Compound

Abstract

To provide a compound that reduces effluent treatment of a used developer in producing a colored pattern in a color filter in photolithography.SOLUTION: The invention provides a compound represented by the formula (I) in the figure. [In the formula, R3 to R10 are each independently H, a substituted / unsubstituted C1-C8 hydrocarbon group, or a halogen atom; a ring T1 is a heteroaromatic ring; R11, R14 and R15 are each independently a substituted / unsubstituted phenyl group; and R12 and R13 are each independently H or a substituted / unsubstituted C1-C20 hydrocarbon group; where -SO3- substitutes for one H atom included in the formula (I).]SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound useful as a colorant, a colored curable resin composition containing the compound, a color filter formed from the colored curable resin composition, and a display device including the color filter. [Background technology]

[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are produced from coloring compositions. A compound represented by formula (x) is known as a colorant used in such coloring compositions (Patent Document 1).

[0003] [ka] [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2018-127596 Summary of the Invention [Problem to be solved by the invention]

[0005] Photolithography is sometimes used to produce a colored pattern in a color filter from a coloring composition. In the photolithography method, a developer is brought into contact with a colored composition layer exposed through a photomask, and a portion of the colored composition layer is dissolved and removed to form a colored pattern. However, the developer containing the dissolved coloring composition usually requires wastewater treatment to reduce coloration, which places a burden on the process. Therefore, an object of the present invention is to provide a compound useful for reducing wastewater treatment of the developer. [Means for solving the problem]

[0006] The gist of the present invention is as follows. [1] A compound represented by formula (I): [ka] [In formula (I), R 3 ~R 10 each independently represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 8 carbon atoms, or a halogen atom. Ring T 1 represents an aromatic heterocycle. R 11 , R 14 and R 15 each independently represents a phenyl group which may have a substituent. R 12 and R 13 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. However, R 3 ~R 10 a substituent that may be possessed by the hydrocarbon group having 1 to 8 carbon atoms, represented by R 11 , R 14 and R 15 and R 12 and R 13 The substituents that the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have do not include -SO3M (wherein M represents a hydrogen ion, a metal ion, or an ammonium ion). -SO3 - replaces any one of the hydrogen atoms in formula (I). [2] Tamaki T 1 is a five-membered ring containing a nitrogen atom. [3] Tamaki T 1 is a thiazole ring or an oxazole ring. [4] A colored curable resin composition comprising a colorant containing the compound according to any one of [1] to [3], a resin, a polymerizable compound, a polymerization initiator, and a solvent. [5] A color filter formed from the colored curable resin composition according to [4]. [6] A display device comprising the color filter according to [5]. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a compound useful for reducing the wastewater treatment of a developer, that is, a compound excellent in the wastewater treatment of a developer. DETAILED DESCRIPTION OF THE INVENTION

[0008] <Compound> The compound of the present invention is a compound represented by formula (I) (hereinafter, may be referred to as compound (I)). Hereinafter, the present invention will be described in detail using formula (I), but compound (I) also includes tautomers of formula (I).

[0009] [ka] [In formula (I), R 3 ~R 10 each independently represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 8 carbon atoms, or a halogen atom. Ring T 1 represents an aromatic heterocycle. R 11 , R 14 and R 15 each independently represents a phenyl group which may have a substituent. R 12 and R 13 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. However, R 3 ~R 10 a substituent that may be possessed by the hydrocarbon group having 1 to 8 carbon atoms, represented by R 11 , R 14 and R 15 and R 12 and R 13The substituent that the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have is -SO3M(M represents hydrogen ions, metal ions, or ammonium ions). -SO3 - replaces any one of the hydrogen atoms in formula (I).

[0010] R 3 ~R 10 Examples of the hydrocarbon group having 1 to 8 carbon atoms represented by the formula (I) include aliphatic chain hydrocarbon groups having 1 to 8 carbon atoms, alicyclic hydrocarbon groups having 3 to 8 carbon atoms, aromatic hydrocarbon groups having 6 to 8 carbon atoms, and groups having 4 to 8 carbon atoms that are combinations of these.

[0011] The aliphatic chain hydrocarbon group may be saturated or unsaturated.

[0012] Examples of the saturated aliphatic chain hydrocarbon group (hereinafter sometimes referred to as alkyl group) include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, and octyl group; branched alkyl groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, and 2-ethylhexyl group; etc. The number of carbon atoms in the saturated aliphatic chain hydrocarbon group is 1 to 8, preferably 1 to 6, and more preferably 1 to 4.

[0013] Examples of the unsaturated aliphatic chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (e.g., 1-propenyl, 2-propenyl), and butenyl (e.g., 1-butenyl, 3-butenyl); and alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), and butynyl (e.g., 1-butynyl, 3-butynyl). The unsaturated aliphatic chain hydrocarbon group has 2 to 8 carbon atoms, preferably 2 to 6, and more preferably 2 to 4.

[0014] Examples of the alicyclic hydrocarbon group having 3 to 8 carbon atoms include a cyclopropyl group, a 1-methylcyclopropyl group, a cyclopentyl group, a cyclohexyl group, a 2-methylcyclohexyl group, etc. The alicyclic hydrocarbon group preferably has 3 to 7 carbon atoms.

[0015] Examples of the aromatic hydrocarbon group having 6 to 8 carbon atoms include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,4-dimethylphenyl group, and a 2,6-dimethylphenyl group.

[0016] Examples of the group having 4 to 8 carbon atoms formed by combining the above hydrocarbon groups include aralkyl groups such as benzyl, (4-methylphenyl)methyl, and phenethyl; and alkyl groups having an alicyclic hydrocarbon group bonded thereto, such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclohexylmethyl, and cyclohexylethyl.

[0017] R 3 ~R 10 The hydrocarbon group having 1 to 8 carbon atoms represented by the formula (I) is a saturated aliphatic group having 1 to 8 carbon atoms. It is preferably a chain hydrocarbon group, more preferably a saturated aliphatic chain hydrocarbon group having 1 to 4 carbon atoms, and even more preferably a linear alkyl group having 1 to 4 carbon atoms.

[0018] R 3 ~R 10 Examples of the substituent that the hydrocarbon group having 1 to 8 carbon atoms represented by the formula (I) may have include: Examples of such alkylsulfonyl groups include methylsulfonyl and ethylsulfonyl groups; alkylcarbonyl groups having 1 to 6 carbon atoms such as acetyl, propionyl, and butyryl groups; and alkoxycarbonyl groups having 1 to 6 carbon atoms such as methoxy and ethoxy groups.

[0019] R 3 ~R 10 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom and a chlorine atom are preferred, and a fluorine atom is more preferred.

[0020] Ring T 1 The aromatic heterocycle represented by the formula (I) may be a single ring or a condensed ring. 1 The number of carbon atoms in the aromatic heterocycle represented by the formula (I) is preferably 3 to 10, more preferably 3 to 8. The aromatic heterocycle is preferably a 5- to 10-membered ring, more preferably a 5- to 9-membered ring. Examples of monocyclic aromatic heterocycles include 5-membered rings containing no nitrogen atom, such as a pyrrole ring, an oxazole ring, a pyrazole ring, an imidazole ring, and a thiazole ring; 5-membered rings containing no nitrogen atom, such as a furan ring and a thiophene ring; and 6-membered rings containing a nitrogen atom, such as a pyridine ring, a pyrimidine ring, a pyridazine ring, and a pyrazine ring. Examples of fused aromatic heterocycles include fused rings containing a nitrogen atom, such as an indole ring, a benzimidazole ring, a benzothiazole ring, and a quinoline ring; and rings containing no nitrogen atom, such as a benzofuran ring.

[0021] R 11 , R 14 and R 15Examples of substituents that the phenyl group represented by the formula (I) may have include halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and hexyl; aromatic hydrocarbon groups having 6 to 8 carbon atoms such as phenyl, o-tolyl, m-tolyl, p-tolyl, 2,4-dimethylphenyl, and 2,6-dimethylphenyl; alkoxy groups having 1 to 6 carbon atoms such as methoxy and ethoxy; and hydroxy groups. Examples include a nitro group; a cyano group; alkylsulfanyl groups having 1 to 6 carbon atoms, such as a methylsulfanyl group or an ethylsulfanyl group; alkylsulfinyl groups having 1 to 6 carbon atoms, such as a methylsulfinyl group or an ethylsulfinyl group; a sulfamoyl group; alkylsulfonyl groups having 1 to 6 carbon atoms, such as a methylsulfonyl group or an ethylsulfonyl group; alkylcarbonyl groups having 1 to 6 carbon atoms, such as an acetyl group, a propionyl group or a butyryl group; and alkoxycarbonyl groups having 1 to 6 carbon atoms, such as a methoxycarbonyl group or an ethoxycarbonyl group.

[0022] R 11 The substituent that the phenyl group represented by the formula (I) may have is preferably a halogen atom, an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxy group, or a methylsulfonyl group, more preferably a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 8 carbon atoms, and particularly preferably a halogen atom (preferably a fluorine atom).

[0023] R 14 and R 15 The substituent that the phenyl group represented by the formula (I) may have is preferably a halogen atom, an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxy group, or a methylsulfonyl group, and more preferably a halogen atom (preferably a fluorine atom) or an alkyl group having 1 to 4 carbon atoms.

[0024] R 12 and R 13Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) include aliphatic chain hydrocarbon groups having 1 to 20 carbon atoms, alicyclic hydrocarbon groups having 3 to 20 carbon atoms, aromatic hydrocarbon groups having 6 to 20 carbon atoms, and groups having 4 to 20 carbon atoms that are combinations of these.

[0025] The aliphatic chain hydrocarbon group may be saturated or unsaturated.

[0026] Examples of the saturated aliphatic chain hydrocarbon group include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups; and branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl groups. The saturated aliphatic chain hydrocarbon group has 1 to 20 carbon atoms, preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4 carbon atoms.

[0027] Examples of the unsaturated aliphatic chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (e.g., 1-propenyl, 2-propenyl), and butenyl (e.g., 1-butenyl, 3-butenyl); and alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), and butynyl (e.g., 1-butynyl, 3-butynyl). The unsaturated aliphatic chain hydrocarbon group has 2 to 20 carbon atoms, preferably 2 to 6, and more preferably 2 to 4.

[0028] Examples of the alicyclic hydrocarbon group having 3 to 20 carbon atoms include a cyclopropyl group, a 1-methylcyclopropyl group, a cyclopentyl group, a cyclohexyl group, a 2-methylcyclohexyl group, a cyclodecyl group, etc. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 10, and more preferably 3 to 7.

[0029] Examples of aromatic hydrocarbon groups having 6 to 20 carbon atoms include phenyl, o-tolyl, m-tolyl, p-tolyl, 2,4-dimethylphenyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2,4-diisopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 3,5-di(tert-butyl)phenyl, 1-naphthyl, and 2-naphthyl groups. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 12, and more preferably 6 to 10.

[0030] Examples of the group having 4 to 20 carbon atoms formed by combining the above hydrocarbon groups include aralkyl groups such as a benzyl group, a (4-methylphenyl)methyl group, and a phenethyl group; and alkyl groups having an alicyclic hydrocarbon group bonded thereto, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

[0031] R 12 and R 13 The hydrocarbon groups having 1 to 20 carbon atoms represented by the formula (I) are preferably each independently a saturated aliphatic chain hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably each independently a saturated aliphatic chain hydrocarbon group having 1 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and even more preferably each independently a linear alkyl group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0032] R 12 and R 13 Examples of the substituent that the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have include R 3 ~R 10 These are the same as the groups explained as the substituents that the hydrocarbon group having 1 to 8 carbon atoms represented by the following formula may have.

[0033] In compound (I), -SO3 - replaces any one of the hydrogen atoms in formula (I). -SO3 -The hydrogen atoms to be substituted with are: R 3 ~R 10 Any of the hydrogen atoms represented by R 3 ~R 10 any of the hydrogen atoms of a hydrocarbon group having 1 to 8 carbon atoms represented by the formula: 11 , R 14 and R 15 any of the hydrogen atoms of a phenyl group represented by the formula: 12 and R 13 and the like. Preferably, it is any of the hydrogen atoms contained in a hydrocarbon group having 1 to 20 carbon atoms represented by the following formula: However, the -SO3 - is 1, and compound (I) is electrically neutral.

[0034] R 3 ~R 10 From the viewpoint of ease of synthesis, each of the groups is preferably a hydrogen atom or a saturated aliphatic chain hydrocarbon group having 1 to 4 carbon atoms, and more preferably a hydrogen atom or a methyl group.

[0035] Ring T 1 The aromatic heterocycle is preferably an aromatic heterocycle containing a nitrogen atom, more preferably a 5-membered aromatic heterocycle containing a nitrogen atom, further preferably a thiazole ring or an oxazole ring, and particularly preferably a group represented by formula (t1) or formula (t2). In addition, from the viewpoint of improving light resistance and heat resistance, ring T 1 is preferably a thiazole ring, more preferably a group represented by formula (t1).

[0036] [ka] [In formula (t1), * represents a bond to a carbocation, and ** represents R 11 represents a bond to the nitrogen atom, and *** represents a bond to the nitrogen atom.]

[0037] [ka] [In formula (t2), * represents a bond to a carbocation, and ** represents R 11 represents a bond to the nitrogen atom, and *** represents a bond to the nitrogen atom.]

[0038] R 11 is preferably a phenyl group which may be substituted with a halogen atom, an alkyl group having 1 to 4 carbon atoms, an aromatic hydrocarbon group having 6 to 8 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a hydroxy group, or a methylsulfonyl group, and more preferably a group represented by the following formula: In the following formula, * represents a bond.

[0039] [ka]

[0040] In particular, R 11 is preferably a phenyl group having a halogen atom. From the viewpoint of light resistance, R 11 The number of halogen atoms in the phenyl group represented by the formula (I) is preferably 1 to 5, more preferably 2 to 4, and even more preferably 2 to 3. The halogen atoms are preferably fluorine atoms. Furthermore, the halogen atoms are preferably directly bonded to carbon atoms in the benzene ring.

[0041] R 12 and R 13is preferably each independently a saturated aliphatic chain hydrocarbon group of 1 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group of 6 to 20 carbon atoms which may have a substituent, more preferably each independently an aromatic hydrocarbon group of 6 to 20 carbon atoms which may be substituted with a halogen atom, an alkoxy group of 1 to 4 carbon atoms, a hydroxy group, or a methylsulfonyl group, or a saturated aliphatic chain hydrocarbon group of 1 to 20 carbon atoms, even more preferably each independently a saturated aliphatic chain hydrocarbon group of 1 to 6 carbon atoms or an aromatic hydrocarbon group of 6 to 10 carbon atoms, and particularly preferably each independently a linear alkyl group of 1 to 4 carbon atoms or an aromatic hydrocarbon group of 6 to 10 carbon atoms. Among them, R 12 is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and R 13 is preferably a saturated aliphatic chain hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and R 12 is an aromatic hydrocarbon group having 6 to 10 carbon atoms, and R 13 is more preferably a saturated aliphatic chain hydrocarbon group having 1 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and R 12 is an aromatic hydrocarbon group having 6 to 10 carbon atoms, and R 13 is a linear alkyl group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms is particularly preferred.

[0042] R 14 and R 15 is preferably each independently a group represented by formula (a1).

[0043] [ka] [In formula (a1), R 1a ~R 5a each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxy group, or a methylsulfonyl group.

[0044] R 1a ~R 2a From the viewpoint of heat resistance and light resistance, at least one of the groups is preferably a halogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably at least one of the groups is a halogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably at least one of the groups is a fluorine atom or a linear alkyl group having 1 to 4 carbon atoms.

[0045] R 3a ~R 5a From the viewpoint of ease of synthesis, it is preferable that each of is independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably each of is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and further preferably each of is independently a hydrogen atom or a methyl group.

[0046] Examples of the compound (I) include compounds represented by formula (I-1) and formula (I-2) having groups No. 1 to 400 shown in Tables 1 to 7 below, respectively.

[0047] However, the compounds represented by formula (I-1) and formula (I-2) each independently contain -SO3 - It has one -SO3 - replaces any one of the hydrogen atoms of the compounds represented by formula (I-1) and formula (I-2).

[0048] [ka]

[0049] [ka]

[0050] [Table 1]

[0051] [Table 2]

[0052] [Table 3]

[0053] [Table 4]

[0054] [Table 5]

[0055] [Table 6]

[0056] [Table 7]

[0057] In Tables 1 to 7, Me represents a methyl group, Et represents an ethyl group, iPr represents an isopropyl group, Bu represents an n-butyl group, and Ph1 to Ph5 represent groups represented by the following formulae, respectively: In the following formulae, * represents a bond.

[0058] [ka]

[0059] Among them, as the compound represented by formula (I), the compound represented by formula (I-1) or formula (I-2) having groups No. 161 to No. 400 is preferred, and the compound represented by formula (I-1) or formula (I-2) having groups No. 241 to No. 320 is more preferred.

[0060] Compound (I) can be produced by sulfonating a salt of a cation represented by formula (II) (hereinafter, this salt may be referred to as compound (II)).

[0061] [ka]

[0062] Examples of compound (II) include hydrochlorides, phosphates, sulfates, benzenesulfonates, naphthalenesulfonates, perchlorates, BF4 salts, and PF6 salts of the cation represented by formula (II).

[0063] Compound (II) can be produced, for example, by reacting a compound represented by formula (BI) with a compound represented by formula (CI). This reaction may be carried out in the presence of an organic solvent or in the absence of a solvent.

[0064] [ka]

[0065] [In the formula (BI) and the formula (CI), ring T 1 , R 3 ~R 15 have the same meanings as above.]

[0066] The amount of the compound represented by formula (CI) used is preferably 0.5 to 8 moles, more preferably 0.8 to 3 moles, per mole of the compound represented by formula (BI).

[0067] The reaction temperature is preferably 30° C. to 180° C., more preferably 80° C. to 130° C. The reaction time is preferably 1 hour to 12 hours, more preferably 3 hours to 8 hours.

[0068] From the viewpoint of yield, the reaction is preferably carried out in an organic solvent. Examples of the organic solvent include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and chloroform; alcohol solvents such as methanol, ethanol, isopropanol, and butanol; nitrohydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; and amide solvents such as 1-methyl-2-pyrrolidone. The amount of the organic solvent used is preferably 1 part by mass or more and 20 parts by mass or less, more preferably 1 part by mass or more and 10 parts by mass or less, relative to 1 part by mass of the compound represented by Formula (BI).

[0069] From the viewpoint of yield, the above reaction is preferably carried out in the presence of a condensing agent, such as phosphoric acid, polyphosphoric acid, phosphorus oxychloride, sulfuric acid, or thionyl chloride. The amount of the condensing agent used is preferably 0.1 to 20 parts by mass, more preferably 0.2 to 5 parts by mass, relative to 1 part by mass of the compound represented by formula (BI).

[0070] The method for obtaining Compound (II) from the reaction mixture is not particularly limited, and various known methods can be used, such as a method in which the reaction mixture is filtered to obtain a solid, and the solid is purified by column chromatography or the like.

[0071] The compound of formula (BI) can be produced by various known methods, for example, the method described in West German Patent Application P3928243.0.

[0072] The compound represented by formula (CI) can be produced by reacting a compound represented by formula (CV) with a compound represented by formula (C-VI).

[0073] [ka]

[0074] [In formula (CV) and formula (C-VI), R 3~R 10 have the same meanings as above. R c1 is R 14 and R 15 is the same as R c2 and R c3 is a halogen atom.

[0075] In formula (C-VI), R c2 and R c3 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and from the viewpoint of easy availability of raw materials, a fluorine atom and a chlorine atom are preferred.

[0076] The amount of the compound represented by formula (CV) used is preferably 2 to 5 moles, more preferably 2 to 3 moles, per mole of the compound represented by formula (C-VI). The reaction temperature is preferably 20° C. to 180° C., more preferably 30° C. to 90° C. The reaction time is preferably 10 minutes to 10 hours, more preferably 30 minutes to 2 hours.

[0077] From the viewpoint of yield, the above reaction is preferably carried out in an organic solvent. Examples of the organic solvent include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and chloroform; alcohol solvents such as methanol, ethanol, isopropanol, and butanol; nitrohydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; and amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and 1-methyl-2-pyrrolidone. The amount of the organic solvent used is preferably 1 part by mass or more and 20 parts by mass or less, more preferably 2 parts by mass or more and 10 parts by mass or less, relative to 1 part by mass of the compound represented by Formula (C-VI).

[0078] In terms of yield, the above reaction is preferably carried out in the presence of a palladium compound, a phosphine compound and a basic compound.

[0079] Examples of palladium compounds include palladium(II) acetate, palladium(II) chloride, palladium(II) bromide, bis(2,4-pentanedionato)palladium(II), bis(dibenzylideneacetone)palladium(0), and tris(dibenzylideneacetone)dipalladium(0). The amount of the palladium compound used is preferably 0.0001 mol or more and 0.5 mol or less, more preferably 0.001 mol or more and 0.1 mol or less, relative to 1 mol of the compound represented by Formula (C-VI).

[0080] Examples of the phosphine compound include dppf, Xantphos, BINAP, XPhos, SPhos, and MePhos. The amount of the phosphine compound used is preferably 0.001 mol or more and 0.5 mol or less, more preferably 0.003 mol or more and 0.1 mol or less, per 1 mol of the compound represented by formula (C-VI).

[0081] Examples of basic compounds include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, potassium methoxide, sodium t-butoxide, and potassium t-butoxide. The amount of the basic compound used is preferably 1 mole or more and 5 moles or less, more preferably 1 mole or more and 3 moles or less, relative to 1 mole of the compound represented by formula (C-VI).

[0082] The method for obtaining the compound represented by formula (CI) from the reaction mixture is not particularly limited, and various known methods can be used. For example, after the reaction is completed, the solid compound represented by formula (CI) can be isolated by filtering the reaction mixture. If the compound represented by formula (CI) remains in the filtrate obtained by the filtration, an acidic aqueous solution such as hydrochloric acid and an organic solvent such as toluene can be added to the filtrate, followed by separation to obtain an organic layer. The organic layer can then be separated and washed with an alkaline aqueous solution such as sodium carbonate, followed by distillation to isolate the solid compound represented by formula (CI) from the filtrate. The solid compound represented by formula (CI) obtained from the reaction mixture and the solid compound represented by formula (CI) obtained from the filtrate may be washed with acetonitrile, etc., as necessary.

[0083] The sulfonation of compound (II) can be carried out by various known methods, such as the method described in Journal of Organic Chemistry, (1994), vol. 59, #11, pp. 3232-3236.

[0084] <Colored curable resin composition> The colored curable resin composition of the present invention contains compound (I), which can be used as a colorant (hereinafter, sometimes referred to as colorant (A)). The colored curable resin composition of the present invention preferably further contains a resin (hereinafter, sometimes referred to as resin (B)). The colored curable resin composition of the present invention preferably further contains a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)). The colored curable resin composition of the present invention preferably further contains a solvent (hereinafter, may be referred to as solvent (E)). The colored curable resin composition of the present invention may further contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as each component can be used alone or in combination, unless otherwise specified.

[0085] <Colorant (A)> When the colorant (A) contains the compound (I), the wastewater treatment properties of the developer are improved, and preferably the wastewater treatment properties of the developer and the light resistance and / or heat resistance of the resulting color filter are improved.

[0086] The content of compound (I) is preferably 50% by mass or more, more preferably 70% by mass or more, and even more preferably 85% by mass or more, relative to the total amount of colorant (A), and may be 100% by mass.

[0087] In addition to the compound (I), the colorant (A) may contain a colorant different from the compound (I). The colorant different from the compound (I) may be either a dye (hereinafter sometimes referred to as a dye (A1)) or a pigment (hereinafter sometimes referred to as a pigment (A2)). The colorant different from the compound (I) may contain one or both of the dye (A1) and the pigment (A2).

[0088] The dye (A1) is not particularly limited as long as it does not contain compound (I), and known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as non-pigment dyes with hues in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used based on their chemical structure include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Among these, organic solvent-soluble dyes are preferred.

[0089] Specifically, CI Solvent Yellow 4 (hereinafter, the notation CI Solvent Yellow will be omitted and only the numbers will be listed), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, and 35; 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, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 177, 178, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 23 82, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 388, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 1 23, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324, 335, 340; CI Acid Dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, and 82; CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, and 60, CI Basic Red 1, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic Red 9; CI Basic dyes, such as CI Basic Green 1; CI Reactive Yellow 2,76,116; CI Reactive Orange 16; CI Reactive dyes such as CI Reactive Red 36 CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; 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; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Mordant dyes such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, and 53; Examples include CI Vat dyes such as CI Vat Green 1.

[0090] These dyes may be appropriately selected in accordance with the desired spectral spectrum of the color filter.

[0091] The pigment (A2) is not particularly limited and any known pigment can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments include yellow pigments such as CI Pigment Yellow 1, 3, 10, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 81, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 62, 64, 65, 71, 72, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, 291, 295, 296; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; Brown pigments such as CI Pigment Brown 23 and 25; Examples include black pigments such as CI Pigment Black 1 and 7.

[0092] The pigment may be subjected, as necessary, to a rosin treatment, a surface treatment using a pigment derivative into which an acidic group or a basic group has been introduced, a graft treatment onto the pigment surface using a polymer compound or the like, a microparticle treatment using a sulfuric acid microparticle method or the like, a washing treatment using an organic solvent or water to remove impurities, a treatment to remove ionic impurities using an ion exchange method or the like, or the like. The pigment preferably has a uniform particle size. By adding a pigment dispersant and carrying out a dispersion treatment, it is possible to obtain a pigment dispersion liquid in which the pigment is uniformly dispersed in the solution.

[0093] Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of the pigment dispersant include trade names such as KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Corporation), EFKA (manufactured by CIBA), AJISPER (manufactured by Ajinomoto Fine-Techno Co., Ltd.), and Disperbyk (manufactured by BYK-Chemie). When a pigment dispersant is used, the amount thereof is preferably from 1 to 100% by mass, more preferably from 5 to 50% by mass, based on the total amount of the pigment (A2). When the amount of the pigment dispersant used is within the above range, a pigment dispersion in a uniformly dispersed state tends to be obtained.

[0094] The content of colorant (A) is preferably 5% by mass or more and 60% by mass or less, more preferably 8% by mass or more and 55% by mass or less, and even more preferably 9% by mass or more and 50% by mass or less, based on the total amount of solids. When the content of colorant (A) is within the above range, the color density when made into a color filter is sufficient, and since the necessary amounts of resin (B) and polymerizable compound (C) can be contained in the composition, a pattern with sufficient mechanical strength can be formed.

[0095] Here, the "total amount of solids" in this specification refers to the amount obtained by excluding the content of the solvent from the total amount of the colored curable resin composition. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0096] <Resin (B)> Resin (B) is an alkali-soluble resin. Examples of resin (B) include the following resins [K1] to [K6]. Resin [K1]: a copolymer having structural units derived from at least one member (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]: a copolymer having structural units derived from (a), structural units derived from (b), and structural units derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, sometimes referred to as "(c)"); Resin [K3]: a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]: a copolymer having a structural unit derived from (a) to which (b) has been added, and a structural unit derived from (c); Resin [K5]: a copolymer having a structural unit derived from (b) to which (a) has been added and a structural unit derived from (c); Resin [K6]: A copolymer having a structural unit derived from (c) and a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride.

[0097] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; 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, and 1,4-cyclohexenedicarboxylic acid; bicyclounsaturated compounds containing a carboxy 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; Unsaturated dicarboxylic acid 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, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution.

[0098] In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

[0099] (b) refers to, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0100] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").

[0101] Examples of (b1) include a monomer (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.

[0102] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0103] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (R1), and compounds represented by formula (R2).

[0104] [ka]

[0105] [In formula (R1) and formula (R2), R ra and R rb represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X ra and X rb is a single bond, *-Rrc -, *-R rc -O-, *-R rc -S- or *-R rc represents -NH-. R rc represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0106] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R ra and R rb Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0107] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. X ra and X rb is preferably a single bond, a methylene group, an ethylene group, *-CH2-O - and *-CH2CH2-O-, and more preferably a single bond, *-CH2CH2-O- (* represents a bond to O).

[0108] Examples of compounds represented by formula (R1) include compounds represented by any of formulas (R1-1) to (R1-15). Among these, compounds represented by formula (R1-1), (R1-3), (R1-5), (R1-7), (R1-9), or (R1-11) to (R1-15) are preferred, and compounds represented by formula (R1-1), (R1-7), (R1-9), or (R1-15) are more preferred.

[0109] [ka]

[0110] [ka]

[0111] Compounds represented by formula (R2) include compounds represented by any of formulas (R2-1) to (R2-15). Among these, compounds represented by formula (R2-1), (R2-3), (R2-5), (R2-7), (R2-9), or (R2-11) to (R2-15) are preferred, and compounds represented by formula (R2-1), (R2-7), (R2-9), or (R2-15) are more preferred.

[0112] [ka]

[0113] [ka]

[0114] The compound represented by formula (R1) and the compound represented by formula (R2) may be used alone or in combination of two or more. When the compound represented by formula (R1) and the compound represented by formula (R2) are used in combination, the content ratio thereof [compound represented by formula (R1) : compound represented by formula (R2)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20 on a molar basis.

[0115] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like.

[0116] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0117] As (b), (b1) is preferred in that it can further increase the reliability of the obtained color filter in terms of heat resistance, chemical resistance, etc. Furthermore, (b1-2) is more preferred in that it provides excellent storage stability to the colored curable resin composition.

[0118] Examples of (c) 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] 2,6]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes as "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters such as ]decen-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the technical field), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; 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 Bicyclo[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-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene bicyclounsaturated compounds such as ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide; Examples include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Among these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, 2-hydroxyethyl (meth)acrylate, and the like are preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0119] In the resin [K1], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: When the ratio of the structural units of the resin [K1] is within the above range, the colored composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the resulting color filter.

[0120] Resin [K1] can be produced, for example, by the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and by reference to the references described in said literature.

[0121] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, followed by heating and keeping the temperature while stirring. The polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.). Solvents that dissolve the respective monomers can be used, and examples of the solvents that will be described later as the solvent (E) for the colored curable resin composition of the present invention can be mentioned.

[0122] The resulting copolymer may be used as a solution after the reaction as is, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. In particular, by using the solvent contained in the colored curable resin composition of the present invention as the solvent during the polymerization, the solution after the reaction can be used as is for preparing the colored curable resin composition of the present invention, thereby simplifying the production process for the colored curable resin composition of the present invention.

[0123] In the resin [K2], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 45 mol% Structural units derived from (b): 2 to 95 mol% Structural units derived from (c): 1 to 75 mol% Preferably, Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 80 mol% Structural units derived from (c): 5 to 70 mol% It is more preferable that: When the ratio of the structural units of the resin [K2] is within the above range, the colored curable resin composition tends to have excellent storage stability, developability when forming a colored pattern, and the obtained color filter tends to have excellent solvent resistance, heat resistance, and mechanical strength.

[0124] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0125] In the resin [K3], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that: Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

[0126] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].

[0127] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours to produce the resin [K4]. The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By using this range, the storage stability of the colored curable resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K4], and (b1-1) is more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

[0128] Resin [K5] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0129] Furthermore, under the same conditions as in the production method of resin [K4], resin [K5] can be obtained by reacting the cyclic ether derived from (b) contained in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.

[0130] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of the carboxylic acid anhydride include 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, etc. The amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of the amount of (a) used.

[0131] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid copolymer and other resins [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.02,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, etc. [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, etc. [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, tricyclodecyl Resins such as resins obtained by adding glycidyl (meth)acrylate to a (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer [K4]; resins obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid, resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate copolymer with (meth)acrylic acid [K5]; and resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and further reacting tetrahydrophthalic anhydride with the resin [K6]. Among these, the resin (B) is preferably at least one selected from the group consisting of the resin [K1] and the resin [K2], and the resin [K2] is particularly preferred.

[0132] The polystyrene-equivalent weight average molecular weight of resin (B) is preferably from 3,000 to 100,000, more preferably from 5,000 to 50,000, and even more preferably from 5,000 to 30,000. 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 areas in the developer is good, and the resolution of the colored pattern tends to be improved.

[0133] The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1 or more and 6 or less, and more preferably 1.2 or more and 4 or less.

[0134] The acid value of resin (B) is preferably 50 mg-KOH / g or more and 170 mg-KOH / g or less, more preferably 60 mg-KOH / g or more and 150 mg-KOH / g or less, and even more preferably 70 mg-KOH / g or more and 135 mg-KOH / g or less, calculated on a solids basis. The acid value is measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0135] The content of resin (B) is preferably 7% by mass or more and 65% by mass or less, more preferably 13% by mass or more and 60% by mass or less, and even more preferably 17% by mass or more and 58% by mass or less, based on the total amount of solids. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[0136] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

[0137] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tri(meth)acrylate, tetra ... Examples of the acrylate copolymer include 2-(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate. Among these, at least one selected from the group consisting of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate is preferred.

[0138] The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.

[0139] The content of the polymerizable compound (C) is preferably 7% by mass or more and 65% by mass or less, more preferably 13% by mass or more and 60% by mass or less, and even more preferably 17% by mass or more and 55% by mass or less, based on the total amount of solids. When the content of the polymerizable compound (C) is within the above range, the residual film rate during color pattern formation and the chemical resistance of the color filter tend to be improved.

[0140] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0141] The O-acyloxime compound is a compound having a partial structure represented by formula (d1): Hereinafter, * represents a bond.

[0142] [ka]

[0143] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl)-2-methylbenzoyl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl) ... Examples of suitable hydroxybenzoates include N-acetyl-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine. Commercially available hydroxybenzoates include Irgacure OXE01 and OXE02 (manufactured by BASF), N-1919 (manufactured by ADEKA), and TR-PBG327 (manufactured by Changzhou New Power Electronic Materials Co., Ltd.). Among these, the O-acyloxime compound is preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and more preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine.These O-acyloxime compounds tend to provide color filters with high brightness.

[0144] The alkylphenone compound is a compound having a partial structure represented by formula (d2) or (d3): In these partial structures, the benzene ring may have a substituent.

[0145] [ka]

[0146] Examples of compounds having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used. Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

[0147] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0148] 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) may also be used.

[0149] 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, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, ... 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and imidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).

[0150] Further 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, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) (especially amines) described below.

[0151] Examples of the acid generator 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 tosylates; and benzoin tosylates.

[0152] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0153] 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). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving productivity of the color filter.

[0154] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0155] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 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, among which 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.

[0156] 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.

[0157] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0158] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0159] When these polymerization initiation 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). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with even higher sensitivity, and the productivity of the color filter tends to improve.

[0160] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the art can be used. Examples thereof include ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, or -COO-), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide.

[0161] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0162] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

[0163] Ether ester solvents 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, methyl 2-ethoxy ... Examples of the alkyl ether acetate include ethyl 2-methoxy-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, and diethylene glycol monobutyl ether acetate.

[0164] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0165] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0166] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0167] Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0168] Among the above solvents, from the viewpoints of coatability and drying property, organic solvents having a boiling point at 1 atm of 120° C. or more and 180° C. or less are preferred. As the solvent, a solvent containing at least one selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide is preferred, and a solvent containing at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone is more preferred.

[0169] The content of the solvent (E) is preferably 70% by mass or more and 95% by mass or less, more preferably 75% by mass or more and 92% by mass or less, relative to the total amount of the colored curable resin composition of the present invention. In other words, the total content of the solids in the colored curable resin composition is preferably 5% by mass or more and 30% by mass or less, more preferably 8% by mass or more and 25% by mass or less. When the content of the solvent (E) is within the above range, the flatness during application is good, and when a color filter is formed, the color density is not insufficient, so the display characteristics tend to be good.

[0170] <Leveling Agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms, which may have a polymerizable group in the side chain.

[0171] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule, such as Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade names: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).

[0172] Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule, such as Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by AGC Corporation), and E5844 (manufactured by Daikin Fine Chemical Research Institute, Ltd.).

[0173] Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0174] The content of the leveling agent (F) is preferably 0.001% by mass or more and 0.2% by mass or less, more preferably 0.002% by mass or more and 0.1% by mass or less, and more preferably 0.01% by mass or more and 0.05% by mass or less, relative to the total amount of the colored curable resin composition. Note that this content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0175] <Other ingredients> The colored curable resin composition of the present invention may contain additives known in the technical field, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as necessary.

[0176] <Method for producing colored curable resin composition> The colored curable resin composition of the present invention can be prepared, for example, by mixing the colorant (A), resin (B), polymerizable compound (C), polymerization initiator (D), solvent (E), and optionally the leveling agent (F) and other components. Mixing can be carried out using known or conventional equipment and conditions.

[0177] The colorant (A) may be mixed in advance with part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle size is approximately 0.2 μm or less. At this time, the dispersant and part or all of the resin (B) may be added as needed. The remaining components are preferably mixed with the dispersion thus obtained to a predetermined concentration to prepare the desired colored curable resin composition. When a bead mill is used, the diameter of the beads is preferably 0.05 mm or more and 0.5 mm or less, and the material of the beads may be glass, ceramic, metal, or the like.

[0178] <Color filter manufacturing method> Methods for producing a colored pattern of a color filter from the colored curable resin composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography is a method in which the colored curable resin composition is applied to a substrate, dried to form a composition layer, and then exposed to light through a photomask and developed. In the photolithography, a colored coating film, which is a cured product of the composition layer, can be formed by not using a photomask during exposure and / or not developing.

[0179] The film thickness of the color filter (cured film) is not particularly limited and can be adjusted appropriately depending on the purpose, application, etc., and is, for example, 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and more preferably 0.5 μm or more and 6 μm or less.

[0180] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or silica-coated soda lime glass; a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate; silicon; or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. A separate color filter layer, a resin layer, a transistor, a circuit, or the like may be formed on these substrates. Alternatively, a silicon substrate treated with HMDS may be used.

[0181] Formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be produced as follows. First, a coloring composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying to obtain a smooth composition layer. Examples of application methods include spin coating, slit coating, and slit and spin coating. When heat drying is performed, the temperature is preferably 30°C to 120°C, more preferably 50°C to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When vacuum drying is performed, it is preferably performed under a pressure of 50 to 150 Pa at a temperature of 20 to 25°C. The film thickness of the composition layer is not particularly limited and may be appropriately selected depending on the film thickness of the desired color filter.

[0182] Next, the composition layer is exposed through a photomask to form a desired color pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended application is used. The light source used for exposure is preferably a light source that emits light with a wavelength of 250 to 450 nm. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. It is preferable to use a reduction projection exposure device or proximity exposure device such as a mask aligner or stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light and allows for accurate alignment of the photomask and substrate.

[0183] A colored pattern is formed on the substrate by contacting the exposed composition layer with a developer and developing it. The unexposed portions of the composition layer are dissolved and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. The developer may also contain a surfactant. The development method may be any of a puddle method, a dipping method, a spray method, or the like. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferable to wash with water.

[0184] Furthermore, the obtained colored pattern is preferably post-baked. The post-baking temperature is preferably 80° C. or higher and 250° C. or lower, and more preferably 100° C. or higher and 245° C. or lower. The post-baking time is preferably 1 minute or higher and 120 minutes or lower, and more preferably 2 minutes or higher and 30 minutes or lower.

[0185] The colored patterns and colored coating films thus obtained are useful as color filters, and the color filters are useful as color filters for use in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc. [Example]

[0186] The present invention will now be described in more detail with reference to synthesis examples in which % and parts representing the content or amount used are by mass unless otherwise specified.

[0187] In the following synthesis examples, the structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD model).

[0188] [Colorant Synthesis Example 1] The following reaction was carried out under a nitrogen atmosphere. 26.4 parts of potassium thiocyanate and 156 parts of acetonitrile were placed in a flask equipped with a condenser and a stirrer, and the mixture was stirred at room temperature for 30 minutes. 40.0 parts of 2,6-difluorobenzoic acid chloride (Tokyo Chemical Industry Co., Ltd.) was added dropwise to the flask over 30 minutes, and the mixture was stirred at room temperature for 1 hour. 30.6 parts of N-ethyl-o-toluidine (Tokyo Chemical Industry Co., Ltd.) was added dropwise to the flask over 30 minutes, and the mixture was stirred at room temperature for 1 hour. An aqueous solution of 79.2 parts of sodium monochloroacetate dissolved in 120 parts of ion-exchanged water was added to the flask, and 60.4 parts of a 30% aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature for 18 hours. 600 parts of ion-exchanged water was then added to the flask, and the mixture was stirred for 1 hour. The precipitated yellow-white solid was collected by filtration. The obtained yellow-white solid was washed with 120 parts of acetonitrile and then with 560 parts of ion-exchanged water. The washed yellow-white solid, 156 parts of ion-exchanged water, 35.0 parts of 99% acetic acid (Wako Pure Chemical Industries, Ltd.), and 156 parts of toluene were placed in a flask equipped with a stirrer and stirred at room temperature for 2 hours. 80.8 parts of 30% aqueous sodium hydroxide solution was added dropwise over 10 minutes, followed by stirring for 5 minutes, and the aqueous layer was removed by a separation operation. 156 parts of ion-exchanged water was added to the resulting organic layer for separation and washing, followed by addition of 156 parts of ion-exchanged water and 0.1 parts of 35% hydrochloric acid for separation and washing. The resulting organic layer was concentrated using an evaporator and then dried under reduced pressure at 35°C to obtain the compound represented by formula (BI-1) as a white solid. The yield was 43.4 parts, or 58.0%.

[0189] [ka]

[0190] [Colorant Synthesis Example 2] The following reaction was carried out under a nitrogen atmosphere. 32.2 parts of potassium thiocyanate and 160.0 parts of acetone were placed in a flask equipped with a condenser and a stirrer, and the mixture was stirred at room temperature for 30 minutes. Next, 50.0 parts of 2-fluorobenzoic acid chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over 10 minutes. After the dropwise addition, the mixture was stirred at room temperature for an additional 2 hours. Next, the reaction mixture was ice-cooled, and 40.5 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise. After the dropwise addition, the mixture was stirred at room temperature for an additional 30 minutes. Next, the reaction mixture was ice-cooled, and 34.2 parts of a 30% aqueous sodium hydroxide solution was added dropwise. After the dropwise addition, the mixture was stirred at room temperature for an additional 30 minutes. Next, 31.3 parts of chloroacetic acid was added dropwise at room temperature. After the dropwise addition, the mixture was stirred under reflux with heating for 7 hours. The reaction mixture was then allowed to cool to room temperature, after which the reaction solution was poured into 120.0 parts of water, followed by the addition of 200 parts of toluene and stirring for 30 minutes. Stirring was then stopped, and the mixture was allowed to stand for 30 minutes, resulting in separation into an organic layer and an aqueous layer. The aqueous layer was discarded by separation, and the organic layer was washed with 200 parts of 1N hydrochloric acid, then with 200 parts of water, and finally with 200 parts of saturated saline. An appropriate amount of sodium sulfate was added to the organic layer, and the mixture was stirred for 30 minutes. The mixture was then filtered to obtain a dried organic layer. The solvent in the resulting organic layer was removed using an evaporator to obtain a pale yellow liquid. The resulting pale yellow liquid was purified by column chromatography. The purified pale yellow liquid was dried at 60°C under reduced pressure to obtain 49.9 parts of the compound represented by formula (BI-2). The yield was 51%.

[0191] [ka]

[0192] [Colorant Synthesis Example 3] When a reaction similar to that in Colorant Synthesis Example 1 was carried out using diphenylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.), a compound represented by formula (BI-3) was obtained.

[0193] [ka]

[0194] [Colorant Synthesis Example 4] When a reaction similar to that in Colorant Synthesis Example 1 was carried out using N-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.), a compound represented by formula (BI-4) was obtained.

[0195] [ka]

[0196] [Colorant Synthesis Example 5] When a reaction similar to that in Colorant Synthesis Example 1 was carried out using biphenyl-3-carbonyl chloride (manufactured by Sigma-Aldrich Co.) instead of 2,6-difluorobenzoic acid chloride (manufactured by Tokyo Chemical Industry Co., Ltd.), a compound represented by formula (BI-5) was obtained.

[0197] [ka]

[0198] [Colorant Synthesis Example 6] The following reaction was carried out under a nitrogen atmosphere. 100 parts of 2',6'-difluoroacetophenone, 1127 parts of dichloromethane, and 1.5 parts of aluminum chloride were added to a flask equipped with a condenser and a stirrer. After cooling in an ice-water bath, 113 parts of bromine were added and the mixture was stirred at 25°C for 16 hours. The reaction mixture was then added to 1500 parts of a 10% aqueous sodium thiosulfate solution, and the mixture was mixed and stirred. The organic layer was separated and an appropriate amount of sodium sulfate was added to the resulting organic layer, which was then dried and evaporated to obtain 162 parts of a crude product. This was purified by silica gel column chromatography (solvent: dichloromethane / petroleum ether 5 / 95), and the resulting fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 141 parts of the compound represented by formula (BI-6a).

[0199] [ka]

[0200] Identification of the compound represented by formula (BI-6a) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 235.2 Exact Mass: 234.0

[0201] [Colorant Synthesis Example 7] The following reaction was carried out under a nitrogen atmosphere. 115 parts of the compound represented by formula (BI-6a), 1086 parts of N,N-dimethylformamide, and 294 parts of urea were added to a flask equipped with a condenser and a stirrer, and the mixture was stirred at 80°C for 5 hours. Evaporation yielded 360 parts of a crude product. This was dissolved in 1000 parts of 1.5N hydrochloric acid and washed with 897 parts of ethyl acetate. The aqueous layer was made basic with a 10% aqueous sodium bicarbonate solution and extracted with 897 parts of ethyl acetate. An appropriate amount of sodium sulfate was added to the resulting organic layer, which was then dried and evaporated to yield 54 parts of a crude product. The resulting crude product was suspended in 55 parts of cold ethanol and stirred for 1 hour. The resulting wet solid obtained after filtration was dried under reduced pressure at 60°C to yield 20 parts of the compound represented by formula (BI-6b).

[0202] [ka]

[0203] Identification of the compound represented by formula (BI-6b) (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 197.2 Exact Mass: 196.0

[0204] [Colorant Synthesis Example 8] The following reaction was carried out under a nitrogen atmosphere. A flask equipped with a condenser and a stirrer was charged with 19 parts of the compound represented by formula (BI-6b), 20 parts of 1-bromotoluene, 347 parts of 1,2-dimethoxyethane, 22 parts of potassium tert-butoxide, 1.8 parts of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, and 1.8 parts of tris(dibenzylideneacetone)dipalladium(0), and the mixture was stirred at 100°C for 16 hours. The reaction mixture was then diluted with 449 parts of ethyl acetate, filtered through Celite, and the resulting filtrate was evaporated. 38 parts of the resulting crude product were purified by silica gel column chromatography (solvent: ethyl acetate / petroleum ether 12 / 88), and the resulting fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 12 parts of the compound represented by formula (BI-6c).

[0205] [ka]

[0206] Identification of the compound represented by formula (BI-6c) (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 287.5 Exact Mass: 286.3

[0207] [Colorant Synthesis Example 9] The following reaction was carried out under a nitrogen atmosphere. A flask equipped with a condenser and a stirrer was charged with 10 parts of the compound represented by formula (BI-6c) and 94 parts of N,N-dimethylformamide, and cooled in an ice-water bath. Then, 2.1 parts of sodium hydride (60% oil dispersion) was added and stirred for 1 hour. 10.9 parts of iodoethane was added to the reaction mixture, and the mixture was stirred at 25°C for 2 hours. The reaction mixture was added to 600 parts of ice water, and then acidified with 250 parts of 1.5N hydrochloric acid. Then, 600 parts of ethyl acetate was added and the mixture was separated. An appropriate amount of sodium sulfate was added to the resulting organic layer, and the mixture was dried and evaporated to obtain 12 parts of the compound represented by formula (BI-6).

[0208] [ka]

[0209] Identification of the compound represented by formula (BI-6) (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 315.3 Exact Mass: 314.1

[0210] [Colorant Synthesis Example 10] The following reaction was carried out under a nitrogen atmosphere. A flask equipped with a condenser and a stirrer was charged with 0.27 parts of bis(dibenzylideneacetone)palladium(0) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.57 parts of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (manufactured by Sigma-Aldrich), 42.1 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 50 parts of 4,4'-dichlorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.), and then a mixed solution of 48.3 parts of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 432 parts of toluene was added dropwise to the flask. The reaction solution was stirred for 2 hours while being heated to 80°C in an oil bath. The reaction solution was cooled in an ice bath and then filtered to obtain a solid and a filtrate. This solid was designated Crude Product A1, and the filtrate was designated Filtrate A1. The obtained crude product A1 was washed with 50 parts of toluene, and then washed twice with 250 parts of ion-exchanged water to obtain a solid. This solid was designated as crude product B1. The filtrate A1, 50 parts of toluene, 229 parts of ion-exchanged water, and 20.8 parts of 35% hydrochloric acid were added to a round-bottom flask and stirred for 1 hour, followed by separation to obtain an organic layer. The obtained organic layer was separated and washed with a mixture of 238 parts of ion-exchanged water and 12.5 parts of sodium carbonate, then dried over 150 parts of magnesium sulfate, and the solid was removed by filtration. The obtained organic layer was distilled to obtain a solid. This solid was designated as crude product C1. Crude product B1 and crude product C1 were added to a flask equipped with a stirrer, and acetonitrile was added in an amount four times the total mass of crude product B1 and crude product C1, followed by stirring for 1 hour. The solid obtained by filtering the mixture was washed with acetonitrile in an amount equal to the total mass of crude product B1 and crude product C1. The washed solid was dried at 60°C under reduced pressure to obtain the compound represented by formula (CI-1). The yield was 75.9 parts and the yield was 90.6%.

[0211] [ka]

[0212] [Colorant Synthesis Example 11] When the same reaction as in Colorant Synthesis Example 10 was carried out using 2,4,6-trimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), a compound represented by formula (CI-2) was obtained.

[0213] [ka]

[0214] [Colorant Synthesis Example 12] The following reaction was carried out under a nitrogen atmosphere. 1.4 parts of the compound represented by formula (BI-1), 1.5 parts of the compound represented by formula (CI-1), and 2.3 parts of toluene were placed in a flask equipped with a condenser and a stirrer, followed by the addition of 0.8 parts of phosphorus oxychloride and stirring at 100°C for 7.5 hours. The reaction mixture was then cooled to room temperature, and 10 parts of toluene was added and filtered to obtain a crude product. 37 parts of ethyl acetate was added to the obtained crude product to form a suspension, which was stirred at 25°C for 30 minutes, and the solid was then filtered off. This was purified by silica gel column chromatography (solvent: chloroform / methanol 200 / 1 to 10 / 1), and the obtained fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 2.5 parts of the compound represented by formula (II-1).

[0215] [ka]

[0216] Identification of the compound represented by formula (II-1) (Mass spectrometry) Ionization mode = ESI + : m / z=[M-Cl] + 733.5 Exact Mass: 733.3

[0217] [Colorant Synthesis Example 13] When a reaction similar to that in Colorant Synthesis Example 12 was carried out using a compound represented by formula (BI-2) instead of the compound represented by formula (BI-1), a compound represented by formula (II-2) was obtained.

[0218] [ka]

[0219] Identification of the compound represented by formula (II-2) (Mass spectrometry) Ionization mode = ESI + : m / z=[M-Cl] + 715.5 Exact Mass: 715.3

[0220] [Colorant Synthesis Example 14] When a reaction similar to that in Colorant Synthesis Example 12 was carried out using a compound represented by formula (CI-2) instead of the compound represented by formula (CI-1), a compound represented by formula (II-3) was obtained.

[0221] [ka]

[0222] Identification of the compound represented by formula (II-3) (Mass spectrometry) Ionization mode = ESI + : m / z=[M-Cl] + 761.5 Exact Mass: 761.3

[0223] [Colorant Synthesis Example 15] When the same reaction as in Colorant Synthesis Example 12 was carried out using the compound represented by formula (BI-3) instead of the compound represented by formula (BI-1), a compound represented by formula (II-4) was obtained.

[0224] [ka]

[0225] Identification of the compound represented by formula (II-4) (Mass spectrometry) Ionization mode = ESI + : m / z=[M-Cl]+ 767.5 Exact Mass: 767.3

[0226] [Colorant Synthesis Example 16] When the same reaction as in Colorant Synthesis Example 12 was carried out using the compound represented by formula (BI-4) instead of the compound represented by formula (BI-1), a compound represented by formula (II-5) was obtained.

[0227] [ka]

[0228] Identification of the compound represented by formula (II-5) (Mass spectrometry) Ionization mode = ESI + : m / z=[M-Cl] + 705.5 Exact Mass: 705.3

[0229] [Colorant Synthesis Example 17] When the same reaction as in Colorant Synthesis Example 12 was carried out using the compound represented by formula (BI-5) instead of the compound represented by formula (BI-1), a compound represented by formula (II-6) was obtained.

[0230] [ka]

[0231] Identification of the compound represented by formula (II-6) (Mass spectrometry) Ionization mode = ESI + : m / z=[M-Cl] + 773.7 Exact Mass: 773.4

[0232] [Colorant Synthesis Example 18] The following reaction was carried out under a nitrogen atmosphere. A flask equipped with a condenser and a stirrer was charged with 12 parts of the compound represented by formula (CI-1), 9 parts of the compound represented by formula (BI-6), 13 parts of phosphorus oxychloride, and 121 parts of toluene, and the mixture was stirred at 100°C for 3 hours. The reaction solution was evaporated to obtain 28 parts of a crude product. The resulting crude product was dissolved in 663 parts of dichloromethane, and 500 parts of a 10% aqueous sodium bicarbonate solution was added, followed by liquid separation. An appropriate amount of sodium sulfate was added to the resulting organic layer, which was then dried and evaporated to obtain 26 parts of a crude product. The resulting crude product was purified by silica gel column chromatography (solvent: dichloromethane / acetone 75 / 25, followed by dichloromethane / methanol 92 / 8), and the resulting fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 15 parts of the compound represented by formula (II-7).

[0233] [ka]

[0234] Identification of the compound represented by formula (II-7) (Mass spectrometry) Ionization mode = ESI + : m / z=[M-Cl] + 717.5 Exact Mass: 717.3

[0235] Example 1 The following reaction was carried out under a nitrogen atmosphere. 0.5 parts of the compound represented by formula (II-1) and 9.2 parts of sulfuric acid were placed in a flask equipped with a condenser and a stirrer, and the mixture was stirred at 25°C for 4 hours. The reaction mixture was then slowly added to 30 parts of ice water to form a suspension, which was stirred for 30 minutes and then filtered to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (solvent: chloroform / methanol 10 / 1), and the resulting fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 0.15 parts of the compound represented by formula (I-1-301).

[0236] [ka]

[0237] Identification of the compound represented by formula (I-1-301) (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 813.5 Exact Mass: 812.3

[0238] Example 2 When the same reaction as in Example 1 was carried out using the compound represented by formula (II-2) instead of the compound represented by formula (II-1), the compound represented by formula (I-1-221) was obtained.

[0239] [ka]

[0240] Identification of the compound represented by formula (I-1-221) (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 795.5 Exact Mass: 794.3

[0241] Example 3 The same reaction as in Example 1 was carried out using the compound represented by formula (II-3) instead of the compound represented by formula (II-1), to obtain the compound represented by formula (I-1-302).

[0242] [ka]

[0243] Identification of the compound represented by formula (I-1-302) (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 841.5 Exact Mass: 840.3

[0244] Example 4 The same reaction as in Example 1 was carried out using the compound represented by formula (II-4) instead of the compound represented by formula (II-1), to obtain the compound represented by formula (I-1-245).

[0245] [ka]

[0246] Identification of the compound represented by formula (I-1-245) (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 847.5 Exact Mass: 846.3

[0247] Example 5 The same reaction as in Example 1 was carried out using the compound represented by formula (II-5) instead of the compound represented by formula (II-1), to obtain the compound represented by formula (I-1-269).

[0248] [ka]

[0249] Identification of the compound represented by formula (I-1-269) (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 785.5 Exact Mass: 784.2

[0250] Example 6 The same reaction as in Example 1 was carried out using the compound represented by formula (II-6) instead of the compound represented by formula (II-1), to obtain the compound represented by formula (I-1-381).

[0251] [ka]

[0252] Identification of the compound represented by formula (I-1-381) (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 853.3 Exact Mass: 852.3

[0253] Example 7 The following reaction was carried out under a nitrogen atmosphere. 2.5 parts of the compound represented by formula (II-7) and 46 parts of sulfuric acid were placed in a flask equipped with a condenser and a stirrer, and the mixture was stirred at 25°C for 5 hours. The reaction mixture was then slowly added to 150 parts of ice water to form a suspension, which was stirred for 30 minutes and then filtered to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (solvent: chloroform / methanol 10 / 1), and the resulting fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 0.85 parts of the compound represented by formula (I-2-301).

[0254] [ka]

[0255] Identification of the compound represented by formula (I-2-301) (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 797.0 Exact Mass: 796.3

[0256] [Colorant Synthesis Example 19] The following reaction was carried out under a nitrogen atmosphere. 50 parts of the compound represented by formula (CI-1) and 188 parts of N,N-dimethylformamide were placed in a flask equipped with a condenser and a stirrer, and the mixture was stirred for 30 minutes while cooling in an ice bath. 40 parts of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.) was placed in the flask, and the mixture was stirred for an additional hour while cooling in an ice bath. While the reaction solution was ice-cooled, 55.6 parts of iodoethane (Tokyo Chemical Industry Co., Ltd.) was added dropwise. The reaction solution was heated to 35°C using an oil bath and stirred for 5 hours, and then allowed to cool to room temperature. 1000 parts of a 10% aqueous sodium chloride solution was placed in another flask equipped with a stirrer, and the reaction solution was added dropwise while stirring. After stirring for 30 minutes, the mixture was filtered to obtain a solid. The obtained solid was washed three times with 500 parts of ion-exchanged water and dried at 60°C under reduced pressure to obtain 53.0 parts of the compound represented by formula (x-1). The yield was 93.5%.

[0257] [ka]

[0258] [Colorant Synthesis Example 20] The following reaction was carried out under a nitrogen atmosphere. 13.2 parts of the compound represented by formula (BI-1), 19.0 parts of the compound represented by formula (x-1), and 38 parts of toluene were added to a flask equipped with a condenser and a stirrer, followed by the addition of 9.2 parts of phosphorus oxychloride and stirring at 100°C for 7 hours. The reaction mixture was then cooled to room temperature and diluted with 29 parts of methyl ethyl ketone. A mixture of 114 parts of ion-exchanged water and 10 parts of 35% aqueous hydrochloric acid was then poured into the diluted reaction mixture, and the aqueous layer was removed by separation. The resulting organic layer was evaporated using an evaporator and then dried under reduced pressure at 60°C to obtain the compound represented by formula (x-2) as a blue-purple solid. The yield of the blue-purple solid was 39.4 parts.

[0259] [ka]

[0260] [Colorant Synthesis Example 21] The following reaction was carried out under a nitrogen atmosphere. 38.4 parts of the compound represented by formula (x-2) and 112 parts of methylene chloride were placed in a flask equipped with a condenser and a stirrer and stirred for 30 minutes. The reaction solution was ice-cooled and the internal temperature was maintained at 10°C. 31.6 parts of chlorosulfonic acid (Tokyo Chemical Industry Co., Ltd.) was added, and the reaction solution was then warmed to room temperature and stirred for 9 hours. The reaction solution was then ice-cooled and the internal temperature was maintained at 10°C. The diluted reaction solution was then diluted with a mixed solution of 64 parts of N,N-dimethylformamide and 4.9 parts of ion-exchanged water. The diluted reaction solution was poured into 1120 parts of toluene and stirred for 30 minutes, resulting in the precipitation of a viscous solid. The oil layer was then removed by decantation, and 320 parts of toluene was added to the resulting viscous solid. The mixture was stirred for 30 minutes. The oil layer was then removed by decantation. 832 parts of 20% saline was added to the resulting viscous solid, and the mixture was then stirred for 1 hour. A blue solid was then collected by filtration. The resulting blue solid was washed with 576 parts of 20% brine and dried under reduced pressure at 35°C. The resulting solid and 128 parts of methanol were placed in a flask equipped with a stirrer and stirred for 30 minutes, followed by filtration to separate the solid and filtrate. This filtrate was designated Filtrate A3. The filtered solid was washed with 192 parts of methanol and separated into the solid and filtrate by filtration. This filtrate was designated Filtrate B3. Filtrate A3 and filtrate B3 were mixed, the solvent was removed using an evaporator, and the mixture was dried under reduced pressure at 40°C to obtain the compound represented by formula (x-3) as a blue-purple solid. The yield of the blue-purple solid was 38.3 parts.

[0261] [ka]

[0262] Comparative Example 1 A flask equipped with a condenser and a stirrer was charged with 28.0 parts of the compound represented by formula (x-3), 43.2 parts of barium chloride dihydrate, and 356 parts of ion-exchanged water. The reaction suspension was then stirred at 40°C for 2 hours, and then filtered. The filtered solid and 350 parts of ion-exchanged water were added to a flask equipped with a stirrer, and the mixture was stirred for 30 minutes. The suspension was then filtered. The resulting solid was washed with 280 parts of ion-exchanged water and then dried under reduced pressure at 60°C, yielding the compound represented by formula (x) as a blue-purple solid. The amount obtained was 24.5 parts, and the yield was 81.7%.

[0263] [ka]

[0264] <Wastewater treatment evaluation> A 0.0096 g / L acetonitrile solution of each of the compounds obtained in Examples 1 to 7 and Comparative Example 1 was prepared and used as a measurement sample. Each measurement sample was set in a UV-VIS (JASCO V-650, quartz cell, optical path length: 1 cm) and the absorption spectrum was measured. The wavelength at which the maximum absorbance was obtained was read from the obtained absorption spectrum, and this was designated as the maximum absorption wavelength λ max The results are shown in Table 8.

[0265] 12.5 mg of the compounds obtained in Examples 1 to 7 and Comparative Example 1 were each added to 25 mL of developer (aqueous developer containing 0.12% nonionic surfactant and 0.04% potassium hydroxide) and mixed to prepare model wastewater. 1 g of each model wastewater was diluted with 199 g of distilled water to prepare a sample. Dilute sulfuric acid was added to the sample to adjust the pH to 6 to 8. 4 g of PAC (polyaluminum chloride; manufactured by Asahi Chemical Industry Co., Ltd.) was added and stirred. Next, an aqueous sodium hydroxide solution was added to adjust the pH to 6 to 8, and 0.08 g of an organic polymer flocculant (FK Floc 102D; manufactured by Kubota Chemical Water Co., Ltd.) was added and stirred. 60 minutes after stirring was stopped, the absorption spectrum of the supernatant was measured using a UV-VIS spectrometer (JASCO V-650, quartz cell, optical path length: 1 cm). From the obtained absorption spectrum, the maximum absorption wavelength λ max The absorbance was read at the maximum absorption wavelength λ maxA small absorbance at the maximum absorption wavelength λ indicates that a small amount of colorant remains in the solution after the developer is discharged, that is, the developer has good wastewater treatment properties. max When the absorbance was 0.05 or less, it was marked as ◯, and when it exceeded 0.05, it was marked as ×. The results are shown in Table 8.

[0266] [Table 8]

[0267] [Resin synthesis example 1] A flask equipped with a reflux condenser, a dropping funnel, and a stirrer was filled with nitrogen to replace the atmosphere, and 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added and heated to 85°C with stirring. Next, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0] were added. 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 25 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio), 137 parts of N-cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a 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 completion of the dropwise addition, the mixture was kept at 85°C for 4 hours and then cooled to room temperature to obtain a copolymer (Resin B-1) solution with a viscosity of 23 mPas measured with a Brookfield viscometer (23°C) and a solids content of 25.6%. The weight-average molecular weight Mw of the resulting copolymer was 8.0 x 10 3 The resin B-1 had a polydispersity of 2.1 and an acid value of 109 mg-KOH / g in terms of solid content.

[0268] [ka]

[0269] The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured using a GPC method under the following conditions. Equipment: K2479 (Shimadzu Corporation) Column: SHIMADZU Shim-pack GPC-80M Column temperature: 40°C Solvent: THF (tetrahydrofuran) Test solution concentration: 25mg / mL (solvent: THF) Flow rate; 1.0mL / min Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight calculated in terms of polystyrene obtained above was taken as the dispersity (Mw / Mn).

[0270] Example 8 <Preparation of Colored Curable Resin Composition> Colorant (A-1): Obtained in Example 1 11 parts of the compound represented by formula (I-1-301) Resin (B-1): Resin B-1 (solid content equivalent) 65 parts Polymerizable compound (C-1): Dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 35 parts Polymerization initiator (D-1): a compound represented by the following formula (D-1): (“TR-PBG327” manufactured by Changzhou Strong Electronics New Materials Co., Ltd.) 3 copies Leveling agent (F-1): Polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part Solvent (E-1): 159 parts of propylene glycol monomethyl ether acetate Solvent (E-2): N-methylpyrrolidone 571 parts Solvent (E-3): 37 parts ethyl lactate The above ingredients were mixed to obtain a colored curable resin composition 1.

[0271] [ka]

[0272] [Examples 9 to 13, Comparative Example 2] <Preparation of Colored Curable Resin Composition> Colored curable resin compositions of Examples 9 to 13 and Comparative Example 2 were obtained as shown in Table 9 in the same manner as in Example 8, except that the colorant (A-1) in the colored curable resin composition 1 was changed to colorants (A-2) to (A-7). Colorant (A-2): Compound represented by formula (I-1-221) obtained in Example 2 Colorant (A-3): Compound represented by formula (I-1-302) obtained in Example 3 Colorant (A-4): Compound represented by formula (I-1-245) obtained in Example 4 Colorant (A-5): Compound represented by formula (I-1-269) obtained in Example 5 Colorant (A-6): Compound represented by formula (I-2-301) obtained in Example 7 Colorant (A-7): Compound represented by formula (x) obtained in Comparative Example 1

[0273] [Table 9]

[0274] <Production of color filters (colored patterns)> A colored curable resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated) and then prebaked at 100°C for 3 minutes to obtain a colored composition layer. After cooling, the substrate on which the colored composition layer was formed was placed at a distance of 100 μm from a quartz glass photomask, and the resulting layer was exposed to 60 mJ / cm 2 in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). 2 After that, post-baking was carried out in an oven at 230°C for 20 minutes to obtain a colored coating film.

[0275] <Film thickness measurement> The thickness of the resulting colored coating film was measured using a film thickness measuring device (DEKTAK3, manufactured by Nippon Shinku Gijutsu Co., Ltd.).

[0276] <Lightfastness evaluation> An ultraviolet-cutting filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co., Ltd.; cuts light below 380 nm) was placed on the obtained colored coating film, and the upper surface was irradiated with xenon lamp light using a light resistance tester (Suntest CPS+; manufactured by Toyo Seiki Co., Ltd.) for 48 hours. The chromaticity is measured before and after irradiation, and the color difference △E is calculated from the measured values ​​using the method described in JIS Z 8730:2009 (7. Calculation method of color difference). * The ab was calculated. The results are shown in Table 10. △E * A smaller ab indicates a smaller color change. Furthermore, if the light resistance of a colored coating film is good, it can be said that a colored pattern produced from the same colored curable resin composition also has good light resistance.

[0277] [Table 10]

[0278] <Heat resistance evaluation> 1.△E * ab The resulting colored coating film was heated in an oven at 230°C for 30 minutes. The chromaticity was measured before and after heating, and the color difference ΔE was calculated from the measured values ​​using the method described in JIS Z 8730:2009 (7. Calculation method for color difference). * The ab was calculated. The results are shown in Table 11. △E * A smaller ab indicates a smaller color change. Furthermore, if the heat resistance of a colored coating film is good, it can be said that a colored pattern produced from the same colored curable resin composition also has good heat resistance.

[0279] 2. Absorbance retention rate The resulting colored coating film was heated in an oven at 230°C for 30 minutes. The maximum absorbance was determined from the spectra measured before and after heating, and the maximum absorbance retention was calculated according to the following formula. The results are shown in Table 11. Absorbance retention rate = Maximum absorbance after post-baking / Maximum absorbance after pre-baking The higher the absorbance retention, the better the heat resistance.

[0280] [Table 11] [Industrial Applicability]

[0281] According to the present invention, a compound having excellent wastewater treatment properties for a developer can be provided.

Claims

1. A compound represented by formula (I): 【Chemical 1】 [In formula (I), R 3 ~R 10 each independently represents a hydrogen atom or a carbon atom having 1 to 8 carbon atoms which may have a substituent; represents a hydrogen group or a halogen atom. Ring T 1 represents an aromatic heterocycle. R 11 , R 14 and R 15 each independently represents a phenyl group which may have a substituent. R 12 and R 13 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. However, R 3 ~R 10 a substituent that may be possessed by the hydrocarbon group having 1 to 8 carbon atoms, represented by R 11 , R 14 and R 15 and R 12 and R 13 The substituent that the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have is —SO 3 M (M represents hydrogen ions, metal ions, or ammonium ions). -SO 3 - replaces any one of the hydrogen atoms in formula (I).

2. Ring T 1 The compound according to claim 1, wherein is a five-membered ring containing a nitrogen atom.

3. Ring T 1 The compound according to claim 2, wherein is a thiazole ring or an oxazole ring.

4. A colored curable resin composition comprising a colorant containing the compound according to any one of claims 1 to 3, a resin, a polymerizable compound, a polymerization initiator, and a solvent.

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

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

Images