Compounds and coloring compositions

Abstract

The present invention provides a novel compound and a coloring composition. A compound represented by formula (I). [In formula (I), Q represents formula (Q1): *-CR 6 =CR 5 -NR 3 -**、Formula (Q2): *-O-CR 5 =N-**, formula (Q3): *-S-CR 5 =N-**, formula (Q4): *-N=CR 5 -NR 3 -** or formula (Q5): *-NR 6 -CR 5 =N-** represents a group (* represents the same 4 The bonding site of the carbon atom to which it is bonded). 1 ~R 5 Each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, and the -CH2- contained in the hydrocarbon group may be substituted with -O- or -CO-. 6 It represents a monovalent aromatic group which may have a substituent or a monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, wherein -CH2- contained in the aliphatic 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] Various dyes are known as colorants contained in a colored resin composition forming a color filter included in a liquid crystal display device, a solid-state imaging element, etc. Patent Document 1 discloses a filter for a plasma display panel using a squarylium dye.

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: Japanese Patent Application Publication No. 2001-183522 Summary of the invention

[0006] An object of the present invention is to provide a compound having excellent absorbance retention before and after a light resistance test, a coloring composition containing the compound, a coloring 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 the following compounds, coloring compositions, coloring curable resin compositions, color filters, and display devices.

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

[0009]

[0010] [In formula (I),

[0011] Q expression (Q1): *-CR 6 =CR 5 -NR 3 -**、Formula (Q2): *-O-CR 5 =N-**, formula (Q3): *-S-CR 5 =N-**, formula (Q4): *-N=CR 5 -NR 3 -** or formula (Q5): *-NR 6 -CR 5 =N-** represents a group (* represents the same 4 The bonding site of the bonded carbon atom).

[0012] R 1 ~R 5 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 by -O- or -CO-.

[0013] R 6 It represents a monovalent aromatic group which may have a substituent or a monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, wherein -CH2- contained in the aliphatic hydrocarbon group may be substituted with -O- or -CO-.]

[0014] In addition, ** represents the bonding site on the other side of Q.

[0015] [2] A coloring composition comprising a resin and a coloring agent containing the compound described in [1] above.

[0016] [3] A colored curable resin composition comprising the colored composition described in [2] above, a polymerizable compound, and a polymerization initiator.

[0017] [4] A color filter formed from the colored composition described in [2] above or the colored curable resin composition described in [3] above.

[0018] [5] A display device comprising the color filter described in [4] above.

[0019] The coloring composition containing the compound of the present invention is excellent in absorbance retention before and after the light resistance test. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1 (a) and (b) are schematic cross-sectional views showing an example of an optical filter.

[0021] Figure 2 (a) is a schematic cross-sectional view showing an example of an organic EL display device using an optical filter, and (b) is a schematic cross-sectional view showing an example of a liquid crystal display device using an optical filter.

[0022] Explanation of symbols

[0023] 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

[0024] (Compound represented by formula (I))

[0025] The present invention relates to a compound represented by the following formula (I) (hereinafter, sometimes referred to as "compound (I)").

[0026]

[0027] [In formula (I), all symbols have the same meanings as above.]

[0028] In compound (I), when Q is a group represented by formula (Q1), compound (I) has the following structure.

[0029]

[0030] In compound (I), when Q is a group represented by formula (Q2), compound (I) has the following structure.

[0031]

[0032] In compound (I), when Q is a group represented by formula (Q3), compound (I) has the following structure.

[0033]

[0034] In compound (I), when Q is a group represented by formula (Q4), compound (I) has the following structure.

[0035]

[0036] In compound (I), when Q is a group represented by formula (Q5), compound (I) has the following structure.

[0037]

[0038] When compound (I) is used in a coloring composition described below, for example, it is excellent in the absorbance retention rate before and after a light resistance test. When compound (I) is used in a coloring composition, for example, it is also excellent in heat resistance.

[0039] In the case where Q is a group represented by the formula (Q1), in addition to the above-described structures, compound (I) also has tautomers of resonance structures represented by, for example, the following formulas.

[0040]

[0041] In the case where Q is a group represented by the formula (Q2), in addition to the above-described structures, there are also tautomers having resonance structures represented by, for example, the following formulas.

[0042]

[0043] In the case where Q is a group represented by the formula (Q3), in addition to the above-described structures, compound (I) also has tautomers having resonance structures represented by, for example, the following formulas.

[0044]

[0045] In the case where Q is a group represented by the formula (Q4), in addition to the above-described structures, compound (I) also has tautomers having resonance structures represented by, for example, the following formulas.

[0046]

[0047] In the case where Q is a group represented by the formula (Q5), in addition to the above-described structures, compound (I) also has tautomers having resonance structures represented by, for example, the following formulas.

[0048]

[0049] Compound (I) includes the above-exemplified tautomers and includes all tautomers.

[0050] The hydrocarbon group in formula (I) means 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 substituent.

[0051] The number of carbon atoms in a group after -CH2- contained in a hydrocarbon group is replaced by -O- or -CO- means the number of carbon atoms before the replacement by -O- or -CO-.

[0052] In formula (I), R 1 ~R 5 The monovalent hydrocarbon group having 1 to 6 carbon atoms in ] includes a monovalent aliphatic hydrocarbon group or a monovalent aromatic hydrocarbon group.

[0053] R 1 ~R 5 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.

[0054] As R 1 ~R 5 The monovalent aliphatic saturated hydrocarbon group in the group includes straight-chain alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl and hexyl; branched-chain alkyl groups having 3 to 6 carbon atoms, such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl and neopentyl; and alicyclic saturated hydrocarbon groups having 3 to 6 carbon atoms, such as cyclopropyl, cyclopentyl and cyclohexyl.

[0055] As R 1 ~R 5The monovalent aliphatic unsaturated hydrocarbon group in the alkyl group may include straight-chain alkenyl groups having 2 to 6 carbon atoms such as ethenyl, propenyl, butenyl, pentenyl and hexenyl; branched-chain alkenyl groups having 4 to 6 carbon atoms such as sec-butenyl and iso-butenyl; straight-chain alkynyl groups having 3 to 6 carbon atoms such as propynyl, n-butynyl, n-pentynyl and n-hexynyl; branched-chain alkynyl groups having 4 to 6 carbon atoms such as sec-butynyl and iso-butynyl; cycloalkenyl groups having 3 to 6 carbon atoms such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl; cycloalkynyl groups having 4 to 6 carbon atoms such as cyclobutynyl, cyclopentynyl and cyclohexynyl, etc.

[0056] R 1 ~R 5 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.

[0057] As R 1 ~R 5 The monovalent aromatic hydrocarbon group in includes phenyl.

[0058] In formula (I), R 1 ~R 5 The substituent that the hydrocarbon group in may have includes a halogen atom, a hydroxyl group, an amino group, a nitro group, a sulfamoyl group, a sulfo group and the like.

[0059] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0060] As R 1 ~R 5 The hydrocarbon group in may have a substituent, preferably a halogen atom.

[0061] In formula (I), -CH2- contained in the monovalent hydrocarbon group having 1 to 6 carbon atoms may be substituted with -O- or -CO-. Examples of such groups include -C(=O)CH3 and -C(=O)-OCH2CH3.

[0062] In formula (I), R 1 and R 2 Each of them independently is preferably a hydrogen atom or an alkyl group, and more preferably both are hydrogen atoms.

[0063] R 3 ~R 5 Each R is independently preferably a hydrogen atom or an alkyl group. 3 More preferably, it is a hydrogen atom, R 4 and R 5 More preferably, they are each independently an alkyl group.

[0064] In formula (I), R 6The monovalent aromatic group in may be a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group. The monovalent aromatic group may be a monocyclic structure or a condensed ring structure.

[0065] The monovalent aromatic hydrocarbon group has usually 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 13 carbon atoms.

[0066] Examples of the monovalent aromatic hydrocarbon group include aryl groups having 6 to 16 carbon atoms such as phenyl, methylphenyl, dimethylphenyl, mesityl, propylphenyl, butylphenyl, hexylphenyl, 2-ethylhexylphenyl, naphthyl, biphenyl, terphenyl, propylbiphenyl, anthracenyl, phenanthryl, pyrenyl, and fluorenyl; and aralkyl groups such as benzyl, phenethyl, phenylpropyl, and phenylbutyl.

[0067] The monovalent aromatic hydrocarbon group includes a group in which hydrogen bonded to a carbon of an aromatic ring constituting the aromatic hydrocarbon group is substituted with an alkyl group or an aryl group, and the -CH2- contained in the substituted alkyl group may be substituted with -O- or -CO-.

[0068] Composition R 6 The number of carbon atoms in the aromatic ring contained in the monovalent aromatic hydrocarbon group in is preferably 6-18, more preferably 6-12.

[0069] The monovalent aromatic heterocyclic group has usually 2 to 30 carbon atoms, preferably 4 to 20 carbon atoms, and more preferably 4 to 10 carbon atoms.

[0070] The hetero atom in the monovalent aromatic heterocyclic group represents a nitrogen atom, an oxygen atom, a sulfur atom, etc. The number of hetero atoms contained in the monovalent aromatic heterocyclic group is preferably 1 to 3, and more preferably 1.

[0071] Examples of the monovalent aromatic heterocyclic group include furan, thiophene, pyrrole, Azoles, Isopropylamine Azoles, thiazoles, isothiazoles, imidazoles, pyrazoles, furazans, triazoles, Oxadiazole, isocyanate oxazole, tetrazole, pyran, pyridine, thiopyran, pyridazine, pyrimidine, pyrazine, triazine, benzofuran, isobenzofuran, benzothiophene, indole, isoindole, indolizine, indoline, isoindoline, chromene, isochromene, chroman, isochroman, benzopyran, quinoline, isoquinoline, quinolizine, benzimidazole, benzothiazole, benzothiadiazole, indazole, naphthyridine, quinoxaline, quinazoline, quinazolidine, cinnoline, phthalazine, porphyrin, pteridine, carbazole, xanthene, phenanthridine, acridine, β-carboline, phenanthridine, o-phenanthroline, thianthrene, phenanthroline Thiophene A group obtained by removing one hydrogen atom from a heterocyclic compound such as oxazine, phenothiazine, or phenazine.

[0072] The monovalent aromatic heterocyclic group includes groups in which hydrogen contained in the above groups is substituted with a hydrocarbon group such as an alkyl group or an aryl group.

[0073] Composition R 6 The number of carbon atoms in the aromatic heterocyclic ring contained in the monovalent aromatic heterocyclic group in is preferably 6-18, more preferably 6-12.

[0074] In formula (I), R 6 The substituent that the aromatic group in may have includes a halogen atom, a hydroxyl group, an amino group, a nitro group, an aryloxy group, an arylcarbonyl group, an aryloxycarbonyl group, a carboxyl group, a carbamoyl group, a sulfamoyl group, a sulfo group and the like.

[0075] In formula (I), R 6 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.

[0076] R 6 The number of carbon atoms of the monovalent aliphatic hydrocarbon group is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10, and further preferably 1 to 6. When the monovalent aliphatic hydrocarbon group contains a cyclic structure, the number of carbon atoms constituting the cyclic structure is preferably 3 to 6, more preferably 5 or 6.

[0077] R 6 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.

[0078] As R 6 The monovalent aliphatic saturated hydrocarbon group in the group includes straight-chain alkyl groups having 1 to 16 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl; branched-chain 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; cycloalkylalkyl groups having 4 to 16 carbon atoms, such as cyclohexylbutyl and cyclohexyloctyl, etc.

[0079] As R 6The monovalent aliphatic unsaturated hydrocarbon group in the formula (I) includes straight-chain alkenyl groups having 2 to 16 carbon atoms, such as ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl and decenyl; branched alkenyl groups, such as sec-butenyl and isobutenyl; straight-chain alkynyl groups, such as propynyl, n-butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n-octenyl, n-nonynyl and n-decynyl; branched alkynyl groups, such as sec-butynyl and isobutynyl; cycloalkenyl groups, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl; alkenylcycloalkyl groups, such as propenylcyclohexyl and 1-decenylcyclohexyl; and cycloalkynyl groups, such as cyclobutynyl, cyclopentynyl and cyclohexynyl.

[0080] As R 6 The monovalent aliphatic unsaturated hydrocarbon group in the formula (I) includes straight-chain alkenyl groups having 2 to 16 carbon atoms, such as ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl and decenyl; branched alkenyl groups, such as sec-butenyl and isobutenyl; straight-chain alkynyl groups, such as propynyl, n-butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n-octenyl, n-nonynyl and n-decynyl; branched alkynyl groups, such as sec-butynyl and isobutynyl; cycloalkenyl groups, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl; alkenylcycloalkyl groups, such as propenylcyclohexyl and 1-decenylcyclohexyl; and cycloalkynyl groups, such as cyclobutynyl, cyclopentynyl and cyclohexynyl.

[0081] R 6 When the monovalent aliphatic hydrocarbon group includes a cyclic structure, the number of carbon atoms constituting the cyclic structure is preferably 3 to 8, more preferably 4 to 6.

[0082] In formula (I), R 6 The aliphatic hydrocarbon group in the formula (a) may have a substituent, for example, R 1 ~R 5 The substituents exemplified in .

[0083] As R 6 The hydrocarbon group in may have a substituent, preferably a halogen atom.

[0084] R 6 -CH2- contained in the aliphatic hydrocarbon group in may be substituted with -O- or -CO-. Examples of such a group include -C(=O)CH3 and -C(=O)-OCH2CH3.

[0085] Examples of the compound (I) include compounds represented by the following formula.

[0086]

[0087]

[0088]

[0089] (Method for producing compound (I) (1))

[0090] The compound (I) of the present invention can be obtained by first reacting a compound represented by the following formula (IV-1) (hereinafter, sometimes referred to as "compound (IV-1)") with a compound represented by the following formula (IV-2) (hereinafter, sometimes referred to as "compound (IV-2)") to obtain a compound represented by the following formula (IV-3) (hereinafter, sometimes referred to as "compound (IV-3)"), and obtaining a compound represented by the following formula (IV-4) (hereinafter, sometimes referred to as "compound (IV-4)") from the compound (IV-3). Next, the compound (IV-4) is reacted with a compound represented by the following formula (IV-5) (hereinafter, sometimes referred to as "compound (IV-5)") to produce compound (I).

[0091]

[0092] [In formula (IV-1) and formula (IV-3), R 7 and R 8 Each independently represents an alkoxy group having 1 to 20 carbon atoms.

[0093] In formula (IV-2), formula (IV-3) and formula (IV-4), R 3 ~R 6 Means the same as above.

[0094] In formula (IV-5), R 1 and R 2 Means the same as above.]

[0095] In formula (IV-1) and formula (IV-3), R 7 and R 8 The alkoxy group having 1 to 20 carbon atoms includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, isopentoxy, neopentoxy, n-hexyloxy, n-cyclohexyloxy and n-dodecyloxy.

[0096] Examples of the compound (IV-1) include compounds represented by the following formula.

[0097]

[0098] Examples of the compound (IV-2) include compounds represented by the following formula.

[0099]

[0100] Examples of the compound (IV-3) include compounds represented by the following formula.

[0101]

[0102] Examples of the compound (IV-4) include compounds represented by the following formula.

[0103]

[0104] Examples of the compound (IV-5) include compounds represented by the following formula.

[0105]

[0106] In the step of producing compound (IV-3), compound (IV-1) and compound (IV-2) are preferably reacted in an organic solvent.

[0107] Examples of the organic solvent include aromatic hydrocarbon solvents such as toluene and xylene; hydrocarbon solvents such as hexane, cyclohexane, and decalin; tetrahydrofuran, 1,4-dihydronaphthalene, Ether solvents such as alkane and dimethoxyethane; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and chloroform; alcohol solvents such as methanol, ethanol, isopropanol, and butanol; nitro hydrocarbon 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 they can also be used in combination. Among them, butanol is preferred. The amount of the organic solvent used is preferably 5 to 100 parts by mass, and more preferably 10 to 50 parts by mass, relative to 1 part by mass of compound (IV-1).

[0108] The amount of compound (IV-2) used in the step of producing compound (IV-3) is preferably 0.7 mol to 3 mol, more preferably 1 mol to 2 mol, based on 1 mol of compound (IV-1).

[0109] The reaction temperature is preferably 30° C. to 180° C., more preferably 80° C. to 140° C. The reaction time is preferably 0.5 hour to 10 hours, more preferably 1 hour to 5 hours.

[0110] In the step of producing compound (IV-4), compound (IV-3) is preferably refluxed in an acidic aqueous solution using hydrochloric acid, acetic acid or the like.

[0111] The reaction temperature is preferably 30° C. to 180° C., more preferably 80° C. to 140° C. The reaction time is preferably 0.5 hour to 10 hours, more preferably 1 hour to 5 hours.

[0112] In the step of producing compound (I), it is preferred to react compound (IV-4) and compound (IV-5) in an organic solvent from the viewpoint of yield.

[0113] The organic solvent may be any of the organic solvents exemplified above, and a mixed solvent of butanol and toluene is preferred. The amount of the organic solvent used is preferably 10 to 200 parts by mass, more preferably 20 to 160 parts by mass, relative to 1 part by mass of the total of compound (IV-4) and compound (IV-5).

[0114] The amount of compound (IV-5) used in the step of producing compound (I) is preferably 0.7 mol to 3 mol, more preferably 1 mol to 2 mol, based on 1 mol of compound (IV-4).

[0115] The reaction temperature is preferably 30° C. to 180° C., more preferably 80° C. to 140° C. The reaction time is preferably 0.5 hour to 10 hours, more preferably 1 hour to 5 hours.

[0116] 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 used. For example, a method of filtering out 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 be performed using known methods such as recrystallization and column chromatography as needed.

[0117] (Method for producing compound (I) (2))

[0118] The compound (I) of the present invention can be produced by reacting the compound (IV-2), the compound (IV-5) and squaric acid (3,4-dihydroxy-3-cyclobutene-1,2-dione) represented by the following formula (IV-6).

[0119]

[0120] As compound (IV-2) and compound (IV-5), the compounds described above can be used.

[0121] In the step of producing compound (I), a method of subjecting compound (IV-2), compound (IV-5) and squaric acid to dehydration condensation in an organic solvent is preferably used from the viewpoint of yield.

[0122] The organic solvent may be any of the organic solvents exemplified above, and a mixed solvent of butanol and toluene is preferred. The amount of the organic solvent used is preferably 10 to 200 parts by mass, more preferably 20 to 160 parts by mass, relative to 1 part by mass of the total of compound (IV-4) and compound (IV-5).

[0123] The amount of squaric acid used in the step of producing compound (I) is preferably 0.45 mol to 0.6 mol, more preferably 0.47 mol to 0.55 mol, based on 1 mol of the total of compound (IV-2) and compound (IV-5).

[0124] 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.

[0125] The method for obtaining the target compound (I) from the reaction mixture is not particularly limited, and various known methods can be employed, and examples thereof include the above-mentioned methods.

[0126] (Coloring composition)

[0127] The coloring composition of the present invention comprises a coloring agent (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 the components may be used alone or in combination unless otherwise specified.

[0128] The coloring composition of the present invention is excellent in absorbance retention before and after a light resistance test. The coloring composition is also excellent in heat resistance.

[0129] (Colorant (A))

[0130] The coloring agent (A) contained in the coloring composition may contain other dyes as dye (A1) in addition to compound (I). As such dyes, dyes such as oil-soluble dyes, acid dyes, amine salts of acid dyes, sulfonamide derivatives of acid dyes may be cited, for example, compounds classified as solvents, acidic, alkaline, reactive, direct, dispersed, mordant or reduced dyes in the color index (published by The Society of Dyers and Colourists), and known dyes recorded in the dyeing notes (color dyeing company). In addition, according to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes and phthalocyanine dyes may be cited. These dyes may be used alone or in combination of two or more.

[0131] Specifically, CI Solvent Yellow 4 (hereinafter, CI Solvent Yellow is omitted and only the number is described), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;

[0132] CI Solvent Orange 2, 7, 11, 15, 26, 56;

[0133] CI 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;

[0134] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0135] CI 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;

[0136] CI Solvent Green 1,3,5,28,29,32,33; etc. CI solvent dyes,

[0137] CI 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, 156 7, 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;

[0138] CI 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;

[0139] CI Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;

[0140] CI Acid Green 3, 5, 9, 25, 27, 28, 41;

[0141] CI Acid Violet 34, 120;

[0142] CI acid blue 25, 27, 40, 45, 78, 80, 112; etc. CI acid dyes, CI basic green 1; etc. CI basic dyes,

[0143] CI Reactive Yellow 2, 76, 116;

[0144] CI reactive dyes such as CI reactive orange 16;

[0145] CI 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;

[0146] CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0147] CI Direct Blue 40; etc. CI direct dyes,

[0148] CI Disperse Yellow 51, 54, 76;

[0149] CI Disperse Violet 26, 27;

[0150] CI disperse blue 1, 14, 56, 60; etc. CI disperse dyes,

[0151] As CI mordant dyes, CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0152] CI 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. CI Mordant Dyes,

[0153] CI vat dyes such as CI vat Green 1, etc.

[0154] In the dye (A1), the content of the compound (I) is preferably 3 to 100 parts by mass, more preferably 10 to 70 parts by mass, and further preferably 15 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 prepared, and there is a tendency to facilitate film formation.

[0155] The coloring agent (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 Color Index (published by The Society of Dyers and Colourists) can be cited, and these can be used alone or in combination of two or more.

[0156] Examples of the pigment (A2) include yellow pigments such as CI 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, and 214;

[0157] CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;

[0158] CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 and other red pigments;

[0159] Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 60, etc.;

[0160] CI Pigment Violet 1, 19, 23, 29, 32, 36, 38, etc. purple pigments;

[0161] CI Pigment Green 7, 36, 58 and other green pigments;

[0162] Brown pigments such as CI Pigment Brown 23, 25, etc.; and

[0163] Black pigments such as CI Pigment Black 1, 7, etc.

[0164] As the pigment (A2), yellow pigments such as CI 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, and green pigments such as CI Pigment Green 7, 36, and 58 are preferred, CI Pigment Yellow 138, 150, 185, and CI Pigment Green 58 are more preferred, and CI Pigment Yellow 138 and CI Pigment Green 58 are further preferred. By containing the above pigments, the transmission spectrum can be easily optimized, and the light resistance and chemical resistance of the color filter can be improved.

[0165] The pigment may be subjected to rosin treatment, surface treatment using a pigment derivative into which an acidic group or a basic group is introduced, grafting treatment on the pigment surface using a polymer compound, micronization treatment using a sulfuric acid micronization method, or a washing treatment using an organic solvent or water to remove impurities, or removal treatment of ionic impurities using an ion exchange method.

[0166] The pigment preferably has a uniform particle size. By containing a pigment dispersant and performing a dispersion treatment, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained.

[0167] As the pigment dispersant, for example, a surfactant can be mentioned, which can be any surfactant of a cationic, anionic, nonionic, or amphoteric type. Specifically, surfactants such as polyester, polyamine, and acrylic acid can be mentioned. These pigment dispersants can be used alone or in combination of two or more. As the pigment dispersant, in terms of trade name, KP (Shin-Etsu Chemical Industry (Strain) system), FLOWLEN (Kyoeisha Chemical (Strain) system), Solsperse (registered trademark) (Zeneca (Strain) system), EFKA (registered trademark) (BASF company system), AJISPER (registered trademark) (Ajinomoto Fine-Techno (Strain) system), Disperbyk (registered trademark) (BYK company system), etc. can be mentioned.

[0168] When a pigment dispersant is used, its usage amount is preferably 1 to 100 parts by mass, more preferably 5 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 in a uniform dispersed state.

[0169] When the pigment (A2) is contained, the content ratio of the dye (A1) to the pigment (A2) in the colorant (A) is usually 45:55 to 1:99, preferably 40:60 to 2:98, and more preferably 38:62 to 3:97 on a mass basis.

[0170] The content of the colorant (A) is preferably 5 to 60 parts by mass, more preferably 8 to 55 parts by mass, and further preferably 10 to 50 parts by mass relative to 100 parts by mass of the solid content of the coloring composition. If the content of the colorant (A) is within the above range, the color concentration when the color filter is made is sufficient, and the coloring composition can contain the required amount of resin (B), etc., so there is a tendency to be easy to film. Here, the "solid component" in this specification refers to the substance after the solvent is removed from the coloring composition. The total amount of solid components and the content of each component relative to the total amount of solid components can be measured, for example, using known analytical methods such as liquid chromatography or gas chromatography.

[0171] (Resin (B))

[0172] The resin (B) contained in the coloring composition is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6].

[0173] 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 having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "(Bb)");

[0174] Resin [K2]: a copolymer of (Ba), (Bb) and a monomer (Bc) copolymerizable with (Ba) (which is different from (Ba) and (Bb)) (hereinafter, sometimes referred to as "(Bc)");

[0175] Resin [K3]: copolymer of (Ba) and (Bc);

[0176] Resin [K4]: a resin obtained by reacting a copolymer of (Ba) and (Bc) with (Bb);

[0177] Resin [K5]: a resin obtained by reacting a copolymer of (Bb) and (Bc) with (Ba);

[0178] Resin [K6]: A resin obtained by reacting a copolymer of (Bb) and (Bc) with (Ba) and further reacting with a carboxylic anhydride.

[0179] Specific examples of (Ba) include unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid;

[0180] 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.;

[0181] 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, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;

[0182] 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;

[0183] Unsaturated mono(meth)acryloyloxyalkyl) esters of polycarboxylic acids having a valence of 2 or more, such as mono(2-(meth)acryloyloxyethyl)succinate and mono(2-(meth)acryloyloxyethyl)phthalate;

[0184] Unsaturated (meth)acrylates containing a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymeth)acrylic acid, and the like.

[0185] Among them, (meth)acrylic acid, maleic anhydride, and the like are preferred from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an aqueous alkali solution.

[0186] (Bb) refers to a polymerizable compound having, for example, a cyclic ether structure having 2 to 4 carbon atoms (e.g., at least one selected from an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (Bb) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0187] In the present specification, "(meth)acrylic acid" means at least one of acrylic acid and methacrylic acid. The same applies to "(meth)acryloyl" and "(meth)acrylate".

[0188] Examples of (Bb) include a monomer having an ethylene oxide group and an ethylenically unsaturated bond, a monomer having an oxetane group and an ethylenically unsaturated bond, and a monomer having a tetrahydrofuranyl group and an ethylenically unsaturated bond.

[0189] (Bb) is preferably a monomer having an ethylene oxide group and an ethylenically unsaturated bond, since the obtained color filter can have higher reliability in terms of heat resistance, chemical resistance, etc.

[0190] 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, tricyclo[5.2.1.0](meth)acrylate, 2,6 ] decane-8-yl ester (in the technical field, it is commonly known as "dicyclopentanyl (meth)acrylate". It is also sometimes referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 ] (Meth)acrylates such as decen-8-yl (meth)acrylate (in the technical field, it is commonly referred to as "dicyclopentenyl (meth)acrylate"), dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;

[0191] (Meth)acrylates containing a hydroxyl group, such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

[0192] Diethyl maleate, diethyl fumarate, diethyl itaconate and other dicarboxylic acid diesters;

[0193] 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-dimethoxy Bicyclic unsaturated compounds such as 5-tert-butyloxycarbonylbicyclo[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-butyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;

[0194] Dicarbonyl imide 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, and N-(9-acridinyl)maleimide;

[0195] 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.

[0196] Among them, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and the like are preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0197] Specific examples of the resin (B) include 3,4-epoxycyclohexyl methyl (meth)acrylate / (meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 2.6] decyl acrylate / (meth)acrylic acid copolymer resins [K1]; (meth)acrylate glycidyl / (meth)acrylate benzyl / (meth)acrylic acid copolymer, (meth)acrylate glycidyl / 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 2.6 ] decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer / hydroxyl-containing (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer and other resins [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and other resins [K3]; benzyl (meth)acrylate / (meth)acrylic acid copolymer with glycidyl (meth)acrylate added thereto, tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer with glycidyl (meth)acrylate added thereto, Resins such as a resin in which glycidyl (meth)acrylate is added to a copolymer of tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid [K4]; a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid, and the like [K5]; a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid and further reacting it with tetrahydrophthalic anhydride, and the like [K6], and the like.

[0198] Among them, as the resin (B), the resin [K1] and the resin [K2] are preferred.

[0199] For example, the resin [K1] can be produced by referring to the method described in the document "Experimental Methods for Polymer Synthesis" (Otsu Takayuki, Kagaku Dojin, 1st edition, 1st print, published on March 1, 1972) and the cited documents described in the document.

[0200] It should be noted that the obtained copolymer can be used as a solution after the reaction, or a concentrated or diluted solution can be used, or a substance taken out in a solid (powder) form by a method such as reprecipitation can be used. In particular, during the polymerization, by using the solvent contained in the coloring composition of the present invention as a solvent, the solution after the reaction can be used directly to prepare the coloring composition of the present invention, so that the production process of the coloring composition of the present invention can be simplified.

[0201] The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3000 to 100000, more preferably 5000 to 50000, and even more preferably 5000 to 30000. When 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 portion in the developer is good, and there is a tendency for the resolution of the colored pattern to be improved.

[0202] The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1-6, more preferably 1.2-4.

[0203] The acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150, and even more preferably 70 to 135 mg-KOH / g. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration using a potassium hydroxide aqueous solution.

[0204] The content of the resin (B) is preferably 10 to 90 parts by mass, more preferably 20 to 85 parts by mass, and still more preferably 30 to 80 parts by mass relative to 100 parts by mass of the solid content. When the content of the resin (B) is within the above range, a colored pattern can be formed, and there is a tendency that the resolution and residual film rate of the colored pattern are improved.

[0205] (Solvent (E))

[0206] The solvent (E) that can be contained in the coloring composition is not particularly limited, and solvents commonly used in this field 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 cited.

[0207] 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, cyclohexanol acetate, and γ-butyrolactone.

[0208] 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-dihydrofuran, 1,4-di ... Alkane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether and methyl anisole, etc.

[0209] Examples of the ether ester solvent 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.

[0210] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0211] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0212] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0213] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0214] The solvent is preferably one solvent selected from the group consisting of 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, or a mixed solvent of two or more thereof; more preferably one solvent selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, N-methylpyrrolidone, N,N-dimethylformamide and tetrahydrofuran, or a mixed solvent of two or more thereof.

[0215] 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 content 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 becomes good, and the color concentration will not be insufficient when forming a color filter, so there is a tendency for the display characteristics to become good.

[0216] (Leveling agent (F))

[0217] As the leveling agent (F) which may be contained in the coloring composition, there are mentioned silicone-based surfactants, fluorine-based surfactants, silicone-based surfactants having fluorine atoms, etc. These may have a polymerizable group in the side chain.

[0218] Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule, and more 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 Co., Ltd.).

[0219] Examples of the fluorine-based surfactant include surfactants having a fluorine carbon chain in the molecule. Specific examples include FLUORAD (registered trademark) FC430 and 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, and MEGAFACE RS-718-K (manufactured by DIC Corporation), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, and Eftop EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, and Surflon SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Corporation). Fine Chemicals Research Institute) etc.

[0220] Examples of the organosilicon-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, and more specifically, MEGAFACE (registered trademark) R08, MEGAFACE BL20, MEGAFACE F475, MEGAFACE F477, and MEGAFACE F443 (manufactured by DIC Corporation).

[0221] The content of the leveling agent (F) is preferably 0.0001 to 0.2 parts by mass, more preferably 0.0002 to 0.1 parts by mass, and further preferably 0.0003 to 0.05 parts by mass relative 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 improved.

[0222] (Other ingredients in the coloring composition)

[0223] The coloring composition may contain additives known in the art, such as a filler, other polymer compounds, an adhesion promoter, an antioxidant, and a light stabilizer, as required.

[0224] (Method for producing coloring composition)

[0225] The coloring composition can be prepared by, for example, mixing the coloring agent (a), the resin (B), the solvent (E), the leveling agent (F), and other components as necessary.

[0226] The pigment (A2) is preferably mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size of the pigment is about 0.2 μm or less. At this time, a part or all of the above-mentioned pigment dispersant and resin (B) may be added as needed. By mixing the remaining components in the pigment dispersion thus obtained to a predetermined concentration, the target coloring composition can be prepared.

[0227] The dye may be dissolved in part or all of the solvent (E) to prepare a solution. The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

[0228] The mixed colored composition is preferably filtered through a filter having a pore size of about 0.1 to 10 μm.

[0229] (Colored curable resin composition)

[0230] The colored curable resin composition of the present invention comprises the above-mentioned colored composition, a polymerizable compound (C), and a polymerization initiator (D). The colored curable resin composition may further contain a polymerization initiation aid (D1).

[0231] The colored curable resin composition of the present invention can be expected to have excellent absorbance retention before and after a light resistance test. The colored curable resin composition can also be expected to have excellent heat resistance.

[0232] (Polymerizable compound (C))

[0233] The polymerizable compound (C) contained in the colored curable resin composition is a compound that can be polymerized by active radicals and / or acids generated by the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylate compounds.

[0234] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinyl pyrrolidone, and compounds having one ethylenically unsaturated bond such as the compounds exemplified as (Ba), (Bb), and (Bc) above;

[0235] Compounds having two 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;

[0236] Compounds having three ethylenically unsaturated bonds, such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and tris(2-(meth)acryloyloxyethyl)isocyanurate;

[0237] Compounds having four ethylenically unsaturated bonds such as pentaerythritol tetra(meth)acrylate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified pentaerythritol tetra(meth)acrylate;

[0238] Compounds having five ethylenically unsaturated bonds such as dipentaerythritol penta(meth)acrylate;

[0239] Compounds having six ethylenically unsaturated bonds such as dipentaerythritol hexa(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate;

[0240] Compounds having 7 or more ethylenically unsaturated bonds, such as tripentaerythritol hepta(meth)acrylate, tripentaerythritol octa(meth)acrylate, tetrapentaerythritol nona(meth)acrylate and tetrapentaerythritol deca(meth)acrylate; and the like.

[0241] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds, and more preferably a polymerizable compound having 5 to 6 ethylenically unsaturated bonds.

[0242] Among them, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are particularly preferred.

[0243] The weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.

[0244] 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 relative 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 color pattern formation and the chemical resistance of the color filter to be improved.

[0245] The content ratio of the resin (B) to the polymerizable compound (C) [resin (B):polymerizable compound (C)] is preferably 20:80 to 80:20, more preferably 35:65 to 80:20, based on mass.

[0246] (Polymerization initiator (D))

[0247] 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 free radicals, acids, etc. under the action of light or heat to initiate polymerization, and a known polymerization initiator can be used. Examples of polymerization initiators that generate active free radicals include O-acyl oxime compounds, alkyl phenone compounds, triazine compounds, acyl phosphine oxide compounds, and biimidazole compounds.

[0248] The O-acyl oxime compound is a compound having a partial structure represented by formula (Dd1).

[0249]

[0250] Examples of the O-acyl oxime compound include 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-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, and N-acetoxy-1-[1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine. -[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolanylmethoxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imide, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imide, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imide, etc. Commercially available products such as IRGACURE (registered trademark) OXE01, OXE02 (all manufactured by BASF), and 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 and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine. These O-acyl oxime compounds tend to provide a high brightness color filter.

[0251] The alkylphenone 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 a substituent.

[0252]

[0253] As the compound having a partial structure represented by formula (Dd2), for example, 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butane-1-one, etc. Commercially available products such as IRGACURE 369, 907, and 379 (all manufactured by BASF) can be used.

[0254] Examples of the compound having a partial structure represented by formula (Dd3) include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzil dimethyl ketal.

[0255] In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (Dd2).

[0256] 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-methoxyphenyl)-1,3,5-triazine, and 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.

[0257] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as IRGACURE (registered trademark) 819 (manufactured by BASF Corporation) can be used.

[0258] Examples of the biimidazole compound include compounds represented by the following formula (Dd4).

[0259]

[0260] [In formula (Dd4), R d1 ~R d5 represents an aryl group having 6 to 10 carbon atoms which may have a substituent.]

[0261] In formula (Dd4), as R d1 ~R d5 The aryl group having 6 to 10 carbon atoms in the group includes phenyl, methylphenyl, dimethylphenyl, ethylphenyl and naphthyl, and is preferably phenyl.

[0262] Examples of the substituent that the aryl group having 6 to 10 carbon atoms may have include a halogen atom and an alkoxy group having 1 to 4 carbon atoms. Examples of the halogen atom include R 1 ~R 4 The halogen atoms exemplified in. Examples of the alkoxy group having 1 to 4 carbon atoms include methoxy, ethoxy, propoxy and butoxy, and methoxy is preferred.

[0263] Specific examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Application Laid-Open Nos. 6-75372 and 6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, Biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carbonyl alkoxy groups (for example, see Japanese Patent Publication No. 7-10913). Among them, compounds represented by the following formulas and mixtures thereof are preferred.

[0264]

[0265] 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, and titanocene compounds, etc. These are preferably used in combination with the polymerization initiator aid (D1) (particularly amines) described later.

[0266] 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 toluenesulfonates; and benzoin toluenesulfonates.

[0267] The polymerization initiator (D) is preferably a polymerization initiator that generates active free radicals, more preferably a polymerization initiator containing at least one selected from an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyl oxime compound and a biimidazole compound, and still more preferably a polymerization initiator containing an O-acyl oxime compound.

[0268] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the content of the polymerization initiator (D) is within the above range, there is a tendency to increase sensitivity and shorten exposure time, thereby improving the productivity of the color filter.

[0269] (Polymerization initiator aid (D1))

[0270] The polymerization initiator aid (D1) that may be contained in the colored curable resin composition is a compound or sensitizer for accelerating the polymerization of the polymerizable compound initiated by the polymerization initiator. When the polymerization initiator aid (D1) is contained, it is usually used in combination with the polymerization initiator (D).

[0271] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0272] Examples of the amine compound include alkanolamines such as triethanolamine, methyldiethanolamine, and triisopropanolamine; aminobenzoic acid esters such as methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl 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; and the like. Among them, alkylaminobenzophenones are preferred, and 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used.

[0273] 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, and 2-ethyl-9,10-dibutoxyanthracene.

[0274] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0275] 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, and naphthoxyacetic acid.

[0276] When these polymerization initiator aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the amount of the polymerization initiator aid (D1) is within this range, a colored pattern can be formed with further high sensitivity, and there is a tendency that the productivity of the color filter is improved.

[0277] (Other components in the colored curable resin composition)

[0278] The colored curable resin composition may contain additives known in the technical field such as a chain transfer agent as necessary.

[0279] (Method for producing colored curable resin composition)

[0280] The colored curable resin composition can be prepared, for example, by mixing the colored composition with a polymerizable compound (C), a polymerization initiator (D), a polymerization initiator aid (D1) and other components. The colored curable resin composition is preferably used in the case of patterning by photolithography. The mixed colored curable resin composition is preferably filtered with a filter having a pore size of about 0.1 to 10 μm.

[0281] (Color filter and method of manufacturing the same)

[0282] The color filter of the present invention can be formed from the above-mentioned colored composition or colored curable resin composition. The color filter of the present invention is excellent in absorbance retention before and after a light resistance test. The color filter is also excellent in heat resistance.

[0283] As a method for manufacturing a color filter formed of a coloring composition or a coloring curable resin composition, for example, a method of applying the coloring composition or the coloring curable resin composition on a substrate, performing heating drying (pre-baking) and / or reduced pressure drying to remove volatile components such as a solvent and drying it to form a smooth composition layer, followed by post-baking, etc. The cured coating film thus formed can be the color filter of the present invention.

[0284] As the substrate, a glass plate such as quartz glass, borosilicate glass, aluminosilicate glass, soda-lime glass coated with silicon dioxide on the surface, a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, or a substrate on which a thin film of aluminum, silver, or a silver / copper / palladium alloy is formed can be used. Other color filter layers, resin layers, transistors, circuits, etc. can be formed on these substrates.

[0285] Examples of the coating method include spin coating, slit coating, and slit spin coating.

[0286] The temperature for heat drying is preferably 30 to 120° C., more preferably 50 to 110° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

[0287] When the reduced pressure drying is performed, it is preferably performed under a pressure of 50 to 150 Pa and a temperature range of 20 to 25°C.

[0288] The thickness of the composition layer formed by applying the colored composition or the colored curable resin composition is not particularly limited and can be appropriately selected depending on the film thickness of the target color filter.

[0289] The obtained composition layer is preferably further post-baked. 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.

[0290] The film thickness of the obtained color filter is not particularly limited and can be appropriately adjusted depending on the purpose, application, etc., and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

[0291] The cured coating film thus obtained may be patterned by, for example, etching.

[0292] The colored composition or colored curable resin composition of the present invention can also be used to manufacture a colored pattern using photolithography, inkjet method, printing method, etc. Among them, when using a colored curable resin composition containing a polymerizable compound (C) and a polymerization initiator (D), photolithography is preferred. Photolithography is a method in which a colored curable resin composition is applied to a substrate, dried to form a composition layer, and the composition layer is exposed via a photomask and developed. Coating and drying can be performed under the above conditions.

[0293] 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 application is used.

[0294] As the light source for exposure, a light source generating light with a wavelength of 250 to 450 nm is preferred. For example, a filter that cuts off the wavelength region may be used to cut off light below 350 nm, or a bandpass filter that extracts light in the wavelength region near 436 nm, near 408 nm, and near 365 nm may be used to selectively extract light in these wavelength regions. Specifically, mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, etc. may be cited.

[0295] It is preferable to use an exposure device such as a mask aligner and a stepper because it can uniformly irradiate the entire exposure surface with parallel light or accurately align the photomask and the substrate on which the composition layer is formed.

[0296] The exposed composition layer is brought into contact with a developer to develop the composition layer, thereby forming a colored 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, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. In addition, the developer may contain a surfactant.

[0297] The developing method may be any of a puddle method, a dipping method, a spray method, etc. In addition, during the development, the substrate may be tilted at any angle.

[0298] It is preferred to perform water washing after development.

[0299] The obtained colored pattern is preferably post-baked. The post-baking temperature and time may be the same as those described above.

[0300] The color filter is preferably used in a solid-state imaging element and a display device (for example, a liquid crystal display device, an organic EL device, electronic paper, etc.).

[0301] (Optical Filter)

[0302] Compound (I) can be used, for example, in an optical filter for a display device, etc. The optical filter can be expected to have excellent absorbance retention before and after a light resistance test, and can also be expected to have excellent heat resistance.

[0303] The optical filter is usually a layer formed of a composition containing a light-transmitting (preferably optically transparent) thermoplastic resin or thermosetting resin, and may be, for example, a film. The optical filter may have a layer containing compound (I) (hereinafter, sometimes referred to as "color correction layer"), and may be a color correction film composed of a single-layer structure of the color correction layer, or may be a laminate having a multilayer structure containing the color correction layer. When the optical filter has a multilayer structure, it may contain one color correction layer, or may contain two or more color correction layers, and the compound (I) contained in the two or more layers may be the same or different.

[0304] When the optical filter is a laminate, the color correction layer may be an adhesive layer or a resin layer other than the adhesive layer (hereinafter, sometimes referred to as a "resin layer"). When the color correction layer is an adhesive layer, the two layers contained in the optical filter can be bonded to each other, and the optical filter can also be bonded to other components such as an image display element. The adhesive layer may be an adhesive layer formed of an adhesive or an adhesive layer formed of an adhesive.

[0305] When the color correction layer is a single-layer optical filter (color correction film), or when it is a resin layer other than an adhesive layer in a multi-layer optical filter, the method for making the color correction film or resin layer contain compound (I) is not particularly limited. For example, the following methods can be used: [i] a method of kneading with a resin forming the color correction film or resin layer and heating to form a film; [ii] a method of dispersing or dissolving the resin forming the color correction film or resin layer or a monomer of the resin and compound (I) in an organic solvent and forming it into a film 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 applied to a resin substrate film to form a resin layer, and a film after peeling off the resin substrate film from the resin layer can also be used as a color correction film. The thickness of the color correction film and the resin layer is not particularly limited, and can be, for example, 1 μm to 200 μm.

[0306] When the color correction film or resin layer contains compound (I), the content thereof is not particularly limited. For example, the amount of compound (I) may 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 or resin layer. Alternatively, the amount of compound (I) may be 10 parts by mass or less, preferably 3 parts by mass or less, more preferably 0.5 parts by mass or less.

[0307] When the color correction layer is an adhesive layer, the method for making the adhesive layer contain compound (I) is not particularly limited, as long as compound (I) is added when preparing the adhesive composition or adhesive composition forming the adhesive layer. The thickness of the adhesive layer is not particularly limited, and can be, for example, 1 μm to 100 μm.

[0308] When the adhesive layer contains compound (I), its content is also not particularly limited. For example, the compound (I) can be 0.01 mass parts or more, preferably 0.02 mass parts or more, more preferably 0.05 mass parts or more, relative to 100 mass parts of the base polymer of the adhesive and / or binder contained in the adhesive layer, and can be 10 mass parts or less, preferably 5 mass parts or less, more preferably 0.5 mass parts or less.

[0309] 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 attached to the visible side of the image display element of the display device for use. 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 compound (I).

[0310] When the optical filter is a laminate, its laminate structure is not particularly limited, and may have, for example, Figure 1 The stacked structures shown in (a) and (b). Figure 1 (a) and (b) are schematic cross-sectional views showing an example of an optical filter. Figure 1 The optical filter 10 shown in (a) can be used in an organic EL display device. The optical filter 10 may include, for example, an adhesive layer 11 for an image display element, a phase difference film 12, an adhesive layer 13, a first protective film 14, a polarizing film 15, and a second protective film 16 in this order. The adhesive layer 11 for an image display element and the adhesive layer 13 are both equivalent to the above-mentioned adhesive layer, and the phase difference film 12, the first protective film 14, the polarizing film 15, and the second protective film 16 are all equivalent to the above-mentioned resin layer.

[0311] The first protective film 14, the polarizing film 15, and the second protective film 16 in the optical filter 10 form a polarizing plate, and the first protective film 14 and the second protective film 16 may have an adhesive layer on the side of the bonding surface with the polarizing film 15. The adhesive layer 11 for image display element is used to bond to the light-emitting layer of the organic EL element including the image display element as the organic EL display device. An unillustrated spacer (peeling film) may be provided on the surface of the adhesive layer 11 for image display element on the side opposite to the phase difference film 12.

[0312] Figure 1 The optical filter 20 shown in (b) can be used in a liquid crystal display device. The optical filter 20 may 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 in this order. The adhesive layer 21 for an image display element is equivalent to the above-mentioned adhesive layer, and the first protective film 24, the polarizing film 25, and the second protective film 26 are all equivalent to the above-mentioned resin layer.

[0313] The first protective film 24, the polarizing film 25 and the second protective film 26 in the optical filter 20 form a polarizing plate, and the first protective film 24 and the second protective film 26 may have an adhesive layer on the side of the bonding surface with the polarizing film 25. The adhesive layer 21 for image display element is used to be bonded to the liquid crystal cell of the image display element of the liquid crystal display device. A separator (release film) not shown in the figure may be provided on the surface of the adhesive layer 21 for image display element on the side opposite to the first protective film 24.

[0314] Can be formed Figure 1 In the optical filters 10 and 20 shown in (a) and (b), at least one of the resin layer and the adhesive layer contains the compound (I). Figure 1 In the optical filter 10 shown in (a), the compound (I) may be contained in at least one of the pressure-sensitive adhesive layer 11 for an image display element, the pressure-sensitive adhesive layer 13 , the first protective film 14 , and the second protective film 16 . Figure 1 In the optical filter 20 shown in (b) in FIG. 1 , the compound (I) may be contained in at least one of the pressure-sensitive adhesive layer 21 for an image display element, the first protective film 24 , and the second protective film 26 .

[0315] Figure 1 The optical filters 10 and 20 shown in (a) and (b) are merely examples, and may have a laminated structure other than the above. For example, the second protective film 16, 26 may have other layers such as a film with an anti-glare function and a film with a surface anti-reflection function on the surface opposite to the polarizing film 15, 25. In addition, the first protective film 14, 24 may function as a phase difference film, and the second protective film 16, 26 may have an anti-glare function, a surface anti-reflection function, a function as a phase difference film, etc. In addition, in addition to forming Figure 1 In addition to the layers of the optical filters 10 and 20 shown in (a) and (b) above, a color correction layer containing the compound (I) may be provided at an arbitrary position.

[0316] Since the optical filter contains the compound (I), it can be expected that the optical filter has excellent absorbance retention before and after the light resistance test. The optical filter can also be expected to have excellent heat resistance.

[0317] Hereinafter, each component constituting the optical filter will be described in detail.

[0318] (Adhesive layer)

[0319] As adhesives that can be used for the adhesive layer, for example, water-based adhesives, active energy ray-curable adhesives, and combinations thereof can be cited. As water-based adhesives, for example, polyvinyl alcohol resin aqueous solutions, water-based two-component polyurethane emulsion adhesives, etc. can be cited. Active energy ray-curable adhesives refer to adhesives that are cured by irradiating active energy rays such as ultraviolet rays, and for example, adhesives containing polymerizable compounds and photopolymerization initiators, adhesives containing photoreactive resins, adhesives containing binder resins and photoreactive crosslinking agents can be cited. As the above-mentioned polymerizable compounds, photopolymerizable monomers such as photocurable epoxy monomers, photocurable (meth) acrylic monomers, and photocurable polyurethane monomers, oligomers from these monomers, etc. can be cited. As the above-mentioned photopolymerization initiator, a photopolymerization initiator containing active species such as neutral free radicals, anionic free radicals, and cationic free radicals generated by irradiating active energy rays such as ultraviolet rays can be cited.

[0320] As the adhesive that can be used for the adhesive layer, a known adhesive in the past can be used. As the adhesive, for example, (meth) acrylic adhesive, polyurethane adhesive, silicone adhesive, polyester adhesive, polyamide adhesive, polyether adhesive, fluorine adhesive, rubber adhesive etc. can be mentioned. In addition, it can be energy ray curing adhesive, thermosetting adhesive etc. Wherein, from the viewpoints such as transparency, bonding strength, reliability, it is preferred to use (meth) acrylic adhesive.

[0321] The (meth)acrylic adhesive is not particularly limited, and is a polymer with (meth)acrylate as the main component (containing 50% by mass or more), which may be a homopolymer of one (meth)acrylate, or a copolymer of (meth)acrylate and other (meth)acrylates. As (meth)acrylates, butyl (meth)acrylate, ethyl (meth)acrylate, methyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and 2-phenoxyethyl (meth)acrylate may be cited. In addition, a polar monomer may be copolymerized in the polymer with these (meth)acrylates as the main component. As polar monomers, for example, monomers having polar functional groups such as carboxyl, hydroxyl, amide, amino, and epoxy groups may be cited, 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 resin used in the (meth)acrylic adhesive has a weight average molecular weight (Mw) of 100,000 or more, preferably 600,000 or more, and usually 2,500,000 or less.

[0322] These (meth) acrylic adhesives can also be used alone, usually in combination with a crosslinking agent. Examples of the crosslinking agent include: bivalent or polyvalent metal ions that form carboxylic acid metal salts 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. Among them, isocyanate compounds are preferably used.

[0323] Among the isocyanate compounds, it is preferred to use meta-xylylene diisocyanate, toluene diisocyanate or hexamethylene diisocyanate; adducts obtained by reacting polyols such as glycerol and trimethylolpropane with these isocyanate compounds; substances in which these isocyanate compounds are formed into dimers, trimers, etc. or mixtures thereof; mixtures of two or more of the isocyanate compounds listed above, etc.

[0324] Preferred isocyanate compounds include toluene diisocyanate, an adduct obtained by reacting a polyol with toluene diisocyanate, a dimer of toluene diisocyanate, a trimer of toluene diisocyanate, hexamethylene diisocyanate, an adduct obtained by reacting a polyol with hexamethylene diisocyanate, a dimer of hexamethylene diisocyanate, and a trimer of hexamethylene diisocyanate.

[0325] The content of the crosslinking agent in the acrylic pressure-sensitive adhesive is usually 0 to 5 parts by mass, preferably 0.05 to 2 parts by mass, relative to 100 parts by mass of the (meth)acrylic resin.

[0326] The acrylic adhesive may further contain a silane compound. When the acrylic adhesive contains a silane compound, the adhesion between the obtained adhesive layer and an optical member such as a glass substrate can be improved.

[0327] Examples of the silane compound include vinyl trimethoxysilane, vinyl triethoxysilane, vinyl tri(2-methoxyethoxy)silane, 3-aminopropyl triethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-glycidoxypropyl methyl dimethoxysilane, 3-chloropropyl methyl dimethoxysilane, 3-chloropropyl trimethoxysilane, 3-methacryloxypropyl trimethoxysilane, 3-mercaptopropyl trimethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-glycidoxypropyl triethoxysilane, 3-glycidoxypropyl dimethoxymethylsilane, and 3-glycidoxypropyl ethoxy dimethylsilane. Two or more silane compounds may be used.

[0328] The silane compound may be a silicone oligomer type silane compound. When the silicone oligomer is represented in the form of a (monomer) oligomer, for example, 3-mercaptopropyltrimethoxysilane-tetramethoxysilane copolymer, mercaptomethyltrimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-methacryloxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-acryloxypropyltrimethoxysilane-tetramethoxysilane copolymer, vinyltrimethoxysilane-tetramethoxysilane copolymer, etc. may be cited.

[0329] The content of the silane compound in the adhesive composition is generally 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, and more preferably 0.1 to 2 parts by mass, relative to 100 parts by mass of (meth) acrylic resin. If the content of the silane compound is more than 0.01 parts by mass, it is easy to obtain an effect of improving the adhesion of optical components such as an adhesive layer and a glass substrate. In addition, if the content of the silane compound is less than 10 parts by mass, it is possible to suppress the oozing out of the silane compound from the adhesive layer.

[0330] The acrylic adhesive may further contain an ionic compound as an antistatic agent for imparting antistatic properties. An ionic compound is a compound having an inorganic cation or an organic cation and an inorganic anion or an organic anion. The acrylic adhesive may contain two or more ionic compounds.

[0331] Examples of inorganic cations include lithium cations [Li + 〕、Sodium cation〔Na + 〕、Potassium cation〔K + 〕Alkali metal ions, beryllium cations〔Be 2+ 〕、Magnesium cation〔Mg 2+ 〕、Calcium cation〔Ca 2+ 〕and other alkaline earth metal ions, etc.

[0332] Examples of the organic cation include an imidazolium cation, a pyridinium cation, a pyrrolidinium cation, an ammonium cation, a sulfonium cation, and a phosphonium cation.

[0333] Examples of inorganic anions include chloride ions [Cl － 〕、Br － 〕、Iodide ion〔I － 〕、Tetrachloroaluminate anion〔AlCl4 － 〕、heptachlorodialuminate anion〔Al2Cl7 － 〕、Tetrafluoroborate anion〔BF4 － 〕、Hexafluorophosphate anion〔PF6 － 〕、Perchlorate anion〔ClO4 － 〕、nitrate anion〔NO3 － 〕、Hexafluoroarsenate anion〔AsF6 － 〕、Hexafluoroantimonate anion〔SbF6 － 〕、Hexafluoroniobate anion〔NbF6 － 〕、Hexafluorotantalate anion〔TaF6 － 〕、Dicyanamide anion〔(CN)2N － 〕wait.

[0334] As the organic anion, for example, acetate anion [CH3COO － 〕、Trifluoroacetate anion〔CF3COO － 〕、Methanesulfonate anion 〔CH3SO3 － 〕、Trifluoromethanesulfonate anion〔CF3SO3 － 〕、p-toluenesulfonate anion〔p-CH3C6H4SO3 － 〕、bis(fluorosulfonyl)imide anion〔(FSO2)2N-〕、bis(trifluoromethanesulfonyl)imide anion〔(CF3SO2)2N-〕、tris(trifluoromethanesulfonyl)methylated anion〔(CF3SO2)3C-〕、dimethylphosphinate anion〔(CH3)2POO-〕、(poly)hydrofluoride anion〔F(HF) n-〕(n is about 1 to 3), thiocyanate anion〔SCN-〕, perfluorobutanesulfonate anion〔C4F9SO3-〕, bis(pentafluoroethanesulfonyl)imide anion〔(C2F5SO2)2N － 〕、Perfluorobutyrate anion〔C3F7COO － 〕、(trifluoromethanesulfonyl)(trifluoromethanecarbonyl)imide anion〔(CF3SO2)(CF3CO)N － 〕wait.

[0335] Specific examples of the ionic compound can be selected from the combination of the above-mentioned cationic components and anionic components.

[0336] 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(fluorosulfonyl)imide, N-hexylpyridinium bis(trifluoromethanesulfonyl)imide, and N-octylpyridinium bis(trifluoromethanesulfonyl)imide, 1-ethyl-3-methylimidazolium hexafluorophosphate, and 1-ethyl-3-methylimidazolium p-toluenesulfonate. , imidazolium salts such as 1-ethyl-3-methylimidazolium bis(fluorosulfonyl)imide, 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, and 1-butyl-3-methylimidazolium methanesulfonate; pyrrolidinium salts such as N-butyl-N-methylpyrrolidinium hexafluorophosphate, N-butyl-N-methylpyrrolidinium bis(fluorosulfonyl)imide, and N-butyl-N-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide; quaternary ammonium salts such as tetrabutylammonium hexafluorophosphate and tetrabutylammonium p-toluenesulfonate.

[0337] Examples of the ionic compound having an inorganic cation include lithium bromide, lithium iodide, and sodium hexafluorophosphate.

[0338] From the viewpoint of maintaining antistatic performance, the ionic compound is preferably solid at room temperature. The ionic compound preferably has a melting point of 30° C. or higher, and further preferably has a melting point of 35° C. or higher. On the other hand, if its melting point is too high, the compatibility with the (meth)acrylic resin deteriorates, so 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.

[0339] 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, relative to 100 parts by mass of the (meth)acrylic resin. A content of the ionic compound of 0.1 parts by mass or more is beneficial to improving the antistatic performance, and a content of 8 parts by mass or less is beneficial to maintaining the durability of the adhesive layer.

[0340] Various additives may be further added to the adhesive or pressure-sensitive adhesive, such as a rework agent, an adhesiveness-imparting resin, an antioxidant, an ultraviolet light absorber, a defoaming agent, a corrosive agent, and a light diffusing agent such as fine particles.

[0341] (Resin layer)

[0342] As the resin layer, there can be cited polarizing films as linear polarizers; protective films provided for protecting the surface of polarizing films, etc.; phase difference films; optical compensation films other than phase difference films; films with anti-glare functions and surface anti-reflection functions having concave-convex shapes; reflective films with reflective functions on the surface; semi-transmissive reflective films having both reflective and transmissive functions; light diffusion films; hard coating films; color correction films, etc. The optical filter may include one or more of the above resin layers.

[0343] Examples of the polarizing film include a polarizing film in which iodine is oriented in a polyvinyl alcohol-based resin layer, and a polarizing film in which a liquid crystal compound and a dichroic dye are oriented.

[0344] The resin layer is not particularly limited to materials other than polarizing films, and examples thereof include polyolefin resins such as chain polyolefin resins (polyethylene resins, polypropylene resins, etc.), cyclic polyolefin resins (norbornene resins, etc.); cellulose ester resins such as triacetyl cellulose, diacetyl cellulose, and cellulose acetate propionate; polyester resins such as polyethylene terephthalate and polyethylene naphthalate; polycarbonate resins; (meth)acrylic acid resins such as (meth)acrylic acid and polymethyl (meth)acrylate; vinyl alcohol resins such as polyvinyl alcohol and polyvinyl acetate; polystyrene resins; mixtures and copolymers thereof, etc. These resins may contain one or more additives such as lubricants, plasticizers, dispersants, heat stabilizers, ultraviolet absorbers, infrared absorbers, antistatic agents, antioxidants, light diffusers such as microparticles, etc.

[0345] (Display device)

[0346] The color filters and optical filters described above can be preferably used in display devices such as organic EL display devices, liquid crystal display devices, inorganic electroluminescent (inorganic EL) display devices, electron emission display devices, and electronic paper.

[0347] Figure 2 (a) and (b) are schematic cross-sectional views showing an example of a display device including an optical filter. Figure 2 The display device shown in (a) is a display device including Figure 1An organic EL display device including an optical filter 10 shown in (a) and an image display element 1 as a light-emitting layer of an organic EL element. The optical filter 10 can be arranged on the visible side of the image display element 1 via a pressure-sensitive adhesive layer 11 for an image display element.

[0348] Figure 2 The display device shown in (b) is a display device including Figure 1 The optical filter 20 shown in (b) and the liquid crystal display device of the image display element 2 as a liquid crystal cell including a liquid crystal layer. The optical filter 20 can be arranged on the visible side of the image display element 2 via the pressure-sensitive adhesive layer 21 for the image display element.

[0349] [Example]

[0350] The present invention will be described in more detail below with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples. "Parts" in Examples, Comparative Examples, Application Examples, and Comparative Application Examples are parts by mass unless otherwise specified.

[0351] [Identification of Compounds]

[0352] The structure of the compound was identified by mass spectrometry (LC; Model 1200 manufactured by Agilent, MASS; Model LC / MSD manufactured by Agilent).

[0353] [Example 1 (Compound (I))]

[0354] 25.00 parts (110.5 mmol) of 3,4-dibutoxy-3-cyclobutene-1,2-dione (manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the following formula (IV-1-a) and 82 parts (1.1 mol) of 1-butanol were heated and stirred at 110°C, and then 13.61 parts (110.5 mmol) of 3-ethyl-2,4-dimethylpyrrole (manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the following formula (IV-2-a) were added dropwise over 10 minutes, and heated under reflux for 3 hours. After the reaction, the mixture was cooled to room temperature. As a result, crystals were precipitated, so the solution was filtered to separate the precipitate. The precipitate was re-slurried with 500 mL of hexane, and a light green powder (compound represented by the following formula (IV-3-a)) was obtained.

[0355]

[0356] The powder obtained above was poured into an aqueous solution prepared with 12.6 mL of concentrated hydrochloric acid and 84.0 mL of distilled water using 110.0 mL of acetic acid, and heated under reflux at 110° C. for 2 hours. As a result, a color change from light green to light orange occurred, and the reaction was stopped. The reaction solution was cooled to room temperature, and the light orange powder was separated by filtration, and then re-slurried and washed with 500 mL of hexane, resulting in 18.34 parts (yield 75.7%) of a light yellow compound represented by the following formula (IV-4-a).

[0357]

[0358] 0.5 parts (2.3 mmol) of the compound represented by the obtained formula (IV-4-a), 0.32 parts (2.5 mmol) of phloroglucinol (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.8 parts of 1-butanol and 53 parts of toluene were mixed. The resulting mixture was removed with a Dean-Stark tube and stirred at a temperature of 110°C for 3 hours. After the reaction was completed, it was cooled to room temperature. As a result, a precipitate was obtained, so it was separated by filtration and reslurried and washed with 100 mL of hexane and 100 mL of methanol. As a result, 0.61 parts (yield 81%) of the compound represented by the following formula (A-1) (hereinafter sometimes referred to as "compound (A-1)") were obtained as a red powder. The obtained compound (A-1) was subjected to mass analysis.

[0359] (Mass analysis) Ionization mode = ESI+: m / z = [M+H] + 328.3

[0360] Exact Mass:327.1

[0361]

[0362] [Comparative Example 1]

[0363] 1 part (8.8 mmol) of 3,4-dihydroxy-3-cyclobutene-1,2-dione (squaric acid) represented by the following formula (IV-6) (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.), 2.16 parts (17.5 mmol) of 3-ethyl-2,4-dimethylpyrrole represented by the above formula (IV-2-a) (manufactured by Tokyo Chemical Industry Co., Ltd.), 33 parts (0.4 mol) of 1-butanol, and 55.2 parts (0.6 mol) of toluene were mixed. The resulting mixture was stirred at a temperature of 110° C. for 3 hours while removing the generated water using a Dean-Stark tube. The solvent in the reaction solution after the reaction was distilled off, 220 parts of ion exchange water was added, and the precipitated crude product was filtered out.

[0364]

[0365] The obtained crude product was separated from the compound represented by formula (B-1) (hereinafter sometimes referred to as "compound (B-1)") by column chromatography using silica gel (developing solvent: chloroform), and then dried under reduced pressure at 60°C for 12 hours to obtain 2.4 parts of compound (B-1). The obtained compound (B-1) was subjected to mass analysis.

[0366] (Mass analysis) Ionization mode = ESI+: m / z = [M+H] + 325.5

[0367] Exact Mass:324.2

[0368]

[0369] [Example 2 (coloring composition)]

[0370] (Synthesis of Resin (B1))

[0371] After replacing the atmosphere with nitrogen by flowing an appropriate amount of nitrogen into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added and heated to 85°C while stirring. Next, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ]dec-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 ] A mixed solution of 25 parts of a mixture of decyl-9-yl acrylate (content ratio of 1:1), 137 parts of cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate. 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 kept at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B1)) solution with a B-type viscosity (23°C) of 23 mPas and a solid content of 25.6%. The weight average molecular weight Mw of the generated copolymer was 8000, the solid content acid value was 111 mg-KOH / g, and the dispersion degree was 2.1. Resin (B1) has the following structural units.

[0372]

[0373] (Preparation of Coloring Composition)

[0374] The colored composition (a-1) is obtained by mixing the following components.

[0375]

[0376] (Production of color coating film)

[0377] The coloring composition (a-1) was applied to a 5 cm square glass substrate (EAGLE2000; manufactured by Corning) by spin coating, and then pre-baked at 100°C for 3 minutes to form a composition layer. Thereafter, the coloring composition (a-1) was post-baked in an oven at 230°C for 3 minutes to obtain a coloring coating film (a-1). The obtained coloring coating film (a-1) was subjected to a light resistance test. The results are shown in Table 1.

[0378] [Light resistance test]

[0379] An ultraviolet cut filter (COLORED OPTICAL GLASSL38, manufactured by HOYA Co., Ltd., cuts off light below 380 nm) was placed on the obtained colored coating film (a-1), and irradiated with xenon light for 24 hours using a light resistance tester (SUNTEST CPS+, manufactured by Toyo Seiki Co., Ltd.). The absorbance at the maximum absorption wavelength of the colored coating film (a-1) was measured before and after the light irradiation, and the absorbance after the light irradiation was calculated by taking the absorbance before the light irradiation as 100%. The maximum absorption wavelength of the colored coating film (a-1) is shown in Table 1.

[0380] [Heat resistance test]

[0381] The obtained colored coating film (a-1) was heated in an oven at 230°C for 20 minutes. The absorbance at the maximum absorption wavelength of the colored coating film (a-1) was measured before and after heating, and the absorbance before heating was taken as 100%, and the absorbance after heating was calculated. As a result, the absorbance of the colored coating film (a-1) after heat resistance was 72%.

[0382] [Comparative Example 2]

[0383] A colored composition (b-1) was obtained in the same manner as in Example 2 except that 0.10 parts of the compound (B-1) was used instead of the compound (A-1). A colored coating film (b-1) was obtained in the same manner as in Example 2 except that the colored composition (b-1) was used. A light resistance test was performed using the obtained colored coating film (b-1) in the same manner as in Example 2. The results are shown in Table 1.

[0384] [Table 1]

[0385]

[0386] As shown in Table 1, the coloring composition containing the compound (I) was excellent in the absorbance retention rate before and after the light resistance test.

Claims

1. A compound represented by formula (I), In formula (I), Q expression (Q1): *-CR 6 =CR 5 -NR 3 - A group represented by **, wherein * indicates the same as R 4 The bonding site of the bonded carbon atom, R 1 and R 2 represents a hydrogen atom, R 3 ~R 5 each independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group or a tert-butyl group, R 6 represents methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl or tert-butyl. 2 . A coloring composition comprising a colorant and a resin, wherein the colorant contains the compound according to claim 1 . 3 . A colored curable resin composition comprising the colored composition according to claim 2 , a polymerizable compound, and a polymerization initiator. 4 . A color filter formed from the colored composition according to claim 2 or the colored curable resin composition according to claim 3 .

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

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