Compounds, coloring resin compositions, color filters and display devices

Abstract

The objective of this invention is to provide a compound capable of forming a color filter with excellent brightness. This objective is achieved by a compound represented by formula (I). In formula (I), T 1 represents a divalent aromatic hydrocarbon group that may have substituents, T 2 represents a divalent aromatic hydrocarbon group that may have substituents or a divalent aromatic heterocyclic group that may have substituents; L 1 represents an α-valent aliphatic hydrocarbon group with 1 to 12 carbon atoms that may have substituents, or a group represented by formula (i), where α represents an integer of 2 or more. In equation (i), T 3 indicates an α-valent aromatic hydrocarbon group that may have substituents or an α-valent aromatic heterocyclic group that may have substituents; L 2 represents a divalent aliphatic hydrocarbon group with 1 to 5 carbon atoms that may have substituents.

Description

Technical Field

[0001] This invention relates to a compound, a coloring resin composition, a color filter, and a display device. Prior Technology

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescence displays, and plasma displays, or in solid-state imaging elements such as charge-coupled devices (CCDs) or complementary metal-oxide-semiconductor (CMOS) sensors, are made from colored resin compositions. Various colorants are used as the colored resin composition for forming these color filters; for example, compounds represented by the following formulas (x1) or (x2) are known (Patent Document 1).

[0003] [Chemistry 1] [Existing technical documents] [Patent Literature]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2014-108975 Summary of the Invention

[0005] [The problem that the invention aims to solve] However, the brightness of color filters formed from color resin compositions containing the aforementioned compound is sometimes insufficient. Therefore, the objective of this invention is to provide a compound capable of forming color filters with excellent brightness. [Methods for solving problems]

[0006] The main points of this invention are as follows. [1] A compound represented by formula (I). [Chemistry 2] In formula (I), R1 to R4 and R13 independently represent a hydrogen atom or a hydrocarbon group with 1 to 10 carbon atoms that may have substituents; R5 to R12 independently represent hydrogen atoms, halogen atoms, or hydrocarbon groups with 1 to 5 carbon atoms that may have substituents; T1 represents a divalent aromatic hydrocarbon group that may have substituents; T 2 represents a divalent aromatic hydrocarbon group that may have substituents or a divalent aromatic heterocyclic group that may have substituents; L1 represents an α-valent aliphatic hydrocarbon group with 1 to 12 carbon atoms that may have substituents, or a group represented by formula (i); 'a' represents an integer greater than or equal to 2. b and c represent integers greater than 1 independently; d represents an integer greater than or equal to 0; X c- indicates a c-valent anion. [Chemistry 3] In formula (i), T 3 represents an α-valent aromatic hydrocarbon group that may have substituents or an α-valent aromatic heterocyclic group that may have substituents; L2 represents a divalent aliphatic hydrocarbon group with 1 to 5 carbon atoms that may have substituents; * indicates a bond with T2] [2] The compound as described in [1], wherein R1 and R3 represent phenyl groups that may have substituents, and R2 and R4 represent hydrocarbon groups having 2 to 10 carbon atoms. The phenyl groups of R1 and R3 have an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions adjacent to the N bonded to the phenyl group. [3] A coloring resin composition comprising a colorant and a resin, wherein the colorant comprises a compound as described in [1] or [2]. [4] The coloring resin composition as described in [3] further contains polymerizable compounds and polymerization initiators. [5] A color filter formed from a coloring resin composition as described in [3] or [4]. [6] A display device comprising a color filter as described in [5]. [The effects of the invention]

[0007] According to the present invention, a compound capable of forming a color filter with excellent brightness can be provided. Implementation

[0008] <Compound> The compounds of the present invention are those represented by formula (I) (hereinafter, sometimes referred to as compound (I)). Hereinafter, the present invention will be described in detail using formula (I), and compound (I) also includes tautomers of formula (I).

[0009] [Chemistry 4] In formula (I), R1 to R4 and R13 independently represent a hydrogen atom or a hydrocarbon group with 1 to 10 carbon atoms that may have substituents; R5 to R12 independently represent hydrogen atoms, halogen atoms, or hydrocarbon groups with 1 to 5 carbon atoms that may have substituents; T1 represents a divalent aromatic hydrocarbon group that may have substituents; T 2 represents a divalent aromatic hydrocarbon group that may have substituents or a divalent aromatic heterocyclic group that may have substituents; L1 represents an α-valent aliphatic hydrocarbon group with 1 to 12 carbon atoms that may have substituents, or a group represented by formula (i); 'a' represents an integer greater than or equal to 2. b and c represent integers greater than 1 independently; d represents an integer greater than or equal to 0; X c- indicates a c-valent anion. [Chemistry 5] In formula (i), T 3 represents an α-valent aromatic hydrocarbon group that may have substituents or an α-valent aromatic heterocyclic group that may have substituents; L2 represents a divalent aliphatic hydrocarbon group with 1 to 5 carbon atoms that may have substituents; 'a' indicates the same meaning as described above; * indicates a bond with T2]

[0010] As for the hydrocarbon groups with 1 to 10 carbon atoms represented by R1 to R4 and R13, aliphatic hydrocarbon groups and aromatic hydrocarbon groups can be listed. Aliphatic hydrocarbon groups can be saturated or unsaturated, and can be chain-like or alicyclic.

[0011] Examples of saturated or unsaturated chain hydrocarbon groups include: methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, and other straight-chain alkyl groups; isopropyl, (1-ethyl)propyl, isobutyl, dibutyl, tributyl, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tripentyl, (2-methyl)pentyl, (1-ethyl)pentyl, (3-ethyl)pentyl, (1-propyl)pentyl, (1-butyl)pentyl, and isohexyl. Branched chain alkyl groups such as (2-methyl)hexyl, (5-methyl)hexyl, (2-ethyl)hexyl, (1-butyl)hexyl, (2-methyl)heptyl, (2-ethyl)heptyl, (3-ethyl)heptyl, (2-methyl)octyl, (2-ethyl)octyl, etc.; vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl)vinyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl))vinyl, (1,2-dimethyl)propenyl, 2-pentenyl, etc.

[0012] Examples of saturated or unsaturated alicyclic hydrocarbon groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and other cycloalkyl groups; cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and other cycloalkenyl groups; norbornyl, adamantyl, bicyclo[2.2.2]octyl, etc.

[0013] Examples of aromatic hydrocarbon groups include: phenyl, 1-naphthyl, 2-naphthyl, etc.; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 2-methyl-6-ethylphenyl, 2,6-diethylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2-methyl-6-isopropylphenyl, 4-butylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, etc.; alkenylaryl groups such as 4-vinylphenyl, etc.

[0014] Regarding the hydrocarbon groups with 1 to 10 carbon atoms, as long as the upper limit of the carbon number is 10, it can be a group formed by combining two or more of the listed chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. Examples of such groups include: benzyl, phenethyl, 1-methyl-1-phenylethyl, and other arylalkyl groups; phenyl ethenyl, etc.; phenyl ethynyl, etc.; 1-methylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, etc. Alicyclic hydrocarbon groups such as cyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, and 3,3,5,5-tetramethylcyclohexyl are alicyclic hydrocarbon groups bonded with one or more alkyl or alicyclic hydrocarbon groups; alkyl groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, 2-methylcyclohexylmethyl, and cyclohexylethyl are alkyl groups bonded with one or more alicyclic hydrocarbon groups.

[0015] Substituents that may be present as hydrocarbon groups having 1 to 10 carbon atoms (hereinafter, sometimes referred to as substituent A) may be selected from at least one of the group consisting of halogen atoms, hydroxyl groups, alkoxy groups, methyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, -SO3- and -SO3M, where M represents a hydrogen atom or an alkali metal atom.

[0016] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, and other alkoxy groups with 1 to 4 carbon atoms. Examples of substituted amino groups include amino groups having one or two hydrocarbon groups, and examples of hydrocarbon groups having 1 to 10 carbon atoms. Examples of substituted amino groups include: N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-diethylamino, N-propylamino, N,N-dipropylamino, N-isopropylamino, N,N-diisopropylamino, N-phenylamino, N,N-diphenylamino, N,N-ethylmethylamino, N,N-methylphenylamino, N,N-ethylphenylamino, etc.

[0017] Examples of alkali metal atoms include sodium and potassium.

[0018] Halogen atoms represented by R5 to R12 can be listed as: fluorine atom, chlorine atom, bromine atom, and iodine atom.

[0019] As a hydrocarbon group with 1 to 5 carbons represented by R 5 to R 12, aliphatic hydrocarbon groups with 1 to 5 carbons can be listed. Specifically, groups with 1 to 5 carbons among the groups exemplified as aliphatic hydrocarbon groups R 1 to R 4 and R 13 can be listed.

[0020] Substituents that may be present in the hydrocarbon group having 1 to 5 carbon atoms include, for example, substituent A.

[0021] The divalent aromatic hydrocarbon groups represented by T1 and T2 are groups formed by replacing two hydrogen atoms directly bonded to the carbon atoms constituting the aromatic hydrocarbon ring with a chain bond. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group can be either a monocyclic or fused ring, such as benzene rings, naphthalene rings, anthracene rings, and structures formed by replacing at least one hydrogen atom of these aromatic hydrocarbon rings with a hydrocarbon group. Examples of the hydrocarbon groups include those represented by R1 to R4 and R13, which have 1 to 10 carbon atoms; preferably, they are saturated chain hydrocarbon groups, aryl or alkylaryl groups, and more preferably saturated chain hydrocarbon groups with 1 to 4 carbon atoms. The number of hydrocarbon groups bonded to the aromatic hydrocarbon ring is preferably 0 to 4, more preferably 0 to 3. Specifically, examples of divalent aromatic hydrocarbon groups include those represented by formulas (Ta-1) to (Ta-8).

[0022] [Chemistry 6]

[0023] The divalent aromatic heterocyclic group represented by T2 is a group formed by replacing two hydrogen atoms directly bonded to the atoms constituting the ring in an aromatic heterocycle with a hydroxyl group. The aromatic heterocycle constituting the divalent aromatic heterocyclic group can be either a monocyclic or fused ring, such as: pyrrole ring, oxazole ring, pyrazole ring, imidazole ring, thiazole ring, furan ring, thiophene ring, pyridine ring, pyrimidine ring, pyridazine ring, indole ring, benzimidazole ring, benzothiazole ring, quinoline ring, benzofuran ring, and structures formed by replacing at least one hydrogen atom of these aromatic heterocycles with a hydrocarbon group. As the hydrocarbon group, examples include groups with 1 to 10 carbon atoms represented by R1 to R4 and R13, preferably saturated chain hydrocarbon groups, aryl or alkylaryl groups. The number of hydrocarbon groups bonded to the aromatic heterocycle is preferably 0 to 4, more preferably 0 to 3.

[0024] Substituents that can be present in the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group include, for example, substituent A.

[0025] L1 represents an α-valent aliphatic hydrocarbon group with 1 to 12 carbon atoms, where the α hydrogen atoms constituting the aliphatic hydrocarbon are replaced by bonds. Preferably, the α bonds are located on different carbon atoms. Examples of α-valent aliphatic hydrocarbon groups include: α-valent chain hydrocarbon groups, α-valent alicyclic hydrocarbon groups, and α-valent groups formed by combining chain hydrocarbon groups and alicyclic hydrocarbon groups.

[0026] The α-valent chain hydrocarbon group can be saturated or unsaturated, but is preferably a saturated α-valent chain hydrocarbon group. Examples of saturated α-valent chain hydrocarbon groups include: methylene, ethyl, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, etc.; trialkyl groups represented by formulas (a-1) to (a-2) below; tetraalkyl groups represented by formula (a-3) below, etc. The number of carbon atoms in the α-valent chain hydrocarbon group is preferably 1 to 8, more preferably 1 to 6.

[0027] [Chemistry 7]

[0028] The α-valent alicyclic hydrocarbon group can be saturated or unsaturated, but is preferably an α-valent saturated alicyclic hydrocarbon group. Examples of α-valent saturated alicyclic hydrocarbon groups include: divalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,2-diyl, cyclohexyl-1,4-diyl, and norbornene-2,5-diyl; trivalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,3,5-triyl; and tetravalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,2,4,5-tetrayl. The number of carbon atoms in the α-valent alicyclic hydrocarbon group is preferably 3 to 10, and more preferably 3 to 6.

[0029] As an α-valent group formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, it is preferred to be an α-valent group formed by combining at least one chain hydrocarbon group and at least one saturated alicyclic hydrocarbon group, such as the groups represented by formulas (a-4) to (a-7) below.

[0030] [Chemistry 8]

[0031] Substituents that may be present in the α-valent aliphatic hydrocarbon groups having 1 to 12 carbon atoms include, for example, substituent A.

[0032] L1 can also be the basis represented by equation (i).

[0033] In formula (i), the α-valent aromatic hydrocarbon group represented by T3 is a group formed by replacing the α hydrogen atoms that are directly bonded to the carbon atoms constituting the aromatic hydrocarbon ring with bonded atoms. As an example of an aromatic hydrocarbon ring constituting an α-valent aromatic hydrocarbon group, structures that constitute an aromatic hydrocarbon ring as described above can be illustrated.

[0034] In formula (i), the α-valent aromatic heterocyclic group represented by T3 is a group in which the α hydrogen atoms directly bonded to the atoms constituting the ring in the aromatic heterocyclic group are replaced by bonded atoms. As an aromatic heterocyclic group constituting the α-valent aromatic heterocyclic group, the structures of aromatic heterocyclic groups constituting the divalent aromatic heterocyclic group can be described as examples.

[0035] Substituents that can be present in the α-valent aromatic hydrocarbon group and the α-valent aromatic heterocyclic group include, for example, substituent A.

[0036] In formula (i), the divalent aliphatic hydrocarbon groups with 1 to 5 carbons represented by L 2 can be listed as divalent chain hydrocarbon groups with 1 to 5 carbons and divalent alicyclic hydrocarbon groups with 1 to 5 carbons.

[0037] Divalent chain hydrocarbon groups can be saturated or unsaturated, but are preferably divalent saturated chain hydrocarbon groups. Examples of divalent saturated chain hydrocarbon groups include: methylene, ethyl, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and other alkyl diyl groups.

[0038] Divalent alicyclic hydrocarbon groups can be saturated or unsaturated, but are preferably divalent saturated alicyclic hydrocarbon groups. Examples of divalent saturated alicyclic hydrocarbon groups include cyclopropyl-1,2-diyl and cyclobutyl-1,3-diyl.

[0039] Substituents that may be present in the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms include, for example, substituent A.

[0040] As a basis represented by equation (i), specifically, the bases represented by equation (i1) or equation (i2) can be listed below.

[0041] [Chemistry 9] [In the formula, Li1~Li5 independently represent divalent saturated chain hydrocarbon groups with 1 to 5 carbon atoms.]

[0042] In equations (i1) to (i2), Li1 and Li2, as well as Li3 to Li5, can be the same or different, but it is preferable that they are the same.

[0043] As for the c-valent anion represented by X c-, well-known anions can be listed, specifically: halide ions such as fluoride ions, chloride ions, bromide ions, and iodide ions; boron-containing anions; aluminum-containing anions; fluoride-containing anions; and anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, with oxygen as an essential element.

[0044] As boron-containing anions and aluminum-containing anions, for example, the anions represented by the following formula (4) can be listed.

[0045] [Chemistry 10]

[0046] [In formula (4), W1 and W2 independently represent substituents that release protons from two monovalent proton-donating substituents; M represents boron or aluminum.]

[0047] Examples of substituents that are formed by the release of protons from two monovalent proton-donating substituents include groups derived from compounds having at least two monovalent proton-donating substituents (e.g., hydroxyl, carboxylic acid, etc.) from the release of protons from each of the two proton-donating substituents. Preferred compounds include catechol (which may have substituents), 2,3-dihydroxynaphthalene (which may have substituents), 2,2'-biphenol (which may have substituents), 3-hydroxy-2-naphthoic acid (which may have substituents), 2-hydroxy-1-naphthoic acid (which may have substituents), 1-hydroxy-2-naphthoic acid (which may have substituents), binaphthol (which may have substituents), salicylic acid (which may have substituents), benzilic acid (which may have substituents), or mandelic acid (which may have substituents).

[0048] In the exemplified compounds, substituents may include saturated hydrocarbon groups (e.g., alkyl, cycloalkyl, etc.), halogen atoms, haloalkyl groups, hydroxyl groups, amino groups, nitro groups, alkoxy groups, etc.

[0049] Examples of salicylic acids that can have substituents include: 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, and other monoaminosalicylic acids; 3-hydroxysalicylic acid (2,3-dihydroxybenzoic acid), 4-hydroxysalicylic acid (2,4-dihydroxybenzoic acid), 5-hydroxysalicylic acid (2,5-dihydroxybenzoic acid) Monohydroxysalicylic acids such as 6-hydroxysalicylic acid (2,6-dihydroxybenzoic acid); dihydroxysalicylic acids such as 4,5-dihydroxysalicylic acid and 4,6-dihydroxysalicylic acid; monohalosalicylic 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; dihalosalicylic acids such as 3,5-dichlorosalicylic acid, 3,5-dibromosalicylic acid, and 3,5-diiodosalicylic acid; and trihalosalicylic acids such as 3,5,6-trichlorosalicylic acid.

[0050] Examples of diphenylhydroxyacetic acid that can have substituents include...

[0051] [Chemistry 11]

[0052] Examples of mandelic acid that can have substituents include...

[0053] [Chemistry 12]

[0054] wait.

[0055] As preferred anions among those represented by formula (4), the following anions can be listed: the substituent anions (BC-1) to (BC-24) recorded in Table 1, and the anions (BC-25) to (BC-28) represented by formulas (BC-25), (BC-26), (BC-27) and (BC-28), respectively.

[0056] [Chemistry 13]

[0057] [Table 1] anions R 61 R 62 R 63 R 64 Anion (BC-1) H H H H Anion (BC-2) OH H H H Anion (BC-3) H OH H H Anion (BC-4) H H OH H Anion (BC-5) H H H OH Anion (BC-6) Cl H H H Anion (BC-7) H Cl H H Anion (BC-8) H H Cl H Anion (BC-9) H H H Cl Anion (BC-10) Br H H H Anion (BC-11) H Br H H Anion (BC-12) H H Br H Anion (BC-13) H H H Br Anion (BC-14) NH 2 H H H Anion (BC-15) H NH 2 H H Anion (BC-16) H H NH 2 H Anion (BC-17) H H H NH 2 Anion (BC-18) H tBu H tBu Anion (BC-19) H Cl H Cl Anion (BC-20) H Br H Br Anion (BC-21) H I H I Anion (BC-22) H OH OH H Anion (BC-23) OH H OH H Anion (BC-24) Cl Cl H Cl

[0058] [Chemistry 14]

[0059] [Chemistry 15]

[0060] [Chemistry 16]

[0061] [Chemistry 17]

[0062] From the viewpoint of solubility in organic solvents, the anions represented by formula (4) are preferably anions (BC-1), (BC-2), (BC-3), (BC-25), (BC-26), and (BC-27), more preferably anions (BC-1), (BC-2), and (BC-25), and even more preferably anions (BC-1) and (BC-2).

[0063] As fluorine-containing anions, examples include the anions represented by the following formulas (6), (7), (8), and (9).

[0064] [Chemistry 18]

[0065] [In formula (6), W3 and W4 independently represent fluorine atoms or fluorinated alkyl groups having 1 to 4 carbon atoms, or W3 and W4 together represent fluorinated alkyl diesters having 1 to 4 carbon atoms.]

[0066] [Chemistry 19]

[0067] [In formula (7), W5 to W7 independently represent fluorine atoms or fluorinated alkyl groups having 1 to 4 carbon atoms.]

[0068] [Chemistry 20]

[0069] [In formula (8), Y1 represents a fluorinated alkyl dimethyl group with 1 to 4 carbon atoms]

[0070] [Chemistry 21]

[0071] [In formula (9), Y2 represents a fluorinated alkyl group with 1 to 4 carbon atoms]

[0072] In formulas (6), (7) and (9), the fluorinated alkyl group having 1 to 4 carbon atoms is preferably a perfluoroalkyl group. Examples of such perfluoroalkyl groups include: -CF3, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -CF2CF2CF2CF3, -CF2CF(CF3)2, -C(CF3)3, etc.

[0073] In formulas (6) and (8), the fluorinated alkyl diester with 1 to 4 carbon atoms is preferably a perfluoroalkyl diester. Examples of perfluoroalkyl diesters include: -CF 2-, -CF 2CF 2-, -CF 2CF 2CF 2-, -C(CF 3) 2, -CF 2CF 2CF 2CF 2-, etc.

[0074] As an anion represented by formula (6) (hereinafter, sometimes referred to as "anion (6)"), anions represented by formulas (6-1) to (6-6) can be listed respectively (hereinafter, sometimes referred to as "anion (6-1)" to "anion (6-6)").

[0075] [Chemistry 22]

[0076] As an anion represented by formula (7) (hereinafter, sometimes referred to as "anion (7)"), the following formulas can be used to represent anions (7-1).

[0077] [Chemistry 23]

[0078] As an anion represented by formula (8) (hereinafter, sometimes referred to as "anion (8)"), anions represented by formulas (8-1) to (8-4) can be listed respectively (hereinafter, sometimes referred to as "anion (8-1)" to "anion (8-4)").

[0079] [Chemistry 24]

[0080] As an anion represented by formula (9) (hereinafter, sometimes referred to as "anion (9)"), anions represented by formulas (9-1) to (9-4) can be listed respectively (hereinafter, sometimes referred to as "anion (9-1)" to "anion (9-4)").

[0081] [Chemistry 25]

[0082] The c-valent anion represented by X c- is selected from at least one anion (i.e., a fluoride-containing anion) in the group consisting of anion (6), anion (7), anion (8), and anion (9), which can improve the solubility of compound (I) in an organic solvent. Among them, anion (6-1), anion (6-2), and anion (7-1) are preferred, and anion (6-2) is particularly preferred.

[0083] As the c-valent anion represented by X c-, examples include anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus, with oxygen as an essential element. More preferably, it is an anion of a heteropolyacid or isopolyacid containing tungsten as an essential element, and even more preferably, it is an anion of phosphotungstic acid, silicotungstic acid and tungsten-based isopolyacids.

[0084] Examples of anions containing tungsten as an essential element in heteropolyacids or isopolyacids include Keggin-type phosphotungstate ions α-[PW 12O 40] 3-, Dawson-type phosphotungstate ions α-[P 2W 18O 62] 6-, β-[P 2W 18O 62] 6-, Keggin-type silicotttate ions α-[SiW 12O 40] 4-, β-[SiW 12O 40] 4-, γ-[SiW 12O 40] 4-, and others such as [P 2W 17O 61] 10-, [P 2W 15O 56] 12-, [H 2P 2W 12O 48] 12-, and [NaP 5W 30O 110]. 14-, α-[SiW 9O 34] 10-, γ-[SiW 10O 36] 8-, α-[SiW 11O 39] 8-, β-[SiW 11O 39] 8-, [W 6O 19] 2-, [W 10O 32] 4-, WO 4 2-, etc.

[0085] In addition, among anions other than those of heteropolyacids or isopolyacids containing tungsten as an essential element, it is preferred to have an anion containing at least one element selected from the group consisting of silicon and phosphorus and oxygen. Examples of anions containing oxygen and at least one element selected from the group consisting of silicon and phosphorus include SiO3 2- and PO4 3-.

[0086] In particular, in terms of ease of synthesis and post-processing, it is preferable to use heteropolyacid anions such as Kekin-type phosphotungstate ion, Dawson-type phosphotungstate ion, Kekin-type silicotungstate ion, and [W 10O 32] 4-.

[0087] In equation (I), multiple R1~R13, T1, T2 and L1 can be the same or different, but it is preferred that they are the same.

[0088] R1 to R4 are preferably, independently, a saturated chain hydrocarbon group having 1 to 10 carbon atoms that may have substituents, an aryl group having 6 to 10 carbon atoms that may have substituents, or an alkylaryl group having 7 to 10 carbon atoms that may have substituents.

[0089] In particular, it is preferred that R1 and R3 are each independently an aryl group with 6 to 10 carbon atoms that may have substituents, or an alkylaryl group with 7 to 10 carbon atoms that may have substituents, and that R2 and R4 are each independently a saturated chain hydrocarbon group with 1 to 10 carbon atoms that may have substituents. More preferably, R1 and R3 are each independently a phenyl group that may have substituents, and R2 and R4 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms that may have substituents. Preferably, R1 and R3 are each independently a phenyl group that may have substituents, and are alkyl groups having 1 to 4 carbon atoms at at least one of two bonding positions adjacent to the N atom bonded to the phenyl group, and R2 and R4 are each independently a saturated chain hydrocarbon group having 1 to 6 carbon atoms that may have substituents. More preferably, R1 and R3 are each independently a phenyl group that may have substituents, and are alkyl groups having 1 to 4 carbon atoms at at least one of the two bonding positions adjacent to the N bonded to the phenyl group, and R2 and R4 are each independently a saturated chain hydrocarbon group having 2 to 6 carbon atoms that may have substituents. Preferably, R1 and R3 are phenyl groups that may have substituents, and are alkyl groups having 1 to 3 carbon atoms at two bonding positions adjacent to the N bonded to the phenyl group, and R2 and R4 are saturated chain hydrocarbon groups having 2 to 6 carbon atoms that may have substituents. Here, as substituents that the phenyl group may have, at least one may be selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, halogen atoms, hydroxyl groups, alkoxy groups, methyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, -SO3- and -SO3M (M is the same as described above), wherein, preferably at least one may be selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, halogen atoms, alkoxy groups and -SO3-, more preferably at least one may be selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms and -SO3-. In particular, the brightness of the obtained color filter can be further improved when the phenyl group does not have substituents, or has only at least one substituent selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, halogen atoms, hydroxyl groups, methyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, -SO3- and -SO3M (preferably only at least one substituent selected from the group consisting of alkyl groups having 1 to 4 carbon atoms and -SO3-). Furthermore, when the phenyl group has an alkoxy group (preferably a methoxy group) as a substituent, the lightfastness can be improved. The substitution position of the alkoxy group (preferably a methoxy group) is not particularly limited; by bonding it to a position opposite to the N group bonded to the phenyl group, the lightfastness can be further improved.

[0090] In the preferred states of R1 to R4, R1 and R3 are preferably any one of the bases represented by formulas (r1) to (r3). Furthermore, any one or more of the hydrogen atoms in the bases represented by formulas (r1) to (r3) may be substituted with -SO3-.

[0091] [Chemistry 26] [In the formula, Rr1 to Rr4 independently represent alkyl groups with 1 to 4 carbon atoms; * indicates a bond.]

[0092] Rr1~Rr4 are preferably methyl.

[0093] R5~R12 are preferably hydrogen atoms.

[0094] R 13 is preferably a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms that may have substituents, more preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 6 carbon atoms that may have substituents, and even more preferably a hydrogen atom, methyl, ethyl, n-propyl or isopropyl.

[0095] The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group represented by T1 is preferably a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of such ring is replaced by a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4). T1 is more preferably any of the groups represented by formulas (Ta-1) to (Ta-8), and particularly preferably the group represented by formula (Ta-8).

[0096] T2 is preferably a divalent aromatic hydrocarbon group that may have substituents. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is preferably a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of such ring is replaced by a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4). More preferably, it is a structure in which at least one hydrogen atom of a benzene ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms. T2 is further preferably any of the groups represented by formulas (Tb-1) to (Tb-10), more preferably any of the groups represented by formulas (Tb-3), (Tb-5), (Tb-6), (Tb-9), and (Tb-10), and particularly preferably any of the groups represented by formulas (Tb-5), (Tb-6), (Tb-9), and (Tb-10).

[0097] [Chemistry 27] [In the formula, * represents the bond with L1, and ** represents the bond with the nitrogen atom.]

[0098] L1 is preferably an α-valent aliphatic hydrocarbon group with 1 to 8 carbons that may have substituents, or in the group represented by formula (i), T3 is an α-valent aromatic hydrocarbon group that may have substituents, and L2 is a divalent saturated chain hydrocarbon group with 1 to 5 carbons. More preferably, it is an alkyldiyl group with 1 to 6 carbons that may have substituents, a divalent saturated alicyclic hydrocarbon group with 3 to 10 carbons that may have substituents, or a group represented by formula (i1) or formula (i2). Further preferably, it is an alkyldiyl group with 1 to 6 carbons that may have substituents, a divalent saturated alicyclic hydrocarbon group with 3 to 10 carbons that may have substituents, or any of the groups represented by formulas (i-1) to (i-4) below.

[0099] [Chemistry 28]

[0100] The c-valent anion represented by X c- is preferably 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 preferably, it is a halide ion or an anion of a heteropolyacid or isopolyacid containing tungsten as an essential element. Even more preferably, it is a halide ion, a Kegkin-type phosphotungstate ion or a Dawson-type phosphotungstate ion.

[0101] The substituent (i.e., substituent A) in compound (I) is preferably selected from at least one of the group consisting of halogen atoms, hydroxyl groups, alkoxy groups, substituted or unsubstituted amino groups, -SO3- and -SO3M, and more preferably at least one of the group consisting of halogen atoms, alkoxy groups, -SO3- and -SO3M.

[0102] a is preferably an integer greater than 2 and less than 6, more preferably an integer greater than 2 and less than 4, and even more preferably 2 or 3.

[0103] c is usually 1~14, preferably 1~12, even better 1~10, further preferably 1~6, and especially preferably 1~4.

[0104] b and d are determined based on a, c, and the number of -SO3- substituents in compound (I) (hereinafter sometimes referred to as e), and are usually adjusted so that the overall charge of formula (I) is 0. Therefore, a~d in formula (I) usually satisfy the relationship of the following formula (z). a×b=(c×d)+e …(z) [In the formula, a~d have the same meaning as described above; e represents the number of -SO3- substituents in compound (I)]

[0105] e is an integer greater than or equal to 0, preferably greater than or equal to 0 and less than (a+1), more preferably greater than or equal to 0 and less than a, and even more preferably 0 or a. In particular, when d is greater than or equal to 1, it is preferable that e is 0, that is, the compound (I) does not have -SO 3-, and when d is 0, it is preferable that e = a.

[0106] Furthermore, from the viewpoint of heat resistance and solvent resistance, it is preferable that X c- 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, d is 1 or more, and e is 0.

[0107] As compound (I), it is preferably a compound represented by formula (I-1) or formula (I-2).

[0108] [Chemistry 29] In formula (I-1), R101 and R103 are each independently a phenyl group that can have substituents. R102 and R104 are each independently a saturated chain hydrocarbon group with 1 to 10 carbon atoms that may have substituents. R 105~R 112 are hydrogen atoms. R 113 is a hydrogen atom or a saturated chain hydrocarbon group with 1 to 6 carbon atoms that may have substituents. T101 and T102 are divalent aromatic hydrocarbon groups that may have substituents, and 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 such ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms. L101 is an aliphatic hydrocarbon group with 1 to 8 carbon atoms that may have substituents, or a group represented by formula (i), where T3 is an aliphatic aromatic hydrocarbon group with 1 to 5 carbon atoms that may have substituents, and L2 is a divalent saturated chain hydrocarbon group with 1 to 5 carbon atoms. a101 is 2 or 3. d101 represents an integer greater than or equal to 1. b, c, and X c- represent the same meaning as described above.

[0109] [Chemistry 30] In formula (I-2), R201 and R203 are each independently a phenyl group that can have substituents. R 202 and R 204 are each independently a saturated chain hydrocarbon group with 1 to 10 carbon atoms that may have substituents. R 205~R 212 are hydrogen atoms. R 213 is a hydrogen atom or a saturated chain hydrocarbon group with 1 to 6 carbon atoms that may have substituents. T 201 and T 202 are divalent aromatic hydrocarbon groups that may have substituents, and 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 such ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms. L201 is an aliphatic hydrocarbon group with 1 to 8 carbon atoms that may have substituents, or a group represented by formula (i), where T3 is an aliphatic aromatic hydrocarbon group with 1 to 5 carbon atoms that may have substituents, and L2 is a divalent saturated chain hydrocarbon group with 1 to 5 carbon atoms. a201 and e201 are 2 or 3. In the compounds represented by formula (I-2), any e201 hydrogen atoms of R201~R213, T201, T202 and L201 are substituted with -SO3-.

[0110] The substituents that the phenyl groups represented by R 101, R 103, R 201, and R 203 may have include at least one selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, halogen atoms, hydroxyl groups, alkoxy groups, methyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, and -SO 3M (where M is a hydrogen atom or an alkali metal atom), wherein at least one selected from the group consisting of alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms is preferred. The halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described as substituent A.

[0111] R101, R103, R201, and R203 are preferably phenyl groups that may have substituents, and are alkyl groups having 1 to 4 carbon atoms at at least one (preferably both) of two bonding positions adjacent to the N bonded to the phenyl group. In particular, R101, R103, R201, and R203 are preferably any one of the groups represented by formulas (r1) to (r3), respectively, and are more preferably the groups represented by formulas (r1) or (r2) from the viewpoint of improving brightness, and are more preferably the groups represented by formula (r3) from the viewpoint of improving lightfastness.

[0112] R 102, R 104, R 202, and R 204 are preferably saturated chain hydrocarbon groups having 1 to 6 carbon atoms that may have substituents, and more preferably saturated chain hydrocarbon groups having 2 to 6 carbon atoms. Substituents (hereinafter referred to as substituent B) that may be present in the saturated chain hydrocarbon groups represented by R 102, R 104, R 202, and R 204 may be selected from at least one of the group consisting of halogen atoms, hydroxyl groups, alkoxy groups, methyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, and -SO 3M (where M is a hydrogen atom or an alkali metal atom). The halogen atoms, alkoxy groups, substituted amino groups, and alkali metal atoms are the same as those described as substituent A.

[0113] Substituents that can be present in saturated chain hydrocarbon groups with 1 to 6 carbon atoms, represented by R 113 and R 213, can be listed as substituents B.

[0114] Substituents that can be present in the divalent aromatic hydrocarbon groups represented by T 101 and T 201 can be exemplified by groups described as substituent B. T 101 and T 201 are preferably any of the groups represented by formulas (Ta-1) to (Ta-8), and more preferably the group represented by formula (Ta-8).

[0115] Substituents that can be present in the divalent aromatic hydrocarbon groups represented by T 102 and T 202 include groups described as substituent B, preferably at least one selected from the group consisting of halogen atoms and alkoxy groups. T 102 and T 202 are preferably divalent aromatic hydrocarbon groups that can have substituents, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring or a structure in which at least one hydrogen atom of the benzene ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms, more preferably any one of the groups represented by formulas (Tb-1) to (Tb-10), and particularly preferably any one of the groups represented by formulas (Tb-5), (Tb-6), (Tb-9), and (Tb-10).

[0116] In formulas (I-1) and (I-2), the α-valent saturated chain hydrocarbon group having 1 to 8 carbons represented by L 101 and L 201, the α-valent aromatic hydrocarbon group represented by T 3, and the substituent that L 2 in formula (i) may have are examples of substituent B. Preferably, L 101 and L 201 are alkyldiyl groups having 1 to 6 carbons that may have substituents, divalent saturated alicyclic hydrocarbon groups having 3 to 10 carbons that may have substituents, or any of the groups represented by formula (i1) or formula (i2).

[0117] a201 and e201 are preferably the same.

[0118] The compounds represented by formulas (I-1) and (I-2) are preferably zero in charge.

[0119] Furthermore, from the viewpoint of heat resistance and solvent resistance, the compound represented by formula (I-1) is preferred.

[0120] Specifically, compounds (I) can be exemplified as: compounds (I-1a-1) to (I-108a-1) and compounds (I-1a-2) to (I-108a-2) represented by formula (Ia), and compounds (I-1b) to (I-108b) represented by formula (Ib). Furthermore, the compounds represented by formula (Ib) represent compounds in compound (I) where b is 1 and d is 0. In the compounds represented by formula (Ib), any e2 of the hydrogen atoms in R1b to R13b, T1b, T2b, and L1b are substituted with -SO3-.

[0121] [Chemistry 31]

[0122] [Table 2] R 1a, R 3a R 2a, R 4a R 5a~R 12a R 13a T 1a T 2a L 1a a1 b1 X c1- d1 I-1a-1 r-1 Et H H Ta-8 Tb-5 l-1 2 1 Cl - 2 I-2a-1 r-2 Et H H Ta-8 Tb-5 l-1 2 1 Cl - 2 I-3a-1 r-3 Et H H Ta-8 Tb-5 l-1 2 1 Cl - 2 I-4a-1 r-1 Et H H Year-8 Tb-6 l-1 2 1 Cl − 2 5a-1 r-2 And H H Year-8 Tb-6 l-1 2 1 Cl − 2 6a-1 r-3 And H H Year-8 Tb-6 l-1 2 1 Cl − 2 7a-1 r-1 And H And Year-8 Tb-5 l-1 2 1 Cl − 2 8a-1 r-2 And H And Year-8 Tb-5 l-1 2 1 Cl − 2 9a-1 r-3 And H And Year-8 Tb-5 l-1 2 1 Cl − 2 10a-1 r-1 And H And Year-8 Tb-6 l-1 2 1 Cl − 2 11a-1 r-2 And H And Year-8 Tb-6 l-1 2 1 Cl − 2 12a-1 r-3 And H And Year-8 Tb-6 l-1 2 1 Cl − 2 13a-1 r-1 And H Pr Year-8 Tb-5 l-1 2 1 Cl - 2 I-14a-1 r-2 Et H Pr Ta-8 Tb-5 l-1 2 1 Cl - 2 I-15a-1 r-3 Et H Pr Ta-8 Tb-5 l-1 2 1 Cl - 2 I-16a-1 r-1 Et H Pr Ta-8 Tb-6 l-1 2 1 Cl - 2 I-17a-1 r-2 Et H Pr Ta-8 Tb-6 l-1 2 1 Cl - 2 I-18a-1 r-3 Et H Pr Ta-8 Tb-6 l-1 2 1 Cl - 2 I-19a-1 r-1 Et H H Ta-8 Tb-5 i-2 2 1 Cl - 2 I-20a-1 r-2 Et H H Ta-8 Tb-5 i-2 2 1 Cl - 2 I-21a-1 r-3 Et H H Ta-8 Tb-5 i-2 2 1 Cl - 2 I-22a-1 r-1 Et H H Ta-8 Tb-6 i-2 2 1 Cl - 2 I-23a-1 r-2 And H H Year-8 Tb-6 the 2 2 1 Cl − 2 24a-1 r-3 And H H Year-8 Tb-6 the 2 2 1 Cl − 2 25a-1 r-1 And H And Year-8 Tb-5 the 2 2 1 Cl − 2 26a-1 r-2 And H And Year-8 Tb-5 the 2 2 1 Cl − 2 27a-1 r-3 And H And Year-8 Tb-5 the 2 2 1 Cl − 2 28a-1 r-1 And H And Year-8 Tb-6 the 2 2 1 Cl − 2 29a-1 r-2 And H And Year-8 Tb-6 the 2 2 1 Cl − 2 30a-1 r-3 And H And Year-8 Tb-6 the 2 2 1 Cl − 2 31a-1 r-1 And H Pr Year-8 Tb-5 the 2 2 1 Cl − 2 32a-1 r-2 And H Pr Year-8 Tb-5 i-2 2 1 Cl - 2 I-33a-1 r-3 Et H Pr Ta-8 Tb-5 i-2 2 1 Cl - 2 I-34a-1 r-1 Et H Pr Ta-8 Tb-6 i-2 2 1 Cl - 2 I-35a-1 r-2 Et H Pr Ta-8 Tb-6 i-2 2 1 Cl - 2 I-36a-1 r-3 Et H Pr Ta-8 Tb-6 i-2 2 1 Cl - 2 I-37a-1 r-1 And H H Year-8 Tb-5 the 4 3 1 Cl − 3 38a-1 r-2 And H H Year-8 Tb-5 the 4 3 1 Cl − 3 39a-1 r-3 And H H Year-8 Tb-5 the 4 3 1 Cl − 3 40a-1 r-1 And H H Year-8 Tb-6 the 4 3 1 Cl − 3 41a-1 r-2 And H H Year-8 Tb-6 the 4 3 1 Cl − 3 42a-1 r-3 And H H Year-8 Tb-6 the 4 3 1 Cl − 3 43a-1 r-1 And H And Year-8 Tb-5 the 4 3 1 Cl − 3 44a-1 r-2 And H And Year-8 Tb-5 the 4 3 1 Cl − 3 45a-1 r-3 And H And Year-8 Tb-5 the 4 3 1 Cl − 3

[0123] [Figure3] R 1a、R 3a R 2a、R 4a R 5a~R 12a R 13a T 1a T 2a L 1a a1 b1 X c1- d1 I-46a-1 r-1 Et H Et Ta-8 Tb-6 i-4 3 1 Cl - 3 I-47a-1 r-2 Et H Et Ta-8 Tb-6 i-4 3 1 Cl - 3 I-48a-1 r-3 Et H Et Ta-8 Tb-6 i-4 3 1 Cl - 3 I-49a-1 r-1 Et H Pr Ta-8 Tb-5 i-4 3 1 Cl - 3 I-50a-1 r-2 Et H Pr Ta-8 Tb-5 i-4 3 1 Cl - 3 I-51a-1 r-3 Et H Pr Ta-8 Tb-5 i-4 3 1 Cl - 3 I-52a-1 r-1 Et H Pr Ta-8 Tb-6 i-4 3 1 Cl - 3 I-53a-1 r-2 Et H Pr Ta-8 Tb-6 i-4 3 1 Cl - 3 I-54a-1 r-3 Et H Pr Ta-8 Tb-6 i-4 3 1 Cl - 3 I-55a-1 r-1 Et H H Ta-8 Tb-9 l-1 2 1 Cl - 2 I-56a-1 r-2 Et H H Ta-8 Tb-9 l-1 2 1 Cl - 2 I-57a-1 r-3 Et H H Ta-8 Tb-9 l-1 2 1 Cl - 2 I-58a-1 r-1 Et H H Ta-8 Tb-10 l-1 2 1 Cl - 2 I-59a-1 r-2 And H H Year-8 Tb-10 l-1 2 1 Cl − 2 60a-1 r-3 And H H Year-8 Tb-10 l-1 2 1 Cl − 2 61a-1 r-1 And H And Year-8 Tb-9 l-1 2 1 Cl − 2 62a-1 r-2 And H And Year-8 Tb-9 l-1 2 1 Cl − 2 63a-1 r-3 And H And Year-8 Tb-9 l-1 2 1 Cl − 2 64a-1 r-1 And H And Year-8 Tb-10 l-1 2 1 Cl − 2 65a-1 r-2 And H And Year-8 Tb-10 l-1 2 1 Cl − 2 66a-1 r-3 And H And Year-8 Tb-10 l-1 2 1 Cl − 2 67a-1 r-1 And H Pr Year-8 Tb-9 l-1 2 1 Cl − 2 68a-1 r-2 And H Pr Year-8 Tb-9 l-1 2 1 Cl − 2 69a-1 r-3 And H Pr Year-8 Tb-9 l-1 2 1 Cl − 2 70a-1 r-1 And H Pr Year-8 Tb-10 l-1 2 1 Cl − 2 71a-1 r-2 And H Pr Year-8 Tb-10 l-1 2 1 Cl − 2 72a-1 r-3 And H Pr Year-8 Tb-10 l-1 2 1 Cl − 2 73a-1 r-1 And H H Year-8 Tb-9 the 2 2 1 Cl − 2 74a-1 r-2 And H H Year-8 Tb-9 the 2 2 1 Cl − 2 75a-1 r-3 And H H Year-8 Tb-9 the 2 2 1 Cl − 2 76a-1 r-1 And H H Year-8 Tb-10 the 2 2 1 Cl − 2 77a-1 r-2 And H H Year-8 Tb-10 the 2 2 1 Cl − 2 78a-1 r-3 And H H Year-8 Tb-10 the 2 2 1 Cl − 2 79a-1 r-1 And H And Year-8 Tb-9 the 2 2 1 Cl − 2 80a-1 r-2 And H And Year-8 Tb-9 the 2 2 1 Cl − 2 81a-1 r-3 And H And Year-8 Tb-9 the 2 2 1 Cl − 2 82a-1 r-1 And H And Year-8 Tb-10 i-2 2 1 Cl - 2 I-83a-1 r-2 Et H Et Ta-8 Tb-10 i-2 2 1 Cl - 2 I-84a-1 r-3 Et H Et Ta-8 Tb-10 i-2 2 1 Cl - 2 I-85a-1 r-1 Et H Pr Ta-8 Tb-9 i-2 2 1 Cl - 2 I-86a-1 r-2 Et H Pr Ta-8 Tb-9 i-2 2 1 Cl - 2 I-87a-1 r-3 Et H Pr Ta-8 Tb-9 i-2 2 1 Cl - 2 I-88a-1 r-1 Et H Pr Ta-8 Tb-10 i-2 2 1 Cl - 2 I-89a-1 r-2 Et H Pr Ta-8 Tb-10 i-2 2 1 Cl - 2 I-90a-1 r-3 Et H Pr Ta-8 Tb-10 i-2 2 1 Cl - 2

[0124] [Table 4] R 1a, R 3a R 2a, R 4a R 5a~R 12a R 13a T 1a T 2a L 1a a1 b1 X c1- d1 91a-1 r-1 And H H Year-8 Tb-9 the 4 3 1 Cl − 3 92a-1 r-2 And H H Year-8 Tb-9 the 4 3 1 Cl − 3 93a-1 r-3 And H H Year-8 Tb-9 the 4 3 1 Cl − 3 94a-1 r-1 And H H Year-8 Tb-10 the 4 3 1 Cl − 3 95a-1 r-2 And H H Year-8 Tb-10 the 4 3 1 Cl − 3 96a-1 r-3 And H H Year-8 Tb-10 the 4 3 1 Cl − 3 97a-1 r-1 And H And Year-8 Tb-9 the 4 3 1 Cl − 3 98a-1 r-2 And H And Year-8 Tb-9 the 4 3 1 Cl − 3 99a-1 r-3 And H And Year-8 Tb-9 the 4 3 1 Cl - 3 I-100a-1 r-1 Et H Et Ta-8 Tb-10 i-4 3 1 Cl - 3 I-101a-1 r-2 Et H Et Ta-8 Tb-10 i-4 3 1 Cl - 3 I-102a-1 r-3 Et H Et Ta-8 Tb-10 i-4 3 1 Cl - 3 I-103a-1 r-1 Et H Pr Ta-8 Tb-9 i-4 3 1 Cl - 3 I-104a-1 r-2 Et H Pr Ta-8 Tb-9 i-4 3 1 Cl - 3 I-105a-1 r-3 Et H Pr Ta-8 Tb-9 i-4 3 1 Cl - 3 I-106a-1 r-1 Et H Pr Ta-8 Tb-10 i-4 3 1 Cl - 3 I-107a-1 r-2 Et H Pr Ta-8 Tb-10 i-4 3 1 Cl - 3 I-108a-1 r-3 Et H Pr Ta-8 Tb-10 i-4 3 1 Cl - 3 I-1a-2 r-1 And H H Year-8 Tb-5 l-1 2 3 [PW 12O 40] 3- 2 2a-2 r-2 And H H Year-8 Tb-5 l-1 2 3 [PW 12O 40] 3- 2 3a-2 r-3 And H H Year-8 Tb-5 l-1 2 3 [PW 12O 40] 3- 2 4a-2 r-1 And H H Year-8 Tb-6 l-1 2 3 [PW 12O 40] 3- 2 5a-2 r-2 And H H Year-8 Tb-6 l-1 2 3 [PW 12O 40] 3- 2 I-6a-2 r-3 Et H H Ta-8 Tb-6 l-1 2 3 [PW 12O 40] 3- 2 I-7a-2 r-1 Et H Et Ta-8 Tb-5 l-1 2 3 [PW 12O 40] 3- 2 I-8a-2 r-2 Et H Et Ta-8 Tb-5 l-1 2 3 [PW 12O 40] 3- 2 I-9a-2 r-3 Et H Et Ta-8 Tb-5 l-1 2 3 [PW 12O 40] 3- 2 I-10a-2 r-1 And H And Year-8 Tb-6 l-1 2 3 [PW 12O 40] 3- 2 11a-2 r-2 And H And Year-8 Tb-6 l-1 2 3 [PW 12O 40] 3- 2 12a-2 r-3 And H And Year-8 Tb-6 l-1 2 3 [PW 12O 40] 3- 2 13a-2 r-1 And H Pr Year-8 Tb-5 l-1 2 3 [PW 12O 40] 3- 2 14a-2 r-2 And H Pr Year-8 Tb-5 l-1 2 3 [PW 12O 40] 3- 2 I-15a-2 r-3 Et H Pr Ta-8 Tb-5 l-1 2 3 [PW 12O 40] 3- 2 I-16a-2 r-1 Et H Pr Ta-8 Tb-6 l-1 2 3 [PW 12O 40] 3- 2 I-17a-2 r-2 Et H Pr Ta-8 Tb-6 l-1 2 3 [PW 12O 40] 3- 2 I-18a-2 r-3 Et H Pr Ta-8 Tb-6 l-1 2 3 [PW 12O 40] 3- 2 I-19a-2 r-1 Et H H Ta-8 Tb-5 i-2 2 3 [PW 12O 40] 3- 2 I-20a-2 r-2 Et H H Ta-8 Tb-5 i-2 2 3 [PW 12O 40] 3- 2 I-21a-2 r-3 Et H H Ta-8 Tb-5 i-2 2 3 [PW 12O 40] 3- 2 I-22a-2 r-1 Et H H Ta-8 Tb-6 i-2 2 3 [PW 12O 40] 3- 2 I-23a-2 r-2 Et H H Ta-8 Tb-6 i-2 2 3 [PW 12O 40] 3- 2 I-24a-2 r-3 Et H H Ta-8 Tb-6 i-2 2 3 [PW 12O 40] 3- 2 I-25a-2 r-1 Et H Et Ta-8 Tb-5 i-2 2 3 [PW 12O 40] 3- 2 I-26a-2 r-2 Et H Et Ta-8 Tb-5 i-2 2 3 [PW 12O 40] 3- 2 I-27a-2 r-3 Et H Et Ta-8 Tb-5 i-2 2 3 [PW 12O 40] 3- 2

[0125] [Table 5] R 1a, R 3a R 2a, R 4a R 5a~R 12a R 13a T 1a T 2a L 1a a1 b1 X c1- d1 I-28a-2 r-1 Et H Et Ta-8 Tb-6 i-2 2 3 [PW 12O 40] 3- 2 I-29a-2 r-2 Et H Et Ta-8 Tb-6 i-2 2 3 [PW 12O 40] 3- 2 I-30a-2 r-3 Et H Et Ta-8 Tb-6 i-2 2 3 [PW 12O 40] 3- 2 I-31a-2 r-1 Et H Pr Ta-8 Tb-5 i-2 2 3 [PW 12O 40] 3- 2 I-32a-2 r-2 Et H Pr Ta-8 Tb-5 i-2 2 3 [PW 12O 40] 3- 2 I-33a-2 r-3 Et H Pr Ta-8 Tb-5 i-2 2 3 [PW 12O 40] 3- 2 I-34a-2 r-1 Et H Pr Ta-8 Tb-6 i-2 2 3 [PW 12O 40] 3- 2 I-35a-2 r-2 Et H Pr Ta-8 Tb-6 i-2 2 3 [PW 12O 40] 3- 2 I-36a-2 r-3 Et H Pr Ta-8 Tb-6 i-2 2 3 [PW 12O 40] 3- 2 I-37a-2 r-1 Et H H Ta-8 Tb-5 i-4 3 1 [PW 12O 40] 3- 1 I-38a-2 r-2 Et H H Ta-8 Tb-5 i-4 3 1 [PW 12O 40] 3- 1 I-39a-2 r-3 Et H H Ta-8 Tb-5 i-4 3 1 [PW 12O 40] 3- 1 I-40a-2 r-1 Et H H Ta-8 Tb-6 i-4 3 1 [PW 12O 40] 3- 1 I-41a-2 r-2 Et H H Ta-8 Tb-6 i-4 3 1 [PW 12O 40] 3- 1 I-42a-2 r-3 Et H H Ta-8 Tb-6 i-4 3 1 [PW 12O 40] 3- 1 I-43a-2 r-1 Et H Et Ta-8 Tb-5 i-4 3 1 [PW 12O 40] 3- 1 I-44a-2 r-2 Et H Et Ta-8 Tb-5 i-4 3 1 [PW 12O 40] 3- 1 I-45a-2 r-3 Et H Et Ta-8 Tb-5 i-4 3 1 [PW 12O 40] 3- 1 I-46a-2 r-1 Et H Et Ta-8 Tb-6 i-4 3 1 [PW 12O 40] 3- 1 I-47a-2 r-2 Et H Et Ta-8 Tb-6 i-4 3 1 [PW 12O 40] 3- 1 I-48a-2 r-3 Et H Et Ta-8 Tb-6 i-4 3 1 [PW 12O 40] 3- 1 I-49a-2 r-1 Et H Pr Ta-8 Tb-5 i-4 3 1 [PW 12O 40] 3- 1 I-50a-2 r-2 Et H Pr Ta-8 Tb-5 i-4 3 1 [PW 12O 40] 3- 1 I-51a-2 r-3 Et H Pr Ta-8 Tb-5 i-4 3 1 [PW 12O 40] 3- 1 I-52a-2 r-1 Et H Pr Ta-8 Tb-6 i-4 3 1 [PW 12O 40] 3- 1 I-53a-2 r-2 Et H Pr Ta-8 Tb-6 i-4 3 1 [PW 12O 40] 3- 1 I-54a-2 r-3 Et H Pr Ta-8 Tb-6 i-4 3 1 [PW 12O 40] 3- 1 I-55a-2 r-1 Et H H Ta-8 Tb-9 l-1 2 3 [PW 12O 40] 3- 2 I-56a-2 r-2 Et H H Ta-8 Tb-9 l-1 2 3 [PW 12O 40] 3- 2 I-57a-2 r-3 Et H H Ta-8 Tb-9 l-1 2 3 [PW 12O 40] 3- 2 I-58a-2 r-1 And H H Year-8 Tb-10 l-1 2 3 [PW 12O 40] 3- 2 59a-2 r-2 And H H Year-8 Tb-10 l-1 2 3 [PW 12O 40] 3- 2 60a-2 r-3 And H H Year-8 Tb-10 l-1 2 3 [PW 12O 40] 3- 2 61a-2 r-1 And H And Year-8 Tb-9 l-1 2 3 [PW 12O 40] 3- 2 62a-2 r-2 And H And Year-8 Tb-9 l-1 2 3 [PW 12O 40] 3- 2 I-63a-2 r-3 Et H Et Ta-8 Tb-9 l-1 2 3 [PW 12O 40] 3- 2 I-64a-2 r-1 Et H Et Ta-8 Tb-10 l-1 2 3 [PW 12O 40] 3- 2 I-65a-2 r-2 Et H Et Ta-8 Tb-10 l-1 2 3 [PW 12O 40] 3- 2 I-66a-2 r-3 Et H Et Ta-8 Tb-10 l-1 2 3 [PW 12O 40] 3- 2 I-67a-2 r-1 Et H Pr Ta-8 Tb-9 l-1 2 3 [PW 12O 40] 3- 2 I-68a-2 r-2 Et H Pr Ta-8 Tb-9 l-1 2 3 [PW 12O 40] 3- 2 I-69a-2 r-3 Et H Pr Ta-8 Tb-9 l-1 2 3 [PW 12O 40] 3- 2 I-70a-2 r-1 Et H Pr Ta-8 Tb-10 l-1 2 3 [PW 12O 40] 3- 2 I-71a-2 r-2 Et H Pr Ta-8 Tb-10 l-1 2 3 [PW 12O 40] 3- 2 I-72a-2 r-3 Et H Pr Ta-8 Tb-10 l-1 2 3 [PW 12O 40] 3- 2

[0126] [Table 6] R 1a, R 3a R 2a, R 4a R 5a~R 12a R 13a T 1a T 2a L 1a a1 b1 X c1- d1 I-73a-2 r-1 Et H H Ta-8 Tb-9 i-2 2 3 [PW 12O 40] 3- 2 I-74a-2 r-2 Et H H Ta-8 Tb-9 i-2 2 3 [PW 12O 40] 3- 2 I-75a-2 r-3 Et H H Ta-8 Tb-9 i-2 2 3 [PW 12O 40] 3- 2 I-76a-2 r-1 Et H H Ta-8 Tb-10 i-2 2 3 [PW 12O 40] 3- 2 I-77a-2 r-2 Et H H Ta-8 Tb-10 i-2 2 3 [PW 12O 40] 3- 2 I-78a-2 r-3 Et H H Ta-8 Tb-10 i-2 2 3 [PW 12O 40] 3- 2 I-79a-2 r-1 Et H Et Ta-8 Tb-9 i-2 2 3 [PW 12O 40] 3- 2 I-80a-2 r-2 Et H Et Ta-8 Tb-9 i-2 2 3 [PW 12O 40] 3- 2 I-81a-2 r-3 Et H Et Ta-8 Tb-9 i-2 2 3 [PW 12O 40] 3- 2 I-82a-2 r-1 Et H Et Ta-8 Tb-10 i-2 2 3 [PW 12O 40] 3- 2 I-83a-2 r-2 Et H Et Ta-8 Tb-10 i-2 2 3 [PW 12O 40] 3- 2 I-84a-2 r-3 Et H Et Ta-8 Tb-10 i-2 2 3 [PW 12O 40] 3- 2 I-85a-2 r-1 Et H Pr Ta-8 Tb-9 i-2 2 3 [PW 12O 40] 3- 2 I-86a-2 r-2 Et H Pr Ta-8 Tb-9 i-2 2 3 [PW 12O 40] 3- 2 I-87a-2 r-3 Et H Pr Ta-8 Tb-9 i-2 2 3 [PW 12O 40] 3- 2 I-88a-2 r-1 Et H Pr Ta-8 Tb-10 i-2 2 3 [PW 12O 40] 3- 2 I-89a-2 r-2 Et H Pr Ta-8 Tb-10 i-2 2 3 [PW 12O 40] 3- 2 I-90a-2 r-3 Et H Pr Ta-8 Tb-10 i-2 2 3 [PW 12O 40] 3- 2 I-91a-2 r-1 Et H H Ta-8 Tb-9 i-4 3 1 [PW 12O 40] 3- 1 I-92a-2 r-2 Et H H Ta-8 Tb-9 i-4 3 1 [PW 12O 40] 3- 1 I-93a-2 r-3 Et H H Ta-8 Tb-9 i-4 3 1 [PW 12O 40] 3- 1 I-94a-2 r-1 Et H H Ta-8 Tb-10 i-4 3 1 [PW 12O 40] 3- 1 I-95a-2 r-2 Et H H Ta-8 Tb-10 i-4 3 1 [PW 12O 40] 3- 1 I-96a-2 r-3 Et H H Ta-8 Tb-10 i-4 3 1 [PW 12O 40] 3- 1 I-97a-2 r-1 Et H Et Ta-8 Tb-9 i-4 3 1 [PW 12O 40] 3- 1 I-98a-2 r-2 Et H Et Ta-8 Tb-9 i-4 3 1 [PW 12O 40] 3- 1 I-49a-2 r-3 Et H Et Ta-8 Tb-9 i-4 3 1 [PW 12O 40] 3- 1 I-100a-2 r-1 Et H Et Ta-8 Tb-10 i-4 3 1 [PW 12O 40] 3- 1 I-101a-2 r-2 Et H Et Ta-8 Tb-10 i-4 3 1 [PW 12O 40] 3- 1 I-102a-2 r-3 Et H Et Ta-8 Tb-10 i-4 3 1 [PW 12O 40] 3- 1 I-103a-2 r-1 Et H Pr Ta-8 Tb-9 i-4 3 1 [PW 12O 40] 3- 1 I-104a-2 r-2 Et H Pr Ta-8 Tb-9 i-4 3 1 [PW 12O 40] 3- 1 I-105a-2 r-3 Et H Pr Ta-8 Tb-9 i-4 3 1 [PW 12O 40] 3- 1 I-106a-2 r-1 Et H Pr Ta-8 Tb-10 i-4 3 1 [PW 12O 40] 3- 1 I-107a-2 r-2 Et H Pr Ta-8 Tb-10 i-4 3 1 [PW 12O 40] 3- 1 I-108a-2 r-3 Et H Pr Ta-8 Tb-10 i-4 3 1 [PW 12O 40] 3- 1

[0127] [Chemical Formula 32]

[0128] [Table 7] R 1b, R 3b R 2b, R 4b R 5b~R 12b R 13b T 1b T 2b L 1b a2 e2 1b r-1 And H H Year-8 Tb-5 l-1 2 2 2b r-2 And H H Year-8 Tb-5 l-1 2 2 3b r-3 And H H Year-8 Tb-5 l-1 2 2 4b r-1 And H H Year-8 Tb-6 l-1 2 2 5b r-2 And H H Year-8 Tb-6 l-1 2 2 6b r-3 And H H Ta-8 Tb-6 l-1 2 2 I-7b r-1 And H And Ta-8 Tb-5 l-1 2 2 I-8b r-2 And H And Ta-8 Tb-5 l-1 2 2 I-9b r-3 And H And Ta-8 Tb-5 l-1 2 2 I-10b r-1 And H And Ta-8 Tb-6 l-1 2 2 I-11b r-2 And H And Ta-8 Tb-6 l-1 2 2 I-12b r-3 And H And Ta-8 Tb-6 l-1 2 2 I-13b r-1 And H Pr Ta-8 Tb-5 l-1 2 2 I-14b r-2 And H Pr Ta-8 Tb-5 l-1 2 2 I-15b r-3 And H Pr Ta-8 Tb-5 l-1 2 2 I-16b r-1 And H Pr Ta-8 Tb-6 l-1 2 2 I-17b r-2 And H Pr Ta-8 Tb-6 l-1 2 2 18b r-3 And H Pr Year-8 Tb-6 l-1 2 2 19b r-1 And H H Year-8 Tb-5 the 2 2 2 20b r-2 And H H Year-8 Tb-5 the 2 2 2 21b r-3 And H H Year-8 Tb-5 the 2 2 2 22b r-1 And H H Year-8 Tb-6 the 2 2 2 23b r-2 And H H Take-8 Tb-6 in-2 2 2 I-24b r-3 One H H Take-8 Tb-6 in-2 2 2 I-25b r-1 One H One Take-8 Tb-5 in-2 2 2 I-26b r-2 One H One Take-8 Tb-5 in-2 2 2 I-27b r-3 One H One Take-8 Tb-5 in-2 2 2 I-28b r-1 One H One Take-8 Tb-6 in-2 2 2 I-29b r-2 And H And Year-8 Tb-6 the 2 2 2 30b r-3 And H And Year-8 Tb-6 the 2 2 2 31b r-1 And H Pr Year-8 Tb-5 the 2 2 2 32b r-2 And H Pr Year-8 Tb-5 the 2 2 2 33b r-3 And H Pr Year-8 Tb-5 the 2 2 2 34b r-1 And H Pr Year-8 Tb-6 the 2 2 2 35b r-2 And H Pr Year-8 Tb-6 the 2 2 2 36b r-3 And H Pr Year-8 Tb-6 the 2 2 2 37b r-1 And H H Year-8 Tb-5 the 4 3 3 38b r-2 And H H Year-8 Tb-5 the 4 3 3 39b r-3 And H H Year-8 Tb-5 the 4 3 3 40b r-1 And H H Year-8 Tb-6 the 4 3 3 41b r-2 And H H Year-8 Tb-6 the 4 3 3 42b r-3 And H H Year-8 Tb-6 the 4 3 3 43b r-1 And H And Year-8 Tb-5 the 4 3 3 44b r-2 And H And Year-8 Tb-5 the 4 3 3 45b r-3 And H And Year-8 Tb-5 the 4 3 3

[0129] [Table 8] R 1b, R 3b R 2b, R 4b R 5b~R 12b R 13b T 1b T 2b L 1b a2 e2 I-46b r-1 Et H Et Ta-8 Tb-6 i-4 3 3 I-47b r-2 Et H Et Ta-8 Tb-6 i-4 3 3 I-48b r-3 Et H Et Ta-8 Tb-6 i-4 3 3 I-49b r-1 Et H Pr Ta-8 Tb-5 i-4 3 3 I-50b r-2 Et H Pr Year-8 Tb-5 the 4 3 3 51b r-3 And H Pr Year-8 Tb-5 the 4 3 3 52b r-1 And H Pr Year-8 Tb-6 the 4 3 3 53b r-2 And H Pr Year-8 Tb-6 the 4 3 3 54b r-3 And H Pr Year-8 Tb-6 the 4 3 3 55b r-1 And H H Year-8 Tb-9 l-1 2 2 56b r-2 And H H Year-8 Tb-9 l-1 2 2 57b r-3 And H H Year-8 Tb-9 l-1 2 2 58b r-1 And H H Year-8 Tb-10 l-1 2 2 59b r-2 And H H Year-8 Tb-10 l-1 2 2 60b r-3 And H H Year-8 Tb-10 l-1 2 2 61b r-1 And H And Year-8 Tb-9 l-1 2 2 I-62b r-2 And H And Ta-8 Tb-9 l-1 2 2 I-63b r-3 And H And Ta-8 Tb-9 l-1 2 2 I-64b r-1 And H And Ta-8 Tb-10 l-1 2 2 I-65b r-2 And H And Ta-8 Tb-10 l-1 2 2 I-66b r-3 And H And Ta-8 Tb-10 l-1 2 2 I-67b r-1 And H Pr Year-8 Tb-9 l-1 2 2 68b r-2 And H Pr Year-8 Tb-9 l-1 2 2 69b r-3 And H Pr Year-8 Tb-9 l-1 2 2 70b r-1 And H Pr Year-8 Tb-10 l-1 2 2 71b r-2 And H Pr Year-8 Tb-10 l-1 2 2 72b r-3 And H Pr Year-8 Tb-10 l-1 2 2 73b r-1 And H H Year-8 Tb-9 the 2 2 2 74b r-2 And H H Year-8 Tb-9 the 2 2 2 75b r-3 And H H Year-8 Tb-9 the 2 2 2 76b r-1 And H H Year-8 Tb-10 the 2 2 2 77b r-2 And H H Year-8 Tb-10 the 2 2 2 78b r-3 And H H Year-8 Tb-10 in-2 2 2 I-79b r-1 One H One Take-8 Tb-9 in-2 2 2 I-80b r-2 One H One Take-8 Tb-9 in-2 2 2 I-81b r-3 One H One Take-8 Tb-9 in-2 2 2 I-82b r-1 One H One Take-8 Tb-10 in-2 2 2 I-83b r-2 One H One Take-8 Tb-10 in-2 2 2 I-84b r-3 One H Et Ta-8 Tb-10 i-2 2 2 I-85b r-1 Et H Pr Ta-8 Tb-9 i-2 2 2 I-86b r-2 Et H Pr Ta-8 Tb-9 i-2 2 2 I-87b r-3 Et H Pr Ta-8 Tb-9 i-2 2 2 I-88b r-1 Et H Pr Ta-8 Tb-10 i-2 2 2 I-89b r-2 Et H Pr Ta-8 Tb-10 i-2 2 2 I-90b r-3 Et H Pr Ta-8 Tb-10 i-2 2 2

[0130] [Table 9] R 1b, R 3b R 2b, R 4b R 5b~R 12b R 13b T 1b T 2b L 1b a2 e2 I-91b r-1 Et H H Ta-8 Tb-9 i-4 3 3 I-92b r-2 Et H H Ta-8 Tb-9 i-4 3 3 I-93b r-3 Et H H Ta-8 Tb-9 i-4 3 3 I-94b r-1 And H H Year-8 Tb-10 the 4 3 3 95b r-2 And H H Year-8 Tb-10 the 4 3 3 96b r-3 And H H Year-8 Tb-10 the 4 3 3 97b r-1 And H And Year-8 Tb-9 the 4 3 3 98b r-2 And H And Year-8 Tb-9 the 4 3 3 99b r-3 And H And Year-8 Tb-9 i-4 3 3 I-100b r-1 Et H Et Ta-8 Tb-10 i-4 3 3 I-101b r-2 Et H Et Ta-8 Tb-10 i-4 3 3 I-102b r-3 Et H Et Ta-8 Tb-10 i-4 3 3 I-103b r-1 Et H Pr Ta-8 Tb-9 i-4 3 3 I-104b r-2 Et H Pr Ta-8 Tb-9 i-4 3 3 I-105b r-3 Et H Pr Ta-8 Tb-9 i-4 3 3 I-106b r-1 Et H Pr Ta-8 Tb-10 i-4 3 3 I-107b r-2 Et H Pr Ta-8 Tb-10 i-4 3 3 I-108b r-3 Et H Pr Ta-8 Tb-10 i-4 3 3

[0131] In Tables 2 to 9, H represents a hydrogen atom, Et represents an ethyl group, Pr represents a n-propyl group, r-1 to r-3 represent the groups represented by formulas (r-1) to (r-3) below, Ta-8 represents the group represented by formula (Ta-8) below, Tb-5 to Tb-6 and Tb-9 to Tb-10 represent the groups represented by formulas (Tb-5) to (Tb-6) and (Tb-9) to (Tb-10) below, l-1 represents the group represented by formula (l-1) below, and i-2 and i-4 represent the groups represented by formulas (i-2) and (i-4) below.

[0132] [Chemistry 33] [In the formula, * indicates a bond with a nitrogen atom]

[0133] [Chemistry 34] [In the formula, * represents a bond]

[0134] [Chemistry 35] [In the formula, * represents a bond with L 1a or L 1b, and ** represents a bond with a nitrogen atom.]

[0135] [Chemistry 36] [In the formula, * indicates a bond with T 2a or T 2b]

[0136] As compound (I), preferred are 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), more preferably compounds (I-1a-1) to (I-18a-1), and compounds (I-55a-1) to (I-90b). (I-72a-1), compound (I-1a-2) ~ compound (I-18a-2), compound (I-55a-2) ~ compound (I-72a-2), compound (I-1b) ~ compound (I-18b) and compound (I-55b) ~ compound (I-72b), and preferably compound (I-1a-2) ~ compound (I-18a-2), compound (I-55a-2) ~ compound (I-72a-2), compound (I-1b) ~ compound (I-18b) and compound (I-55b) ~ compound (I-72b). From the viewpoint of improving brightness, R1a, R3a, R1b, and R3b are preferably compounds represented by formula (r-1) or formula (r-2). From the viewpoint of improving lightfastness, R1a, R3a, R1b, and R3b are preferably compounds represented by formula (r-3). 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 even more preferred.

[0137] Compound (I) can be manufactured, for example, by methods (1) to (3) described below.

[0138] (1) Method for manufacturing compounds (I) where X c- is a halide ion (hereinafter, sometimes referred to as compound (I')). Compound (I') can be produced, for example, by reacting a compound represented by formula (BI) with a compound represented by formula (CI).

[0139] [Chemistry 37] [In formulas (BI) and (CI), R1~R13, T2, L1, and a represent the same meanings as described above; T1B represents a group in T1 where the bond different from the bond bonded to the nitrogen atom is replaced by a hydrogen atom.]

[0140] The amount of compound represented by formula (CI) used is preferably 0.5 mol or more and 10 mol or less, more preferably 1 mol or more and 4 mol or less, relative to 1 mol of compound represented by formula (BI).

[0141] The preferred reaction temperature is 30℃~180℃, more preferably 80℃~130℃. The preferred reaction time is 1 hour~12 hours, more preferably 1 hour~8 hours.

[0142] The reaction can be carried out in the presence of an organic solvent or in the absence of a solvent, but in terms of yield, it is preferred to carry it out in an organic solvent. Examples of organic solvents include: hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and chloroform; alcohol solvents such as methanol, ethanol, isopropanol, and butanol; nitro hydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; and amide solvents such as 1-methyl-2-pyrrolidone. The amount of organic solvent used is preferably 1 part by mass and 20 parts by mass or less, more preferably 2 parts by mass and 10 parts by mass or less, relative to 1 part by mass of the compound represented by formula (BI).

[0143] From the viewpoint of yield, the reaction is preferably carried out in the presence of a condensing agent. Examples of condensing agents include phosphoric acid, polyphosphoric acid, phosphorus oxychloride and other phosphorus oxyhalides, sulfuric acid, thionyl chloride and other thionyl halides. When phosphorus oxyhalides, thionyl halides, etc. are used as condensing agents, and when the relationship of formula (z1) is satisfied, a compound (I') in which Xc- is a halide ion can be obtained. a×be>0 …(Z1) [In the above formula, the meanings of a and b are the same as those of a and b in formula (I); e represents the number of -SO3- substituents present in compound (I')] The amount of condensing agent used is preferably 0.1 parts by mass and less than 20 parts by mass relative to 1 part by mass of the compound represented by formula (BI), and more preferably 0.2 parts by mass and less than 10 parts by mass.

[0144] There are no particular limitations on the method for obtaining compound (I') from the reaction mixture, and various known methods can be used. After extraction, the residue can also be purified by column chromatography or recrystallization.

[0145] As a method for manufacturing compound (BI), various known methods can be used, such as the method described in West German Patent Application No. P3928243.0. In addition, as needed, it can be further purified by known methods such as separation based on recrystallization or chromatography.

[0146] Various known methods can be listed as methods for manufacturing compounds (CI). In addition, as needed, known methods such as recrystallization or chromatography can be used for further purification.

[0147] (2) Method for manufacturing compounds (I) where X c- is an anion other than a halide ion (hereinafter referred to as anion X 1) (hereinafter, sometimes referred to as compound (I'')). Compound (I'') can be prepared by mixing compound (I') with an alkali metal salt or protic acid of anion X 1. Examples of alkali metals include lithium, sodium, and potassium.

[0148] The amount of alkali metal salt or protic acid of anion X1 relative to compound (I') can be added in a stoichiometric ratio of the charge balance between the cation and anion X1 in compound (I'), and is 1 mol relative to compound (I'), for example preferably 0.5 mol or more and 8 mol or less, more preferably 1 mol or more and 3 mol or less.

[0149] The mixing of compound (I') and the alkali metal salt or protic acid of anion X 1 can be carried out by dissolving both in the following solvent, or by not dissolving both.

[0150] 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. From the viewpoint of solubility, a solvent preferably selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, methanol, ethanol, isopropanol and water. The amount of solvent used relative to 1 part by mass of compound (I') is preferably 1 part by mass or more and 30 parts by mass or less, more preferably 2 parts by mass or more and 20 parts by mass or less. When the solvent is water, acids such as acetic acid or hydrochloric acid can also be added.

[0151] The mixing temperature of compound (I') and the alkali metal salt or protic acid of anion X1 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.

[0152] When using a water-miscible solvent, the solution is mixed and stirred for 1 to 3 hours as needed, then the solvent is removed to obtain compound (I''). The obtained compound (I'') can also be washed with deionized water or methanol, if necessary.

[0153] When using a solvent immiscible with water, the reaction mixture is mixed with ion-exchanged water and stirred for 1 to 3 hours as needed. The organic layer is then obtained by separation, yielding a solution containing compound (I''). The solution can also be washed with ion-exchanged water if necessary. The solvent is removed from the solution containing compound (I''), thereby obtaining compound (I'').

[0154] (3) Methods for manufacturing compounds in which X c- (i.e., d=0) does not exist (hereinafter, sometimes referred to as compound (I''')). Compound (I''') can be produced by mixing compound (I') with sulfuric acid.

[0155] The amount of sulfuric acid used relative to compound (I') can be added according to the stoichiometric ratio of the charge balance between the cations in compound (I') and -SO3-, and is, for example, 0.5 mol or more and 8 mol or less, preferably 1 mol or more and 3 mol or less, relative to 1 mol of compound (I'). Furthermore, the sulfuric acid can be used as a reaction solvent. When sulfuric acid is used as a solvent, the amount of sulfuric acid used relative to 1 mol of compound (I') is, for example, 20 mol or more, preferably 25 mol or more. There is no particular upper limit to the amount of sulfuric acid used when sulfuric acid is used as a solvent; it is, for example, 100 parts by mass or less, preferably 50 parts by mass or less, relative to 1 part by mass of compound (I').

[0156] 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.

[0157] The mixture obtained by mixing compound (I') with sulfuric acid is suspended by adding ice water and then filtered to obtain compound (I'''). Alternatively, it can be further purified by known methods such as recrystallization or chromatography, if necessary.

[0158] <Coloring Resin Composition> The coloring resin composition of the present invention contains a colorant (hereinafter, sometimes referred to as colorant (A)) and a resin (hereinafter, sometimes referred to as resin (B)), wherein the colorant comprises compound (I). The coloring resin composition of the present invention preferably further comprises a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D)). The coloring resin composition of the present invention preferably further contains a solvent (hereinafter, sometimes referred to as solvent (E)). The coloring resin composition of the present invention may further include a leveling agent (hereinafter, sometimes referred to as leveling agent (F)). Furthermore, unless otherwise specified in this specification, the compounds exemplified as components may be used alone or in combination.

[0159] <Coloring Agent (A)> The colorant (A) contains compound (I). This results in a color filter with good brightness, and preferably, also enables the thin-film fabrication of the obtained color filter. Examples of compound (I) are provided, and their preferred forms are also the same.

[0160] Colorant (A) may also contain dyes (hereinafter, sometimes referred to as dyes (A1-1)) and / or pigments (hereinafter, sometimes referred to as pigments (A1-2)) other than compound (I). Hereinafter, dyes (A1-1) and pigments (A1-2) are sometimes referred to together as colorant (A1). These may be used alone or in combination of two or more.

[0161] The dye (A1-1) is not particularly limited as long as it does not contain compound (I), and well-known dyes can be used, such as 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 well-known dyes recorded in dyeing notes (Shikisensha Co., Ltd.). Furthermore, based on chemical structure, examples include: azo dyes, cyanide dyes, triphenylmethane dyes, xanthracene dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methylene dyes, azomethylene dyes, squaric acid lactone dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes, etc. Among these, organic solvent-soluble dyes are preferred.

[0162] As a dye (A1-1), specifically, the following can be listed: 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; 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; CI Solvent Orange: 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; CI Solvent Violet: 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; Solvent Blue (CI) 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; CI solvent green dyes include grades 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, and 35. CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 1 57, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red: 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 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; 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; CI Acid Violet: 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; Acid Blue (CI) 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, 1 26, 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; CI acid green dyes include 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, and 109. 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; CI Direct Red: 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange: 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI direct violet: 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI (Direct Blue) 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 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, 1 67, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI direct green dyes include 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, and 82. CI Disperse Yellow: 51, 54, 76; CI Disperse Violet 26, 27; CI disperse blue dyes, including CI disperse blue 1, 14, 56, and 60; CI Basic Red 1, 9, 10; CI Basic Blue: 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI basic green 1 and other CI basic dyes; CI Reactive Yellow: 2, 76, 116; CI Reactive Orange 16; CI reactive dyes such as CI reactive red 36; CI mordant yellow: 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red: 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant Orange: 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI mordant violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue: 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI mordant green dyes include grades 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, and 53. CI vat green, etc., are dyes with CI vat dye numbers.

[0163] As for pigments (A1-2), there are no particular limitations as long as they do not contain compound (I), and well-known pigments can be used, such as those classified as pigments in the Dye Index (published by The Society of Dyers and Colourists). As pigments classified as pigments, examples include: 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, etc. CI Pigment Orange includes orange pigments in grades 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, and 73. CI pigment red includes colors 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, and 273. CI pigment blue includes blue pigments in ratios of 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, and 60. CI pigment violet (1, 19, 23, 32, 36, 38, etc.) CI pigment green includes shades 7, 36, 58, 59, 62, and 63. CI pigment brown (23, 25, etc.) CI Pigment Black 1, 7, and other black pigments.

[0164] As a coloring agent (A1), it is preferably a yellow, red, or green dye and / or pigment.

[0165] The colorant (A1) may also undergo surface treatment as needed, such as rosin treatment, surface treatment using derivatives with introduced acidic or basic groups, grafting treatment of the colorant (A1) surface using polymeric compounds, micronization treatment using sulfuric acid micronization, cleaning treatment using organic solvents or water to remove impurities, and removal treatment of ionic impurities using ion exchange. The particle size of the colorant (A1) is preferably approximately uniform.

[0166] When colorant (A) further comprises colorant (A1), the content of colorant (A1) relative to the total amount of colorant (A) is, for example, 1% by mass or more, preferably 2% by mass or more, more preferably 10% by mass or more, even more preferably 25% by mass or more, and particularly preferably 50% by mass or more. Furthermore, when colorant (A) further comprises colorant (A1), the content of colorant (A1) relative to the total amount of colorant (A) is, for example, less than 100% by mass.

[0167] When the coloring resin composition contains a solvent (E), a colorant containing liquid containing both colorant (A) and solvent (E) can be prepared in advance, and then the coloring resin composition can be prepared using this colorant containing liquid. When the colorant (A) is not soluble in solvent (E), for example, when the colorant (A) contains pigments (A1-2), the colorant containing liquid can be prepared by dispersing the colorant (A) in solvent (E) and mixing them. The colorant containing liquid may also contain part or all of the solvent (E) contained in the coloring resin composition.

[0168] Relative to the total amount of the colorant liquid, the content of solid components in the colorant liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, even more preferably 0.1% by mass or more and 99% by mass or less, even more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1% by mass or more and 50% by mass or less.

[0169] Colorant (A) can be prepared by containing a dispersant and undergoing dispersion treatment to achieve a state in which colorant (A) is uniformly dispersed in solution. When two or more colorants (A) are used in combination, they can be dispersed individually or mixed together for dispersion treatment.

[0170] Dispersants, such as surfactants, can be cationic, anionic, nonionic, or amphoteric. Specifically, examples include polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants can be used alone or in combination of two or more. Examples of dispersants by trade name include: KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-chemie Co., Ltd.), and BYK (registered trademark) (manufactured by BYK-chemie Co., Ltd.). As a dispersant, resin (B) described later can be used.

[0171] When using a dispersant, the amount of the dispersant (solid component) 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, relative to 100 parts by mass of colorant (A). If the amount of the dispersant used is within the aforementioned range, there is a tendency to obtain a colorant-containing liquid with a more uniform dispersion.

[0172] The content of colorant (A) relative to the total amount of solid components in the coloring resin composition is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass or less, and even more preferably 1% by mass or more and 30% by mass or less. If the content of colorant (A) is within the aforementioned range, the color concentration when producing a color filter is sufficient, and the composition contains the necessary amount of resin (B), thus enabling the formation of patterns with sufficient mechanical strength, which is therefore preferable. Here, the term "total amount of solid components" in this specification refers to the amount remaining after removing the solvent content from the total amount of the self-colored resin composition. The total amount of solid components and the content of each component therein can be determined, for example, using known analytical methods such as liquid chromatography or gas chromatography.

[0173] <Resin (B)> Resin (B) is not particularly limited, but it is preferably an alkali-soluble resin. Examples of resin (B) include resins [K1] to resin [K6]. Resin [K1]: A copolymer having structural units derived from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and structural units derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylene unsaturated bond; Resin [K2]: A copolymer having structural units derived from (a) and structural units derived from (b), and structural units derived from monomer (c) (which is different from (a) and (b)) (hereinafter sometimes referred to as "(c)"); Resin [K3]: A copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]: A copolymer having structural units formed by the addition of structural units derived from (a) to (b) and structural units derived from (c); Resin [K5]: A copolymer having a structural unit formed by adding (a) to a structural unit derived from (b) and a structural unit derived from (c); Resin [K6]: A copolymer having structural units formed by adding (a) to structural units derived from (b) and further adding to carboxylic anhydrides, and structural units derived from (c).

[0174] Examples of monocarboxylic acids (a) include: acrylic acid, methacrylic acid, butenoic acid, and unsaturated monocarboxylic acids such as o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid; Maleic acid, fumaric acid, citraconic acid, zeaxanthin, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexene dicarboxylic acid are all unsaturated dicarboxylic acids. Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, etc., are bicyclic unsaturated compounds containing carboxyl groups; Carboxylic anhydrides, excluding fumaric acid and medoconic acid, are the anhydrides of the aforementioned unsaturated dicarboxylic acids; Unsaturated mono[(meth)acrylic acid oxyethyl] esters of di- or higher polycarboxylic acids, such as succinate mono[2-(meth)acrylic acid oxyethyl] ester and phthalate mono[2-(meth)acrylic acid oxyethyl] ester; Unsaturated acrylates, such as α-(hydroxymethyl)acrylates, contain both hydroxyl and carboxyl groups in the same molecule. Of these, acrylic acid, methacrylic acid, and maleic anhydride are preferred in terms of copolymerization reactivity or the solubility of the obtained resin in alkaline aqueous solutions. Furthermore, in this specification, the term "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acrylyl" and "(meth)acrylate" have the same meaning.

[0175] Monomer (b) refers to a polymeric compound having a cyclic ether structure having 2 to 4 carbon atoms (e.g., selected from at least one of the group consisting of oxecyclopropane ring, oxecyclobutane ring, and tetrahydrofuran ring (oxecyclopentane ring)) and an vinyl unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acrylic acid oxy group.

[0176] Examples of monomers (b) include monomers having an oxopropyl group and an ethylene unsaturated bond (hereinafter, sometimes referred to as "monomer (b1)"), monomers having an oxobutyl group and an ethylene unsaturated bond (hereinafter, sometimes referred to as "monomer (b2)"), and monomers having a tetrahydrofuran group and an ethylene unsaturated bond (hereinafter, sometimes referred to as "monomer (b3)").

[0177] As a monomer (b1), examples include monomers having a structure formed by epoxidation of unsaturated aliphatic hydrocarbons (hereinafter, sometimes referred to as "monomer (b1-1)") and monomers having a structure formed by epoxidation of unsaturated alicyclic hydrocarbons (hereinafter, sometimes referred to as "monomer (b1-2)").

[0178] As a monolith (b1-1), it is preferably a monolith having a glycidyl group and an ethylene unsaturated bond. Specifically, examples of monoliths (b1-1) include: glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (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(glycidyloxy) Methyl styrene, 2,4-bis(glycidoxymethyl)styrene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tris(glycidoxymethyl)styrene, 2,3,5-tris(glycidoxymethyl)styrene, 2,3,6-tris(glycidoxymethyl)styrene, 3,4,5-tris(glycidoxymethyl)styrene, 2,4,6-tris(glycidoxymethyl)styrene, etc.

[0179] Examples of monodimers (b1-2) include: vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel), 3,4-epoxycyclohexylmethyl methacrylate (e.g., Cyclomer A400; manufactured by Daicel), 3,4-epoxycyclohexylmethyl methacrylate (e.g., Cyclomer M100; manufactured by Daicel), compounds represented by formula (BI), and compounds represented by formula (BII).

[0180] [Chemistry 38]

[0181] In formulas (BI) and (BII), Ra and Rb independently represent hydrogen atoms or alkyl groups having 1 to 4 carbon atoms, wherein the hydrogen atoms in the alkyl group may be substituted with hydroxyl groups; Xa and Xb independently represent single bonds, *-Rc-, *-RcO-, *-RcS-, or *-Rc-NH-; Rc represents an alkyldiyl group with 1 to 6 carbon atoms; * indicates a bond with O]

[0182] Examples of alkyl groups having 1 to 4 carbon atoms include: methyl, ethyl, n-propyl, isopropyl, n-butyl, dibutyl, tributyl, etc.

[0183] Examples of alkyl groups that are hydrogen atoms substituted with hydroxyl groups include: hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc.

[0184] Ra and Rb are preferably represented by hydrogen atoms, methyl groups, hydroxymethyl groups, 1-hydroxyethyl groups, and 2-hydroxyethyl groups, and more preferably by hydrogen atoms and methyl groups.

[0185] Examples of alkyldiyl groups include: methylene, ethyl, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, etc.

[0186] Xa and Xb are preferably listed as single bonds, methylene, ethyl groups, *-CH 2-O- (* indicates a bond with O) groups, and *-CH 2CH 2-O- groups, and more preferably listed as single bonds and *-CH 2CH 2-O- groups (* indicates a bond with O).

[0187] 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 even more preferred.

[0188] [Chemistry 39]

[0189] As the compound represented by formula (BII), compounds represented by any one of formulas (BII-1) to (BII-15) can be listed, among which compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9) and (BII-11) to (BII-15) are preferred, and compounds represented by formulas (BII-1), (BII-7), (BII-9) and (BII-15) are even more preferred.

[0190] [Chemistry 40]

[0191] The compounds represented by formula (BI) and formula (BII) may be used individually or in combination. When used in combination, the content ratio of the compounds represented by formula (BI) and formula (BII), based on moles, is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

[0192] The monomer (b2) having an oxetyl group and an vinyl unsaturated bond is preferably a monomer having an oxetyl group and a (meth)propenyloxy group. Examples of monomers (b2) include 3-methyl-3-(meth)propenyloxymethyloxetane, 3-ethyl-3-(meth)propenyloxymethyloxetane, 3-methyl-3-(meth)propenyloxyethyloxetane, and 3-ethyl-3-(meth)propenyloxyethyloxetane.

[0193] As a monomer (b3) having a tetrahydrofuran group and an ethylene unsaturated bond, it is more preferably a monomer having a tetrahydrofuran group and a (meth)acrylic acid oxy group. Examples of monomers (b3) include tetrahydrofurfuryl acrylate (e.g., Biscoat V#150, manufactured by Osaka Organic Chemicals Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0194] Examples of monomethyl methacrylate (c) include: methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, dibutyl methacrylate, tributyl methacrylate, 2-ethylhexyl methacrylate, dodecyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclopentyl methacrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, tricyclo[5.2.1.0 2,6]decane-8-yl ester (commonly referred to as "dicyclopentyl methacrylate" in this technical field; sometimes also called "tricyclodecyl methacrylate"), tricyclo[5.2.1.0 2,6]decane-9-yl ester, tricyclo[5.2.1.0 2,6]decane-9-yl ester, and tricyclo[5.2.1.0 2,6]decane-8-yl ester. [2,6]decen-8-yl ester (commonly referred to as "(meth)acrylate dicyclopentenyl ester"), tricyclo[5.2.1.0 2,6]decen-9-yl ester, dicyclopentyloxyethyl ester, isobornyl ester, adamantyl ester, allyl ester, propargyl ester, phenyl ester, naphthyl ester, and benzyl ester, etc. (meth)acrylates; Hydroxyl acrylates such as 2-hydroxyethyl acrylate and 2-hydroxypropyl acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo [2.2.1]Hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene, etc., are bicyclic unsaturated compounds; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimido-3-maleimide benzoate, N-succinimido-4-maleimide butyrate, N-succinimido-6-maleimide hexanoate, N-succinimido-3-maleimide propionate, and N-(9-acridyl)maleimide, etc., are dicarbonyl nimidide derivatives. Aromatic compounds containing vinyl groups, such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl nitrile compounds containing vinyl groups, such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl amides containing vinyl groups, such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Of these, in terms of copolymerization reactivity and heat resistance, it is preferred to use at least one of the group consisting of styrene, vinyltoluene, tricyclo[5.2.1.0 2,6]decane-8-yl ester, tricyclo[5.2.1.0 2,6]decane-9-yl ester, tricyclo[5.2.1.0 2,6]decen-8-yl ester, tricyclo[5.2.1.0 2,6]decen-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, 2-hydroxyethyl ester of (meth)acrylate, and benzyl ester of (meth)acrylate.

[0195] Of all the structural units constituting resin [K1], the ratio of structural units originating from each individual unit in resin [K1] is preferably [missing information]. Structural units derived from (a): 2 mol% ~ 60 mol% Structural units derived from (b): 40 mol% ~ 98 mol% Better Structural units derived from (a): 10 mol% ~ 50 mol% Structural units derived from (b): 50 mol%~90 mol%. If the ratio of the structural units of the resin [K1] is within the range described, there is a tendency for the coloring resin composition to have excellent storage stability, developability when forming colored patterns, and solvent resistance of the obtained color filter.

[0196] The resin [K1] can be manufactured, for example, by referring to the method described in the literature "Experimental Method for Polymer Synthesis" (written by Takayuki Otsu, Chemical Dojin Publishing Co., 1st edition, 1st printing, published on March 1, 1972) and the references cited in that literature.

[0197] Specifically, examples include placing the specified amounts of (a) and (b), the polymerization initiator, and the solvent into a reaction vessel, for example, by replacing the oxygen with nitrogen to create a deoxygenated environment, and then heating and maintaining the temperature while stirring. Furthermore, the polymerization initiator and solvent used herein are not particularly limited, and those commonly used in the field can be used. For example, as polymerization initiators, examples include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylpentanonitrile) etc.) or organic peroxides (benzoyl peroxide, etc.), and as solvents, any solvent capable of dissolving the monomers is acceptable; examples include solvents (E) used in the coloring resin composition of this invention, and solvents described later.

[0198] Furthermore, the obtained copolymer can be used directly from the reaction solution, or from a concentrated or diluted solution, or extracted in solid (powder) form using methods such as reprecipitation. In particular, by using the solvent contained in the coloring resin composition of the present invention as the solvent during polymerization, the reaction solution can be directly used in the preparation of the coloring resin composition of the present invention, thus simplifying the manufacturing steps of the coloring resin composition of the present invention.

[0199] Of all the structural units constituting resin [K2], the ratio of structural units originating from each individual unit in resin [K2] is preferably [missing information]. Structural units derived from (a): 2 mol% ~ 45 mol% Structural units derived from (b): 2 mol% ~ 95 mol% Structural units derived from (c): 1 mol% ~ 65 mol% Better Structural units derived from (a): 5 mol% ~ 40 mol% Structural units derived from (b): 5 mol% ~ 80 mol% Structural units derived from (c): 5 mol%~60 mol%. If the ratio of the structural units of resin [K2] is within the range described, there is a tendency for the coloring resin composition to have excellent storage stability, developability when forming colored patterns, and solvent resistance, heat resistance and mechanical strength of the obtained color filter.

[0200] Resin [K2] can be manufactured, for example, in the same manner as the method described as the manufacturing method of resin [K1].

[0201] Of all the structural units constituting resin [K3], the ratio of structural units originating from each individual unit in resin [K3] is preferably [missing information]. Structural units derived from (a): 2 mol% ~ 60 mol% Structural units derived from (c): 40 mol%~98 mol% Better Structural units derived from (a): 10 mol% ~ 50 mol% Structural units derived from (c): 50 mol%~90 mol%. Resin [K3] can be manufactured, for example, in the same manner as the method described as the manufacturing method of resin [K1].

[0202] The resin [K4] can be manufactured by obtaining a copolymer of (a) and (c) by adding a cyclic ether having 2 to 4 carbons in (b) to a carboxylic acid and / or carboxylic anhydride in (a). First, the copolymer of (a) and (c) is manufactured in the same manner as that described in the manufacturing method of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as the ratio listed in resin [K3].

[0203] Next, the cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a portion of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer. Following the production of the copolymer of (a) and (c), the environment inside the flask is replaced with air instead of nitrogen. (b), a reaction catalyst for carboxylic acid or carboxylic anhydride with cyclic ether (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone) are placed inside the flask and reacted, for example, at 60°C to 130°C for 1 to 10 hours, thereby producing resin [K4]. Compared to (a) 100 mol, the amount of (b) used is preferably 5 mol to 80 mol, more preferably 10 mol to 75 mol. By setting it within this range, there is a tendency for a good balance of the storage stability of the colored resin composition, the developability when forming a pattern, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern. In terms of the high reactivity of cyclic ethers and the difficulty in leaving unreacted (b), (b) used as resin [K4] is preferably (b1), and more preferably (b1-1). The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to the total amount of 100 parts by mass of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to the total amount of 100 parts by mass of (a), (b), and (c). The charging method, reaction temperature, and time, among other reaction conditions, can be appropriately adjusted taking into account factors such as the manufacturing equipment or the heat generated during polymerization. Furthermore, similarly to polymerization conditions, the charging method or reaction temperature can be appropriately adjusted taking into account factors such as the manufacturing equipment or the heat generated during polymerization.

[0204] Regarding resin [K5], as a first stage, copolymers of (b) and (c) are obtained in the same manner as resin [K1]. Similarly, the obtained copolymer can be used directly from the reaction solution, or from a concentrated or diluted solution, or extracted in solid (powder) form using methods such as reprecipitation. The ratios of structural units originating from (b) and (c) are preferably respectively, relative to the total number of moles of all structural units constituting the copolymer. Structural units derived from (b): 5 mol% ~ 95 mol% Structural units derived from (c): 5 mol%~95 mol% Better Structural units derived from (b): 10 mol% ~ 90 mol% Structural units derived from (c): 10 mol%~90 mol%.

[0205] Furthermore, under the same conditions as the manufacturing method of resin [K4], the carboxylic acid or carboxylic anhydride contained in (a) and the cyclic ether derived from (b) in the copolymer of (b) and (c) are reacted to obtain resin [K5]. The amount of (a) reacting with the copolymer is preferably 5 to 80 mol relative to (b) 100 mol. In terms of the high reactivity of cyclic ethers and the difficulty in leaving unreacted (b), (b) used as resin [K5] is preferably (b1), and more preferably (b1-1).

[0206] Resin [K6] is a resin obtained by further reacting carboxylic anhydride with resin [K5]. The carboxylic anhydride is reacted with a hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic anhydride. Examples of carboxylic anhydrides include: maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxylic bicyclic [2.2.1]hept-2-ene anhydride. The preferred amount of carboxylic anhydride used is 0.5 mol to 1 mol relative to 1 mol used in (a).

[0207] Specific examples of resins (B) include: methyl 3,4-epoxycyclohexyl methacrylate / (meth)acrylate copolymer, decyl 3,4-epoxytricyclo[5.2.1.0 2,6]acrylate / (meth)acrylate copolymer, etc. [K1]; glycidyl methacrylate / benzyl methacrylate / (meth)acrylate copolymer, glycidyl methacrylate / styrene / (meth)acrylate copolymer, decyl 3,4-epoxytricyclo[5.2.1.0 2,6]acrylate / (meth)acrylate / N-cyclohexylmaleimide copolymer, decyl 3,4-epoxytricyclo[5.2.1.0 2,6]acrylate / (meth)acrylate / N-cyclohexylmaleimide copolymer, etc. [2,6] Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid 2-hydroxyethyl ester copolymer, 3-methyl-3-(meth)acrylic acid oxymethyloxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins obtained by adding glycidyl methacrylate to benzyl acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl methacrylate to tricyclodecyl acrylate / styrene / (meth)acrylic acid copolymer, and resins obtained by adding glycidyl methacrylate to tricyclodecyl acrylate / styrene / (meth)acrylic acid copolymer. Resins such as those obtained by adding glycidyl methacrylate to a copolymer of tricyclodecyl methacrylate / benzyl methacrylate / methacrylic acid [K4]; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl methacrylate / glycidyl methacrylate; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl methacrylate / styrene / glycidyl methacrylate [K5]; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl methacrylate / glycidyl methacrylate and then reacting it with tetrahydrophthalic anhydride [K6], etc.

[0208] Resin (B) is preferably selected from at least one of the group consisting of resin [K1] and resin [K2], and particularly preferably resin [K2].

[0209] The weight-average molecular weight (Mw) of the polystyrene-converted resin (B) 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. If the weight-average molecular weight is within the aforementioned range, there is a tendency for the unexposed portion to have high solubility in the developer, and the resulting pattern to have a high residual film rate or high hardness. The dispersion of resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] 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.

[0210] The acid value (converted to solids content) of resin (B) is preferably 10 mg-KOH / g or higher and 300 mg-KOH / g or lower, more preferably 20 mg-KOH / g or higher and 250 mg-KOH / g or lower, even more preferably 25 mg-KOH / g or higher and 200 mg-KOH / g or lower, even more preferably 30 mg-KOH / g or higher and 150 mg-KOH / g or lower, and particularly preferably 60 mg-KOH / g or higher and 135 mg-KOH / g or lower. Here, the acid value is a value determined as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin, and can be obtained, for example, by titration using an aqueous solution of potassium hydroxide.

[0211] In the solid component of the coloring resin composition, the content of resin (B) is preferably 5% to 50% by mass, more preferably 10% to 40% by mass, and even more preferably 15% to 30% by mass. If the content of resin (B) is within the above range, there is a tendency for the unexposed portion to have high solubility in the developer.

[0212] <Polymerizing Compounds (C)> The polymerizable compound (C) is a compound that can be polymerized by active free radicals and / or acids generated by the self-polymerization initiator (D), such as polymerizable compounds with ethylene unsaturated bonds, preferably (meth)acrylate compounds.

[0213] Examples of polymeric compounds having an ethylene unsaturated bond include: nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc., as well as the said monomers (a), (b), and (c).

[0214] Examples of polymeric compounds having two vinyl 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-methylpentyl glycol di(meth)acrylate.

[0215] The polymerizable compound (C) is preferably a polymerizable compound having three or more vinyl unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, and tris(2-(meth)acryloxyethyl)isocyanuric acid. Ester, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate and caprolactone-modified dipentaerythritol hexa(meth)acrylate, etc., preferably at least one selected from the group consisting of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0216] The weight average molecular weight of the polymeric 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.

[0217] The content of polymeric compound (C) relative to the total amount of solid components in the coloring resin composition may be, for example, 1% or more by mass and 99% or less by mass, preferably 5% or more by mass and 90% or less by mass, more preferably 10% or more by mass and 80% or less by mass, and even more preferably 12% or more by mass and 70% or less by mass.

[0218] <Polymerization Initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active free radicals, acids, etc. through the action of light or heat to initiate polymerization, and well-known polymerization initiators can be used.

[0219] Examples of polymerization initiators (D) include: O-acetylgoxime compounds, benzyl ketone compounds, biimidazole compounds, triazine compounds, and acetylgphosphine oxide compounds.

[0220] Examples of O-acetylated oxime compounds include: N-benzoyloxy-1-(4-phenylmercaptophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylmercaptophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetylated 1-(4-phenylmercaptophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetylated 1-(4-phenylmercaptophenyl)-3-cyclohexylpropane-1-one-2-imine, and N-acetylated 1-[9-ethyl-6-] (2-Methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentylmethyloxy)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, etc. In addition, commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (manufactured by BASF), N-1919 (manufactured by ADEKA), and TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) can also be used as O-acyloxime compounds. Among these, N-benzoyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylmercaptophenyl)-3-cyclopentylpropan-1-one-2-imine, and TR-PBG327 (N-acetylated-1-oxime- At least one of the group consisting of 1-(4-phenylmercaptophenyl)-3-cyclohexylpropane-1-one-2-imine, more preferably at least one of the group consisting of N-benzoyloxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine and TR-PBG327 (N-acetoxy-1-(4-phenylmercaptophenyl)-3-cyclohexylpropane-1-one-2-imine).

[0221] Examples of benzyl ketone compounds include: 2-methyl-2-morpholino-1-(4-methylmercaptophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one. Commercially available products such as Irgacure (registered trademark) 369, 907, and 379 (manufactured by BASF) can also be used as benzyl ketone compounds. Examples of benzyl ketone compounds include: 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.

[0222] Examples of biimidazole compounds include: 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (e.g., see Japanese Patent Publication No. 6-75372, Japanese Patent Publication No. 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(alkoxyphenyl)biimidazole, etc. Bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (e.g., see Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. 62-174204, etc.) and biimidazole compounds with alkoxycarbonyl substitution of the 4,4',5,5'-phenyl group (e.g., see Japanese Patent Publication No. 7-10913, etc.).

[0223] Examples of triazine compounds include: 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2] [-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0224] Examples of phosphine oxide compounds include 2,4,6-trimethylbenzyldiphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can also be used.

[0225] Furthermore, examples of polymerization initiators (D) include: benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and other benzoin compounds; benzophenone compounds such as methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthroquinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzoin, methyl phenylglyoxylate, and titanium decene compounds. These are preferably used in combination with polymerization initiators (D1) (especially amine compounds) described later.

[0226] The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of benzyl ketone compounds, triazine compounds, acetylsphine oxide compounds, O-acetylgoxime compounds and bimidazole compounds, and more preferably a polymerization initiator comprising an O-acetylgoxime compound.

[0227] Relative to 100 parts by mass of the combined amount of resin (B) and polymerizable compound (C) in the coloring resin composition, the content of polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less. If the content of polymerization initiator (D) is within the aforementioned range, there is a tendency to increase sensitivity and shorten exposure time, thereby improving the productivity of color filters.

[0228] <Polymerization Initiator (D1)> The coloring resin composition of the present invention may also include a polymerization initiator (D1). The polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound (C) that is initiated by a polymerization initiator (D). When a polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

[0229] Examples of polymerization initiators (D1) include: amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0230] Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, ethyl 2-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being a preferred example. Additionally, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used as amine compounds.

[0231] Examples of alkoxyanthracene compounds include: 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0232] Examples of thioxanthone compounds include: 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0233] Examples of carboxylic acid compounds include: phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid, etc.

[0234] When using these polymerization initiators (D1), the content of the D1 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, relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C) contained in the coloring resin composition.

[0235] Solvent (E) The solvent (E) is not particularly limited and may be any solvent commonly used in this field. Solvents (E) can be exemplified by: ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether-ester solvents (solvents containing both -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. Two or more of these solvents may also be used in combination.

[0236] Examples of ester solvents include: methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone, etc.

[0237] 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, phenethyl ether, and methyl anisole, etc.

[0238] Examples of ether ester solvents include: methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutylacetate, 3-methyl-3-methoxybutylacetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate, etc.

[0239] 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.

[0240] Examples of alcohol solvents include: methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol.

[0241] Examples of aromatic hydrocarbon solvents include: benzene, toluene, xylene, and mesitylene.

[0242] Examples of acetamide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0243] The solvent (E) is preferably a solvent containing at least one selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol and cyclohexanone.

[0244] The solvent (E) content relative to the total amount of the coloring resin composition is typically 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 95% by mass or less, further preferably 70% by mass or more and 95% by mass or less, and further preferably 75% by mass or more and 90% by mass or less. In other words, the total amount of solid components in the coloring resin composition is typically 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 50% by mass or less, further preferably 5% by mass or more and 30% by mass or less, and further preferably 10% by mass or more and 25% by mass or less. If the solvent (E) content is within the aforementioned range, the flatness during coating becomes good, and the color concentration is not insufficient when forming a color filter, thus tending to improve display properties.

[0245] <Leveling agent (F)> Examples of leveling agents (F) include silicone-based surfactants, fluorinated surfactants, and silicone-based surfactants containing fluorine atoms. These may also have polymerizable groups on their side chains.

[0246] As silicone-based surfactants, examples include surfactants with intramolecular siloxane bonds. Specifically, examples include: Toray silicone DC3PA, Toray silicone SH7PA, Toray silicone DC11PA, Toray silicone SH21PA, Toray silicone SH28PA, Toray silicone SH29PA, Toray silicone SH30PA, and Toray silicone SH8400 (trade name: Toray Dow Corning). Products manufactured by Corning (stock), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Industry (stock), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan Co., Ltd.), etc.

[0247] Fluorinated surfactants include those with intramolecular fluorocarbon chains. Specifically, examples include: Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M), Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, and Megafac... RS-718-K (manufactured by DIC), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Electronics & Chemicals), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by AGC), and E5844 (manufactured by Daikin Fine Chemicals Research Institute), etc.

[0248] As silicone-based surfactants containing fluorine atoms, examples include surfactants with intramolecular siloxane bonds and fluorocarbon chains. Specifically, examples include: Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, and Megafac F443 (manufactured by DIC).

[0249] When a leveling agent (F) is present, the content of the leveling agent (F) relative to the total amount of the coloring resin composition is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and even more preferably 0.0005% by mass or more and 0.1% by mass or less. Furthermore, this content does not include the content of the dispersant. If the content of the leveling agent (F) is within the aforementioned range, the flatness of the color filter can be good.

[0250] <Other Ingredients> The coloring resin composition may also include fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, and other additives known in the art, as needed.

[0251] <Manufacturing Method of Coloring Resin Composition> The colored resin composition can be prepared by mixing a colorant (A), a resin (B), and, as needed, 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 carried out using known or conventional apparatus or conditions. The colorant (A) can be used in the form of a colorant liquid, which is obtained by pre-mixing with a portion or all of the solvent (E) and dispersing it using a bead mill or the like until the average particle size is about 0.2 μm or less. It is preferred to use it in the form of a colorant liquid. At this time, a portion or all of the dispersant and resin (B) can also be added as needed. Alternatively, the colorant (A) can also be used in the form of a colorant liquid obtained by pre-dissolving a portion or all of the solvent (E). The remaining components are mixed into the colorant liquid thus obtained at a predetermined concentration, thereby preparing the target colored resin composition.

[0252] <Manufacturing Method of Color Filters> A color filter that can serve as a color conversion layer can be formed from the coloring resin composition of the present invention. Methods for forming the color pattern include photolithography, inkjet printing, and printing. Photolithography is preferred. Photolithography involves coating the coloring resin composition onto a substrate, drying it to form a coloring resin composition layer, and then exposing and developing the coloring resin composition layer through a photomask. In photolithography, by not using a photomask and / or not developing during exposure, a color coating film, which is a hardened form of the coloring resin composition layer, can be formed. The color pattern or color coating film thus formed is the color filter of the present invention.

[0253] The thickness of the produced color filter is not particularly limited and can be adjusted appropriately according to the purpose or application. For example, it is 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, even 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.

[0254] As a substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda-lime glass with a silicon dioxide coating can be used; or resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and aluminum, silver, or silver / copper / palladium alloy thin films can be formed on the substrate. Other color filter layers, resin layers, transistors, circuits, etc., can also be formed on these substrates.

[0255] The creation of individual color pixels using photolithography can be performed under known or conventional equipment or conditions. For example, it can be done in the following manner. First, the coloring resin composition is coated onto the substrate and dried by removing volatile components such as solvents through heating and drying (pre-baking) and / or vacuum drying to obtain a smooth colored resin composition layer. Examples of coating methods include: spin coating, slot coating, and a combination of slot and spin coating. The temperature for heating and drying is preferably 30°C or higher and 120°C or lower, more preferably 50°C or higher and 110°C or lower. The heating time is preferably 10 seconds or higher and 60 minutes or lower, more preferably 30 seconds or higher and 30 minutes or lower. When performing vacuum drying, it is preferable to carry out the process at a pressure of 50 Pa or more and 150 Pa or less, and at a temperature of 20°C or more and 25°C or less. There is no particular limitation on the film thickness of the coloring resin composition layer; it can be appropriately selected according to the film thickness of the target color filter.

[0256] Secondly, the colored resin composition layer can be exposed through a photomask used to form the target colored pattern. The pattern on the photomask is not particularly limited; a pattern appropriate to the target application can be used. Furthermore, in order to uniformly irradiate the entire exposed surface with parallel light or to accurately align the photomask with the substrate on which the colored resin composition layer is formed, it is preferable to use exposure equipment such as a mask aligner and a stepper. When forming a colored coating, exposure can be performed without using a photomask.

[0257] The light source used in the exposure is preferably a light source that produces light with wavelengths greater than 250 nm and less than 450 nm. For example, a filter that cuts off the wavelength range can be used to cut off light less than 350 nm, or a bandpass filter that selectively extracts light near 436 nm, 408 nm, and 365 nm can be used to selectively extract light. Specifically, examples include mercury lamps, light-emitting diodes (LEDs), metal halide lamps, and halogen lamps.

[0258] A colored pattern is formed on a substrate by contacting the exposed colored resin composition layer with a developing solution for development. During development, the unexposed portions of the colored resin composition layer dissolve in the developing solution and are removed. The developing solution is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developing solution may also contain a surfactant. The development method can be any of the following: liquid coating, immersion, or spraying. Furthermore, the substrate can be tilted at any angle during development. It is best to wash the substrate after development with water.

[0259] Furthermore, it is preferable to perform a post-baking process on the obtained colored pattern or colored coating. The post-baking temperature is preferably 150°C or higher and 250°C or lower, more preferably 160°C or higher and 240°C or lower. The post-baking time is preferably 1 minute or higher and 120 minutes or lower, more preferably 10 minutes or higher and 60 minutes or lower.

[0260] <Display Device> The color filter is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic electroluminescence (EL) devices, electronic paper, etc.) and solid-state imaging elements.

[0261] This application claims the benefit of priority based on Japanese Patent Application No. 2021-078790, filed on May 6, 2021. The entire contents of the description of Japanese Patent Application No. 2021-078790, filed on May 6, 2021, are incorporated herein by reference. [Example]

[0262] Secondly, examples of synthesis are provided to illustrate the invention more specifically. In these examples, unless otherwise specified, the percentage or parts of content or usage are indicated by mass.

[0263] In the following synthesis examples, the structures of the compounds were confirmed by mass analysis (LC: Agilent 1200 type, MASS: Agilent LC / MSD6130 type).

[0264] <Pigment Synthesis> [Example 1 of pigment synthesis: Synthesis of compound (BI-1)] The following reaction was carried out under nitrogen atmosphere. 0.48 parts palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.74 parts 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 7.50 parts sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 14.58 parts 1-bromonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to a flask including a cooling tube and a stirrer. Then, a mixed solution of 9 parts 4,4'-methylenebis(2,6-dimethylaniline) (manufactured by Sigma-Aldrich) and 63 parts toluene was added dropwise to the flask. The reaction mixture was heated to 110°C in an oil bath and stirred for 2 hours. The reaction mixture was allowed to cool and then filtered through diatomaceous earth to obtain the filtrate. 180 parts ethyl acetate and 180 parts deionized water were added to the filtrate and mixed vigorously. The mixture was then separated to obtain the organic layer. The obtained organic layer was dried using 48 parts of sodium sulfate, and the solid was separated and removed by filtration. The obtained organic layer was concentrated to obtain a crude product. The crude product was purified by silicone column chromatography (solvent: chloroform / methanol 100 / 1~20 / 1), and the obtained 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).

[0265] [Chemistry 41]

[0266] Identification of compounds represented by formula (BI-1) (Mass Analysis) Ionization Mode = ESI+: m / z = 506.5

[0267] [Example 2 of pigment synthesis: Synthesis of compound (BI-2)] 5.11 parts of 4,4'-methylenebis(o-toluidine), 9.38 parts of 1-bromonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.28 parts of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.12 parts of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.76 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 63 parts of toluene were mixed and stirred at 110°C for 1 hour. After cooling to 25°C, the resulting mixture was filtered through diatomaceous earth, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, resulting in 9.10 parts (84% yield) of the compound represented by formula (BI-2).

[0268] [Chemistry 42]

[0269] Identification of compounds represented by formula (BI-2) (Mass Analysis) Ionization Mode = ESI+: m / z = [M+H] + 479.4

[0270] [Example 3 of pigment synthesis: Synthesis of compound (BI-3)] Under ice-water bath cooling, 10.4 parts of the compound represented by formula (BI-2) and 4.8 parts of dimethyl sulfoxide were added to 8.32 parts of sodium tributoxide, followed by 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 obtained mixture to form a suspension, which was then filtered. The crude compound was purified by silicone column chromatography (developing 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%).

[0271] [Chemistry 43]

[0272] Identification of compound (BI-3) (Mass Analysis) Ionization Mode = ESI+: m / z = [M+H] + 535.5

[0273] [Example 4 of pigment synthesis: Synthesis of compound (BI-4)] 20 parts of 3-chloro-2,6-dimethylaniline, 300 parts of deionized water, and 1.9 parts of polyoxymethylene were mixed and stirred at 100°C for 3 hours. After cooling to 0°C, 500 parts of cold 4% sodium hydroxide aqueous solution were added to the obtained reaction solution to form a suspension, which was then filtered. The obtained solid was dried under reduced pressure at 60°C to obtain 22 parts of the compound represented by formula (BI-4a).

[0274] [Chemistry 44]

[0275] The following reaction was carried out under nitrogen atmosphere. 1.1 parts of bis(dibenzylacetone)palladium(O), 1.2 parts of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 17.8 parts of sodium tributoxide, and 20 parts of the compound represented by formula (BI-4a) were added to a flask including a cooling tube and a stirrer. 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. The reaction mixture was cooled in an ice bath, then diluted with 500 parts of ethyl acetate, injected into 500 parts of 1.5 N hydrochloric acid, stirred, and separated to obtain an organic layer. The obtained organic layer was concentrated to obtain 51 parts of crude material. The compound was purified by silicone column chromatography (solvent: petroleum ether / ethyl acetate 100 / 3), and 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).

[0276] [Chemistry 45]

[0277] [Example 5 of pigment synthesis: Synthesis of compound (BI-5)] 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 1500 parts of ethyl acetate, added to 500 parts of a 10% sodium bicarbonate aqueous solution, and stirred. The mixture was separated to obtain an organic layer. The obtained organic layer was concentrated to obtain 89 parts of crude product. It was purified by silicone column chromatography (solvent: petroleum ether / ethyl acetate 100 / 0→70 / 30), and 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).

[0278] [Chemistry 46]

[0279] 72 parts of the compound represented by formula (BI-5a), 4.5 parts of copper bromide (I), 202.9 parts of a 25% sodium methoxide methanol solution, 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 crude product were purified by silicone column chromatography (solvent: petroleum ether / ethyl acetate 100 / 0→80 / 20), and the 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).

[0280] [Chemistry 47]

[0281] 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 amount added in 10 batches) were mixed and stirred at 25°C for 16 hours. The mixture was diluted with 500 parts of ethyl acetate and filtered through diatomaceous earth. The filtrate was concentrated to obtain a crude product. 500 parts of ethyl acetate and 500 parts of deionized water were added to the crude product, and the mixture was separated. The resulting organic layer was concentrated. 42 parts of the crude product were purified using silicone column chromatography (solvent: petroleum ether / ethyl acetate 100 / 0→90 / 10), and the 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).

[0282] [Chemistry 48]

[0283] Except for using the compound represented by formula (BI-5c) instead of 3-chloro-2,6-dimethylaniline, the same operation as in pigment synthesis example 4 was performed to obtain the compound represented by formula (BI-5).

[0284] [Chemistry 49]

[0285] [Example 6 of pigment synthesis: Synthesis of compound (CI-1)] The following reaction was carried out under nitrogen atmosphere. 0.27 parts of bis(benzylacetone)palladium(0) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.57 parts of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (manufactured by Sigma-Aldrich), 42.1 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 50 parts of 4,4'-dichlorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise to a flask including a cooling tube and a stirrer. Then, a mixed solution of 48.3 parts of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 432 parts of toluene was added dropwise to the flask. The reaction mixture was heated to 80°C in an oil bath and stirred for 2 hours. The reaction mixture was cooled in an ice bath and then filtered to obtain a solid and a filtrate. The solid is designated as Bold A1, and the filtrate as Filtrate A1. The obtained crude substance A1 was washed with 50 parts toluene, followed by two washes with 250 parts of deionized water to obtain a solid. This solid was designated as crude substance B1. Filtrate A1, 50 parts toluene, 229 parts deionized water, and 20.8 parts 35% hydrochloric acid were added to a flask equipped with a bottom drain. The mixture was stirred for 1 hour, and then 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, then dried with 150 parts magnesium sulfate, and the solid was filtered off. The obtained organic layer was concentrated to obtain a solid. This solid was designated as crude substance C1. Crude substance B1 and crude substance C1 were added to a flask equipped with a stirrer, along with acetonitrile at a mass equal to four times the total mass of crude substance B1 and crude substance C1. The mixture was stirred for 1 hour. The mixture was filtered, and the obtained solid was washed with acetonitrile at a mass equal to one times the total mass of crude substance B1 and crude substance C1. The cleaned solid was dried under reduced pressure at 60°C to obtain 75.9 parts of the compound represented by formula (CI-1). The yield was 90.6%.

[0286] [Transformation 50]

[0287] [Example 7 of pigment synthesis: Synthesis of compound (CI-2)] The following reaction was carried out under nitrogen atmosphere. 50 parts of the compound represented by formula (CI-1) and 188 parts of N,N-dimethylformamide were added to a flask including a cooling tube and a stirrer, and the mixture was stirred for 30 minutes while being cooled in an ice bath. 40 parts of potassium terbutoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the same flask, and the mixture was stirred for another hour while being cooled in an ice bath. 55.6 parts of iodoethane (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise while the reaction mixture was cooled in an ice bath. The reaction mixture was heated to 35°C using an oil bath and stirred for 5 hours, then allowed to cool to room temperature. 1000 parts of a 10% sodium chloride aqueous solution were added to another flask including a stirrer, and the reaction mixture was added dropwise while stirring. The mixture was stirred for 30 minutes, then filtered to obtain a solid. The obtained solid was washed three times with 500 parts of deionized water and dried under reduced pressure at 60°C to obtain 53.0 parts of the compound represented by formula (CI-2). The yield was 93.5%.

[0288] [Chemistry 51]

[0289] [Example 8 of pigment synthesis: Synthesis of compound (CI-3)] Except for using 2,4,6-trimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), the compound represented by formula (CI-3) was obtained in the same manner as in pigment synthesis example 6.

[0290] [Chemistry 52]

[0291] [Example 9 of pigment synthesis: Synthesis of compound (CI-4)] Except for using the compound represented by formula (CI-3) instead of the compound represented by formula (CI-1), the compound represented by formula (CI-4) was obtained in the same manner as in pigment synthesis example 7.

[0292] [Chemistry 53]

[0293] [Example 10 of pigment synthesis: Synthesis of compound (CI-5)] Except for using 2,6-dimethyl-4-methoxyaniline instead of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), the compound represented by formula (CI-5) was obtained in the same manner as in pigment synthesis example 6.

[0294] [Chemistry 54]

[0295] [Example 11 of pigment synthesis: Synthesis of compound (CI-6)] Except for using the compound represented by formula (CI-5) instead of the compound represented by formula (CI-1), the compound represented by formula (CI-6) was obtained in the same manner as in pigment synthesis example 7.

[0296] [Chemistry 55]

[0297] [Example 12 of pigment synthesis: Synthesis of compound (I-5a-1)] The following reaction was carried out under nitrogen atmosphere. One 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 to a flask including a cooling tube and a stirrer. Then, 5.4 parts of phosphorus oxychloride (manufactured by Fujifilm and Koei Tecmo Chemical Co., Ltd.) were added, and the mixture was stirred at 110°C for 7 hours and 30 minutes. The reaction mixture was then cooled to room temperature, and 450 parts of ethyl acetate and saturated brine were added. The mixture was filtered to obtain a crude product. It was purified by silicone column chromatography (solvent: chloroform / methanol 100 / 1~10 / 1), and the fraction obtained 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).

[0298] [Chemistry 56]

[0299] Identification of compounds represented by formula (I-5a-1) (Mass Analysis) Ionization Mode = ESI+: m / z = 712.6, divalent

[0300] [Example 13 of pigment synthesis: Synthesis of compound (I-5a-2)] The following reaction was carried out under nitrogen atmosphere. Four parts of the compound represented by formula (I-5a-1) and 26.7 parts of methanol were added to a flask including a cooling tube and a stirring device, and then stirred at room temperature for 30 minutes to prepare a blue solution. 17.8 parts of water were added to a flask including a cooling pipe and a stirring device, and then 6.2 parts of phosphotungstic acid hydrate (Kingkin type phosphotungstic acid; manufactured by Sigma-Aldrich) were added to the water. The mixture was then mixed in air at room temperature to prepare a phosphotungstic acid solution. The previously prepared blue solution and 53.4 parts of washing methanol were added dropwise to the obtained phosphotungstic acid solution. The mixture was heated to 55°C in an oil bath while stirring for 4 hours, and then cooled to room temperature. The reaction mixture was concentrated to obtain a crude substance. 40 parts of ion-exchanged water were added to the obtained crude substance to form a suspension, which was then filtered and washed successively with 50 parts of ion-exchanged water and 10 parts of methanol. The obtained crude substance was dispersed in 80 parts of methanol for 1 hour, then filtered and washed with 50 parts of methanol. The blue solid obtained by this operation was dried under reduced pressure at 60°C to obtain 7.51 parts of the compound represented by formula (I-5a-2).

[0301] [Chemistry 57]

[0302] Identification of compounds represented by formula (I-5a-2) (Mass Analysis) Ionization Mode = MALDI+: m / z = 1423.7 Ionization mode = MALDI-: m / z = 2902.5

[0303] [Example 14 of pigment synthesis: Synthesis of compound (I-5b)] Ten parts of the compound represented by formula (I-5a-1) were mixed with 253 parts of sulfuric acid and stirred at 60°C for 6 hours. After cooling, the resulting mixture was added to 1300 parts of ice water to form a suspension, which was then filtered to obtain a crude product. The crude product was purified using silicone 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 (75% yield).

[0304] [Chem.58]

[0305] Identification of compounds represented by formula (I-5b) (Mass Analysis) Ionization Mode = ESI+: m / z = 793.4, divalent

[0306] [Example 15 of pigment synthesis: Synthesis of compound (I-4a-1)] Except for using the compound represented by formula (CI-4) instead of the compound represented by formula (CI-2), the compound represented by formula (I-4a-1) was obtained in the same manner as in pigment synthesis example 12.

[0307] [Chemistry 59]

[0308] Identification of compounds represented by formula (I-4a-1) (Mass Analysis) Ionization Mode = ESI+: m / z = 740.6, divalent

[0309] [Example 16 of pigment synthesis: Synthesis of compound (I-4a-2)] Except for using the compound represented by formula (I-4a-1) instead of the compound represented by formula (I-5a-1), the compound represented by formula (I-4a-2) was obtained in the same manner as in pigment synthesis example 13.

[0310] [Transformation 60]

[0311] Identification of compounds represented by formula (I-4a-2) (Mass Analysis) Ionization Mode = MALDI+: m / z = 1479.8 Ionization mode = MALDI-: m / z = 2902.5

[0312] [Example 17 of pigment synthesis: Synthesis of compound (I-4b)] Ten parts of the compound represented by formula (I-4a-1) were mixed with 253 parts of sulfuric acid and stirred at 60°C for 6 hours. After cooling, the resulting mixture was added to 1300 parts of ice water to form a suspension, which was then filtered to obtain a crude product. The crude product was purified by silicone 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%).

[0313] [Chemistry 61]

[0314] Identification of the compound represented by formula (I-4b) (Mass Analysis) Ionization Mode = ESI+: m / z = 820.4

[0315] [Example 18 of pigment synthesis: Synthesis of compound (I-9a-1)] The compound represented by formula (CI-6) was used instead of the compound represented by formula (CI-2), and the compound represented by formula (BI-3) was used instead of the compound represented by formula (BI-1). Otherwise, the compound represented by formula (I-9a-1) was obtained in the same manner as in pigment synthesis example 12.

[0316] [Chemistry 62]

[0317] Identification of compounds represented by formula (I-9a-1) (Mass Analysis) Ionization Mode = ESI+: m / z = [M] + 786.7, Divalent

[0318] [Example 19 of pigment synthesis: Synthesis of compound (I-9a-2)] Except for using the compound represented by formula (I-9a-1) instead of the compound represented by formula (I-5a-1), the compound represented by formula (I-9a-2) was obtained in the same manner as in pigment synthesis example 13.

[0319] [Chemistry 63]

[0320] Identification of compounds represented by formula (I-9a-2) (Mass Analysis) Ionization Mode = MALDI+: m / z = [MH] + 1571.6 Ionization mode = MALDI-: m / z = [M + H + Na] - 2902.5

[0321] [Example 20 of pigment synthesis: Synthesis of compound (I-56a-1)] Except for using the compound represented by formula (BI-4) instead of the compound represented by formula (BI-1), the compound represented by formula (I-56a-1) was obtained in the same manner as in pigment synthesis example 12.

[0322] [Chemistry 64]

[0323] Identification of compounds represented by formula (I-56a-1) (Mass Analysis) Ionization Mode = MALDI+: m / z = 1491.7

[0324] [Example 21 of pigment synthesis: Synthesis of compound (I-56a-2)] Except for using the compound represented by formula (I-56a-1) instead of the compound represented by formula (I-5a-1), the compound represented by formula (I-56a-2) was obtained in the same manner as in pigment synthesis example 13.

[0325] [Chemistry 65]

[0326] Identification of compounds represented by formula (I-56a-2) (Mass Analysis) Ionization Mode = MALDI+: m / z = 1491.7 Ionization mode = MALDI-: m / z = 2902.5

[0327] [Example 22 of pigment synthesis: Synthesis of compound (I-59a-1)] Except for using the compound represented by formula (BI-5) instead of the compound represented by formula (BI-1), the compound represented by formula (I-59a-1) was obtained in the same manner as in pigment synthesis example 12.

[0328] [Chemistry 66]

[0329] Identification of compounds represented by formula (I-59a-1) (Mass Analysis) Ionization Mode = MALDI+: m / z = 1483.8

[0330] [Example 23 of pigment synthesis: Synthesis of compound (I-59a-2)] Except for using the compound represented by formula (I-59a-1) instead of the compound represented by formula (I-5a-1), the compound represented by formula (I-59a-2) was obtained in the same manner as in pigment synthesis example 13.

[0331] [Chemistry 67]

[0332] Identification of compounds represented by formula (I-59a-2) (Mass Analysis) Ionization Mode = MALDI+: m / z = 1483.8 Ionization mode = MALDI-: m / z = 2902.5

[0333] [Example 24 of pigment synthesis: Synthesis of compound (x1)] The compound represented by the following formula (x1) was synthesized according to the contents disclosed in Japanese Patent Application Publication No. 2014-108975.

[0334] [Chemistry 68]

[0335] [Example 25 of pigment synthesis: Synthesis of compound (x2)] The compound represented by the following formula (x2) was synthesized based on the contents disclosed in Japanese Patent Application Publication No. 2014-108975.

[0336] [Chemistry 69]

[0337] <Resin Synthesis> [Resin Synthesis Example 1] A suitable amount of nitrogen gas was circulated into a flask containing a reflux cooler, a dropping funnel, and a stirrer to create a nitrogen atmosphere. 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 85°C while stirring. Then, over a period of 5 hours, a mixed solution of 38 parts of acrylic acid, 25 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6]decane-9-yl acrylate (containing 1:1 molar ratio), 137 parts of N-cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added dropwise. Simultaneously, over a period of 6 hours, a solution prepared by dissolving 5 parts of 2,2-azobisisobutyronitrile in 88 parts of propylene glycol monomethyl ether acetate was added dropwise. After the addition was complete, the mixture was kept at 85°C for 4 hours, then cooled to room temperature to obtain a copolymer (resin B-1) solution with a viscosity of 23 mPa·s 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 × 10³, the dispersion was 2.1, and the acid value converted from solid content was 10⁹ mg-KOH / g. Resin B-1 has the following structural units.

[0338] [Chemistry 70]

[0339] The determination of the weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin was performed using gel permeation chromatography (GPC) under the following conditions. Device: K2479 (manufactured by Shimadzu Corporation) Tube Column: Shimadzu Shim-pack GPC-80M Column temperature: 40℃ Solvent: tetrahydrofuran (THF) Test solution concentration: 25 mg / mL (solvent: THF) Flow rate: 1.0 mL / min Detector: RI Calibration standard materials: TSK Standard Polystyrene F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight-average molecular weight to the number-average molecular weight of the obtained polystyrene is defined as the dispersity (Mw / Mn).

[0340] [Example 1] <Preparation of a colorant dispersion (A-1) containing compound (I-5a-2)> Five parts of compound (I-5a-2), three parts of acrylic dispersant, two parts of resin B-1 (solids conversion), 79 parts of propylene glycol monomethyl ether acetate, 10 parts of diacetone alcohol, one part of ethyl lactate, and 300 parts of 0.2 mm zirconia beads were mixed and shaken for one hour using a paint conditioner (manufactured by LAU). The zirconia beads were then removed by filtration to obtain a colorant dispersion (A-1).

[0341] <Preparation of Coloring Resin Composition> 245 parts of colorant (A): colorant dispersion (A-1) (B) Resin: Resin (B-1) (solid composition conversion) 45 parts (C) Polymer compound: Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 copies (D) Polymerization initiator: TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) 3 parts (F) Surfactants: Fluorinated surfactants (Megafac (registered trademark) F554; manufactured by DIC) 0.09 parts (E) Solvent: Propylene glycol monomethyl ether acetate (E-1) 506 parts (E) Solvent: Ethyl lactate (E-2) 27 parts The colored resin composition is obtained by mixing.

[0342] [Examples 2-7, Comparative Examples 1-2] Except for changing compound (I-5a-2) to the following compounds, the colored resin compositions were obtained in the same manner as in Example 1. Example 2: Compound (I-5b) Example 3: Compound (I-4a-2) Example 4: Compound (I-4b) Example 5: Compound (I-9a-2) Example 6: Compound (I-56a-2) Example 7: Compound (I-59a-2) Comparative Example 1: Compound (x1) Comparative Example 2: Compound (x2)

[0343] <Production example 1> (Preparation of the red resin composition) 8 parts of colorant (A): Acid Red 52 (manufactured by Tokyo Chemical Industry Co., Ltd.) (B) Resin: Resin (B-1) (solid composition conversion) 50 parts (C) Polymer compound: Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 copies (D) Polymerization initiator: TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) 3 parts (F) Surfactants: Fluorinated surfactants (Megafac (registered trademark) F554; manufactured by DIC) 0.09 parts (E) Solvent: Propylene glycol monomethyl ether acetate (E-1) 127 parts (E) Solvent: Ethyl lactate (E-2) 30 parts (E) Solvent: 4-hydroxy-4-methyl-2-pentanone (E-3) 472 parts A red resin composition is obtained by mixing.

[0344] Formation of Colored Coating (Color Filter) On a 2-inch square glass substrate (Eagle 2000; manufactured by Corning), the colored resin compositions obtained in Examples 1-7 and Comparative Examples 1-2, as well as the red resin composition obtained in Preparation Example 1, were coated by spin coating. The substrates were then pre-baked at 100°C for 3 minutes to form composition layers. After cooling, the composition layers were irradiated with light at an exposure dose of 60 mJ / cm² (365 nm reference) under atmospheric conditions using an exposure machine (TME-150RSK; manufactured by Topcon). The layers were then baked in an oven at 230°C for 20 minutes to obtain a colored coating film.

[0345] <Measurement via spectroscopy> The transmission spectra of the colored coatings obtained from Examples 1 to 7, Comparative Examples 1 to 2, and Preparation Example 1 were measured using an Olympus colorimeter (OSP-SP-200).

[0346] <Brightness Calculation> The International Commission on Illumination (CIE) chromaticity coordinates and stimulus values ​​Y were determined when the colored resin compositions of Examples 1-7 or Comparative Examples 1-2 were mixed with the red resin composition of Preparation Example 1 at the ratios shown in Table 10. The CIE chromaticity coordinates and stimulus values ​​Y were calculated using the transmission spectra obtained from the colored coatings of Examples 1-7 and Comparative Examples 1-2, the transmission spectrum obtained from the colored coating of Preparation Example 1, and the characteristic function of the C light source. The mixing ratios in Table 10 are all combinations that result in the CIE chromaticity coordinates (x, y) = (0.150, 0.060). The values ​​of the stimulus values ​​Y are shown in Table 10. A higher Y value indicates higher brightness.

[0347] [Table 10] composition(%) Stimulus value Y I-5a-2 I-5b I-4a-2 I-4b I-9a-2 I-56a-2 I-59a-2 x1 x2 AR52 Example 1 76 twenty four 6.7 Example 2 75 25 6.7 Example 3 86 14 6.4 Example 4 67 33 6.6 Example 5 68 32 5.9 Example 6 74 26 6.7 Example 7 76 twenty four 6.8 Comparative Example 1 85 15 4.5 Comparative Example 2 88 12 1.4

[0348] In Table 10, each description represents the following coloring agent. I-5a-2: Compound (I-5a-2) I-5b: Compound (I-5b) I-4a-2: Compound (I-4a-2) I-4b: Compound (I-4b) I-9a-2: Compound (I-9a-2) I-56a-2: Compound (I-56a-2) I-59a-2: Compound (I-59a-2) x1: Compound (x1) x2: Compound (x2) AR52: Acid Red 52

[0349] none

Claims

1. A compound represented by formula (I); [In formula (I), R1 to R4 and R13 independently represent hydrogen atoms or hydrocarbon groups having 1 to 10 carbon atoms that may have substituents; R5 to R12 independently represent hydrogen atoms, halogen atoms or hydrocarbon groups having 1 to 5 carbon atoms that may have substituents; 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 α-valent aliphatic hydrocarbon group 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 an integer of 1 or more; d represents an integer of 0 or more; Xc- represents a c-valent anion] [In formula (i), T3 represents an α-valent aromatic hydrocarbon group that may have substituents or an α-valent aromatic heterocyclic group that may have substituents; L2 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that may have substituents;] a represents the same meaning as a in equation (I); * represents the bond with T2.

2. The compound as claimed in claim 1, wherein, R1 and R3 represent phenyl groups that may have substituents, and R2 and R4 represent hydrocarbon groups having 2 to 10 carbon atoms. The phenyl groups of R1 and R3 have an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions adjacent to the N bonded to the phenyl group.

3. A coloring resin composition comprising a colorant and a resin, wherein the colorant comprises a compound as described in claim 1 or claim 2.

4. The coloring resin composition as described in claim 3, wherein, The content of the colorant is 0.1% by mass or more and 50% by mass or less relative to the total amount of solid components in the coloring resin composition.

5. The coloring resin composition as described in claim 3 further contains a polymerizable compound and a polymerization initiator.

6. A color filter formed from a coloring resin composition as described in claim 5.

7. A display device comprising a color filter as described in claim 6.

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