Compounds

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 and T 2 Independently representing divalent aromatic hydrocarbon groups that may have substituents or divalent aromatic heterocyclic groups that may have substituents, L 1 This refers to an α-valent aliphatic hydrocarbon group with 1 to 12 carbon atoms that may have substituents, or a group represented by formula (i), wherein at least one methylene group contained in the aliphatic hydrocarbon group is substituted with -O-, and α represents an integer of 2 or more. [In formula (i), T] 3 L represents an α-valent aromatic hydrocarbon group that may have substituents or an α-valent aromatic heterocyclic group that may have substituents. 2 This refers to a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that may have substituents, wherein at least one of the methylene groups is substituted with -O-.

Description

Technical Field

[0001] This invention relates to compounds, coloring resin compositions, color filters, and display devices. Background Technology

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state imaging elements such as CCDs and CMOS sensors, are made from coloring resin compositions. Various colorants have been used as the coloring resin compositions for forming these color filters; examples of such colorants include compounds represented by the following formulas (x1) and (x2) (Patent Document 1).

[0003]

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Japanese Patent Application Publication No. 2014-108975 Summary of the Invention

[0007] However, color filters formed from coloring resin compositions containing the above-mentioned compounds sometimes fail to achieve sufficiently satisfactory brightness. Therefore, the objective of this invention is to provide a compound capable of forming color filters with excellent brightness.

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

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

[0010]

[0011] In formula (I),

[0012] R 1 ~R 4 and R 13 Hydrogen atoms or hydrocarbon groups with 1 to 10 carbon atoms that may have substituents can be represented independently.

[0013] R 5 ~R 12 Each group can independently represent a hydrogen atom, a halogen atom, or a hydrocarbon group with 1 to 5 carbon atoms that may have substituents.

[0014] T 1 and T 2 They can be represented independently as divalent aromatic hydrocarbon groups that may have substituents or divalent aromatic heterocyclic groups that may have substituents.

[0015] L 1It represents an α-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms that may have substituents, or a group represented by formula (i), wherein at least one of the methylene groups contained in the aliphatic hydrocarbon group is substituted by -O-.

[0016] 'a' represents an integer greater than or equal to 2.

[0017] b and c represent integers greater than 1 independently.

[0018] d represents an integer greater than or equal to 0.

[0019] X c- This indicates a c-valent anion.

[0020]

[0021] In formula (i),

[0022] T 3 This indicates an α-valent aromatic hydrocarbon group that may have substituents or an α-valent aromatic heterocyclic group that may have substituents.

[0023] L 2 It represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that may have substituents, wherein at least one of the methylene groups contained in the aliphatic hydrocarbon group is substituted by -O-.

[0024] * indicates that it is related to T 2 The bonding sites.

[0025] [2] A coloring resin composition comprising a colorant and a resin, wherein the colorant comprises the compound described in [1].

[0026] [3] The coloring resin composition according to [2] further comprises a polymerizable compound and a polymerization initiator.

[0027] [4] A color filter formed from the coloring resin composition described in [2] or [3].

[0028] [5] A display device comprising the color filter described in [4].

[0029] According to the present invention, a compound is provided that can form a color filter with excellent brightness. Detailed Implementation

[0030] <Compound>

[0031] 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).

[0032]

[0033] In formula (I),

[0034] R 1 ~R 4 and R 13 Hydrogen atoms or hydrocarbon groups with 1 to 10 carbon atoms that may have substituents can be represented independently.

[0035] R 5 ~R 12 Each group can independently represent a hydrogen atom, a halogen atom, or a hydrocarbon group with 1 to 5 carbon atoms that may have substituents.

[0036] T 1 and T 2 They can be represented independently as divalent aromatic hydrocarbon groups that may have substituents or divalent aromatic heterocyclic groups that may have substituents.

[0037] L 1 It represents an α-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms that may have substituents, or a group represented by formula (i), wherein at least one of the methylene groups contained in the aliphatic hydrocarbon group is substituted by -O-.

[0038] 'a' represents an integer greater than or equal to 2.

[0039] b and c represent integers greater than 1 independently.

[0040] d represents an integer greater than or equal to 0.

[0041] X c- This indicates a c-valent anion.

[0042]

[0043] In formula (i),

[0044] T 3 This indicates an α-valent aromatic hydrocarbon group that may have substituents or an α-valent aromatic heterocyclic group that may have substituents.

[0045] L 2 It represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that may have substituents, wherein at least one of the methylene groups contained in the aliphatic hydrocarbon group is substituted by -O-.

[0046] 'a' has the same meaning as above.

[0047] * indicates that it is related to T 2 The bonding sites.

[0048] As R 1 ~R 4 and R 13Hydrocarbon groups representing 1 to 10 carbon atoms can include aliphatic and aromatic hydrocarbon groups. Aliphatic hydrocarbon groups can be saturated or unsaturated, and can be chain-like or alicyclic.

[0049] Examples of saturated or unsaturated chain hydrocarbon groups include straight-chain alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-dodecyl; and isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, (1-ethyl)pentyl, (3-ethyl)pentyl, (1-propyl)pentyl, (1-butyl)pentyl, and isohexyl. Branched 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, and (2-ethyl)octyl; and alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl)vinyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl))vinyl, (1,2-dimethyl)propenyl, and 2-pentenyl.

[0050] Examples of cycloalkyl groups that can be classified as saturated or unsaturated alicyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.; cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, etc.; norbornyl, adamantyl, bicyclo[2.2.2]octyl, etc.

[0051] Examples of aromatic hydrocarbon groups include aryl groups such as phenyl, 1-naphthyl, and 2-naphthyl; alkylaryl groups such as 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, and p-tert-butylphenyl; and alkenylaryl groups such as 4-vinylphenyl.

[0052] The aforementioned hydrocarbon groups with 1 to 10 carbon atoms, provided the upper limit for the number of carbon atoms is 10, can also be groups formed by combining two or more of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups mentioned above. Examples of such groups include benzyl, phenethyl, 1-methyl-1-phenylethyl, and other arylalkyl groups; arylalyl groups such as phenylvinyl (phenylvinyl); arylynyl groups such as phenylethynyl; 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... Hexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, etc., alicyclic hydrocarbon groups bonded with one or more alkyl or alicyclic hydrocarbon groups; cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, 2-methylcyclohexylmethyl, cyclohexylethyl, etc., alkyl groups bonded with one or more alicyclic hydrocarbon groups, etc.

[0053] Substituents (hereinafter sometimes referred to as substituent A) that can be present in the hydrocarbon groups having 1 to 10 carbon atoms can be selected from halogen atoms, hydroxyl groups, alkoxy groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, and -SO3 groups. - At least one of -SO3M, where M represents a hydrogen atom or an alkali metal atom.

[0054] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine.

[0055] Examples of alkoxy groups include methoxy, ethoxy, propoxy, and butoxy alkoxy groups with 1 to 4 carbon atoms.

[0056] 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, for example, 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, and N,N-ethylphenylamino.

[0057] Examples of alkali metal atoms mentioned above include sodium and potassium.

[0058] As R5 ~R 12 Examples of halogen atoms that can be represented include fluorine, chlorine, bromine, and iodine.

[0059] As R 5 ~R 12 The hydrocarbon group representing 1 to 5 carbon atoms can be exemplified by aliphatic hydrocarbon groups with 1 to 5 carbon atoms. Specifically, R can be cited as an example. 1 ~R 4 and R 13 The aliphatic hydrocarbon group is a group with 1 to 5 carbon atoms.

[0060] Examples of substituents that can be present in hydrocarbon groups having 1 to 5 carbon atoms include the group exemplified as substituent A.

[0061] T 1 and T 2 The term "divalent aromatic hydrocarbon group" refers to a group obtained by substituting two hydrogen atoms directly bonded to the carbon atoms constituting the aromatic hydrocarbon ring into bonding sites. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group can be either a monocyclic or fused ring; examples include benzene rings, naphthalene rings, anthracene rings, and structures obtained by substituting at least one hydrogen atom of these aromatic hydrocarbon rings into a hydrocarbon group. Examples of such hydrocarbon groups include the aforementioned R... 1 ~R 4 and R 13 The groups exemplified by the hydrocarbon groups representing 1 to 10 carbon atoms are preferably saturated chain hydrocarbon groups, aryl or alkylaryl groups, and more preferably saturated chain hydrocarbon groups representing 1 to 4 carbon atoms. The number of hydrocarbon groups bonded to the aromatic hydrocarbon ring is preferably 0 to 4, and more preferably 0 to 3. Specifically, divalent aromatic hydrocarbon groups can be represented by groups represented by the following formulas (Ta-1) to (Ta-8).

[0062]

[0063] T 1 and T 2 The term "divalent aromatic heterocyclic group" refers to a group obtained by substituting two hydrogen atoms that are directly bonded to the atoms constituting the ring in an aromatic heterocycle as bonding sites. The aromatic heterocycle constituting the divalent aromatic heterocyclic group can be either a monocyclic or fused ring; examples include pyrrole rings, etc. Structures obtained by substituting at least one hydrogen atom of azole rings, pyrazole rings, imidazole rings, thiazole rings, furan rings, thiophene rings, pyridine rings, pyrimidine rings, pyridazine rings, indole rings, benzimidazole rings, benzothiazole rings, quinoline rings, benzofuran rings, and other aromatic heterocycles into a hydrocarbon group. Examples of the aforementioned hydrocarbon groups include those described above as R... 1 ~R 4 and R13 The exemplified group represented by the hydrocarbon group having 1 to 10 carbon atoms is preferably a saturated chain hydrocarbon group, an aryl group, or an alkylaryl group. The number of hydrocarbon groups bonded to the aromatic heterocycle is preferably 0 to 4, more preferably 0 to 3.

[0064] As a substituent that can be present in the above-mentioned divalent aromatic hydrocarbon group and divalent aromatic heterocyclic group, the group exemplified as substituent A can be cited.

[0065] L 1 The α-valent aliphatic hydrocarbon group, representing 1 to 12 carbon atoms, refers to a group obtained by substituting α hydrogen atoms of the aliphatic hydrocarbon into bonding sites. Preferably, the α bonding sites are located in 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.

[0066] The α-valent chain hydrocarbon group can be saturated or unsaturated, but is preferably a saturated α-valent chain hydrocarbon group. Examples of α-valent saturated chain hydrocarbon groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, and other alkane diyl groups; alkane triyl groups represented by formulas (a-1) to (a-2) below; and alkane tetrayl groups represented by formula (a-3) below. The number of carbon atoms in the α-valent chain hydrocarbon group is preferably 1 to 8, more preferably 2 to 6.

[0067]

[0068] 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, more preferably 3 to 6.

[0069] Examples of α-valent groups formed by combining chain hydrocarbon groups with alicyclic hydrocarbon groups include groups represented by the following formulas (a-5) to (a-7).

[0070]

[0071] L 1At least one methylene group in the α-valent aliphatic hydrocarbon group with 1 to 12 carbon atoms is substituted with -O-. Not all adjacent methylene groups are substituted with -O-. The number of methylene groups substituted with -O- is, for example, 1 to 6, preferably 1 to a, more preferably a. The position of the methylene group substituted with -O- is not particularly limited, but preferably at least one methylene group adjacent to the bonding site of the α-valent aliphatic hydrocarbon group is substituted with -O-, more preferably all methylene groups adjacent to the bonding site of the α-valent aliphatic hydrocarbon group are substituted with -O-.

[0072] As at least one of the methylene groups contained in the α-valent aliphatic hydrocarbon group that is substituted by -O-, specifically, groups represented by the following formulas (l-1a) to (l-24a) can be cited, preferably groups represented by formulas (l-1a) to (l-16a), (l-18a) to (l-19a), and (l-22a) to (l-24a), more preferably groups represented by formulas (l-1a), (l-10a) to (l-16a), (l-18a) to (l-19a), and (l-22a) to (l-24a), and even more preferably groups represented by formulas (l-10a) to (l-16a).

[0073]

[0074] Examples of substituents that can be present in α-valent aliphatic hydrocarbon groups with 1 to 12 carbon atoms include the group exemplified as substituent A.

[0075] L 1 It can be a group represented by formula (i).

[0076] In equation (i), T 3 The α-valent aromatic hydrocarbon group refers to a group obtained by substituting α hydrogen atoms, which are directly bonded to the carbon atoms constituting the aromatic hydrocarbon ring, into bonding sites. Examples of aromatic hydrocarbon rings constituting α-valent aromatic hydrocarbon groups include the structures described above for aromatic hydrocarbon rings constituting divalent aromatic hydrocarbon groups.

[0077] In equation (i), T 3 The α-valent aromatic heterocyclic group refers to a group obtained by substituting α hydrogen atoms, which are directly bonded to the atoms constituting the ring, into bonding sites in an aromatic heterocycle. Examples of aromatic heterocycles constituting α-valent aromatic heterocyclic groups include the structures described above for aromatic heterocycles constituting divalent aromatic heterocyclic groups.

[0078] As a substituent that the above-mentioned α-valent aromatic hydrocarbon group and α-valent aromatic heterocyclic group can have, the group exemplified as substituent A can be cited.

[0079] In equation (i), L is used as 2The divalent aliphatic hydrocarbon group representing 1 to 5 carbon atoms can be exemplified by divalent chain hydrocarbon groups with 1 to 5 carbon atoms and divalent alicyclic hydrocarbon groups with 1 to 5 carbon atoms.

[0080] The divalent chain hydrocarbon group can be saturated or unsaturated, but is preferably a divalent saturated chain hydrocarbon group. Examples of divalent saturated chain hydrocarbon groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and other alkane diyl groups.

[0081] The divalent alicyclic hydrocarbon group can be saturated or unsaturated, but is preferably a divalent saturated alicyclic hydrocarbon group. Examples of divalent saturated alicyclic hydrocarbon groups include cyclopropyl-1,2-diyl and cyclobutyl-1,3-diyl.

[0082] L 2 In the divalent aliphatic hydrocarbon group representing 1 to 5 carbon atoms, at least one methylene group is substituted with -O-. Not all adjacent methylene groups are substituted with -O-. The number of methylene groups substituted with -O- is, for example, 1 to 3, preferably 1 to 2. The position of the methylene group substituted with -O- is not particularly limited, but it is preferred to be adjacent to T. 2 The methylene group adjacent to the bonding site is substituted with -O-.

[0083] As a group consisting of at least one methylene group in a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms, which is formed by substitution with -O-, specifically, groups represented by the following formulas (l-1b) to (l-12b) can be cited, wherein groups represented by formulas (l-2b) to (l-5b) are preferred.

[0084]

[0085] [In the formula, * indicates that it is related to T] 2 The binding site, ** indicates the binding site with T 3 The bonding sites.

[0086] As a substituent that can be present in the aforementioned divalent aliphatic hydrocarbon groups having 1 to 5 carbon atoms, the group exemplified as substituent A can be cited.

[0087] Specifically, the groups represented by formula (i) can be exemplified by the groups represented by the following formulas (i1) to (i8).

[0088]

[0089] In equations (i1) to (i8), L i1 ~L i8 Each of these groups independently represents an alkane diene with 1 to 5 carbon atoms, wherein one of the methylene groups is substituted with -O-. * indicates a group related to T. 2The bonding sites.

[0090] The position of the methylene group substituted with -O- is not particularly limited, but it is preferred to be with T. 2 The methylene group adjacent to the bonding site is substituted with -O-.

[0091] Multiple L i1 ~L i8 They can be the same or different, but the same is preferred.

[0092] As X c- The c-valent anion can be represented by well-known anions, specifically halides such as fluoride ions, chloride ions, bromide ions, and iodide ions, boron-containing anions, aluminum-containing anions, fluorine-containing anions, and anions containing at least one element selected from tungsten, molybdenum, silicon, and phosphorus and oxygen as an essential element.

[0093] As boron-containing anions and aluminum-containing anions, for example, anions represented by the following formula (4) can be cited.

[0094]

[0095] In equation (4), W 1 W 2 Each of these groups independently represents a substituent having two substituents formed by the release of protons from a monovalent proton-donating substituent. M represents boron or aluminum.

[0096] Examples of substituent groups having two substituents formed by releasing protons from monovalent proton-donating substituents include groups formed by releasing protons from each of the two proton-donating substituents in compounds having at least two monovalent proton-donating substituents (e.g., hydroxyl, carboxylic acid, etc.). Preferably, such compounds include catechol, 2,3-dihydroxynaphthalene, 2,2'-biphenol, 3-hydroxy-2-naphthoic acid, 2-hydroxy-1-naphthoic acid, 1-hydroxy-2-naphthoic acid, binaphthol, salicylic acid, diphenylglycolic acid, or mandelic acid.

[0097] In the compounds exemplified above, substituents include saturated hydrocarbon groups (e.g., alkyl, cycloalkyl, etc.), halogen atoms, haloalkyl groups, hydroxyl groups, amino groups, nitro groups, alkoxy groups, etc.

[0098] 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), and 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.

[0099] Examples of diphenylethanolic acid that can have substituents include:

[0100]

[0101] Examples of mandelic acid that can have substituents include:

[0102] wait.

[0103] Preferred anions among those represented by formula (4) include anions represented by the following formulas and having the substituents listed in the table, such as anions (BC-1) to anions (BC-24), and anions (BC-25) to anions (BC-28) represented by formulas (BC-25), (BC-26), (BC-27), and (BC-28), respectively.

[0104]

[0105] [Table 1]

[0106] anions <![CDATA[R 61 ]]> <![CDATA[R 62 ]]> <![CDATA[R 63 ]]> <![CDATA[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) <![CDATA[NH2]]> H H H Anion (BC-15) H <![CDATA[NH2]]> H H Anion (BC-16) H H <![CDATA[NH2]]> H Anion (BC-17) H H H <![CDATA[NH2]]> 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

[0107]

[0108]

[0109] 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).

[0110] As fluorine-containing anions, for example, the groups represented by the following formulas (6), (7), (8), and (9) can be cited.

[0111]

[0112] In equation (6), W 3 and W 4 Each independently represents a fluorine atom or a fluoroalkyl group having 1 to 4 carbon atoms, or, W 3 and W 4 Together they represent the dimethyl groups of fluoroalkanes with 1 to 4 carbon atoms.

[0113]

[0114] In equation (7), W 5 ~W 7 Each can independently represent a fluorine atom or a fluoroalkyl group having 1 to 4 carbon atoms.

[0115]

[0116] In equation (8), Y 1 This refers to the dimethyl group of fluoroalkanes with 1 to 4 carbon atoms.

[0117]

[0118] In equation (9), Y 2 This refers to fluoroalkyl groups having 1 to 4 carbon atoms.

[0119] In formulas (6), (7) and (9), the fluoroalkyl 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, and -C(CF3)3.

[0120] In formulas (6) and (8), the fluoroalkane dimethyl group with 1 to 4 carbon atoms is preferably a perfluoroalkane dimethyl group. Examples of perfluoroalkane dimethyl groups include -CF2-, -CF2CF2-, -CF2CF2CF2-, -C(CF3)2-, and -CF2CF2CF2CF2-.

[0121] As an anion represented by formula (6) (hereinafter sometimes referred to as "anion (6)"), examples can be given of anions represented by formulas (6-1) to (6-6) (hereinafter sometimes referred to as "anion (6-1)" to "anion (6-6)").

[0122]

[0123] As an anion represented by formula (7) (hereinafter sometimes referred to as "anion (7)"), examples of anions represented by the following formula (7-1) can be given.

[0124]

[0125] As an anion represented by formula (8) (hereinafter sometimes referred to as "anion (8)"), examples can be given of anions represented by formulas (8-1) to (8-4) (hereinafter sometimes referred to as "anion (8-1)" to "anion (8-4)").

[0126]

[0127] As an anion represented by formula (9) (hereinafter sometimes referred to as "anion (9)"), examples can be given of anions represented by formulas (9-1) to (9-4) (hereinafter sometimes referred to as "anion (9-1)" to "anion (9-4)").

[0128]

[0129] By making X c- The c-valent anion is selected from at least one anion (i.e., a fluorine-containing anion) chosen from anion (6), anion (7), anion (8), and anion (9), thereby improving the solubility of compound (I) in organic solvents. Among these, anion (6-1), anion (6-2), and anion (7-1) are preferred, and anion (6-2) is particularly preferred.

[0130] As X c- The c-valent anion can be an anion containing at least one element selected from tungsten, molybdenum, silicon and phosphorus, and oxygen as an essential element. It is preferred to have anions of heteropolyacids or isopolyacids containing tungsten as an essential element, and more preferably anions of phosphotungstic acid, silicotungstic acid and tungsten-based isopolyacids.

[0131] Examples of anions of heteropolyacids or homopolyacids containing tungsten as an essential element include, for instance, the Keggin-type phosphotungstic acid ion α-[PW] 12 O 40 ] 3- Dawson-type phosphotungstic acid ions α-[P2W]18 O 62 ] 6- β-[P2W 18 O 62 ] 6- Keggin-type silicotungstate ions α-[SiW 12 O 40 ] 4- β-[SiW 12 O 40 ] 4- γ-[SiW 12 O 40 ] 4- And [P2W] as another example 17 O 61 ] 10- [P2W] 15 O 56 ] 12- [H2P2W] 12 O 48 ] 12- [NaP5W] 30 O 110 ] 14- α-[SiW9O 34 ] 10- γ-[SiW 10 O 36 ] 8- α-[SiW 11 O 39 ] 8- β-[SiW 11 O 39 ] 8- [W6O] 19 ] 2- [W] 10 O 32 ] 4- WO4 2- wait.

[0132] In addition, among anions other than those of heteropolyacids or isopolyacids containing tungsten as an essential element, anions composed of at least one element selected from silicon and phosphorus and oxygen are preferred.

[0133] Examples of such anions composed of at least one element selected from silicon and phosphorus and oxygen include SiO3. 2- PO4 3- .

[0134] In particular, considering the ease of synthesis and post-processing, heteropolyacid anions such as Keggin-type phosphotungstate ions, Dawson-type phosphotungstate ions, and Keggin-type silicotungstate ions are preferred, along with [W 10 O32 ] 4- Equivalent to polyacid anions.

[0135] In equation (I), multiple R 1 ~R 13 T 1 T 2 and L 1 They can be the same or different, but are preferably the same. Furthermore, in equation (i), multiple L... 2 They can be the same or different, but the same is preferred.

[0136] Preferred R 1 ~R 4 Each can be 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.

[0137] R is the preferred choice 1 and R 3 Each is independently 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, and R 2 and R 4 Each can be an independent saturated chain hydrocarbon group with 1 to 10 carbon atoms that may have substituents.

[0138] More preferably R 1 and R 3 Each can independently be a phenyl group that can have substituents, and R 2 and R 4 Each can be an independent saturated chain hydrocarbon group with 1 to 10 carbon atoms that may have substituents.

[0139] Further optimization of R 1 and R 3 Each is independently a phenyl group that may have substituents and has an alkyl group having 1 to 4 carbon atoms at least one of the two bonding positions adjacent to the N of the phenyl group, and R 2 and R 4 Each can be an independent saturated chain hydrocarbon group with 1 to 6 carbon atoms that can have substituents.

[0140] Further optimization of R 1 and R 3 Each is independently a phenyl group that may have substituents and has an alkyl group having 1 to 4 carbon atoms at least one of the two bonding positions adjacent to the N of the phenyl group, and R 2 and R 4 Each is independently a saturated chain hydrocarbon group with 2 to 6 carbon atoms that can have substituents.

[0141] R is the preferred choice 1 and R 3 Each is independently a phenyl group that may have substituents and has an alkyl group having 1 to 3 carbon atoms at two bonding positions adjacent to the N bonded to the phenyl group, and R 2 and R 4 Each can be an independent saturated chain hydrocarbon group with 2 to 6 carbon atoms that can have substituents.

[0142] Here, examples of substituents that the aforementioned phenyl group may have include alkyl groups having 1 to 4 carbon atoms, halogen atoms, hydroxyl groups, alkoxy groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, and -SO3 groups. - At least one of -SO3M (M is the same as above), wherein preferably, it is selected from alkyl, halogen, alkoxy and -SO3 groups having 1 to 4 carbon atoms. - At least one of the following, more preferably, is selected from alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and -SO3. - At least one of them.

[0143] In particular, when the phenyl group has an alkoxy group (preferably a methoxy group) as a substituent, the brightness of the resulting color filter can be further improved. The substitution position of the alkoxy group (preferably a methoxy group) is not particularly limited; the effect can be further enhanced by bonding it at the para position relative to the N group bonded to the phenyl group.

[0144] The aforementioned R 1 ~R 4 Among the preferred methods, R is particularly preferred. 1 and R 3 Each can be independently any of the groups represented by formulas (r1) to (r3). It should be noted that any one or more of the hydrogen atoms in the groups represented by formulas (r1) to (r3) can be derived from -SO3. - replace.

[0145]

[0146] [In the formula, R] r1 ~R r4 Each alkyl group independently represents an alkyl group with 1 to 4 carbon atoms. * indicates a bonding site.

[0147] R r1 ~R r4 Methyl is preferred.

[0148] R 5 ~R 12 Hydrogen atoms are preferred.

[0149] R 13 Preferably, it is a hydrogen atom or a hydrocarbon group with 1 to 6 carbon atoms that may have substituents, more preferably a hydrogen atom or a saturated chain hydrocarbon group with 1 to 6 carbon atoms that may have substituents, and even more preferably a hydrogen atom, methyl, ethyl, n-propyl or isopropyl.

[0150] T 1 Preferably, it is a divalent aromatic hydrocarbon group that can have substituents. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is preferably a benzene ring, a naphthalene ring, or a structure obtained by substituting at least one hydrogen atom of these rings with a saturated chain hydrocarbon group having 1 to 10 (preferably 1 to 4) carbon atoms. As T 1 More preferably, it is any one of the groups represented by the above formulas (Ta-1) to (Ta-8), and particularly preferably the group represented by the above formula (Ta-8).

[0151] T 2 Preferably, it is 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 obtained by substituting at least one hydrogen atom of these rings with a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4). More preferably, it is a structure obtained by substituting at least one hydrogen atom of the benzene ring with a saturated chain hydrocarbon group having 1 to 4 carbon atoms. As T 2 Further preferred are any of the groups represented by the following formulas (Tb-1) to (Tb-10), even more preferred are any of the groups represented by the following formulas (Tb-3), (Tb-5), (Tb-6), (Tb-9), and (Tb-10), and particularly preferred are any of the groups represented by the following formulas (Tb-5), (Tb-6), (Tb-9), and (Tb-10).

[0152]

[0153] [In the formula, * indicates that it is related to L] 1 The ** indicates the bonding site with the nitrogen atom.

[0154] As in equation (i), T is preferred. 3 For α-valent aromatic hydrocarbon groups that can have substituents, L 2 It is a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, and at least one of the methylene groups contained in the saturated chain hydrocarbon group is obtained by substitution with -O-, more preferably any of the groups represented by formulas (i1) to (i8) above, further preferably a group represented by formula (i2) or formula (i3) above, and particularly preferably any of the groups represented by formulas (i-1) to (i-6) below.

[0155]

[0156] [In the formula, * indicates that it is related to T] 2 The bonding sites.

[0157] As L 1 Preferably, it is an α-valent aliphatic hydrocarbon group having 1 to 8 carbon atoms that can have substituents, and at least one of the methylene groups contained in the aliphatic hydrocarbon group is formed by substitution with -O-, or any of the groups represented by formulas (i1) to (i8) above.

[0158] More preferably, it is an α-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms and having a substituent, wherein at least one of the methylene groups contained in the aliphatic hydrocarbon group is substituted with -O-, or a group represented by formula (i2) or formula (i3) above.

[0159] More preferably, it is an α-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms that may have substituents, and at least one of the methylene groups contained in the aliphatic hydrocarbon group is formed by -O- substitution, or any of the groups represented by formulas (i-1) to (i-6) above.

[0160] It is particularly preferred to be any of the groups represented by formulas (l-10a) to (l-16a) or formulas (i-1) to (i-6) above.

[0161] As X c- The c-valent anion is preferably a halide ion or an anion containing at least one element preferred from tungsten, molybdenum, silicon and phosphorus and oxygen as an essential element, more preferably a halide ion or an anion containing tungsten as an essential element of a heteropolyacid or isopolyacid, and even more preferably a halide ion, Keggin type phosphotungstate ion or Dawson type phosphotungstate ion.

[0162] The substituents (i.e., substituent A) present in compound (I) are preferably selected from halogen atoms, hydroxyl groups, alkoxy groups, substituted or unsubstituted amino groups, and -SO3 groups. - At least one of -SO3M, more preferably selected from halogen atoms, alkoxy groups, and -SO3 - At least one of -SO3M.

[0163] a is preferably an integer from 2 to 6, more preferably an integer from 2 to 4, and even more preferably 2 or 3.

[0164] c is typically 1 to 14, preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 4.

[0165] b and d are based on the -SO3 group present in a, c, and compound (I) as substituents. -The number of elements (hereinafter sometimes referred to as e) determines the charge, and generally, the charge of the entire equation (I) is adjusted to be 0. Therefore, usually, a to d in equation (I) satisfy the following relationship (z).

[0166] a×b=(c×d)+e···(z)

[0167] In the above formula, a to d have the same meaning as above. e represents the -SO3 group present in compound (I) as a substituent. - The number of [items].

[0168] e is an integer greater than or equal to 0, preferably 0 to (a+1), more preferably 0 to a, and even more preferably 0 or a. In particular, when d is 1 or greater, e is preferably 0, meaning that compound (I) does not possess -SO3. - When d is 0, the preferred value is e = a.

[0169] In particular, from the viewpoint of heat resistance and solvent resistance, X is preferred. c- A compound containing at least one element selected from tungsten, molybdenum, silicon and phosphorus and an anion of oxygen as an essential element, with d=1 or more and e=0.

[0170] As compound (I), it is preferably a compound represented by formula (I-1) or formula (I-2).

[0171]

[0172] In formula (I-1),

[0173] R 101 and R 103 Each can be an independent phenyl group that can have substituents.

[0174] R 102 and R 104 Each can be an independent saturated chain hydrocarbon group with 1 to 10 carbon atoms that may have substituents.

[0175] R 105 ~R 112 It is hydrogen.

[0176] R 113 It is hydrogen or a saturated chain hydrocarbon group with 1 to 6 carbon atoms that may have substituents.

[0177] T 101 and T 102 It is a structure in which a divalent aromatic hydrocarbon group with substituents is formed, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring, a naphthalene ring, or at least one hydrogen atom of these rings is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms.

[0178] L 101It is an aliphatic hydrocarbon group with 1 to 8 carbon atoms having substituents, wherein at least one of the methylene groups contained in the aliphatic hydrocarbon group is substituted with -O-, or in the group represented by formula (i) T 3 For a101-valent aromatic hydrocarbon groups that can have substituents, L 2 It is a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, and at least one of the methylene groups contained in the saturated chain hydrocarbon group is substituted with -O-.

[0179] a101 is 2 or 3.

[0180] d101 represents an integer greater than or equal to 1.

[0181] b, c, and X c- This indicates the same meaning as above.

[0182]

[0183] In formula (I-2),

[0184] R 201 and R 203 Each can be an independent phenyl group that can have substituents.

[0185] R 202 and R 204 Each can be an independent saturated chain hydrocarbon group with 1 to 10 carbon atoms that may have substituents.

[0186] R 205 ~R 212 It is hydrogen.

[0187] R 213 It is hydrogen or a saturated chain hydrocarbon group with 1 to 6 carbon atoms that may have substituents.

[0188] T 201 and T 202 It is a structure in which a divalent aromatic hydrocarbon group with substituents is formed, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring, a naphthalene ring, or at least one hydrogen atom of these rings is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms.

[0189] L 201 It is an aliphatic hydrocarbon group with 1 to 8 carbon atoms having substituents, wherein at least one of the methylene groups contained in the aliphatic hydrocarbon group is substituted by -O-, or in the group represented by formula (i) T 3 For a201-valent aromatic hydrocarbon groups that can have substituents, L 2 It is a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, and at least one of the methylene groups contained in the saturated chain hydrocarbon group is substituted with -O-.

[0190] a201 and e201 are 2 or 3.

[0191] The compound represented by formula (I-2) has R 201 ~R 213 T 201 T 202 and L 201 The arbitrary e201 hydrogen atoms possessed by SO3 - replace.]

[0192] As R 101 R 103 R 201 and R 203 The phenyl group may have at least one substituent selected from alkyl groups having 1 to 4 carbon atoms, halogen atoms, hydroxyl groups, alkoxy groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, and -SO3M (where M is a hydrogen atom or an alkali metal atom). Preferably, at least one substituent is selected from alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms. The halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described for substituent A.

[0193] R 101 R 103 R 201 and R 203 Preferably, the phenyl group may have a substituent and has an alkyl group having 1 to 4 carbon atoms in at least one (preferably both) of the two bonding positions adjacent to the N bonded to the phenyl group. R is particularly preferred. 101 R 103 R 201 and R 203 Each is independently any of the groups represented by the above formulas (r1) to (r3).

[0194] R 102 R 104 R 202 and R 204 Preferably, it is a saturated chain hydrocarbon group having 1 to 6 carbon atoms that can have substituents, more preferably a saturated chain hydrocarbon group having 2 to 6 carbon atoms. As R 102 R 104 R 202 and R 204The saturated chain hydrocarbon group may have at least one substituent (hereinafter referred to as substituent B) selected from halogen atoms, hydroxyl groups, alkoxy groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, and -SO3M (where M is a hydrogen atom or an alkali metal atom). The halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described for substituent A.

[0195] As R 113 and R 213 The substituents that a saturated chain hydrocarbon group with 1 to 6 carbon atoms can have are exemplified by the group described as substituent B.

[0196] As T 101 and T 201 The divalent aromatic hydrocarbon group can have substituents, and examples of substituent B can be given. As for T... 101 and T 201 Preferably, it is any one of the groups represented by the above formulas (Ta-1) to (Ta-8), and more preferably, it is a group represented by formula (Ta-8).

[0197] As T 102 and T 202 The divalent aromatic hydrocarbon group may have substituents, such as the group described as substituent B, wherein preferably at least one is selected from halogen atoms and alkoxy groups. As T 102 and T 202 Preferably, it is a divalent aromatic hydrocarbon group that may 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, it is any of the groups represented by the above formulas (Tb-1) to (Tb-10), and particularly preferably any of the groups represented by formulas (Tb-5), (Tb-6), (Tb-9), and (Tb-10).

[0198] In equations (I-1) and (I-2), L is used as 101 and L 201 The T group represents α-valent saturated chain hydrocarbons with 1 to 8 carbon atoms. 3 The α-valent aromatic hydrocarbon group represented by L in formula (i) 2 The substituents that can be present can be exemplified by the group described as substituent B.

[0199] As L 101 and L 201Preferably, it is an α-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms that can have substituents, and at least one of the methylene groups contained in the aliphatic hydrocarbon group is formed by -O- substitution, or any of the groups represented by formulas (i1) to (i8) above.

[0200] More preferably, it is an α-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms and having a substituent, wherein at least one of the methylene groups contained in the aliphatic hydrocarbon group is substituted with -O-, or a group represented by formula (i2) or formula (i3) above.

[0201] It is particularly preferred to be any of the groups represented by formulas (l-10a) to (l-16a) or formulas (i-1) to (i-6) above.

[0202] a201 and e201 are preferably the same.

[0203] The compounds represented by preferred formulas (I-1) and (I-2) have a charge of 0.

[0204] It should be noted that, from the viewpoint of heat resistance and solvent resistance, the compound represented by formula (I-1) is preferred.

[0205] Specifically, examples of compound (I) include compounds (I-1a-1) to (I-108a-1) and compounds (I-1a-2) to (I-108a-2) represented by formula (I-a) below, and compounds (I-1b) to (I-108b) represented by formula (I-b) below. It should be noted that the compounds represented by formula (I-b) represent compounds in compound (I) where b is 1 and d is 0. The R of the compounds represented by formula (I-b) 1b ~R 13b T 1b T 2b and L 1b Any e2 atoms in the hydrogen atoms contained in SO3 - replace.

[0206]

[0207] [Table 2]

[0208] <![CDATA[R 1a ,R 3a ]]> <![CDATA[R 2a ,R 4a ]]> <![CDATA[R 5a～ R 12a ]]> <![CDATA[R 13a ]]> <![CDATA[T 1a ]]> <![CDATA[T 2 a]]> <![CDATA[L 1a ]]> a1 b1 <![CDATA[X c1- ]]> d1 I-1a-1 r-1 Et H H Ta-8 Tb-5 i-1 2 1 <![CDATA[Cl - ]]> 2 I-2a-1 r-2 Et H H Ta-8 Tb-5 i-1 2 1 <![CDATA[Cl - ]]> 2 I-3a-1 r-3 Et H H Ta-8 Tb-5 i-1 2 1 <![CDATA[Cl - ]]> 2 I-4a-1 r-1 Et H H Ta-8 Tb-6 i-1 2 1 <![CDATA[Cl - ]]> 2 I-5a-1 r-2 Et H H Ta-8 Tb-6 i-1 2 1 <![CDATA[Cl - ]]> 2 I-6a-1 r-3 Et H H Ta-8 Tb-6 i-1 2 1 <![CDATA[Cl - ]]> 2 I-7a-1 r-1 Et H Et Ta-8 Tb-5 i-1 2 1 <![CDATA[Cl - ]]> 2 I-8a-1 r-2 Et H Et Ta-8 Tb-5 i-1 2 1 <![CDATA[Cl - ]]> 2 I-9a-1 r-3 Et H Et Ta-8 Tb-5 i-1 2 1 <![CDATA[Cl - ]]> 2 I-10a-1 r-1 Et H Et Ta-8 Tb-6 i-1 2 1 <![CDATA[Cl - ]]> 2 I-11a-1 r-2 Et H Et Ta-8 Tb-6 i-1 2 1 <![CDATA[Cl - ]]> 2 I-12a-1 r-3 Et H Et Ta-8 Tb-6 i-1 2 1 <![CDATA[Cl - ]]> 2 I-13a-1 r-1 Et H Pr Ta-8 Tb-5 i-1 2 1 <![CDATA[Cl - ]]> 2 I-14a-1 r-2 Et H Pr Ta-8 Tb-5 i-1 2 1 <![CDATA[Cl - ]]> 2 I-15a-1 r-3 Et H Pr Ta-8 Tb-5 i-1 2 1 <![CDATA[Cl - ]]> 2 I-16a-1 r-1 Et H Pr Ta-8 Tb-6 i-1 2 1 <![CDATA[Cl - ]]> 2 I-17a-1 r-2 Et H Pr Ta-8 Tb-6 i-1 2 1 <![CDATA[Cl - ]]> 2 I-18a-1 r-3 Et H Pr Ta-8 Tb-6 i-1 2 1 <![CDATA[Cl - ]]> 2 I-19a-1 r-1 Et H H Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - ]]> 3 I-20a-1 r-2 Et H H Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - ]]> 3 I-21a-1 r-3 Et H H Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - ]]> 3 I-22a-1 r-1 Et H H Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - ]]> 3 I-23a-1 r-2 Et H H Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - ]]> 3 I-24a-1 r-3 Et H H Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - ]]> 3 I-25a-1 r-1 Et H Et Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - ]]> 3 I-26a-1 r-2 Et H Et Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - ]]> 3 I-27a-1 r-3 Et H Et Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - ]]> 3 I-28a-1 r-1 Et H Et Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - ]]> 3 I-29a-1 r-2 Et H Et Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - ]]> 3 I-30a-1 r-3 Et H Et Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - ]]> 3 I-31a-1 r-1 Et H Pr Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - ]]> 3 I-32a-1 r-2 Et H Pr Ta-8 Tb-5 i-4 3 1 Cr 3 I-33a-1 r-3 Et H Pr Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - ]]> 3 I-34a-1 r-1 Et H Pr Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - ]]> 3 I-35a-1 r-2 Et H Pr Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - ]]> 3 I-36a-1 r-3 Et H Pr Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - ]]> 3 I-37a-1 r-1 Et H H Ta-8 Tb-5 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-38a-1 r-2 Et H H Ta-8 Tb-5 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-39a-1 r-3 Et H H Ta-8 Tb-5 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-40a-1 r-1 Et H H Ta-8 Tb-6 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-41a-1 r-2 Et H H Ta-8 Tb-6 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-42a-1 r-3 Be H H Ta-8 Tb-6 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-43a-1 r-1 Be H Be Ta-8 Tb-5 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-44a-1 r-2 Be H Be Ta-8 Tb-5 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-45a-1 r-3 Be H Be Ta-8 Tb-5 I-13a 2 1 <![CDATA[Cl - ]]> 2

[0209] [Table 3]

[0210] <![CDATA[R 1a ,R 3a ]]> <![CDATA[R 2a ,R 4a ]]> <![CDATA[R 5a～ R 12a ]]> <![CDATA[R 13a ]]> <![CDATA[T 1a ]]> <![CDATA[T 2a ]]> <![CDATA[L 1a ]]> a1 b1 <![CDATA[X c1- ]]> d1 I-46a-1 r-1 Be H Be Ta-8 Tb-6 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-47a-1 r-2 Be H Be Ta-8 Tb-6 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-48a-1 r-3 Be H Be Ta-8 Tb-6 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-49a-1 r-1 Be H Pr Ta-8 Tb-5 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-50a-1 r-2 Be H Pr Ta-8 Tb-5 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-51a-1 r-3 Be H Pr Ta-8 Tb-5 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-52a-1 r-1 Be H Pr Ta-8 Tb-6 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-53a-1 r-2 Be H Pr Ta-8 Tb-6 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-54a-1 r-3 Be H Pr Ta-8 Tb-6 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-55a-1 r-1 Be H H Ta-8 Tb-9 i-1 2 1 <![CDATA[Cl - ]]> 2 I-56a-1 r-2 Be H H Ta-8 Tb-9 i-1 2 1 <![CDATA[Cl - ]]> 2 I-57a-1 r-3 Be H H Ta-8 Tb-9 i-1 2 1 <![CDATA[Cl - ]]> 2 I-58a-1 r-1 Be H H Ta-8 Tb-10 i-1 2 1 <![CDATA[Cl - ]]> 2 I-59a-1 r-2 Be H H Ta-8 Tb-10 i-1 2 1 <![CDATA[Cl - ]]> 2 I-60a-1 r-3 Be H H Ta-8 Tb-10 i-1 2 1 <![CDATA[Cl - ]]> 2 I-61a-1 r-1 Be H Be Ta-8 Tb-9 i-1 2 1 <![CDATA[Cl - ]]> 2 I-62a-1 r-2 Be H Be Ta-8 Tb-9 i-1 2 1 <![CDATA[Cl - ]]> 2 I-63a-1 r-3 Be H Be Ta-8 Tb-9 i-1 2 1 <![CDATA[Cl - ]]> 2 I-64a-1 r-1 Be H Be Ta-8 Tb-10 i-1 2 1 <![CDATA[Cl - ]]> 2 I-65a-1 r-2 Be H Be Ta-8 Tb-10 i-1 2 1 <![CDATA[Cl - ]]> 2 I-66a-1 r-3 Be H Be Ta-8 Tb-10 i-1 2 1 <![CDATA[Cl - ]]> 2 I-67a-1 r-1 Be H Pr Ta-8 Tb-9 i-1 2 1 <![CDATA[Cl - ]]> 2 I-68a-1 r-2 Be H Pr Ta-8 Tb-9 i-1 2 1 <![CDATA[Cl - ]]> 2 I-69a-1 r-3 Be H Pr Ta-8 Tb-9 i-1 2 1 <![CDATA[Cl - ]]> 2 I-70a-1 r-1 Be H Pr Ta-8 Tb-10 i-1 2 1 <![CDATA[Cl - ]]> 2 I-71a-1 r-2 Be H Pr Ta-8 Tb-10 i-1 2 1 <![CDATA[Cl - ]]> 2 I-72a-1 r-3 Be H Pr Ta-8 Tb-10 i-1 2 1 <![CDATA[Cl - ]]> 2 I-73a-1 r-1 Be H H Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - ]]> 3 I-74a-1 r-2 Be H H Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - ]]> 3 I-75a-1 r-3 Be H H Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - ]]> 3 I-76a-1 r-1 Be H H Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - ]]> 3 I-77a-1 r-2 Be H H Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - ]]> 3 I-78a-1 r-3 Be H H Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - ]]> 3 I-79a-1 r-1 Be H Be Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - ]]> 3 I-80a-1 r-2 Be H Be Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - ]]> 3 I-81a-1 r-3 Be H Be Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - ]]> 3 I-82a-1 r-1 Be H Be Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - ]]> 3 I-83a-1 r-2 Be H Be Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - ]]> 3 I-84a-1 r-3 Be H Be Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - ]]> 3 I-85a-1 r-1 Be H Pr Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - ]]> 3 I-86a-1 r-2 Be H Pr Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - ]]> 3 I-87a-1 r-3 Be H Pr Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - ]]> 3 I-88a-1 r-1 Be H Pr Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - ]]> 3 I-89a-1 r-2 Be H Pr Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - ]]> 3 I-90a-1 r-3 Be H Pr Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - ]]> 3

[0211] [Table 4]

[0212] <![CDATA[R 1a ,R 3a ]]> <![CDATA[R 2a ,R 4a ]]> <![CDATA[R 5a～ R 12a ]]> <![CDATA[R 13a ]]> <![CDATA[T 1a ]]> <![CDATA[T 2a ]]> <![CDATA[L 1a ]]> a1 b1 <![CDATA[x c1- ]]> d1 I-91a-1 r-1 Be H H Ta-8 Tb-9 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-92a-1 r-2 Be H H Ta-8 Tb-9 I-13a 2 1 <![CDATA[Cl - ]]> 2 I-93a-1 r-3 Be H H Year-8 Tb-9 13a 2 1 <![CDATA[Cl - ]]> 2 94a-1 r-1 And H H Year-8 Tb-10 13a 2 1 <![CDATA[Cl - ]]> 2 95a-1 r-2 And H H Year-8 Tb-10 13a 2 1 <![CDATA[Cl - ]]> 2 96a-1 r-3 And H H Year-8 Tb-10 13a 2 1 <![CDATA[Cl - ]]> 2 97a-1 r-1 And H And Year-8 Tb-9 13a 2 1 <![CDATA[Cl - ]]> 2 98a-1 r-2 And H And Year-8 Tb-9 13a 2 1 <![CDATA[Cl - ]]> 2 99a-1 r-3 And H And Year-8 Tb-9 13a 2 1 <![CDATA[Cl - ]]> 2 100a-1 r-1 And H And Year-8 Tb-10 13a 2 1 <![CDATA[Cl - ]]> 2 101a-1 r-2 And H And Year-8 Tb-10 13a 2 1 <![CDATA[Cl - ]]> 2 102a-1 r-3 And H And Year-8 Tb-10 13a 2 1 <![CDATA[Cl - ]]> 2 103a-1 r-1 And H Pr Year-8 Tb-9 13a 2 1 <![CDATA[Cl - ]]> 2 104a-1 r-2 And H Pr Year-8 Tb-9 13a 2 1 <![CDATA[Cl - ]]> 2 105a-1 r-3 And H Pr Year-8 Tb-9 13a 2 1 <![CDATA[Cl - ]]> 2 106a-1 r-1 And H Pr Year-8 Tb-10 13a 2 1 <![CDATA[Cl - ]]> 2 107a-1 r-2 And H Pr Year-8 Tb-10 13a 2 1 <![CDATA[Cl - ]]> 2 108a-1 r-3 And H Pr Year-8 Tb-10 13a 2 1 <![CDATA[Cl - ]]> 2 1a-2 r-1 And H H Year-8 Tb-5 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 2a-2 r-2 And H H Year-8 Tb-5 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 3a-2 r-3 And H H Year-8 Tb-5 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 4a-2 r-1 And H H Year-8 Tb-6 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 5a-2 r-2 And H H Year-8 Tb-6 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 6a-2 r-3 And H H Year-8 Tb-6 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 7a-2 r-1 And H And Year-8 Tb-5 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 8a-2 r-2 And H And Year-8 Tb-5 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 9a-2 r-3 And H And Year-8 Tb-5 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 10a-2 r-1 And H And Year-8 Tb-6 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 11a-2 r-2 And H And Year-8 Tb-6 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 12a-2 r-3 And H And Year-8 Tb-6 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 13a-2 r-1 And H Pr Year-8 Tb-5 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 14a-2 r-2 And H Pr Year-8 Tb-5 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 15a-2 r-3 And H Pr Year-8 Tb-5 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 16a-2 r-1 And H Pr Year-8 Tb-6 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 17a-2 r-2 And H Pr Year-8 Tb-6 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 18a-2 r-3 And H Pr Year-8 Tb-6 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 19a-2 r-1 And H H Year-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 20a-2 r-2 And H H Year-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 21a-2 r-3 And H H Year-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> l 22a-2 r-1 And H H Year-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 23a-2 r-2 And H H Year-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 24a-2 r-3 And H H Year-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 25a-2 r-1 And H And Year-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 26a-2 r-2 And H And Year-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 27a-2 r-3 And H And Year-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1

[0213] [Table 5]

[0214] <![CDATA[R 1a ,R 3a ]]> <![CDATA[R 2a ,R 4a ]]> <![CDATA[R 5a～ R 12a ]]> <![CDATA[R 13a ]]> <![CDATA[T 1a ]]> <![CDATA[T 2a ]]> <![CDATA[L 1a ]]> a1 b1 <![CDATA[X c1- ]]> d1 28a-2 r-1 And H And Year-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 29a-2 r-2 And H And Year-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 30a-2 r-3 And H And Year-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 31a-2 r-1 And H Pr Year-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 32a-2 r-2 And H Pr Year-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 33a-2 r-3 And H Pr Year-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 34a-2 r-1 And H Pr Year-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 the 40 ] 3- ]]> 1 35a-2 r-2 And H Pr Year-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 36a-2 r-3 And H Pr Year-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 37a-2 r-1 And H H Year-8 Tb-5 13a 2 3 <![CDATA[[PW 12 THE 4a ] 3- ]]> 2 38a-2 r-2 And H H Year-8 Tb-5 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 39a-2 r-3 And H H Year-8 Tb-5 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 40a-2 r-1 And H H Year-8 Tb-6 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 41a-2 r-2 And H H Year-8 Tb-6 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 42a-2 r-3 And H H Year-8 Tb-6 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 43a-2 r-1 And H And Year-8 Tb-5 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 44a-2 r-2 And H And Year-8 Tb-5 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 45a-1 rr-3 And H And Year-8 Tb-5 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 46a-2 r-1 And H And Year-8 Tb-6 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 47a-2 r-2 And H And Year-8 Tb-6 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 48a-2 r-3 And H And Year-8 Tb-6 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 49a-2 r-1 And H Pr Year-8 Tb-5 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 50a-2 r-2 And H Pr Year-8 Tb-5 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 51a-2 r-3 And H Pr Year-8 Tb-5 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 52a-2 r-1 And H Pr Year-8 Tb-6 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 53a-2 r-2 And H Pr Year-8 Tb-6 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 54a-2 r-3 And H Pr Year-8 Tb-6 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 55a-2 r-1 And H H Year-8 Tb-9 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 56a-2 r-2 And H H Year-8 Tb-9 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 57a-2 r-3 And H H Year-8 Tb-9 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 58a-2 r-1 And H H Year-8 Tb-10 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 59a-2 r-2 And H H Year-8 Tb-10 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 60a-2 r-3 And H H Year-8 Tb-10 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 61a-2 r-1 And H And Year-8 Tb-9 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 62a-2 r-2 And H And Year-8 Tb-9 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 63a-2 r-3 And H And Year-8 Tb-9 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 64a-2 r-1 And H And Year-8 Tb-10 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 65a-2 r-2 And H And Year-8 Tb-10 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 66a-2 r-3 And H And Year-8 Tb-10 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 67a-2 r-1 And H Pr Year-8 Tb-9 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 68a-2 r-2 And H Pr Year-8 Tb-9 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 69a-2 r-3 And H Pr Year-8 Tb-9 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 70a-2 r-1 And H Pr Year-8 Tb-10 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 71a-2 r-2 And H Pr Year-8 Tb-10 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 72a-2 r-3 And H Pr Year-8 Tb-10 i-1 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2

[0215] [Table 6]

[0216] <![CDATA[R 1a ,R 3a ]]> <![CDATA[R 2a ,R 4a ]]> <![CDATA[R 5a～ R 12a ]]> <![CDATA[R 13a ]]> <![CDATA[T 1a ]]> <![CDATA[T 2a ]]> <![CDATA[L 1a ]]> a1 b1 <![CDATA[× c1- ]]> d1 73a-2 r-1 And H H Year-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 THE 4a ] 3- ]]> 1 74a-2 r-2 And H H Year-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 75a-2 r-3 And H H Year-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 76a-2 r-1 And H H Year-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 77a-2 r-2 And H H Year-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 78a-2 r-3 And H H Year-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 79a-2 r-1 And H And Year-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 80a-2 r-2 And H And Year-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 81a-2 r-3 And H And Year-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 82a-2 r-1 And H And Year-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 83a-2 r-2 And H And Year-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 84a-2 r-3 And H And Year-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 85a-2 r-1 And H Pr Year-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 86a-2 r-2 And H Pr Year-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 87a-2 r-3 And H Pr Year-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 88a-2 r-1 And H Pr Year-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 89a-2 r-2 And H Pr Year-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 90a-2 r-3 And H Pr Year-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 THE 40 ] 3- ]]> 1 91a-2 r-1 And H H Year-8 Tb-9 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 92a-2 r-2 And H H Year-8 Tb-9 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 93a-2 r-3 And H H Year-8 Tb-9 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 94a-2 r-1 And H H Year-8 Tb-10 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 95a-2 r-2 And H H Year-8 Tb-10 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 96a-2 r-3 And H H Year-8 Tb-10 13a 2 3 <![CDATA[[Pw 12 THE 40 ] 3- ]]> 2 97a-2 r-1 And H And Year-8 Tb-9 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 98a-2 r-2 And H And Year-8 Tb-9 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 99a-2 r-3 And H And Year-8 Tb-9 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 100a-2 r-1 And H And Year-8 Tb-10 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 101a-2 r-2 And H And Year-8 Tb-10 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 102a-2 r-3 And H And Year-8 Tb-10 13a 2 3 <![CDATA[[PW 12 THE 4a ] 3- ]]> 2 103a-2 r-1 And H Pr Year-8 Tb-9 1-13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 104a-2 r-2 And H Pr Year-8 Tb-9 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 105a-2 r-3 And H Pr Year-8 Tb-9 13a 2 3 <![CDATA[[PW 12 THE 4a ] 3- ]]> 2 106a-2 r-1 And H Pr Year-8 Tb-10 13a 2 3 <![CDATA[[PW 12 THE 4a ] 3- ]]> 2 107a-2 r-2 And H Pr Year-8 Tb-10 13a 2 3 <![CDATA[[PW 12 THE 40 ] 3- ]]> 2 108a-2 r-3 And H Pr Year-8 Tb-10 13a 2 3 <![CDATA[[ PW12 THE 40 ] 3- ]]> 2

[0217]

[0218] [Table 7]

[0219] <![CDATA[R 1b ,R 3b ]]> <![CDATA[R 2b ,R 4b ]]> <![CDATA[R 5b～ R 12b ]]> <![CDATA[R 13b ]]> <![CDATA[T 1b ]]> <![CDATA[T 2b ]]> <![CDATA[L 1b ]]> a2 e2 1b r-1 And H H Year-8 Tb-5 i-1 2 2 2b r-2 And H H Year-8 Tb-5 i-1 2 2 3b r-3 And H H Year-8 Tb-5 i-1 2 2 4b r-1 And H H Year-8 Tb-6 i-1 2 2 5b r-2 And H H Year-8 Tb-6 i-1 2 2 6b r-3 And H H Year-8 Tb-6 i-1 2 2 The 7b r-1 And H And Year-8 Tb-5 i-1 2 2 The 8b r-2 And H And Year-8 Tb-5 i-1 2 2 9b r-3 And H And Year-8 Tb-5 i-1 2 2 10b r-1 And H And Year-8 Tb-6 i-1 2 2 11b r-2 And H And Year-8 Tb-6 i-1 2 2 12b r-3 And H And Year-8 Tb-6 i-1 2 2 13b r-1 And H Pr Year-8 Tb-5 i-1 2 2 14b r-2 And H Pr Year-8 Tb-5 i-1 2 2 15b r-3 And H Pr Year-8 Tb-5 i-1 2 2 16b r-1 And H Pr Year-8 Tb-6 i-1 2 2 17b r-2 And H Pr Year-8 Tb-6 i-1 2 2 18b r-3 And H Pr Year-8 Tb-6 i-1 2 2 19b r-1 And H H Year-8 Tb-5 i-4 3 3 20b r-2 And H H Year-8 Tb-5 i-4 3 3 21b r-3 And H H Year-8 Tb-5 i-4 3 3 22b r-1 And H H Year-8 Tb-6 i-4 3 3 23b r-2 And H H Year-8 Tb-6 i-4 3 3 24b r-3 And H H Year-8 Tb-6 i-4 3 3 25b r-1 And H And Year-8 Tb-5 i-4 3 3 26b r-2 And H And Year-8 Tb-5 i-4 3 3 27b r-3 And H And Year-8 Tb-5 i-4 3 3 28b r-1 And H And Year-8 Tb-6 i-4 3 3 29b r-2 And H And Year-8 Tb-6 i-4 3 3 30b r-3 And H And Year-8 Tb-6 i-4 3 3 31b r-1 And H Pr Year-8 Tb-5 i-4 3 3 32b r-2 And H Pr Year-8 Tb-5 i-4 3 3 33b r-3 And H Pr Year-8 Tb-5 i-4 3 3 34b r-1 And H Pr Ta-8 Tb-6 i-4 3 3 I-35b r-2 Et H Pr Ta-8 Tb-6 i-4 3 3 I-36b r-3 Et H Pr Ta-8 Tb-6 i-4 3 3 I-37b r-1 Et H H Ta-8 Tb-5 I-13a 2 2 I-38b r-2 Et H H Ta-8 Tb-5 I-13a 2 2 I-39b r-3 Et H H Ta-8 Tb-5 I-13a 2 2 I-4Ob r-1 Et H H Ta-8 Tb-6 I-13a 2 2 I-41b r-2 Et H H Ta-8 Tb-6 I-13a 2 2 I-42b r-3 Et H H Ta-8 Tb-6 I-13a 2 2 I-43b r-1 Et H Et Ta-8 Tb-5 I-13a 2 2 I-44b r-2 Et H Et Ta-8 Tb-5 I-13a 2 2 I-45b r-3 Et H Et Ta-8 Tb-5 I-13a 2 2

[0220] [Table 8]

[0221] <![CDATA[R 1b ,R 3b ]]> <![CDATA[R 2b ,R 4b ]]> <![CDATA[R 5b～ R 12b ]]> <![CDATA[R 13b ]]> <![CDATA[T 1b ]]> <![CDATA[T 2b ]]> <![CDATA[L 1b ]]> a2 e2 I-46b r-1 Et H Et Ta-8 Tb-6 I-13a 2 2 I-47b r-2 Et H Et Ta-8 Tb-6 I-13a 2 2 I-48b r-3 Et H Et Ta-8 Tb-6 I-13a 2 2 I-49b r-1 Et H Pr Ta-8 Tb-5 I-13a 2 2 I-50b r-2 Et H Pr Ta-8 Tb-5 I-13a 2 2 I-51b r-3 Et H Pr Ta-8 Tb-5 I-13a 2 2 I-52b r-1 Et H Pr Ta-8 Tb-6 I-13a 2 2 I-53b r-2 Et H Pr Ta-8 Tb-6 I-13a 2 2 I-54b r-3 Et H Pr Ta-8 Tb-6 I-13a 2 2 I-55b r-1 Et H H Ta-8 Tb-9 i-1 2 2 I-56b r-2 Et H H Ta-8 Tb-9 i-1 2 2 I-57b r-3 Et H H Ta-8 Tb-9 i-1 2 2 I-58b r-1 Et H H Ta-8 Tb-10 i-1 2 2 I-59b r-2 Et H H Ta-8 Tb-10 i-1 2 2 I-60b r-3 Et H H Ta-8 Tb-10 i-1 2 2 I-61b r-1 Et H Et Ta-8 Tb-9 i-1 2 2 I-62b r-2 Et H Et Ta-8 Tb-9 i-1 2 2 I-63b r-3 Et H Et Ta-8 Tb-9 i-1 2 2 I-64b r-1 Et H Et Taa-8 Tb-10 i-1 2 2 I-65b r-2 Et H Et Ta-8 Tb-10 i-1 2 2 I-66b r-3 Et H Et Taa-8 Tb-10 i-1 2 2 I-67b r-1 Et H Pr Ta-8 Tb-9 i-1 2 2 I-68b r-2 Et H Pr Ta-8 Tb-9 i-1 2 2 I-69b r-3 Et H Pr Ta-8 Tb-9 i-1 2 2 I-70b r-1 Et H Pr Ta-8 Tb-10 i-1 2 2 I-71b r-2 Et H Pr Ta-8 Tb-10 i-1 2 2 I-72b r-3 Et H Pr Ta-8 Tb-10 i-1 2 2 I-73b r-1 Et H H Ta-8 Tb-9 i-4 3 3 I-74b r-2 Et H H Ta-8 Tb-9 i-4 3 3 I-75b r-3 Et H H Ta-8 Tb-9 i-4 3 3 I-76b r-1 Et H H Ta-8 Tb-10 i-4 3 3 I-77b r-2 Et H H Ta-8 Tb-10 i-4 3 3 I-78b r-3 Et H H Ta-8 Tb-10 i-4 3 3 I-79b r-1 Et H Et Ta-8 Tb-9 i-4 3 3 I-80b r-2 Et H Et Ta-8 Tb-9 i-4 3 3 I-81b r-3 Et H Et Ta-8 Tb-9 i-4 3 3 I-82b r-1 Et H Et Ta-8 Tb-10 i-4 3 3 I-83b r-2 Et H Et Ta-8 Tb-10 i-4 3 3 I-84b r-3 Et H Et Ta-8 Tb-10 i-4 3 3 I-85b r-1 Et H Pr Ta-8 Tb-9 i-4 3 3 I-86b r-2 Et H Pr Ta-8 Tb-9 i-4 3 3 I-87b r-3 Et H Pr Ta-8 Tb-9 i-4 3 3 I-88b r-1 Et H Pr Ta-8 Tb-10 i-4 3 3 I-89b r-2 Et H Pr Ta-8 Tb-10 i-4 3 3 I-90b r-3 Et H Pr Ta-8 Tb-10 i-4 3 3

[0222] [Table 9]

[0223] <![CDATA[R 1b ,R 3b ]]> <![CDATA[R 2b ,R 4b ]]> <![CDATA[R 5b～ R 12b ]]> <![CDATA[R 13b ]]> <![CDATA[T 1b ]]> <![CDATA[T 2b ]]> <![CDATA[L 1b ]]> a2 e2 I-91b r-1 Et H H Ta-8 Tb-9 I-13a 2 2 I-92b r-2 Et H H Ta-8 Tb-9 I-13a 2 2 I-93b r-3 Et H H Ta-8 Tb-9 I-13a 2 2 I-94b r-1 Et H H Ta-8 Tb-10 I-13a 2 2 I-95b r-2 Et H H Ta-8 Tb-10 I-13a 2 2 I-96b r-3 Et H H Ta-8 Tb-10 I-13a 2 2 I-97b r-1 Et H Et Ta-8 Tb-9 I-13a 2 2 I-98b r-2 Et H Et Ta-8 Tb-9 I-13a 2 2 I-99b r-3 Et H Et Ta-8 Tb-9 I-13a 2 2 I-100b r-1 Et H Et Ta-8 Tb-10 I-13a 2 2 I-101b r-2 Et H Et Ta-8 Tb-10 I-13a 2 2 I-102b r-3 Et H Et Ta-8 Tb-10 I-13a 2 2 I-103b r-1 Et H Pr Ta-8 Tb-9 I-13a 2 2 I-104b r-2 Et H Pr Ta-8 Tb-9 I-13a 2 2 I-105b r-3 Et H Pr Ta-8 Tb-9 I-13a 2 2 I-106b r-1 Et H Pr Ta-8 Tb-10 I-13a 2 2 I-107b r-2 Et H Pr Ta-8 Tb-10 I-13a 2 2 I-108b r-3 Et H Pr Ta-8 Tb-10 I-13a 2 2

[0224] In Tables 2-9, H represents a hydrogen atom, Et represents an ethyl group, Pr represents a n-propyl group, r-1 to r-3 represent groups represented by formulas (r-1) to (r-3) below, Ta-8 represents groups represented by formula (Ta-8) below, Tb-5 to Tb-6 and Tb-9 to Tb-10 represent groups represented by formulas (Tb-5) to (Tb-6) and (Tb-9) to (Tb-10) below, i-1 and i-4 represent groups represented by formulas (i-1) and (i-4) below, and 1-13a represents groups represented by formula (1-13a) below.

[0225]

[0226] [In the formula, * indicates the bonding site with a nitrogen atom.]

[0227]

[0228] [In the formula, * represents the bonding site.]

[0229]

[0230] [In the formula, * indicates that it is related to L] 1a or L 1b The ** indicates the bonding site with the nitrogen atom.

[0231]

[0232] [In the formula, * indicates that it is related to T] 2a or T 2b The bonding sites.

[0233] As compound (I), compounds (I-1a-1) to (I-108a-1) and compounds (I-1a-2) to (I-108a-2) are preferred, compounds (I-1a-2) to (I-108a-2) are more preferred, and compounds (I-1a-2) to (I-36a-2), (I-39a-2), (I-42a-2), (I-45a-2), (I-48a-2), (I-51a-2), and (I-54a-2) are even more preferred.

[0234] Compound (I) can be manufactured, for example, by the methods described in (1) to (3) below.

[0235] (1)X c- Method for manufacturing compound (I) which is a halide ion (hereinafter, sometimes referred to as compound (I')).

[0236] Compound (I') can be produced, for example, by reacting a compound represented by formula (B-I) with a compound represented by formula (C-I).

[0237]

[0238] In equations (B-I) and (C-I), R 1 ~R 13 T 2 L 1 'a' and 'a' represent the same meanings as described above. T 1B Indicates that in the above T 1 A group formed by replacing a bonding site different from the one bonded to a nitrogen atom with a hydrogen atom.

[0239] The amount of the compound represented by formula (C-I) used is preferably 0.5 to 10 moles relative to 1 mole of the compound represented by formula (B-I), and more preferably 1 to 4 moles.

[0240] The reaction temperature is preferably 30℃~180℃, more preferably 80℃~130℃. The reaction time is preferably 1 hour~12 hours, more preferably 1 hour~8 hours.

[0241] The above reaction can be carried out in the presence of an organic solvent or without a solvent; however, from the perspective 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 to 20 parts by mass relative to 1 part by mass of the compound represented by formula (B-I), more preferably 2 to 10 parts by mass.

[0242] From a yield perspective, the above reaction is preferably carried out in the presence of a condensing agent. Examples of condensing agents include phosphoric acid, polyphosphoric acid, phosphorus oxychloride, sulfuric acid, and thionyl chloride. When phosphorus oxyhalide, thionyl chloride, or similar condensing agents are used and the relationship in equation (z1) is satisfied, X is obtained. c- It is a compound containing halide ions (I').

[0243] a×b-e>0···(z1)

[0244] In the above formula, a and b have the same meaning as a and b in formula (I). e represents the -SO3 group present in compound (I') as a substituent. - The number of [items].

[0245] The amount of condensing agent used is preferably 0.1 to 20 parts by mass relative to 1 part by mass of the compound represented by formula (B-I), more preferably 0.2 to 10 parts by mass.

[0246] There are no particular limitations on the method for obtaining compound (I') from the reaction mixture; various known methods can be used. After extraction, the residue can be purified by column chromatography or recrystallization.

[0247] As a method for producing compound (B-I), various known techniques can be used, such as the method described in German patent application P3928243.0. Further purification can also be performed using known methods such as recrystallization and chromatographic preparation, as needed.

[0248] Various well-known methods can be cited as methods for producing the compound (C-I). Further purification can also be performed as needed using known methods such as recrystallization and chromatography-based preparation.

[0249] (2)X c- Anions other than halide ions (hereinafter referred to as anion X) 1 Method for manufacturing compound (I) (hereinafter, sometimes referred to as compound (I”)

[0250] Compound (I”) can be obtained by reacting compound (I’) with anion X. 1 It is manufactured by mixing alkali metal salts or protic acids. Examples of alkali metals include lithium, sodium, and potassium.

[0251] The anion X relative to compound (I') 1 The amount of alkali metal salt or protic acid used is determined by the ratio of the cation to the anion X in compound (I'). 1 The stoichiometric ratio of the compounds (I') to which the charges are balanced can be added, for example, 0.5 to 8 moles, more preferably 1 to 3 moles, relative to 1 mole of the compound (I').

[0252] Compound (I') and anion X 1 The mixing of alkali metal salts or protic acids can be carried out by dissolving both in the solvents described below, or it can be carried out without dissolving them.

[0253] Examples of solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, acetonitrile, ethyl acetate, toluene, methanol, ethanol, isopropanol, acetone, tetrahydrofuran, and dimethylformamide. Alkane, water, and chloroform.

[0254] From the viewpoint of solubility, at least one solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, methanol, ethanol, isopropanol and water is preferred.

[0255] The amount of solvent used is preferably 1 to 30 parts by mass relative to 1 part by mass of compound (I'), more preferably 2 to 20 parts by mass.

[0256] When the solvent is water, acids such as acetic acid and hydrochloric acid can be added.

[0257] Compound (I') and anion X 1 The mixing temperature of the alkali metal salt or protic 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.

[0258] When using a water-miscible solvent, the compound (I”) can be obtained by mixing the solution, stirring for 1–3 hours as needed, and then removing the solvent. Alternatively, the obtained compound (I”) can be washed with deionized water, methanol, or other suitable solvents as needed.

[0259] When using a solvent immiscible with water, a solution containing compound (I”) can be obtained by mixing the reaction mixture with ion-exchanged water, stirring for 1–3 hours as needed, and then separating the liquid to obtain the organic layer. Alternatively, the solution can be washed with ion-exchanged water as needed. The solvent is then removed from the solution containing compound (I”), thereby obtaining compound (I”).

[0260] (3) X does not exist. c- Method for manufacturing compounds (i.e., d=0) (hereinafter, sometimes referred to as compound (I”'))

[0261] Compound (I”') can be prepared by mixing compound (I’) with sulfuric acid.

[0262] The amount of sulfuric acid used relative to compound (I') is based on the ratio of cations in compound (I') to -SO3. - The sulfuric acid is added in a stoichiometric ratio to balance the charges of the compound (I'), for example, 0.5 to 8 moles, preferably 1 to 3 moles, relative to 1 mole of the compound (I'). Alternatively, the sulfuric acid can also be used as a reaction solvent. When using sulfuric acid as a solvent, the amount of sulfuric acid used relative to 1 mole of the compound (I') is, for example, 20 moles or more, preferably 25 moles or more. Furthermore, there is no particular upper limit to the amount of sulfuric acid used when using it 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 the compound (I').

[0263] 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.

[0264] The mixture obtained by mixing compound (I') with sulfuric acid can be used to prepare a suspension by adding it to ice water, followed by filtration to obtain compound (I”'). Alternatively, it can be further purified by known methods such as recrystallization or chromatographic preparation as needed.

[0265] <Coloring Resin Composition>

[0266] 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 contains compound (I).

[0267] 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)).

[0268] The coloring resin composition of the present invention preferably further comprises a solvent (hereinafter, sometimes referred to as solvent (E)).

[0269] The coloring resin composition of the present invention may further contain a leveling agent (hereinafter, sometimes referred to as leveling agent (F)).

[0270] It should be noted that, unless otherwise specified, the compounds exemplified as ingredients in this specification may be used alone or in combination.

[0271] <Coloring Agent (A)>

[0272] The colorant (A) contains compound (I). As a result, the brightness of the obtained color filter is good, and preferably, the obtained color filter can also be made into a thin film. Furthermore, by containing compound (I) in the colorant (A), the heat resistance and / or solvent resistance of the preferably obtained color filter are also good. The aforementioned compound (I) can be cited as an example of compound (I), and its preferred form is also as described above.

[0273] 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). They may be used alone or in combination of two or more.

[0274] As long as the dye (A1-1) does not contain compound (I), any known dye can be used without particular limitation; examples include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in color indexes (published by The Society of Dyers and Colourists) and known dyes listed in dyeing guides (for dyeing companies). Furthermore, based on their chemical structure, examples include azo dyes, cyanide dyes, triphenylmethane dyes, xanthones, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methylene dyes, azomethyl base dyes, squaric acid onion dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Among these, organic solvent-soluble dyes are preferred.

[0275] As a dye (A1-1), specifically, examples include:

[0276] 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;

[0277] 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;

[0278] CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;

[0279] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0280] CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

[0281] CI solvent greens 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; and other CI solvent dyes.

[0282] 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, 15 7, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

[0283] 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;

[0284] 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;

[0285] CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

[0286] CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 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;

[0287] CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; and other CI acid dyes.

[0288] 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;

[0289] 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;

[0290] CI direct orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0291] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0292] 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;

[0293] CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; and other CI direct dyes.

[0294] CI Disperse Yellow 51, 54, 76;

[0295] CI Disperse Violet 26, 27;

[0296] CI Disperse Blue 1, 14, 56, 60; and other CI disperse dyes.

[0297] CI Basic Red 1, 9, 10;

[0298] 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;

[0299] CI Basic Violet 2;

[0300] CI Basic Green 1; and other CI basic dyes.

[0301] CI Active Yellow 2, 76, 116;

[0302] CI Active Orange 16;

[0303] CI Reactive Red 36; and other CI reactive dyes.

[0304] CI Media Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0305] CI Media Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;

[0306] CI Media Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0307] CI Media Purple 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;

[0308] CI Media Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84;

[0309] CI mordant greens 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; and other CI mordant dyes.

[0310] CI Reduced Green 1; and other CI reduced dyes, etc., color index (CI) numbered dyes.

[0311] As pigments (A1-2), well-known pigments can be used without particular limitation as long as they do not contain compound (I). For example, pigments classified as pigments in the color index (published by The Society of Dyers and Colourists) can be cited.

[0312] As pigments classified as pigments, examples include CI pigments 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.

[0313] CI pigments include orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and other orange pigments;

[0314] CI pigments include reds 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.

[0315] CI pigment blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments;

[0316] CI pigments include purple 1, 19, 23, 32, 36, 38, and other purple pigments;

[0317] CI pigments include green 7, 36, 58, 59, 62, and 63, among other green pigments.

[0318] CI pigments, such as brown 23 and 25;

[0319] CI Pigment Black 1, 7, and other black pigments.

[0320] As a coloring agent (A1), yellow, red, or green dyes and / or pigments are preferred.

[0321] The colorant (A1) can be subjected to various treatments 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 based on sulfuric acid micronization, cleaning treatment based on organic solvents or water to remove impurities, and removal treatment of ionic impurities based on ion exchange. The particle size of the colorant (A1) is preferably substantially uniform.

[0322] When colorant (A) further contains colorant (A1), the content of compound (I) 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, further preferably 25% by mass or more, and particularly preferably 50% by mass or more. Furthermore, when colorant (A) further contains colorant (A1), the content of compound (I) relative to the total amount of colorant (A) is, for example, less than 100% by mass.

[0323] When the coloring resin composition contains a solvent (E), a solution containing the colorant (A) and the solvent (E) can be prepared in advance, and the coloring resin composition can be prepared using this solution. When the colorant (A) is not soluble in the solvent (E), for example, when the colorant (A) contains pigments (Al-2), the solution containing the colorant can be prepared by dispersing and mixing the colorant (A) in the solvent (E). The solution containing the colorant may contain part or all of the solvent (E) contained in the coloring resin composition.

[0324] The content of solid components in the solution containing colorant relative to the total amount of the solution containing colorant is preferably 0.01% to 99.99% by mass, more preferably 0.1% to 99.9% by mass, even more preferably 0.1% to 99% by mass, even more preferably 0.5% to 90% by mass, and particularly preferably 1% to 50% by mass.

[0325] Colorant (A) can be dispersed in solution by using a dispersant to achieve a uniform dispersion of colorant (A). When two or more colorants (A) are used in combination, they can be dispersed individually or mixed together for dispersion.

[0326] Dispersants, for example, can be surfactants, and can be any of the following: cationic, anionic, nonionic, and amphoteric surfactants. Specifically, examples include polyester-based, polyamine-based, and acrylic 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 Corporation), AJISPER (registered trademark) (manufactured by Ajinomoto Fine Chemicals Co., Ltd.), and Disperbyk (registered trademark) (manufactured by BYK Corporation), BYK (registered trademark) (manufactured by BYK Corporation). Resins (B) described later can also be used as dispersants.

[0327] When using a dispersant, the amount of the dispersant (solid component) used relative to 100 parts by mass of the colorant (A) is typically 1 to 10,000 parts by mass, preferably 5 to 5,000 parts by mass, more preferably 10 to 1,000 parts by mass, and even more preferably 15 to 800 parts by mass. When the amount of the dispersant used is within the above range, there is a tendency to obtain a more uniformly dispersed solution containing the colorant.

[0328] The content of colorant (A) relative to the total amount of solid components in the coloring resin composition is preferably 0.1% to 50% by mass, more preferably 0.5% to 40% by mass, and even more preferably 1% to 30% by mass. When the content of colorant (A) is within the above range, the color concentration is sufficient when used as a color filter, and the composition contains the required amount of resin (B), thus enabling the formation of patterns with sufficient mechanical strength, which is therefore preferred.

[0329] Here, "total amount of solids" in this specification refers to the amount obtained by removing the solvent content from the total amount of the coloring resin composition. The total amount of solids and the content of each component relative to the total amount of solids can be determined, for example, using known analytical methods such as liquid chromatography or gas chromatography.

[0330] <Resin (B)>

[0331] The resin (B) is not particularly limited, but an alkali-soluble resin is preferred. Examples of resin (B) include resins [K1] to [K6].

[0332] Resin [K1]: A copolymer having structural units derived from at least one monomer (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)"), and structural units derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an olefinic unsaturated bond (hereinafter sometimes referred to as "(b)");

[0333] Resin [K2]: A copolymer having structural units from (a), structural units from (b), and structural units from monomer (c) (which is different from (a) and (b)) (hereinafter sometimes referred to as "(c)");

[0334] Resin [K3]: A copolymer having structural units from (a) and structural units from (c);

[0335] Resin [K4]: A copolymer having a structural unit obtained by adding (b) with a structural unit from (a) and a structural unit from (c);

[0336] Resin [K5]: A copolymer having structural units obtained by adding structural units (a) to structural units from (b) and structural units from (c);

[0337] Resin [K6]: A copolymer having a structural unit obtained by adding (a) to a structural unit from (b), and further adding a carboxylic anhydride, and a structural unit from (c).

[0338] As monomers (a), examples include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, zeaxanthinic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexene dicarboxylic acid; methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, and 5-carboxy-5-methyl Bicyclic unsaturated compounds containing carboxyl groups, such as bicyclic [2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclic [2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclic [2.2.1]hept-2-ene; carboxylic anhydrides, such as acid anhydrides of the above-mentioned unsaturated dicarboxylic acids excluding fumaric acid and medronic acid; unsaturated mono[(meth)acryloyloxyethyl] esters of polycarboxylic acids of two or more groups, such as succinic acid mono[2-(meth)acryloyloxyethyl] ester and phthalic acid mono[2-(meth)acryloyloxyethyl] ester; and unsaturated acrylates containing hydroxyl and carboxyl groups in the same molecule, such as α-(hydroxymethyl)acrylic acid.

[0339] Among these, considering the copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solution, acrylic acid, methacrylic acid, and maleic anhydride are preferred.

[0340] It should be noted that in this specification, "(meth)acrylic acid" refers to at least one selected from acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

[0341] Monomer (b) refers to a polymerizable compound having a cyclic ether structure with 2 to 4 carbon atoms (e.g., selected from at least one of oxecyclopropane, oxecyclobutane, and tetrahydrofuran (oxecyclopentane) rings) and an olefinic unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0342] Examples of monomers (b) include monomers having oxetyl and olefinic unsaturated bonds (hereinafter sometimes referred to as "monomer (b1)"), monomers having oxetyl and olefinic unsaturated bonds (hereinafter sometimes referred to as "monomer (b2)"), monomers having tetrahydrofuranyl and olefinic unsaturated bonds (hereinafter sometimes referred to as "monomer (b3)"), etc.

[0343] As monomers (b1), examples include monomers having a structure that epoxidizes unsaturated aliphatic hydrocarbons (hereinafter, sometimes referred to as "monomers (b1-1)") and monomers having a structure that epoxidizes unsaturated alicyclic hydrocarbons (hereinafter, sometimes referred to as "monomers (b1-2)").

[0344] As monomer (b1-1), monomers having glycidyl groups and olefinic unsaturated bonds are preferred. Specifically, examples of monomer (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( Glycidoxymethyl)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.

[0345] Examples of monomers (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl methacrylate (e.g., Cyclomer A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl methacrylate (e.g., Cyclomer M100; manufactured by Daicel Co., Ltd.), compounds represented by formula (BI), and compounds represented by formula (BII).

[0346]

[0347] In equations (BI) and (BII), R a and R bAlkyl groups, which independently represent 1 to 4 hydrogen atoms or carbon atoms, may have hydrogen atoms replaced by hydroxyl groups.

[0348] X a and X b Independently represent single bonds, *-R c -、*-R c -O-、*-R c -S- or *-R c -NH-.

[0349] R c It represents the dimethyl groups of alkanes with 1 to 6 carbon atoms.

[0350] * indicates a binding site with O.

[0351] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.

[0352] Examples of alkyl groups in which the hydrogen atom is replaced by a hydroxyl group 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.

[0353] As R a and R b Examples of preferred elements include hydrogen atoms, methyl groups, hydroxymethyl groups, 1-hydroxyethyl groups, and 2-hydroxyethyl groups; examples of more preferred elements include hydrogen atoms and methyl groups.

[0354] Examples of alkane dimethyl groups include methylene, ethylene, propane-1,2-dimethyl, propane-1,3-dimethyl, butane-1,4-dimethyl, pentane-1,5-dimethyl, and hexane-1,6-dimethyl.

[0355] As X a and X b Examples of preferred compounds include single bonds, methylene, ethylene, *-CH2-O- (* indicates the bonding site with O) group, and *-CH2CH2-O- group; examples of more preferred compounds include single bonds and *-CH2CH2-O- group (* indicates the bonding site with O).

[0356] Examples of compounds represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9), and (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9), and (BI-15) are more preferred.

[0357]

[0358] Examples of compounds represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15), among which compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15) are preferred, and compounds represented by formulas (BII-1), (BII-7), (BII-9), and (BII-15) are more preferred.

[0359]

[0360] The compounds represented by formula (BI) and formula (BII) can be used individually or in combination. When used together, the molar ratio of the compounds represented by formula (BI) to (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

[0361] The monomer (b2) having an oxetyl group and an olefinic unsaturated bond is more preferably a monomer having an oxetyl group and a (meth)acryloyloxy group. Examples of monomers (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, and 3-ethyl-3-(meth)acryloyloxyethyloxetane.

[0362] The monomer (b3) having a tetrahydrofuran group and an olefinic unsaturated bond is more preferably a monomer having a tetrahydrofuran group and a (meth)acryloyloxy group. Examples of monomers (b3) include, for example, tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemicals Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0363] Examples of monomers (c) include, for instance, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, dodecyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclopentyl methacrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, and tricyclo[5.2.1.0] methacrylate. 2 ,6 ] Decane-8-yl ester (in this technical field, it is commonly referred to as "(meth)acrylate dicyclopentyl ester". Additionally, it is sometimes called "(meth)acrylate tricyclodecyl ester"), (meth)acrylate tricyclo[5.2.1.0] 2,6 ] Decane-9-yl ester, (meth)acrylate tricyclic [5.2.1.0] 2,6 ] Decen-8-yl ester (in this technical field, it is commonly referred to as "(meth)acrylate dicyclopentenyl ester"), (meth)acrylate tricyclo[5.2.1.0] 2,6 Decenyl-9-yl ester, dicyclopentoxyethyl ester (meth)acrylate, isobornyl ester (meth)acrylate, adamantyl ester (meth)acrylate, allyl ester (meth)acrylate, propargyl ester (meth)acrylate, phenyl ester (meth)acrylate, naphthyl ester (meth)acrylate, and benzyl ester (meth)acrylate, etc. (meth)acrylates;

[0364] Hydroxyl acrylates such as 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate;

[0365] Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid;

[0366] Bicyclic [2.2.1]hept-2-ene, 5-methylbicyclic [2.2.1]hept-2-ene, 5-ethylbicyclic [2.2.1]hept-2-ene, 5-hydroxybicyclic [2.2.1]hept-2-ene, 5-hydroxymethylbicyclic [2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclic [2.2.1]hept-2-ene, 5-methoxybicyclic [2.2.1]hept-2-ene, 5-ethoxybicyclic [2.2.1]hept-2-ene, 5,6-dihydroxybicyclic [2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclic [2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclic [2.2.1]hept-2-ene, 5,6-dimethoxy Bicyclic unsaturated compounds such as bicyclic[2.2.1]hept-2-ene, 5,6-diethoxybicyclic[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclic[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclic[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclic[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclic[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclic[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclic[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclic[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclic[2.2.1]hept-2-ene;

[0367] Dicarbonyl imide derivatives including N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimide-3-maleimide benzoate, N-succinimide-4-maleimide butyrate, N-succinimide-6-maleimide hexanoate, N-succinimide-3-maleimide propionate, and N-(9-acridyl)maleimide;

[0368] Aromatic compounds containing vinyl groups, such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; nitriles containing vinyl groups, such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; 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.

[0369] Among these, considering copolymerization reactivity and heat resistance, materials selected from styrene, vinyltoluene, and tricyclo(meth)acrylate [5.2.1.0] are preferred. 2,6 ] Decane-8-yl ester, (meth)acrylate tricyclic [5.2.1.0] 2,6 ] Decane-9-yl ester, (meth)acrylate tricyclic [5.2.1.0] 2,6] Decen-8-yl ester, (meth)acrylate tricyclic [5.2.1.0] 2,6 At least one of the following: decen-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, 2-hydroxyethyl methacrylate and benzyl methacrylate.

[0370] In resin [K1], the ratio of structural units from each structural unit is preferably 2 to 60 mol% from (a) and 40 to 98 mol% from (b) among all structural units constituting resin [K1], more preferably 10 to 50 mol% from (a) and 50 to 90 mol% from (b).

[0371] When the ratio of the structural units of resin [K1] is within the above range, there is a tendency for the coloring resin composition to have excellent storage stability, developability when forming coloring patterns, and solvent resistance of the resulting color filter.

[0372] The resin [K1] can be manufactured, for example, by referring to the method described in the document "Experimental Method for Polymer Synthesis" (Otsu Takayuki Publishing Co., Ltd. Chemical Dojin 1st Edition 1st Printing, March 1, 1972) and the references described in that document.

[0373] Specifically, the following method can be used: A predetermined amount of (a) and (b), the polymerization initiator, and the solvent are loaded into a reaction vessel. For example, a deoxygenated atmosphere is created by replacing oxygen with nitrogen, and the mixture is heated and kept at a constant temperature while stirring. It should be noted that the polymerization initiator and solvent used herein are not particularly limited, and commonly used polymerization initiators and solvents in this field can be used. For example, as polymerization initiators, examples include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylpentanonitrile) etc.) and organic peroxides (benzoyl peroxide, etc.). As solvents, any solvent capable of dissolving the monomers is acceptable; examples include the solvents described later as solvent (E) for the coloring resin composition of the present invention.

[0374] It should be noted that the obtained copolymer can be used directly from the reaction solution, or from a concentrated or diluted solution, or from a substance extracted in solid (powder) form by methods such as reprecipitation. In particular, by using the solvent contained in the coloring resin composition of the present invention as a solvent during the polymerization, the reaction solution can be directly used to prepare the coloring resin composition of the present invention, thus simplifying the manufacturing process of the coloring resin composition of the present invention.

[0375] In resin [K2], the proportions of structural units from each structural unit are preferably 2 to 45 mol% from (a), 2 to 95 mol% from (b), and 1 to 65 mol% from (c), more preferably 5 to 40 mol% from (a), 5 to 80 mol% from (b), and 5 to 60 mol% from (c).

[0376] When the ratio of the structural units of resin [K2] is within the above range, there is a tendency for the coloring resin composition to have excellent storage stability, developability when forming coloring patterns, and solvent resistance, heat resistance and mechanical strength of the obtained color filter.

[0377] Resin [K2] can be manufactured, for example, in the same manner as the method described in the manufacturing method of resin [K1].

[0378] In resin [K3], the ratio of structural units from each structural unit is preferably 2 to 60 mol% from (a) and 40 to 98 mol% from (c) among all structural units constituting resin [K3], more preferably 10 to 50 mol% from (a) and 50 to 90 mol% from (c).

[0379] Resin [K3] can be manufactured, for example, in the same manner as the method described in the manufacturing method of resin [K1].

[0380] The resin [K4] can be manufactured by obtaining a copolymer of (a) and (c) and adding a cyclic ether having 2 to 4 carbon atoms in (b) to a carboxylic acid and / or carboxylic anhydride in (a).

[0381] First, the copolymer of (a) and (c) is manufactured in the same manner as described in the method for manufacturing resin [K1]. In this case, the ratio of the respective structural units is preferably the same as that described in resin [K3].

[0382] Next, the cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a portion of the carboxylic acid and / or carboxylic anhydride from (a) in the copolymer described above.

[0383] After the copolymer of (a) and (c) is produced, the atmosphere inside the flask is replaced with air instead of nitrogen, and (b), a reaction catalyst (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone) are added to the flask. For example, the reaction is carried out at 60 to 130°C for 1 to 10 hours, thereby producing resin [K4].

[0384] The amount of (b) used relative to 100 moles of (a) is preferably 5 to 80 moles, more preferably 10 to 75 moles. Within this range, there is a tendency for a good balance to be achieved in terms of the storage stability of the coloring resin composition, the developability when forming a pattern, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern. Considering the high reactivity of cyclic ethers and the low likelihood of unreacted residues in (b), (b1) is preferred as (b) used in resin [K4], and (b1-1) is even more preferred.

[0385] The amount of the above-mentioned reaction catalyst used is preferably 0.001 to 5 parts by mass relative to the total mass of (a), (b), and (c) 100 parts by mass. The amount of the above-mentioned polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to the total mass of (a), (b), and (c) 100 parts by mass.

[0386] The reaction conditions, such as the feeding method, reaction temperature, and time, can be appropriately adjusted taking into account the manufacturing equipment and the calorific value of polymerization. It should be noted that the feeding method and reaction temperature can be appropriately adjusted, similarly to the polymerization conditions, taking into account the manufacturing equipment and the calorific value of polymerization.

[0387] For resin [K5], as a first stage, copolymers (b) and (c) are obtained in the same manner as resin [K1] described above. Similarly, for the obtained copolymer, the solution after the reaction can be used directly, or a concentrated or diluted solution can be used, or a substance extracted in solid (powder) form using methods such as reprecipitation can be used.

[0388] The ratio of structural units from (b) and (c) relative to the total molar number of all structural units constituting the copolymer is preferably 5-95 mol% from (b) and 5-95 mol% from (c), more preferably 10-90 mol% from (b) and 10-90 mol% from (c).

[0389] Furthermore, under the same conditions as the manufacturing method of resin [K4], the carboxylic acid or carboxylic anhydride contained in (a) is reacted with the cyclic ether from (b) contained in the copolymer of (b) and (c), thereby obtaining resin [K5].

[0390] The amount of (a) used in reaction with the above copolymer is preferably 5 to 80 moles relative to 100 moles of (b). Considering the high reactivity of cyclic ethers and the low likelihood of unreacted residues in (b), (b1) is preferred as (b) for use in resin [K5], and (b1-1) is even more preferred.

[0391] Resin [K6] is a resin obtained by further reacting carboxylic anhydride with resin [K5]. The carboxylic anhydride is reacted with a hydroxyl group generated from the reaction of a cyclic ether with a carboxylic acid or a carboxylic anhydride.

[0392] Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxylic bicyclo[2.2.1]hept-2-ene anhydride. The amount of carboxylic anhydride used is preferably 0.5 to 1 mole relative to the amount used in (a).

[0393] Specific examples of resin (B) include 3,4-epoxycyclohexyl methyl methacrylate / (meth)acrylate copolymer and 3,4-epoxy tricyclic acrylate [5.2.1.0]. 2,6 Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; glycidyl acrylate / benzyl acrylate / (meth)acrylic acid copolymer, glycidyl acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxy tricyclic acrylic acid [5.2.1.0] 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxy tricyclic acrylate [5.2.1.0] 2,6 Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid 2-hydroxyethyl ester copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins obtained by adding glycidyl acrylate to benzyl acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl acrylate to tricyclodecyl acrylate / styrene ... Resins such as those obtained by adding glycidyl acrylate to a copolymer of tricyclodecyl methacrylate / benzyl methacrylate / methacrylic acid [K4]; resins obtained by reacting a copolymer of methacrylic acid and tricyclodecyl methacrylate / glycidyl methacrylate; resins obtained by reacting a copolymer of methacrylic acid and tricyclodecyl methacrylate / styrene / glycidyl methacrylate [K5]; and resins obtained by further reacting a resin obtained by reacting a copolymer of methacrylic acid and tricyclodecyl methacrylate / glycidyl methacrylate with tetrahydrophthalic anhydride [K6].

[0394] The resin (B) is more preferably selected from at least one of resin [K1] and resin [K2], and particularly preferably resin [K2].

[0395] The weight-average molecular weight (Mw) of the polystyrene-converted resin (B) is preferably 1,000 to 100,000, more preferably 2,000 to 50,000, and even more preferably 3,000 to 30,000. When the weight-average molecular weight is within the above range, there is a tendency for the unexposed portion to have high solubility in the developer, as well as for the residual film rate and hardness of the obtained pattern.

[0396] The dispersion of resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1 to 6, more preferably 1.001 to 4, and even more preferably 1.01 to 4.

[0397] The acid value (converted from solids content) of resin (B) is preferably 10 mg-KOH / g to 300 mg-KOH / g, more preferably 20 mg-KOH / g to 250 mg-KOH / g, even more preferably 25 mg-KOH / g to 200 mg-KOH / g, even more preferably 30 mg-KOH / g to 150 mg-KOH / g, and particularly preferably 60 mg-KOH / g to 135 mg-KOH / g. Here, the acid value is determined by measuring the amount (mg) of potassium hydroxide required to neutralize 1 g of resin, and can be obtained, for example, by titration using an aqueous solution of potassium hydroxide.

[0398] The content of resin (B) in 100% by mass of the solid components of the coloring resin composition is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and even more preferably 15 to 30% by mass. When the content of resin (B) is within the above range, there is a tendency for the unexposed portion to have high solubility in the developing solution.

[0399] <Polymerizing Compound (C)>

[0400] The polymerizable compound (C) is a compound that can be polymerized by active free radicals and / or acids generated by a polymerization initiator (D). Examples include compounds with polymerizable olefinic unsaturated bonds, preferably (meth)acrylate compounds.

[0401] Examples of polymeric compounds having one olefinic unsaturated bond include, for example, nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the monomers (a), (b), and (c) described above.

[0402] Examples of polymeric compounds having two olefinic 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.

[0403] The polymerizable compound (C) is preferably a polymerizable compound having three or more olefinic unsaturated bonds. Examples of such polymerizable compounds include, for instance, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, and tri(2-(meth)acryloyloxyethyl... Isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate and caprolactone-modified dipentaerythritol hexa(meth)acrylate, etc., preferably at least one selected from dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0404] The weight-average molecular weight of the polymeric compound (C) is preferably 50 to 4000, more preferably 70 to 3500, even more preferably 100 to 3000, even more preferably 150 to 2900, and particularly preferably 250 to 1500.

[0405] The content of the polymeric compound (C) relative to the total amount of solid components in the coloring resin composition can be, for example, 1% to 99% by mass, preferably 5% to 90% by mass, more preferably 10% to 80% by mass, and even more preferably 12% to 70% by mass.

[0406] <Polymerization Initiator (D)>

[0407] There are no particular limitations on polymerization initiators (D) as long as they are compounds that can generate active free radicals, acids, etc. under the action of light and heat and initiate polymerization. Well-known polymerization initiators can be used.

[0408] Examples of polymerization initiators (D) include O-acyl oxime compounds, alkyl phenyl ketone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0409] Examples of O-acyl oxime compounds include, for instance, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, and N-acetoxy-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 (all of which are manufactured by BASF), N-1919 (manufactured by ADEKA Co., Ltd.) and TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) can also be used as O-acyl oxime compounds. The O-acyl oxime compound is preferably selected from at least one of N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and TR-PBG327 (N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine), and more preferably from at least one of N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and TR-PBG327 (N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine).

[0410] Examples of alkyl phenyl ketone compounds include 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one. Commercially available alkyl phenyl ketone compounds may also be used, such as Irgacure (registered trademark) 369, 907, and 379 (all manufactured by BASF).

[0411] Examples of alkyl phenyl ketone compounds include oligomers of 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzoyladium dimethyl ketal.

[0412] Examples of biimidazole compounds include, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (e.g., see Japanese Patent Application Publication Nos. 6-75372, 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis( Biimidazole compounds with the phenyl group at the 4,4',5,5'-position substituted with a carbonyl alkoxy group, such as 2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (e.g., see Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.) and biimidazole compounds with the phenyl group at the 4,4',5,5'-position substituted with a carbonyl alkoxy group (e.g., see Japanese Patent Application Publication No. 7-10913, etc.).

[0413] 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, and 2,4-bis(trichloromethyl)-6-[2- [5-Methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0414] Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyl diphenylphosphine oxide. Commercially available products such as Irgacure 819 (manufactured by BASF) can be used.

[0415] In addition, examples of polymerization initiators (D) include benzoin compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzoyl ketone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthroquinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzoyl, methyl benzoylformate, and titanium dioxide compounds. These are preferably used in combination with polymerization initiators (D1) (especially amine compounds) described later.

[0416] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds and bimidazole compounds, and more preferably a polymerization initiator containing an O-acyl oxime compound.

[0417] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C) contained in the coloring resin composition. When the content of the polymerization initiator (D) is within the above range, there is a tendency to increase the sensitivity and shorten the exposure time, thereby improving the productivity of the color filter.

[0418] <Polymerization Initiator (D1)>

[0419] The coloring resin composition of the present invention may contain a polymerization initiator (D1). The polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound (C) initiated by a polymerization initiator (D). When containing a polymerization initiator (D1), it is typically used in combination with the polymerization initiator (D).

[0420] Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0421] Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Mischel 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 be used as amine compounds.

[0422] 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.

[0423] Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0424] 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.

[0425] When using these polymerization initiators (D1), their content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C) contained in the coloring resin composition.

[0426] <Solvent (E)>

[0427] Solvent (E) is not particularly limited and solvents commonly used in this field can be used.

[0428] Solvents (E) include, for example, ester solvents (solvents containing -COO- but not -O-), ether solvents (solvents containing -O- but not -COO-), ether-ester solvents (solvents containing both -COO- and -O-), ketone solvents (solvents containing -CO- but not -COO-), alcohol solvents (solvents containing OH- but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. Two or more of these solvents can be used in combination.

[0429] 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.

[0430] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, and 1,4-di(ethylene glycol monomethyl ether). Alkane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether, and methyl anisole, etc.

[0431] 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.

[0432] 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.

[0433] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol.

[0434] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0435] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0436] As a solvent (E), it is preferred to contain at least one solvent selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol and cyclohexanone.

[0437] The content of solvent (E) relative to the total amount of the coloring resin composition is typically 99.99% by mass or less, preferably 40% to 99% by mass, more preferably 50% to 95% by mass, further preferably 70% to 95% by mass, and even more preferably 75% to 90% by mass. In other words, the total amount of solid components in the coloring resin composition is typically 0.01% by mass or more, preferably 1% to 60% by mass, more preferably 5% to 50% by mass, further preferably 5% to 30% by mass, and even more preferably 10% to 25% by mass. When the content of solvent (E) is within the above 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.

[0438] <Leveling Agent (F)>

[0439] Examples of leveling agents (F) include silicone surfactants, fluorinated surfactants, and silicone surfactants containing fluorine atoms. They may have polymerizable groups on their side chains.

[0440] Examples of organosilicon surfactants include surfactants with intramolecular siloxane bonds. Specifically, examples include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (Shin-Etsu Chemical Industry Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (MOMENTIVE PERFORMANCEMATERIALS JAPAN Co., Ltd.).

[0441] As fluorinated surfactants, examples include surfactants with intramolecular fluorocarbon chains. Specifically, examples include FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFACF554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Co., Ltd.), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi Materials Electronics Chemicals Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, and Surflon... SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.), etc.

[0442] Organosilicon surfactants containing fluorine atoms include surfactants with siloxane bonds and fluorocarbon chains within their molecules. Specifically, examples include MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation).

[0443] When leveling agent (F) is included, the content of leveling agent (F) relative to the total amount of the coloring resin composition is preferably 0.0005% to 1% by mass, more preferably 0.001% to 0.5% by mass, and even more preferably 0.005% to 0.1% by mass. It should be noted that this content does not include the content of the dispersant mentioned above. When the content of leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0444] <Other Ingredients>

[0445] The coloring resin composition may contain fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, and other additives known in the art, as needed.

[0446] <Method for manufacturing coloring resin composition>

[0447] Colored resin compositions 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 and conditions.

[0448] The colorant (A) can be used as a solution containing the colorant obtained by pre-mixing it with part 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 as a solution containing the colorant. At this time, part or all of the dispersant and resin (B) described above may also be added as needed. Alternatively, the colorant (A) can also be used as a solution containing the colorant obtained by pre-dissolving part or all of it in the solvent (E). By mixing the remaining components into the solution containing the colorant obtained above to achieve a predetermined concentration, the target colored resin composition can be prepared.

[0449] <Method for Manufacturing Color Filters>

[0450] 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 aforementioned coloring resin composition onto a substrate, drying it to form a coloring resin composition layer, exposing the coloring resin composition layer through a photomask, and then developing it. In photolithography, a color coating film, which is a cured product of the aforementioned coloring resin composition layer, can be formed without using a photomask and / or without development during exposure. The color pattern and color coating film formed in this way constitute the color filter of the present invention.

[0451] The thickness of the filter film is not particularly limited and can be adjusted appropriately according to the purpose and application. For example, it is 0.1μm to 30μm, preferably 0.1μm to 20μm, more preferably 0.5μm to 6μm, and even more preferably 0.8μm to 4.5μm.

[0452] As substrates, various glass plates can be used, such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass with a silica coating, as well as resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, and silicon, or substrates on which aluminum, silver, or silver / copper / palladium alloy thin films are formed. Other color filter layers, resin layers, transistors, and circuits can be formed on these substrates.

[0453] The formation of individual color pixels based on photolithography can be carried out using known or conventional apparatus and conditions. For example, it can be fabricated as described below.

[0454] First, the coloring resin composition is coated onto a substrate and then subjected to heat drying (pre-baking) and / or vacuum drying to remove volatile components such as solvents and dry the substrate, thereby obtaining a smooth coloring resin composition layer.

[0455] Examples of coating methods include spin coating, slot coating, and slot-spindle coating.

[0456] The preferred temperature for heating and drying is 30°C to 120°C, more preferably 50°C to 110°C. The preferred heating time is 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

[0457] When performing vacuum drying, it is preferable to carry out the process at a pressure of 50 Pa to 150 Pa and a temperature range of 20°C to 25°C.

[0458] 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.

[0459] Next, the colored resin composition layer is exposed through a photomask used to form the target colored pattern. The pattern on the photomask is not particularly limited; a pattern corresponding to the intended use is used. Furthermore, in order to uniformly illuminate the entire exposure surface with parallel light and to accurately align the photomask with the substrate on which the colored resin composition layer is formed, exposure apparatus such as a mask aligner and a stepper is preferably used. In the case of forming a colored coating, exposure without a photomask is sufficient.

[0460] As the light source used in exposure, a light source that produces light with wavelengths of 250–450 nm is preferred. For example, light with wavelengths less than 350 nm can be cut off using a filter that cuts off that wavelength region, or light near 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength regions. Specifically, examples include mercury lamps, light-emitting diodes (LEDs), metal halide lamps, and halogen lamps.

[0461] The exposed coloring resin composition layer is brought into contact with a developing solution for development, thereby forming a colored pattern on the substrate. The unexposed portions of the coloring resin composition layer are dissolved and removed by the developing solution. As the developing solution, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% to 10% by mass, more preferably 0.03% to 5% by mass. Furthermore, the developing solution may contain a surfactant. The developing method can be any of the following: paddle method, immersion method, or spray method. Furthermore, the substrate can be tilted at any angle during development. The developed substrate is preferably washed with water.

[0462] Preferably, the obtained colored pattern or colored coating is further subjected to post-baking. The post-baking temperature is preferably 150°C to 250°C, more preferably 160°C to 240°C. The post-baking time is preferably 1 minute to 120 minutes, more preferably 10 minutes to 60 minutes.

[0463] <Display Device>

[0464] The aforementioned color filters are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging elements.

[0465] This application claims the benefit of priority based on Japanese Patent Application No. 2021-078791, filed on May 6, 2021. The entire contents of the description of Japanese Patent Application No. 2021-078791, filed on May 6, 2021, are incorporated herein by reference.

[0466] Example

[0467] The present invention will be described in more detail below with examples. In the examples, unless otherwise specified, the percentages and parts representing the content or amount used are quality standards.

[0468] In the following synthetic examples, the structures of the compounds were confirmed by mass analysis (LC; Agilent 1200, MASS; Agilent LC / MSD6130).

[0469] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin converted from polystyrene were determined by GPC under the following conditions.

[0470] Device: HLC-8120GPC (manufactured by Tosoh Corporation)

[0471] Pillar: TSK-GELG2000HXL

[0472] Column temperature: 40℃

[0473] Solvent: Tetrahydrofuran

[0474] Flow rate: 1.0 mL / min

[0475] The concentration of solid components in the analytical sample was 0.001–0.01% by mass.

[0476] Injection volume: 50 μL

[0477] Detector: RI

[0478] Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0479] The ratio of the weight-average molecular weight to the number-average molecular weight (Mw / Mn) of the polystyrene obtained above is used as the dispersity.

[0480] <Pigment Synthesis>

[0481] [Example 1 of pigment synthesis: Synthesis of compound (B-I-1a)]

[0482] 14.8 parts of 4-bromo-3,5-dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 134 parts of N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were mixed, and 3.2 parts of 60% sodium hydride (manufactured by Kanto Chemical Co., Ltd.) were slowly added, while the temperature was raised to 40°C. 8.0 parts of 1,3,5-tris(bromomethyl)benzene (manufactured by Tokyo Chemical Industry Co., Ltd.) and 34 parts of N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were added dropwise, and the mixture was stirred for 5 hours. After cooling to 10°C, 168 parts of water were added. After heating to 25°C, 168 parts of ethyl acetate (manufactured by Kanto Chemical Co., Ltd.) were added, and the ethyl acetate layer was extracted, concentrated, and dried under reduced pressure at 60°C, yielding 13.4 parts of the compound represented by formula (B-I-1a) (yield 83%).

[0483]

[0484] Determination of the compound represented by formula (B-I-1a)

[0485] (Mass Analysis) Ionization Mode = ESI+: m / z = 715.2

[0486] [Example 2 of pigment synthesis: Synthesis of compound (B-I-1)]

[0487] Ten parts of compound (B-I-1a) obtained in Pigment Synthesis Example 1, 7.0 parts of 1-naphthylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.38 parts of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.7 parts of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.4 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 200 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 93°C for 10 hours. After cooling to 25°C, the resulting mixture was filtered through diatomaceous earth, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, yielding 8.2 parts of the compound represented by formula (B-I-1) (yield 65%).

[0488]

[0489] Determination of the compound represented by formula (B-I-1)

[0490] (Mass Analysis) Ionization Mode = ESI+: m / z = 904.6

[0491] [Example 3 of pigment synthesis: Synthesis of compound (C-I-1a)]

[0492] The following reaction was carried out under a nitrogen atmosphere. 0.27 parts of bis(dibenzylacetone)palladium(O) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.57 parts of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (manufactured by Sigma-Aldrich), 42.1 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 50 parts of 4,4'-dichlorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to a flask equipped with 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 solution was heated to 80°C in an oil bath while being stirred for 2 hours. After cooling the reaction solution in an ice bath, it was filtered to obtain a solid and a filtrate. The solid was designated as crude product A1, and the filtrate as filtrate A1. The obtained crude product A1 was washed with 50 parts toluene, followed by washing twice with 250 parts of deionized water to obtain a solid. This solid was designated as crude product B1. Filtrate A1, 50 parts toluene, 229 parts of deionized water, and 20.8 parts of 35% hydrochloric acid were added to a flask with a bottom outlet and stirred for 1 hour. The mixture was then separated to obtain an organic layer. The obtained organic layer was washed separately with a mixture of 238 parts of deionized water and 12.5 parts of sodium carbonate, dried with 150 parts of magnesium sulfate, and the solid was filtered off. The obtained organic layer was distilled to obtain a solid. This solid was designated as crude product C1. Crude product B1 and crude product C1 were added to a flask equipped with a stirrer, followed by acetonitrile at a mass equal to four times the total mass of crude product B1 and crude product C1. The mixture was stirred for 1 hour. The solid obtained by filtering the mixture was washed with acetonitrile at a mass equal to one times the total mass of crude product B1 and crude product C1. The washed solid was dried under reduced pressure at 60°C to obtain 75.9 parts of the compound represented by formula (C-I-1a). The yield was 90.6%.

[0493]

[0494] [Example 4 of pigment synthesis: Synthesis of compound (C-I-1)]

[0495] The following reaction was carried out under a nitrogen atmosphere. 50 parts of the compound represented by formula (C-I-1a) and 188 parts of N,N-dimethylformamide were added to a flask equipped with a cooling tube and a stirrer, and stirred for 30 minutes while cooling in an ice bath. 40 parts of potassium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the same flask, and stirred further for 1 hour while cooling in an ice bath. 55.6 parts of iodoethane (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise while the reaction solution was kept chilled. The reaction solution was heated to 35°C using an oil bath and stirred for 5 hours, then cooled to room temperature. 1000 parts of a 10% sodium chloride aqueous solution were added dropwise to another flask equipped with a stirrer, and the above reaction solution was added dropwise while stirring. After stirring for 30 minutes, the mixture was filtered to obtain a solid. The obtained solid was washed three times with 500 parts of deionized water and dried at 60°C under reduced pressure to obtain 53.0 parts of the compound represented by formula (C-I-1). Yield: 93.5%.

[0496]

[0497] [Example 5 of pigment synthesis: Synthesis of compound (I-23a-1)]

[0498] The following reaction was carried out under a nitrogen atmosphere. 6.8 parts of the compound represented by formula (B-I-1) obtained in Pigment Synthesis Example 2, 11 parts of the compound represented by formula (C-I-1) obtained in Pigment Synthesis Example 4, and 48 parts of toluene were added to a flask equipped with a cooling tube and a stirring device. Then, 4.6 parts of phosphorus oxychloride (manufactured by Fujifilm and Koko Pure Chemicals Co., Ltd.) were added, and the mixture was stirred at 110°C for 8 hours. The reaction mixture was then cooled to room temperature, and 200 parts of chloroform and 200 parts of saturated brine were added. The aqueous layer was removed by separation. The organic layer was distilled off the solvent using an evaporator, and the resulting blue-violet solid was purified by column chromatography. Further, the resulting blue-violet solid was washed with 100 parts of chloroform and 500 parts of toluene, and then dried under reduced pressure at 60°C to obtain 7.5 parts of the compound represented by formula (I-23a-1) (yield 39%).

[0499]

[0500] Determination of the compound represented by formula (I-23a-1)

[0501] (Mass Analysis) Ionization Mode = ESI+: m / z = 760.6, 3 valence

[0502] [Example 6 of pigment synthesis: Synthesis of compound (I-23a-2)]

[0503] The following reaction was carried out under a nitrogen atmosphere. 4.3 parts of phosphotungstic acid hydrate (Keggin type phosphotungstic acid; manufactured by Sigma-Aldrich) 12 parts of methanol and 7.9 parts of water were added to a flask equipped with a cooling tube and a stirrer, and mixed at 55°C to prepare a phosphotungstic acid solution. 3.0 parts of the compound represented by formula (I-23a-1) obtained in Pigment Synthesis Example 5 were added to the flask, and the mixture was stirred at 55°C for 4 hours. The reaction solution was concentrated, 200 parts of water were added, and after dispersion for 1 hour, it was filtered to obtain a blue solid. Furthermore, 800 parts of methanol were added to the blue solid, and after dispersion for 1 hour, it was filtered and dried under reduced pressure at 60°C to obtain 4.7 parts of the compound represented by formula (I-23a-2) (yield 72%).

[0504]

[0505] Determination of the compound represented by formula (I-23a-2)

[0506] (Mass Analysis) Ionization Mode = MALDI+: m / z = 2280.0

[0507] Ionization mode = MALDI-: m / z = 2902.5

[0508] [Example 7 of pigment synthesis: Synthesis of compound (B-I-2a)]

[0509] 7.4 parts of 4-bromo-3,5-dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 71 parts of N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were mixed, and 1.6 parts of 60% sodium hydride (manufactured by Kanto Chemical Co., Ltd.) were slowly added, while the temperature was raised to 40°C. 4.4 parts of 1,4-bis(bromomethyl)benzene (manufactured by Tokyo Chemical Industry Co., Ltd.) and 18 parts of N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were added dropwise, and the mixture was stirred for 5 hours. After cooling to 10°C, 93 parts of water were added. After heating to 25°C, 93 parts of ethyl acetate (manufactured by Kanto Chemical Co., Ltd.) were added, and the ethyl acetate layer was extracted, concentrated, and dried under reduced pressure at 60°C, yielding 5.1 parts of the compound represented by formula (B-I-2a) (yield 45%).

[0510]

[0511] Determination of the compound represented by formula (B-I-2a)

[0512] (Mass Analysis) Ionization Mode = ESI+: m / z = 503.2

[0513] [Example 8 of pigment synthesis: Synthesis of compound (B-I-2)]

[0514] 9.5 parts of the compound represented by formula (B-I-2a) obtained in Pigment Synthesis Example 7, 7.0 parts of 1-naphthylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.89 parts of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.1 parts of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 5.8 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 190 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 93°C for 10 hours. After cooling to 25°C, the resulting mixture was filtered through diatomaceous earth, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, yielding 7.3 parts of the compound represented by formula (B-I-2) (yield 61%).

[0515]

[0516] Determination of the compound represented by formula (B-I-2)

[0517] (Mass Analysis) Ionization Mode = ESI+: m / z = 629.5

[0518] [Example 9 of pigment synthesis: Synthesis of compound (I-5a-1)]

[0519] The following reaction was carried out under a nitrogen atmosphere. 4.0 parts of the compound represented by formula (B-I-2) obtained in Pigment Synthesis Example 8, 22 parts of the compound represented by formula (C-I-1) obtained in Pigment Synthesis Example 4, and 112 parts of toluene were added to a flask equipped with a cooling tube and a stirrer. Then, 5.9 parts of phosphorus oxychloride (manufactured by Fujifilm and Koko Pure Chemicals Co., Ltd.) were added, and the mixture was stirred at 90°C for 6.5 hours. The reaction mixture was then cooled to room temperature, and 300 parts of chloroform were added. The resulting solution was poured into 3300 parts of ethyl acetate, and the filtered wet solid was washed with ethyl acetate. The resulting solid was dried under reduced pressure at 60°C and purified by column chromatography. Drying under reduced pressure at 60°C yielded 1.0 part of the compound represented by formula (I-5a-1) (yield 10%).

[0520]

[0521] Determination of the compound represented by formula (I-5a-1)

[0522] (Mass Analysis) Ionization Mode = ESI+: m / z = 774.6, 2 valence

[0523] [Example 10 of pigment synthesis: Synthesis of compound (I-5a-2)]

[0524] The following reaction was carried out under a nitrogen atmosphere. 2.0 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Co., Ltd.), 20 parts of dimethyl sulfoxide, and 0.6 parts of the compound represented by formula (I-5a-1) obtained in Pigment Synthesis Example 9 were added to a flask equipped with a cooling tube and a stirrer, and stirred at 45°C for 6 hours. After cooling to 25°C, 80 parts of distilled water were added to the reaction solution, and after dispersion for 1 hour, the mixture was filtered to obtain a blue solid. Then, 60 parts of methanol were added to the blue solid, and after dispersion for 1 hour, the mixture was filtered and dried under reduced pressure at 60°C, resulting in 1.8 parts (quantitative) of the compound represented by formula (I-5a-2).

[0525]

[0526] Determination of the compound represented by formula (I-5a-2)

[0527] (Mass Analysis) Ionization Mode = MALDI+: m / z = 1545.7

[0528] Ionization mode = MALDI-: m / z = 2902.5

[0529] [Example 11 of pigment synthesis: Synthesis of compound (B-I-3a)]

[0530] 4.0 parts of the compound represented by formula (B-I-2a) obtained in Pigment Synthesis Example 7, 4.4 parts of 1-propylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.72 parts of tris(dibenzylacetone)dipalladium(O) (manufactured by Fujifilm and Koko Pure Chemical Co., Ltd.), 0.92 parts of 2-dicyclohexylphosphine-2'-(dimethylamino)biphenyl (manufactured by Fujifilm and Koko Pure Chemical Co., Ltd.), 2.44 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 80 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 40°C for 2 hours. After cooling to 25°C, the resulting mixture was filtered through diatomaceous earth, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, yielding 3.24 parts of the compound represented by formula (B-I-3a) (yield 89%).

[0531]

[0532] Determination of the compound represented by formula (B-I-3a)

[0533] (Mass Analysis) Ionization Mode = ESI+: m / z = 461.5

[0534] [Example 12 of pigment synthesis: Synthesis of compound (B-I-3)]

[0535] 3.0 parts of the compound represented by formula (B-I-3a) obtained in Pigment Synthesis Example 11, 2.70 parts of 1-bromonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.177 parts of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.81 parts of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.01 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 60 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 93°C for 10 hours. After cooling to 25°C, the resulting mixture was filtered through diatomaceous earth, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, yielding 3.45 parts of the compound represented by formula (B-I-3) (yield 74%).

[0536]

[0537] Determination of the compound represented by formula (B-I-3)

[0538] (Mass Analysis) Ionization Mode = ESI+: m / z = 713.6

[0539] [Example 13 of pigment synthesis: Synthesis of compound (I-17a-1)]

[0540] 2.01 parts of the compound represented by formula (C-I-1) obtained in Pigment Synthesis Example 4, 1.35 parts of the compound represented by formula (B-I-3) obtained in Pigment Synthesis Example 12, 0.75 parts of phosphorus oxychloride (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.), and 9.9 parts of dehydrated toluene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 100°C for 3 hours. After cooling to 25°C, the resulting mixture was concentrated. The residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, resulting in 2.31 parts of the compound represented by formula (I-17a-1) (yield 68%).

[0541]

[0542] Determination of the compound represented by formula (I-17a-1)

[0543] (Mass Analysis) Ionization Mode = ESI+: m / z = 815.7, 2 valence

[0544] [Example 14 of pigment synthesis: Synthesis of compound (I-17a-2)]

[0545] 1.95 parts of the compound represented by formula (I-17a-1) obtained in Pigment Synthesis Example 13, 2.91 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Co., Ltd.), and 10.2 parts of dehydrated dimethyl sulfoxide (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 45°C for 6 hours. After cooling to 25°C, 78 parts of water were added, and the resulting blue precipitate was filtered. The residue was dried under reduced pressure at 60°C, yielding 3.3 parts of the compound represented by formula (I-17a-2) (yield 84%).

[0546]

[0547] (Mass Analysis) Ionization Mode = MALDI+: m / z = 1629.6

[0548] Ionization mode = MALDI-: m / z = 2902.5

[0549] [Example 15 of pigment synthesis: Synthesis of compound (B-I-4a)]

[0550] 2.76 parts of the compound represented by formula (B-I-1a) obtained in Pigment Synthesis Example 1, 3.3 parts of 1-propylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.528 parts of tris(dibenzylacetone)dipalladium(O) (manufactured by Fujifilm and Koko Pure Chemical Co., Ltd.), 0.69 parts of 2-dicyclohexylphosphine-2'-(dimethylamino)biphenyl (manufactured by Fujifilm and Koko Pure Chemical Co., Ltd.), 1.77 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 54 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 40°C for 2 hours. After cooling to 25°C, the resulting mixture was filtered through diatomaceous earth, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, resulting in 1.68 parts of the compound represented by formula (B-I-4a) (yield 67%).

[0551]

[0552] Determination of the compound represented by formula (B-I-4a)

[0553] (Mass Analysis) Ionization Mode = ESI+: m / z = 652.6

[0554] [Example 16 of pigment synthesis: Synthesis of compound (B-I-4)]

[0555] 0.82 parts of the compound represented by formula (B-I-4a) obtained in Pigment Synthesis Example 15, 0.91 parts of 1-bromonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.052 parts of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.24 parts of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.59 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 16 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 93°C for 10 hours. After cooling to 25°C, the resulting mixture was filtered through diatomaceous earth, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, yielding 1.2 parts of the compound represented by formula (B-I-4) (yield 87%).

[0556]

[0557] Determination of the compound represented by formula (B-I-4)

[0558] (Mass Analysis) Ionization Mode = ESI+: m / z = 1030.8

[0559] [Example 17 of pigment synthesis: Synthesis of compound (I-35a-1)]

[0560] 1.36 parts of the compound represented by formula (C-I-1) obtained in Pigment Synthesis Example 4, 0.90 parts of the compound represented by formula (B-I-4) obtained in Pigment Synthesis Example 16, 0.52 parts of phosphorus oxychloride (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.), and 6.8 parts of dehydrated toluene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 100°C for 3 hours. After cooling to 25°C, the resulting mixture was concentrated. The residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, resulting in 1.36 parts of the compound represented by formula (I-35a-1) (yield 62%).

[0561]

[0562] Determination of the compound represented by formula (I-35a-1)

[0563] (Mass Analysis) Ionization Mode = ESI+: m / z = 802.7, 3 valence

[0564] [Example 18 of pigment synthesis: Synthesis of compound (I-35a-2)]

[0565] 0.69 parts of the compound represented by formula (I-35a-1) obtained in Pigment Synthesis Example 17, 1.18 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Co., Ltd.), and 3.6 parts of dehydrated dimethyl sulfoxide (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 45°C for 6 hours. After cooling to 25°C, 28 parts of water were added, and the resulting blue precipitate was filtered. The residue was dried under reduced pressure at 60°C, yielding 1.3 parts of the compound represented by formula (I-35a-2) (yield 89%).

[0566]

[0567] Determination of the compound represented by formula (I-35a-2)

[0568] (Mass Analysis) Ionization Mode = MALDI+: m / z = 2405.9

[0569] Ionization mode = MALDI-: m / z = 2902.5

[0570] [Example 19 of pigment synthesis: Synthesis of compound (B-I-5a)]

[0571] The following reaction was carried out under a nitrogen atmosphere. 4.6 parts of 4-bromo-3,5-dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.0 parts of potassium carbonate, and 17.4 parts of N,N-dimethylformamide were added to a flask equipped with a cooling tube and a stirrer. The mixture was stirred at 25°C for 20 minutes, then 2.5 parts of 1,4-dibromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 60°C for 5 hours. After cooling the reaction mixture, 200 parts of distilled water and 200 parts of ethyl acetate were added for separation. The aqueous layer was washed twice with 200 parts of ethyl acetate. The resulting organic layers were dried over excess Na₂SO₄ and concentrated under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (developing phase: hexane / toluene 3 / 1). After drying under reduced pressure at 60°C, 3.7 parts of the compound represented by formula (B-I-5a) were obtained (yield 69%).

[0572]

[0573] Determination of the compound represented by formula (B-I-5a)

[0574] (Mass Analysis) Ionization Mode = ESI+: m / z = 455.2

[0575] [Example 20 of pigment synthesis: Synthesis of compound (B-I-5)]

[0576] 3.95 parts of the compound represented by formula (B-I-5a) obtained in Pigment Synthesis Example 19, 2.48 parts of 1-aminonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.00 parts of tris(dibenzylacetone)dipalladium(O), 0.71 parts of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.74 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 40 parts of toluene were mixed and stirred at 110°C for 3 hours. After cooling to 25°C, the resulting mixture was filtered through diatomaceous earth, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, resulting in 3.5 parts of the compound represented by formula (B-I-5) (yield 70%).

[0577]

[0578] Determination of the compound represented by formula (B-I-5)

[0579] (Mass Analysis) Ionization Mode = ESI+: m / z = 581.5

[0580] [Example 21 of pigment synthesis: Synthesis of compound (C-I-5a)]

[0581] 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 (C-I-5a) was obtained in the same manner as in pigment synthesis example 3.

[0582]

[0583] [Example 22 of pigment synthesis: Synthesis of compound (C-I-5)]

[0584] The compound represented by formula (C-I-5a) was used instead of the compound represented by formula (C-I-1a), and otherwise the compound represented by formula (C-I-5) was obtained in the same manner as in pigment synthesis example 4.

[0585]

[0586] [Example 23 of pigment synthesis: Synthesis of compound (I-40a-1)]

[0587] 16.5 parts of the compound represented by formula (C-I-5) obtained in Pigment Synthesis Example 22, 7.5 parts of the compound represented by formula (B-I-5) obtained in Pigment Synthesis Example 20, 5.9 parts of phosphorus oxychloride (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.), and 98 parts of dehydrated toluene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 80°C for 3 hours. After cooling to 25°C, the resulting mixture was concentrated. The residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, yielding 1.0 part of the compound represented by formula (I-40a-1) (yield 5%).

[0588]

[0589] Determination of the compound represented by formula (I-40a-1)

[0590] (Mass Analysis) Ionization Mode = ESI+: m / z = 777.7, 2 valence

[0591] [Example 24 of pigment synthesis: Synthesis of compound (I-40a-2)]

[0592] 1.3 parts of the compound represented by formula (I-40a-1) obtained in Pigment Synthesis Example 23, 3.8 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Co., Ltd.), and 6.6 parts of dehydrated dimethyl sulfoxide (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 45°C for 6 hours. After cooling to 25°C, 80 parts of water were added, and the resulting blue precipitate was filtered. The residue was dried under reduced pressure at 60°C, yielding 1.4 parts of the compound represented by formula (I-40a-2) (yield 61%).

[0593]

[0594] Determination of the compound represented by formula (I-40a-2)

[0595] (Mass Analysis) Ionization Mode = MALDI+: m / z = 1553.7

[0596] Ionization mode = MALDI-: m / z = 2902.5

[0597] [Example 25 of pigment synthesis: Synthesis of compound (C-I-6a)]

[0598] Using 2,6-dimethyl-4-methoxyaniline instead of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), the compound represented by formula (C-I-6a) was obtained in the same manner as in Pigment Synthesis Example 3.

[0599]

[0600] [Example 26 of pigment synthesis: Synthesis of compound (C-I-6)]

[0601] The compound represented by formula (C-I-6a) was used instead of the compound represented by formula (C-I-1a), and otherwise the compound represented by formula (C-I-6) was obtained in the same manner as in pigment synthesis example 4.

[0602]

[0603] [Example 27 of pigment synthesis: Synthesis of compound (I-42a-1)]

[0604] 4.7 parts of the compound represented by formula (C-I-6) obtained in Pigment Synthesis Example 26, 2.0 parts of the compound represented by formula (B-I-5) obtained in Pigment Synthesis Example 20, 1.6 parts of phosphorus oxychloride (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.), and 6.0 parts of dehydrated toluene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 80°C for 4 hours. After cooling to 25°C, the resulting mixture was concentrated. The residue was purified by silica gel column chromatography (solvent: chloroform) and dried under reduced pressure at 60°C, yielding 0.7 parts of the compound represented by formula (I-42a-1) (yield 10%).

[0605]

[0606] Determination of the compound represented by formula (I-42a-1)

[0607] (Mass Analysis) Ionization Mode = ESI+: m / z = 809.7, 2 valence

[0608] [Example 28 of pigment synthesis: Synthesis of compound (I-42a-2)]

[0609] 0.7 parts of the compound represented by formula (I-42a-1) obtained in Pigment Synthesis Example 27, 1.8 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Co., Ltd.), and 210 parts of dehydrated dimethyl sulfoxide (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 45°C for 6 hours. After cooling to 25°C, 300 parts of water were added, and the resulting blue precipitate was filtered. The residue was dried under reduced pressure at 60°C, yielding 0.7 parts of the compound represented by formula (I-42a-2) (yield 57%).

[0610]

[0611] Determination of the compound represented by formula (I-42a-2)

[0612] (Mass Analysis) Ionization Mode = MALDI+: m / z = 1617.7

[0613] Ionization mode = MALDI-: m / z = 2902.5

[0614] [Example 29 of pigment synthesis: Synthesis of compound (I-4a-1)]

[0615] The compound represented by formula (C-I-5) was used instead of the compound represented by formula (C-I-1), otherwise the compound represented by formula (I-4a-1) was obtained in the same manner as in pigment synthesis example 9.

[0616]

[0617] Determination of the compound represented by formula (I-4a-1)

[0618] (Mass Analysis) Ionization Mode = MALDI+: m / z = 1601.9

[0619] [Example 30 of pigment synthesis: Synthesis of compound (I-4a-2)]

[0620] The compound represented by formula (I-4a-1) was used instead of the compound represented by formula (I-5a-1), and otherwise the compound represented by formula (I-4a-2) was obtained in the same manner as in pigment synthesis example 10.

[0621]

[0622] Determination of the compound represented by formula (I-4a-2)

[0623] (Mass Analysis) Ionization Mode = MALDI+: m / z = 1601.9

[0624] Ionization mode = MALDI-: m / z = 2902.5

[0625] [Example 31 of pigment synthesis: Synthesis of compound (x1)]

[0626] The compound represented by the following formula (x1) was synthesized according to the contents disclosed in Japanese Patent Application Publication No. 2014-108975.

[0627]

[0628] [Example 32 of pigment synthesis: Synthesis of compound (x2)]

[0629] The compound represented by the following formula (x2) was synthesized according to the contents disclosed in Japanese Patent Application Publication No. 2014-108975.

[0630]

[0631] <Resin Synthesis>

[0632] Resin Synthesis Example 1

[0633] A suitable amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen. 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were then added, and the mixture was heated to 85°C while stirring. Next, 38 parts of acrylic acid and 3,4-epoxytricyclic acrylic acid [5.2.1.0] were added dropwise over 5 hours. 2,6 ] Decane-8-yl ester and 3,4-epoxy tricyclic acrylate [5.2.1.0] 2,6 A mixed solution of 25 parts of decane-9-yl ester (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 prepared. On the other hand, a solution was prepared by dropwise addition of 5 parts of 2,2-azobisisobutyronitrile to 88 parts of propylene glycol monomethyl ether acetate over 6 hours. After the addition was completed, the solution was maintained at 85°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-1) solution with a viscosity of 23 mPas and a solid content of 25.6%, as measured by a type B viscometer (23°C). The weight-average molecular weight (Mw) of the resulting copolymer was 8.0 × 10⁻⁶. 3 The dispersion is 2.1, and the acid value converted from solid components is 109 mg-KOH / g.

[0634] Resin B-1 has the following structural units.

[0635]

[0636] [Example 1]

[0637] <Preparation of colorant dispersion (A-1) containing compound (I-23a-2)>

[0638] Five parts of compound (I-23a-2), three parts of acrylic dispersant, two parts of resin B-1 (solid component 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 (LAU). The zirconia beads were then removed by filtration to obtain the colorant dispersion (A-1).

[0639] <Preparation of Coloring Resin Compositions>

[0640] The following components are mixed to obtain a colored resin composition.

[0641]

[0642]

[0643] [Examples 2-7, Comparative Examples 1-2]

[0644] By changing compound (I-23a-2) to the following compounds, the colored resin compositions were obtained in the same manner as in Example 1.

[0645] Example 2: Compound (I-5a-2)

[0646] Example 3: Compound (I-17a-2)

[0647] Example 4: Compound (I-35a-2)

[0648] Example 5: Compound (I-40a-2)

[0649] Example 6: Compound (I-42a-2)

[0650] Example 7: Compound (I-4a-2)

[0651] Comparative Example 1: Compound (x1)

[0652] Comparative Example 2: Compound (x2)

[0653] <Preparation example 1>

[0654] (Preparation of the red resin composition)

[0655] The following components are mixed to obtain a red resin composition.

[0656]

[0657]

[0658] <Formation of Colored Coating Film (Color Filter)>

[0659] The colored resin compositions obtained in Examples 1-7 and Comparative Examples 1-2, and the red resin composition obtained in Preparation Example 1, were respectively spin-coated onto 2-inch square glass substrates (EAGLE 2000; manufactured by Corning Corporation) and pre-baked at 100°C for 3 minutes to form composition layers. After cooling, they were exposed to atmospheric pressure at 60 mJ / cm² using an exposure machine (TME-150RSK; manufactured by TOPCON Corporation). 2 After irradiating the composition layer with light at an exposure level (365nm reference), it is baked in an oven at 230°C for 20 minutes to obtain a colored coating film.

[0660] <Determination of Transmission Spectroscopy>

[0661] The transmission spectra of the colored coatings obtained in Examples 1 to 7, Comparative Examples 1 to 2, and Preparation Example 1 were measured using an Olympus colorimeter (OSP-SP-200).

[0662] <Calculation of brightness>

[0663] The CIE chromaticity coordinates and luminance Y were determined when the coloring 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 luminance Y were calculated using the transmission spectra obtained from the coloring coatings of Examples 1-7 and Comparative Examples 1-2, the transmission spectrum obtained from the coloring coating of Preparation Example 1, and the characteristic function of the C light source. The mixing ratios in Table 10 are combinations of CIE chromaticity coordinates (x, y) = (0.150, 0.060). The values ​​of luminance Y are shown in Table 10. A higher Y value indicates higher luminance.

[0664] [Table 10]

[0665]

[0666] In Table 10, each symbol represents the following colorant.

[0667] I-23a-2: Compound (I-23a-2)

[0668] I-5a-2: Compound (I-5a-2)

[0669] I-17a-2: Compound (I-17a-2)

[0670] I-35a-2: Compound (I-35a-2)

[0671] I-40a-2: Compound (I-40a-2)

[0672] I-42a-2: Compound (I-42a-2)

[0673] I-4a-2: Compound (I-4a-2)

[0674] x1: Compound (x1)

[0675] x2: Compound (x2)

[0676] AR52: Acid Red 52

Claims

1. The compound represented by formula (I), In formula (I), R 1 and R 3 The phenyl groups, which may or may not have at least one substituent selected from alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms, are independently represented. R 2 and R 4 Represents saturated chain hydrocarbon groups with 1 to 10 carbon atoms. R 13 Represents saturated chain hydrocarbon groups or hydrogen atoms with 1 to 6 carbon atoms. R 5 ~R 12 Represents a hydrogen atom. T 1 This indicates a divalent aromatic hydrocarbon group, and the aromatic hydrocarbon ring constituting this aromatic hydrocarbon group represents a naphthalene ring, or a structure obtained by substituting at least one hydrogen atom of the naphthalene ring with a saturated chain hydrocarbon group having 1 to 4 carbon atoms. T 2 This indicates a divalent aromatic hydrocarbon group, and the aromatic hydrocarbon ring constituting this aromatic hydrocarbon group represents a benzene ring, or a structure obtained by substituting at least one hydrogen atom of the benzene ring with a saturated chain hydrocarbon group having 1 to 4 carbon atoms. L 1 It is an α-valent aliphatic hydrocarbon group with 1 to 8 carbon atoms, and at least one of the methylene groups contained in the aliphatic hydrocarbon group is substituted with -O-, or it is a group shown in (i2), or it is a group shown in (i3). 'a' represents 2 or 3. b and c represent integers greater than 1 independently. d represents an integer greater than or equal to 0. X c- This refers to the C-valent anion of heteropolyacids or isopolyacids containing tungsten as an essential element. In equations (i2) and (i3), L i2 ~L i3 Each of these groups independently represents an alkane diene with 1 to 5 carbon atoms, wherein one of the methylene groups in the alkane diene is substituted with -O-. * indicates a group with T. 2 The bonding sites.

2. A coloring resin composition comprising a colorant and a resin, wherein the colorant comprises the compound of claim 1.

3. The coloring resin composition according to claim 2, wherein, It further contains polymerizable compounds and polymerization initiators.

4. A color filter formed from the coloring resin composition of claim 2 or 3.

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

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