compound

Abstract

The objective is to provide a compound capable of forming a color filter with excellent brightness. The above objective is solved by a compound represented by formula (I). [In Formula (I), T1 represents a divalent aromatic hydrocarbon group that may have substituents, T2 represents a divalent aromatic hydrocarbon group that may have substituents or a divalent aromatic heterocyclic group that may have substituents, L1 represents an avalent aliphatic hydrocarbon group having 1 to 12 carbon atoms that may have substituents or a group represented by Formula (i), and a represents an integer greater than or equal to 2.] [In formula (i), T3 represents an avalent aromatic hydrocarbon group that may have substituents or an avalent aromatic heterocyclic group that may have substituents, and L2 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that may have substituents.]

Description

Technology Field

[0001] The present invention relates to a compound, a colored resin composition, a color filter, and a display device. Background Technology

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, or in solid-state imaging elements such as CCDs and CMOS sensors, are manufactured from a colored resin composition. Various coloring agents are used as the colored resin composition for forming the color filter, and examples are known in which compounds represented by the following formulas (x1) or (x2) are used as the coloring agents (Patent Document 1).

[0003] [Chemical Formula 1]

[0004] Prior art literature

[0005] Japanese Patent Publication No. 2014-108975 The problem to be solved

[0006] However, color filters formed from a colored resin composition containing the above compound sometimes failed to sufficiently satisfy brightness. Therefore, the present invention aims to provide a compound capable of forming a color filter with excellent brightness. means of solving the problem

[0007] The gist of the present invention is as follows.

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

[0009] [Chemical Formula 2]

[0010]

[0011] [In the (I) formula,

[0012] R 1 ~R 4 and R 13It represents a hydrocarbon group having 1 to 10 carbon atoms that may have hydrogen atoms or substituents independently.

[0013] R 5 ~R 12 It represents a hydrocarbon group having 1 to 5 carbon atoms that may independently have a hydrogen atom, a halogen atom, or a substituent.

[0014] T 1 It represents a divalent aromatic hydrocarbon group that may have substituents.

[0015] T 2 represents a divalent aromatic hydrocarbon group that may have a substituent or a divalent aromatic complex group that may have a substituent.

[0016] L 1 It represents an aliphatic hydrocarbon group having 1 to 12 carbon atoms that may have a substituent, or a group represented by formula (i).

[0017] a represents an integer greater than or equal to 2.

[0018] b and c represent integers greater than or equal to 1, independently of each other.

[0019] d represents an integer greater than or equal to 0.

[0020] X c- represents the anion of c.

[0021] [Chemical Formula 3]

[0022]

[0023] [Equation (i),

[0024] T 3 ... represents an aromatic hydrocarbon group of a that may have a substituent or an aromatic complex group of a that may have a substituent.

[0025] L 2 It represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that may have substituents.

[0026] * is T 2 [Represents the bonding loss with.]

[0027] [2] R 1 and R 3 Representing a phenyl group that may have this substituent, and R 2 and R 4 α represents a hydrocarbon group having 2 to 10 carbon atoms, and

[0028] The above R 1 and R 3 A compound described in [1] in which the phenyl group has an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions that are ortho positions to the N bonded to the phenyl group.

[0029] [3] A colored resin composition containing a coloring agent and a resin, wherein the coloring agent comprises a compound described in [1] or [2].

[0030] [4] A colored resin composition described in [3] containing additional polymerizable compounds and polymerization initiators.

[0031] [5] A color filter formed from the colored resin composition described in [3] or [4].

[0032] [6] A display device including the color filter described in [5]. Effects of the invention

[0033] According to the present invention, a compound capable of forming a color filter with excellent brightness can be provided. Specific details for implementing the invention

[0034] < Compound >

[0035] The compound of the present invention is a compound represented by formula (I) (hereinafter referred to as compound (I). The present invention will be described in detail below using formula (I), but compound (I) also includes tautomeric isomers of formula (I).

[0036] [Chemical Formula 4]

[0037]

[0038] [In the (I) formula,

[0039] R 1 ~R 4 and R 13 It represents a hydrocarbon group having 1 to 10 carbon atoms that may have hydrogen atoms or substituents independently.

[0040] R 5 ~R 12 It represents a hydrocarbon group having 1 to 5 carbon atoms that may independently have a hydrogen atom, a halogen atom, or a substituent.

[0041] T 1 It represents a divalent aromatic hydrocarbon group that may have substituents.

[0042] T 2 represents a divalent aromatic hydrocarbon group that may have a substituent or a divalent aromatic complex group that may have a substituent.

[0043] L 1 It represents an aliphatic hydrocarbon group having 1 to 12 carbon atoms that may have a substituent, or a group represented by formula (i).

[0044] a represents an integer greater than or equal to 2.

[0045] b and c represent integers greater than or equal to 1, independently of each other.

[0046] d represents an integer greater than or equal to 0.

[0047] X c- represents the anion of c.

[0048] [Chemical Formula 5]

[0049]

[0050] [Equation (i),

[0051] T 3... represents an aromatic hydrocarbon group of a that may have a substituent or an aromatic complex group of a that may have a substituent.

[0052] L 2 It represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that may have substituents.

[0053] a represents the same meaning as above.

[0054] * is T 2 [Represents the bonding loss with.]

[0055] R 1 ~R 4 and R 13 Examples of hydrocarbon groups having 1 to 10 carbon atoms represented by this include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. Aliphatic hydrocarbon groups may be saturated or unsaturated, and may be chain-like or alicyclic.

[0056] As the above-mentioned saturated or unsaturated chain hydrocarbon group, a straight-chain alkyl group such as a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group; Branched-chain alkyl groups such as isopropyl group, (1-ethyl)propyl group, isobutyl group, sec-butyl group, tert-butyl group, (1-ethyl)butyl group, (2-ethyl)butyl group, (1-propyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl)pentyl group, (1-ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (2-methyl)octyl group, (2-ethyl)octyl group, etc. Examples include alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, 2-pentenyl group, etc.

[0057] Examples of the above saturated or unsaturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohexa-2-ene, cyclohexa-3-ene), cycloheptenyl, and cyclooctyl groups; norbornyl, adamantyl, and bicyclo[2.2.2]octyl groups.

[0058] As aromatic hydrocarbon groups, aryl groups such as phenyl groups, 1-naphthyl groups, and 2-naphthyl groups; alkylaryl groups such as o-tolyl groups, m-tolyl groups, p-tolyl groups, 2-ethylphenyl groups, 3-ethylphenyl groups, 4-ethylphenyl groups, 2,3-dimethylphenyl groups, 2,4-dimethylphenyl groups, 2,5-dimethylphenyl groups, 2,6-dimethylphenyl groups, 3,4-dimethylphenyl groups, 3,5-dimethylphenyl groups, 2,4,6-trimethylphenyl groups, 2-methyl-6-ethylphenyl groups, 2,6-diethylphenyl groups, o-isopropylphenyl groups, m-isopropylphenyl groups, p-isopropylphenyl groups, 2-methyl-6-isopropylphenyl groups, 4-butylphenyl groups, o-tert-butylphenyl groups, m-tert-butylphenyl groups, and p-tert-butylphenyl groups; Examples include alkenylaryl groups such as 4-vinylphenyl groups; etc.

[0059] The above hydrocarbon group having 1 to 10 carbon atoms may be a combination of two or more of the chain hydrocarbon group, alicyclic hydrocarbon group, and aromatic hydrocarbon group listed above, provided that the upper limit of the number of carbon atoms is 10. Such groups include, for example, aralkyl groups such as benzyl group, phenethyl group, 1-methyl-1-phenylethyl group; aryl alkenyl groups such as phenylethenyl group (phenylvinyl group); and aryl alkenyl groups such as phenylethinyl group. 1-methylcyclopropyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, Examples include a cyclocyclic hydrocarbon group to which one or more alkyl groups, such as a 3,3,5,5-tetramethylcyclohexyl group, or a cyclocyclic hydrocarbon group is bonded; an alkyl group to which one or more cyclocyclic hydrocarbon groups, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, etc., are bonded.

[0060] The substituents that the above C1- to C0 hydrocarbon group may have (hereinafter referred to as substituent A) include a halogen atom, a hydroxyl group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, -SO3 - At least one selected from the group consisting of , and -SO3M, where M represents a hydrogen atom or an alkali metal atom.

[0061] Examples of the above halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0062] Examples of the above alkoxy groups include carbon 1 to 4 alkoxy groups such as methoxy groups, ethoxy groups, propoxy groups, and butoxy groups.

[0063] As the above-mentioned substituted amino group, an amino group having one or two hydrocarbon groups may be cited, and as the above-mentioned hydrocarbon group, a group exemplified as a hydrocarbon group having 1 to 10 carbon atoms as described above may be cited. Examples of substituted amino groups include N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diisopropylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N-methylphenylamino group, N,N-ethylphenylamino group, etc.

[0064] Examples of the above alkali metal atoms include sodium, potassium, etc.

[0065] R 5 ~R 12 Examples of halogen atoms represented by this include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0066] R 5 ~R 12 Examples of hydrocarbon groups having 1 to 5 carbon atoms represented by include aliphatic hydrocarbon groups having 1 to 5 carbon atoms, and specifically, the aforementioned R 1 ~R 4 and R 13 Among the groups exemplified as aliphatic hydrocarbon groups, groups having 1 to 5 carbon atoms can be cited.

[0067] As a substituent that the above-mentioned hydrocarbon group having 1 to 5 carbon atoms may have, the group exemplified as substituent A can be cited.

[0068] T 1 and T 2A divalent aromatic hydrocarbon group represented by is a group in an aromatic hydrocarbon ring in which two hydrogen atoms directly bonded to a carbon atom constituting the ring are substituted by bonding hands. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group may be either a monocyclic or a condensed ring; examples include benzene rings, naphthalene rings, anthracene rings, and structures in which at least one hydrogen atom of the aromatic hydrocarbon ring is substituted by a hydrocarbon group. As the above-mentioned hydrocarbon group, the R described above 1 ~R 4 and R 13 Examples of hydrocarbon groups having 1 to 10 carbon atoms, represented by [formula], may be given as exemplified groups, preferably saturated chain hydrocarbon groups, aryl groups, or alkylaryl groups, and more preferably saturated chain hydrocarbon groups having 1 to 4 carbon atoms. The number of hydrocarbon groups bonded to the aromatic hydrocarbon ring is preferably 0 to 4, and more preferably 0 to 3. As divalent aromatic hydrocarbon groups, specifically, groups represented by the following formulas (Ta-1) to (Ta-8) may be given.

[0069] [Chemical Formula 6]

[0070]

[0071] T 2 A divalent aromatic complex ring group represented by is a group in an aromatic complex ring in which two hydrogen atoms directly bonded to atoms constituting the ring are substituted by bonding hands. The aromatic complex ring constituting the divalent aromatic complex ring group may be either a monocyclic ring or a condensed ring; examples include pyrrole rings, oxazole rings, pyrazol rings, imidazole rings, thiazole rings, furan rings, thiophene rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, indole rings, benzimidazole rings, benzothiazole rings, quinoline rings, benzofuran rings, and structures in which at least one hydrogen atom of such aromatic complex rings is substituted by a hydrocarbon group. As the above hydrocarbon group, the R described above 1 ~R 4 and R 13Examples of hydrocarbon groups having 1 to 10 carbon atoms, represented by [the example], may be given, preferably saturated chain hydrocarbon groups, aryl groups, or alkylaryl groups. The number of hydrocarbon groups bonded to the aromatic heterocyclic ring is preferably 0 to 4, and more preferably 0 to 3.

[0072] As substituents that may be present in the above divalent aromatic hydrocarbon group and divalent aromatic complex group, the group exemplified as substituent A can be cited.

[0073] L 1 An aliphatic hydrocarbon group of α with 1 to 12 carbon atoms, represented by [formula], is a group in which a number of hydrogen atoms constituting the aliphatic hydrocarbon are substituted with bonding hands. It is preferable that the a number of bonding hands exist on different carbon atoms. Examples of aliphatic hydrocarbon groups of α include chain hydrocarbon groups of α, alicyclic hydrocarbon groups of α, and a combination of chain hydrocarbon groups and alicyclic hydrocarbon groups of α.

[0074] The chain hydrocarbon group of a may be saturated or unsaturated, but it is preferable that it be a saturated chain hydrocarbon group of a. Examples of saturated chain hydrocarbon groups of a include alkanedyl groups such as methylene groups, ethylene groups, propane-1,2-diyl groups, propane-1,3-diyl groups, butane-1,4-diyl groups, pentane-1,5-diyl groups, and hexane-1,6-diyl groups; alkanedriyl groups such as groups represented by the following formulas (a-1) to (a-2); and alkanetetaryyl groups such as groups represented by the following formula (a-3). The number of carbon atoms in the chain hydrocarbon group of a is preferably 1 to 8, and more preferably 1 to 6.

[0075] [Chemical Formula 7]

[0076]

[0077] The a-valent alicyclic hydrocarbon group may be saturated or unsaturated, but it is preferable that it be a saturated alicyclic hydrocarbon group. Examples of a saturated alicyclic hydrocarbon groups include divalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,2-diyl group, cyclohexyl-1,4-diyl group, norbornan-2,5-diyl group; trivalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,3,5-triyl group; tetravalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,2,4,5-tetrayl group; etc. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 10, and more preferably 3 to 6.

[0078] As for the a-value group combining a chain hydrocarbon group and an alicyclic hydrocarbon group, it is preferable that the a-value group combines at least one chain hydrocarbon group and at least one saturated alicyclic hydrocarbon group, and examples include the groups represented by the following formulas (a-4) to (a-7).

[0079] [Chemical Formula 8]

[0080]

[0081] As substituents that may be present in the aliphatic hydrocarbon group having 1 to 12 carbon atoms, the group exemplified as substituent A can be cited.

[0082] L 1 is the contribution represented by Equation (i).

[0083] In equation (i), T 3 An aromatic hydrocarbon group of a valence a, represented as such, is a group in which a number of hydrogen atoms directly bonded to carbon atoms constituting the ring are substituted with bonding hands. As for the aromatic hydrocarbon group constituting the aromatic hydrocarbon group of a valence a, the structure described as the aromatic hydrocarbon group constituting the aforementioned divalent aromatic hydrocarbon group can be cited.

[0084] In equation (i), T 3An aromatic complex group of a valence a, represented as such, is a group in which a number of hydrogen atoms directly bonded to the atoms constituting the ring are substituted with bonding hands. As for the aromatic complex groups constituting an aromatic complex group of a valence a, the structure described as the aromatic complex group constituting the aforementioned divalent aromatic complex group can be cited.

[0085] As substituents that may be present in the above aromatic hydrocarbon group and aromatic complex group of a, the group exemplified as substituent A can be cited.

[0086] In equation (i), L 2 Examples of divalent aliphatic hydrocarbon groups having 1 to 5 carbon atoms represented by this include divalent chain hydrocarbon groups having 1 to 5 carbon atoms and divalent alicyclic hydrocarbon groups having 1 to 5 carbon atoms.

[0087] The divalent chain hydrocarbon group may be saturated or unsaturated, but it is preferable that it be a divalent saturated chain hydrocarbon group. Examples of divalent saturated chain hydrocarbon groups include alkanedyl groups such as methylene groups, ethylene groups, propane-1,2-diyl groups, propane-1,3-diyl groups, butane-1,4-diyl groups, and pentane-1,5-diyl groups.

[0088] The divalent alicyclic hydrocarbon group may be saturated or unsaturated, but it is preferable that it be a divalent saturated alicyclic hydrocarbon group. Examples of divalent saturated alicyclic hydrocarbon groups include cyclopropyl-1,2-diyl group and cyclobutyl-1,3-diyl group.

[0089] As a substituent that the above divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms may have, the group exemplified as substituent A can be cited.

[0090] Specifically, the apparatus represented by Equation (i) can be the apparatus represented by the following Equation (i1) or (i2).

[0091] [Chemical Formula 9]

[0092]

[0093] [During the meal, L i1 ~L i5 Each independently represents a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms.

[0094] Among equations (i1) to (i2), L i1 and L i2 , and L i3 ~L i5 They may be the same or different, but it is preferable that they be the same.

[0095] X c- Examples of c-valence anions represented by [ ] include known anions, specifically halide ions such as fluoride ions, chloride ions, bromide ions, and iodide ions, boron-containing anions, aluminum-containing anions, fluorine-containing anions, and anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as an essential element.

[0096] Examples of boron-containing anions and aluminum-containing anions include anions represented by the following formula (4).

[0097] [Chemical Formula 10]

[0098]

[0099] [Equation (4), W 1 , W 2 represents a group having two substituents, each independently formed by releasing a proton from a monovalent proton-donating substituent. M represents boron or aluminum.

[0100] As a group having two substituents formed by releasing a proton from a monovalent proton-donating substituent, examples include a group formed by releasing a proton from each of the two proton-donating substituents from a compound having at least two monovalent proton-donating substituents (e.g., a hydroxyl group, a carboxylic acid group, etc.). Preferably, the said compound is catechol that may have a substituent, 2,3-dihydroxynaphthalene that may have a substituent, 2,2'-biphenol that may have a substituent, 3-hydroxy-2-naphthoic acid that may have a substituent, 2-hydroxy-1-naphthoic acid that may have a substituent, 1-hydroxy-2-naphthoic acid that may have a substituent, binaphthol that may have a substituent, salicylic acid that may have a substituent, benzilic acid that may have a substituent, or mandelic acid that may have a substituent.

[0101] In the compounds of the above examples, substituents may include saturated hydrocarbon groups (e.g., alkyl groups, cycloalkyl groups, etc.), halogen atoms, haloalkyl groups, hydroxyl groups, amino groups, nitro groups, alkoxy groups, etc.

[0102] As salicylic acids that may have substituents, monoaminosalicylic acids such as salicylic acid, 3-methylsalicylic acid, 3-tert-butylsalicylic acid, 3-methoxysalicylic acid, 3-nitrosalicylic acid, 4-trifluoromethylsalicylic acid, 3,5-di-tert-butylsalicylic acid, 3-aminosalicylic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid; monohydroxysalicylic acids such as 3-hydroxysalicylic acid (2,3-dihydroxycyanoic acid), 4-hydroxysalicylic acid (2,4-dihydroxycyanoic acid), 5-hydroxysalicylic acid (2,5-dihydroxycyanoic acid), and 6-hydroxysalicylic acid (2,6-dihydroxycyanoic acid); Examples include dihydroxysalicylic acids such as 4,5-dihydroxysalicylic acid and 4,6-dihydroxysalicylic acid; monohalosalic acids such as 3-chlorosalicylic acid, 4-chlorosalicylic acid, 5-chlorosalicylic acid, 6-chlorosalicylic acid, 3-bromosalicylic acid, 4-bromosalicylic acid, 5-bromosalicylic acid, and 6-bromosalicylic acid; dihalosalic acids such as 3,5-dichlorosalicylic acid, 3,5-dibromosalicylic acid, and 3,5-diiodosalicylic acid; and trihalosalic acids such as 3,5,6-trichlorosalicylic acid.

[0103] As for benzilic acid that may have substituents,

[0104] [Chemical Formula 11]

[0105]

[0106] As for mandelic acid that may have substituents,

[0107] [Chemical Formula 12]

[0108]

[0109] You can lift the back.

[0110] Among the preferred anions represented by formula (4), there are anions represented by the following formulas, and anions (BC-1) to anions (BC-24) having substituents listed in Table 1, and anions (BC-25) to anions (BC-28) represented by formulas (BC-25), (BC-26), (BC-27), and (BC-28), respectively.

[0111] [Chemical Formula 13]

[0112]

[0113] [Table 1]

[0114]

[0115] [Chemical Formula 14]

[0116]

[0117] [Chemical Formula 15]

[0118]

[0119] [Chemical Formula 16]

[0120]

[0121] [Chemical Formula 17]

[0122]

[0123] In terms of solubility in organic solvents, as anion represented by formula (4), anion (BC-1), anion (BC-2), anion (BC-3), anion (BC-25), anion (BC-26), and anion (BC-27) are preferred, anion (BC-1), anion (BC-2), and anion (BC-25) are more preferred, and anion (BC-1) and anion (BC-2) are more preferred.

[0124] Examples of fluorine-containing anions include those represented by the following formulas (6), (7), (8), and (9).

[0125] [Chemical Formula 18]

[0126]

[0127] [Equation (6), W 3 and W 4 Each independently represents a fluorine atom or a carbon-1 to carbon-4 fluoroalkyl group, or, W 3 and W 4 Together, they represent a fluorinated alkanedic group with 1 to 4 carbon atoms.

[0128] [Chemical Formula 19]

[0129]

[0130] [Equation (7), W 5 ~W 7 Each represents, independently, a fluorine atom or a carbon-1 to carbon-4 alkyl fluoride group.

[0131] [Chemical Formula 20]

[0132]

[0133] [Equation (8), Y 1 It represents a fluorinated alkanedial group having 1 to 4 carbon atoms.

[0134] [Chemical Formula 21]

[0135]

[0136] [Equation (9), Y 2 represents a fluoroalkyl group having 1 to 4 carbon atoms.

[0137] In formulas (6), (7) and (9), a perfluoroalkyl group having 1 to 4 carbon atoms is preferred as the fluoroalkyl group. Examples of such perfluoroalkyl groups include -CF3, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -CF2CF2CF2CF3, -CF2CF(CF3)2, -C(CF3)3, etc.

[0138] In formulas (6) and (8), a perfluoroalkanedyl group having 1 to 4 carbon atoms is preferred as the fluorinated alkanedyl group. Examples of perfluoroalkanedyl groups include -CF2-, -CF2CF2-, -CF2CF2CF2-, -C(CF3)2-, -CF2CF2CF2CF2-, etc.

[0139] As for the anions represented by Equation (6) (hereinafter referred to as “anion (6)”), examples include the anions represented by Equations (6-1) to (6-6) respectively (hereinafter referred to as “anion (6-1)” to “anion (6-6)”).

[0140] [Chemical Formula 22]

[0141]

[0142] An anion represented by Equation (7) (hereinafter referred to as “anion (7)”) is an anion (7-1) represented by the following Equation.

[0143] [Chemical Formula 23]

[0144]

[0145] Anions represented by Equation (8) (hereinafter referred to as “anion (8)”) include anions represented by Equations (8-1) to (8-4) respectively (hereinafter referred to as “anion (8-1)” to “anion (8-4)”).

[0146] [Chemical Formula 24]

[0147]

[0148] Anions represented by Equation (9) (hereinafter referred to as “anion (9)”) include anions represented by Equations (9-1) to (9-4) respectively (hereinafter referred to as “anion (9-1)” to “anion (9-4)”).

[0149] [Chemical Formula 25]

[0150]

[0151] X c- The solubility of compound (I) in an organic solvent can be improved by the fact that the anion of c represented by is at least one anion (i.e., a fluorine-containing anion) selected from the group consisting of anion (6), anion (7), anion (8) and anion (9). Among these, anion (6-1), anion (6-2), and anion (7-1) are preferred, and anion (6-2) is particularly preferred.

[0152] X c- As an anion of c represented by, examples include an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as an essential element, and an anion of a heteropoly acid or isopoly acid containing tungsten as an essential element is preferred, and anions of phosphotungstic acid, silicotungstic acid, and tungsten-based isopoly acid are more preferred.

[0153] As an anion of a heteropolyacid or isopolyacid containing such tungsten as an essential element, for example, the Keggine-type phosphotungstate ion α-[PW 12 O 40 ] 3- , Dawson-type phosphotungstate ion α-[P2W 18 O 62 ] 6- , β-[P2W 18 O 62 ] 6- , Keggin-type tungstate ion α-[SiW 12 O 40 ] 4- , β-[SiW 12 O 40 ] 4- , γ-[SiW 12 O 40 ] 4- , also as an example of others [P2W 17 O 61 ] 10- , [P2W 15 O 56 ] 12-, [H2P2W 12 O 48 ] 12- , [NaP5W 30 O 110 ] 14- , α-[SiW9O 34 ] 10- , γ-[SiW 10 O 36 ] 8- , α-[SiW 11 O 39 ] 8- , β-[SiW 11 O 39 ] 8- , [W6O 19 ] 2- , [W 10 O 32 ] 4- , WO4 2- You can lift the back.

[0154] In addition, among anions other than those of heteropolyacid or isopolyacid containing tungsten as an essential element, an anion consisting of at least one element selected from the group consisting of silicon and phosphorus and oxygen is preferred.

[0155] As an anion consisting of at least one element selected from the group consisting of silicon and phosphorus, and oxygen, SiO3 2- , PO4 3- ...can be cited.

[0156] In particular, due to the ease of synthesis and post-processing, heteropolyacid anions such as Keggin-type phosphotungstate ions, Dawson-type phosphotungstate ions, and Keggin-type silicic acid ions, [W 10 O 32 ] 4- Isopolyacid anion is preferred.

[0157] In equation (I), multiple R 1 ~R 13 , T 1 , T 2 , and L 1 They may be the same or different, but it is preferable that they be the same.

[0158] R 1 ~R 4 It is preferable that each is independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms that may have a substituent, an aryl group having 6 to 10 carbon atoms that may have a substituent, or an alkylaryl group having 7 to 10 carbon atoms that may have a substituent.

[0159] In particular, R 1 and R 3 Each of these is independently an aryl group having 6 to 10 carbon atoms that may have a substituent, or an alkylaryl group having 7 to 10 carbon atoms that may have a substituent, and also, R 2 and R 4 a. It is preferable that each independently be a saturated chain hydrocarbon group having 1 to 10 carbon atoms, which may have a substituent, and

[0160] R 1 and R 3 This is a phenyl group that may have a substituent, each independently, and also, R 2 and R 4 a. It is more preferable that each independently be a saturated chain hydrocarbon group having 1 to 10 carbon atoms, which may have a substituent, and

[0161] R 1 and R 3 Each of these is a phenyl group that may independently have a substituent, wherein at least one of two bonding positions that are ortho-positioned with respect to N bonded to the phenyl group has an alkyl group having 1 to 4 carbon atoms, and furthermore, R 2 and R 4 a. It is more preferable that each independently be a saturated chain hydrocarbon group having 1 to 6 carbon atoms that may have a substituent, and

[0162] R 1 and R 3Each of these is a phenyl group that may independently have a substituent, wherein at least one of two bonding positions that are ortho-positioned with respect to N bonded to the phenyl group has an alkyl group having 1 to 4 carbon atoms, and furthermore, R 2 and R 4 a. It is more preferable that each independently be a saturated chain hydrocarbon group having 2 to 6 carbon atoms, which may have a substituent, and

[0163] R 1 and R 3 This is a phenyl group that may each independently have a substituent, and is a group having an alkyl group having 1 to 3 carbon atoms at each of two bonding positions that are ortho positions with respect to N bonded to the phenyl group, and also R 2 and R 4 a. It is particularly preferable that each be a saturated chain hydrocarbon group having 2 to 6 carbon atoms, which may have a substituent independently.

[0164] Here, the substituents that the phenyl group may have include an alkyl group having 1 to 4 carbon atoms, a halogen atom, a hydroxyl group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, -SO3 - Examples include at least one selected from the group consisting of , and -SO3M (M is the same as above), among which, an alkyl group having 1 to 4 carbon atoms, a halogen atom, an alkoxy group, and -SO3 - At least one selected from the group consisting of, wherein a C1-4 alkyl group, a C1-4 alkoxy group, and -SO3 - At least one selected from the group consisting of is more preferable.

[0165] In particular, the phenyl group does not have a substituent, or as a substituent, an alkyl group having 1 to 4 carbon atoms, a halogen atom, a hydroxyl group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, -SO3 -Only at least one substituent selected from the group consisting of , and -SO3M (preferably an alkyl group having 1 to 4 carbon atoms and -SO3 - If it has at least one substituent selected from the group consisting of, the brightness of the resulting color filter can be increased.

[0166] In addition, when the above phenyl group has an alkoxy group (preferably a methoxy group) as a substituent, light resistance can be improved. The substitution position of the above alkoxy group (preferably a methoxy group) is not particularly limited, but by attaching it to a position that is para position with respect to N attached to the phenyl group, the light resistance improvement effect can be further enhanced.

[0167] Tactical R 1 ~R 4 In the desirable sun of, R 1 and R 3 It is particularly preferable that each is independently any of the groups represented by formulas (r1) to (r3). In addition, at least one of the hydrogen atoms of the groups represented by formulas (r1) to (r3) is -SO3 - It may be substituted by.

[0168] [Chemical Formula 26]

[0169]

[0170] [In the middle of the meal, R r1 ~R r4 Each represents, independently, an alkyl group having 1 to 4 carbon atoms. * represents a bond loss.]

[0171] R r1 ~R r4 It is preferable that it be a methyl group.

[0172] R 5 ~R 12 It is preferable that it be a hydrogen atom.

[0173] R 13It is preferable that it be a hydrocarbon group having 1 to 6 carbon atoms that may have a hydrogen atom or a substituent, more preferably a saturated chain hydrocarbon group having 1 to 6 carbon atoms that may have a hydrogen atom or a substituent, and even more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, or an isopropyl group.

[0174] T 1 As for the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group represented by, it is preferable that the ring be a benzene ring, a naphthalene ring, or have a structure in which at least one hydrogen atom of the ring is substituted with a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4). 1 As such, it is more preferable to be any of the groups represented by the above formulas (Ta-1) to (Ta-8), and the group represented by the above formula (Ta-8) is particularly preferable.

[0175] T 2 It is preferable that the aromatic hydrocarbon group may have substituents, and as the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group, it is preferable that the ring be a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of the ring is substituted with a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms), and more preferable that the ring be a benzene ring or a structure in which at least one hydrogen atom of the benzene ring is substituted with a saturated chain hydrocarbon group having 1 to 4 carbon atoms. 2 As such, it is more preferable to be any of the groups represented by the following formulas (Tb-1) to (Tb-10), more preferable to be any of the groups represented by the following formulas (Tb-3), (Tb-5), (Tb-6), (Tb-9), and (Tb-10), and particularly preferable to be any of the groups represented by the following formulas (Tb-5), (Tb-6), (Tb-9), and (Tb-10).

[0176] [Chemical Formula 27]

[0177]

[0178] [In food, * is L 1 [Indicates the bond loss with, and ** indicates the bond loss with the nitrogen atom.]

[0179] L 1 ☐ is an aliphatic hydrocarbon group having 1 to 8 carbon atoms that may have substituents, or in the group represented by formula (i), T 3 It is an aromatic hydrocarbon group of a valence a that may have this substituent, and L 2 It is preferable that the group be a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, an alkanedyl group having 1 to 6 carbon atoms that may have substituents, a divalent saturated alicyclic hydrocarbon group having 3 to 10 carbon atoms that may have substituents, or a group represented by the above formula (i1) or (i2), and it is even more preferable that the group be an alkanedyl group having 1 to 6 carbon atoms that may have substituents, a divalent saturated alicyclic hydrocarbon group having 3 to 10 carbon atoms that may have substituents, or any of the groups represented by the following formulas (i-1) to (i-4).

[0180] [Chemical Formula 28]

[0181]

[0182] X c- As for the c-valence anion represented by, it is preferable that it be a halide ion or an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus and oxygen as an essential element, more preferable that it be a halide ion or an anion of a heteropolyacid or isopolyacid containing tungsten as an essential element, and more preferable that it be a halide ion, a Keggin-type phosphotungstate ion, or a Dawson-type phosphotungstate ion.

[0183] As a substituent of compound (I) (i.e., substituent A), a halogen atom, a hydroxyl group, an alkoxy group, a substituted or unsubstituted amino group, -SO3- It is preferable that at least one is selected from the group consisting of , and -SO3M, and more preferably a halogen atom, an alkoxy group, and -SO3 - It is at least one selected from the group consisting of , and -SO3M.

[0184] a is preferably an integer between 2 and 6, more preferably an integer between 2 and 4, and even more preferably 2 or 3.

[0185] c is typically 1 to 14, preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 4.

[0186] b and d are the -SO3 that a, c, and compound (I) have as substituents. - It is determined by the number of (hereinafter referred to as e), and generally, it is adjusted so that the total charge of Equation (I) becomes zero. Therefore, typically, a to d in Equation (I) satisfy the relationship of Equation (z) below.

[0187]

[0188] [In the above formulas, a to d have the same meaning as above. e is -SO3 that compound (I) has as a substituent. - Represents the number of.

[0189] e is an integer greater than or equal to 0, preferably greater than or equal to (a+1), more preferably greater than or equal to 0 and less than or equal to a, and even more preferably 0 or a. Particularly when d is greater than or equal to 1, e is 0, i.e., compound (I) is -SO3 - It is preferable not to have, and when d is 0, it is preferable that e = a.

[0190] In addition, from the perspective of heat resistance and solvent resistance, X c-A compound is preferred in which d is 1 or more and e is 0, and ga is an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus and oxygen as an essential element.

[0191] As for compound (I), it is preferable that it be a compound represented by formula (I-1) or formula (I-2).

[0192] [Chemical Formula 29]

[0193]

[0194] [Among the formula (I-1),

[0195] R 101 and R 103 These are phenyl groups that may each independently have a substituent, and

[0196] R 102 and R 104 a, each independently, is a saturated chain hydrocarbon group having 1 to 10 carbon atoms that may have a substituent, and

[0197] R 105 ~R 112 is a hydrogen atom, and

[0198] R 113 It is a saturated chain hydrocarbon group having 1 to 6 carbon atoms that may have silver, hydrogen atoms, or substituents, and

[0199] T 101 and T 102 is a divalent aromatic hydrocarbon group that may have substituents, wherein the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of the ring is substituted with a saturated chain hydrocarbon group having 1 to 4 carbon atoms, and

[0200] L 101 ☐ is an aliphatic hydrocarbon group having 1 to 8 carbon atoms and having an a101 valence that may have substituents, or in the group represented by formula (i), T 3It is an aromatic hydrocarbon group of a101 that may have this substituent, and L 2 ga is a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, and

[0201] a101 is 2 or 3, and

[0202] d101 represents an integer greater than or equal to 1, and

[0203] b, c, and X c- represents the same meaning as above.]

[0204] [Chemical Formula 30]

[0205]

[0206] [In the (I-2) formula,

[0207] R 201 and R 203 These are phenyl groups that may each independently have a substituent, and

[0208] R 202 and R 204 a, each independently, is a saturated chain hydrocarbon group having 1 to 10 carbon atoms that may have a substituent, and

[0209] R 205 ~R 212 is a hydrogen atom, and

[0210] R 213 It is a saturated chain hydrocarbon group having 1 to 6 carbon atoms that may have silver, hydrogen atoms, or substituents, and

[0211] T 201 and T 202 is a divalent aromatic hydrocarbon group that may have substituents, wherein the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of the ring is substituted with a saturated chain hydrocarbon group having 1 to 4 carbon atoms, and

[0212] L 201☐ is an a201 aliphatic hydrocarbon group having 1 to 8 carbon atoms that may have substituents, or in the group represented by formula (i), T 3 It is an aromatic hydrocarbon group of a201 that may have this substituent, and L 2 ga is a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, and

[0213] a201 and e201 are 2 or 3, and

[0214] The compound represented by formula (I-2) is R 201 ~R 213 , T 201 , T 202 , and L 201 Which of the hydrogen atoms in this, e201, are -SO3 - [Substituted by]

[0215] R 101 , R 103 , R 201 and R 203 As substituents that the phenyl group represented by [formula] may have, at least one may be selected from the group consisting of a C1-4 alkyl group, a halogen atom, a hydroxyl group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, and -SO3M (where M is a hydrogen atom or an alkali metal atom), and among these, at least one may be selected from the group consisting of a C1-4 alkyl group and a C1-4 alkoxy group. The halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described as substituent A.

[0216] R 101 , R 103 , R 201 and R 203It is a phenyl group that may have a substituent, and it is preferable that the phenyl group has an alkyl group having 1 to 4 carbon atoms at at least one (preferably both) of the two bonding positions that are ortho positions with respect to N bonded to the phenyl group. In particular, R 101 , R 103 , R 201 and R 203 It is preferable that each be any of the groups represented by the above formulas (r1) to (r3), independently, and from the perspective of improving brightness, it is more preferable that it be the group represented by the above formula (r1) or (r2), and from the perspective of improving light resistance, it is more preferable that it be the group represented by the above formula (r3).

[0217] R 102 , R 104 , R 202 and R 204 It is preferably a saturated chain hydrocarbon group having 1 to 6 carbon atoms that may have substituents, and more preferably a saturated chain hydrocarbon group having 2 to 6 carbon atoms. R 102 , R 104 , R 202 and R 204 As a substituent (hereinafter referred to as substituent B) that may be possessed by the saturated chain hydrocarbon group represented by, at least one may be selected from the group consisting of a halogen atom, a hydroxyl group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, and -SO3M (where M is a hydrogen atom or an alkali metal atom). The halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described for substituent A.

[0218] R 113 and R 213 As a substituent that may be possessed by the saturated chain hydrocarbon group having 1 to 6 carbon atoms represented by, the group described as substituent B can be cited.

[0219] T 101and T 201 As a substituent that the divalent aromatic hydrocarbon group represented by T may have, the group described as substituent B can be cited. 101 and T 201 As such, it is preferable that it be any of the groups represented by the above formulas (Ta-1) to (Ta-8), and more preferable that it be the group represented by the formula (Ta-8).

[0220] T 102 and T 202 As a substituent that the divalent aromatic hydrocarbon group represented by T may have, the group described as substituent B may be an example, and among these, at least one selected from the group consisting of halogen atoms and alkoxy groups is preferred. 102 and T 202 As a divalent aromatic hydrocarbon group that may have a substituent, it is preferable that the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group has a structure in which at least one hydrogen atom of the benzene ring is substituted with a saturated chain hydrocarbon group having 1 to 4 carbon atoms, it is more preferable that it be any of the groups represented by formulas (Tb-1) to (Tb-10), and particularly preferable that it be any of the groups represented by formulas (Tb-5), (Tb-6), (Tb-9), and (Tb-10).

[0221] In equations (I-1) and (I-2), L 101 and L 201 A saturated chain hydrocarbon group of α with 1 to 8 carbon atoms represented by T 3 An aromatic hydrocarbon group of a represented by , and L in formula (i). 2 As a substituent that may be present, the group described as substituent B can be cited. L 101 and L 201It is preferable that the group be an alkanedyl group having 1 to 6 carbon atoms that may have a substituent, a divalent saturated alicyclic hydrocarbon group having 3 to 10 carbon atoms that may have a substituent, or any of the groups represented by the above formula (i1) or (i2).

[0222] It is desirable that a201 and e201 be the same.

[0223] The compounds represented by formulas (I-1) and (I-2) preferably have a charge of 0.

[0224] In addition, from the perspective of heat resistance and solvent resistance, the compound represented by formula (I-1) is preferred.

[0225] Specifically, compounds (I) include compounds (I-1a-1) to (I-108a-1) and compounds (I-1a-2) to (I-108a-2) represented by the following formula (Ia), and compounds (I-1b) to (I-108b) represented by the following formula (Ib). Furthermore, the compound represented by formula (Ib) represents a compound among compounds (I) in which b is 1 and d is 0. The compound represented by formula (Ib) is R 1b ~R 13b , T 1b , T 2b , and L 1b Which of the two hydrogen atoms in -SO3 - It is substituted by.

[0226] [Chemical Formula 31]

[0227]

[0228] [Table 2]

[0229]

[0230] [Table 3]

[0231]

[0232] [Table 4]

[0233]

[0234] [Table 5]

[0235]

[0236] [Table 6]

[0237]

[0238] [Chemical Formula 32]

[0239]

[0240] [Table 7]

[0241]

[0242] [Table 8]

[0243]

[0244] [Table 9]

[0245]

[0246] In Tables 2 to 9, H represents a hydrogen atom, Et represents an ethyl group, and Pr represents an n-propyl group; r-1 to r-3 represent groups represented by the following formulas (r-1) to (r-3); Ta-8 represents a group represented by the following formula (Ta-8); Tb-5 to Tb-6 and Tb-9 to Tb-10 represent groups represented by the following formulas (Tb-5) to (Tb-6) and (Tb-9) to (Tb-10); l-1 represents a group represented by the following formula (l-1); and i-2 and i-4 represent groups represented by the following formulas (i-2) and (i-4).

[0247] [Chemical Formula 33]

[0248]

[0249] [In the formula, * indicates a bond loss with a nitrogen atom.]

[0250] [Chemical Formula 34]

[0251]

[0252] [In the formula, * indicates a bond.]

[0253] [Chemical Formula 35]

[0254]

[0255] [In food, * is L 1a or L 1b [Represents the bond loss with, and ** represents the bond loss with the nitrogen atom.]

[0256] [Chemical Formula 36]

[0257]

[0258] [In food, * is T 2a or T 2b [Represents the bonding loss with.]

[0259] As compound (I), compounds (I-1a-1) to (I-36a-1), compounds (I-1a-2) to (I-36a-2), compounds (I-55a-1) to (I-90a-1), compounds (I-55a-2) to (I-90a-2), compounds (I-1b) to (I-36b), and compounds (I-55b) to (I-90b) are preferred, and compounds (I-1a-1) to (I-18a-1), compounds (I-55a-1) to (I-72a-1), compounds (I-1a-2) to (I-18a-2), compounds (I-55a-2) to (I-72a-2), compounds (I-1b) to (I-18b), and compounds (I-55b) to (I-72b) are more preferred, and compounds (I-1a-2) to (I-18a-2), compounds (I-55a-2) to (I-72a-2), compounds (I-1b) to (I-18b), and compounds (I-55b) to (I-72b) are more preferable. From the perspective of improving lightness, R 1a , R 3a , R 1b , R 3b A compound represented by formula (r-1) or (r-2) is preferred, and in terms of improving light resistance, R 1a , R 3a , R 1b , R 3bA compound represented by formula (r-3) is preferred. Furthermore, from the viewpoint of heat resistance and solvent resistance, compounds (I-1a-2) to (I-108a-2) are preferred, and compounds (I-1a-2) to (I-18a-2) and compounds (I-55a-2) to (I-72a-2) are more preferred.

[0260] Compound (I) can be prepared, for example, by the following methods (1) to (3).

[0261] (1) X c- A method for preparing a compound (I) in which α is a halide ion (hereinafter referred to as compound (I').

[0262] Compound (I') can be prepared, for example, by reacting a compound represented by formula (BI) with a compound represented by formula (CI).

[0263] [Chemical Formula 37]

[0264]

[0265] [Among formulas (BI) and (CI), R 1 ~R 13 , T 2 , L 1 , and a each represent the same meaning as above. T 1B is, the above T 1 In this context, it represents a group in which a bonding hand different from the one bonded to the nitrogen atom is substituted with a hydrogen atom.

[0266] The amount of compound represented by formula (CI) used is preferably 0.5 moles or more and 10 moles or less, and more preferably 1 mole or more and 4 moles or less, for every 1 mole of compound represented by formula (BI).

[0267] The reaction temperature is preferably 30℃ to 180℃, and more preferably 80℃ to 130℃. The reaction time is preferably 1 hour to 12 hours, and more preferably 1 hour to 8 hours.

[0268] The above reaction may be carried out in the presence of an organic solvent or without a solvent, but for the sake of yield, it is preferable to carry out the reaction 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; nitrohydrocarbon solvents such as nitrobenzene; ketone solvents such as methylisobutylketone; and amide solvents such as 1-methyl-2-pyrrolidone. The amount of organic solvent used is preferably 1 part by mass or more and 20 parts by mass or less, and more preferably 2 parts by mass or more and 10 parts by mass or less, per 1 part by mass of the compound represented by formula (BI).

[0269] From the perspective of yield, it is preferable to carry out the above reaction in the presence of a condensing agent. Examples of condensing agents include phosphoric acid, polyphosphoric acid, phosphorus oxychloride (oxyhalogenated phosphorus), sulfuric acid, thionyl halides (thionyl chloride), etc. In the case where phosphorus oxyhalides, thionyl halides, etc. are used as condensing agents, if the relationship of Equation (z1) is satisfied, X c- A compound (I') in which is a halide ion is obtained.

[0270]

[0271] [In the above formulas, a and b have the same meaning as a and b in formula (I). e is -SO3 that compound (I') has as a substituent. - Represents the number of.

[0272] The amount of condensing agent used is preferably 0.1 parts by mass or more and 20 parts by mass or less, and more preferably 0.2 parts by mass or more and 10 parts by mass or less, per 1 part by mass of the compound represented by formula (BI).

[0273] The method for obtaining compound (I') from the reaction mixture is not particularly limited, and various known methods may be employed. After extraction, the obtained residue may be purified by column chromatography or recrystallization, etc.

[0274] As a method for preparing the compound (BI), various known methods may be used, for example, the method described in West German Patent Application P3928243.0. Additionally, if necessary, further purification may be performed by known methods such as recrystallization or fractionation by chromatography.

[0275] Various known methods can be used to prepare the compound (Cl). Additionally, if necessary, further purification may be performed by known methods such as recrystallization or fractionation by chromatography.

[0276] (2) X c- anion other than a halide ion (hereinafter, anion X) 1 A method for preparing compound (I) (hereinafter referred to as compound (I'')).

[0277] Compound (I'') is compound (I') and anion X 1 It can be prepared by mixing an alkali metal salt or a proton acid. Examples of alkali metals include lithium, sodium, and potassium.

[0278] Anion X for compound (I') 1 The amount of alkali metal salt or proton acid used is the cation and anion X in compound (I'). 1 It can be added in a stoichiometric ratio such that the charges are balanced, for example, for 1 mole of compound (I'), preferably 0.5 moles or more and 8 moles or less, and more preferably 1 mole or more and 3 moles or less.

[0279] Compound (I') and anion X 1Mixing with alkali metal salts or proton acids may be carried out by dissolving both in the following solvent, or without dissolving them.

[0280] Examples of solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, acetonitrile, ethyl acetate, toluene, methanol, ethanol, isopropanol, acetone, tetrahydrofuran, dioxane, water, and chloroform.

[0281] Among these, in terms of solubility, at least one solvent selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, methanol, ethanol, isopropanol, and water is preferred.

[0282] The amount of solvent used is preferably 1 part by mass or more and 30 parts by mass or less, and more preferably 2 parts by mass or more and 20 parts by mass or less, per 1 part by mass of compound (I').

[0283] If the solvent is water, acids such as acetic acid or hydrochloric acid may be added.

[0284] Compound (I') and anion X 1 The mixing temperature with the alkali metal salt or proton acid is preferably 0°C to 150°C, more preferably 10°C to 120°C, and even more preferably 20°C to 100°C. The mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 24 hours, and even more preferably 3 hours to 12 hours.

[0285] When using a solvent compatible with water, the solution can be mixed and, if necessary, stirred for an additional 1 to 3 hours, after which the solvent can be removed to obtain compound (I''). If necessary, the obtained compound (I'') may be washed with ion-exchanged water or methanol.

[0286] In the case where a solvent incompatible with water is used, the reaction mixture and ion-exchanged water are mixed and stirred for an additional 1 to 3 hours if necessary, and then the organic layer is obtained by separation to obtain a solution containing compound (I''). If necessary, the solution may be washed with ion-exchanged water. Compound (I'') can be obtained by removing the solvent from the solution containing compound (I'').

[0287] (3) X c- A method for preparing a compound in which is not present (i.e., d=0) (hereinafter referred to as compound (I''')).

[0288] Compound (I''') can be prepared by mixing compound (I') with sulfuric acid.

[0289] The amount of sulfuric acid used for compound (I') is the cation in compound (I') and -SO3 - It may be added in a stoichiometric ratio such that the charges are balanced, for example, 0.5 moles or more and 8 moles or less per 1 mole of compound (I'), preferably 1 mole or more and 3 moles or less. In addition, the above sulfuric acid may be used as a reaction solvent, and when sulfuric acid is used as a solvent, the amount of sulfuric acid used is, for example, 20 moles or more, preferably 25 moles or more per 1 mole of compound (I'). In addition, when sulfuric acid is used as a solvent, the upper limit of the amount of sulfuric acid used is not particularly limited, but is, for example, 100 parts by mass or less, preferably 50 parts by mass or less per 1 part by mass of compound (I').

[0290] The mixing temperature of compound (I') and sulfuric acid is preferably 0°C to 150°C, more preferably 10°C to 120°C, and even more preferably 20°C to 100°C. The mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 24 hours, and even more preferably 3 hours to 12 hours.

[0291] A mixture obtained by mixing compound (I') with sulfuric acid can be added to ice water to form a suspension, and then filtered to obtain compound (I'''). Additionally, if necessary, it may be further purified by known methods such as recrystallization or fractionation by chromatography.

[0292] Colored Resin Composition >

[0293] The colored resin composition of the present invention contains a coloring agent (hereinafter referred to as coloring agent (A)) and a resin (hereinafter referred to as resin (B)), wherein the coloring agent comprises compound (I).

[0294] The colored resin composition of the present invention preferably further comprises a polymerizable compound (hereinafter referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter referred to as polymerization initiator (D)).

[0295] The colored resin composition of the present invention preferably further comprises a solvent (hereinafter referred to as solvent (E)).

[0296] The colored resin composition of the present invention may additionally include a leveling agent (hereinafter referred to as leveling agent (F)).

[0297] In addition, in this specification, the compounds exemplified as each component may be used alone or in combination of multiple types, unless specifically mentioned otherwise.

[0298] < Colorant (A) >

[0299] The coloring agent (A) contains compound (I). By doing so, the brightness of the resulting color filter is improved, and preferably, the resulting color filter can be made into a thin film. As for compound (I), the compound (I) described above may be used, and the preferred embodiment is the same.

[0300] Colorant (A) may include a dye other than compound (I) (hereinafter referred to as dye (A1-1)) and / or a pigment (hereinafter referred to as pigment (A1-2)). Hereinafter, dye (A1-1) and pigment (A1-2) may be collectively referred to as colorant (A1). These may be used individually or in combination of two or more types.

[0301] As long as the dye (A1-1) does not contain compound (I), any known dye may be used without particular limitation, and examples include solvent dyes, acid dyes, direct dyes, mordant dyes, etc. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) or known dyes listed in dyeing notes (Shikisensha). In addition, based on chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squaryllium dyes, acridin dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Among these, organic solvent-soluble dyes are preferred.

[0302] As a dye (A1-1), specifically,

[0303] CI Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;

[0304] CI Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;

[0305] CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;

[0306] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0307] CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 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;

[0308] CI solvent dyes such as CI solvent greens 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35;

[0309] 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;

[0310] 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;

[0311] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

[0312] CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

[0313] CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 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, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;

[0314] CI acid greens 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; and other CI acid dyes,

[0315] CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;

[0316] 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;

[0317] CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0318] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0319] 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, 87, 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;

[0320] CI Direct dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; etc.

[0321] CI Dispers Yellow 51, 54, 76;

[0322] CI Dispers Violet 26, 27;

[0323] CI Disperse dyes such as CI Disperse Blue 1, 14, 56, 60, etc.

[0324] CI Basic Red 1, 9, 10;

[0325] 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;

[0326] CI Basic Violet 2;

[0327] CI Basic Green 1; CI Basic dyes, etc.

[0328] CI Reactive Yellow 2, 76, 116;

[0329] CI Reactive Orange 16;

[0330] CI reactive dyes such as CI reactive red 36;

[0331] CI Modernt Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0332] CI Modernt 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;

[0333] CI Mordaunt Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0334] CI Modernt Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;

[0335] CI Modern 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;

[0336] CI Mordaunt Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; etc. CI Mordaunt dyes,

[0337] Examples of dyes with a color index (CI) number include CI Bat Green 1; CI Bat dyes, etc.

[0338] As for the pigment (A1-2), any known pigment may be used without being particularly limited, as long as it does not contain compound (I), and examples include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0339] As pigments classified as pigments, for example, yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231;

[0340] CI pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc. orange pigments;

[0341] CI pigment red pigments such as 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273;

[0342] CI pigment blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc. blue pigments;

[0343] Violet pigments such as CI pigments Violet 1, 19, 23, 32, 36, 38;

[0344] Green pigments such as CI pigment green 7, 36, 58, 59, 62, 63, etc.;

[0345] Brown pigments such as CI Pigment Brown 23, 25, etc.;

[0346] Examples include black pigments such as CI pigment black 1, 7, etc.

[0347] As a coloring agent (A1), yellow, red, or green dyes and / or pigments are preferred.

[0348] The coloring agent (A1) may, if necessary, undergo rosin treatment, surface treatment using derivatives having acidic or basic groups introduced, graft treatment on the surface of the coloring agent (A1) using polymer compounds, micronization treatment using sulfuric acid micronization method, washing treatment using organic solvents or water to remove impurities, or removal treatment using ion exchange method for ionic impurities. It is preferable that the particle size of the coloring agent (A1) be approximately uniform.

[0349] When the coloring agent (A) additionally includes coloring agent (A1), the content of compound (I) is, for example, 1 mass% or more, preferably 2 mass% or more, more preferably 10 mass% or more, even more preferably 25 mass% or more, and particularly preferably 50 mass% or more with respect to the total amount of coloring agent (A). Also, when the coloring agent (A) additionally includes coloring agent (A1), the content of compound (I) is, for example, less than 100 mass% with respect to the total amount of coloring agent (A).

[0350] If the colored resin composition contains a solvent (E), the colored resin composition may be prepared by first preparing a colored agent-containing solution containing the colored agent (A) and the solvent (E), and then using the said colored agent-containing solution. If the colored agent (A) does not dissolve in the solvent (E), for example, if the colored agent (A) contains a pigment (A1-2), the colored agent-containing solution may be prepared by dispersing the colored agent (A) in the solvent (E) and mixing it. The colored agent-containing solution may contain part or all of the solvent (E) contained in the colored resin composition.

[0351] The content of solids in the coloring agent-containing liquid is, with respect to the total amount of the coloring agent-containing liquid, preferably 0.01 mass% or more and 99.99 mass% or less, more preferably 0.1 mass% or more and 99.9 mass% or less, even more preferably 0.1 mass% or more and 99 mass% or less, even more preferably 0.5 mass% or more and 90 mass% or less, and particularly preferably 1 mass% or more and 50 mass% or less.

[0352] The coloring agent (A) may be uniformly dispersed in the solution by performing a dispersion treatment with a dispersant. When two or more types of coloring agents (A) are used in combination, each may be dispersed individually, or multiple types may be mixed and dispersed.

[0353] Examples of dispersants include surfactants, and may be cationic, anionic, nonionic, or amphoteric surfactants. Specifically, examples include polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants may be used individually or in combination of two or more types. Examples of dispersants, by trade name, include KP (Shin-Etsu Chemical Co., Ltd.), Floren (Kyoeisha Chemical Co., Ltd.), Solspers (registered trademark) (Zeneca Co., Ltd.), EFKA (registered trademark) (BASF), Azispar (registered trademark) (Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (Big Chem Co., Ltd.), and BYK (registered trademark) (Big Chem Co., Ltd.). As a dispersant, the resin (B) described below may be used.

[0354] When a dispersant is used, the amount of said dispersant (solid content) used is typically 1 part by mass or more and 10,000 parts by mass or less, preferably 5 parts by mass or more and 5,000 parts by mass or less, more preferably 10 parts by mass or more and 1,000 parts by mass or less, and even more preferably 15 parts by mass or more and 800 parts by mass or less, per 100 parts by mass of colorant (A). When the amount of said dispersant used is within the above range, a colorant-containing liquid with a more uniform dispersion state tends to be obtained.

[0355] The content of the coloring agent (A) is preferably 0.1 mass% or more and 50 mass% or less with respect to the total amount of solids of the coloring resin composition, more preferably 0.5 mass% or more and 40 mass% or less, and even more preferably 1 mass% or more and 30 mass% or less. If the content of the coloring agent (A) is within the above range, the color concentration when used as a color filter is sufficient, and since the resin (B) can be included in the composition in the required amount, it is desirable to be able to form a pattern with sufficient mechanical strength.

[0356] Herein, the term "total amount of solids" in this specification refers to the amount excluding the solvent content from the total amount of the colored resin composition. The total amount of solids and the content of each component therewith can be measured by known analytical means, such as liquid chromatography or gas chromatography.

[0357] < Suzy (B) >

[0358] The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6].

[0359] Resin [K1]; a copolymer having a structural unit derived from at least one monomer (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter referred to as “(a)”) and a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter referred to as “(b)”);

[0360] Resin [K2]; a copolymer having a structural unit derived from (a) and a structural unit derived from (b), and a structural unit derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter referred to as “(c)”);

[0361] Resin [K3]; a copolymer having a structural unit derived from (a) and a structural unit derived from (c);

[0362] Resin [K4]; a copolymer having a structural unit derived from (a) to which (b) is added and a structural unit derived from (c);

[0363] Resin [K5]; a copolymer having a structural unit derived from (b) to which (a) is added and a structural unit derived from (c);

[0364] Resin [K6]; a copolymer having a structural unit derived from (b) with (a) added, a structural unit with an additionally added carboxylic acid anhydride, and a structural unit derived from (c).

[0365] As monomer (a), unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid and o-, m-, p-vinyl benzoic acid;

[0366] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid;

[0367] Bicyclounsaturated compounds containing carboxyl groups, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-en, 5,6-dicarboxybicyclo[2.2.1]hept-2-en, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-en, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-en, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-en;

[0368] Carbolic anhydrides, such as the anhydrides of the above-mentioned unsaturated dicarboxylic acids excluding fumaric acid and mesaconic acid;

[0369] Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polycarboxylic acids, such as succinate mono[2-(meth)acryloyloxyethyl] and phthalate mono[2-(meth)acryloyloxyethyl];

[0370] Examples include unsaturated acrylates containing hydroxyl and carboxyl groups in the same molecule, such as α-(hydroxymethyl)acrylic acid; etc.

[0371] Among these, acrylic acid, methacrylic acid, and maleic anhydride are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in an alkaline aqueous solution.

[0372] In addition, in this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0373] Monomer (b) refers to a polymerizable compound having an ethylenically unsaturated bond with a cyclic ether structure having 2 to 4 carbon atoms (e.g., at least one selected from the group consisting of an oxiran ring, an oxetane ring, and a tetrahydrofuran ring (oxolan ring)). Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0374] Examples of monomers (b) include a monomer having an ethylene unsaturated bond with an oxiranyl group (hereinafter referred to as “monomer (b1)”), a monomer having an ethylene unsaturated bond with an oxetanyl group (hereinafter referred to as “monomer (b2)”), a monomer having an ethylene unsaturated bond with a tetrahydrofuryl group (hereinafter referred to as “monomer (b3)”), etc.

[0375] Examples of monomers (b1) include a monomer having a structure formed by epoxidizing an unsaturated aliphatic hydrocarbon (hereinafter referred to as “monomer (b1-1)”) and a monomer having a structure formed by epoxidizing an unsaturated alicyclic hydrocarbon (hereinafter referred to as “monomer (b1-2)”).

[0376] As for the monomer (b1-1), a monomer having an ethylenically unsaturated bond with a glycidyl group is preferred. As monomer (b1-1), specifically, 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(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, Examples include 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, etc.

[0377] Examples of monomers (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., celoxide (registered trademark) 2000; manufactured by Daicel Inc.), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., cyclomer (registered trademark) A400; manufactured by Daicel Inc.), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., cyclomer (registered trademark) M100; manufactured by Daicel Inc.), compounds represented by formula (BI) and compounds represented by formula (BII), etc.

[0378] [Chemical Formula 38]

[0379]

[0380] [Among Equation (BI) and Equation (BII), R a and R b Each represents, independently, a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom included in the said alkyl group may be substituted by a hydroxyl group.

[0381] X a and X b is, independently of each other, single bond, *-R c -, *-R c -O-, *-R c -S- or *-R c -NH- represents.

[0382] R c It represents an alkandyl group having 1 to 6 carbon atoms.

[0383] * indicates a bond with O.]

[0384] Examples of alkyl groups having 1 to 4 carbon atoms include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, tert-butyl groups, etc.

[0385] Examples of alkyl groups in which a hydrogen atom is substituted by a hydroxyl group include, for instance, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, etc.

[0386] R a and R b Preferably, hydrogen atoms, methyl groups, hydroxymethyl groups, 1-hydroxyethyl groups, and 2-hydroxyethyl groups may be used, and more preferably, hydrogen atoms and methyl groups may be used.

[0387] Examples of alkanedyl groups include, for instance, methylene groups, ethylene groups, propane-1,2-diyl groups, propane-1,3-diyl groups, butane-1,4-diyl groups, pentane-1,5-diyl groups, hexane-1,6-diyl groups, etc.

[0388] X a and X b Preferably, examples include a single bond, a methylene group, an ethylene group, a *-CH2-O- (* indicates a bond loss with O), and a *-CH2CH2-O- group; more preferably, examples include a single bond and a *-CH2CH2-O- group (* indicates a bond loss with O).

[0389] Examples of compounds represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9), and (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9), and (BI-15) are more preferred.

[0390] [Chemical Formula 39]

[0391]

[0392] Compounds represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15), among which compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and formulas (BII-11) to (BII-15) are preferred, and compounds represented by formulas (BII-1), (BII-7), (BII-9), and (BII-15) are more preferred.

[0393] [Chemical Formula 40]

[0394]

[0395] The compound represented by formula (BI) and the compound represented by formula (BII) may each be used alone, or the compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When using them in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5 on a molar basis, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

[0396] As for the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. Examples of monomers (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, 3-ethyl-3-(meth)acryloyloxyethyloxetane, etc.

[0397] As for the monomer (b3) having an ethylenically unsaturated bond with a tetrahydrofuryl group, a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. Examples of monomers (b3) include tetrahydrofurfuryl acrylate (e.g., Viscot V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0398] As monomer (c), for example, methyl(meth)acrylate, ethyl(meth)acrylate, n-butyl(meth)acrylate, sec-butyl(meth)acrylate, tert-butyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, dodecyl(meth)acrylate, lauryl(meth)acrylate, stearyl(meth)acrylate, cyclopentyl(meth)acrylate, cyclohexyl(meth)acrylate, 2-methylcyclohexyl(meth)acrylate, tricyclo[5.2.1.0 2,6 ] Decane-8-yl (meth)acrylate (in the art, it is commonly referred to as "dicyclofentanyl (meth)acrylate." It is also sometimes referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 ]Decan-9-yl(meth)acrylate, tricyclo[5.2.1.0 2,6 ] Decene-8-yl (meth)acrylate (known by the common name “dicyclopentenyl (meth)acrylate” in the art), tricyclo[5.2.1.0 2,6 (Meta)acrylic acid esters such as decene-9-yl (meth)acrylate, dicyclofentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;

[0399] Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

[0400] Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate;

[0401] Bicyclo[2.2.1]hept-2-en, 5-methylbicyclo[2.2.1]hept-2-en, 5-ethylbicyclo[2.2.1]hept-2-en, 5-hydroxybicyclo[2.2.1]hept-2-en, 5-hydroxymethylbicyclo[2.2.1]hept-2-en, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-en, 5-methoxybicyclo[2.2.1]hept-2-en, 5-ethoxybicyclo[2.2.1]hept-2-en, 5,6-dihydroxybicyclo[2.2.1]hept-2-en, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-en, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-en, 5,6-dimethoxybicyclo[2.2.1]hept-2-en, 5,6-diethoxybicyclo[2.2.1]hept-2-en, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-en, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-en, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-en, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-en, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-en, Bicyclounsaturated compounds such as 5-phenoxycarbonylbicyclo[2.2.1]hept-2-en, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-en and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-en;

[0402] Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl-6-maleimidecaproate, N-succinimidyl-3-maleimidepropionate, and N-(9-acridinyl)maleimide;

[0403] Examples include vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene; etc.

[0404] Among these, styrene, vinyltoluene, and tricyclo[5.2.1.0 2,6 ]Decan-8-yl(meth)acrylate, tricyclo[5.2.1.0 2,6 ]Decan-9-yl(meth)acrylate, tricyclo[5.2.1.0 2,6 ]Decen-8-yl(meth)acrylate, tricyclo[5.2.1.0 2,6 It is preferable to use at least one selected from the group consisting of decene-9-yl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, 2-hydroxyethyl (meth)acrylate, and benzyl (meth)acrylate.

[0405] In resin [K1], the proportion of structural units derived from each is, among the total structural units constituting resin [K1],

[0406] Structural unit derived from (a); 2–60 mol%

[0407] Structural unit derived from (b); 40–98 mol%

[0408] It is desirable that,

[0409] Structural unit derived from (a); 10–50 mol%

[0410] Structural unit derived from (b); 50–90 mol%

[0411] It is more desirable to be.

[0412] If the ratio of the structural unit of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.

[0413] Resin [K1] can be manufactured by referring to the method described in the document “Experimental Methods for Polymer Synthesis” (authored by Takayuki Otsu, published by Chemical Doujin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited literature mentioned in the said document.

[0414] Specifically, a method may be used in which a predetermined amount of (a) and (b), a polymerization initiator, and a solvent are placed into a reaction vessel, and a deoxygenated atmosphere is created by, for example, replacing oxygen with nitrogen, and the mixture is heated and maintained while stirring. Furthermore, the polymerization initiator and solvent used herein are not particularly limited and may be those commonly used in the field. For example, as a polymerization initiator, an azo compound (2,2'-azobis(isobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) may be used, and as a solvent, it is sufficient to dissolve each monomer, and the solvent described below may be used as the solvent (E) of the colored resin composition of the present invention.

[0415] In addition, the obtained copolymer may be used as is after the reaction solution, as a concentrated or diluted solution, or as a solid (powder) extracted by methods such as reprecipitation. In particular, by using a solvent included in the colored resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as is for preparing the colored resin composition of the present invention, thereby simplifying the manufacturing process of the colored resin composition of the present invention.

[0416] In resin [K2], the proportion of structural units derived from each is, among the total structural units constituting resin [K2],

[0417] Structural unit derived from (a); 2–45 mol%

[0418] Structural unit derived from (b); 2–95 mol%

[0419] Structural unit derived from (c); 1–65 mol%

[0420] It is desirable that,

[0421] Structural unit derived from (a); 5–40 mol%

[0422] Structural unit derived from (b); 5–80 mol%

[0423] Structural unit derived from (c); 5–60 mol%

[0424] It is more desirable to be.

[0425] When the ratio of structural units of resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the resulting color filter tend to be excellent.

[0426] Resin [K2] can be manufactured in the same way as described, for example, as a method for manufacturing resin [K1].

[0427] In resin [K3], the proportion of structural units derived from each is, among the total structural units constituting resin [K3],

[0428] Structural unit derived from (a); 2–60 mol%

[0429] Structural unit derived from (c); 40–98 mol%

[0430] It is desirable that,

[0431] Structural unit derived from (a); 10–50 mol%

[0432] Structural unit derived from (c); 50–90 mol%

[0433] It is more desirable to be.

[0434] Resin [K3] can be manufactured in the same way as described in the method for manufacturing resin [K1], for example.

[0435] The resin [K4] can be prepared by obtaining a copolymer of (a) and (c) and adding a cyclic ether having 2 to 4 carbon atoms of (b) to a carboxylic acid and / or carboxylic anhydride of (a).

[0436] First, a copolymer of (a) and (c) is prepared in the same manner as described for the method of preparing resin [K1]. In this case, it is preferable that the ratio of structural units derived from each be the same as that given in resin [K3].

[0437] Next, a cyclic ether having 2 to 4 carbon atoms of (b) is reacted with a portion of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer.

[0438] After preparing the copolymer of (a) and (c), the atmosphere inside the flask is replaced from nitrogen to air, and (b) a reaction catalyst for a carboxylic acid or carboxylic anhydride and a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (e.g., hydroquinone, etc.) are added to the flask, and the resin [K4] can be prepared by reacting for 1 to 10 hours at, for example, 60 to 130°C.

[0439] The amount of (b) used is preferably 5 to 80 moles per 100 moles of (a), and more preferably 10 to 75 moles. By using this range, the balance of storage stability of the colored resin composition, developability when forming a pattern, and solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern tends to be good. Since the reactivity of the cyclic ether is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in the resin [K4], and (b1-1) is more preferred.

[0440] The amount of the above reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The amount of the above polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c).

[0441] Reaction conditions, such as the introduction method, reaction temperature, and time, can be appropriately adjusted by considering the manufacturing equipment or the heat generated by polymerization. In addition, similar to polymerization conditions, the introduction method or reaction temperature can be appropriately adjusted by considering the manufacturing equipment or the heat generated by polymerization.

[0442] As a first step, the resin [K5] is obtained by the same method as the resin [K1] described above to obtain a copolymer of (b) and (c). As above, the obtained copolymer may be used as is after the reaction solution, or a concentrated or diluted solution, or a solid (powder) extracted by means such as reprecipitation.

[0443] The proportion of structural units derived from (b) and (c) is, respectively, with respect to the total moles of all structural units constituting the copolymer,

[0444] Structural unit derived from (b); 5–95 mol%

[0445] Structural unit derived from (c); 5–95 mol%

[0446] It is desirable that,

[0447] Structural unit derived from (b); 10–90 mol%

[0448] Structural unit derived from (c); 10–90 mol%

[0449] It is more desirable to be.

[0450] In addition, resin [K5] can be obtained by reacting the cyclic ether derived from (b) of the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride of (a) under conditions similar to the method of manufacturing resin [K4].

[0451] The amount of (a) used to react with the above copolymer is preferably 5 to 80 moles per 100 moles of (b). Since the reactivity of the cyclic ether is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) for use in the resin [K5], and (b1-1) is more preferred.

[0452] Resin [K6] is a resin in which a carboxylic anhydride is additionally reacted with resin [K5]. A carboxylic anhydride is reacted with the hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic anhydride.

[0453] Examples of carboxylic acid anhydrides include maleic anhydride, citraconic acid anhydride, itaconic acid anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of carboxylic acid anhydride used is preferably 0.5 to 1 mole per 1 mole of the amount used in (a).

[0454] Specific resin (B) is 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6]Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; Resins such as resins in which glycidyl (meth)acrylate is added to a benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins in which glycidyl (meth)acrylate is added to a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins in which glycidyl (meth)acrylate is added to a tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, etc. [K4]; resins in which (meth)acrylic acid is reacted with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate, resins in which (meth)acrylic acid is reacted with a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate, etc. [K5]; Examples include resins such as [K6], which are formed by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate, and additionally reacting tetrahydrophthalic anhydride with the resulting resin.

[0455] It is more preferable that the resin (B) be at least one selected from the group consisting of resin [K1] and resin [K2], and particularly preferable that it be resin [K2].

[0456] The weight-average molecular weight (Mw) of the resin (B) in terms of polystyrene is preferably 1,000 or more and 100,000 or less, more preferably 2,000 or more and 50,000 or less, and even more preferably 3,000 or more and 30,000 or less. When the weight-average molecular weight is in the above range, the solubility of the unexposed portion in the developer is high, and the residual film rate and hardness of the resulting pattern also tend to be high.

[0457] The dispersion [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] of the resin (B) is preferably 1 or more and 6 or less, more preferably 1.001 or more and 4 or less, and even more preferably 1.01 or more and 4 or less.

[0458] The acid value (converted to solid content) of resin (B) is preferably 10 mg-KOH / g or more and 300 mg-KOH / g or less, more preferably 20 mg-KOH / g or more and 250 mg-KOH / g or less, even more preferably 25 mg-KOH / g or more and 200 mg-KOH / g or less, even more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, and particularly preferably 60 mg-KOH / g or more and 135 mg-KOH / g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin, and can be obtained, for example, by titrating using an aqueous potassium hydroxide solution.

[0459] The content of resin (B) is preferably 5 to 50 mass% of the solid content of the colored resin composition, more preferably 10 to 40 mass%, and even more preferably 15 to 30 mass%. When the content of resin (B) is within the above range, the solubility of the unexposed portion in the developer tends to be high.

[0460] < Polymerizable compound (C) >

[0461] The polymerizable compound (C) is a compound that can be polymerized by an active radical and / or acid generated from a polymerization initiator (D), and examples include compounds having polymerizable ethylenically unsaturated bonds, and preferably (meth)acrylic acid ester compounds.

[0462] Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropylacrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc., and the monomers (a), (b), and (c) described above.

[0463] Examples of polymerizable compounds having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A and 3-methylpentanediol di(meth)acrylate.

[0464] The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include, for instance, 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, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, and propylene glycol-modified Examples include pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate, and preferably at least one selected from the group consisting of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0465] The weight-average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 70 or more and 3,500 or less, even more preferably 100 or more and 3,000 or less, even more preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

[0466] The content of the polymerizable compound (C) may be, for example, 1 mass% or more and 99 mass% or less with respect to the total amount of solids of the colored resin composition, preferably 5 mass% or more and 90 mass% or less, more preferably 10 mass% or more and 80 mass% or less, and even more preferably 12 mass% or more and 70 mass% or less.

[0467] < Polymerization Initiator (D) >

[0468] The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating active radicals, acids, etc., by the action of light or heat and initiating polymerization, and known polymerization initiators may be used.

[0469] Examples of polymerization initiators (D) include O-acyloxime compounds, alkylphenone compounds, nonimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0470] As O-acyloxime compounds, for example, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, Examples include N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclofentanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine. In addition, commercially available products such as Irgacure (registered trademark) OXE01 and OXE02 (both manufactured by BASF), N-1919 (manufactured by ADEKA Inc.), and TR-PBG327 (manufactured by Sangju Kyouryoku Electronic New Materials Co., Ltd.) may be used as O-acyloxime compounds. Among these, as the O-acyloxime compound, at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, and TR-PBG327 (N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine) is preferred, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and TR-PBG327 (N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine) At least one type selected from the group is more preferable.

[0471] Examples of alkylphenone compounds include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinoyl)phenyl]butan-1-one. As alkylphenone compounds, commercially available products such as Yirgacure (registered trademark) 369, 907, and 379 (all manufactured by BASF) may be used.

[0472] Examples of alkylphenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenylketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyldimethylketal.

[0473] As nonimidazole compounds, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Publication No. JP 6-75372, Japanese Patent Publication No. JP 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (for example, Japanese Patent Publication No. Examples include Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. 62-174204, etc.) and non-imidazole compounds in which a phenyl group at the 4,4',5,5'-position is substituted by a carboalkoxy group (e.g., Japanese Patent Publication No. 7-10913, etc.).

[0474] As triazine compounds, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(5-methylfuran-2-yl)ethenyl〕-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(furan-2-yl)ethenyl〕-1,3,5-triazine, Examples include 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0475] Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercial products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

[0476] In addition, polymerization initiator (D) may include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, o-benzoylbenzoate methyl, 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-phenanthrenquinone, 2-ethylanthraquinone and camphorquinone; and 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate and titanocene compounds.

[0477] It is preferable to use these in combination with the polymerization initiation agent (D1) (especially an amine compound) described below.

[0478] The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and non-imidazole compounds, and more preferably a polymerization initiator comprising an O-acyloxime compound.

[0479] The content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass or less, and more preferably 1 part by mass or more and 20 parts by mass or less, with respect to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C) included in the colored resin composition. When the content of the polymerization initiator (D) is within the above range, the productivity of the color filter is improved because the sensitivity is increased and the exposure time tends to be shortened.

[0480] < Polymerization Initiation Agent (D1) >

[0481] The colored resin composition of the present invention may include a polymerization initiation agent (D1). The polymerization initiation agent (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound (C) whose polymerization has been initiated by a polymerization initiator (D). When the polymerization initiation agent (D1) is included, it is typically used in combination with the polymerization initiator (D).

[0482] Examples of polymerization initiation agents (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0483] Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Mihiler ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, and preferably 4,4'-bis(diethylamino)benzophenone. In addition, commercial products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) may be used as amine compounds.

[0484] Examples of alkoxianthracene compounds include 9,10-dimethoxycyanthracene, 2-ethyl-9,10-dimethoxycyanthracene, 9,10-diethoxycyanthracene, 2-ethyl-9,10-diethoxycyanthracene, 9,10-dibutoxycyanthracene, and 2-ethyl-9,10-dibutoxycyanthracene.

[0485] Examples of thioxantone compounds include 2-isopropylthioxantone, 4-isopropylthioxantone, 2,4-diethylthioxantone, 2,4-dichlorothioxantone, and 1-chloro-4-propoxythioxantone.

[0486] Examples of carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0487] When using these polymerization initiation agents (D1), the content thereof 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, with respect to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C) included in the colored resin composition.

[0488] < Solvent (E) >

[0489] The solvent (E) is not particularly limited and may use any solvent commonly used in the field.

[0490] The solvent (E) may be, for example, an ester solvent (a solvent containing -COO- in the molecule and not -O-), an ether solvent (a solvent containing -O- in the molecule and not -COO-), an ether ester solvent (a solvent containing -COO- and -O- in the molecule), a ketone solvent (a solvent containing -CO- in the molecule and not -COO-), an alcohol solvent (a solvent containing OH in the molecule and not -O-, -CO- and -COO-), an aromatic hydrocarbon solvent, an amide solvent, a dimethyl sulfoxide, etc. Two or more of these solvents may be used in combination.

[0491] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, 2-methyl hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0492] 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, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, and methylanisole.

[0493] As ether ester solvents, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, 3-methyl methoxypropionate, 3-ethyl methoxypropionate, 3-methyl methoxypropionate, 3-ethyl ethoxypropionate, 2-methyl methoxypropionate, 2-ethyl methoxypropionate, 2-propyl methoxypropionate, 2-methyl ethoxypropionate, 2-ethyl ethoxypropionate, 2-methyl-2-methylpropionate, 2-ethoxy-2-ethylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, Examples include propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

[0494] 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.

[0495] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0496] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0497] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0498] As for the solvent (E), it is preferable that the solvent comprises at least one selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol, and cyclohexanone.

[0499] The content of solvent (E) is typically 99.99 mass% or less with respect to the total amount of the colored resin composition, preferably 40 mass% or more and 99 mass% or less, more preferably 50 mass% or more and 95 mass% or less, more preferably 70 mass% or more and 95 mass% or less, and even more preferably 75 mass% or more and 90 mass% or less. In other words, the total amount of solids in the colored resin composition is typically 0.01 mass% or more, preferably 1 mass% or more and 60 mass% or less, more preferably 5 mass% or more and 50 mass% or less, more preferably 5 mass% or more and 30 mass% or less, and even more preferably 10 mass% or more and 25 mass% or less. When the content of solvent (E) is within the above range, the flatness during coating is improved, and since the color concentration is not insufficient when a color filter is formed, the display characteristics tend to be good.

[0500] < Leveling Agent (F) >

[0501] Examples of leveling agents (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may have polymerizable groups in their side chains.

[0502] Examples of silicone-based surfactants include surfactants having siloxane bonds within the molecule. Specifically, examples include Toray Silicon DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan).

[0503] Examples of fluorine-based surfactants include surfactants having a fluorocarbon chain within the molecule. Specifically, examples include Florad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Inc.), Megapac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Inc.), F-Top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Inc.), Surfron (registered trademark) S381, S382, SC101, SC105 (manufactured by AGC Inc.), and E5844 (manufactured by Daikin Fine Chemical Research Institute Inc.).

[0504] Examples of silicone-based surfactants having fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains within the molecule. Specifically, examples include MegaPac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Co., Ltd.).

[0505] When a leveling agent (F) is included, the content of the leveling agent (F) is preferably 0.0005 mass% or more and 1 mass% or less with respect to the total amount of the colored resin composition, more preferably 0.001 mass% or more and 0.5 mass% or less, and even more preferably 0.005 mass% or more and 0.1 mass% or less. In addition, the content of the dispersant mentioned above is not included in this content. If the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0506] Other ingredients

[0507] The colored resin composition may, if necessary, include additives known in the art, such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, etc.

[0508] < Method for manufacturing a colored resin composition >

[0509] A colored resin composition can be prepared by mixing a coloring agent (A), a resin (B), and, if necessary, a polymerizable compound (C), a polymerization initiator (D), a polymerization initiation aid (D1), a solvent (E), a leveling agent (F), and other components. Mixing can be performed using known or conventional equipment or under common conditions.

[0510] The coloring agent (A) may be used as a coloring agent-containing liquid obtained by mixing it with part or all of the solvent (E) in advance and dispersing it using a bead mill or the like until the average particle size is about 0.2 μm or less, and it is preferable to use it as a coloring agent-containing liquid. At this time, part or all of the above-mentioned dispersant and resin (B) may be mixed as needed. In addition, the coloring agent (A) may be used as a coloring agent-containing liquid obtained by dissolving it in part or all of the solvent (E) in advance. By mixing the remaining components to the coloring agent-containing liquid obtained in this way to a predetermined concentration, a coloring resin composition of the desired color can be prepared.

[0511] Method for manufacturing color filters

[0512] A color filter, which may also be a color conversion layer, can be formed from the colored resin composition of the present invention. Methods for forming a colored pattern include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. Photolithography is a method of applying the colored resin composition to a substrate, drying it to form a colored resin composition layer, and exposing the colored resin composition layer to light through a photomask and developing it. In photolithography, a colored film, which is a cured product of the colored resin composition layer, can be formed by not using a photomask during exposure and / or by not developing. The colored pattern or colored film formed in this way is the color filter of the present invention.

[0513] The film thickness of the color filter being produced is not particularly limited and can be appropriately adjusted according to the purpose or use, for example, 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, more preferably 0.5 μm or more and 6 μm or less, and even more preferably 0.8 μm or more and 4.5 μm or less.

[0514] As a substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, or soda-lime glass with a silica-coated surface, resin plates such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or thin films of aluminum, silver, or silver / copper / palladium alloy formed on the substrate are used. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates.

[0515] The formation of each color pixel by the photolithography method can be performed using known or conventional devices or conditions. For example, it can be produced as follows.

[0516] First, a colored resin composition is applied onto a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying, thereby obtaining a smooth colored resin composition layer.

[0517] Examples of coating methods include spin coating, slit coating, and slit-and-spin coating.

[0518] When performing heat drying, the temperature is preferably 30°C or higher and 120°C or lower, and more preferably 50°C or higher and 110°C or lower. In addition, the heating time is preferably 10 seconds or longer and 60 minutes or shorter, and more preferably 30 seconds or longer and 30 minutes or shorter.

[0519] When performing vacuum drying, it is preferable to do so under a pressure of 50 Pa or more and 150 Pa or less, and in a temperature range of 20°C or more and 25°C or less.

[0520] The film thickness of the colored resin composition layer is not particularly limited and can be appropriately selected according to the film thickness of the desired color filter.

[0521] Next, the colored resin composition layer is exposed through a photomask to form a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended application is used. In addition, it is preferable to use an exposure device such as a mask aligner and a stepper, as this allows for uniformly irradiating parallel light rays across the entire exposure surface and enables accurate positional alignment between the photomask and the substrate on which the colored resin composition layer is formed. When forming a colored film, exposure can be performed without using a photomask.

[0522] As a light source used for exposure, a light source that generates light with a wavelength of 250 nm or more and 450 nm or less is preferred. For example, light with a wavelength of less than 350 nm may be cut using a filter that cuts this wavelength range, or light with wavelengths around 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specifically, examples include mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, etc.

[0523] A colored pattern is formed on a substrate by contacting the colored resin composition layer after exposure with a developer solution and developing it. Through development, the unexposed portion of the colored resin composition layer is dissolved in the developer solution and removed. As for the developer solution, an aqueous solution of an alkaline compound, such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide, is preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 mass% or more and 10 mass% or less, and more preferably 0.03 mass% or more and 5 mass% or less. In addition, the developer solution may contain a surfactant.

[0524] The development method may be any of the following: paddle method, dipping method, or spray method. Additionally, the substrate may be tilted at any angle during development.

[0525] It is desirable to wash the substrate after development.

[0526] In addition, it is preferable to perform a post-bake on the obtained coloring pattern or coloring film. The post-bake temperature is preferably 150°C or higher and 250°C or lower, and more preferably 160°C or higher and 240°C or lower. The post-bake time is preferably 1 minute or higher and 120 minutes or lower, and more preferably 10 minutes or higher and 60 minutes or lower.

[0527] < Display Device >

[0528] The above color filter is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices.

[0529] This application claims the benefit of priority based on Japanese Patent Application No. 2021-078790 filed on May 6, 2021. The full contents of the specification of Japanese Patent Application No. 2021-078790 filed on May 6, 2021 are incorporated herein by reference.

[0530] Examples

[0531] Next, the present invention will be explained in more detail by citing synthetic examples. In the examples, % and parts indicating content or usage amount are based on mass unless otherwise specified.

[0532] In the following synthesis examples, the structure of the compound was confirmed by mass spectrometry (LC; Agilent Type 1200, MASS; Agilent LC / MSD6130).

[0533] Synthesis of Pigments

[0534] [Dye Synthesis Example 1: Synthesis of Compound (BI-1)]

[0535] The following reaction was carried out under a nitrogen atmosphere. 0.48 parts of palladium acetate (manufactured by Tokyo Kasei Industry, Inc.), 1.74 parts of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (manufactured by Tokyo Kasei Industry, Inc.), 7.50 parts of sodium tert-butoxide (manufactured by Tokyo Kasei Industry, Inc.), and 14.58 parts of 1-bromonaphthalene (manufactured by Tokyo Kasei Industry, Inc.) were added to a flask equipped with a cooling tube and a stirring device, and then a mixed solution of 9 parts of 4,4'-methylenebis(2,6-dimethylaniline) (manufactured by Sigma-Aldrich) and 63 parts of toluene was added dropwise to the flask. This reaction mixture was stirred for 2 hours while heating it to 110°C in an oil bath. After cooling the reaction solution, Celite filtration was performed to obtain a filtrate. To this, 180 parts of ethyl acetate and 180 parts of deionized water were added and mixed vigorously, then separated to obtain an organic layer. The obtained organic layer was dried with 48 parts of sodium sulfate, and the solid was removed by filtration. The obtained organic layer was concentrated to obtain a crude body. The obtained crude body was purified by silica gel column chromatography (solvent: chloroform / methanol 100 / 1 to 20 / 1), the resulting fraction was concentrated under reduced pressure, and dried under reduced pressure at 60°C to obtain 11.6 parts of the compound represented by formula (BI-1).

[0536] [Chemical Formula 41]

[0537]

[0538] Identification of the compound represented by formula (BI-1)

[0539] (Mass Spectrometry) Ionization Mode = ESI+: m / z = 506.5

[0540] [Dye Synthesis Example 2: Synthesis of Compound (BI-2)]

[0541] 5.11 parts of 4,4'-methylenebis-o-toluidine, 9.38 parts of 1-bromonaphthalene (Tokyo Kasei Industry Co., Ltd.), 0.28 parts of palladium acetate (Tokyo Kasei Industry Co., Ltd.), 1.12 parts of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Tokyo Kasei Industry Co., Ltd.), 4.76 parts of tert-butoxysodium (Tokyo Kasei Industry Co., Ltd.), and 63 parts of toluene were mixed and stirred at 110°C for 1 hour. After cooling to 25°C, the obtained mixture was filtered through Celite, and the filtrate was concentrated. The obtained residue was purified by a silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C, and 9.10 parts of the compound represented by formula (BI-2) were obtained (yield 84%).

[0542] [Chemical Formula 42]

[0543]

[0544] Identification of the compound represented by formula (BI-2)

[0545] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M + H] + 479.4

[0546] [Dye Synthesis Example 3: Synthesis of Compound (BI-3)]

[0547] Under cooling in an ice bath, 8.32 parts of tert-butoxysodium were added to 10.4 parts of the compound represented by formula (BI-2) and 4.8 parts of dimethyl sulfoxide, followed by the addition of 13.52 parts of ethyl iodide, and the mixture was stirred at 80°C for 7 hours. After cooling to 25°C, 312 parts of methanol were added to the resulting mixture to form a suspension, and the mixture was filtered. The obtained crude was purified by silica gel column chromatography (developed phase: chloroform). After drying under reduced pressure at 60°C, 10.14 parts of the compound represented by formula (BI-3) were obtained (yield 87%).

[0548] [Chemical Formula 43]

[0549]

[0550] Identification of compound (BI-3)

[0551] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M + H] + 535.5

[0552] [Dye Synthesis Example 4: Synthesis of Compound (BI-4)]

[0553] 20 parts of 3-chloro-2,6-dimethylaniline, 300 parts of deion-exchanged water, and 1.9 parts of paraformaldehyde were mixed and stirred at 100°C for 3 hours. After cooling to 0°C, 500 parts of a cold 4% aqueous sodium hydroxide solution were added to the resulting reaction solution to form a suspension, and the mixture was filtered. The obtained solid was dried under reduced pressure at 60°C to obtain 22 parts of the compound represented by formula (BI-4a).

[0554] [Chemical Formula 44]

[0555]

[0556] The following reaction was carried out under a nitrogen atmosphere. 1.1 parts of bis(dibenzylideneacetone)palladium (0), 1.2 parts of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 17.8 parts of sodium tert-butoxide, and 20 parts of a compound represented by formula (BI-4a) were added to a flask equipped with a cooling tube and a stirring device, and then 32 parts of 1-bromonaphthalene and 600 parts of toluene were added dropwise to the flask. The reaction mixture was heated to 70°C in an oil bath and stirred for 2 hours. After cooling the reaction mixture in an ice bath, it was diluted with 500 parts of ethyl acetate, poured into 500 parts of 1.5N hydrochloric acid, stirred, and separated to obtain an organic layer. The obtained organic layer was concentrated to obtain 51 parts of a crude body. This was purified by silica gel column chromatography (solvent: petroleum ether / ethyl acetate 100 / 3), the obtained fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 12.8 parts of the compound represented by formula (BI-4).

[0557] [Chemical Formula 45]

[0558]

[0559] [Dye Synthesis Example 5: Synthesis of Compound (BI-5)]

[0560] 75 parts of 2-nitro-m-xylene, 176.6 parts of N-bromosuccinimide, 0.8 parts of iron powder, and 500 parts of trifluoroacetic acid were mixed and stirred at 75°C for 72 hours. After cooling to 25°C, the mixture was diluted with 1,500 parts of ethyl acetate, poured into 500 parts of a 10% aqueous sodium bicarbonate solution, stirred, and separated to obtain an organic layer. The obtained organic layer was concentrated to obtain 89 parts of a crude body. This was purified by silica gel column chromatography (solvent: petroleum ether / ethyl acetate 100 / 0→70 / 30), the obtained fraction was concentrated under reduced pressure, and dried under reduced pressure at 60°C to obtain 76 parts of the compound represented by formula (BI-5a).

[0561] [Chemical Formula 46]

[0562]

[0563] 72 parts of the compound represented by formula (BI-5a), 4.5 parts of copper(I) bromide, 202.9 parts of a methanol solution of 25% sodium methoxide, 360 parts of methanol, and 720 parts of N,N-dimethylformamide were mixed and stirred at 100°C for 12 hours. After cooling to 25°C, the mixture was diluted with 500 parts of ethyl acetate and filtered. 78 parts of the obtained crude mixture were purified by silica gel column chromatography (solvent: petroleum ether / ethyl acetate 100 / 0→80 / 20), the resulting fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 45 parts of the compound represented by formula (BI-5b).

[0564] [Chemical Formula 47]

[0565]

[0566] 45 parts of the compound represented by formula (BI-5b), 39.9 parts of ammonium chloride, 450 parts of methanol, 50 parts of deionized water, and 162.4 parts of zinc powder (total of 10 divided additions) were mixed and stirred at 25°C for 16 hours. The mixture was diluted with 500 parts of ethyl acetate and filtered using Celite, and the filtrate was concentrated to obtain a crude body. 500 parts of ethyl acetate and 500 parts of deionized water were added to the obtained crude body to separate the liquids, and the resulting organic layer was concentrated. 42 parts of the obtained crude body were purified by silica gel column chromatography (solvent: petroleum ether / ethyl acetate 100 / 0→90 / 10), the resulting fraction was concentrated under reduced pressure, and dried under reduced pressure at 60°C to obtain 36 parts of the compound represented by formula (BI-5c).

[0567] [Chemical Formula 48]

[0568]

[0569] Except for using the compound represented by formula (BI-5c) instead of 3-chloro-2,6-dimethylaniline, the same operation as in dye synthesis example 4 was performed to obtain the compound represented by formula (BI-5).

[0570] [Chemical Formula 49]

[0571]

[0572] [Dye Synthesis Example 6: Synthesis of Compound (CI-1)]

[0573] The following reaction was carried out under a nitrogen atmosphere. 0.27 parts of bis(dibenzylideneacetone)palladium (0) (manufactured by Tokyo Kasei Industry Co., Ltd.), 0.57 parts of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (manufactured by Sigma-Aldrich), 42.1 parts of sodium tert-butoxide (manufactured by Tokyo Kasei Industry Co., Ltd.), and 50 parts of 4,4'-dichlorobenzophenone (manufactured by Tokyo Kasei Industry Co., Ltd.) were added to a flask equipped with a cooling tube and a stirring device, and then a mixed solution of 48.3 parts of 2,6-dimethylaniline (manufactured by Tokyo Kasei Industry Co., Ltd.) and 432 parts of toluene was added dropwise to the flask. The reaction mixture was heated to 80°C in an oil bath and stirred for 2 hours. After cooling the reaction mixture in an ice bath, filtration was performed to obtain a solid and a filtrate. The solid was designated as body A1, and the filtrate as filtrate A1. The obtained body A1 was washed with 50 parts toluene and then washed twice with 250 parts deionized water to obtain a solid. This solid was designated as body B1. Filtrate A1, 50 parts toluene, 229 parts deionized water, and 20.8 parts 35% hydrochloric acid were added to a bottom-discharge flask and stirred for 1 hour, after which the mixture was separated to obtain an organic layer. The obtained organic layer was washed with a mixture of 238 parts deionized water and 12.5 parts sodium carbonate, dried with 150 parts magnesium sulfate, and the solid was removed by filtration. The obtained organic layer was concentrated to obtain a solid. This solid was designated as body C1. Alternative B1 and Alternative C1 were placed in a flask equipped with a stirring device, and acetonitrile at a mass 4 times the total mass of Alternative B1 and Alternative C1 was added and stirred for 1 hour. The solid obtained by filtering the mixture was washed with acetonitrile at a mass 1 times the total mass of Alternative B1 and Alternative C1. The washed solid was dried at 60°C under reduced pressure to obtain 75.9 parts of the compound represented by formula (Cl-1). Yield 90.6%.

[0574] [Chemical Formula 50]

[0575]

[0576] [Dye Synthesis Example 7: Synthesis of Compound (CI-2)]

[0577] The following reaction was carried out under a nitrogen atmosphere. Fifty parts of the compound represented by formula (Cl-1) and 188 parts of N,N-dimethylformamide were added to a flask equipped with a cooling tube and a stirring device, and the mixture was stirred for 30 minutes while cooling in an ice bath. Forty parts of potassium tert-butoxide (manufactured by Tokyo Kasei Industry Co., Ltd.) were added to the flask, and the mixture was stirred for an additional hour while cooling in an ice bath. While the reaction mixture was still in the ice bath, 55.6 parts of iodoethane (manufactured by Tokyo Kasei Industry Co., Ltd.) were added dropwise. The reaction mixture was heated to 35°C using an oil bath and stirred for 5 hours, after which it was cooled to room temperature. 1,000 parts of a 10% aqueous sodium chloride solution were added to another flask equipped with a stirring device, and the above reaction mixture was added dropwise while stirring. After stirring for 30 minutes, the mixture was filtered to obtain a solid. The obtained solid was washed three times with 500 parts of ion-exchanged water and dried at 60°C under reduced pressure to obtain 53.0 parts of the compound represented by the formula (Cl-2). Yield 93.5%.

[0578] [Chemical Formula 51]

[0579]

[0580] [Dye Synthesis Example 8: Synthesis of Compound (CI-3)]

[0581] A compound represented by the formula (CI-3) was obtained by performing the same procedure as in Example 6 of pigment synthesis, except that 2,4,6-trimethylaniline (manufactured by Tokyo Kasei Industry Co., Ltd.) was used instead of 2,6-dimethylaniline (manufactured by Tokyo Kasei Industry Co., Ltd.).

[0582] [Chemical Formula 52]

[0583]

[0584] [Dye Synthesis Example 9: Synthesis of Compound (CI-4)]

[0585] A compound represented by the formula (CI-4) was obtained in the same manner as in dye synthesis example 7, except that a compound represented by the formula (CI-3) was used instead of a compound represented by the formula (CI-1).

[0586] [Chemical Formula 53]

[0587]

[0588] [Dye Synthesis Example 10: Synthesis of Compound (CI-5)]

[0589] A compound represented by the formula (CI-5) was obtained by performing the same procedure as in dye synthesis example 6, except that 2,6-dimethyl-4-methoxycyaniline was used instead of 2,6-dimethylaniline (manufactured by Tokyo Kasei Industry Co., Ltd.).

[0590] [Chemical Formula 54]

[0591]

[0592] [Dye Synthesis Example 11: Synthesis of Compound (CI-6)]

[0593] A compound represented by the formula (CI-6) was obtained in the same manner as in dye synthesis example 7, except that a compound represented by the formula (CI-5) was used instead of a compound represented by the formula (CI-1).

[0594] [Chemical Formula 55]

[0595]

[0596] [Dye Synthesis Example 12: Synthesis of Compound (I-5a-1)]

[0597] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a cooling tube and a stirring device, 1 part of the compound represented by formula (BI-1), 11.28 parts of the compound represented by formula (CI-2), and 42 parts of toluene were added, followed by the addition of 5.4 parts of phosphorus oxychloride (manufactured by Fujifilm Wako Junyaku Inc.) and stirring at 110°C for 7.5 hours. Subsequently, the reaction mixture was cooled to room temperature, 450 parts of ethyl acetate and saturated saline solution were added, and the mixture was filtered to obtain a crude body. This was purified by silica gel column chromatography (solvent: chloroform / methanol 100 / 1 to 10 / 1), the obtained fraction was concentrated under reduced pressure, and dried under reduced pressure at 60°C to obtain 9.90 parts of the compound represented by formula (I-5a-1).

[0598] [Chemical Formula 56]

[0599]

[0600] Identification of the compound represented by formula (I-5a-1)

[0601] (Mass Spectrometry) Ionization mode = ESI+: m / z = 712.6, 2 valence

[0602] [Dye Synthesis Example 13: Synthesis of Compound (I-5a-2)]

[0603] The following reaction was carried out under a nitrogen atmosphere. Four parts of the compound represented by formula (I-5a-1) and 26.7 parts of methanol were added to a flask equipped with a cooling tube and a stirring device, and a blue solution was prepared by stirring at room temperature for 30 minutes.

[0604] 17.8 parts of water were added to a flask equipped with a cooling tube and a stirring device, and additionally, 6.2 parts of phosphotungstic acid hydrate (Kegine-type phosphotungstic acid; manufactured by Sigma-Aldrich Corp.) were added to the water and mixed at room temperature under an air atmosphere to prepare a phosphotungstic acid solution.

[0605] To the obtained phosphotungstic acid solution, the previously prepared blue solution and 53.4 parts of washing methanol were added dropwise. The mixture was heated to 55°C in an oil bath and stirred for 4 hours, after which it was cooled to room temperature. The reaction mixture was concentrated to obtain a crude body. 40 parts of deion-exchanged water were added to the obtained crude body to form a suspension, filtered, and then washed sequentially with 50 parts of deion-exchanged water and 10 parts of methanol. The obtained crude body was added to 80 parts of methanol and dispersed for 1 hour, after which it was filtered and washed with 50 parts of methanol. The blue solid obtained by this operation was dried under reduced pressure at 60°C, and 7.51 parts of the compound represented by formula (I-5a-2) were obtained.

[0606] [Chemical Formula 57]

[0607]

[0608] Identification of the compound represented by formula (I-5a-2)

[0609] (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1423.7

[0610] Ionization mode = MALDI -: m / z = 2902.5

[0611] [Dye Synthesis Example 14: Synthesis of Compound (I-5b)]

[0612] Ten parts of the compound represented by formula (I-5a-1) and 253 parts of sulfuric acid were mixed and stirred at 60°C for 6 hours. After cooling, the resulting mixture was added to 1,300 parts of ice water to form a suspension, and filtered to obtain a crude body. This was purified by silica gel column chromatography (developing phase chloroform / methanol 20 / 1→4 / 1). After drying under reduced pressure at 60°C, 8.1 parts of the compound represented by formula (I-5b) were obtained (yield 75%).

[0613] [Chemical Formula 58]

[0614]

[0615] Identification of the compound represented by formula (I-5b)

[0616] (Mass Spectrometry) Ionization mode = ESI+: m / z = 793.4, 2 valence

[0617] [Dye Synthesis Example 15: Synthesis of Compound (I-4a-1)]

[0618] A compound represented by formula (I-4a-1) was obtained by doing the same as in example 12 of pigment synthesis, except that a compound represented by formula (CI-4) was used instead of a compound represented by formula (CI-2).

[0619] [Chemical Formula 59]

[0620]

[0621] Identification of the compound represented by formula (I-4a-1)

[0622] (Mass Spectrometry) Ionization mode = ESI+: m / z = 740.6, 2 valence

[0623] [Dye Synthesis Example 16: Synthesis of Compound (I-4a-2)]

[0624] A compound represented by formula (I-4a-2) was obtained by doing the same as in pigment synthesis example 13, except that a compound represented by formula (I-4a-1) was used instead of a compound represented by formula (I-5a-1).

[0625] [Chemical Formula 60]

[0626]

[0627] Identification of the compound represented by formula (I-4a-2)

[0628] (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1479.8

[0629] Ionization mode = MALDI -: m / z = 2902.5

[0630] [Dye Synthesis Example 17: Synthesis of Compound (I-4b)]

[0631] Ten parts of the compound represented by formula (I-4a-1) and 253 parts of sulfuric acid were mixed and stirred at 60°C for 6 hours. After cooling, the resulting mixture was added to 1,300 parts of ice water to form a suspension, and filtered to obtain a crude body. This was purified by silica gel column chromatography (developing phase chloroform / methanol 20 / 1→4 / 1). After drying under reduced pressure at 60°C, 5.3 parts of the compound represented by formula (I-4b) were obtained (yield 49%).

[0632] [Chemical Formula 61]

[0633]

[0634] Identification of the compound represented by formula (I-4b)

[0635] (Mass Spectrometry) Ionization Mode = ESI+: m / z = 820.4

[0636] [Dye Synthesis Example 18: Synthesis of Compound (I-9a-1)]

[0637] A compound represented by formula (I-9a-1) was obtained by using a compound represented by formula (CI-6) instead of a compound represented by formula (CI-2), and using a compound represented by formula (BI-3) instead of a compound represented by formula (BI-1), in the same manner as in pigment synthesis example 12.

[0638] [Chemical Formula 62]

[0639]

[0640] Identification of the compound represented by formula (I-9a-1)

[0641] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] + 786.7, 2ga

[0642] [Dye Synthesis Example 19: Synthesis of Compound (I-9a-2)]

[0643] A compound represented by formula (I-9a-2) was obtained in the same manner as in pigment synthesis example 13, except that a compound represented by formula (I-9a-1) was used instead of a compound represented by formula (I-5a-1).

[0644] [Chemical Formula 63]

[0645]

[0646] Identification of the compound represented by formula (I-9a-2)

[0647] (Mass Spectrometry) Ionization Mode = MALDI+:

[0648] m / z=[MH] + 1571.6

[0649] Ionization mode = MALDI -:

[0650] m / z=[M+H+Na] - 2902.5

[0651] [Dye Synthesis Example 20: Synthesis of Compound (I-56a-1)]

[0652] A compound represented by formula (I-56a-1) was obtained by doing the same as in pigment synthesis example 12, except that a compound represented by formula (BI-4) was used instead of a compound represented by formula (BI-1).

[0653] [Chemical Formula 64]

[0654]

[0655] Identification of the compound represented by formula (I-56a-1)

[0656] (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1491.7

[0657] [Dye Synthesis Example 21: Synthesis of Compound (I-56a-2)]

[0658] A compound represented by formula (I-56a-2) was obtained in the same manner as in pigment synthesis example 13, except that a compound represented by formula (I-56a-1) was used instead of a compound represented by formula (I-5a-1).

[0659] [Chemical Formula 65]

[0660]

[0661] Identification of the compound represented by formula (I-56a-2)

[0662] (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1491.7

[0663] Ionization mode = MALDI -: m / z = 2902.5

[0664] [Dye Synthesis Example 22: Synthesis of Compound (I-59a-1)]

[0665] A compound represented by formula (I-59a-1) was obtained by doing the same as in pigment synthesis example 12, except that a compound represented by formula (BI-5) was used instead of a compound represented by formula (BI-1).

[0666] [Chemical Formula 66]

[0667]

[0668] Identification of the compound represented by formula (I-59a-1)

[0669] (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1483.8

[0670] [Dye Synthesis Example 23: Synthesis of Compound (I-59a-2)]

[0671] A compound represented by formula (I-59a-2) was obtained in the same manner as in pigment synthesis example 13, except that a compound represented by formula (I-59a-1) was used instead of a compound represented by formula (I-5a-1).

[0672] [Chemical Formula 67]

[0673]

[0674] Identification of the compound represented by formula (I-59a-2)

[0675] (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1483.8

[0676] Ionization mode = MALDI -: m / z = 2902.5

[0677] [Dye Synthesis Example 24: Synthesis of Compound (x1)]

[0678] In accordance with the contents of Japanese Patent Publication No. 2014-108975, a compound represented by the following formula (x1) was synthesized.

[0679] [Chemical Formula 68]

[0680]

[0681] [Dye Synthesis Example 25: Synthesis of Compound (x2)]

[0682] In accordance with the contents of Japanese Patent Publication No. 2014-108975, a compound represented by the following formula (x2) was synthesized.

[0683] [Chemical Formula 69]

[0684]

[0685] Suzy's composite image

[0686] [Resin Composite Example 1]

[0687] A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, 141 parts ethyl lactate and 178 parts propylene glycol monomethyl ether acetate were added, and the mixture was heated to 85°C while stirring. Subsequently, 38 parts acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]Decan-8-ylacrylate and 3,4-epoxytricyclo[5.2.1.0 2,6A mixed solution of 25 parts of a mixture of decane-9-ylacrylate (molar ratio 1:1), 137 parts of N-cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was held 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 and a solid content of 25.6%, as measured by a Type B viscometer (23°C). The weight-average molecular weight (Mw) of the resulting copolymer was 8.0 × 10⁻⁶. 3 The dispersion was 2.1, and the acid value converted to solid content was 109 mg-KOH / g. Resin B-1 has the following structural units.

[0688] [Chemical Formula 70]

[0689]

[0690] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the above resin were measured using the GPC method under the following conditions.

[0691] Device; K2479 (Manufactured by Shimadzu Corporation)

[0692] Column; SHIMADZU Shim-pack GPC-80M

[0693] Column temperature; 40℃

[0694] Solvent; Tetrahydrofuran (THF)

[0695] Test solution concentration; 25 mg / mL (solvent; THF)

[0696] Flow rate; 1.0 mL / min

[0697] Detector; RI

[0698] Calibration standard materials; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Toso Co., Ltd.)

[0699] The ratio of the weight-average molecular weight and the number-average molecular weight of the polystyrene equivalent obtained above was called the degree of dispersion (Mw / Mn).

[0700] [Example 1]

[0701] < Preparation of a coloring agent dispersion (A-1) containing compound (I-5a-2) >

[0702] 5 parts of compound (I-5a-2), 3 parts of acrylic dispersant, 2 parts of resin B-1 (solid content equivalent), 79 parts of propylene glycol monomethyl ether acetate, 10 parts of diacetone alcohol, 1 part of ethyl lactate, and 300 parts of 0.2 mm zirconia beads were mixed, and the resulting mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). Afterward, the zirconia beads were removed by filtration to obtain a coloring agent dispersion (A-1).

[0703] < Preparation of Colored Resin Composition >

[0704] (A) Colorant: Colorant dispersion (A-1) 245 parts

[0705] (B) Resin: Resin (B-1) (Solid content converted) 45 copies

[0706] (C) Polymerizable compound: dipentaerythritol hexaacrylate

[0707] (Kayarad (Registered Trademark) DPHA; No. of Nihon Kayaku Co., Ltd.) 50 copies

[0708] (D) Polymerization Initiator: TR-PBG327 (Manufactured by Shangzhou Jiangli Electronic New Materials Co., Ltd.) 3 parts

[0709] (F) Surfactant: Fluorinated surfactant

[0710] (Megapark (Registered Trademark) F554; Manufactured by DIC) Part 0.09

[0711] (E) Solvent: Propylene glycol monomethyl ether acetate (E-1)

[0712] 506

[0713] (E) Solvent: 27 parts ethyl lactate (E-2)

[0714] A colored resin composition was obtained by mixing.

[0715] [Examples 2–7, Comparative Examples 1–2]

[0716] Colored resin compositions were obtained in the same manner as in Example 1, except that compound (I-5a-2) was changed to the following compound.

[0717] Example 2: Compound (I-5b)

[0718] Example 3: Compound (I-4a-2)

[0719] Example 4: Compound (I-4b)

[0720] Example 5: Compound (I-9a-2)

[0721] Example 6: Compound (I-56a-2)

[0722] Example 7: Compound (I-59a-2)

[0723] Comparative Example 1: Compound (x1)

[0724] Comparative Example 2: Compound (x2)

[0725] < Production Example 1 >

[0726] (Production of red resin composition)

[0727] (A) Coloring agent: Acid Red 52 (Manufactured by Tokyo Kasei Industry Co., Ltd.) 8 parts

[0728] (B) Resin: Resin (B-1) (Solid content converted) 50 copies

[0729] (C) Polymerizable compound: dipentaerythritol hexaacrylate

[0730] (Kayarad (Registered Trademark) DPHA; No. of Nihon Kayaku Co., Ltd.) 50 copies

[0731] (D) Polymerization Initiator: TR-PBG327 (Manufactured by Shangzhou Jiangli Electronic New Materials Co., Ltd.) 3 parts

[0732] (F) Surfactant: Fluorinated surfactant

[0733] (Megapark (Registered Trademark) F554; Manufactured by DIC) Part 0.09

[0734] (E) Solvent: Propylene glycol monomethyl ether acetate (E-1)

[0735] Part 127

[0736] (E) Solvent: 30 parts ethyl lactate (E-2)

[0737] (E) Solvent: 4-hydroxy-4-methyl-2-pentanone (E-3)

[0738] Part 472

[0739] A red resin composition was obtained by mixing.

[0740] < Formation of a Colored Film (Color Filter) >

[0741] On a glass substrate (Eagle 2000; manufactured by Corning) measuring 2 inches by 2 inches, the colored resin compositions obtained in Examples 1 to 7 and Comparative Examples 1 to 2, and the red resin composition obtained in Example 1 were each applied by spin coating, and then pre-baked at 100°C for 3 minutes to form a composition layer. After cooling, the composition layer was irradiated with light using an exposure device (TME-150RSK; manufactured by Topcon) under an atmospheric atmosphere at an exposure amount of 60 mJ / ㎠ (based on 365 nm), and then post-baked in an oven at 230°C for 20 minutes to obtain a colored coating film.

[0742] < Measurement of Transmission Spectrum >

[0743] Using a colorimeter (OSP-SP-200) device manufactured by Olympus, the transmission spectra of the colored coatings obtained from Examples 1 to 7, Comparative Examples 1 to 2, and Production Example 1 were each measured.

[0744] Calculation of Brightness >

[0745] The CIE chromaticity coordinates and stimulus value (Y) were determined when the colored resin compositions of Examples 1 to 7 or Comparative Examples 1 to 2 and the red resin composition of Production Example 1 were mixed in the ratios shown in Table 10. The CIE chromaticity coordinates and stimulus value (Y) were calculated using the transmission spectra obtained from the colored coating films of Examples 1 to 7 and Comparative Examples 1 to 2, respectively, the transmission spectra obtained from the colored coating film of Production Example 1, and the characteristic function of the C light source. The mixing ratios in Table 10 were all combinations in which the CIE chromaticity coordinates (x, y) = (0.150, 0.060). The values ​​of the stimulus value (Y) are shown in Table 10. A higher Y value indicates higher brightness.

[0746] [Table 10]

[0747]

[0748] In Table 10, each notation represents the following coloring agents.

[0749] I-5a-2: Compound (I-5a-2)

[0750] I-5b: Compound (I-5b)

[0751] I-4a-2: Compound (I-4a-2)

[0752] I-4b: Compound (I-4b)

[0753] I-9a-2: Compound (I-9a-2)

[0754] I-56a-2: Compound (I-56a-2)

[0755] I-59a-2: Compound (I-59a-2)

[0756] x1 : Compound (x1)

[0757] x2 : Compound (x2)

[0758] AR52 : Acid Red 52

Claims

Claim 1 A compound represented by formula (I). [Equation (I), R 1 ~R 4 and R 13 R represents a hydrocarbon group having 1 to 10 carbon atoms that may independently have hydrogen atoms or substituents. 5 ~R 12 represents a hydrocarbon group having 1 to 5 carbon atoms that may independently have a hydrogen atom, a halogen atom, or a substituent. 1 ...represents a divalent aromatic hydrocarbon group that may have substituents. 2 represents a divalent aromatic hydrocarbon group that may have substituents or a divalent aromatic complex group that may have substituents. 1 ... represents an aliphatic hydrocarbon group of valence a having 1 to 12 carbon atoms that may have substituents, or a group represented by formula (i). a represents an integer of 2 or more. b and c independently represent integers of 1 or more. d represents an integer of 0 or more. X c- represents the anion of c. [Equation (i), T 3 represents an α-valent aromatic hydrocarbon group that may have substituents or an α-valent aromatic complex group that may have substituents. 2 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that may have substituents. * indicates T 2 [Represents the bonding loss with.] Claim 2 In claim 1, R 1 and R 3 Representing a phenyl group that may have this substituent, and R 2 and R 4 ga represents a hydrocarbon group having 2 to 10 carbon atoms, and the above R 1 and R 3 A compound in which the phenyl group has an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions that are ortho positions with respect to N bonded to the phenyl group. Claim 3 A colored resin composition containing a coloring agent and a resin, wherein the coloring agent comprises a compound described in claim 1 or claim 2. Claim 4 A colored resin composition according to claim 3, additionally containing a polymerizable compound and a polymerization initiator. Claim 5 A color filter formed from a colored resin composition described in claim 4. Claim 6 A display device comprising a color filter as described in claim 5.

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