorded), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;

[0101] C.I. Solvent Orange 2, 7, 11, 15, 26, 56;

[0102] C.I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;

[0103] C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0104] C.I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59:1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

[0105] C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33; etc. C.I. Solvent Dyes,

[0106] C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

[0107] C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

[0108] C.I. Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;

[0109] C.I. Acid Green 3, 5, 9, 25, 27, 28, 41;

[0110] C.I. Acid Violet 34, 120;

[0111] C.I. Acid Blue 25, 27, 40, 45, 78, 80, 112; etc. C.I. Acid Dyes,

[0112] C.I. Basic Green 1; etc. C.I. Basic Dyes,

[0113] C.I. Reactive Yellow 2, 76, 116;

[0114] C.I. Reactive Orange 16; etc. C.I. Reactive Dyes,

[0115] C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;

[0116] C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0117] C.I. Direct Blue 40; etc. C.I. direct dyes,

[0118] C.I. Disperse Yellow 51, 54, 76;

[0119] C.I. Disperse Violet 26, 27;

[0120] C.I. Disperse Blue 1, 14, 56, 60; etc. C.I. disperse dyes,

[0121] As C.I. mordant dyes, C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0122] C.I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; etc. C.I. mordant dyes,

[0123] C.I. Vat Green 1 etc. C.I. vat dyes etc.

[0124] In the dye (A1), the content of the compound (I) is preferably 3 parts by mass to 100 parts by mass or less, more preferably 10 parts by mass to 70 parts by mass, and still more preferably 15 parts by mass to 50 parts by mass, relative to 100 parts by mass of the total amount of the dye (A1). If the content of the compound (I) is within the above range, high color reproducibility is obtained when a color filter is produced, and there is a tendency to be easily made into a thin film.

[0125] The colorant (A) contained in the coloring composition preferably contains a pigment (A2). As the pigment (A2), there is no particular limitation, and known pigments can be used. For example, pigments classified as pigments in The Society of Dyers and Colourists can be used alone or in combination of two or more.

[0126] As the pigment (A2), for example, yellow pigments such as C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214, etc. can be cited;

[0127] Orange pigments such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.;

[0128] Red pigments such as C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, etc.;

[0129] Blue pigments such as C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60, etc.;

[0130] Purple pigments such as C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38, etc.;

[0131] Green pigments such as C.I. Pigment Green 7, 36, 58, etc.;

[0132] Brown pigments such as C.I. Pigment Brown 23, 25, etc.; and

[0133] Black pigments such as C.I. Pigment Black 1, 7, etc.

[0134] As the pigment (A2), yellow pigments such as C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, etc. are preferred; green pigments such as C.I. Pigment Green 7, 36, 58, etc. are more preferred, C.I. Pigment Yellow 138, 150, 185 and C.I. Pigment Green 58 are further preferred, and C.I. Pigment Yellow 138 and C.I. Pigment Green 58 are even more preferred. By containing the above pigments, it is thus easy to optimize the transmission spectrum, and the light resistance and reagent resistance of the color filter become good.

[0135] The pigment can be subjected to surface treatments such as rosin treatment as needed, surface treatment using pigment derivatives into which acidic groups or basic groups are introduced, graft treatment of the pigment surface using polymer compounds, micronization treatment based on the sulfuric acid micronization method, or cleaning treatment using organic solvents or water for removing impurities, removal treatment of ionic impurities based on the ion exchange method, etc.

[0136] The pigment preferably has a uniform particle size. By performing a dispersion treatment containing a pigment dispersant, a pigment dispersion liquid in a state where the pigment is uniformly dispersed in the solution can be obtained.

[0137] Examples of the pigment dispersant include surfactants, which can be any of cationic, anionic, nonionic, and amphoteric surfactants. Specifically, surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants can be mentioned. These pigment dispersants can be used alone or in combination of two or more. Examples of the pigment dispersant by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK), etc.

[0138] When using a pigment dispersant, its usage amount is preferably 1 part by mass to 100 parts by mass, more preferably 5 parts by mass to 50 parts by mass, relative to 100 parts by mass of the total amount of the pigment (A2). If the usage amount of the pigment dispersant is within the above range, there is a tendency to obtain a pigment dispersion liquid in a uniform dispersion state.

[0139] When the coloring agent (A) contains the pigment (A2), the content ratio of the dye (A1) to the pigment (A2) in the coloring agent (A) is usually 45:55 to 1:99 by mass basis, preferably 40:60 to 2:98, more preferably 38:62 to 3:97.

[0140] The content of the coloring agent (A) is preferably 5 parts by mass to 60 parts by mass, more preferably 8 parts by mass to 55 parts by mass, further preferably 10 parts by mass to 50 parts by mass, relative to 100 parts by mass of the solid content of the coloring composition. If the content of the coloring agent (A) is within the above range, the color density when forming a color filter is sufficient, and the coloring composition can contain a required amount of the resin (B), etc., so there is a tendency to be easily made into a thin film. Here, the "solid content" in this specification refers to the substance obtained by removing the solvent from the coloring composition. The total amount of the solid content and the content of each component relative to the solid content can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0141] (Resin (B))

[0142] The resin (B) contained in the coloring composition is not particularly limited, and an alkali-soluble resin is preferred. As the resin (B), the following resins [K1] to [K6] etc. can be mentioned.

[0143] Resin [K1]: A copolymer of at least one (Ba) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(Ba)") and a monomer (Bb) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(Bb)");

[0144] Resin [K2]: A copolymer of (Ba), (Bb), and a monomer (Bc) copolymerizable with (Ba) (where (Ba) is different from (Bb)) (hereinafter sometimes referred to as "(Bc)");

[0145] Resin [K3]: A copolymer of (Ba) and (Bc);

[0146] Resin [K4]: A resin obtained by reacting a copolymer of (Ba) and (Bc) with (Bb);

[0147] Resin [K5]: A resin obtained by reacting a copolymer of (Bb) and (Bc) with (Ba);

[0148] Resin [K6]: A resin obtained by reacting a copolymer of (Bb) and (Bc) with (Ba) and further reacting with a carboxylic anhydride.

[0149] Specifically, as (Ba), for example, unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, o -, m -, p -vinylbenzoic acid, etc. can be mentioned;

[0150] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3 - vinylphthalic acid, 4 - vinylphthalic acid, 3,4,5,6 - tetrahydrophthalic acid, 1,2,3,6 - tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, 1,4 - cyclohexenedicarboxylic acid, etc.;

[0151] Bicyclic unsaturated compounds containing a carboxyl group such as methyl - 5 - norbornene - 2,3 - dicarboxylic acid, 5 - carboxybicyclo[2.2.1]hept - 2 - ene, 5,6 - dicarboxybicyclo[2.2.1]hept - 2 - ene, 5 - carboxy - 5 - methylbicyclo[2.2.1]hept - 2 - ene, 5 - carboxy - 5 - ethylbicyclo[2.2.1]hept - 2 - ene, 5 - carboxy - 6 - methylbicyclo[2.2.1]hept - 2 - ene, 5 - carboxy - 6 - ethylbicyclo[2.2.1]hept - 2 - ene, etc.;

[0152] Unsaturated dicarboxylic anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;

[0153] Unsaturated mono-[(meth)acryloyloxyalkyl] esters of polycarboxylic acids with 2 or more carboxyl groups such as succinic acid mono-[2-(meth)acryloyloxyethyl] ester and phthalic acid mono-[2-(meth)acryloyloxyethyl] ester;

[0154] Unsaturated (meth)acrylic acid esters containing a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl) acrylate;

[0155] Among them, from the aspect of copolymerization reactivity and from the aspect of the solubility of the obtained resin in an aqueous alkali solution, (meth)acrylic acid, maleic anhydride, etc. are preferred.

[0156] (Bb) refers to a polymerizable compound having a cyclic ether structure with 2 to 4 carbon atoms (for example, at least 1 selected from an ethylene oxide ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenic unsaturated bond. (Bb) preferably has a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0157] In this specification, “(meth)acrylic acid” means at least one of acrylic acid and methacrylic acid. The same applies to descriptions such as “(meth)acryloyl group” and “(meth)acrylate”.

[0158] Examples of (Bb) include monomers having an epoxyethyl group and an ethylenic unsaturated bond, monomers having an oxetanyl group and an ethylenic unsaturated bond, monomers having a tetrahydrofuranyl group and an ethylenic unsaturated bond, etc.

[0159] As (Bb), in terms of further improving the reliability such as heat resistance and chemical resistance of the obtained color filter, a monomer having an epoxyethyl group and an ethylenic unsaturated bond is preferred.

[0160] Examples of (Bc) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, (meth)acrylate tricyclo[5.2.1.0 2,6Decan-8-yl ester (In this technical field, as a common name, it is called "(meth)acrylic acid dicyclopentyl ester". Additionally, it is sometimes called "(meth)acrylic acid tricyclodecyl ester)", "(meth)acrylic acid tricyclo[5.2.1.0 2,6 Decen-8-yl ester (In this technical field, as a common name, it is called "(meth)acrylic acid dicyclopentenyl ester", "(meth)acrylic acid dicyclopentyloxyethyl ester", "(meth)acrylic acid isobornyl ester", "(meth)acrylic acid adamantyl ester", "(meth)acrylic acid allyl ester", "(meth)acrylic acid propargyl ester", "(meth)acrylic acid phenyl ester", "(meth)acrylic acid naphthyl ester", "(meth)acrylic acid benzyl ester, etc. (meth)acrylic acid esters;

[0161] (Meth)acrylic acid 2-hydroxyethyl ester, (meth)acrylic acid 2-hydroxypropyl ester, etc. hydroxy-containing (meth)acrylic acid esters;

[0162] Diethyl maleate, diethyl fumarate, diethyl itaconate, etc. dicarboxylic acid diesters;

[0163] Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene, etc. bicyclic unsaturated compounds;

[0164] Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl 3-maleimidobenzoate, N-succinimidyl 4-maleimidobutyrate, N-succinimidyl 6-maleimidohexanoate, N-succinimidyl 3-maleimidopropionate, N-(9-acridinyl)maleimide, etc.;

[0165] Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.

[0166] Among them, from the aspects of copolymerization reactivity and heat resistance, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, etc. are preferred.

[0167] As the resin (B), specifically, examples thereof include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2.6 decyl acrylate / (meth)acrylic acid copolymer and other resins [K1]; glycidyl (meth)acrylate / (meth)benzyl acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2.6 decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2.6Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer / (meth)acrylate copolymer containing hydroxyl group, 3-methyl-3-(meth)acryloxymethyloxetane / (meth)acrylic acid / styrene copolymer and other resins [K2]; (meth)benzyl acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and other resins [K3]; Resins obtained by adding glycidyl (meth)acrylate to (meth)benzyl acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / (meth)benzyl acrylate / (meth)acrylic acid copolymer and other resins [K4]; Resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate, resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate and other resins [K5]; Resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate and then reacting with tetrahydrophthalic anhydride and other resins [K6], etc.

[0168] Among them, as the resin (B), resin [K1] and resin [K2] are preferred.

[0169] For example, resin [K1] can be manufactured with reference to the methods described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, issued on March 1, 1972) and the cited references described in this literature.

[0170] It should be noted that the obtained copolymer can directly use the solution after the reaction, or can use a concentrated or diluted solution, or can also use the substance taken out in the form of a solid (powder) by methods such as reprecipitation. In particular, during this polymerization, by using the solvent contained in the coloring composition of the present invention as the solvent, the solution after the reaction can be directly used for preparing the coloring composition of the present invention, so that the manufacturing process of the coloring composition of the present invention can be simplified.

[0171] The polystyrene-reduced weight average molecular weight of the resin (B) is preferably 3000 to 100000, more preferably 5000 to 50000, and further preferably 5000 to 30000. If the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed part in the developer is good, and there is a tendency to improve the resolution of the coloring pattern.

[0172] The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of resin (B) is preferably from 1.1 to 6, more preferably from 1.2 to 4.

[0173] The acid value of resin (B) is preferably from 50 to 170 mg-KOH / g, more preferably from 60 to 150, and further preferably from 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0174] The content of resin (B) is preferably from 10 to 90 parts by mass, more preferably from 20 to 85 parts by mass, and further preferably from 30 to 80 parts by mass with respect to 100 parts by mass of the solid content. When the content of resin (B) is within the above range, a colored pattern can be formed, and there is a tendency for the resolution and residual film rate of the colored pattern to increase.

[0175] (Solvent (E))

[0176] The solvent (E) that can be contained in the coloring composition is not particularly limited, and solvents commonly used in the art can be used alone or in combination of two or more. For example, ester solvents (solvents containing -COO- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -COO- in the molecule), alcohol solvents (solvents containing OH and not containing -O-, -CO-, and -COO- in the molecule), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. can be mentioned.

[0177] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexyl acetate, and γ-butyrolactone.

[0178] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole. Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

[0179] As the ether ester solvent, examples thereof include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate, etc.

[0180] As the ketone solvent, examples thereof include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone, etc.

[0181] As the alcohol solvent, examples thereof include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol, etc.

[0182] As the aromatic hydrocarbon solvent, examples thereof include benzene, toluene, xylene, and mesitylene, etc.

[0183] As the amide solvent, examples thereof include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, etc.

[0184] As the solvent, it is preferably selected from 1 kind of solvent or a mixed solvent combining 2 or more kinds selected from propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 3-methoxybutyl acetate, 3-methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone, N-methylpyrrolidone, N,N-dimethylformamide, and tetrahydrofuran, and more preferably selected from 1 kind of solvent or a mixed solvent combining 2 or more kinds selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, N-methylpyrrolidone, N,N-dimethylformamide, and tetrahydrofuran.

[0185] The content of the solvent (E) is preferably 70 to 95 parts by mass, more preferably 75 to 92 parts by mass, relative to 100 parts by mass of the coloring composition of the present invention. In other words, the total amount of the solid components of the coloring composition is preferably 5 to 30 parts by mass, more preferably 8 to 25 parts by mass. If the content of the solvent (E) is within the above range, the flatness during coating is good, and since the color density will not be insufficient when forming a color filter, there is a tendency for the display characteristics to become good.

[0186] (Leveling agent (F))

[0187] Examples of the leveling agent (F) that can be included in the coloring composition include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may have a polymerizable group in the side chain.

[0188] Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC) etc.

[0189] As a fluorine-based surfactant, surfactants having a fluorocarbon chain in the molecule can be cited. Specifically, FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFACE (registered trademark) F142D, MEGAFACE F171, MEGAFACE F172, MEGAFACE F173, MEGAFACE F177, MEGAFACE F183, MEGAFACE F554, MEGAFACE R30, MEGAFACE RS-718-K (manufactured by DIC Corporation), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.) etc. can be cited.

[0190] As a silicone-based surfactant having a fluorine atom, surfactants having a siloxane bond and a fluorocarbon chain in the molecule can be cited. Specifically, MEGAFACE (registered trademark) R08, MEGAFACE BL20, MEGAFACE F475, MEGAFACE F477, and MEGAFACE F443 (manufactured by DIC Corporation) etc. can be cited.

[0191] The content of the leveling agent (F) is preferably 0.0001 parts by mass to 0.2 parts by mass, more preferably 0.0002 parts by mass to 0.1 parts by mass, and further preferably 0.0003 parts by mass to 0.05 parts by mass with respect to 100 parts by mass of the coloring composition. It should be noted that this content does not include the content of the pigment dispersant. If the content of the leveling agent (F) is within the above range, the flatness of the color filter can be made good.

[0192] (Other components in the coloring composition)

[0193] The coloring composition may contain additives known in the art such as fillers, other high molecular compounds, adhesion promoters, antioxidants, and light stabilizers as needed.

[0194] (Manufacturing method of the coloring composition)

[0195] The coloring composition can be adjusted, for example, by mixing the colorant (A), the resin (B), the solvent (E), the leveling agent (F), and other components together as needed.

[0196] The pigment (A2) is preferably premixed with part or all of the solvent (E) and dispersed using a bead mill or the like to an average particle diameter of about 0.2 μm or less. At this time, the above-mentioned pigment dispersant and part or all of the resin (B) can be blended as needed. By mixing the remaining components in the pigment dispersion liquid thus obtained to a prescribed concentration, the target coloring composition can be prepared.

[0197] The dye can be separately dissolved in part or all of the solvent (E) in advance to prepare a solution. It is preferable to filter the solution through a filter having a pore size of about 0.01 to 1 μm.

[0198] It is preferable to filter the mixed coloring composition through a filter having a pore size of about 0.1 to 10 μm.

[0199] (Coloring curable resin composition)

[0200] The coloring curable resin composition of the present invention contains the above-mentioned coloring composition, a polymerizable compound (C), and a polymerization initiator (D). The coloring curable resin composition may further contain a polymerization initiation aid (D1).

[0201] The coloring curable resin composition of the present invention can be expected to have an excellent absorbance retention rate before and after a light resistance test. The heat resistance of the coloring curable resin composition is also excellent. For example, it can also have an excellent absorbance retention rate before and after a heat resistance test.

[0202] (Polymerizable compound (C))

[0203] The polymerizable compound (C) contained in the coloring curable resin composition is a compound that can be polymerized by active radicals and / or acids generated by the polymerization initiator (D). For example, compounds having a polymerizable ethylenically unsaturated bond can be cited, and (meth)acrylate compounds are preferred.

[0204] Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds. As such a polymerizable compound, for example, nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, compounds having 1 ethylenically unsaturated bond such as the compounds exemplified as the above (Ba), (Bb), and (Bc);

[0205] Compounds having 2 ethylenically unsaturated bonds such as 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate;

[0206] Compounds having 3 ethylenically unsaturated bonds such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tris(2-(meth)acryloyloxyethyl) isocyanurate, etc.;

[0207] Compounds having 4 ethylenically unsaturated bonds such as pentaerythritol tetra(meth)acrylate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, etc.;

[0208] Compounds having 5 ethylenically unsaturated bonds such as dipentaerythritol penta(meth)acrylate, etc.;

[0209] Compounds having 6 ethylenically unsaturated bonds such as dipentaerythritol hexa(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, etc.;

[0210] Compounds having 7 or more ethylenically unsaturated bonds such as tripentaerythritol hepta(meth)acrylate, tripentaerythritol octa(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, etc.; etc.

[0211] Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds, and more preferably a polymerizable compound having 5 to 6 ethylenically unsaturated bonds.

[0212] Among them, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are particularly preferred.

[0213] The weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2900, and more preferably 250 to 1500.

[0214] The content of the polymerizable compound (C) is preferably 7 to 65 parts by mass, more preferably 13 to 60 parts by mass, and further preferably 17 to 55 parts by mass with respect to 100 parts by mass of the solid content. If the content of the polymerizable compound (C) is within the above range, there is a tendency for the residual film rate during the formation of the colored pattern and the chemical resistance of the color filter to be improved.

[0215] The content ratio of the resin (B) to the polymerizable compound (C) [resin (B): polymerizable compound (C)] is preferably 20:80 to 80:20, and more preferably 35:65 to 80:20 on a mass basis.

[0216] (Polymerization initiator (D))

[0217] The polymerization initiator (D) contained in the colored curable resin composition is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. under the action of light or heat to initiate polymerization, and known polymerization initiators can be used. As the polymerization initiator that generates active radicals, for example, O-acyl oxime compounds, alkyl phenyl ketone compounds, triazine compounds, acyl phosphine oxide compounds, and biimidazole compounds can be cited.

[0218] The O-acyl oxime compound is a compound having a partial structure represented by the formula (Dd1). Hereinafter, * represents a bonding site.

[0219]

[0220] As the O-acyl oxime compound, for example, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolanylmethoxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, etc. can be cited. Commercially available products such as IRGACURE (registered trademark) OXE01, OXE02 (above, manufactured by BASF), N-1919 (manufactured by ADEKA) can be used. Among them, the O-acyl oxime compound is preferably at least one selected from N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine or N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine. When these are O-acyl oxime compounds, there is a tendency to obtain a color filter with high brightness.

[0221] An alkyl phenyl ketone compound is a compound having a partial structure represented by the following formula (Dd2) or a partial structure represented by the following formula (Dd3). In these partial structures, the benzene ring may have substituents.

[0222]

[0223] Examples of the compound having a partial structure represented by the formula (Dd2) include 2-methyl-2-morpholino-1-(4-methylthiophenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as IRGACURE 369, 907, 379 (manufactured by BASF Corporation) can also be used.

[0224] Examples of the compound having a partial structure represented by the formula (Dd3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, benzil dimethyl ketal, etc.

[0225] In terms of sensitivity, as the alkyl phenyl ketone compound, a compound having a partial structure represented by the formula (Dd2) is preferred.

[0226] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0227] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyl diphenylphosphine oxide, etc. Commercially available products such as IRGACURE (registered trademark) 819 (manufactured by BASF Corporation) can also be used.

[0228] As a benzimidazole compound, for example, a compound represented by the following formula (Dd4) can be cited.

[0229]

[0230] [In formula (Dd4), R d1 ~R d5 represent an aryl group having 6 to 10 carbon atoms which may have a substituent.]

[0231] In formula (Dd4), as the aryl group having 6 to 10 carbon atoms for R d1 ~R d5 , phenyl, methylphenyl, dimethylphenyl, ethylphenyl, naphthyl, etc. can be cited, and phenyl is preferred.

[0232] As the substituent which the aryl group having 6 to 10 carbon atoms may have, a halogen atom and an alkoxy group having 1 to 4 carbon atoms can be cited. As the halogen atom, R 1 ~R 4 exemplified in formula (I) can be cited. As the alkoxy group having 1 to 4 carbon atoms, methoxy, ethoxy, propoxy, and butoxy can be cited, and methoxy is preferred.

[0233] As the benzimidazole compound, specifically, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(alkoxyphenyl)benzimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)benzimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)benzimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Laid-Open No. 62-174204, etc.), a benzimidazole compound in which the phenyl groups at the 4,4',5,5'-positions are substituted with a carbonylalkoxy group (for example, refer to Japanese Patent Laid-Open No. 7-10913, etc.) and the like can be cited. Among them, a compound represented by the following formula and a mixture thereof are preferred.

[0234]

[0235] In addition, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl phenylglyoxylate, titanocene compounds, etc. These are preferably used in combination with the polymerization initiator assistant (D1) (especially amines) described later.

[0236] Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl toluenesulfonate; benzoin toluenesulfonate, etc.

[0237] As the polymerization initiator (D), a polymerization initiator that generates active radicals is preferred, and a polymerization initiator containing at least one selected from alkylbenzene ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds is more preferred, and a polymerization initiator containing an O-acyl oxime compound is further preferred.

[0238] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass in total of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, there is a tendency to shorten the exposure time due to high sensitivity, and thus the productivity of the color filter is improved.

[0239] (Polymerization initiator assistant (D1))

[0240] The polymerization initiator assistant (D1) that can be contained in the colored curable resin composition is a compound or a sensitizer that promotes the polymerization of the polymerizable compound initiated by the polymerization initiator. When the polymerization initiator assistant (D1) is contained, it is usually used in combination with the polymerization initiator (D).

[0241] Examples of the polymerization initiator assistant (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0242] Examples of the amine compound include alkanolamines such as triethanolamine, methyldiethanolamine, and triisopropanolamine; aminobenzoates such as methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-diethylaminoethyl benzoate, and 2-ethylhexyl 4-dimethylaminobenzoate; alkylaminobenzophenones such as N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone; etc. Among them, alkylaminobenzophenones are preferred, and 4,4'-bis(diethylamino)benzophenone is more preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) can be used.

[0243] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, etc.

[0244] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, etc.

[0245] Examples of the carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc.

[0246] When using these polymerization initiation aids (D1), its content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and there is a tendency to improve the productivity of the color filter.

[0247] (Other components in the colored curable resin composition)

[0248] The colored curable resin composition may contain additives known in the art such as a chain transfer agent as needed.

[0249] (Method for producing the colored curable resin composition)

[0250] The colored curable resin composition can be prepared, for example, by mixing a coloring composition with a polymerizable compound (C), a polymerization initiator (D), a polymerization initiation aid (D1), and other components. The colored curable resin composition is preferably used in the case of patterning by lithography. It is preferred to filter the mixed colored curable resin composition through a filter having a pore size of about 0.1 to 10 μm.

[0251] (Color Filter and Method for Manufacturing the Same)

[0252] The color filter of the present invention can be formed from the above-described coloring composition or colored curable resin composition. The color filter of the present invention has excellent absorbance retention rates before and after a light resistance test. The heat resistance of the color filter is also excellent.

[0253] As a method for manufacturing a color filter formed from a coloring composition or a colored curable resin composition, for example, there can be mentioned a method in which the coloring composition or colored curable resin composition is coated on a substrate and heated and dried (pre-baked) and / or dried under reduced pressure to remove volatile components such as solvents to dry it, a smooth composition layer is formed, and then post-baking is performed. The cured coating film thus formed can be the color filter of the present invention.

[0254] As the substrate, glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass coated with silica on the surface, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, and substrates having an aluminum, silver, silver / copper / palladium alloy thin film or the like formed on the above substrates can be used. Other color filter layers, resin layers, transistors, circuits, etc. can be formed on these substrates.

[0255] As the coating method, there can be mentioned a spin coating method, a slit coating method, a slit spin coating method, etc.

[0256] When performing heating and drying, the temperature is preferably 30 to 120 °C, more preferably 50 to 110 °C. As the heating time, it is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

[0257] When performing drying under reduced pressure, it is preferably performed in a pressure range of 50 to 150 Pa and a temperature range of 20 to 25 °C.

[0258] The thickness of the composition layer formed by coating the coloring composition or colored curable resin composition is not particularly limited and can be appropriately selected according to the film thickness of the target color filter.

[0259] It is preferred to further perform post-baking on the obtained composition layer. The post-baking temperature is preferably 150 to 250 °C, more preferably 160 to 235 °C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

[0260] The film thickness of the obtained color filter is not particularly limited and can be appropriately adjusted according to the purpose, use, etc. For example, it is 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

[0261] The cured coating film thus obtained can also be pattern-etched using, for example, an etching method or the like.

[0262] The coloring composition or the coloring curable resin composition of the present invention can also be used to produce a coloring pattern by a photolithography method, an inkjet method, a printing method, or the like. Among them, when using the coloring curable resin composition containing the polymerizable compound (C) and the polymerization initiator (D), the photolithography method is preferred. The photolithography method is a method of coating a coloring curable resin composition on a substrate and drying it to obtain a composition layer, and exposing and developing the coloring composition layer through a photomask. Coating and drying can be carried out under the above conditions.

[0263] The composition layer is exposed through a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target use is used.

[0264] As a light source that can be used for exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferred. For example, for light below 350 nm, a filter that cuts off this wavelength region can be used for cutoff, or for light near 436 nm, 408 nm, or 365 nm, a band-pass filter that extracts these wavelength regions can be used for selective extraction. Specifically, a mercury lamp, a light-emitting diode, a metal halide lamp, a halogen lamp, etc. can be mentioned.

[0265] Since parallel light can be uniformly irradiated on the entire exposure surface, and accurate alignment between the photomask and the substrate on which the composition layer is formed can be achieved, exposure apparatuses such as a mask aligner and a stepper are preferably used.

[0266] The exposed composition layer is developed by bringing it into contact with a developer, thereby forming a coloring pattern on the substrate. The unexposed portion of the composition layer is dissolved in the developer and removed by development. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. In addition, the developer may contain a surfactant.

[0267] The developing method can be any one of a spin-coating immersion (puddle) method, a dipping method, a spraying method, etc. In addition, during development, the substrate can be tilted at an arbitrary angle.

[0268] It is preferred to perform water washing after development.

[0269] Preferably, post-baking is performed on the obtained colored pattern. The post-baking temperature and time can be the same as the above temperature and time.

[0270] The color filter is preferably used for solid-state imaging elements and display devices (e.g., liquid crystal display devices, organic EL devices, electronic papers, etc.).

[0271] (Optical filter)

[0272] Compound (I) can be used, for example, for optical filters of display devices and the like. It can be expected that the optical filter has excellent absorbance retention rates before and after a light resistance test. It can also be expected that the optical filter has excellent heat resistance.

[0273] The optical filter is usually a layer formed from a composition containing a light-transmissive (preferably optically transparent) thermoplastic resin or thermosetting resin, and can be, for example, a film-like material. The optical filter only needs to have a layer containing compound (I) (hereinafter, sometimes referred to as "color correction layer"), and can be a color correction film composed of a single-layer structure of the color correction layer, or a laminate having a multi-layer structure including the color correction layer. When the optical filter has a multi-layer structure, it can include one layer of the color correction layer or two or more layers of the color correction layer. The compound (I) contained in two or more layers can be the same as or different from each other.

[0274] When the optical filter is a laminate, the color correction layer can be an adhesive layer or a resin layer other than the adhesive layer (hereinafter, sometimes simply referred to as "resin layer"). When the color correction layer is an adhesive layer, it can bond two layers contained in the optical filter to each other, or can be used to bond the optical filter to other components such as an image display element. The adhesive layer can be an adhesive layer formed from an adhesive or an adhesive layer formed from an adhesive.

[0275] When the optical filter with a single-layer structure of the color correction layer (color correction film) or, in the multi-layer structure optical filter, is a resin layer other than the adhesive layer, the method of making the color correction film or resin layer contain compound (I) is not particularly limited. For example, the following methods can be adopted: [i] A method of kneading with the resin forming the color correction film or resin layer and heat-molding it into a film shape; [ii] A method of dispersing or dissolving the resin forming the color correction film or resin layer or the monomer of the resin and compound (I) in an organic solvent and molding it into a film shape by a casting method or the like. In addition, [iii] A coating liquid in which compound (I) is dispersed or dissolved in a binder resin or an organic solvent can be coated on a resin substrate film to form a resin layer, and the film after peeling off the resin substrate film from the resin layer can also be used as the color correction film. The thickness of the color correction film and resin layer is not particularly limited, and can be, for example, 1 μm to 200 μm.

[0276] When the color correction film and the resin layer contain the compound (I), its content is not particularly limited. For example, the compound (I) can be 0.001 parts by mass or more, preferably 0.02 parts by mass or more, more preferably 0.05 parts by mass or more, relative to 100 parts by mass of the base polymer forming the color correction film and the resin layer. In addition, it can be 10 parts by mass or less, preferably 3 parts by mass or less, more preferably 0.5 parts by mass or less.

[0277] When the color correction layer is an adhesive layer, the method of making the adhesive layer contain the compound (I) is not particularly limited, as long as the compound (I) is added when preparing the adhesive composition or the binder composition for forming the adhesive layer. The thickness of the adhesive layer is not particularly limited. For example, it can be 1 μm to 100 μm.

[0278] When the adhesive layer contains the compound (I), its content is not particularly limited. For example, the compound (I) can be 0.01 parts by mass or more, preferably 0.02 parts by mass or more, more preferably 0.05 parts by mass or more, relative to 100 parts by mass of the base polymer of the adhesive and / or the binder contained in the adhesive layer. In addition, it can be 10 parts by mass or less, preferably 5 parts by mass or less, more preferably 0.5 parts by mass or less.

[0279] The optical filter can be used in display devices such as organic electroluminescent (organic EL) display devices and liquid crystal display devices, and can be used by being adhered to the visible side of the image display element of the display device. In this case, the optical filter preferably has an adhesive layer and a resin layer other than the adhesive layer, and at least one of the adhesive layer and the resin layer is preferably a color correction layer containing the compound (I).

[0280] When the optical filter is a laminate, its laminate structure is not particularly limited. For example, it can have Figure 1 the laminate structures shown in (a) and (b) in Figure 1 (a) and (b) in Figure 1 are cross-sectional schematic views showing an example of the optical filter. The optical filter 10 shown in (a) in

[0281] The first protective film 14, polarizing film 15, and second protective film 16 in the optical filter 10 form a polarizer, and the first protective film 14 and the second protective film 16 may have an adhesive layer on the side of the surface bonded to the polarizing film 15. The adhesive layer 11 for an image display element is used to bond to the light-emitting layer of an organic EL element including an image display element that is an organic EL display device. An unillustrated spacer (release film) may be provided on the surface of the adhesive layer 11 for an image display element on the side opposite to the retardation film 12.

[0282] Figure 1 The optical filter 20 shown in (b) in [description] can be used for a liquid crystal display device. The optical filter 20 may sequentially include, for example, an adhesive layer 21 for an image display element, a first protective film 24, a polarizing film 25, and a second protective film 26. The adhesive layer 21 for an image display element corresponds to the above-mentioned adhesive layer, and the first protective film 24, polarizing film 25, and second protective film 26 all correspond to the above-mentioned resin layer.

[0283] The first protective film 24, polarizing film 25, and second protective film 26 in the optical filter 20 form a polarizer, and the first protective film 24 and the second protective film 26 may have an adhesive layer on the side of the surface bonded to the polarizing film 25. The adhesive layer 21 for an image display element is used to bond to a liquid crystal cell that is an image display element of a liquid crystal display device. An unillustrated spacer (release film) may be provided on the surface of the adhesive layer 21 for an image display element on the side opposite to the first protective film 24.

[0284] It is possible to form Figure 1 at least any one of the resin layer and the adhesive layer of the optical filters 10 and 20 shown in (a) and (b) in [description] contains the compound (I). Figure 1 In the optical filter 10 shown in (a) in [description], the above-mentioned compound (I) may be contained in, for example, one or more of the adhesive layer 11 for an image display element, the adhesive layer 13, the first protective film 14, and the second protective film 16. Figure 1 In the optical filter 20 shown in (b), the compound (I) may be contained in, for example, one or more of the adhesive layer 21 for an image display element, the first protective film 24, and the second protective film 26.

[0285] Figure 1 The optical filters 10 and 20 shown in (a) and (b) in [description] are merely an example, and they may have a laminate structure other than the above. For example, other layers such as an antiglare film and a surface antireflection film may be provided on the surfaces of the second protective films 16 and 26 on the sides opposite to the polarizing films 15 and 25. In addition, the first protective films 14 and 24 may have the function of a retardation film, and the second protective films 16 and 26 may have an antiglare function, a surface antireflection function, the function of a retardation film, etc. Furthermore, in addition to forming Figure 1In addition to the respective layers of the optical filters 10 and 20 shown in (a) and (b) therein, a color correction layer containing the compound (I) may be provided at any position.

[0286] Since the above optical filter contains the compound (I), it is expected to have an excellent absorbance retention rate before and after the light resistance test. The heat resistance of the optical filter is also expected to be excellent.

[0287] Hereinafter, each component constituting the optical filter will be described in detail.

[0288] (Adhesive layer)

[0289] Examples of the adhesive that can be used for the adhesive layer include aqueous adhesives, energy ray-curable adhesives, and combinations thereof. Examples of the aqueous adhesive include an aqueous solution of a polyvinyl alcohol-based resin, an aqueous two-component polyurethane-based emulsion adhesive, and the like. The energy ray-curable adhesive is an adhesive that is cured by irradiating active energy rays such as ultraviolet rays. Examples thereof include an adhesive containing a polymerizable compound and a photopolymerization initiator, an adhesive containing a photoreactive resin, an adhesive containing a binder resin and a photoreactive crosslinking agent, and the like. Examples of the above polymerizable compound include photopolymerizable monomers such as photocurable epoxy-based monomers, photocurable (meth)acrylic acid-based monomers, photocurable polyurethane-based monomers, and oligomers derived from these monomers. Examples of the above photopolymerization initiator include a photopolymerization initiator containing a substance that generates active species such as neutral radicals, anionic radicals, and cationic radicals by irradiating active energy rays such as ultraviolet rays.

[0290] As the adhesive that can be used for the adhesive layer, conventionally known adhesives can be used. Examples of the adhesive include (meth)acrylic acid-based adhesives, polyurethane-based adhesives, silicone-based adhesives, polyester-based adhesives, polyamide-based adhesives, polyether-based adhesives, fluorine-based adhesives, rubber-based adhesives, and the like. In addition, it may also be an energy ray-curable adhesive, a heat-curable adhesive, or the like. Among them, from the viewpoints of transparency, adhesive strength, reliability, etc., it is preferable to use a (meth)acrylic acid-based adhesive.

[0291] The (meth)acrylic acid-based adhesive is not particularly limited and is a polymer mainly composed of (meth)acrylate (containing 50% by mass or more). It can be a homopolymer of one kind of (meth)acrylate or a copolymer of (meth)acrylate and other (meth)acrylates, etc. Examples of the (meth)acrylate include butyl (meth)acrylate, ethyl (meth)acrylate, methyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and 2-phenoxyethyl (meth)acrylate. In addition, polar monomers can be copolymerized in the polymer mainly composed of these (meth)acrylates. Examples of the polar monomer include monomers having polar functional groups such as carboxyl group, hydroxyl group, amide group, amino group, and epoxy group, such as (meth)acrylic acid, 2-hydroxypropyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, (meth)acrylamide, 2-(N,N-dimethylamino)ethyl (meth)acrylate, and glycidyl (meth)acrylate. The (meth)acrylic acid-based resin used in the (meth)acrylic acid-based adhesive can be a (meth)acrylic acid-based resin having a weight average molecular weight (Mw) of 100,000 or more, preferably 600,000 or more, and usually 2,500,000 or less.

[0292] These (meth)acrylic acid-based adhesives can be used alone, and usually, they are used in combination with a crosslinking agent. Examples of the crosslinking agent include substances containing divalent or polyvalent metal ions that form metal carboxylates with carboxyl groups, amine compounds that form amide bonds with carboxyl groups, epoxy compounds or diol compounds that form ester bonds with carboxyl groups, and isocyanate compounds that form amide bonds with carboxyl groups, etc. Among them, isocyanate compounds are preferably used.

[0293] Among the isocyanate-based compounds, isophthalic acid dimethyl diisocyanate, toluene diisocyanate, or hexamethylene diisocyanate is preferably used; adducts obtained by reacting polyhydric alcohols such as glycerol and trimethylolpropane with these isocyanate compounds; substances obtained by dimerizing or trimerizing these isocyanate compounds or mixtures thereof; mixtures of two or more of the above-mentioned isocyanate-based compounds, etc.

[0294] Examples of the preferred isocyanate-based compounds include toluene diisocyanate, adducts obtained by reacting polyhydric alcohols with toluene diisocyanate, dimers of toluene diisocyanate, trimers of toluene diisocyanate, hexamethylene diisocyanate, adducts obtained by reacting polyhydric alcohols with hexamethylene diisocyanate, dimers of hexamethylene diisocyanate, and trimers of hexamethylene diisocyanate.

[0295] The content of the crosslinking agent in the acrylic acid-based adhesive is usually 0 parts by mass to 5 parts by mass, preferably 0.05 parts by mass to 2 parts by mass, relative to 100 parts by mass of the (meth)acrylic acid-based resin.

[0296] The acrylic-based adhesive may further contain a silane compound. When the acrylic-based adhesive contains a silane compound, the adhesion between the resulting adhesive layer and an optical component such as a glass substrate can be improved.

[0297] Examples of the silane compound include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropyldimethoxymethylsilane, 3-glycidoxypropylethoxydimethylsilane, etc. Two or more silane compounds can be used.

[0298] The silane compound can be a silane compound of an organosilicon oligomer type. When the organosilicon oligomer is represented in the form of a (monomer) oligomer, examples include 3-mercaptopropyltrimethoxysilane-tetramethoxysilane copolymer, mercaptomethyltrimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-methacryloxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-acryloxypropyltrimethoxysilane-tetramethoxysilane copolymer, vinyltrimethoxysilane-tetramethoxysilane copolymer, etc.

[0299] The content of the silane compound in the adhesive composition is usually 0.01 parts by mass to 10 parts by mass, preferably 0.05 parts by mass to 5 parts by mass, and more preferably 0.1 parts by mass to 2 parts by mass with respect to 100 parts by mass of the (meth)acrylic resin. If the content of the silane compound is 0.01 parts by mass or more, the effect of improving the adhesion between the adhesive layer and an optical component such as a glass substrate can be easily obtained. In addition, if the content of the silane compound is 10 parts by mass or less, the exudation of the silane compound from the adhesive layer can be suppressed.

[0300] The acrylic-based adhesive may further contain an ionic compound as an antistatic agent for imparting antistatic properties. The ionic compound is a compound having an inorganic cation or an organic cation and an inorganic anion or an organic anion. The acrylic-based adhesive can contain two or more ionic compounds.

[0301] Examples of the inorganic cation include lithium cation [Li + , sodium cation [Na + , potassium cation [K +〕alkali metal ions such as, and beryllium cations [Be 2+ 〕, magnesium cations [Mg 2+ 〕, calcium cations [Ca 2+ 〕and other alkaline earth metal ions, etc.

[0302] Examples of the organic cation include an imidazolium cation, a pyridinium cation, a pyrrolidinium cation, an ammonium cation, a sulfonium cation, a phosphonium cation, and the like.

[0303] Examples of the inorganic anion include a chloride ion [Cl － 〕, a bromide ion [Br － 〕, an iodide ion [I － 〕, a tetrachloroaluminate anion [AlCl4 － 〕, a heptachlorodialuminate anion [Al2Cl7 － 〕, a tetrafluoroborate anion [BF4 － 〕, a hexafluorophosphate anion [PF6 － 〕, a perchlorate anion [ClO4 － 〕, a nitrate anion [NO3 － 〕, a hexafluoroarsenate anion [AsF6 － 〕, a hexafluoroantimonate anion [SbF6 － 〕, a hexafluoroniobate anion [NbF6 － 〕, a hexafluorotantalate anion [TaF6 － 〕, a dicyanamide anion [(CN)2N － 〕, etc.

[0304] Examples of the organic anion include an acetate anion [CH3COO － 〕, a trifluoroacetate anion [CF3COO － 〕, a methanesulfonate anion [CH3SO3 － 〕, a trifluoromethanesulfonate anion [CF3SO3 － 〕, a p-toluenesulfonate anion [p-CH3C6H4SO3 － 〕, a bis(fluorosulfonyl)imide anion [(FSO2)2N － 〕, a bis(trifluoromethanesulfonyl)imide anion [(CF3SO2)2N － 〕, a tris(trifluoromethanesulfonyl)methylated anion [(CF3SO2)3C － 〕, a dimethylphosphinate anion [(CH3)2POO － 〕, a (poly)hydrofluorofluoride anion [F(HF) n － 〕(n is about 1 to 3), a thiocyanate anion [SCN －, perfluorobutanesulfonate anion [C4F9SO3 － , bis(pentafluoroethanesulfonyl)imide anion [(C2F5SO2)2N － , perfluorobutyrate anion [C3F7COO － , (trifluoromethanesulfonyl)(trifluoromethanecarbonyl)imide anion [(CF3SO2)(CF3CO)N － , etc.

[0305] Specific examples of the ionic compound can be selected from combinations of the above cation components and anion components.

[0306] Examples of the ionic compound having an organic cation include pyridinium salts such as N-octylpyridinium hexafluorophosphate, N-octyl-4-methylpyridinium hexafluorophosphate, N-butyl-4-methylpyridinium hexafluorophosphate, N-decylpyridinium bis(bifluoromethylsulfonyl)imide salt, N-hexylpyridinium bis(trifluoromethanesulfonyl)imide salt, N-octylpyridinium bis(trifluoromethanesulfonyl)imide salt; imidazolium salts such as 1-ethyl-3-methylimidazolium hexafluorophosphate, 1-ethyl-3-methylimidazolium p-toluenesulfonate, 1-ethyl-3-methylimidazolium bis(fluorosulfonyl)imide salt, 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide salt, 1-butyl-3-methylimidazolium methanesulfonate; pyrrolidinium salts such as N-butyl-N-methylpyrrolidinium hexafluorophosphate, N-butyl-N-methylpyrrolidinium bis(fluorosulfonyl)imide salt, N-butyl-N-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide salt; and quaternary ammonium salts such as tetrabutylammonium hexafluorophosphate and tetrabutylammonium p-toluenesulfonate.

[0307] Examples of the ionic compound having an inorganic cation include lithium bromide, lithium iodide, sodium hexafluorophosphate, etc.

[0308] From the viewpoint of maintaining antistatic performance, the ionic compound is preferably a solid at room temperature. The ionic compound preferably has a melting point of 30 °C or higher, and further 35 °C or higher. On the other hand, if its melting point is too high, the compatibility with the (meth)acrylic resin becomes poor. Therefore, the melting point of the ionic compound is preferably 90 °C or lower, more preferably 70 °C or lower, and further preferably less than 50 °C.

[0309] The content of the ionic compound in the acrylic adhesive is preferably 0.1 to 8 parts by mass, more preferably 0.2 to 6 parts by mass, further preferably 0.5 to 5 parts by mass, and particularly preferably 1 to 5 parts by mass with respect to 100 parts by mass of the (meth)acrylic resin. A content of the ionic compound of 0.1 part by mass or more is beneficial for improving antistatic performance, and a content of 8 parts by mass or less is beneficial for maintaining the durability of the adhesive layer.

[0310] Various additives can be further incorporated into adhesives and binders. Examples of additives include rework agents, resin for imparting adhesiveness, antioxidants, ultraviolet absorbers, defoaming agents, etchers, light diffusing agents such as fine particles, and the like.

[0311] (Resin layer)

[0312] Examples of the resin layer include a polarizing film as a linear polarizer; a protective film provided for protecting the surface of the polarizing film and the like; a retardation film; an optical compensation film other than the retardation film; a film with an antiglare function having an uneven shape on the surface, a film with a surface antireflection function; a reflective film having a reflective function on the surface; a transflective film having both a reflective function and a transmissive function; a light diffusing film; a hard coat film; a color correction film, and the like. The optical filter can include one or more of the above resin layers.

[0313] Examples of the polarizing film include a polarizing film in which iodine is oriented in a polyvinyl alcohol-based resin layer, a polarizing film in which a liquid crystal compound and a dichroic pigment are oriented, and the like.

[0314] The material of the resin layer when it is other than the polarizing film is not particularly limited. Examples include polyolefin-based resins such as chain polyolefin-based resins (such as polyethylene-based resins and polypropylene-based resins), cyclic polyolefin-based resins (such as norbornene-based resins), etc.; cellulose ester-based resins such as triacetyl cellulose, diacetyl cellulose, and cellulose acetate propionate; polyester-based resins such as polyethylene terephthalate and polyethylene naphthalate; polycarbonate-based resins; (meth)acrylic acid-based resins such as (meth)acrylic acid and poly(methyl methacrylate); vinyl alcohol-based resins such as polyvinyl alcohol and polyvinyl acetate; polystyrene-based resins; mixtures, copolymers, etc. of these. These resins can contain one or more additives such as lubricants, plasticizers, dispersants, heat stabilizers, ultraviolet absorbers, infrared absorbers, antistatic agents, antioxidants, light diffusing agents such as fine particles.

[0315] (Display device)

[0316] The above color filters and optical filters can be preferably used for display devices such as organic EL display devices, liquid crystal display devices, inorganic electroluminescent (inorganic EL) display devices, field emission display devices, and electronic paper.

[0317] Figure 2 In (a) and (b) is a cross-sectional schematic view showing an example of a display device having an optical filter. Figure 2 The display device shown in (a) in is a display device including Figure 1The organic EL display device includes an optical filter 10 shown in (a) in [reference] and an image display element 1 having a light-emitting layer containing an organic EL element. The optical filter 10 can be disposed on the visible side of the image display element 1 via an adhesive layer 11 for the image display element.

[0318] Figure 2 The display device shown in (b) in [reference] includes Figure 1 The liquid crystal display device includes an optical filter 20 shown in (b) in [reference] and an image display element 2 having a liquid crystal cell containing a liquid crystal layer. The optical filter 20 can be disposed on the visible side of the image display element 2 via an adhesive layer 21 for the image display element.

[0319] Examples

[0320] Hereinafter, examples and comparative examples are shown to more specifically illustrate the present invention, but the present invention is not limited by these examples. In the examples, comparative examples, application examples, and comparative application examples, "parts" means parts by mass unless otherwise specified.

[0321] [Identification of Compounds]

[0322] The structure of the compound was identified by performing mass analysis (LC; Agilent 1200 series, MASS; Agilent LC / MSD series).

[0323] [Example 1 (Compound (I))]

[0324] 2.85 parts (8.8 mmol) of a compound represented by the following formula (IV-1-a) (a compound represented by formula (d-2) described in JP-A-2015-86379), 1.1 parts (8.8 mmol) of phloroglucinol represented by the following formula (IV-2-a) (manufactured by Tokyo Chemical Industry Co., Ltd.), 1 part (8.8 mmol) of 3,4-dihydroxy-3-cyclobutene-1,2-dione (squaric acid) represented by the following formula (IV-3) (manufactured by FUJIFILM Wako Pure Chemical Corporation), 33 parts (0.4 mol) of 1-butanol, and 55.2 parts (0.6 mol) of toluene were mixed. The water generated in the obtained mixture was removed using a Dean-Stark tube, and the mixture was stirred at 110 °C for 3 hours. The solvent in the reaction solution after the reaction was distilled off, 220 mL of ion-exchanged water was added, and the precipitated crude product was collected by filtration.

[0325]

[0326] The crude product obtained was separated by column chromatography using silica gel (developing solvent: chloroform) to obtain 1.5 parts of the compound represented by formula (A-1) (hereinafter sometimes referred to as "compound (A-1)"), and then dried under reduced pressure at 60 °C for 12 hours to obtain compound (A-1). The obtained compound (A-1) was subjected to mass analysis.

[0327] (Mass analysis) Ionization mode = ESI+: m / z = [M+H] + 530.5

[0328] Exact Mass: 529.3

[0329]

[0330] 〔Example 2 (Compound (I))〕

[0331] Using 1.94 parts (8.8 mmol) of N,N-diethyl-3-aminophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the following formula (IV-1-b) instead of the compound represented by formula (IV-1-a), and otherwise in the same manner as in Example 1, 0.91 part of the compound represented by formula (A-2) (hereinafter sometimes referred to as "compound (A-2)") was obtained. The obtained compound (A-2) was subjected to mass analysis.

[0332] (Mass analysis) Ionization mode = ESI+: m / z = [M+H] + 370.5

[0333] Exact Mass: 369.1

[0334]

[0335] 〔Comparative Example 1〕

[0336] In the synthesis method of compound (A-1) in Example 1, 5.70 parts (17.6 mmol) of the compound represented by formula (IV-1-a) was used, and phloroglucinol represented by formula (IV-2-a) was not used. Otherwise, in the same manner as in Example 1, 2.2 parts of the compound represented by formula (B-1) (hereinafter sometimes referred to as "compound (B-1)") was obtained. The obtained compound (B-1) was subjected to mass analysis. (Mass analysis) Ionization mode = ESI+: m / z = [M+H] + 730.0

[0337] Exact Mass: 728.5

[0338]

[0339] 〔Comparative Example 2〕

[0340] In the synthesis method of the compound (A-1) of Example 1, 3.88 parts (17.5 mmol) of N,N-dibutyl-3-aminophenol represented by the following formula (IV-1-c) was used instead of the compound represented by formula (IV-1-a), and phloroglucinol represented by formula (IV-2-a) was not used. Otherwise, 3.4 parts of the compound represented by formula (B-2) (hereinafter sometimes referred to as "compound (B-2)") was obtained in the same manner as in Example 1. Quality analysis was performed on the obtained compound (B-2).

[0341] (Quality analysis) Ionization mode = ESI+: m / z = [M+H] + 521.5

[0342] Exact Mass: 520.3

[0343]

[0344] 〔Example 3 (Coloring Composition)〕

[0345] (Synthesis of Resin (B1))

[0346] After flowing an appropriate amount of nitrogen into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with a nitrogen atmosphere, 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were charged, and the mixture was heated to 85 °C while stirring. Then, a mixed solution of 38 parts of acrylic acid, 25 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 dec-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 dec-9-yl acrylate (content ratio 1:1), 137 parts of cyclohexyl maleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a mixed solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was maintained at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B1)) solution having a B-type viscosity (23 °C) of 23 mPas and a solid content of 25.6%. The weight-average molecular weight Mw of the resulting copolymer was 8000, the solid content acid value was 111 mg-KOH / g, and the dispersity was 2.1. The measurement of the weight-average molecular weight Mw and the number-average molecular weight Mn and the calculation of the dispersity were carried out by the methods described below. Resin (B1) has the following structural units.

[0347]

[0348] (Preparation of Coloring Composition)

[0349] The coloring composition (a-1) was obtained by mixing the following components.

[0350]

[0351]

[0352] (Production of Colored Coating Film (a-1))

[0353] After applying the coloring composition (a-1) onto a 5 cm square glass substrate (EAGLE2000; manufactured by Corning Inc.) by spin coating, it was pre-baked at 100 °C for 3 minutes to form a composition layer. Thereafter, it was post-baked in an oven at 230 °C for 3 minutes to obtain the colored coating film (a-1). The obtained colored coating film (a-1) was used for a light resistance test. The results are shown in Table 1.

[0354] [Light Resistance Test]

[0355] An ultraviolet cut-off filter (COLORED OPTICAL GLASS L38, manufactured by HOYA Corporation, which cuts off light of 380 nm or less) was placed on the obtained colored coating film (a-1), and xenon lamp light was irradiated for 24 hours using a light resistance testing machine (SUNTEST CPS+, manufactured by Toyo Seiki Seisaku-sho, Ltd.). Before and after the light irradiation, the absorbance at the maximum absorption wavelength of the colored coating film (a-1) was measured. Taking the absorbance before the light irradiation as 100%, the absorbance after the light irradiation was calculated. The maximum absorption wavelength of the colored coating film (a-1) is shown in Table 1. The absorbance was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation).

[0356] [Example 4 (Coloring Composition)]

[0357] 0.11 part of compound (A-2) as the colorant (A) was used instead of compound (A-1), and otherwise, the colored composition (a-2) was obtained in the same manner as in Example 1. In addition, using this colored composition (a-2), otherwise, the colored coating film (a-2) was obtained in the same manner as in Example 1. Using the obtained colored coating film (a-2), a light resistance test was carried out in the same order as in Example 3. The results are shown in Table 1.

[0358] [Comparative Example 3]

[0359] 0.13 part of compound (B-1) was used instead of compound (A-1), and otherwise, the colored composition (b-1) was obtained in the same manner as in Example 1. In addition, using this colored composition (b-1), otherwise, the colored coating film (b-1) was obtained in the same manner as in Example 1. Using the obtained colored coating film (b-1), a light resistance test was carried out in the same order as in Example 3. The results are shown in Table 1.

[0360] [Comparative Example 4]

[0361] Compound (B-2) in an amount of 0.13 part was used in place of compound (A-1), and otherwise, the colored composition (b-2) was obtained in the same manner as in Example 1. Further, using this colored composition (b-2), the colored coating film (b-2) was obtained in the same manner as in Example 1. Using the obtained colored coating film (b-2), the light resistance test was carried out in the same order as in Example 3. The results are shown in Table 1.

[0362] [Table 1]

[0363]

[0364] As shown in Table 1, the absorbance retention rate of the colored composition containing compound (I) before and after the light resistance test was excellent.

[0365] [Example 5 (Colored curable resin composition)]

[0366] (Synthesis of resin (B2))

[0367] An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 280 parts of propylene glycol monomethyl ether acetate was charged and heated to 80 °C while stirring. Then, a mixed solution of 38 parts of acrylic acid, 289 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 dec-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 dec-9-yl acrylate (mixing ratio 1:1), and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a mixed solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the inside of the flask was maintained at 80 °C for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B2)) solution having a B-type viscosity (23 °C) of 125 mPa·s and a solid content of 35.1%. The weight-average molecular weight Mw of the resulting copolymer was 9200, the dispersity was 2.08, and the solid content acid value was 77 mg-KOH / g. Resin (B2) has the following structural units.

[0368]

[0369] The measurement of the polystyrene-equivalent weight-average molecular weight (Mw) and number-average molecular weight (Mn) of resin (B1) and resin (B2) was carried out by the GPC method under the following conditions.

[0370] Apparatus: HLC-8120GPC (manufactured by TOSOH CORPORATION)

[0371] Column: TSK-GEL G2000HXL

[0372] Column temperature: 40 °C

[0373] Solvent: THF

[0374] Flow rate: 1.0 mL / min

[0375] Concentration of solid component in the test solution: 0.001 - 0.01 mass%

[0376] Injection volume: 50 μL

[0377] Detector: RI

[0378] Standard substance for calibration: TSK STANDARD POLYSTYRENE

[0379] F-40, F-4, F-288, A-2500, A-500

[0380] (Manufactured by TOSOH CORPORATION)

[0381] The ratio (Mw / Mn) of the weight-average molecular weight to the number-average molecular weight of the polystyrene obtained above is defined as the dispersity.

[0382] (Preparation of colored curable resin composition (a-3))

[0383] The respective components are mixed so as to have the composition shown in Table 2 to obtain a colored curable resin composition.

[0384] [Production of colored coating film (color filter)]

[0385] The colored curable resin composition (a-3) is applied onto a glass substrate (EAGLE2000; manufactured by Corning Inc.) having a size of 5 cm square by spin coating, and then pre-baked at 100 °C for 3 minutes to form a colored curable resin composition layer. After cooling, using an exposure machine (TME-150RSK; manufactured by TOPCON CORPORATION), in an atmospheric atmosphere, the colored curable resin composition layer formed on the substrate is irradiated with light at an exposure dose of 100 mJ / cm 2 (based on 365 nm). After the light irradiation, it is post-baked in an oven at 230 °C for 30 minutes to obtain a colored coating film (a-3).

[0386] [Heat resistance test]

[0387] The obtained colored coating film (a-3)

[0388] Before and after post-baking, the absorbance at the maximum absorption wavelength of the colored coating film (a-3) was measured. Taking the absorbance before post-baking as 100%, the absorbance after post-baking was calculated. The absorbance was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation). The results are shown in Table 2.

[0389] [Comparative Example 5]

[0390] Compound (B-1) was used in place of compound (A-1), and the respective components were mixed so as to have the composition shown in Table 2. Other than that, a colored curable resin composition (b-3) was obtained in the same manner as in Example 5. Using this colored curable resin composition (b-3), a colored coating film (b-3) was obtained in the same manner as in Example 5. The obtained colored coating film (b-3) was subjected to a heat resistance test in the same order as in Example 5. The results are shown in Table 2.

[0391] [Table 2]

[0392]

[0393] In Table 2, each component represents the following compound.

[0394] Compound (A-1): The compound represented by formula (A-1) as the colorant (A)

[0395] Compound (B-1): The compound represented by formula (B-1)

[0396] Resin (B): Resin (B2) (in terms of solid content)

[0397] Polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

[0398] Polymerization initiator (D): N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine (PBG-327; oxime compound; manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.)

[0399] Solvent (E): Propylene glycol monomethyl ether acetate

[0400] Leveling agent (F): Polyether-modified silicone oil (Toray Silicone SH8400 manufactured by Dow Corning Toray Co., Ltd.)

[0401] As shown in Table 2, the colored curable resin composition containing compound (I) had an excellent absorbance retention rate before and after the heat resistance test.

Claims

1. A coloring composition comprising a colorant and a resin, wherein the colorant is any one of the compounds shown below, and the resin is an alkali-soluble resin.

2. A colored curable resin composition comprising the coloring composition according to claim 1, a polymerizable compound, and a polymerization initiator.

3. A color filter formed from the coloring composition according to claim 1.

4. A color filter formed from the colored curable resin composition according to claim 2.

5. A display device comprising the color filter according to claim 3 or 4.

Images