Compound useful as a colorant, colored curable resin composition containing the compound

Abstract

The present application provides a compound represented by formula (I) to provide a compound having excellent drainage treatment properties for a developer. [In formula (I), R 3 ~R 10 each independently represents a hydrogen atom, a hydrocarbon group having 1 to 8 carbon atoms which can have a substituent, 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 can 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 can have a substituent. The above substituent does not include -SO3M. -SO3 ‑ substitutes any one of the hydrogen atoms possessed by formula (I).]

Description

Technical Field

[0001] The present invention relates to compounds useful as colorants, color-curing resin compositions containing the compounds, color filters formed from the color-curing resin compositions, and display devices containing the color filters. Background Technology

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state imaging elements such as CCDs and CMOS sensors, are manufactured from coloring compositions. As colorants used in such coloring compositions, compounds represented by formula (x) are known (Patent Document 1).

[0003]

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Japanese Patent Application Publication No. 2018-127596 Summary of the Invention

[0007] When manufacturing the colored pattern of a color filter from a colored composition, photolithography is sometimes used. In photolithography, a developer is brought into contact with a layer of colored composition exposed by a photomask, dissolving and removing a portion of the colored composition layer, thereby forming the colored pattern. However, the developer containing the dissolved colored composition usually requires drainage treatment to reduce coloration, which becomes a burden on the process. Therefore, the object of the present invention is to provide a compound useful for reducing developer drainage.

[0008] The main points of this invention are as follows.

[0009] [1] A compound represented by formula (I).

[0010]

[0011] In formula (I),

[0012] R 3 ~R 10 Each can independently represent a hydrogen atom, a hydrocarbon group with 1 to 8 carbon atoms that may have substituents, or a halogen atom.

[0013] Ring T 1 It represents aromatic heterocycles.

[0014] R 11 R 14 and R 15 Each can independently represent a phenyl group that may have substituents.

[0015] R12 and R 13 Each can independently represent a hydrogen atom or a hydrocarbon group with 1 to 20 carbon atoms that may have substituents.

[0016] Among them, R 3 ~R 10 The hydrocarbon groups with 1 to 8 carbon atoms shown can have substituents, R... 11 R 14 and R 15 The phenyl group shown may have substituents and R 12 and R 13 The hydrocarbon groups with 1 to 20 carbon atoms shown may have substituents that do not include -SO3M (M represents hydrogen ion, metal ion or ammonium ion).

[0017] -SO3 - Any one of the hydrogen atoms present in substitution formula (I).

[0018] [2] According to the compound described in [1], wherein the ring T 1 It is a 5-membered ring containing nitrogen atoms.

[0019] [3] According to the compound described in [2], wherein the ring T 1 Thiazole ring or Azole ring.

[0020] [4] A coloring curable resin composition comprising a colorant, a resin, a polymerizable compound, a polymerization initiator and a solvent, wherein the colorant comprises any one of [1] to [3].

[0021] [5] A color filter formed from the color curable resin composition described in [4].

[0022] [6] A display device comprising the color filter described in [5].

[0023] According to the present invention, it is possible to provide compounds that are useful for reducing the drainage of developer, i.e. compounds with excellent drainage properties of developer. Detailed Implementation

[0024] <Compound>

[0025] The compounds of the present invention are those represented by formula (I) (hereinafter, sometimes 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).

[0026]

[0027] In formula (I),

[0028] R 3 ~R 10 Each can independently represent a hydrogen atom, a hydrocarbon group with 1 to 8 carbon atoms that may have substituents, or a halogen atom.

[0029] Ring T 1 It represents aromatic heterocycles.

[0030] R 11 R 14 and R 15 Each can independently represent a phenyl group that may have substituents.

[0031] R 12 and R 13 Each can independently represent a hydrogen atom or a hydrocarbon group with 1 to 20 carbon atoms that may have substituents.

[0032] Among them, R 3 ~R 10 The hydrocarbon groups with 1 to 8 carbon atoms shown can have substituents, R... 11 R 14 and R 15 The phenyl group shown may have substituents and R 12 and R 13 The hydrocarbon groups with 1 to 20 carbon atoms shown may have substituents that do not include -SO3M (M represents hydrogen ion, metal ion or ammonium ion).

[0033] -SO3 - Any one of the hydrogen atoms present in substitution formula (I).

[0034] As R 3 ~R 10 Examples of hydrocarbon groups with 1 to 8 carbon atoms include aliphatic chain hydrocarbon groups with 1 to 8 carbon atoms, alicyclic hydrocarbon groups with 3 to 8 carbon atoms, aromatic hydrocarbon groups with 6 to 8 carbon atoms, and groups with 4 to 8 carbon atoms obtained by combining them.

[0035] The aforementioned aliphatic chain hydrocarbon groups can be saturated or unsaturated.

[0036] Examples of the aforementioned saturated aliphatic chain hydrocarbon groups (hereinafter sometimes referred to as alkyl groups) include straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl; and branched-chain alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl. The number of carbon atoms in the aforementioned saturated aliphatic chain hydrocarbon groups is 1 to 8, preferably 1 to 6, and more preferably 1 to 4.

[0037] Examples of unsaturated aliphatic chain hydrocarbon groups include alkenyl groups such as vinyl, 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 number of carbon atoms in the aforementioned unsaturated aliphatic chain hydrocarbon groups is 2 to 8, preferably 2 to 6, and more preferably 2 to 4.

[0038] Examples of alicyclic hydrocarbon groups with 3 to 8 carbon atoms include cyclopropyl, 1-methylcyclopropyl, cyclopentyl, cyclohexyl, and 2-methylcyclohexyl. The preferred number of carbon atoms for these alicyclic hydrocarbon groups is 3 to 7.

[0039] Examples of aromatic hydrocarbon groups with 6 to 8 carbon atoms include phenyl, o-tolyl, m-tolyl, p-tolyl, 2,4-dimethylphenyl, and 2,6-dimethylphenyl.

[0040] Examples of groups with 4 to 8 carbon atoms obtained by combining the above-mentioned hydrocarbon groups include aryl groups such as benzyl, (4-methylphenyl)methyl, and phenylethyl; and alkyl groups bonded with alicyclic hydrocarbon groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclohexylmethyl, and cyclohexylethyl.

[0041] As R 3 ~R 10 The hydrocarbon group with 1 to 8 carbon atoms shown is preferably a saturated aliphatic chain hydrocarbon group with 1 to 8 carbon atoms, more preferably a saturated aliphatic chain hydrocarbon group with 1 to 4 carbon atoms, and even more preferably a straight-chain alkyl group with 1 to 4 carbon atoms.

[0042] As R 3 ~R 10 The substituents that hydrocarbon groups with 1 to 8 carbon atoms can have include halogen atoms such as fluorine, chlorine, bromine, and iodine; alkoxy groups with 1 to 6 carbon atoms such as methoxy and ethoxy; hydroxyl; nitro; cyano; alkyl thio groups with 1 to 6 carbon atoms such as methylthio and ethylthio; alkyl thiosyl groups with 1 to 6 carbon atoms such as methylthionyl and ethylthionyl; aminosulfonyl; alkyl sulfonyl groups with 1 to 6 carbon atoms such as methylsulfonyl and ethylsulfonyl; alkyl carbonyl groups with 1 to 6 carbon atoms such as acetyl, propionyl, and butyryl; and alkoxy carbonyl groups with 1 to 6 carbon atoms such as methoxycarbonyl and ethoxycarbonyl.

[0043] As R 3 ~R 10 The halogen atoms shown can include fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc., among which fluorine atoms and chlorine atoms are preferred, and fluorine atoms are more preferred.

[0044] As a ring T 1The aromatic heterocycles shown can be either monocyclic or fused rings. (Ring T) 1 The aromatic heterocycle shown preferably has 3 to 10 carbon atoms, more preferably 3 to 8. Furthermore, 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 pyrrole rings, etc. Five-membered rings containing nitrogen atoms, such as azole rings, pyrazole rings, imidazole rings, and thiazole rings; five-membered rings not containing nitrogen atoms, such as furan rings and thiophene rings; six-membered rings containing nitrogen atoms, such as pyridine rings, pyrimidine rings, pyridazine rings, and pyrazine rings; and aromatic heterocycles as fused rings, such as indole rings, benzimidazole rings, benzothiazole rings, and quinoline rings; and rings not containing nitrogen atoms, such as benzofuran rings.

[0045] As R 11 R 14 and R 15 The phenyl group shown can have substituents, including halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups with 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and hexyl; aromatic hydrocarbon groups with 6 to 8 carbon atoms such as phenyl, o-tolyl, m-tolyl, p-tolyl, 2,4-dimethylphenyl, and 2,6-dimethylphenyl; alkoxy groups with 1 to 6 carbon atoms such as methoxy and ethoxy; hydroxyl; nitro; cyano; alkyl thiols with 1 to 6 carbon atoms such as methylthiol and ethylthiol; alkyl thiols with 1 to 6 carbon atoms such as methylthionyl and ethylthionyl; aminosulfonyl; alkyl sulfonyls with 1 to 6 carbon atoms such as methylsulfonyl and ethylsulfonyl; alkyl carbonyls with 1 to 6 carbon atoms such as acetyl, propionyl, and butyryl; and alkoxy carbonyls with 1 to 6 carbon atoms such as methoxycarbonyl and ethoxycarbonyl.

[0046] As R 11 The phenyl group shown may have substituents, preferably halogen atoms, alkyl groups having 1 to 6 carbon atoms, aromatic hydrocarbon groups having 6 to 8 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, hydroxyl groups or methanesulfonyl groups, more preferably halogen atoms, alkyl groups having 1 to 4 carbon atoms or aromatic hydrocarbon groups having 6 to 8 carbon atoms, and particularly preferably halogen atoms (preferably fluorine atoms).

[0047] As R 14 and R 15 The phenyl group shown may have substituents, preferably halogen atoms, alkyl groups having 1 to 6 carbon atoms, aromatic hydrocarbon groups having 6 to 8 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, hydroxyl groups or methanesulfonyl groups, more preferably halogen atoms (preferably fluorine atoms) or alkyl groups having 1 to 4 carbon atoms.

[0048] As R 12 and R 13Examples of hydrocarbon groups with 1 to 20 carbon atoms include aliphatic chain hydrocarbon groups with 1 to 20 carbon atoms, alicyclic hydrocarbon groups with 3 to 20 carbon atoms, aromatic hydrocarbon groups with 6 to 20 carbon atoms, and groups with 4 to 20 carbon atoms obtained by combining them.

[0049] The aforementioned aliphatic chain hydrocarbon groups can be saturated or unsaturated.

[0050] Examples of saturated aliphatic chain hydrocarbon groups include straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; and branched-chain alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl. The number of carbon atoms in the aforementioned saturated aliphatic chain hydrocarbon groups is 1 to 20, preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.

[0051] Examples of unsaturated aliphatic chain hydrocarbon groups include alkenyl groups such as vinyl, 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 number of carbon atoms in the aforementioned unsaturated aliphatic chain hydrocarbon groups is 2 to 20, preferably 2 to 6, and more preferably 2 to 4.

[0052] Examples of alicyclic hydrocarbon groups with 3 to 20 carbon atoms include cyclopropyl, 1-methylcyclopropyl, cyclopentyl, cyclohexyl, 2-methylcyclohexyl, and cyclodecyl. The alicyclic hydrocarbon group preferably has 3 to 10 carbon atoms, more preferably 3 to 7.

[0053] Examples of aromatic hydrocarbon groups with 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. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 12, more preferably 6 to 10.

[0054] Examples of groups with 4 to 20 carbon atoms obtained by combining the above-mentioned hydrocarbon groups include aryl groups such as benzyl, (4-methylphenyl)methyl, and phenylethyl; and alkyl groups bonded with alicyclic hydrocarbon groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclohexylmethyl, and cyclohexylethyl.

[0055] As R 12 and R 13The hydrocarbon groups with 1 to 20 carbon atoms shown are preferably saturated aliphatic chain hydrocarbon groups with 1 to 20 carbon atoms or aromatic hydrocarbon groups with 6 to 20 carbon atoms, more preferably saturated aliphatic chain hydrocarbon groups with 1 to 6 carbon atoms or aromatic hydrocarbon groups with 6 to 10 carbon atoms, and even more preferably straight-chain alkyl groups with 1 to 4 carbon atoms or aromatic hydrocarbon groups with 6 to 10 carbon atoms.

[0056] As R 12 and R 13 The substituents that hydrocarbon groups with 1 to 20 carbon atoms can have, and as R 3 ~R 10 The substituents that hydrocarbon groups with 1 to 8 carbon atoms may have are also described.

[0057] In compound (I), -SO3 - The substitution formula (I) contains any one of the hydrogen atoms.

[0058] As a substance -SO3 - The substituted hydrogen atom is preferably R. 3 ~R 10 Any of the hydrogen atoms shown; R 3 ~R 10 Any of the hydrogen atoms present in the hydrocarbon groups with 1 to 8 carbon atoms shown; R 11 R 14 and R 15 Any of the hydrogen atoms present in the phenyl group shown; or R 12 and R 13 The hydrogen atoms present in the hydrocarbon groups with 1 to 20 carbon atoms shown.

[0059] Among them, compound (I) possesses -SO3 - The quantity is 1, and compound (I) is electrically neutral.

[0060] As R 3 ~R 10 From the viewpoint of ease of synthesis, it is preferable that each of the following is an independent hydrogen atom or a saturated aliphatic chain hydrocarbon group having 1 to 4 carbon atoms, and more preferably that each of the following is an independent hydrogen atom or a methyl group.

[0061] As a 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, and even more preferably a thiazole ring or The azole ring is particularly preferred to be a group represented by formula (t1) or formula (t2).

[0062] Furthermore, from the viewpoint of improving light and heat resistance, ring T1 is preferably a thiazole ring, and more preferably a group represented by formula (t1).

[0063]

[0064] In formula (t1), * represents the bonding site with the carbon cation, and ** represents the bonding site with R. 11 The bonding sites, *** indicates the bonding sites with nitrogen atoms.

[0065]

[0066] In formula (t2), * represents the bonding site with the carbon cation, and ** represents the bonding site with R. 11 The bonding sites, *** indicates the bonding sites with nitrogen atoms.

[0067] As R 11 Preferably, it is a phenyl group that can 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 hydroxyl group, or a methanesulfonyl group, and more preferably, a group represented by the following formula. In the following formula, * indicates a bonding site.

[0068]

[0069] R is the preferred choice 11 It is a phenyl group containing a halogen atom. From the viewpoint of lightfastness, R... 11 The number of halogen atoms in the phenyl group shown is preferably 1 to 5, more preferably 2 to 4, and even more preferably 2 to 3. This halogen atom is preferably a fluorine atom. Furthermore, this halogen atom is preferably directly bonded to a carbon atom of the benzene ring.

[0070] As R 12 and R 13 Preferably, each is an independent saturated aliphatic chain hydrocarbon group with 1 to 20 carbon atoms that may have substituents, or an aromatic hydrocarbon group with 6 to 20 carbon atoms that may have substituents. More preferably, each is an aromatic hydrocarbon group with 6 to 20 carbon atoms that may be substituted by a halogen atom, an alkoxy group with 1 to 4 carbon atoms, a hydroxyl group, or a methanesulfonyl group, or a saturated aliphatic chain hydrocarbon group with 1 to 20 carbon atoms. Further preferably, each is an independent saturated aliphatic chain hydrocarbon group with 1 to 6 carbon atoms or an aromatic hydrocarbon group with 6 to 10 carbon atoms. Particularly preferred are straight-chain alkyl groups with 1 to 4 carbon atoms or aromatic hydrocarbon groups with 6 to 10 carbon atoms.

[0071] The preferred method is as follows: R 12 R is an aromatic hydrocarbon group that can have 6 to 20 carbon atoms and may have substituents. 13The substituent may be 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, R is as follows: 12 It is an aromatic hydrocarbon group with 6 to 10 carbon atoms, R 13 It is a saturated aliphatic chain hydrocarbon group having 1 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms; particularly preferred is the following: R 12 It is an aromatic hydrocarbon group with 6 to 10 carbon atoms, R 13 It is a straight-chain alkyl group with 1 to 4 carbon atoms or an aromatic hydrocarbon group with 6 to 10 carbon atoms.

[0072] As R 14 and R 15 Preferably, each group is an independent group represented by formula (a1).

[0073]

[0074] In formula (a1), R 1a ~R 5a Each of these groups 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 hydroxyl group, or a methanesulfonyl group.

[0075] From the perspectives of heat resistance and light resistance, R 1a ~R 2a Preferably, at least one of them is a halogen atom or an alkyl group having 1 to 6 carbon atoms; more preferably, at least one of them is a halogen atom or an alkyl group having 1 to 4 carbon atoms; and even more preferably, at least one of them is a fluorine atom or a straight-chain alkyl group having 1 to 4 carbon atoms.

[0076] From the perspective of ease of synthesis, R 3a ~R 5a Preferably, each of the alkyl groups is independently composed of hydrogen atoms or 1 to 6 carbon atoms; more preferably, each of the alkyl groups is independently composed of hydrogen atoms or 1 to 4 carbon atoms; and even more preferably, each of the alkyl groups is independently composed of hydrogen atoms or methyl groups.

[0077] Examples of compounds (I) include those having groups No. 1 to 400 as shown in Tables 1 to 7 below, such as those shown in formulas (I-1) and (I-2).

[0078] Among them, the compounds shown in formula (I-1) and formula (I-2) each independently have one - SO3 - SO3 - Substitutes one of the hydrogen atoms in the compounds shown in formulas (I-1) and (I-2).

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] In Tables 1 to 7, Me represents methyl, Et represents ethyl, iPr represents isopropyl, Bu represents n-butyl, and Ph1 to Ph5 represent the groups shown in the following formulas. In the following formulas, * indicates a bonding site.

[0089]

[0090] Among them, the compound represented by formula (I) is preferably the compound represented by formula (I-1) or formula (I-2) having groups No. 161 to No. 400, and more preferably the compound represented by formula (I-1) or formula (I-2) having groups No. 241 to No. 320.

[0091] Compound (I) can be produced by sulfonating a salt of the cation represented by formula (II) (hereinafter, sometimes referred to as compound (II)).

[0092]

[0093] Examples of compounds (II) include hydrochloride, phosphate, sulfate, benzenesulfonate, naphthalenesulfonate, perchlorate, BF4 salt, PF6 salt, etc., of the cation represented by formula (II).

[0094] Compound (II) can be prepared, for example, by reacting the compound shown in formula (B-I) with the compound shown in formula (C-I). This reaction can be carried out in the presence of an organic solvent or in a solvent-free environment.

[0095]

[0096] In equations (B-I) and (C-I), ring T 1 R 3 ~R 15These represent the same meaning as described above.

[0097] The amount of the compound shown in formula (C-I) used relative to 1 mole of the compound shown in formula (B-I) is preferably 0.5 moles or more and 8 moles or less, more preferably 0.8 moles or more and 3 moles or less.

[0098] The reaction temperature is preferably 30℃~180℃, more preferably 80℃~130℃. The reaction time is preferably 1 hour~12 hours, more preferably 3 hours~8 hours.

[0099] From a yield perspective, the above reaction is preferably carried out in an organic solvent. Examples of organic solvents 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; nitro hydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; and amide solvents such as 1-methyl-2-pyrrolidone. The amount of organic solvent used is preferably 1 part by mass and 20 parts by mass or less, more preferably 1 part by mass and 10 parts by mass or less, relative to 1 part by mass of the compound shown in formula (B-I).

[0100] From a yield perspective, the above reaction is preferably carried out in the presence of a condensing agent. Examples of condensing agents include phosphoric acid, polyphosphoric acid, phosphorus oxychloride, sulfuric acid, and thionyl chloride.

[0101] The amount of condensing agent used is preferably 0.1 parts by mass or more and 20 parts by mass or less, more preferably 0.2 parts by mass or more and 5 parts by mass or less, relative to 1 part by mass of the compound shown in formula (B-I).

[0102] There are no particular limitations on the method for obtaining compound (II) from the reaction mixture, and various known methods can be used. For example, methods such as purifying the solid obtained by filtering the reaction mixture by column chromatography can be cited.

[0103] Various known methods can be cited as methods for manufacturing the compound represented by formula (B-I), such as the method described in German patent application P3928243.0.

[0104] The compound shown in formula (C-I) can be produced by reacting the compound shown in formula (C-V) with the compound shown in formula (C-VI).

[0105]

[0106] In equations (C-V) and (C-VI), R 3 ~R 10 Each of these represents the same meaning as described above. R c1 With R 14 and R15 Same, R c2 and R c3 [These are halogen atoms.]

[0107] In equation (C-VI), R is... c2 and R c3 The halogen atoms shown can be fluorine, chlorine, bromine, and iodine. From the viewpoint of ease of obtaining raw materials, fluorine and chlorine atoms are preferred.

[0108] The amount of the compound represented by formula (C-V) used is preferably 2 or more and 5 or less, more preferably 2 or more and 3 or less, relative to 1 mole of the compound represented by formula (C-VI).

[0109] The reaction temperature is preferably 20℃~180℃, more preferably 30℃~90℃. The reaction time is preferably 10 minutes~10 hours, more preferably 30 minutes~2 hours.

[0110] From a yield perspective, the above reaction is preferably carried out in an organic solvent. Examples of organic solvents 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; nitro hydrocarbon 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 organic solvent used is preferably 1 part by mass and 20 parts by mass or less, more preferably 2 parts by mass and 10 parts by mass or less, relative to 1 part by mass of the compound shown in formula (C-VI).

[0111] From a yield perspective, the above reaction is preferably carried out in the presence of palladium compounds, phosphine compounds, and basic compounds.

[0112] Examples of palladium compounds include palladium(II) acetate, palladium(II) chloride, palladium(II) bromide, bis(2,4-pentanedione)palladium(II), bis(dibenzylideneacetone)palladium(O), and tris(dibenzylideneacetone)dipalladium(O).

[0113] The amount of palladium compound used is preferably 0.0001 moles or more and 0.5 moles or less, more preferably 0.001 moles or more and 0.1 moles or less, relative to 1 mole of the compound shown in formula (C-VI).

[0114] Examples of phosphine compounds include dppf, Xantphos, BINAP, XPhos, SPhos, and MePhos.

[0115] The amount of phosphine compound used is preferably 0.001 moles or more and 0.5 moles or less, more preferably 0.003 moles or more and 0.1 moles or less, relative to 1 mole of the compound shown in formula (C-VI).

[0116] Examples of alkaline compounds include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, potassium methoxide, sodium tert-butoxy, and potassium tert-butoxy.

[0117] The amount of the basic compound used is preferably 1 mole or more and 5 moles or less relative to 1 mole of the compound shown in formula (C-VI), and more preferably 1 mole or more and 3 moles or less.

[0118] There are no particular limitations on the method for obtaining the compound represented by formula (C-I) from the reaction mixture, and various known methods can be used. For example, after the reaction is complete, a solid of the compound represented by formula (C-I) can be obtained by filtering the reaction mixture. Alternatively, if the compound represented by formula (C-I) remains in the filtrate obtained by the above filtration, an acidic aqueous solution such as hydrochloric acid and an organic solvent such as toluene can be added to the filtrate, and after separation to obtain an organic layer, the obtained organic layer can be washed with an alkaline aqueous solution such as sodium carbonate solution, followed by distillation, thereby obtaining a solid of the compound represented by formula (C-I) from the filtrate. The solid of the compound represented by formula (C-I) obtained from the reaction mixture and the solid of the compound represented by formula (C-I) obtained from the filtrate can be washed with acetonitrile or the like as needed.

[0119] As a method for sulfonating compound (II), various well-known methods can be cited, such as those described in Journal of Organic Chemistry, (1994), vol.59, #11, pp.3232-3236.

[0120] <Coloring and Curing Resin Composition>

[0121] The coloring and curing resin composition of the present invention comprises compound (I). Compound (I) can be used as a colorant (hereinafter, sometimes referred to as colorant (A)).

[0122] The coloring and curing resin composition of the present invention preferably further comprises a resin (hereinafter, sometimes referred to as resin (B)).

[0123] The coloring and curing resin composition of the present invention preferably further comprises a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D)).

[0124] The coloring and curing resin composition of the present invention preferably further comprises a solvent (hereinafter, sometimes referred to as solvent (E)).

[0125] The coloring and curing resin composition of the present invention may further contain a leveling agent (hereinafter, sometimes referred to as leveling agent (F)).

[0126] It should be noted that, unless otherwise specified, the compounds exemplified as components in this specification may be used alone or in combination.

[0127] <Coloring Agent (A)>

[0128] By including compound (I) in the colorant (A), the developer has good drainage properties, and preferably the developer has good drainage properties as well as the lightfastness and / or heat resistance of the resulting color filter.

[0129] The content of compound (I) relative to the total amount of colorant (A) is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 85% by mass or more, and can also be 100% by mass.

[0130] In addition to compound (I), colorant (A) may also contain colorants different from compound (I). The colorant different from compound (I) may be either a dye (hereinafter, sometimes referred to as dye (A1)) or a pigment (hereinafter, sometimes referred to as pigment (A2)). The colorant different from compound (I) may contain one or both of these dyes (A1) and pigments (A2).

[0131] There are no particular limitations on the dye (A1) as long as it does not contain compound (I). Known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as hue dyes other than pigments in the Dye Index (published by The Society of Dyers and Colourists) and known dyes listed in dyeing guides (for dyeing companies). Furthermore, based on chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthocyanin dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methylene dyes, azomethyl base dyes, and squaric acid. Dyes, acridine dyes, styrene dyes, coumarin dyes, quinoline dyes, and nitro dyes, etc. Among these, organic solvent-soluble dyes are preferred.

[0132] Specifically, examples include CI Solvent Yellow 4 (hereinafter, the description of CI Solvent Yellow is omitted, only the number is recorded), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, and 189;

[0133] 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;

[0134] CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0135] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0136] 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;

[0137] CI solvent green dyes 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc.

[0138] 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;

[0139] 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, 182, 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;

[0140] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0141] CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

[0142] Acid Blue (CI) values ​​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, 123, 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; 1, 335, 340;

[0143] CI Acid Green dyes include 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, etc.

[0144] 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;

[0145] 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;

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

[0147] CI direct purple 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0148] 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;

[0149] CI Direct Green includes CI direct dyes such as 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, and 82.

[0150] CI Disperse Yellow 51, 54, 76;

[0151] CI Disperse Violet 26, 27;

[0152] CI disperse blue 1, 14, 56, 60, and other CI disperse dyes.

[0153] CI Basic Red 1, 10;

[0154] 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;

[0155] CI Basic Violet 2;

[0156] CI Basic Red 9;

[0157] CI Basic Green 1 and other CI basic dyes

[0158] CI Active Yellow 2, 76, 116;

[0159] CI Active Orange 16;

[0160] CI reactive dyes such as CI Reactive Red 36

[0161] CI Media Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0162] CI Media 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;

[0163] CI Media Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0164] CI Media Purple 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;

[0165] CI Media 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;

[0166] CI mordant green dyes include 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, and 53.

[0167] CI vat green 1 and other CI vat dyes, etc.

[0168] These dyes can be selected appropriately based on the spectroscopic spectrum of the desired color filter.

[0169] As for pigment (A2), there are no particular restrictions, and well-known pigments can be used, such as those classified as pigments in the Dye Index (published by The Society of Dyers and Colourists).

[0170] Examples of yellow pigments include CI pigments 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.

[0171] CI pigments include orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 62, 64, 65, 71, 72, 73, and other orange pigments;

[0172] CI pigments include reds 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, and 296, among others.

[0173] CI pigment blue 15, 15:3, 15:4, 15:6, 60 and other blue pigments;

[0174] CI pigments include purple 1, 19, 23, 29, 32, 36, 38, and other purple pigments;

[0175] CI pigments include green 7, 36, 58, 59, 62, and 63, among other green pigments.

[0176] CI pigments, such as brown 23 and 25;

[0177] CI pigments, black 1, 7, and other black pigments, etc.

[0178] Pigments can be treated with rosin as needed, surface treated with pigment derivatives that have introduced acidic or basic groups, grafted onto the pigment surface with polymers, micronized using sulfuric acid micronization, or cleaned with organic solvents or water to remove impurities, or removed by ion exchange to remove ionic impurities.

[0179] The pigment is preferably of uniform particle size. By dispersing it with a pigment dispersant, a pigment dispersion in which the pigment is uniformly dispersed in the solution can be obtained.

[0180] Examples of pigment dispersants include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants can be used alone or in combination of two or more. Trade names for pigment dispersants include KP (Shin-Etsu Chemical Co., Ltd.), FLOWLEN (Kyoeisha Chemical Co., Ltd.), SOLSPERSE (ZENECA Co., Ltd.), EFKA (CIBA Co., Ltd.), AJISPER (Ajinomoto Fine Technology Co., Ltd.), and Disperbyk (BYK-CHEMIE Co., Ltd.).

[0181] When using a pigment dispersant, the amount used relative to the total amount of pigment (A2) is preferably 1% by mass or more and 100% by mass or less, more preferably 5% by mass or more and 50% by mass or less.

[0182] If the amount of pigment dispersant used is within the above range, there is a tendency to obtain a pigment dispersion in a uniformly dispersed state.

[0183] The content of colorant (A) relative to the total amount of solid components 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. If the content of colorant (A) is within the above range, the color concentration when the filter is made is sufficient, and the composition can contain the necessary amount of resin (B) and polymeric compound (C), thus enabling the formation of a pattern with sufficient mechanical strength.

[0184] Here, "total solids content" in this specification refers to the amount obtained by removing the solvent content from the total amount of the coloring and curing resin composition. The total solids content and the content of each component relative to that total solids content can be determined, for example, by known analytical methods such as liquid chromatography or gas chromatography.

[0185] <Resin (B)>

[0186] Resin (B) is an alkali-soluble resin. Examples of resin (B) include resins [K1] to [K6].

[0187] Resin [K1]: A copolymer having structural units derived from at least one (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)") and structural units derived from monomers (b) having a cyclic ether structure having 2 to 4 carbon atoms and an olefinic unsaturated bond (hereinafter sometimes referred to as "(b)");

[0188] Resin [K2]: A copolymer having structural units from (a), structural units from (b), and structural units from monomer (c) (but different from (a) and (b)) that can copolymerize with (a) (hereafter sometimes referred to as "(c)");

[0189] Resin [K3]: A copolymer having structural units from (a) and structural units from (c);

[0190] Resin [K4]: A copolymer having a structural unit formed by adding (b) to a structural unit from (a) and a structural unit from (c);

[0191] Resin [K5]: A copolymer having a structural unit formed by adding (a) to a structural unit from (b) and a structural unit from (c);

[0192] Resin [K6]: A copolymer having a structural unit formed by adding (a) to a structural unit from (b) and further adding it to a carboxylic anhydride, and a structural unit from (c).

[0193] As for (a), specifically, examples include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid;

[0194] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, zeaxanthin, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexene dicarboxylic acid.

[0195] Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxylated bicyclo[2.2.1]hept-2-ene, 5,6-dicarboxylated bicyclo[2.2.1]hept-2-ene, 5-carboxylated 5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxylated 5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxylated 6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxylated 6-ethylbicyclo[2.2.1]hept-2-ene, etc., are bicyclic unsaturated compounds containing carboxyl groups;

[0196] Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxylic acid bicyclic [2.2.1]hept-2-enoic anhydride and other unsaturated dicarboxylic acid anhydrides;

[0197] Unsaturated mono[(meth)acryloyloxyethyl] esters of polycarboxylic acids with two or more members, such as succinic acid mono[2-(meth)acryloyloxyethyl] ester and phthalic acid mono[2-(meth)acryloyloxyethyl] ester.

[0198] Unsaturated acrylates containing hydroxyl and carboxyl groups in the same molecule, such as α-(hydroxymethyl)acrylic acid.

[0199] Among these, acrylic acid, methacrylic acid, and maleic anhydride are preferred, considering both the copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions.

[0200] It should be noted that in this specification, "(meth)acrylic acid" refers to at least one selected from acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0201] (b) refers to a polymeric compound having, for example, a cyclic ether structure having 2 to 4 carbon atoms (e.g., selected from at least one of heterocyclic propane rings, oxocyclic butane rings, and tetrahydrofuran rings) and an olefinic unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0202] Examples of (b) include monomers having an oxocyclopropyl group and an olefinic unsaturated bond (b1) (hereinafter sometimes referred to as "(b1)"), monomers having an oxocyclobutyl group and an olefinic unsaturated bond (b2) (hereinafter sometimes referred to as "(b2)"), monomers having a tetrahydrofuran group and an olefinic unsaturated bond (b3) (hereinafter sometimes referred to as "(b3)"), etc.

[0203] Examples of (b1) include monomers (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure obtained by epoxidation of a straight-chain or branched aliphatic unsaturated hydrocarbons, and monomers (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure obtained by epoxidation of alicyclic unsaturated hydrocarbons.

[0204] 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(glycidoxymethyl)styrene, 2,4-bis(glycidoxymethyl)styrene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tris(glycidoxymethyl)styrene, and 2,3,5-tris(glycidoxymethyl)styrene. Styrene, 2,3,6-tris(glycidoxymethyl)styrene, 3,4,5-tris(glycidoxymethyl)styrene, 2,4,6-tris(glycidoxymethyl)styrene, etc.

[0205] Examples of compounds (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., CELLOXIDE 2000; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl methacrylate (e.g., CYCLOMER A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl methacrylate (e.g., CYCLOMERM100; manufactured by Daicel Co., Ltd.), compounds of formula (R1), and compounds of formula (R2).

[0206]

[0207] In equations (R1) and (R2), R ra and R rb An alkyl group having 1 to 4 hydrogen atoms or carbon atoms, wherein the hydrogen atoms in the alkyl group may be replaced by hydroxyl groups.

[0208] X ra and X rb Indicates a single bond, *-R rc -、*-R rc -O-、*-R rc -S- or *-R rc -NH-.

[0209] R rc Denotes alkyldiyl groups with 1 to 6 carbon atoms.

[0210] * indicates a binding site with O.

[0211] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.

[0212] Examples of alkyl groups in which hydrogen atoms are replaced by hydroxyl groups include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, and 4-hydroxybutyl.

[0213] As R ra and R rb Preferably, hydrogen atoms, methyl groups, hydroxymethyl groups, 1-hydroxyethyl groups, and 2-hydroxyethyl groups are included; more preferably, hydrogen atoms and methyl groups are included.

[0214] Examples of alkyldiyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl.

[0215] As X ra and X rb Preferred examples include single bonds, methylene, ethylene, *-CH2-O- and *-CH2CH2-O-, and more preferably single bonds and *-CH2CH2-O- (* indicates the bonding site with O).

[0216] Examples of compounds represented by formula (R1) include compounds represented by any one of formulas (R1-1) to (R1-15). Among these, compounds represented by formulas (R1-1), (R1-3), (R1-5), (R1-7), (R1-9), or (R1-11) to (R1-15) are preferred, and compounds represented by formulas (R1-1), (R1-7), (R1-9), or (R1-15) are more preferred.

[0217]

[0218] Examples of compounds represented by formula (R2) include compounds represented by any one of formulas (R2-1) to (R2-15). Among these, compounds represented by formulas (R2-1), (R2-3), (R2-5), (R2-7), (R2-9), or (R2-11) to (R2-15) are preferred, and compounds represented by formulas (R2-1), (R2-7), (R2-9), or (R2-15) are more preferred.

[0219]

[0220] The compounds shown in formula (R1) and formula (R2) can be used individually or in combination of two or more. When the compounds shown in formula (R1) and formula (R2) are used in combination, their content ratio [compound shown in formula (R1):compound shown in formula (R2)] is preferably 5:95 to 95:5 on a molar basis, more preferably 20:80 to 80:20.

[0221] As (b2), monomers having oxetyl and (meth)acryloyloxy groups are 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, etc.

[0222] As (b3), monomers having tetrahydrofuranyl and (meth)acryloyloxy groups are more preferred. Specifically, examples of (b3) include tetrahydrofurfuryl acrylate (e.g., VISCOAT V#150, manufactured by Osaka Organic Chemicals Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0223] As for (b), from the perspective of further improving the reliability of the obtained color filter, such as heat resistance and chemical resistance, (b1) is preferred. Furthermore, from the perspective of excellent storage stability of the color-curing resin composition, (b1-2) is more preferred.

[0224] Examples of (c) include methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, dodecyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclopentyl methacrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, and tricyclo[5.2.1.0] 2,6 ] Decane-8-yl ester (in this technical field, it is commonly referred to as "(meth)acrylate dicyclopentyl ester". Additionally, it is sometimes called "(meth)acrylate tricyclodecyl ester"), (meth)acrylate tricyclo[5.2.1.0] 2,6Decen-8-yl ester (commonly referred to as "(meth)acrylate dicyclopentenyl ester"), (meth)acrylate dicyclopentyloxyethyl ester, (meth)acrylate isobornyl ester, (meth)acrylate adamantyl ester, (meth)acrylate allyl ester, (meth)acrylate propargyl ester, (meth)acrylate phenyl ester, (meth)acrylate naphthyl ester, (meth)acrylate benzyl ester, and other (meth)acrylate esters;

[0225] Hydroxyl methacrylates such as 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate;

[0226] Diethyl maleate, diethyl fumarate, diethyl itaconic acid, and other dicarboxylic acid diesters;

[0227] Bicyclic [2.2.1]hept-2-ene, 5-methylbicyclic [2.2.1]hept-2-ene, 5-ethylbicyclic [2.2.1]hept-2-ene, 5-hydroxybicyclic [2.2.1]hept-2-ene, 5-hydroxymethylbicyclic [2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclic [2.2.1]hept-2-ene, 5-methoxybicyclic [2.2.1]hept-2-ene, 5-ethoxybicyclic [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] Bicyclic unsaturated compounds such as heptyl-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]heptyl-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]heptyl-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]heptyl-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]heptyl-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]heptyl-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]heptyl-2-ene;

[0228] N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimide-3-maleimide benzoate, N-succinimide-4-maleimide butyrate, N-succinimide-6-maleimide hexanoate, N-succinimide-3-maleimide propionate, N-(9-acridyl)maleimide and other dicarbonylimide derivatives;

[0229] Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.

[0230] Among these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and 2-hydroxyethyl (meth)acrylate are preferred in terms of copolymerization reactivity and heat resistance.

[0231] In resin [K1], the ratio of structural units from each component is preferably 2 to 60 mol% from (a) and 40 to 98 mol% from (b) among all structural units constituting resin [K1], more preferably 10 to 50 mol% from (a) and 50 to 90 mol% from (b).

[0232] If the ratio of the structural units of the resin [K1] is within the range described above, there is a tendency for the coloring composition to have excellent storage stability, developability when forming coloring patterns, and solvent resistance of the resulting color filter.

[0233] The resin [K1] can be manufactured, for example, by referring to the method described in the literature "Experimental Method for Polymer Synthesis" (Otsu Takayuki Publishing Co., Ltd. Chemical Dojin 1st Edition 1st Printing, March 1, 1972) and the references described in that literature.

[0234] Specifically, the following method can be used: A specified amount of (a) and (b), the polymerization initiator, and the solvent are placed into a reaction vessel, and a deoxygenated atmosphere is formed, for example, by replacing oxygen with nitrogen, while stirring, heating, and maintaining the temperature. It should be noted that the polymerization initiator and solvent used herein are not particularly limited, and polymerization initiators and solvents commonly used in this field can be used. For example, as polymerization initiators, examples include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylpentanonitrile) etc.) and organic peroxides (benzoyl peroxide, etc.). As solvents, any solvent capable of dissolving the monomers is acceptable. As the solvent (E) for the coloring and curing resin composition of the present invention, examples include solvents described later.

[0235] It should be noted that the obtained copolymer can be used directly from the reaction solution, or from a concentrated or diluted solution, or from a substance removed in solid (powder) form by methods such as reprecipitation. In particular, by using the solvent contained in the coloring and curing resin composition of the present invention as a solvent during the polymerization, the reaction solution can be directly used in the preparation of the coloring and curing resin composition of the present invention, thus simplifying the manufacturing process of the coloring and curing resin composition of the present invention.

[0236] In resin [K2], the ratio of structural units from each component is preferably 2-45 mol% from (a), 2-95 mol% from (b), and 1-75 mol% from (c) of all structural units constituting resin [K2]. More preferably, the ratio is 5-40 mol% from (a), 5-80 mol% from (b), and 5-70 mol% from (c).

[0237] If the ratio of the structural units of the resin [K2] is within the range described above, there is a tendency for the color-curing resin composition to exhibit excellent storage stability, developability when forming color patterns, and solvent resistance, heat resistance, and mechanical strength of the resulting color filter.

[0238] Resin [K2] can be manufactured, for example, in the same manner as the method described in the manufacturing method of resin [K1].

[0239] In resin [K3], the ratio of structural units from each component is preferably 2 to 60 mol% from (a) and 40 to 98 mol% from (c) among all structural units constituting resin [K3], more preferably 10 to 50 mol% from (a) and 50 to 90 mol% from (c).

[0240] Resin [K3] can be manufactured, for example, in the same manner as the method described in the manufacturing method of resin [K1].

[0241] The resin [K4] can be manufactured by the following operation: obtaining a copolymer of (a) and (c), and adding a cyclic ether having 2 to 4 carbon atoms in (b) to a carboxylic acid and / or carboxylic anhydride in (a).

[0242] First, the copolymer of (a) and (c) is manufactured in the same manner as described in the manufacturing method of resin [K1]. At this time, the ratio of structural units from each component is preferably the same as the ratio mentioned in resin [K3].

[0243] Next, the cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a portion of the carboxylic acid and / or carboxylic anhydride from (a) in the copolymer described above.

[0244] Next, to produce the copolymer of (a) and (c), the atmosphere inside the flask is replaced with air instead of nitrogen, and (b), the reaction catalyst of carboxylic acid or carboxylic anhydride with cyclic ether (e.g., tris(dimethylaminomethyl)phenol) and the polymerization inhibitor (e.g., hydroquinone) are placed into the flask. For example, the reaction is carried out at 60 to 130°C for 1 to 10 hours, thereby producing resin [K4].

[0245] The amount of (b) used relative to 100 moles of (a) is preferably 5 to 80 moles, more preferably 10 to 75 moles. Within this range, there is a tendency for a good balance to be achieved in terms of the storage stability of the coloring and curing resin composition, the developability when forming a pattern, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern. From the perspective of the high reactivity of cyclic ethers and the fact that unreacted (b) is less likely to remain, (b1) is preferred as (b) used in resin [K4], and (b1-1) is even more preferred.

[0246] The amount of the above-mentioned reaction catalyst used is preferably 0.001 to 5 parts by mass relative to the total mass of (a), (b), and (c) 100 parts by mass. The amount of the above-mentioned polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to the total mass of (a), (b), and (c) 100 parts by mass.

[0247] The reaction conditions, such as the feeding method, reaction temperature, and time, can be appropriately adjusted taking into account the manufacturing equipment and the heat generated during polymerization. It should be noted that, similar to polymerization conditions, the feeding method and reaction temperature can be appropriately adjusted taking into account the manufacturing equipment and the heat generated during polymerization.

[0248] For resin [K5], as a first stage, copolymers of (b) and (c) are obtained in the same manner as those for resin [K1] described above. Similarly, the resulting copolymer can be used directly from the reaction solution, or from a concentrated or diluted solution, or as a substance extracted in solid (powder) form by methods such as reprecipitation.

[0249] The ratio of structural units from (b) and (c) relative to the total molar number of all structural units constituting the copolymer is preferably 5 to 95 mol% from (b) and 5 to 95 mol% from (c), more preferably 10 to 90 mol% from (b) and 10 to 90 mol% from (c).

[0250] Furthermore, under the same conditions as the manufacturing method of resin [K4], resin [K5] can be obtained by reacting the cyclic ether from (b) present in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride present in (a).

[0251] The amount of (a) used in reaction with the copolymer described above is preferably 5 to 80 moles relative to 100 moles of (b). From the perspective of the high reactivity of cyclic ethers and the low likelihood of unreacted (b) residue, (b1) is preferred as (b) used in resin [K5], and (b1-1) is even more preferred.

[0252] Resin [K6] is obtained by further reacting carboxylic anhydride with resin [K5]. The carboxylic anhydride is reacted with a hydroxyl group generated through the reaction of a cyclic ether with a carboxylic acid or carboxylic anhydride.

[0253] Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxylic bicyclo[2.2.1]hept-2-enoic anhydride. The amount of carboxylic anhydride used is preferably 0.5 to 1 mole relative to the amount used in (a).

[0254] As resin (B), examples specifically include 3,4-epoxycyclohexyl methyl methacrylate / (meth)acrylate copolymer and 3,4-epoxy tricyclic acrylate [5.2.1.0]. 2,6 Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; glycidyl acrylate / (meth)acrylic acid benzyl acrylate / (meth)acrylic acid copolymer, glycidyl acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxy tricyclic acrylic acid [5.2.1.0] 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxy tricyclic acrylate [5.2.1.0] 2,6Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid 2-hydroxyethyl ester copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins obtained by adding glycidyl acrylate to benzyl acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl acrylate to tricyclodecyl acrylate / styrene / (meth)acrylic acid copolymer, ... Resins such as those obtained by addition reaction of tricyclodecyl methacrylate / benzyl methacrylate / (meth)acrylic acid copolymer [K4]; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl methacrylate / (meth)acrylic acid glycidyl acrylate; resins such as those obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl methacrylate / styrene / (meth)acrylic acid glycidyl acrylate [K5]; resins such as those obtained by further reacting a resin obtained by reacting a copolymer of tricyclodecyl methacrylate / (meth)acrylic acid glycidyl acrylate with (meth)acrylic acid with tetrahydrophthalic anhydride [K6], etc.

[0255] Among them, the resin (B) is preferably selected from at least one of resin [K1] and resin [K2], and resin [K2] is particularly preferred.

[0256] The polystyrene-based weight-average molecular weight of resin (B) is preferably 3,000 or more and 100,000 or less, more preferably 5,000 or more and 50,000 or less, and even more preferably 5,000 or more and 30,000 or less. If the molecular weight is within the above range, there is a trend towards increased hardness of the color filter, high residual film rate, good solubility of the unexposed portion in the developer, and improved resolution of the colored pattern.

[0257] The dispersion of resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1 or more and 6 or less, more preferably 1.2 or more and 4 or less.

[0258] The acid value of resin (B), converted from solid content, 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. Here, the acid value is a value determined as the amount (mg) of potassium hydroxide required to neutralize 1g of resin (B), and can be obtained, for example, by titration using an aqueous solution of potassium hydroxide.

[0259] The content of resin (B) relative to the total amount of solid components 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. If the content of resin (B) is within the above range, there is a tendency to form a colored pattern, and the resolution and residual film rate of the colored pattern are improved.

[0260] <Polymerizing Compound (C)>

[0261] The polymerizable compound (C) is a compound that can be polymerized by active free radicals and / or acids generated by a polymerization initiator (D), such as compounds with polymerizable olefinic unsaturated bonds, preferably (meth)acrylate compounds.

[0262] The polymeric compound (C) is preferably a polymeric compound having three or more olefinic 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(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.

[0263] Preferably, it is selected from at least one of pentaerythritol penta(meth)acrylate and pentaerythritol hexa(meth)acrylate.

[0264] The weight-average molecular weight of the polymeric compound (C) is preferably 150 or more and 2900 or less, more preferably 250 or more and 1500 or less.

[0265] The content of the polymeric compound (C) relative to the total amount of solid components 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. If the content of the polymeric compound (C) is within the above range, there is a trend towards improved residual film rate during color pattern formation and improved chemical resistance of the color filter.

[0266] <Polymerization Initiator (D)>

[0267] The polymerization initiator (D) is not particularly limited to any compound that generates active free radicals, acids, etc., through the action of light or heat and can initiate polymerization; known polymerization initiators can be used. Examples of polymerization initiators that generate active free radicals include alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds.

[0268] The above-mentioned O-acyl oxime compounds are compounds having a partial structure as shown in formula (d1). Hereinafter, * indicates a bonding site.

[0269]

[0270] Examples of the aforementioned O-acyl oxime compounds include N-benzoyloxy-1-(4-phenylthioalkylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthioalkylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthioalkylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, and N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxane-pentylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine. N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, etc. Commercially available products such as Irgacure OXE01, OXE02 (manufactured by BASF), N-1919 (manufactured by ADEKA), and TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) can also be used. The O-acyl oxime compound is preferably selected from at least one of N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, more preferably from at least one of N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine. With these O-acyl oxime compounds, there is a tendency to obtain color filters with high brightness.

[0271] The alkyl phenyl ketone compounds described above are compounds having a partial structure as shown in formula (d2) or a partial structure as shown in formula (d3). In these partial structures, the benzene ring may have substituents.

[0272]

[0273] Examples of compounds having a partial structure as shown in formula (d2) include 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one. Commercially available products such as Irgacure 369, 907, and 379 (manufactured by BASF) can also be used.

[0274] Examples of compounds having a partial structure as shown in formula (d3) include oligomers of 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzoyladium dimethyl ketal.

[0275] From the perspective of sensitivity, compounds having a partial structure as shown in formula (d2) are preferred as alkyl phenyl ketone compounds.

[0276] Examples of the aforementioned triazine compounds 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-piperyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine. 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0277] Examples of the aforementioned acylphosphine oxide compounds include 2,4,6-trimethylbenzoyl diphenylphosphine oxide. Commercially available products such as Irgacure 819 (manufactured by BASF) can also be used.

[0278] Examples of the aforementioned biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (e.g., see Japanese Patent Application Publication Nos. 6-75372 and 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole. Imidazole compounds with 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 (e.g., see Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and imidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with an alkoxycarbonyl group (e.g., see Japanese Patent Application Publication No. 7-10913, etc.).

[0279] Furthermore, examples of polymerization initiators (D) include benzoin compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as methyl benzoyl peroxide, 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-phenanthroquinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzoyl, methyl phenylglyoxylate, and titanium decene compounds. These are preferably used in combination with polymerization initiators (D1) (especially amines) described later.

[0280] Examples of acid-generating agents include 4-hydroxyphenyl dimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyl dimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyl dimethylsulfonium p-toluenesulfonate, 4-acetoxyphenyl·methyl·benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, and diphenyliodosulfonium. p-Toluenesulfonate, diphenyliodine hexafluoroantimonates, etc. Salts, nitrobenzyl toluenesulfonates, benzoin toluenesulfonates, etc.

[0281] As a polymerization initiator (D), it is preferable to include a polymerization initiator selected from at least one of alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds and bimidazole compounds, and more preferably a polymerization initiator including an O-acyl oxime compound.

[0282] The content of the polymerization initiator (D) relative to the total mass of resin (B) and polymerizable compound (C) of 100 parts by mass is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less. If the content of the polymerization initiator (D) is within the above range, there is a tendency to increase sensitivity and shorten the exposure time, thereby improving the productivity of the color filter.

[0283] <Polymerization Initiator (D1)>

[0284] A polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound initiated by a polymerization initiator. In cases where a polymerization initiator (D1) is included, it is usually used in combination with a polymerization initiator (D).

[0285] Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0286] Examples of the aforementioned amine compounds 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 benzophenone), 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 Industry Co., Ltd.) can also be used.

[0287] Examples of the aforementioned alkoxyanthracene compounds 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.

[0288] Examples of the aforementioned thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0289] Examples of the aforementioned carboxylic acid compounds include phenylthioalkylacetic acid, methylphenylthioalkylacetic acid, ethylphenylthioalkylacetic acid, methylethylphenylthioalkylacetic acid, dimethylphenylthioalkylacetic acid, methoxyphenylthioalkylacetic acid, dimethoxyphenylthioalkylacetic acid, chlorophenylthioalkylacetic acid, dichlorophenylthioalkylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthioalkylacetic acid, N-naphthylglycine, and naphthioacetic acid.

[0290] When using these polymerization initiator aids (D1), their content relative to the total mass of resin (B) and polymerizable compound (C) of 100 parts by mass is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less. If the amount of polymerization initiator aid (D1) is within this range, there is a tendency to be able to form colored patterns with high sensitivity, thereby increasing the productivity of the color filter.

[0291] <Solvent (E)>

[0292] The solvent (E) is not particularly limited and can be any solvent commonly used in this field. Examples 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 both -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-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc.

[0293] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0294] Examples of ether solvents 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, and 1,4-di(ethylene glycol monomethyl ether). Alkane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether, and methyl anisole, etc.

[0295] Examples of 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, ethyl 2-ethoxy-2-methylpropionate, ethyl 2-methoxy-2-methylpropionate, ethyl 2-methoxy-2-methylpropionate, ethyl 3-methoxy-butylacetate, 3-methyl-3-methoxy-butylacetate, 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.

[0296] 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.

[0297] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol.

[0298] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0299] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0300] Of the solvents mentioned above, from the perspective of coatability and drying properties, organic solvents with a boiling point of 120°C or higher and 180°C or lower at 1 atm are preferred. Preferably, the solvent comprises at least one selected from 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; more preferably, the solvent comprises at least one selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone.

[0301] The solvent (E) content relative to the total amount of the color-curing resin composition of the present invention 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. In other words, the total content of the solid components of the color-curing 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. If the solvent (E) content is within the above range, the flatness during coating becomes good, and the color concentration is not insufficient when forming the color filter; therefore, there is a tendency for good display characteristics.

[0302] <Leveling Agent (F)>

[0303] Examples of leveling agents (F) include silicone surfactants, fluorinated surfactants, and silicone surfactants containing fluorine atoms. They may have polymerizable groups on their side chains.

[0304] As organosilicon surfactants, examples include surfactants with intramolecular siloxane bonds. Specifically, examples include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (Momentive Performance Materials Japan Co., Ltd.).

[0305] Examples of fluorinated surfactants include surfactants with intramolecular fluorocarbon chains. Specifically, examples include Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS-718-K (manufactured by DIC Co., Ltd.), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi Materials Electronics & Chemicals Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by AGC Co., Ltd.), and E5844 (manufactured by Daikin Fine Co., Ltd.). (Made by the Chemical Research Institute), etc.

[0306] As examples of organosilicon surfactants containing fluorine atoms, surfactants with siloxane bonds and fluorocarbon chains within the molecule can be cited. Specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, and Megafac F443 (manufactured by DIC Corporation) can be cited.

[0307] The content of leveling agent (F) relative to the total amount of the coloring and curing resin composition is preferably 0.001% by mass or more and 0.2% by mass or less, 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. It should be noted that this content does not include the content of the pigment dispersant described above. If the content of leveling agent (F) is within the above range, the flatness of the color filter can be well achieved.

[0308] <Other Ingredients>

[0309] The coloring and curing resin composition of the present invention may include fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and other additives known in the art as needed.

[0310] <Method for manufacturing coloring and curing resin compositions>

[0311] The coloring and curing resin composition of the present invention can be prepared, for example, by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E), and a leveling agent (F) and other components as needed. Mixing can be carried out using known or conventional apparatus and conditions.

[0312] The colorant (A) can be used in the following state: pre-mixed with part or all of the solvent (E), and dispersed using a bead mill or the like until the average particle size is about 0.2 μm or less. At this time, part or all of the dispersant and resin (B) can be added as needed. Preferably, the target coloring curable resin composition is prepared by mixing the remaining components into the dispersion obtained in this manner at a predetermined concentration. When using a bead mill, the diameter of the beads is preferably 0.05 mm or more and 0.5 mm or less, and the material of the beads can be glass, ceramic, metal, etc.

[0313] <Method for Manufacturing Color Filters>

[0314] Methods for manufacturing color patterns for color filters using the color-curing resin composition of the present invention include photolithography, inkjet printing, and printing. Photolithography is preferred. Photolithography involves coating the aforementioned color-curing resin composition onto a substrate, drying it to form a composition layer, exposing the composition layer to a photomask, and then developing it. In photolithography, by not using a photomask during exposure and / or not performing development, a colored coating film, which is a cured product of the aforementioned composition layer, can be formed.

[0315] The thickness of the color filter (cured film) is not particularly limited and can be appropriately adjusted according to the purpose and application. For example, it is 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.

[0316] As substrates, glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass with a silica coating can be used; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate can be used; and silicon can be used as substrates on which aluminum, silver, or silver / copper / palladium alloy thin films are formed. Other color filter layers, resin layers, transistors, circuits, etc., can also be formed on these substrates. Additionally, substrates with HMDS treatment applied to silicon substrates can also be used.

[0317] The formation of individual color pixels using photolithography can be performed using known or conventional apparatus and conditions. For example, it can be fabricated as follows: First, a coloring composition is coated onto a substrate, and then subjected to heat drying (pre-baking) and / or vacuum drying to remove volatile components such as solvents and dry the substrate, resulting in a smooth composition layer. Examples of coating methods include spin coating, slot coating, and a combination of slot and spin coating. The temperature for heat drying is preferably 30°C or higher and 120°C or lower, more preferably 50°C or higher and 110°C or lower. The heating time is preferably 10 seconds or higher and 60 minutes or lower, more preferably 30 seconds or higher and 30 minutes or lower. In the case of vacuum drying, it is preferably performed at a pressure of 50 to 150 Pa and a temperature range of 20 to 25°C. The film thickness of the composition layer is not particularly limited, and can be appropriately selected according to the film thickness of the target color filter.

[0318] Next, the composition layer is exposed through a photomask used to form the target color pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the intended use can be used. As the light source used for exposure, a light source that generates light with wavelengths of 250–450 nm is preferred. For example, light less than 350 nm can be cut off using a filter that cuts off that wavelength region, or light near 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength regions. Specifically, examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. In order to uniformly illuminate the exposed surface with parallel light, or to accurately align the photomask with the substrate, a reduction projection exposure apparatus or a proximity exposure apparatus, such as a mask aligner and a stepper, is preferred.

[0319] A colored pattern is formed on a substrate by contacting the exposed composition layer with a developing solution. During development, the unexposed portions of the composition layer dissolve in the developing solution and are removed. Preferably, the developing solution is 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. Furthermore, the developing solution may also contain a surfactant. The developing method can be any of the paddle method, immersion method, or spray method. Furthermore, the substrate can be tilted at any angle during development.

[0320] After development, it is preferable to wash with water.

[0321] Furthermore, it is preferable to perform a post-baking process on the obtained colored pattern. The post-baking temperature is preferably 80°C or higher and 250°C or lower, 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, more preferably 2 minutes or higher and 30 minutes or lower.

[0322] The colored patterns and colored coatings obtained in this way are useful as color filters, which are used in display devices (e.g., liquid crystal displays, organic EL devices, etc.), electronic paper, solid-state imaging elements, etc.

[0323] Example

[0324] Next, a synthesis example will be given to further illustrate the invention. In the example, unless otherwise specified, the percentages and parts representing the content or amount used are based on mass.

[0325] In the following synthetic examples, the structures of the compounds were confirmed by mass analysis (LC; Agilent 1200 type, MASS; Agilent LC / MSD type).

[0326] [Example 1 of colorant synthesis]

[0327] The following reaction was carried out under a nitrogen atmosphere. 26.4 parts of potassium thiocyanate and 156 parts of acetonitrile were added to a flask equipped with a cooling tube and a stirrer, and the mixture was stirred at room temperature for 30 minutes. 40.0 parts of 2,6-difluorobenzoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) were 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 (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise to the flask over 30 minutes, and the mixture was stirred at room temperature for 1 hour. An aqueous solution prepared by dissolving 79.2 parts of sodium monochloroacetate in 120 parts of deionized water was added to the flask, followed by 60.4 parts of a 30% sodium hydroxide aqueous solution, and the mixture was stirred at room temperature for 18 hours. 600 parts of deionized water were further added to the flask, and the mixture was stirred for 1 hour. The precipitated yellowish-white solid was then filtered off. The obtained yellowish-white solid was washed with 120 parts of acetonitrile and then with 560 parts of deionized water. A washed, yellowish-white solid, 156 parts of deionized water, 35.0 parts of 99% acetic acid (manufactured by Wako Pure Chemical Industries, Ltd.), and 156 parts of toluene were added to a flask equipped with a stirrer and stirred at room temperature for 2 hours. 80.8 parts of 30% sodium hydroxide aqueous solution were added dropwise over 10 minutes, followed by stirring for 5 minutes. The aqueous layer was removed by separation. 156 parts of deionized water were added to the resulting organic layer for separation and washing, followed by the addition of 156 parts of deionized water and 0.1 parts of 35% hydrochloric acid for further separation and washing. The resulting organic layer was concentrated using an evaporator and dried under reduced pressure at 35°C to obtain the compound of formula (B-I-1) as a white solid. The yield was 43.4 parts, or 58.0%.

[0328]

[0329] [Example 2 of colorant synthesis]

[0330] The following reaction was carried out under a nitrogen atmosphere. 32.2 parts potassium thiocyanate and 160.0 parts acetone were added to a flask equipped with a cooling tube and a stirrer, and the mixture was stirred at room temperature for 30 minutes. Next, 50.0 parts of 2-fluorobenzoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise over 10 minutes. After the addition was complete, the mixture was stirred further at room temperature for 2 hours. Then, after cooling the reaction mixture, 40.5 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise. After the addition was complete, the mixture was stirred further at room temperature for 30 minutes. Next, after cooling the reaction mixture, 34.2 parts of a 30% sodium hydroxide aqueous solution were added dropwise. After the addition was complete, the mixture was stirred further at room temperature for 30 minutes. Next, 31.3 parts of chloroacetic acid were added dropwise at room temperature. After the addition was complete, the mixture was stirred under reflux for 7 hours. Then, after cooling the reaction mixture to room temperature, the reaction solution was added to 120.0 parts water, followed by 200 parts toluene, and the mixture was stirred for 30 minutes. Next, stirring was stopped, and the mixture was allowed to stand for 30 minutes, resulting in the separation of an organic layer and an aqueous layer. The aqueous layer was discarded by separation, and the organic layer was washed with 200 parts of 1 equivalent hydrochloric acid, followed by 200 parts of water, and finally 200 parts of saturated saline solution. 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 was removed from the organic layer using an evaporator, yielding a pale yellow liquid. This pale yellow liquid was purified by column chromatography. The purified pale yellow liquid was dried under reduced pressure at 60°C to give 49.9 parts of the compound represented by formula (B-I-2). The yield was 51%.

[0331]

[0332] [Example 3 of colorant synthesis]

[0333] Using diphenylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same reaction as in Colorant Synthesis Example 1 was carried out, resulting in the compound shown in formula (B-I-3).

[0334]

[0335] [Example 4 of colorant synthesis]

[0336] Using N-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same reaction as in Colorant Synthesis Example 1 was carried out, resulting in the compound shown in formula (B-I-4).

[0337]

[0338] [Example 5 of colorant synthesis]

[0339] Using biphenyl-3-carbonyl chloride (manufactured by Sigma Aldrich) instead of 2,6-difluorobenzoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same reaction as in Colorant Synthesis Example 1 was carried out, resulting in the compound shown in formula (B-I-5).

[0340]

[0341] [Example 6 of colorant synthesis]

[0342] 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 cooling tube 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% sodium thiosulfate aqueous solution and stirred. The mixture was separated to obtain an organic layer. An appropriate amount of sodium sulfate was added to the obtained organic layer, and the mixture was dried and evaporated to obtain 162 parts of a crude fraction. This fraction was purified by silica gel column chromatography (solvent: dichloromethane / petroleum ether 5 / 95). The fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 141 parts of the compound represented by formula (B-I-6a).

[0343]

[0344] Identification of compounds represented by formula (B-I-6a)

[0345] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] + 235.2

[0346] Accurate quality: 234.0

[0347] [Example 7 of colorant synthesis]

[0348] The following reaction was carried out under a nitrogen atmosphere. 115 parts of the compound shown in formula (B-I-6a), 1086 parts of N,N-dimethylformamide, and 294 parts of urea were added to a flask equipped with a cooling tube and a stirrer, and the mixture was stirred at 80°C for 5 hours. Evaporation was performed to obtain 360 parts of a crude compound. This crude compound was dissolved in 1000 parts of 1.5N hydrochloric acid and washed with 897 parts of ethyl acetate. The aqueous layer was prepared alkaline with a 10% sodium bicarbonate aqueous solution and extracted with 897 parts of ethyl acetate. An appropriate amount of sodium sulfate was added to the resulting organic layer, and the mixture was dried and evaporated to obtain 54 parts of a crude compound. The crude compound was suspended in 55 parts of cold ethanol and stirred for 1 hour. The wet solid obtained by filtration was dried under reduced pressure at 60°C to obtain 20 parts of the compound shown in formula (B-I-6b).

[0349]

[0350] Identification of the compound represented by formula (B-I-6b)

[0351] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] + 197.2

[0352] Accurate quality: 196.0

[0353] [Example 8 of colorant synthesis]

[0354] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a cooling tube and a stirrer, 19 parts of the compound shown in formula (B-I-6b), 20 parts of 1-bromotoluene, 347 parts of 1,2-dimethoxyethane, 22 parts of potassium tert-butoxide, 1.8 parts of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl, and 1.8 parts of tris(dibenzylacetone)dipalladium(O) were added, and the mixture was stirred at 100°C for 16 hours. Next, 449 parts of ethyl acetate were added to the reaction solution for dilution, and the mixture was filtered through diatomaceous earth. The resulting filtrate was evaporated. The resulting crude fraction (38 parts) was purified by silica gel column chromatography (solvent: ethyl acetate / petroleum ether 12 / 88). The fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 12 parts of the compound shown in formula (B-I-6c).

[0355]

[0356] Identification of compounds represented by formula (B-I-6c)

[0357] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] + 287.5

[0358] Accurate mass: 286.3

[0359] [Example 9 of colorant synthesis]

[0360] The following reaction was carried out under a nitrogen atmosphere. Ten parts of the compound shown in formula (B-I-6c) and 94 parts of N,N-dimethylformamide were added to a flask equipped with a cooling tube and a stirrer. After cooling in an ice-water bath, 2.1 parts of sodium hydride (60% oil dispersion) were added and stirred for 1 hour. 10.9 parts of iodoethane were added, and the mixture was stirred at 25°C for 2 hours. The reaction solution was added to 600 parts of ice water, followed by 250 parts of 1.5N hydrochloric acid to form an acidic solution. 600 parts of ethyl acetate were then 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 shown in formula (B-I-6).

[0361]

[0362] Identification of compounds represented by formula (B-I-6)

[0363] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] + 315.3

[0364] Accurate quality: 314.1

[0365] [Example 10 of colorant synthesis]

[0366] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a cooling tube and a stirrer, 0.27 parts of bis(dibenzylacetone)palladium(O) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.57 parts of 2-dicyclohexylphosphine-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.) were added dropwise. 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. The reaction solution was heated to 80°C in an oil bath and stirred for 2 hours. After cooling the reaction solution in an ice bath, it was filtered to obtain a solid and a filtrate. The solid is designated as crude A1, and the filtrate as filtrate A1. The obtained crude substance A1 was washed with 50 parts toluene, followed by two washes with 250 parts of deionized water to obtain a solid. This solid was designated as crude substance B1. Filtrate A1, 50 parts toluene, 229 parts of deionized water, and 20.8 parts of 35% hydrochloric acid were added to a round-bottom flask and stirred for 1 hour. The mixture was then separated to obtain an organic layer. The organic layer was washed with a mixture of 238 parts of deionized water and 12.5 parts of sodium carbonate, dried with 150 parts of magnesium sulfate, and the solid was separated and removed by filtration. The obtained organic layer was distilled to obtain a solid. This solid was designated as crude substance C1. Crude substance B1 and crude substance C1 were added to a flask equipped with a stirrer, and acetonitrile was added at a mass equal to 4 times the total mass of crude substance B1 and crude substance C1. The mixture was stirred for 1 hour. The solid obtained by filtering the mixture was washed with acetonitrile at a mass equal to 1 times the total mass of crude substance B1 and crude substance C1. The washed solid was dried at 60°C under reduced pressure to give the compound represented by formula (C-I-1). The yield was 75.9 parts, or 90.6%.

[0367]

[0368] [Example 11 of colorant synthesis]

[0369] Using 2,4,6-trimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), the same reaction as in Colorant Synthesis Example 10 was carried out, resulting in the compound shown in formula (C-I-2).

[0370]

[0371] [Example 12 of colorant synthesis]

[0372] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a cooling tube and a stirrer, 1.4 parts of the compound shown in formula (B-I-1), 1.5 parts of the compound shown in formula (C-I-1), and 2.3 parts of toluene were added, followed by 0.8 parts of phosphorus oxychloride. The mixture was stirred at 100°C for 7.5 hours. The reaction mixture was then cooled to room temperature, 10 parts of toluene were added, and the mixture was filtered to obtain a crude product. 37 parts of ethyl acetate were added to the crude product to form a suspension. The suspension was stirred at 25°C for 30 minutes, and the solid was separated by filtration. The solid was purified by silica gel column chromatography (solvent: chloroform / methanol 200 / 1 to 10 / 1). The fraction obtained was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 2.5 parts of the compound shown in formula (II-1).

[0373]

[0374] Identification of compounds represented by formula (II-1)

[0375] (Mass Analysis) Ionization Mode = ESI + m / z = [M - Cl] + 733.5

[0376] Accurate quality: 733.3

[0377] [Example 13 of colorant synthesis]

[0378] Using the compound shown in formula (B-I-2) instead of the compound shown in formula (B-I-1), the same reaction as in colorant synthesis example 12 was carried out, resulting in the compound shown in formula (II-2).

[0379]

[0380] Identification of compounds represented by formula (II-2)

[0381] (Mass Analysis) Ionization Mode = ESI + m / z = [M - Cl] + 715.5

[0382] Accurate quality: 715.3

[0383] [Example 14 of colorant synthesis]

[0384] Using the compound shown in formula (C-I-2) instead of the compound shown in formula (C-I-1), the same reaction as in colorant synthesis example 12 was carried out, resulting in the compound shown in formula (II-3).

[0385]

[0386] Identification of compounds represented by formula (II-3)

[0387] (Mass Analysis) Ionization Mode = ESI + m / z = [M - Cl] + 761.5

[0388] Accurate quality: 761.3

[0389] [Example 15 of colorant synthesis]

[0390] Using the compound shown in formula (B-I-3) instead of the compound shown in formula (B-I-1), the same reaction as in colorant synthesis example 12 was carried out, resulting in the compound shown in formula (II-4).

[0391]

[0392] Identification of compounds represented by formula (II-4)

[0393] (Mass Analysis) Ionization Mode = ESI + m / z = [M - Cl] + 767.5

[0394] Accurate quality: 767.3

[0395] [Example 16 of colorant synthesis]

[0396] Using the compound shown in formula (B-I-4) instead of the compound shown in formula (B-I-1), the same reaction as in colorant synthesis example 12 was carried out, resulting in the compound shown in formula (II-5).

[0397]

[0398] Identification of compounds represented by formula (II-5)

[0399] (Mass Analysis) Ionization Mode = ESI + m / z = [M - Cl] + 705.5

[0400] Accurate quality: 705.3

[0401] [Example 17 of colorant synthesis]

[0402] Using the compound shown in formula (B-I-5) instead of the compound shown in formula (B-I-1), the same reaction as in colorant synthesis example 12 was carried out, resulting in the compound shown in formula (II-6).

[0403]

[0404] Identification of compounds represented by formula (II-6)

[0405] (Mass Analysis) Ionization Mode = ESI + m / z = [M - Cl] + 773.7

[0406] Accurate quality: 773.4

[0407] [Example 18 of colorant synthesis]

[0408] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a cooling tube and a stirrer, 12 parts of the compound shown in formula (C-I-1), 9 parts of the compound shown in formula (B-I-6), 13 parts of phosphorus oxychloride, and 121 parts of toluene were added, and the mixture was stirred at 100°C for 3 hours. The reaction solution was evaporated to obtain 28 parts of a crude compound. The obtained crude compound was dissolved in 663 parts of dichloromethane, and 500 parts of a 10% sodium bicarbonate aqueous solution were added for separation. An appropriate amount of sodium sulfate was added to the resulting organic layer, and the mixture was dried and evaporated to obtain 26 parts of a crude compound. The obtained crude compound was purified by silica gel column chromatography (solvents: dichloromethane / acetone 75 / 25 followed by dichloromethane / methanol 92 / 8). The fraction obtained was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 15 parts of the compound shown in formula (II-7).

[0409]

[0410] Identification of compounds represented by formula (II-7)

[0411] (Mass Analysis) Ionization Mode = ESI + m / z = [M - Cl] + 717.5

[0412] Accurate quality: 717.3

[0413] [Example 1]

[0414] The following reaction was carried out under a nitrogen atmosphere. 0.5 parts of the compound shown in formula (II-1) and 9.2 parts of sulfuric acid were added to a flask equipped with a cooling tube 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, stirred for 30 minutes, and filtered to obtain a crude product. The 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 shown in formula (I-1-301).

[0415]

[0416] Identification of the compound represented by formula (I-1-301)

[0417] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] + 813.5

[0418] Accurate quality: 812.3

[0419] [Example 2]

[0420] Using the compound shown in formula (II-2) instead of the compound shown in formula (II-1), the same reaction as in Example 1 was carried out, resulting in the compound shown in formula (I-1-221).

[0421]

[0422] Identification of the compound represented by formula (I-1-221)

[0423] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] + 795.5

[0424] Accurate quality: 794.3

[0425] [Example 3]

[0426] Using the compound shown in formula (II-3) instead of the compound shown in formula (II-1), the same reaction as in Example 1 was carried out, resulting in the compound shown in formula (I-1-302).

[0427]

[0428] Identification of the compound represented by formula (I-1-302)

[0429] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] +841.5

[0430] Accurate mass: 840.3

[0431] [Example 4]

[0432] Using the compound shown in formula (II-4) instead of the compound shown in formula (II-1), the same reaction as in Example 1 was carried out, resulting in the compound shown in formula (I-1-245).

[0433]

[0434] Identification of the compound represented by formula (I-1-245)

[0435] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] + 847.5

[0436] Accurate quality: 846.3

[0437] [Example 5]

[0438] Using the compound shown in formula (II-5) instead of the compound shown in formula (II-1), the same reaction as in Example 1 was carried out, resulting in the compound shown in formula (I-1-269).

[0439]

[0440] Identification of the compound represented by formula (I-1-269)

[0441] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] + 785.5

[0442] Accurate quality: 784.2

[0443] [Example 6]

[0444] Using the compound shown in formula (II-6) instead of the compound shown in formula (II-1), the same reaction as in Example 1 was carried out, resulting in the compound shown in formula (I-1-381).

[0445]

[0446] Identification of the compound represented by formula (I-1-381)

[0447] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] + 853.3

[0448] Accurate quality: 852.3

[0449] [Example 7]

[0450] The following reaction was carried out under a nitrogen atmosphere. 2.5 parts of the compound shown in formula (II-7) and 46 parts of sulfuric acid were added to a flask equipped with a cooling tube 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, stirred for 30 minutes, and filtered to obtain a crude product. The 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 shown in formula (I-2-301).

[0451]

[0452] Identification of the compound represented by formula (I-2-301)

[0453] (Mass Analysis) Ionization Mode = ESI + m / z = [M + H] + 797.0

[0454] Accurate quality: 796.3

[0455] [Example 19 of colorant synthesis]

[0456] The following reaction was carried out under a nitrogen atmosphere. 50 parts of the compound shown in formula (C-I-1) and 188 parts of N,N-dimethylformamide were added to a flask equipped with a cooling tube and a stirrer, and the mixture was stirred while cooling in an ice bath for 30 minutes. 40 parts of potassium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the same flask, and the mixture was further stirred while cooling in an ice bath for 1 hour. After the reaction solution was cooled, 55.6 parts of iodoethane (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise. The reaction solution was heated to 35°C in an oil bath and stirred for 5 hours, then cooled to room temperature. 1000 parts of a 10% sodium chloride aqueous solution were added to another flask equipped with a stirrer, and the above 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 deionized water and dried at 60°C under reduced pressure to obtain 53.0 parts of the compound shown in formula (x-1). The yield was 93.5%.

[0457]

[0458] [Example 20 of colorant synthesis]

[0459] The following reaction was carried out under a nitrogen atmosphere. 13.2 parts of the compound shown in formula (B-I-1), 19.0 parts of the compound shown in formula (x-1), and 38 parts of toluene were added to a flask equipped with a cooling tube and a stirrer. Then, 9.2 parts of phosphorus oxychloride were added, and the mixture was stirred at 100°C for 7 hours. The reaction mixture was then cooled to room temperature and diluted with 29 parts of methyl ethyl ketone. Next, a mixture of 114 parts of ion-exchanged water and 10 parts of 35% hydrochloric acid aqueous solution was injected into the diluted reaction mixture, and the aqueous layer was removed by separation. The resulting organic layer was distilled off the solvent using an evaporator and dried under reduced pressure at 60°C, thereby obtaining the compound shown in formula (x-2) as a blue-purple solid. The yield of the blue-purple solid was 39.4 parts.

[0460]

[0461] [Example 21 of colorant synthesis]

[0462] The following reaction was carried out under a nitrogen atmosphere. 38.4 parts of the compound shown in formula (x-2) and 112 parts of dichloromethane were added to a flask equipped with a cooling tube and a stirrer, and the mixture was stirred for 30 minutes. While the reaction solution was chilled and maintained at an internal temperature of 10°C, 31.6 parts of chlorosulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the reaction solution was heated to room temperature and stirred for 9 hours. Next, while the reaction solution was chilled and maintained at an internal temperature of 10°C, it was diluted with a mixed solution of 64 parts of N,N-dimethylformamide and 4.9 parts of deionized water. The diluted reaction solution was injected into 1120 parts of toluene, and after stirring for 30 minutes, a viscous solid precipitated. After removing the oil layer by decantation, 320 parts of toluene were added to the resulting viscous solid, and the mixture was stirred for 30 minutes. After removing the oil layer by decantation, 832 parts of 20% brine were added to the resulting viscous solid, and after stirring for 1 hour, a blue solid was collected by filtration. The obtained blue solid was washed with 576 parts of 20% saline solution and dried under reduced pressure at 35°C. The solid and 128 parts of methanol were added to a flask equipped with a stirrer, stirred for 30 minutes, and then filtered to separate the solid and filtrate. This filtrate was designated as filtrate A3. The filtered solid was washed with 192 parts of methanol and then filtered to separate the solid and filtrate. This filtrate was designated as filtrate B3. Filtrates A3 and 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.

[0463] The yield of the blue-purple solid was 38.3 parts.

[0464]

[0465] [Comparative Example 1]

[0466] 28.0 parts of the compound shown in formula (x-3), 43.2 parts of barium chloride dihydrate, and 356 parts of ion-exchanged water were added to a flask equipped with a cooling tube and a stirrer. After stirring at 40°C for 2 hours, the reaction suspension was filtered. The filtered solid and 350 parts of ion-exchanged water were added to a flask equipped with a stirrer and stirred for 30 minutes, then the suspension was filtered. The obtained solid was washed with 280 parts of ion-exchanged water and dried under reduced pressure at 60°C to obtain the compound shown in formula (x) as a blue-purple solid. The yield was 24.5 parts, and the yield was 81.7%.

[0467]

[0468] <Drainage Treatment Evaluation>

[0469] 0.0096 g / L acetonitrile solutions of the compounds obtained in Examples 1-7 and Comparative Example 1 were prepared as samples for analysis. Each sample was placed in a UV-VIS (Japanese Spectrophotometer V-650, quartz cuvette, optical path length: 1 cm) and the absorption spectra were measured. The wavelength of maximum absorbance was read from the obtained absorption spectra and taken as the maximum absorption wavelength λ. max The results are shown in Table 8.

[0470] 12.5 mg of the compounds obtained in Examples 1-7 and Comparative Example 1 were added to 25 mL of developing solution (an aqueous developing solution 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 samples. Dilute sulfuric acid was added to the samples to adjust the pH to 6-8. 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 6-8, and 0.08 g of an organic polymeric coagulant (FK Floc 102D; manufactured by Kubota Chemical Co., Ltd.) was added and stirred. After stirring was stopped for 60 minutes, the absorption spectrum of the supernatant was measured using a UV-VIS (Japanese Spectrophotometer V-650, quartz cuvette, optical path length: 1 cm). The wavelength of maximum absorption λ was read from the obtained absorption spectrum. max The absorbance at that point. If the wavelength of maximum absorption is λ. max A low absorbance at a certain point indicates that there is less residual colorant in the solution after the developer has been drained, meaning the developer has good drainage properties. It should be noted that the wavelength of maximum absorption λ... max The absorbance at a value below 0.05 is marked as ○, and the absorbance above 0.05 is marked as ×. The results are shown in Table 8.

[0471] [Table 8]

[0472] <![CDATA[λ max (nm)]]> Drainage treatment Example 1 599 ○ Example 2 597 ○ Example 3 602 ○ Example 4 610 ○ Example 5 603 ○ Example 6 598 ○ Example 7 586 ○ Comparative Example 1 587 ×

[0473] (Resin Synthesis Example 1)

[0474] A suitable amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to displace the atmosphere into a nitrogen atmosphere. 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were then added, and the mixture was heated to 85°C while stirring. Next, 38 parts of acrylic acid and 3,4-epoxytricyclic acrylic acid [5.2.1.0] were added dropwise over 5 hours. 2，6 ] Decane-8-yl ester and 3,4-epoxytricyclic acrylate [5.2.1.0] 2，6 A mixture of decane-9-yl esters (containing 25 parts in a molar ratio of 1:1), 137 parts N-cyclohexylmaleimide, 50 parts 2-hydroxyethyl methacrylate, and 338 parts propylene glycol monomethyl ether acetate was prepared. Meanwhile, a solution containing 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was complete, the solution was maintained 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 using a type B viscometer at 23°C) and a solids content of 25.6%. The weight-average molecular weight (Mw) of the resulting copolymer was 8.0 × 10⁻⁶. 3 The dispersion is 2.1, and the acid value converted from solids is 109 mg-KOH / g. Resin B-1 has the following structural units.

[0475]

[0476] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the above resins were determined using the GPC method under the following conditions.

[0477] Device: K2479 (manufactured by Shimadzu Corporation)

[0478] Column: SHIMADZU Shim-pack GPC-80M

[0479] Column temperature: 40℃

[0480] Solvent: THF (tetrahydrofuran)

[0481] Test solution concentration: 25 mg / mL (solvent: THF)

[0482] Flow rate: 1.0 mL / min

[0483] Detector: RI

[0484] Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0485] The ratio of the weight-average molecular weight to the number-average molecular weight of the polystyrene obtained above is used as the dispersity (Mw / Mn).

[0486] [Example 8]

[0487] <Preparation of Coloring Curable Resin Compositions>

[0488] The following substances are mixed to obtain a coloring and curing resin composition 1.

[0489] Colorant (A-1): 11 parts of the compound of formula (I-1-301) obtained in Example 1

[0490] Resin (B-1): Resin B-1 (solid composition conversion) 65 parts

[0491] Polymerizable compound (C-1): Dipentaerythritol hexaacrylate

[0492] (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 35 portions

[0493] Polymerization initiator (D-1): The compound represented by the following formula (D-1)

[0494] (3 portions of "TR-PBG327" manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.)

[0495] Leveling agent (F-1): Polyether modified silicone oil

[0496] (Toray Silicone SH8400: Manufactured by Toray Dow Corning Co., Ltd.) 0.1 part

[0497] Solvent (E-1): 159 parts of propylene glycol monomethyl ether acetate

[0498] Solvent (E-2): 571 parts of N-methylpyrrolidone

[0499] Solvent (E-3): 37 parts ethyl lactate

[0500]

[0501] [Examples 9-13, Comparative Example 2]

[0502] <Preparation of Coloring Curable Resin Compositions>

[0503] By changing the colorant (A-1) in the above-mentioned coloring curable resin composition 1 to colorants (A-2) to (A-7), the coloring curable resin compositions of Examples 9 to 13 and Comparative Example 2 as shown in Table 9 were obtained in the same manner as in Example 8 above.

[0504] Colorant (A-2): The compound of formula (I-1-221) obtained in Example 2

[0505] Colorant (A-3): The compound of formula (I-1-302) obtained in Example 3

[0506] Colorant (A-4): The compound of formula (I-1-245) obtained in Example 4

[0507] Colorant (A-5): The compound of formula (I-1-269) obtained in Example 5

[0508] Colorant (A-6): The compound of formula (I-2-301) obtained in Example 7

[0509] Colorant (A-7): The compound represented by formula (x) obtained in Comparative Example 1

[0510] [Table 9]

[0511]

[0512] <Creating Color Filters (Coloring Patterns)>

[0513] A colored, curable resin composition was spin-coated onto a 5 cm square glass substrate (EAGLE 2000; manufactured by Corning Incorporated) to obtain a colored composition layer, followed by pre-baking at 100°C for 3 minutes. After cooling, the substrate with the colored composition layer was positioned 100 μm apart from a quartz glass photomask, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used at 60 mJ / cm² in an atmospheric atmosphere. 2 The light was irradiated with an exposure level (365nm reference). Then, it was baked in an oven at 230°C for 20 minutes to obtain a colored coating.

[0514] <Film Thickness Measurement>

[0515] The thickness of the obtained colored coating was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.).

[0516] <Lightfastness Evaluation>

[0517] An ultraviolet cutoff filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Corporation; cuts off light below 380nm) was placed on the obtained colored coating film, and the upper surface was irradiated with a xenon lamp for 48 hours using a lightfastness tester (Suntest CPS+; manufactured by Toyo Seiki Corporation).

[0518] Colorimetric measurements were performed before and after irradiation. Based on these measurements, the color difference ΔE was calculated using the method described in JIS Z 8730:2009 (7. Calculation Method of Color Difference). * ab. The results are shown in Table 10. ΔE * The smaller the ab value, the smaller the color change. Furthermore, if the colored coating has good lightfastness, it can be said that the colored pattern made from the same coloring and curing resin composition also has good lightfastness.

[0519] [Table 10]

[0520]

[0521] <Heat Resistance Evaluation>

[0522] 1.ΔE * ab

[0523] The obtained colored coating was heated in an oven at 230°C for 30 minutes. The colorimetry before and after heating was measured, and the color difference ΔE was calculated based on the measured values ​​using the method described in JIS Z 8730:2009 (7. Calculation Method of Color Difference). * ab. The results are shown in Table 11. ΔE * The smaller the ab value, the smaller the color change. Furthermore, if the heat resistance of the colored coating is good, it can be said that the heat resistance of the colored pattern made from the same coloring and curing resin composition is also good.

[0524] 2. Absorbance retention rate

[0525] The obtained colored coating 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 retention rate of the maximum absorbance was calculated according to the following formula. The results are shown in Table 11.

[0526] Absorbance retention rate = Maximum absorbance after post-baking / Maximum absorbance after pre-baking

[0527] The higher the absorbance retention rate, the better the heat resistance.

[0528] [Table 11]

[0529]

[0530] Industrial availability

[0531] According to the present invention, a compound is provided that has excellent drainage properties for the developer.

Claims

1. A compound, represented by formula (I), In formula (I), R 3 ~R 10 Represents a hydrogen atom. Ring T 1 This refers to an aromatic heterocycle containing a nitrogen atom and consisting of a 5-membered ring. R 11 Indicates unsubstituted or substituted phenyl groups. The substituted phenyl group has a substituent that is 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 hydroxyl group, or a methanesulfonyl group. R 14 and R 15 Each group is independently represented by the group shown in formula (a1). R 12 and R 13 Each can independently represent a saturated aliphatic chain hydrocarbon group with 1 to 20 carbon atoms, or an aromatic hydrocarbon group with 6 to 20 carbon atoms. -SO3 - Any one of the hydrogen atoms present in the substitution formula (I); In equation (a1), R 1a ~R 5a Each can be independently represented by a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

2. The compound according to claim 1, wherein, Ring T 1 Thiazole ring or Azole ring.

3. A coloring-curing resin composition comprising a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent, wherein the colorant comprises the compound of claim 1 or 2.

4. A color filter formed from the color-curing resin composition of claim 3.

5. A display device comprising the color filter of claim 4.

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