Compounds and colored resin compositions

Abstract

The present application aims to provide a compound having a large molar absorption coefficient at a maximum absorption wavelength (λmax) in the range of 600 to 750 nm and good stability before and after post-baking when a color filter is produced. The present application relates to a compound represented by formula (I). [In formula (I), Z 1 and Z 2 each independently represents a group represented by formula (i). R 3 represents a hydrocarbon group which can have a substituent, an aromatic heterocyclic group which can have a substituent, or a group formed by combining a hydrocarbon group which can have a substituent and an aromatic heterocyclic group which can have a substituent, and -CH2- contained in the hydrocarbon group can be replaced with -O-, -CO-, -NR 6 -, -S-, -SO-, or -SO2-.][In formula (i), R 7 represents a hydrogen atom, a hydrocarbon group which can have a substituent, or a group represented by formula (ii). a1 represents 0 or 1.]

Description

TECHNICAL FIELD

[0001] The present application relates to a compound, a colored resin composition, a color filter, and a display device. BACKGROUND

[0002] A color filter used in a display device such as a liquid crystal display device, an electroluminescence display device, and a plasma display, a solid-state imaging element such as a CCD and a CMOS sensor is manufactured from a colored resin composition. As a colorant for the above-mentioned colored resin composition, an aluminum phthalocyanine pigment is known. Patent Literature 1 describes that an aluminum phthalocyanine pigment having a specific structure as a colorant is used, thereby providing a colorant composition for a color filter, which is high in brightness when used in a color filter, and is excellent not only in NMP (N-methylpyrrolidone) resistance but also in development property and flatness of a coating film.

[0003] PRIOR ART DOCUMENTS

[0004] PATENT LITERATURE

[0005] Patent Literature 1: Japanese Patent Application Laid-Open No. 2016-75837 SUMMARY

[0006] However, the aluminum phthalocyanine pigment described in Patent Literature 1 sometimes has a small molar absorption coefficient at an absorption maximum wavelength (λmax) in the range of 600 to 750 nm, and is low in stability before and after post-baking when a color filter is produced. Therefore, an object of the present application is to provide a novel compound which has a large molar absorption coefficient at an absorption maximum wavelength in the range of 600 to 750 nm, and is excellent in stability before and after post-baking when a color filter is produced.

[0007] The present application includes the following inventions.

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

[0009]

[0010] [In the formula (I),

[0011] X 1 ~ X 8 each independently represents -R 4 , -OR 4 , -SR 4 , a halogen atom, a nitro group, or an aminosulfonyl group which can have a substituent.

[0012] R 4 represents a hydrocarbon group having 1 to 20 carbon atoms which can have a substituent.

[0013] Each of n1 to n8 independently represents an integer of 0 to 4.

[0014] Z 1 and Z 2 each independently represents a group represented by formula (i).

[0015] R 3 represents a hydrocarbon group which can have a substituent, an aromatic heterocyclic group which can have a substituent, or a group formed by combining a hydrocarbon group which can have a substituent and an aromatic heterocyclic group which can have a substituent, and -CH2- contained in the hydrocarbon group can be replaced with -O-, -CO-, -NR 6 -, -S-, -SO-, or -SO2-.

[0016] R 6 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0017]

[0018] [in formula (i),

[0019] R 7 represents a hydrogen atom, a hydrocarbon group which can have a substituent, or a group represented by formula (ii).

[0020] a1 represents 0 or 1.

[0021] * represents a bonding site.

[0022]

[0023] [in formula (ii),

[0024] X 9 to X 12 each independently represents -R 5 , -OR 5 , -SR 5 , a halogen atom, a nitro group, or an amino sulfonyl group which can have a substituent.

[0025] R 5 represents a hydrocarbon group having 1 to 20 carbon atoms which can have a substituent.

[0026] n9 to n12 each independently represent an integer of 0 to 4.

[0027] * represents a bonding site.

[0028] [2] A colored resin composition comprising the compound according to [1] and a resin.

[0029] [3] The colored resin composition according to [2], wherein a polymerizable compound and a polymerization initiator are contained.

[0030] [4] A color filter formed from the colored resin composition described in [2] or [3].

[0031] [5] A display device comprising the color filter described in [4].

[0032] According to the present application, a novel compound having a large molar absorption coefficient at a maximum absorption wavelength in the range of 600 to 750 nm can be provided, and in addition, in a color filter formed from a colored resin composition containing the novel compound, good stability before and after post-baking can be achieved. DETAILED DESCRIPTION

[0033] <Compound>

[0034] Hereinafter, the present application will be described in more detail with reference to partial structures of the compound represented by Formula (I). According to the novel compound represented by Formula (I) according to the present application, the molar absorption coefficient at a maximum absorption wavelength in the range of 600 to 750 nm is large, and in addition, in a color filter formed from a colored resin composition containing the compound, good stability before and after post-baking can be achieved. Furthermore, the novel compound represented by Formula (I) is preferably thermally stable.

[0035]

[0036] [In Formula (I),

[0037] X 1 ~ X 8 each independently represents -R 4 , -OR 4 , -SR 4 , a halogen atom, a nitro group, or an aminosulfonyl group which can have a substituent.

[0038] R 4 represents a hydrocarbon group having 1 to 20 carbon atoms which can have a substituent.

[0039] n1 to n8 each independently represent an integer of 0 to 4.

[0040] Z 1 and Z 2 each independently represents a group represented by Formula (i).

[0041] R 3 represents a hydrocarbon group which can have a substituent, an aromatic heterocyclic group which can have a substituent, or a group formed by combining a hydrocarbon group which can have a substituent and an aromatic heterocyclic group which can have a substituent, -CH2- contained in the hydrocarbon group can be replaced with -O-, -CO-, -NR 6 , -S-, -SO-, or -SO2-.

[0042] R6 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0043]

[0044] [In formula (i),

[0045] R 7 represents a hydrogen atom, a hydrocarbon group which can have a substituent, or a group represented by formula (ii).

[0046] a1represents 0 or 1.

[0047] * indicates a bonding site.

[0048]

[0049] [In formula (ii),

[0050] X 9 ~ X 12 each independently represents -R 5 , -OR 5 , -SR 5 , a halogen atom, a nitro group, or an aminosulfonyl group which can have a substituent.

[0051] R 5 represents a hydrocarbon group having 1 to 20 carbon atoms which can have a substituent.

[0052] n9to n12each independently represent an integer of 0 to 4.

[0053] * indicates a bonding site.

[0054] R 4 and R 5 represent a hydrocarbon group having 1 to 20 carbon atoms which can have a substituent.

[0055] R 4 and R 5 represent a hydrocarbon group having 1 to 20 carbon atoms which can have a substituent. The hydrocarbon group having 1 to 20 carbon atoms represented by R

[0056] As the saturated or unsaturated chain hydrocarbon group represented by R 4 and R 5 , straight chain alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, and an n-icosyl group;

[0057] isopropyl, isobutyl, sec-butyl, t-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, 1,1,3,3- tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1,1- dimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, 2-propylpentyl, 1- ethyl- 1,2-dimethylpropyl, 1-methylpentyl, 4-methylpentyl, 4-methylhexyl, 5- methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1- ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1- propylheptyl, and 1-butylhexyl, and the like branched alkyl groups;

[0058] vinyl (vinyl), propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1-methyl-1-butenyl, 3-methyl-2-butenyl, 1,3-butadienyl, 3-methyl-1,2-butadienyl, 1-(2-propenyl)vinyl, 1-(1-methylvinyl)vinyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, pentenyl (e.g., 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl), 1-(1,1-dimethylethyl)vinyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), decenyl (e.g., 1-decenyl, 9-decenyl), undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosan-1-ol, and the like alkenyl groups;

[0059] Acetylenyl group, propynyl group (e.g., 1-propynyl group, 2-propynyl group), butynyl group (e.g., 1-butynyl group, 2-butynyl group, 3-butynyl group), pentynyl group (e.g., 2-pentynyl group, 3-pentynyl group, 4-pentynyl group), 1-methyl-3-butynyl group, 1,1-dimethyl-2-propynyl group, hexynyl group (e.g., 2-hexynyl group, 5-hexynyl group), 1-ethyl-3-butynyl group, heptynyl group (e.g., 2-heptynyl group, 6-heptynyl group), 1-ethyl-3-pentynyl group, octynyl group (e.g., 1-octynyl group, 2-octynyl group, 7-octynyl group), nonynyl group (e.g., 2-nonynyl group, 8-nonynyl group), decynyl group (e.g., 2-decynyl group, 9-decynyl group), undecynyl group, dodecynyl group, tridecynyl group, tetradecynyl group, pentadecynyl group, hexadecynyl group, heptadecynyl group, octadecynyl group, nonadecynyl group, and icosynyl group, and the like.

[0060] R 4 and R 5 The number of carbon atoms of the saturated chain hydrocarbon group (i.e., straight-chain alkyl group, branched-chain alkyl group) represented by R

[0061] R 4 and R 5 The number of carbon atoms of the unsaturated chain hydrocarbon group (i.e., alkenyl group, alkynyl group) represented by R

[0062] As the saturated or unsaturated alicyclic hydrocarbon group represented by R 4 and R 5 The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group represented by R

[0063] Cyclohexenyl group (e.g., cyclohex-1-en-1-yl group, cyclohex-2-en-1-yl group, cyclohex-3-en-1-yl group), cycloheptenyl group, and cyclooctenyl group, and the like.

[0064] Norbornyl group, norbornenyl group, adamantyl group, bicyclo[2.2.2]octyl group, and the like.

[0065] R 4 and R 5 The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 10.

[0066] As R 4 and R 5 Examples of aromatic hydrocarbon groups that can be represented include: phenyl, 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, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 3,5-di(tert-butyl)phenyl, 3,5-di(tert-butyl)-4-methylphenyl. 4-Butylphenyl, 4-pentylphenyl, 2,6-bis(1-methylethyl)phenyl, 2,4,6-tris(1-methylethyl)phenyl, 4-cyclohexylphenyl, 2,4,6-trimethylphenyl, 4-octylphenyl, 4-(1,1,3,3-tetramethylbutyl)phenyl, 1-naphthyl, 2-naphthyl, 6-methyl-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthraceneyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, perylyl, Aromatic hydrocarbon groups such as hydroxyl and pyrene.

[0067] R 4 and R 5 The aromatic hydrocarbon group represented preferably has 6 to 20 carbon atoms, more preferably 6 to 10, and even more preferably 6 to 8.

[0068] R 4 and R 5 The hydrocarbon group can be a group formed by combining the hydrocarbon groups mentioned above (e.g., at least one of aromatic hydrocarbon groups and chain hydrocarbon groups and alicyclic hydrocarbon groups), for example:

[0069] Benzyl, (2-methylphenyl)methyl, (3-methylphenyl)methyl, (4-methylphenyl)methyl, (2-ethylphenyl)methyl, (3-ethylphenyl)methyl, (4-ethylphenyl)methyl, (2-(tert-butyl)phenyl)methyl, (3-(tert-butyl)phenyl)methyl, (4-(tert-butyl)phenyl)methyl, (3,5-dimethylphenyl)methyl, 1-phenylethyl, 1-methyl-1-phenylethyl, 1,1-diphenylethyl, (1-naphthyl)methyl and (2-naphthyl)methyl, etc., aralkyl groups;

[0070] 1-phenylvinyl, 2-phenylvinyl (phenylvinyl), 2,2-diphenylvinyl, 2-phenyl-2-(1-naphthyl)vinyl, and the like arylalkenyl groups;

[0071] phenylacetylenyl, 3-phenyl-2-propynyl, and the like arylalkynyl groups;

[0072] a phenyl group in which one or more phenyl groups are bonded;

[0073] cyclohexylmethylphenyl, benzylphenyl, (dimethyl(phenyl)methyl)phenyl, and the like.

[0074] The number of carbon atoms of these is preferably from 7 to 18, more preferably from 7 to 15.

[0075] R 4 and R 5 The alkyl group in which one or more alicyclic hydrocarbon groups are bonded, represented by R

[0076] The number of carbon atoms of these is preferably from 4 to 15, more preferably from 4 to 10.

[0077] R 4 and R 5 The alkyl group in which one or more alicyclic hydrocarbon groups are bonded, represented by R

[0078] The alkyl group in which one or more alicyclic hydrocarbon groups are bonded, represented by R 4 and R 5 The substituent of the alkyl group having from 1 to 20 carbon atoms, represented by R a1 , -OR a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 , and -NR a1 R a2 , and the like.

[0079] Here, R a1 and R a2 each independently represent a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms. As the alkyl group having from 1 to 20 carbon atoms, represented by R a1 and R a2 , the same groups as those exemplified for R 4 and R 5This refers to the same group as the hydrocarbon group with 1 to 20 carbon atoms. As R a1 and R a2 Each of them independently prefers hydrogen atoms, saturated chain hydrocarbon groups with 1 to 10 carbon atoms, or aromatic hydrocarbon groups with 6 to 10 carbon atoms.

[0080] As R 4 and R 5 The heterocyclic group used as a substituent for the hydrocarbon group with 1 to 20 carbon atoms can be a monocyclic or polycyclic ring, and is preferably a heterocyclic ring containing a heteroatom as a constituent element of the ring. Examples of heteroatoms include nitrogen atoms, oxygen atoms, and sulfur atoms.

[0081] Examples of heterocycles containing only nitrogen atoms as heteroatoms include: monocyclic saturated heterocycles such as aziridine, aziridine butane, pyrrolidine, piperidine, and piperazine; five-membered unsaturated heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, and 1,2,4-triazole; six-membered unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, and 1,3,5-triazine; fused bicyclic heterocycles such as indazole, indoline, isoindazolin, isoindazolin-1,3-dione, indole, inazine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, terpinen, phthalazine, naphthidine, purine, pteridine, benzopyrazole, and benzopiperidine; and fused tricyclic heterocycles such as carbazole, acridine, and phenazine.

[0082] Examples of heterocycles containing only oxygen atoms as heteroatoms include: oxetane, oxetane, tetrahydrofuran, tetrahydropyran, and 1,3-dioxane. Alkane, 1,4-di Monocyclic saturated heterocycles such as alkanes; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; lactone heterocycles such as α-acetyl lactone, β-propiolactone, γ-butyrolactone, and δ-valerolactone; five-membered unsaturated heterocycles such as furans; six-membered unsaturated heterocycles such as 2H-pyran and 4H-pyran; 1-benzofuran, benzopyran, and benzodioxane. Fused bicyclic heterocycles such as benzodioxole, chromane, and isochromane; fused tricyclic heterocycles such as xanthones and dibenzofurans.

[0083] Examples of heterocycles containing only sulfur atoms as heteroatoms include: saturated five-membered rings such as dithiopentane; saturated six-membered rings such as thiane and 1,3-dithiane; unsaturated five-membered rings such as thiophene; unsaturated six-membered rings such as 4H-thiaran; fused bicyclic heterocycles such as benzothiaran and benzothiaphene; and fused tricyclic heterocycles such as thiaanthracene and dibenzothiaphene.

[0084] As the heterocycle containing a nitrogen atom and an oxygen atom as heteroatoms, there can be mentioned a monocyclic saturated heterocycle such as morpholine, 2-pyrrolidone, 2-piperidone, and the like; monocyclic unsaturated heterocycle such as oxazole, isoxazole, and the like; monocyclic unsaturated heterocycle such as oxazole, isoxazole, and the like; monocyclic unsaturated heterocycle such as oxazole, isoxazole, and the like; monocyclic unsaturated heterocycle such as oxazole, isoxazole, and the like; monocyclic unsaturated heterocycle such as oxazole, isoxazole, and the like; fused bicyclic heterocycle such as benzimidazoline, and the like; and a heterocycle containing a nitrogen atom and a sulfur atom as heteroatoms. fused bicyclic heterocycle such as benzimidazoline, and the like; and a heterocycle containing a nitrogen atom and a sulfur atom as heteroatoms.

[0085] As the heterocycle containing a nitrogen atom and a sulfur atom as heteroatoms, there can be mentioned a monocyclic heterocycle such as thiazole; a fused bicyclic heterocycle such as benzothiazole; a fused tricyclic heterocycle such as phenothiazine; and the like.

[0086] The number of carbon atoms of the heterocycle group is preferably from 2 to 30, more preferably from 3 to 22, and further preferably from 3 to 20.

[0087] The heterocycle group can have a substituent, and as the substituent, there can be mentioned a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a nitro group; a cyano group; -OR a1 , -CO2R a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 , and -NR a1 R a2 (wherein R a1 and R a2 are the same as described above).

[0088] Note that the bonding position of the heterocycle is a moiety after the dissociation of any hydrogen atom contained in each ring.

[0089] As the halogen atom used for the substituent of the hydrocarbon group represented by R 4 and R 5 having a number of carbon atoms of 1 to 20, there can be mentioned a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and the like.

[0090] As the halogen atom represented by X 1 to X 12 , there can be mentioned a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and the like, and a fluorine atom is preferred.

[0091] The aminosulfonyl group represented by X 1 to X 12 is represented by -SO2-NH2(* represents the bonding site).

[0092] X 1 to X12 The aminosulfonyl group can have substituents. As X 1 ~X 12 Examples of substituents representing the aminosulfonyl group include hydrocarbon groups with 1 to 20 carbon atoms that can have substituents, heterocyclic groups that can have substituents, halogen atoms such as fluorine, chlorine, bromine, and iodine atoms, nitro, cyano, and -OR groups. a1 -CO2R a1 、-SR a1 -SO2R a1 -SO3R a1 -SO2NR a1 R a2 and -NR a1 R a2 etc. (where R) a1 and R a2 Same as above).

[0093] For X 1 ~X 12 The substituents representing the aminosulfonyl group are hydrocarbon groups with 1 to 20 carbon atoms, and examples of R can be cited. 4 and R 5 The group exemplified is a hydrocarbon group with 1 to 20 carbon atoms. For X 1 ~X 12 The substituents representing the aminosulfonyl group are hydrocarbon groups with 1 to 20 carbon atoms, preferably saturated chain hydrocarbon groups with 1 to 10 carbon atoms, or aromatic hydrocarbon groups with 6 to 10 carbon atoms, more preferably saturated chain hydrocarbon groups with 1 to 4 carbon atoms, or aromatic hydrocarbon groups with 6 to 8 carbon atoms.

[0094] This hydrocarbon group can have substituents. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, as well as nitro, cyano, and -OR groups. a1 -CO2R a1 、-SR a1 -SO2R a1 -SO3R a1 -SO2NR a1 R a2 and -NR a1 R a2 etc. (where R) a1 and R a2 Same as above).

[0095] As X 1 ~X 12 The heterocyclic group used as the substituent for the aminosulfonyl group can be monocyclic or polycyclic, and is preferably a heterocycle containing a heteroatom as a constituent element of the ring. Examples of heteroatoms include nitrogen atoms, oxygen atoms, and sulfur atoms.

[0096] As the heterocycle, a heterocycle exemplified as the substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R 4 and R 5 The heterocycle represented by R

[0097] The number of carbon atoms of the heterocycle is preferably 2 to 30, more preferably 3 to 22, and further preferably 3 to 20.

[0098] The heterocycle can have a substituent, and as the substituent, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a nitro group; a cyano group; -OR a1 , -CO2R a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 , and -NR a1 R a2 (wherein R a1 and R a2 are the same as described above) can be exemplified.

[0099] Note that the bonding position of the heterocycle is a portion after the dissociation of an arbitrary hydrogen atom contained in each ring.

[0100] X 1 to X 8 represent -R 4 and X 9 to X 12 represent -R 5 The aliphatic hydrocarbon group having 1 to 20 carbon atoms is preferred, the saturated chain hydrocarbon group having 1 to 20 carbon atoms is more preferred, the saturated chain hydrocarbon group having 1 to 10 carbon atoms is further preferred, and the branched alkyl group having 1 to 5 carbon atoms is still further preferred, and a tert-butyl group is particularly preferred.

[0101] X 1 to X 8 represent -OR 4 and -SR 4 , and X 9 to X 12 represent -OR 5 and -SR 5 R 4 and R 5 each independently are preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and further preferably a linear or branched alkyl group having 1 to 5 carbon atoms or an aromatic hydrocarbon group having 6 to 8 carbon atoms.

[0102] Z 1 and Z 2 each independently represents a group represented by formula (i). In the compound represented by formula (I), Z 1 and Z 2 may be the same or different, and preferably are the same group.

[0103]

[0104] [In formula (i),

[0105] R 7 represents a hydrogen atom, a hydrocarbon group which can have a substituent, or a group represented by formula (ii).

[0106] a1represents 0 or 1.

[0107] * represents a bonding site.

[0108] R 7 The number of carbon atoms of the hydrocarbon group represented by R

[0109] As the hydrocarbon group represented by R 7 , the same groups as exemplified for the hydrocarbon group represented by R 4 and R 5 having 1 to 20 carbon atoms. That is, as the hydrocarbon group represented by R 7 , there can be mentioned linear or branched alkyl groups, alkenyl groups, alkynyl groups and the like chain hydrocarbon groups; alicyclic hydrocarbon groups such as cycloalkyl groups, cycloalkenyl groups, saturated or unsaturated polycyclic hydrocarbon groups; aromatic hydrocarbon groups; groups formed by combining at least one of aromatic hydrocarbon groups, chain hydrocarbon groups and alicyclic hydrocarbon groups with an aromatic hydrocarbon group; chain hydrocarbon groups and alicyclic hydrocarbon groups and the like.

[0110] R 7 The hydrocarbon group represented by R a1 may have a substituent, and as the substituent, there can be mentioned heterocyclic groups which can have a substituent, halogen atoms, nitro groups, cyano groups, -OR a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 , -NR a1 R a2 and the like (wherein R a1 and R a2 are the same as described above).

[0111] As R 7The heterocyclic group used as a substituent of the hydrocarbon group represented by R

[0112] As the heterocyclic group, the same heterocyclic group as that used as a substituent of the hydrocarbon group represented by R 4 and R 5 The heterocyclic group used as a substituent of the hydrocarbon group represented by R

[0113] The number of carbon atoms of the heterocyclic group is preferably from 2 to 30, more preferably from 3 to 22, and further preferably from 3 to 20.

[0114] The heterocyclic group can have a substituent, and as the substituent, there can be mentioned halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, a nitro group, a cyano group, -OR a1 , -CO2R a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 , and -NR a1 R a2 (and the like (wherein R a1 and R a2 are the same as described above).

[0115] Note that the bonding position of the heterocyclic group is a moiety after the dissociation of any hydrogen atom contained in each ring.

[0116] As the halogen atom used as a substituent of the hydrocarbon group represented by R 7 , there can be mentioned a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0117] The number of carbon atoms of the hydrocarbon group represented by R 3 is preferably from 1 to 30, more preferably from 1 to 20, and further preferably from 2 to 20.

[0118] The hydrocarbon group represented by R 3 is a divalent hydrocarbon group, and as the hydrocarbon group, there can be mentioned an aliphatic hydrocarbon group and an aromatic hydrocarbon group, and the aliphatic hydrocarbon group can be a chain hydrocarbon group and an alicyclic hydrocarbon group. In addition, a hydrocarbon group formed by combining two or more of these groups can also be mentioned.

[0119] As the chain hydrocarbon group, there can be mentioned an alkandiyl group, an alkenediyl group, an alkynediyl group and the like.

[0120] As the alkanediyl group, there are mentioned methylene, ethylene, propane-1, 3-diyl, butane-1, 4-diyl, pentane-1, 5-diyl, hexane-1, 6-diyl, heptane-1, 7-diyl, octane-1, 8-diyl, nonane-1, 9-diyl, decane-1, 10-diyl, undecane-1, 11-diyl, dodecane-1, 12-diyl and the like straight-chain alkanediyl group;

[0121] ethane-1, 1-diyl, propane-1, 1-diyl, propane-1, 2-diyl, propane-2, 2-diyl, pentane-2, 4-diyl, 2-methylpropane-1, 3-diyl, 2-methylpropane-1, 2-diyl, pentane-1, 4-diyl, 2-methylbutane-1, 4-diyl and the like branched-chain alkanediyl group.

[0122] The number of carbon atoms of the alkanediyl group is preferably from 1 to 20, more preferably from 1 to 10.

[0123] As the alkenediyl group, there are mentioned ethene-1, 1-diyl, ethene-1, 2-diyl, propene-1, 2-diyl, propene-1, 3-diyl, propene-2, 3-diyl, 1-butene-1, 2-diyl, 1-butene-1, 3-diyl, 1-butene-1, 4-diyl, 1-pentene-1, 5-diyl, 2-pentene-1, 5-diyl, 1-hexene-1, 6-diyl, 3-hexene-1, 6-diyl, 1-heptene-1, 7-diyl, 1-octene-1, 8-diyl, 1-nonene-1, 9-diyl, 1-decene-1, 10-diyl and the like.

[0124] The number of carbon atoms of the alkenediyl group is preferably from 2 to 20, more preferably from 2 to 10.

[0125] As the alkynediyl group, there are mentioned ethyne-1, 2-diyl, 1-propyne-1, 3-diyl, 1-butyne-1, 4-diyl, 2-butyn-1, 4-diyl, 1-pentyn-1, 5-diyl, 1-hexyn-1, 6-diyl, 1-heptyn-1, 7-diyl, 1-octyn-1, 8-diyl, 1-nonyn-1, 9-diyl, 1-decyn-1, 10-diyl and the like.

[0126] The number of carbon atoms of the alkynediyl group is preferably from 2 to 20, more preferably from 2 to 10.

[0127] As the alicyclic hydrocarbon group, there are mentioned:

[0128] cyclobutane-1, 3-diyl, cyclopentane-1, 3-diyl, cyclohexane-1, 4-diyl, cyclooctane-1, 5-diyl and the like cycloalkanediyl group;

[0129] cyclohexene-3, 6-diyl and the like cycloalkenediyl group.

[0130] polycyclic hydrocarbon groups such as adamantane-1, 5-diyl, adamantane-2, 6-diyl, and the like.

[0131] The number of carbon atoms of the alicyclic hydrocarbon group is preferably from 3 to 18, more preferably from 3 to 16, and further preferably from 3 to 12.

[0132] As the aromatic hydrocarbon group, there are mentioned, for example:

[0133] 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, and the like;

[0134] 1,4-naphthalene, 2,6-naphthalene, and the like;

[0135] 1,4-anthracene, 1,8-anthracene, and the like;

[0136] biphenyl-4, 2'-diyl, biphenyl-4, 3'-diyl, biphenyl-4, 4'-diyl, and the like;

[0137] 2,7-phenanthrene, 9, 10-phenanthrene, and the like;

[0138] fluorene-2, 7-diyl, and the like.

[0139] Further, the aromatic hydrocarbon group also includes a group in which a hydrogen atom bonded to an aromatic hydrocarbon ring constituting the aromatic hydrocarbon group is substituted with an alkyl group (preferably an alkyl group having from 1 to 8 carbon atoms, and more preferably an alkyl group having from 1 to 4 carbon atoms) such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a t-butyl group, an n-hexyl group, a 2-ethylhexyl group, and the like. As the above-mentioned group in which a hydrogen atom bonded to an aromatic hydrocarbon ring constituting the aromatic hydrocarbon group is substituted with an alkyl group, there are mentioned, for example, 4-alkyl-1, 3-phenylene, 2-alkyl-1, 4-phenylene, 2, 5-dialkyl-1, 4-phenylene, 2, 6-dialkyl-1, 4-phenylene, 9, 9-dialkylfluorene-2, 7-diyl, and the like.

[0140] The number of carbon atoms of the aromatic hydrocarbon group is preferably from 6 to 20, and more preferably from 6 to 15.

[0141] As the hydrocarbon group formed by combining two or more kinds, there are mentioned, for example, a group formed by combining a chain hydrocarbon group with an alicyclic hydrocarbon group and / or an aromatic hydrocarbon group, and the like. In the combination, the chain hydrocarbon group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group can each be two or more kinds.

[0142] As the hydrocarbon group formed by combining two or more kinds, for example, there are -alicyclic hydrocarbon group-chain hydrocarbon group-, -chain hydrocarbon group-alicyclic hydrocarbon group-, -chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, -chain hydrocarbon group-aromatic hydrocarbon group-, -aromatic hydrocarbon group-chain hydrocarbon group-, -chain hydrocarbon group-aromatic hydrocarbon group-chain hydrocarbon group-, -aromatic hydrocarbon group-chain hydrocarbon group-aromatic hydrocarbon group-, -chain hydrocarbon group-aromatic hydrocarbon group-chain hydrocarbon group-aromatic hydrocarbon group-chain hydrocarbon group-, and the like. Note that * indicates the bonding site to the phosphorus atom to which Z 1 is bonded, and ** indicates the bonding site to the phosphorus atom to which Z 2 is bonded.

[0143] When the number of carbon atoms of the above hydrocarbon group is two or more and -CH2- is contained, the -CH2- contained in the hydrocarbon group can be substituted with -O-, -CO-, -NR 6 -, -S-, -SO-, or -SO2-. The number of -CH2- substituted with -O-, -CO-, -NR 6 -, -S-, -SO-, or -SO2- is not particularly limited and can be one or plural. However, when the hydrocarbon group is constituted only of an alkanediyl group, not all -CH2- is substituted with -O-, -CO-, -NR 6 -, -S-, -SO-, or -SO2-.

[0144] As the alkyl group represented by R 6 having 1 to 4 carbon atoms, there are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a t-butyl group, and the like.

[0145] R 3 The hydrocarbon group represented by R

[0146] The substituent of the hydrocarbon group represented by R 3 may be a monocyclic or polycyclic aromatic heterocyclic group.

[0147] As the aromatic heterocycle, there are a pyrrole ring, a pyrazole ring, an imidazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, an indole ring, a benzimidazole ring, a quinoline ring, an isoquinoline ring, and the like as nitrogen-containing aromatic heterocycles containing only a nitrogen atom as a heteroatom; a furan ring, a benzofuran ring, and the like as oxygen-containing aromatic heterocycles containing only an oxygen atom as a heteroatom; a thiophene ring, a benzothiophene ring, and the like as sulfur-containing aromatic heterocycles containing only a sulfur atom as a heteroatom; an oxazole ring, a benzoxazole ring, and the like as aromatic heterocycles containing a nitrogen atom and an oxygen atom as heteroatoms; a thiazole ring, a benzothiazole ring, and the like as aromatic heterocycles containing a nitrogen atom and a sulfur atom as heteroatoms; and the like. ​

[0148] The aromatic heterocyclic group can have a substituent, and as the substituent, halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a nitro group; a cyano group; -OR a1 a1 a1 a1 a1 a1 a2 a1 a2 (wherein R a1 and R a2 are the same as described above) can be mentioned.

[0149] Note that the bonding position of the aromatic heterocyclic group is a moiety after the dissociation of any hydrogen atom contained in each ring.

[0150] As the halogen atom used as the substituent of the hydrocarbon group represented by R 3 , a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and the like can be mentioned.

[0151] The aromatic heterocyclic group represented by R 3 is a divalent aromatic heterocyclic group and a moiety remaining after the removal of two hydrogen atoms directly bonded to atoms constituting a ring from an aromatic heterocyclic ring.

[0152] The above-described aromatic heterocyclic group can be a monocyclic ring or a polycyclic ring, and for example, the following can be mentioned:

[0153] a pyrrole ring, a pyrazole ring, an imidazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, an indole ring, a benzimidazole ring, a quinoline ring, an isoquinoline ring, and the like, which are nitrogen-containing aromatic heterocyclic rings containing only nitrogen atoms as heteroatoms;

[0154] a furan ring, a benzofuran ring, and the like, which are oxygen-containing aromatic heterocyclic rings containing only oxygen atoms as heteroatoms;

[0155] a thiophene ring, a benzothiophene ring, and the like, which are sulfur-containing aromatic heterocyclic rings containing only sulfur atoms as heteroatoms;

[0156] an oxazole ring, and the like, which are sulfur-containing aromatic heterocyclic rings containing nitrogen atoms and oxygen atoms as heteroatoms;

[0157] a thiazole ring, a benzothiazole ring, and the like, which are aromatic heterocyclic rings containing nitrogen atoms and sulfur atoms as heteroatoms, and the like.

[0158] The bonding position of the aromatic heterocyclic group is a moiety after the dissociation of any two hydrogen atoms contained in each ring.

[0159] R 3 ​​​​​​​​The aromatic heterocyclic group can have substituents. Examples of substituents include hydrocarbon groups with 1 to 20 carbon atoms, halogen atoms, nitro groups, and cyano groups.

[0160] For R 3 The aromatic heterocyclic substituents used are hydrocarbon groups with 1 to 20 carbon atoms, and examples of substituents as R are given. 4 and R 5 The groups exemplified are hydrocarbon groups with 1 to 20 carbon atoms. For R... 3 The substituents of the aromatic heterocyclic group are hydrocarbon groups with 1 to 20 carbon atoms, preferably saturated chain hydrocarbon groups with 1 to 10 carbon atoms or aromatic hydrocarbon groups with 6 to 10 carbon atoms, more preferably saturated chain hydrocarbon groups with 1 to 4 carbon atoms or aromatic hydrocarbon groups with 6 to 8 carbon atoms.

[0161] This hydrocarbon group can have substituents. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, as well as nitro, cyano, and -OR groups. a1 -CO2R a1 、-SR a1 -SO2R a1 -SO3R a1 -SO2NR a1 R a2 and -NR a1 R a2 etc. (where R) a1 and R a2 Same as above).

[0162] For R 3 The halogen atom used in the substituents of the aromatic heterocyclic group can be exemplified by fluorine, chlorine, bromine, and iodine atoms.

[0163] As a group formed by combining a hydrocarbon group that can have substituents with an aromatic heterocyclic group that can have substituents, examples include the R group described above. 3 The indicated hydrocarbon group that can have substituents is related to the above-mentioned R. 3 This indicates a group that can be formed by combining aromatic heterocyclic groups with substituents. In this combination, there can be two or more hydrocarbon groups and aromatic heterocyclic groups.

[0164] As a group in which a hydrocarbon group which can have a substituent and an aromatic heterocyclic group which can have a substituent are combined, for example, the following can be given: *-a hydrocarbon group which can have a substituent-a aromatic heterocyclic group which can have a substituent-**, *-a aromatic heterocyclic group which can have a substituent-a hydrocarbon group which can have a substituent-**, *-a hydrocarbon group which can have a substituent-a aromatic heterocyclic group which can have a substituent-a hydrocarbon group which can have a substituent-**, *-a aromatic heterocyclic group which can have a substituent-a hydrocarbon group which can have a substituent-a aromatic heterocyclic group which can have a substituent-**, *-a hydrocarbon group which can have a substituent-a aromatic heterocyclic group which can have a substituent-a hydrocarbon group which can have a substituent-a aromatic heterocyclic group which can have a substituent-**, and the like, of which *-a hydrocarbon group which can have a substituent-a aromatic heterocyclic group which can have a substituent-** is preferred, *-a chain hydrocarbon group which can have a substituent-a aromatic heterocyclic group which can have a substituent-a chain hydrocarbon group which can have a substituent-** is more preferred. Note that * indicates the bonding site to the phosphorus atom to which Z 1 is bonded, ** indicates the bonding site to the phosphorus atom to which Z 2 is bonded.

[0165] X 1 ~ X 8 each independently is preferably -R 4 , -OR 4 , or a halogen atom, more preferably a saturated chain hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or a halogen atom, further preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom, more further preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms or a halogen atom.

[0166] n1 to n8 are each independently preferably an integer of 0 to 2, more preferably 0 or 1.

[0167] X 9 ~ X 12 each independently is preferably -R 5 , -OR 5 , or a halogen atom, more preferably a saturated chain hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or a halogen atom, further preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom, more further preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms or a halogen atom.

[0168] n9 to n12 are each independently preferably an integer of 0 to 2, more preferably 0 or 1.

[0169] R 7Preferably, it is a hydrogen atom, a group represented by formula (ii), or a hydrocarbon group having 1 to 20 carbon atoms that may have substituents; more preferably, it is a hydrogen atom, a group represented by formula (ii), or an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have substituents; even more preferably, it is a hydrogen atom, a group represented by formula (ii), or an aromatic hydrocarbon group having 6 to 10 carbon atoms that may have substituents; and particularly preferably, it is a hydrogen atom, a group represented by formula (ii), or a phenyl group that may have substituents.

[0170] In particular, when a1 is 0, R 7 Preferably, it is a hydrocarbon group having 1 to 20 carbon atoms that may have a substituent; more preferably, it is an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have a substituent; and even more preferably, it is an aromatic hydrocarbon group having 6 to 10 carbon atoms that may have a substituent.

[0171] Additionally, when a1 is 1, R 7 Preferably, it is a hydrogen atom, a group represented by formula (ii), or a hydrocarbon group having 1 to 20 carbon atoms that may have substituents; more preferably, it is a hydrogen atom, a group represented by formula (ii), or an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have substituents; and even more preferably, it is a hydrogen atom, a group represented by formula (ii), or an aromatic hydrocarbon group having 6 to 10 carbon atoms that may have substituents.

[0172] a1 is preferably 1.

[0173] R 3 Preferred is *-R 31 -** or *-O-R 31 -O-** indicates a group. R 31 This indicates a hydrocarbon group that may have substituents, an aromatic heterocyclic group that may have substituents, or a group composed of a hydrocarbon group that may have substituents and an aromatic heterocyclic group that may have substituents, wherein the -CH2- group contained in the hydrocarbon group may be replaced by -O-, -CO-, or -NR. 6 -, -S-, -SO-, or -SO2-. However, the -CH2- at the end of the bonding site is not replaced by -O-, -CO-, or -NR. 6 -, -S-, -SO-, or -SO2-, R 31 When composed solely of alkyl dienes, not all -CH2- are substituted with -O-, -CO-, or -NR. 6 -, -S-, -SO-, or -SO2-. It should be noted that * indicates the same as Z. 1 The bonding sites of the phosphorus atoms, ** indicate the bonding sites with Z. 2 The bonding sites of the phosphorus atoms that are bonded.

[0174] R 31hydrocarbon group which can have a substituent, an aromatic heterocyclic group which can have a substituent, and a group formed by combining a hydrocarbon group which can have a substituent with an aromatic heterocyclic group which can have a substituent, and the like. 3 hydrocarbon group which can have a substituent, an aromatic heterocyclic group which can have a substituent, and a group formed by combining a hydrocarbon group which can have a substituent with an aromatic heterocyclic group which can have a substituent, and the like.

[0175] hydrocarbon group which can have a substituent, an aromatic heterocyclic group which can have a substituent, and a group formed by combining a hydrocarbon group which can have a substituent with an aromatic heterocyclic group which can have a substituent, and the like. 31 ,

[0176] hydrocarbon group which can have a substituent, an aromatic heterocyclic group which can have a substituent, and a group formed by combining a hydrocarbon group which can have a substituent with an aromatic heterocyclic group which can have a substituent, and the like.

[0177] hydrocarbon group which can have a substituent, an aromatic heterocyclic group which can have a substituent, and a group formed by combining a hydrocarbon group which can have a substituent with an aromatic heterocyclic group which can have a substituent, and the like.

[0178] hydrocarbon group which can have a substituent, an aromatic heterocyclic group which can have a substituent, and a group formed by combining a hydrocarbon group which can have a substituent with an aromatic heterocyclic group which can have a substituent, and the like.

[0179] In the above preferable mode, the number of carbon atoms of the chain hydrocarbon group is preferably from 1 to 10, more preferably from 2 to 8.

[0180] In the above preferable mode, the aromatic hydrocarbon group is preferably phenylene or biphenylene.

[0181] In the above preferable mode, -CH2- contained in the hydrocarbon group (preferably, chain hydrocarbon group) can be substituted with -O-, -CO-, -NR 6 -, -S-, -SO-, or -SO2-, but -CH2- at the end of the bonding site is not substituted with -O-, -CO-, -NR 6 -, -S-, -SO-, or -SO2-, R 31 When composed only of an alkane diyl group, not all -CH2- is substituted with -O-, -CO-, -NR 6 -, -S-, -SO-, or -SO2-.

[0182] hydrocarbon group which can have a substituent, an aromatic heterocyclic group which can have a substituent, and a group formed by combining a hydrocarbon group which can have a substituent with an aromatic heterocyclic group which can have a substituent, and the like.31 chain hydrocarbon group represented by formula (1-1) to formula (1-23). In formula (1-1) to formula (1-23), R 6 * represents a bonding site.

[0183]

[0184] as the aromatic hydrocarbon group in R 31 is phenylene or biphenylene, and more preferably 1,3-phenylene, 1,4-phenylene, or biphenyl-4,4'-diyl.

[0185] as the aromatic hydrocarbon group in R 31 chain hydrocarbon group which can have a substituent - aromatic hydrocarbon group which can have a substituent - chain hydrocarbon group which can have a substituent -, preferably a group represented by formula (2-1) or formula (2-2), and more preferably a group represented by formula (2-2).

[0186]

[0187] [In formula (2-1) and (2-2),

[0188] T 1 represents phenylene which can have an alkyl group as a substituent, biphenylene which can have an alkyl group as a substituent, or fluorene-diyl which can have an alkyl group as a substituent.

[0189] R 32 and R 33 each independently represents an alkanediyl group having 1 to 10 carbon atoms.

[0190] * represents a bonding site.

[0191] as T 1 from the viewpoint of further improving stability before and after post-baking, preferably phenylene which can have an alkyl group as a substituent or fluorene-diyl which can have an alkyl group as a substituent.

[0192] The number of carbon atoms of the alkyl group as the substituent is preferably 1 to 8, more preferably 1 to 4, and further preferably a methyl group or an ethyl group. The number of alkyl groups bonded to phenylene, biphenylene, or fluorene-diyl is not particularly limited as long as it is the number of substitutable groups, and is preferably 1 to 4, and more preferably 1 or 2.

[0193] as R 32 to R 33The alkanediyl group having 1 to 10 carbon atoms represented by the formula (2-1) can be exemplified by the groups having 1 to 10 carbon atoms among the groups described above as the straight-chain alkanediyl group and the branched-chain alkanediyl group. Among them, the straight-chain alkanediyl group having 1 to 10 carbon atoms is preferred, and the straight-chain alkanediyl group having 1 to 4 carbon atoms is more preferred.

[0194] R 32 R 33 may be the same or different, and are preferably the same.

[0195] As the group represented by the formula (2-1), for example, the groups represented by the formulae (2-1-1) to (2-1-12) can be exemplified, and as the group represented by the formula (2-2), for example, the groups represented by the formulae (2-2-1) to (2-2-16) can be exemplified.

[0196]

[0197]

[0198] As the aromatic hydrocarbon group which can have a substituent in R 31 may be the same or different, and are preferably the same.

[0199]

[0200] [In the formulae (3-1) and (3-2),

[0201] T 2 and T 3 each independently represents a phenylene group which can have an alkyl group as a substituent or a biphenylene group which can have an alkyl group as a substituent.

[0202] R 34 represents an alkanediyl group having 1 to 10 carbon atoms.

[0203] * represents a bonding site.

[0204] As T 2 and T 3 , a phenylene group which can have an alkyl group as a substituent is preferred.

[0205] The number of carbon atoms of the alkyl group as the substituent is preferably 1 to 8, more preferably 1 to 4, and further preferably a methyl group or an ethyl group. The number of the alkyl groups bonded to the phenylene group or the biphenylene group is not particularly limited as long as it is the number of substitutable groups, respectively, and is preferably 1 to 4, and more preferably 1 or 2.

[0206] As R 34The alkyl diene with 1 to 10 carbon atoms can be exemplified by groups with 1 to 10 carbon atoms described above as straight-chain alkyl dienes and branched-chain alkyl dienes. Among these, straight-chain alkyl dienes with 1 to 10 carbon atoms are preferred, and straight-chain alkyl dienes with 1 to 4 carbon atoms are more preferred.

[0207] Examples of groups represented by formula (3-1) include those represented by formulas (3-1-1) to (3-1-9), and examples of groups represented by formulas (3-2) to (3-2-7) include those represented by formulas (3-2-1) to (3-2-7).

[0208]

[0209]

[0210] As R 31 The * in the formula is a chain hydrocarbon group that may have a substituent, an aromatic heterocyclic group that may have a substituent, and a chain hydrocarbon group that may have a substituent. The * is preferably a group represented by formula (4-1) or formula (4-2), and more preferably a group represented by formula (4-2).

[0211]

[0212] In equations (4-1) and (4-2),

[0213] T 4 It represents a nitrogen-containing aromatic heterocycle.

[0214] R 35 and R 36 Each can independently represent an alkyl diol with 1 to 10 carbon atoms.

[0215] * indicates a bonding site.

[0216] As R 35 ~R 36 The alkyl diene with 1 to 10 carbon atoms can be exemplified by groups with 1 to 10 carbon atoms described above as straight-chain alkyl dienes and branched-chain alkyl dienes. Among these, straight-chain alkyl dienes with 1 to 10 carbon atoms are preferred, and straight-chain alkyl dienes with 1 to 4 carbon atoms are more preferred.

[0217] R 35 With R 36 They can be the same or different, but the same is preferred.

[0218] As T 4 The nitrogen-containing aromatic heterocycle represented is preferably a pyridine ring.

[0219] As the group represented by formula (4-1), for example, there can be mentioned the groups represented by formulae (4-1-1) to (4-1-3), and as the group represented by formula (4-2), for example, there can be mentioned the groups represented by formulae (4-2-1) to (4-2-4).

[0220]

[0221] wherein, as the group represented by -R 31 -** and -O-R 31 R in the group represented by -O-** 31 , preferably -CH2- can be replaced with -O-, -CO-, -NR 6 - or -S-, an aromatic hydrocarbon group which can have a substituent, or -an aromatic hydrocarbon group which can have a substituent-an aromatic hydrocarbon group which can have a substituent-, more preferably a group represented by formulae (1-1) to (1-23), a phenylene group which can have a substituent, a biphenylene group which can have a substituent, a group represented by formula (2-1), or a group represented by formula (2-2), further preferably a group represented by formulae (1-1) to (1-23), a phenylene group which can have a substituent, a group represented by formula (2-1), or a group represented by formula (2-2).

[0222] As R 6 , preferably a hydrogen atom.

[0223] As the compound represented by formula (I), for example, there can be mentioned the compounds represented by formulae (I-a1) to (I-a3) in which Z 1A , Z 2A and R 3A are the groups shown in Tables 1 to 5 below.

[0224] Hereinafter, the compounds having the groups shown as No. 1 to 305 in Tables 1 to 5 in formula (I-a1) will be referred to as compounds (I-a1-1) to (I-a1-305), respectively.

[0225] Further, the compounds having the groups shown as No. 1 to 305 in Tables 1 to 5 in formula (I-a2) will be referred to as compounds (I-a2-1) to (I-a2-305), respectively.

[0226] Further, the compounds having the groups shown as No. 1 to 305 in Tables 1 to 5 in formula (I-a3) will be referred to as compounds (I-a3-1) to (I-a3-305), respectively.

[0227]

[0228] [Table 1]

[0229]

[0230] [Table 2]

[0231]

[0232] [Table 3]

[0233]

[0234] [Table 4]

[0235]

[0236] [Table 5]

[0237]

[0238] In Tables 1 to 5, z1 to z5 each correspond to a group represented by the following formulae (z1) to (z5), and r1 to r19 each correspond to a group represented by the following formulae (r1) to (r19).

[0239]

[0240] [In formulae (z1) to (z5), * indicates a bonding site with a phosphorus atom.]

[0241]

[0242] [In formulae (r1) to (r19), * indicates a bonding site with a phosphorus atom to which Z 1A is bonded, and ** indicates a bonding site with a phosphorus atom to which Z 2A is bonded.]

[0243] As the compound represented by formula (I), compounds (I-a1-1) to (I-a1-48), compounds (I-a1-173) to (I-a1-181), compounds (I-a1-185) to (I-a1-203), compounds (I-a1-260) to (I-a1-278), compounds (I-a1-302) to (I-a1-303), compounds (I-a2-1) to (I-a2-48), compounds (I-a2-173) to (I-a2-181), compounds (I-a3-1) to (I-a3-48), compounds (I-a3-173) to (I-a3-181), more preferably compounds (I-a1-1) to (I-a1-16), compounds (I-a1-173) to (I-a1-175), compound (I-a1-181), compound (I-a1-203), compound (I-a1-278), compounds (I-a2-1) to (I-a2-16), compounds (I-a2-173) to (I-a2-175), compound (I-a2-181), compounds (I-a3-1) to (I-a3-16), compounds (I-a3-173) to (I-a3-175), compound (I-a3-181) are preferable.

[0244] As the method for producing the compound represented by formula (I), for example, the following methods (i) to (iv) can be mentioned. The following methods (i) to (iv) are only one example of the method for producing the compound represented by formula (I), and publicly known reactions can be appropriately combined.

[0245] [Method (i)]

[0246] For R 3 -O-R 31 The compound (I') in which the group represented by -O-** is converted into a hydroxyl group to synthesize the compound represented by formula (IV), and then the resulting compound represented by formula (IV), the compound represented by formula (V-1), and the compound represented by formula (V-2) are appropriately reacted, whereby the target compound is obtained. i The compound (I') in which the group represented by -O-** is converted into a hydroxyl group to synthesize the compound represented by formula (IV), and then the resulting compound represented by formula (IV), the compound represented by formula (V-1), and the compound represented by formula (V-2) are appropriately reacted, whereby the target compound is obtained.

[0247]

[0248] In the above formula, X i represents a halogen atom, X 1 ~X 8 , n1 to n8, Z 1 ~Z2 and R 31 represent the same meaning as described above.

[0249] a plurality of X i may be the same or different. As X i , a chlorine atom is preferred.

[0250] [Method (ii)]

[0251] In the case where R 3 is a group represented by *-O-R 31 -O-**, R 31 is a group represented by the above-mentioned formula (2-2), for example, a compound represented by formula (VII-1) and a compound represented by formula (VII-2) are synthesized by appropriately reacting a compound represented by formula (II-1) and a compound represented by formula (VI-1), and a compound represented by formula (II-2) and a compound represented by formula (VI-2), respectively. Subsequently, a halogen atom X i of the compounds represented by formula (VII-1) and formula (VII-2) is converted to a hydroxyl group, respectively, to synthesize a compound represented by formula (VIII-1) and formula (VIII-2). By using the compounds represented by formula (VIII-1) and formula (VIII-2), and a compound represented by formula (IX) to perform a Sonogashira coupling reaction, a compound represented by formula (X) is synthesized, and by appropriately reacting the compound represented by formula (X), a compound represented by formula (V-1), and a compound represented by formula (V-2), a target compound can be obtained.

[0252]

[0253] In the above formula, X ii represents a halogen atom, X i , X 1 ~ X 8 , n1~n8, Z 1 ~ Z 2 , T 1 and R 32 ~ R 33 represent the same meaning as described above.

[0254] a plurality of X ii may be the same or different. As X ii , an iodine atom is preferred.

[0255] [Method (iii)]

[0256] In the case where R 3 is a group represented by *-O-R 31 -O-**, R 31In the case of the compound (I'") represented by the above-described formula (3-2), for example, the compound represented by the formula (II-1) and the compound represented by the formula (XI-1), the compound represented by the formula (II-2) and the compound represented by the formula (XI-2) are respectively reacted to synthesize the compound represented by the formula (XII-1) and the compound represented by the formula (XII-2). Subsequently, the halogen atom X i is respectively converted into a hydroxyl group to synthesize the compound represented by the formula (XIII-1) and the compound represented by the formula (XIII-2). By using the obtained compound represented by the formula (XIII-1) and the compound represented by the formula (XIII-2), and the compound represented by the formula (XIV), a Sonogashira coupling reaction is performed to synthesize the compound represented by the formula (XV), and the compound represented by the formula (XV), the compound represented by the formula (V-1) and the compound represented by the formula (V-2) are appropriately reacted, whereby the target compound can be obtained.

[0257]

[0258] In the above formula, X iii represents a halogen atom, X i , X 1 ~ X 8 , n1~n8, Z 1 ~ Z 2 , T 2 ~ T 3 and R 34 represent the same meanings as described above.

[0259] As X iii , a iodine atom is preferred.

[0260] [Method (iv)]

[0261] R 3 is a group represented by *-R 31 **. The compound (I'") represented by the above-described formula (3-2) is obtained, for example, by appropriately reacting the compound represented by the formula (XVI), the compound represented by the formula (V-1) and the compound represented by the formula (V-2).

[0262]

[0263] In the above formula, X 1 ~ X 8 , n1~n8, Z 1 ~ Z 2 and R 31 represent the same meanings as described above.

[0264] <<Colored resin composition>>

[0265] The colored resin composition of the present application contains the above-mentioned compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)) and a resin (hereinafter, sometimes referred to as resin (B)). The colored resin composition of the present application preferably contains the above-mentioned compound (I) as a colorant (hereinafter, sometimes referred to as colorant (A)).

[0266] The colored resin composition of the present application preferably further contains a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D)).

[0267] The colored resin composition of the present application preferably further contains a solvent (hereinafter, sometimes referred to as solvent (E)).

[0268] The colored resin composition of the present application can contain a leveling agent (hereinafter, sometimes referred to as leveling agent (F)).

[0269] In the present specification, the compounds exemplified as each component can be used alone or in combination of a plurality of kinds, unless otherwise specified.

[0270] <colorant (A)>

[0271] The colored resin composition of the present application contains compound (I) as colorant (A). The content rate of compound (I) is preferably 0.5 to 70 mass%, more preferably 1 to 55 mass%, further preferably 2 to 50 mass%, particularly preferably 5 to 40 mass% or 8 to 40 mass%, in the total amount of solid components in the colored resin composition.

[0272] Note that the "total amount of solid components" in the present specification means the total amount of components obtained by removing the solvent from the colored resin composition of the present application. The total amount of solid components and the content of each component with respect to the total amount can be measured, for example, using a publicly known analysis method such as liquid chromatography or gas chromatography.

[0273] In addition, the content rate of compound (I) is preferably 20 to 100 mass%, more preferably 30 to 100 mass%, further preferably 40 to 100 mass%, in the total amount of colorant (A). In addition, the content rate of compound (I) can be 60 mass% or more, can be 80 mass% or more, or can be 90 mass% or more, in the total amount of colorant (A).

[0274] Colorant (A) can further contain a colorant (hereinafter, sometimes referred to as colorant (A2)) different from compound (I).

[0275] Colorant (A2) can be any one of a dye and a pigment.

[0276] As the dye, for example, a compound classified as a substance having a color tone other than pigments in the Color Index (published by The Society of Dyers and Colourists), a well-known dye described in the Dyeing Guide (Saiden Co., Ltd.) can be mentioned. Xanthene dyes are particularly preferable.

[0277] The xanthene dye is a dye containing a compound having a xanthene skeleton in the molecule. As the xanthene dye, for example, C.I. Acid Red 51 (hereinafter, the description of C.I. Acid Red is omitted, and only the number is described, and the same applies to the other), 52, 87, 92, 94, 289, 388, C.I. Acid Violet 9, 30, 102, C.I. Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, 11, C.I. Basic Violet 10 (Rhodamine B), 11, C.I. Solvent Red 218, C.I. Mordant Red 27, C.I. Reactive Red 36 (Bengal Rose B), xanthene dyes described in Japanese Patent Application Laid-Open No. 2010-32999, and xanthene dyes described in Patent No. 4492760, and the like can be mentioned. A dye that dissolves in an organic solvent is preferable.

[0278] The xanthene dye can use a commercially available xanthene dye (for example, "Chugai Aminol Fast Pink R-H / C" manufactured by Chugai Pharmaceutical Co., Ltd., "Rhodamin 6G" manufactured by Taga Chemical Industries, Ltd.). In addition, a commercially available xanthene dye can be used as a starting material, and synthesized by referring to Japanese Patent Application Laid-Open No. 2010-32999.

[0279] As other dyes other than the above, an azo dye, a cyanine dye, a triphenylmethane dye, a thiazole dye, a xanthene dye, a phthalocyanine dye, a quinophthalone dye, an anthraquinone dye, a naphthoquinone dye, a quinone imine dye, a methine dye, an azomethine dye, a squarylium dye, an acridine dye, a styryl dye, a coumarin dye, a quinoline dye, and a nitro dye, and the like can be used, respectively using a well-known dye.

[0280] As such a dye, specifically, C.I. Solvent Yellow 4 (hereinafter, the description of C.I. Solvent Yellow is omitted, and only the number is described, and the same applies to the other), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189;

[0281] C.I. Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247;

[0282] C.I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0283] C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0284] C.I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

[0285] C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and C.I. Solvent dyes,

[0286] C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

[0287] C.I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 57, 66, 73, 76, 80, 88, 91, 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, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 418, 422, 426;

[0288] C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0289] C.I. Acid Violet 6B, 7, 15, 16, 17, 19, 21, 23, 24, 25, 34, 38, 49, 72;

[0290] C.I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;

[0291] C.I. 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 the like C.I. Acid Dyes;

[0292] C.I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141;

[0293] C.I. 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;

[0294] C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0295] C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0296] C.I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;

[0297] C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and C.I. Direct dyes;

[0298] C.I. Disperse Yellow 51, 54, 76;

[0299] C.I. Disperse Violet 26, 27;

[0300] C.I. Disperse Blue 1, 14, 56, 60 and C.I. Disperse dyes,

[0301] C.I. 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;

[0302] C.I. Basic Violet 2;

[0303] C.I. Basic Red 9;

[0304] C.I. Basic Green 1; and C.I. Basic Dyes,

[0305] C.I. Reactive Yellow 2, 76, 116;

[0306] C.I. Reactive Orange 16;

[0307] C.I. Reactive Red 36; and C.I. Reactive Dyes,

[0308] C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0309] C.I. Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 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;

[0310] C.I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0311] C.I. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;

[0312] C.I. Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84;

[0313] C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and C.I. Mordant Dyes,

[0314] C.I. Vat Green 1 and C.I. Vat Dyes and the like.

[0315] These dyes can use one dye or a plurality of dyes for each color, or can combine dyes of each color.

[0316] As pigments, for example, pigments classified as pigments (published by The Society of Dyers and Colourists) can be exemplified by the following pigments.

[0317] Green pigments: C.I. Pigment Green 7, 36, 58, etc.

[0318] Yellow pigments: C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, etc.

[0319] Orange pigments: C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.

[0320] Red pigments: C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, etc.

[0321] Blue pigments: C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60, etc.

[0322] Violet pigments: C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38, etc.

[0323] These pigments can use one pigment or a plurality of pigments for each color, or can combine pigments of each color.

[0324] Among them, yellow pigments and / or blue pigments are preferred, and preferably at least one selected from the group consisting of C.I. Pigment Yellow 150, C.I. Pigment Yellow 185, C.I. Pigment Blue 15:3, C.I. Pigment Blue 15:4, and C.I. Pigment Blue 15:6. Note that, from the viewpoint of further improving the stability before and after post-baking, the colored resin composition of the present application preferably does not contain pigments other than the compound represented by formula (I), or when containing pigments other than the compound represented by formula (I), the pigments contain blue pigments (particularly at least one selected from the group consisting of C.I. Pigment Blue 15:3, C.I. Pigment Blue 15:4, and C.I. Pigment Blue 15:6).

[0325] The pigment can be subjected to rosin treatment, surface treatment using a pigment derivative into which an acidic group or a basic group is introduced, graft treatment of the surface of the pigment with a high molecular compound or the like, microparticulation treatment based on a sulfuric acid microparticulation method or the like, cleaning treatment based on an organic solvent, water or the like for removing impurities, removal treatment based on an ion exchange method or the like of ionic impurities, and the like as needed. The particle diameter of the pigment is preferably substantially uniform. The pigment is subjected to dispersion treatment by containing a pigment dispersant, and can be made into a pigment dispersion liquid in a state of being uniformly dispersed in a pigment dispersant solution. The pigment can be subjected to dispersion treatment alone or in a mixture of a plurality of kinds.

[0326] As the pigment dispersant, a surfactant or the like can be cited, and can be any one of a cationic type, an anionic type, a nonionic type and an amphoteric type. Specifically, a polyester type, a polyamine type and an acrylic type surfactant or the like can be cited. These pigment dispersants can be used alone or in combination of two or more. As the pigment dispersant, when represented by a trade name, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by ZENECA (UK) Ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark), BYK (registered trademark) (manufactured by BYK-Chemie), and the like can be cited.

[0327] When the pigment dispersant is used, the amount of use thereof is preferably 10 parts by mass to 200 parts by mass, more preferably 15 parts by mass to 180 parts by mass, and further preferably 20 parts by mass to 160 parts by mass, with respect to 100 parts by mass of the pigment. When the amount of use of the pigment dispersant is in the above range, there is a tendency that a more uniform dispersion state of the pigment dispersion liquid is obtained when two or more kinds of pigments are used.

[0328] When the colorant (A) contains the colorant (A2), the content rate of the colorant (A2) is preferably 1 to 80% by mass, more preferably 1 to 70% by mass, and further preferably 1 to 60% by mass, in the total amount of the colorant (A). In addition, the content rate of the colorant (A2) can be 5% by mass or more, can be 10% by mass or more, or can be 20% by mass or more, in the total amount of the colorant (A). In addition, the content rate of the colorant (A2) can be 40% by mass or less, can be 20% by mass or less, or can be 10% by mass or less, in the total amount of the colorant (A).

[0329] The content of the colorant (A) in the colored resin composition is preferably 0.5 to 80% by mass, more preferably 1 to 70% by mass, further preferably 2 to 55% by mass, and particularly preferably 8 to 50% by mass, relative to the total amount of solid components. When the content of the colorant (A) is within the above range, the desired spectral properties and color density are more easily obtained.

[0330] <Resin (B)>

[0331] The resin (B) is not particularly limited and is preferably an alkali-soluble resin. As the resin (B), the following resins [K1] to [K6] and the like can be given.

[0332] Resin [K1]: a copolymer of at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from an unsaturated carboxylic acid and an unsaturated carboxylic anhydride and a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenic unsaturated bond;

[0333] Resin [K2]: a copolymer of (a) and (b) and a monomer (c) (wherein (c) is different from (a) and (b)) copolymerizable with (a) (hereinafter sometimes referred to as "(c)");

[0334] Resin [K3]: a copolymer of (a) and (c);

[0335] Resin [K4]: a resin obtained by reacting (b) with a copolymer of (a) and (c);

[0336] Resin [K5]: a resin obtained by reacting (a) with a copolymer of (b) and (c);

[0337] Resin [K6]: a resin obtained by reacting (a) with a copolymer of (b) and (c) and further reacting with a polycarboxylic acid and / or a carboxylic anhydride.

[0338] As (a), specifically, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid, and the like can be given.

[0339] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, 1,4-cyclohexene dicarboxylic acid, and the like can be given.

[0340] Bicyclic unsaturated compounds containing a carboxyl group such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, and the like;

[0341] Unsaturated dicarboxylic anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, and the like;

[0342] Unsaturated mono[(meth)acryloyloxyalkyl] esters of a polybasic carboxylic acid of two or more, such as succinic acid mono[2-(meth)acryloyloxyethyl] ester, phthalic acid mono[2-(meth)acryloyloxyethyl] ester, and the like.

[0343] Unsaturated acrylate esters and the like containing a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl)acrylic acid and the like.

[0344] Among them, from the viewpoint of copolymerizability and the solubility of the resulting resin in an aqueous alkali solution, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred.

[0345] (b) is a polymerizable compound having, for example, a cyclic ether structure (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) having 2 to 4 carbon atoms and an ethylenic unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0346] Note that, in the present specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The same applies to "(meth)acryloyl group" and "(meth)acrylate ester" and the like.

[0347] As (b), for example, monomer (b1) having an oxirane group and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b1)"), monomer (b2) having an oxetane group and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b2)"), monomer (b3) having a tetrahydrofuran group and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b3)"), and the like can be given.

[0348] As (b1), for example, monomers (b1-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)") and monomers (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)") can be given.

[0349] As (b1-1), 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(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, and the like can be given.

[0350] As (b1-2), vinyl cyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000; manufactured by Daicel Corp.), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer A400; manufactured by Daicel Corp.), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer M100; manufactured by Daicel Corp.), 3,4-epoxytricyclo[5.2.1.02'6]decyl (meth)acrylate, a compound represented by formula (R1), a compound represented by formula (R2), and the like can be given. 2,6

[0351]

[0352] [In formula (R1) and formula (R2), R ra and R rb represent a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group can be substituted with a hydroxyl group.

[0353] X ra and X rb represent a single bond, *-R rc -, *-R rc -O-, *-R rc -S-, or *-R​rc -NH-.

[0354] R rc It represents alkyl diols with 1 to 6 carbon atoms.

[0355] * indicates a bonding site with O.

[0356] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.

[0357] Examples of alkyl groups in which hydrogen atoms are replaced by hydroxyl groups include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, and 4-hydroxybutyl.

[0358] As R ra and R rb 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.

[0359] Examples of alkyl 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.

[0360] As X ra and X rb Examples of preferred components include single bonds, methylene, ethylene, *-CH2-O- and *-CH2CH2-O-, and examples of more preferred components include single bonds and *-CH2CH2-O- (* indicates the bonding site with O).

[0361] Examples of compounds represented by formula (R1) include compounds represented by any of formulas (R1-1) to (R1-15). Among these, compounds represented by formulas (R1-1), (R1-3), (R1-5), (R1-7), (R1-9), or (R1-11) to (R1-15) are preferred, and compounds represented by formulas (R1-1), (R1-7), (R1-9), or (R1-15) are more preferred.

[0362]

[0363]

[0364] As the compound represented by formula (R2), mention can be made of a compound represented by any one of formulae (R2-1) to (R2-15), and the like. Among them, a compound represented by formula (R2-1), formula (R2-3), formula (R2-5), formula (R2-7), formula (R2-9), or formula (R2-11) to (R2-15) is preferred, and a compound represented by formula (R2-1), formula (R2-7), formula (R2-9), or formula (R2-15) is more preferred.

[0365]

[0366]

[0367] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. As (b2), mention can be made of 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like.

[0368] As (b3), a monomer having a tetrahydrofurfuryl group and a (meth)acryloyloxy group is more preferred. As (b3), specifically, mention can be made of tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Ltd.), tetrahydrofurfuryl methacrylate, and the like.

[0369] As (b), from the viewpoint of being able to make the reliability of the obtained color filter, such as heat resistance, reagent resistance, and the like, higher, (b1) is preferred. Further, from the viewpoint of the storage stability of the colored curable composition being more excellent, (b1-2) is more preferred.

[0370] As (c), for example, mention can be made of methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-8-yl (meth)acrylate (in this technical field, it is called as "(meth)acrylic acid dicyclopentyl ester" as a common name. In addition, sometimes it is called as "(meth)acrylic acid tricyclodecyl ester"), tricyclo[5.2.1.0 2,6Decen-8-yl ester (which is called "(dicyclopentenyl) (meth) acrylate" as a conventional name in this technical field), dicyclopentyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl (meth) acrylate, and the like (meth) acrylate esters;

[0371] 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and the like (meth) acrylate esters containing a hydroxyl group;

[0372] diethyl maleate, diethyl fumarate, diethyl itaconate, and the like diesters of dicarboxylic acids;

[0373] bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-t-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxy-carbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(t-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene, and the like bicyclic unsaturated compounds;

[0374] N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate, N-(9-acridinyl)maleimide, and the like dicarbonylimide derivatives;

[0375] styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like.

[0376] As (c), 2-ethylhexyl (meth)acrylate, dicyclopentyl (meth)acrylate, benzyl (meth)acrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and the like are preferred, and from the viewpoints of copolymerizability and heat resistance, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and the like are more preferred.

[0377] In the resin [Kl], the ratio of the structural units from each unit is preferably 2 to 60 mol% of the structural unit from (a) and 40 to 98 mol% of the structural unit from (b) in all the structural units constituting the resin [Kl], and more preferably 10 to 50 mol% of the structural unit from (a) and 50 to 90 mol% of the structural unit from (b).

[0378] When the ratio of the structural units of the resin [Kl] is in the above range, there is a tendency that the storage stability of the colored resin composition, the developability at the time of forming a colored pattern, and the solvent resistance of the obtained color filter are excellent.

[0379] The resin [Kl] can be produced, for example, by using the method described in the literature "Experimental Methods of Polymer Synthesis" (Nobuo Oki, issued by Shokabo Publishing Co., Inc., 1st edition, 1st printing, March 1, 1972) and the references described in the literature as a reference.

[0380] Specifically, a method in which a prescribed amount of (a) and (b), a polymerization initiator, a solvent, and the like are charged into a reaction vessel, a deoxidized atmosphere is prepared, for example, by replacing oxygen with nitrogen, and heating and keeping warm are performed while stirring can be mentioned. Note that the polymerization initiator and the solvent and the like used here are not particularly limited, and a polymerization initiator and a solvent generally used in the field can be used. For example, as the polymerization initiator, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), and the like), organic peroxides (benzoyl peroxide, and the like) can be mentioned, and as the solvent, a solvent that dissolves each monomer, such as the solvent (E) described later, can be mentioned.

[0381] Note that the obtained copolymer can be used as it is after the reaction, can be used after being concentrated or diluted, or can be used as a substance taken out in a solid (powder) form by reprecipitation or the like. In particular, by using the solvent contained in the colored resin composition as the solvent at the time of the polymerization, the solution after the reaction can be directly used for the production of the colored resin composition, and thus the manufacturing process of the colored resin composition can be simplified.

[0382] In the resin [K2], the ratio of the structural units from each unit is preferably 2 to 45 mol% of the structural unit from (a), 2 to 95 mol% of the structural unit from (b), and 1 to 65 mol% of the structural unit from (c), among all the structural units constituting the resin [K2], and more preferably 5 to 40 mol% of the structural unit from (a), 5 to 80 mol% of the structural unit from (b), and 5 to 60 mol% of the structural unit from (c).

[0383] When the ratio of the structural units of the resin [K2] is within the above range, there is a tendency that the storage stability of the colored resin composition, the developability at the time of forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained color filter are excellent.

[0384] The resin [K2] can be produced, for example, in the same manner as the method described as the production method of the resin [K1].

[0385] In the resin [K3], the ratio of the structural units from each unit is preferably 2 to 60 mol% of the structural unit from (a) and 40 to 98 mol% of the structural unit from (c), among all the structural units constituting the resin [K3], and more preferably 10 to 50 mol% of the structural unit from (a) and 50 to 90 mol% of the structural unit from (c).

[0386] The resin [K3] can be produced, for example, in the same manner as the method described as the production method of the resin [K1].

[0387] The resin [K4] can be produced by obtaining a copolymer of (a) and (c) and adding a cyclic ether having 2 to 4 carbon atoms possessed by (b) to a carboxylic acid and / or a carboxylic anhydride possessed by (a).

[0388] First, a copolymer of (a) and (c) is produced in the same manner as the method described as the production method of the resin [K1]. In this case, the ratio of the structural units from each unit is preferably the same as the ratio described in the resin [K3].

[0389] Next, a cyclic ether having 2 to 4 carbon atoms possessed by (b) is reacted with a part of the carboxylic acid and / or the carboxylic anhydride from (a) in the above copolymer.

[0390] After the copolymer of (a) and (c) is produced, the atmosphere in the flask is then replaced from nitrogen to air, and a reaction catalyst (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone or the like) or the like of (b), a carboxylic acid or a carboxylic anhydride, and a cyclic ether are put into the flask, for example, and reacted at 60 to 130°C for 1 to 10 hours, whereby the resin [K4] can be produced.

[0391] The amount of use of (b) is preferably 5 to 80 moles, more preferably 10 to 75 moles, relative to 100 moles of (a). By being in this range, there is a tendency for the balance of storage stability of the colored resin composition, developability at the time of pattern formation, and solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern to become good. The reactivity of the cyclic ether is high, and from the viewpoint of not easily remaining unreacted (b), (bl), further (bl-1) is preferable as (b) used in the resin [K4].

[0392] The amount of use of the above-mentioned reaction catalyst is preferably 0.001 to 5 parts by mass, relative to 100 parts by mass of the total amount of (a), (b), and (c). The amount of use of the above-mentioned polymerization inhibitor is preferably 0.001 to 5 parts by mass, relative to 100 parts by mass of the total amount of (a), (b), and (c).

[0393] The feeding method, reaction temperature, and time, and the like reaction conditions can be appropriately adjusted in consideration of the manufacturing equipment, the amount of heat generation based on polymerization, and the like. Note that the feeding method, reaction temperature, and the like can be appropriately adjusted in consideration of the manufacturing equipment, the amount of heat generation based on polymerization, and the like, similarly to the polymerization conditions.

[0394] For the resin [K5], as the first stage, a copolymer of (b) and (c) is obtained similarly to the production method of the above-mentioned resin [Kl]. Similarly to the above, for the obtained copolymer, the solution after the reaction can be used as it is, a solution after concentration or dilution can be used, or a substance taken out in a solid (powder) form by a method such as reprecipitation can be used.

[0395] The ratio of the structural units from (b) and (c) relative to the total number of moles of all the structural units constituting the above-mentioned copolymer is preferably 5 to 95 mole% of the structural units from (b) and 5 to 95 mole% of the structural units from (c), more preferably 10 to 90 mole% of the structural units from (b) and 10 to 90 mole% of the structural units from (c), respectively.

[0396] Further, the carboxylic acid or carboxylic anhydride possessed by (a) is reacted with the cyclic ether from (b) possessed by the copolymer of (b) and (c) under the same conditions as the production method of the resin [K4], whereby the resin [K5] can be obtained.

[0397] The amount of use of (a) in the reaction with the above copolymer is preferably 5 to 100 moles relative to 100 moles of (b). The reactivity of the cyclic ether is high, and from the viewpoint of ease of non-remained (b), (bl) is preferable, and (bl-1) is further preferable as (b) used in the resin [K5].

[0398] The resin [K6] is a resin obtained by further reacting the resin [K5] with a carboxylic anhydride. The carboxylic anhydride is reacted with the hydroxyl group generated by the reaction of the cyclic ether and the carboxylic acid or the carboxylic anhydride.

[0399] As the carboxylic anhydride, succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxy-bicyclo[2.2.1]hept-2-ene anhydride, and the like can be given. The amount of use of the carboxylic anhydride is preferably 0.1 to 1 mole relative to 1 mole of the amount of use of (a).

[0400] As the specific resin (B), the resin [K1] such as a 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid copolymer; a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, a glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, a glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6glycidyl (meth)acrylate and a copolymer of (meth)acrylic acid, tricyclodecane (meth)acrylate, and styrene, a resin obtained by reacting a copolymer of (meth)acrylic acid, tricyclodecane (meth)acrylate, and glycidyl (meth)acrylate with tetrahydrophthalic anhydride, a resin obtained by reacting a copolymer of (meth)acrylic acid, 2-ethylhexyl (meth)acrylate, glycidyl (meth)acrylate, and dicyclopentyl (meth)acrylate with succinic anhydride, and the like [K6], and the like.

[0401] Among them, as the resin (B), a copolymer (resin [Kl] or resin [K2]) derived from structural units selected from at least one of an unsaturated carboxylic acid and an unsaturated carboxylic anhydride and structural units having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenic unsaturated bond, or the resin [K6], more preferably the resin [Kl] or the resin [K2], is preferable.

[0402] The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 500 to 100,000, more preferably 600 to 50,000, and further preferably 700 to 30,000. When the molecular weight is within the above range, there is a tendency that the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developing solution is good, and the resolution of the colored pattern is improved.

[0403] The dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.

[0404] The acid value of the resin (B) is preferably 10 to 170 mg-KOH / g, more preferably 20 to 150 mg-KOH / g, and further preferably 30 to 135 mg-KOH / g, in terms of the solid content. Here, the acid value is a value determined as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained, for example, by titration using an aqueous potassium hydroxide solution.

[0405] The content ratio of the resin (B) is preferably 7 to 80% by mass, more preferably 13 to 75% by mass, further preferably 17 to 70% by mass, and more further preferably 17 to 55% by mass, with respect to the total amount of the solid content. When the content ratio of the resin (B) is within the above range, there is a tendency that a colored pattern can be formed, and the resolution and the residual film rate of the colored pattern are improved.

[0406] < POLYMERIZABLE COMPOUND (C) >

[0407] The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenic unsaturated bond, and the like, and is preferably a (meth)acrylate compound.

[0408] The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds. As such a polymerizable compound, for example, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, and the like can be given.

[0409] Preferably, at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate is contained, and more preferably, at least one selected from the group consisting of trimethylolpropane triacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate is contained.

[0410] The weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2900, and more preferably 250 to 1500.

[0411] When the colored resin composition of the present application contains the polymerizable compound (C), the content of the polymerizable compound (C) is preferably 7 to 65 mass%, more preferably 13 to 60 mass%, and further preferably 17 to 55 mass%, relative to the total amount of the solid components. When the content of the polymerizable compound (C) is within the above range, there is a tendency that the residual film rate at the time of forming a colored pattern and the reagent resistance of the color filter are improved.

[0412] <Polymerization initiator (D)>

[0413] The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating active radicals, acids, or the like and initiating polymerization under the action of light or heat, and a publicly known polymerization initiator can be used.

[0414] As the polymerization initiator generating active radicals, for example, an alkylphenone compound, a triazine compound, an acyloxyphosphine compound, an O-acyl oxime compound, and a bisimidazole compound can be given.

[0415] The above O-acyl oxime compound is a compound having a partial structure represented by formula (d1). Hereinafter, * indicates a bonding site.

[0416]

[0417] As the above O-acyl oxime compound, for example, N-benzoyloxy-l-(4-phenylsulfanylphenyl)butane-l- ketone-2-imine, N-benzoyloxy-l-(4-phenylsulfanylphenyl)octane-l-ketone-2-imine, N-benzoyloxy-l-(4- phenylsulfanylphenyl)-3-cyclopentylpropane-l-ketone-2-imine, N-acetyloxy-l-[9-ethyl-6-(2-methylbenzoyl)- 9H-carbazol-3-yl]ethane-l-imine, N-acetyloxy-l-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4- dioxocyclopentylmethoxy)benzoyl}-9H-carbazol-3-yl]ethane-l-imine, N-acetyloxy-l-[9-ethyl-6-(2- methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-l-imine, N-benzoyloxy-l-[9-ethyl-6-(2- methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-l-ketone-2-imine, N-acetyloxy-l-(4- phenylsulfanylphenyl)-3-cyclohexylpropane-l-ketone-2-imine, and the like can be given. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (all of which are manufactured by BASF), N-1919 (manufactured by ADEKA), TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Material Co., Ltd.), and the like can also be used. Among these, the O-acyl oxime compound is preferably at least one selected from the group consisting of N-acetyloxy-l-(4-phenylsulfanylphenyl)-3- cyclohexylpropane-l-ketone-2-imine, N-benzoyloxy-l-(4-phenylsulfanylphenyl)butane-l-ketone-2-imine, N-benzoyloxy-l-(4-phenylsulfanylphenyl)octane-l-ketone-2-imine, and N-benzoyloxy-l-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-l-ketone-2-imine, and more preferably N-acetyloxy-l-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-l-ketone-2-imine and N-benzoyloxy-l-(4-phenylsulfanylphenyl)octane-l-ketone-2-imine. With these O-acyl oxime compounds, there is a tendency to obtain a high-brightness color filter.

[0418] The above alkyl phenone compound is preferably a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring can have a substituent.

[0419]

[0420] As the compound having a partial structure represented by formula (d2), for example, 2-methyl-2-morpholino-l-(4-methylthiophenyl)propan-l-one, 2-dimethylamino-l-(4-morpholinophenyl)-2-benzylbutan-l-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-l-[4-(4-morpholinyl)phenyl]butan-l-one, and the like can be given. Commercially available products such as Irgacure (registered trademark) 369, 907, 379 (all of which are manufactured by BASF Corporation), and the like can also be used.

[0421] As the compound having a partial structure represented by formula (d3), for example, 2-hydroxy-2-methyl-l-phenylpropan-l-one, 2-hydroxy-2-methyl-l-[4-(2-hydroxyethoxy)phenyl]propan-l-one, l-hydroxycyclohexyl phenyl ketone, an oligomer of 2-hydroxy-2-methyl-l-(4-isopropenylphenyl)propan-l-one, α,α-diethoxyacetophenone, benzil dimethyl ketal, and the like can be given.

[0422] In terms of sensitivity, as the alkylphenone compound, a compound having a partial structure represented by formula (d2) is preferred.

[0423] As the above-mentioned triazine compound, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-l,3,5-triazine, and the like can be given.

[0424] As the above-mentioned acylphosphine oxide compound, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, and the like can be given. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF), and the like can also be used.

[0425] As the above-mentioned bisimidazole compounds, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbisimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbisimidazole (for example, refer to Japanese Patent Application Publication No. 6-75372, Japanese Patent Application Publication No. 6-75373, and the like), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxylphenyl)bisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxylphenyl)bisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxylphenyl)bisimidazole (for example, refer to Japanese Patent Application Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, and the like), a bisimidazole compound in which the phenyl group at the 4,4',5,5'-positions is substituted with a carbalkoxy group (for example, refer to Japanese Patent Application Publication No. 7-10913, and the like), and the like can be given.

[0426] Further, as the polymerization initiator (D), benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and the like benzoin compounds; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyl diphenyl sulfide, 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, and the like benzophenone compounds; 9,10-phenanthrenequinone, 2-ethylanthraquinone, camphorquinone, and the like quinone compounds; 10-butyl-2-chloroacridone, benzil, methyl benzoylformate, a titanocene compound, and the like can be given. These are preferably used in combination with the polymerization initiation aid (D1) (particularly, an amine compound) described later.

[0427] As the acid-generating polymerization initiator, for example, 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetyloxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetyloxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, and the like can be given. salts, nitrobenzyltoluenesulfonate, benzoin toluenesulfonate, and the like.

[0428] As the polymerization initiator (D), a polymerization initiator containing at least one selected from the group consisting of an alkylbenzophenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyl oxime compound, and a bisimidazole compound is preferred, and a polymerization initiator containing an O-acyl oxime compound is more preferred.

[0429] When the colored resin composition of the present application contains the polymerization initiator (D), the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, there is a tendency that the sensitivity is increased and the exposure time is shortened, and thus the productivity of the color filter is improved.

[0430] < Polymerization initiation aid (D1 ) >

[0431] The polymerization initiation aid (D1) is a compound or a sensitizer for promoting the polymerization of the polymerizable compound initiated by the polymerization initiator. When the polymerization initiation aid (D1) is contained, it is generally used in combination with the polymerization initiator (D).

[0432] As the polymerization initiation aid (D1), amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds, etc. can be given.

[0433] As the above-mentioned amine compounds, 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 (known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc. can be given, of which 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Kodak) can also be used.

[0434] As the above-mentioned alkoxyanthracene compounds, 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, etc. can be given.

[0435] As the above-mentioned thioxanthone compounds, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, etc. can be given.

[0436] As the above-mentioned carboxylic acid compounds, phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc. can be given.

[0437] When these polymerization initiator aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiator aid (D1) is within this range, it is possible to further form a colored pattern with high sensitivity, and there is a tendency for the productivity of the color filter to improve.

[0438] <Solvent (E)>

[0439] The solvent (E) is not particularly limited, and a solvent generally used in the field can be used. For example, ester solvents (solvents containing -COO- within the molecule and not containing -O-), ether solvents (solvents containing -O- within the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- within the molecule), ketone solvents (solvents containing -CO- within the molecule and not containing -COO-), alcohol solvents (solvents containing OH within the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like can be given.

[0440] As the ester solvent, methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexyl acetate, and γ-butyrolactone, and the like can be given.

[0441] As the ether solvent, 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-l-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, and methyl anisole, and the like can be given.

[0442] ​As the ether ester solvents, there are mentioned 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, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and the like.

[0443] As the ketone solvents, there are mentioned 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, isophorone and the like.

[0444] As the alcohol solvents, there are mentioned methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerol and the like.

[0445] As the aromatic hydrocarbon solvents, there are mentioned benzene, toluene, xylene and mesitylene and the like.

[0446] As the amide solvents, there are mentioned N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and the like.

[0447] The solvent (E) is preferably one or more selected from the group consisting of ether solvents, ether ester solvents, ketone solvents and amide solvents, and further preferably contains one or more selected from the group consisting of diethylene glycol methyl ethyl ether, propylene glycol monomethyl ether acetate, diacetone alcohol and N-methylpyrrolidone.

[0448] The content ratio of the solvent (E) is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, relative to the total amount of the colored resin composition. In other words, the solid content of the colored resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. When the content ratio of the solvent (E) is within the above range, the planarity at the time of coating becomes good, and further the color density does not become insufficient at the time of forming a color filter, and thus there is a tendency that the display characteristics become good.

[0449] <Leveling agent (F)>

[0450] As the leveling agent (F), there are mentioned silicone-based surfactants, fluorine-based surfactants, silicone-based surfactants having a fluorine atom and the like. They can have a polymerizable group in the side chain.

[0451] As the organic silicone-based surfactant, a surfactant having a siloxane bond in the molecule, etc. can be given. Specifically, 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: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by MOMENTIVE PERFORMANCE MATERIALS JAPAN KK), etc. can be given.

[0452] As the above-mentioned fluorine-based surfactant, a surfactant having a fluorocarbon chain in the molecule, etc. can be given. Specifically, FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Corp.), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi Materials Electronic Materials Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by AGC Inc. (former Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemicals Ltd.), etc. can be given.

[0453] As the above-mentioned organic silicone-based surfactant having a fluorine atom, a surfactant having a siloxane bond and a fluorocarbon chain in the molecule, etc. can be given. Specifically, MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corp.), etc. can be given.

[0454] When the colored resin composition of the present application contains the leveling agent (F), the content of the leveling agent (F) is preferably 0.001 to 0.2 mass%, more preferably 0.002 to 0.1 mass%, and further preferably 0.005 to 0.05 mass% with respect to the total amount of the colored resin composition. Note that the content does not include the content of the above-mentioned pigment dispersant. When the content of the leveling agent (F) is within the above-mentioned range, the flatness of the color filter becomes good.

[0455] <Other components>

[0456] The colored resin composition can contain, as necessary, fillers, other high molecular compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and the like, which are known in the art.

[0457] <Manufacturing method of colored resin composition>

[0458] The colored resin composition can be manufactured, for example, by mixing the colorant (A) containing the compound (I), the resin (B), and, as necessary, the polymerizable compound (C), the polymerization initiator (D), the solvent (E), the leveling agent (F), the polymerization initiator aid (D1), and other components.

[0459] The compound (I) and, as necessary, other pigments can be previously contained in a pigment dispersion liquid. The remaining components are mixed in the pigment dispersion liquid in such a manner as to achieve a prescribed concentration, whereby the target colored resin composition can be manufactured.

[0460] When a dye is contained, the dye can be previously dissolved in a part or all of the solvent (E) to prepare a solution. The solution is preferably filtered with a filter having a pore size of about 0.01 to 1 μm.

[0461] The mixed colored resin composition is preferably filtered with a filter having a pore size of about 0.01 to 10 μm.

[0462] [Color filter]

[0463] As a method of manufacturing a colored pattern of a color filter from the colored resin composition of the present application, photolithography, inkjet method, printing method, and the like can be given. Among them, photolithography is preferred. The photolithography is a method of forming a composition layer by applying the above-mentioned colored resin composition to a substrate and drying it, and exposing the composition layer through a photomask and developing it. In the photolithography, by not using a photomask and / or not developing at the time of exposure, a colored coating film that is a cured product of the above-mentioned composition layer can be formed.

[0464] The film thickness of the color filter (cured film) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, further preferably 3 μm or less, still further preferably 1.5 μm or less, particularly preferably 0.5 μm or less, preferably 0.1 μm or more, more preferably 0.2 μm or more, further preferably 0.3 μm or more.

[0465] As the substrate, a glass plate such as quartz glass, borosilicate glass, aluminosilicate glass, soda-lime glass coated with silicon dioxide, a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, a substrate on which an aluminum, silver, silver / copper / palladium alloy thin film or the like is formed on the above substrate can be used. Other color filter layers, resin layers, transistors, circuits or the like can be formed on these substrates. A substrate subjected to HMDS treatment on a silicon substrate can also be used.

[0466] The formation of each color pixel based on photolithography can be performed using known or conventional apparatuses and conditions. For example, it can be produced as follows. First, the colored resin composition is applied to a substrate, and heat drying (pre-baking) and / or reduced pressure drying is performed to remove volatile components such as solvents and dry the same to obtain a smooth composition layer. As the application method, spin coating, slit coating, slit and spin coating, and the like can be mentioned. The temperature at the time of heat drying is preferably 30 to 120°C, more preferably 50 to 110°C. In addition, as the heat time, 10 seconds to 60 minutes is preferred, more preferably 30 seconds to 30 minutes. At the time of reduced pressure drying, it is preferred to perform at a temperature in the range of 20 to 25°C under a pressure of 50 to 150 Pa. The film thickness of the composition layer is not particularly limited, and can be appropriately selected depending on the film thickness of the target color filter.

[0467] Next, the composition layer is exposed through a photomask for forming a target colored pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target use is used. As the light source used in the exposure, a light source generating light of a wavelength of 250 to 450 nm is preferred. For example, light of less than 250 nm can be cut off using a filter cutting off the wavelength region, or light around 436 nm, around 408 nm, around 365 nm can be selectively extracted using a band pass filter extracting these wavelength regions. Specifically, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, and the like can be mentioned. In order to be able to uniformly irradiate parallel light to the entire exposure surface, to perform accurate alignment of the photomask and the substrate, a reduction projection exposure apparatus or a proximity exposure apparatus using a mask aligner and a stepper or the like is preferred.

[0468] The exposed composition layer is brought into contact with a developer to perform development, thereby forming a colored pattern on the substrate. By development, the unexposed portion of the composition layer is dissolved in the developer and removed. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is preferred. The concentration in the aqueous solution of these alkaline compounds is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Further, the developer can contain a surfactant. The development method can be any one of a paddle method, an immersion method, a spray method, and the like. Further, the substrate can be inclined at an arbitrary angle at the time of development.

[0469] After development, water washing is preferably performed.

[0470] The obtained colored pattern is preferably further subjected to post-baking. The post-baking temperature is preferably 80 to 250°C, more preferably 100 to 245°C. The post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.

[0471] The colored pattern and the colored coating film thus obtained are useful as a color filter, which is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL display device, and the like), electronic paper, a solid-state imaging element, and the like.

[0472] Examples

[0473] Hereinafter, the present application will be described in more detail by citing examples, and the present application is of course not limited by the following examples. In the examples, unless otherwise specified, "parts" means "parts by mass", and "%" means "mass %".

[0474] The structure of the compound was confirmed by a mass spectrometer (MALDI-TOF MS; JEOL Ltd. JMS-S3000).

[0475] (Synthesis of the colorant)

[0476] [Example 1]

[0477] A solution prepared from 3-butyne-l-ol (Tokyo Chemical Industry Co., Inc.) 2.1 parts and tetrahydrofuran 11 parts was added dropwise to phenylphosphorodichloridate (Tokyo Chemical Industry Co., Inc.) 6.7 parts, tetrahydrofuran (Fuji Photo Film Co., Ltd. and Wako Pure Chemical Industries, Ltd.) 11 parts at 0°C. Subsequently, a solution prepared from triethylamine (Tokyo Chemical Industry Co., Inc.) 7.6 parts and tetrahydrofuran 11 parts was added dropwise at 0°C. After stirring for 3 hours at room temperature, ion-exchanged water 33 parts was added. The resulting solution was partitioned with chloroform (Fuji Photo Film Co., Ltd. and Wako Pure Chemical Industries, Ltd.), and the organic layer was recovered. After drying with sodium sulfate, the solvent was removed using a rotary evaporator. The resulting mixture was purified by a silica gel column to obtain a compound represented by formula (1) 2.8 parts.

[0478]

[0479] To triethylamine (Tokyo Chemical Industry Co., Inc.) 4.3 parts, dimethyl sulfoxide (Tokyo Chemical Industry Co., Inc.) 4.3 parts, a compound represented by formula (1) 0.86 parts, 1,3-diiodobenzene (Tokyo Chemical Industry Co., Inc.) 0.5 parts, dichlorobis(triphenylphosphine)palladium (Tokyo Chemical Industry Co., Inc.) 0.13 parts, and copper iodide (Fuji Photo Film Co., Ltd. and Wako Pure Chemical Industries, Ltd.) 0.18 parts were added, and stirred for 8 hours at room temperature. Then, 1 equivalent of an aqueous sodium hydroxide solution 26 parts was added at room temperature, and after stirring, the precipitated solid was removed using cerite. The resulting aqueous solution was partitioned with ethyl acetate, and the aqueous layer was recovered. To the aqueous layer, concentrated hydrochloric acid was added to make it acidic, and then partitioned with ethyl acetate again, and the organic layer was recovered. After drying the resulting organic layer with sodium sulfate, the solvent was removed using a rotary evaporator to obtain a compound represented by formula (2) 0.76 parts.

[0480]

[0481] A compound represented by formula (3) (Tokyo Chemical Industry Co., Inc.) 1.2 parts, a compound represented by formula (2) 0.76 parts, and dimethyl sulfoxide (Tokyo Chemical Industry Co., Inc.) 5.9 parts were mixed at room temperature, and stirred for 6 hours while being warmed to 80°C. After cooling the reaction solution to room temperature, ion-exchanged water 30 parts was added. The resulting precipitate was obtained as a suction filtration residue, and washed with ethyl acetate (Fuji Photo Film Co., Ltd. and Wako Pure Chemical Industries, Ltd.) 30 parts. Then, it was dried under reduced pressure with heating at 60°C to obtain a compound represented by formula (4) 1.3 parts.

[0482]

[0483] Identification of the compound represented by formula (4)

[0484] (Mass spectrometer) ionization mode = MALDI-TOF - : m / z = 1602.4

[0485] Exact mass: 1602.3

[0486] [Example 2]

[0487] In the reaction for obtaining the compound represented by formula (2) of Example 1, the 1,3-diiodobenzene used is changed to 1,4-diiodobenzene (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain the compound represented by formula (5).

[0488]

[0489] The compound represented by formula (3) (1.5 parts, manufactured by Tokyo Chemical Industry Co., Ltd.), the compound represented by formula (5) (0.96 parts), and dimethyl sulfoxide (5.9 parts, manufactured by Tokyo Chemical Industry Co., Ltd.) are mixed at room temperature, and warmed to 80°C and stirred for 6 hours. After the reaction solution is cooled to room temperature, ion exchange water (75 parts) is added. The obtained precipitate is taken as a residue by suction filtration, and washed with ethyl acetate (75 parts, manufactured by FUJIFILM Wako Pure Chemical Corporation). Then, it is dried under reduced pressure with heating at 60°C to obtain 1.8 parts of the compound represented by formula (6).

[0490]

[0491] Identification of the compound represented by formula (6)

[0492] (Mass spectrometer) ionization mode = MALDI-TOF - : m / z = 1602.5

[0493] Exact mass: 1602.3

[0494] [Example 3]

[0495] In the reaction for obtaining the compound represented by formula (2) of Example 1, the 1,3-diiodobenzene used is changed to 4,4'-diiodobiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain the compound represented by formula (7).

[0496]

[0497] A compound represented by formula (3) (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.0 part, a compound represented by formula (7) 0.52 part, dimethyl sulfoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) 5.0 parts were mixed at room temperature, and stirred at 110°C for 6 hours. After the reaction solution was cooled to room temperature, methanol (manufactured by FUJIFILM and Wako Pure Chemical Industries, Ltd.) 25 parts was added. The obtained precipitate was obtained as a suction filtration residue, and washed with methanol 25 parts. Then, dried under reduced pressure with heating at 60°C to obtain a compound represented by formula (8) 1.2 parts.

[0498]

[0499] Identification of the compound represented by formula (8)

[0500] (Mass spectrometer) Ionization mode = MALDI-TOF + : m / z = [M+Na] + 1701.2

[0501] Exact mass: 1701.4

[0502] [Example 4]

[0503] In the reaction for obtaining a compound represented by formula (2) of Example 1, 1,3-diiodobenzene used was changed to 2,7-diiodo-9,9-dimethylfluorene (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (9).

[0504]

[0505] A compound represented by formula (3) (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.0 part, a compound represented by formula (9) 0.56 part, dimethyl sulfoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) 5.0 parts were mixed at room temperature, and stirred at 110°C for 6 hours. After the reaction solution was cooled to room temperature, methanol (manufactured by FUJIFILM and Wako Pure Chemical Industries, Ltd.) 25 parts was added. The obtained precipitate was obtained as a suction filtration residue, and washed with methanol 25 parts. Then, dried under reduced pressure with heating at 60°C to obtain a compound represented by formula (10) 1.16 parts.

[0506]

[0507] Identification of the compound represented by formula (10)

[0508] (Mass spectrometer) Ionization mode = MALDI-TOF + : m / z = [M+Na] + 1741.2

[0509] Exact mass: 1741.4

[0510] Example 5

[0511] A mixture of 4-nitrophthalonitrile (5.0 parts), ethanol (4.0 parts), potassium carbonate (20 parts), and N,N-dimethylformamide (50 parts) was stirred at room temperature for 20 hours. Then, ion-exchanged water (100 parts) was added. The resulting precipitate was obtained as a suction filtration residue, and washed with ion-exchanged water (50 parts). Then, drying under reduced pressure with heating at 60°C gave a compound represented by formula (11) (4.0 parts).

[0512]

[0513] A mixture of the compound represented by formula (11) (3.5 parts), aluminum chloride (0.9 parts), diazabicycloundecane (3.1 parts), and n-pentanol (18 parts) was stirred under reflux conditions for 30 hours. After the reaction solution was cooled to room temperature, ethyl acetate (36 parts) was added. The resulting precipitate was obtained as a suction filtration residue, and washed with ethyl acetate (18 parts). Ion-exchanged water (36 parts) was added to the resulting residue, and stirred at room temperature for 0.5 hours. The resulting precipitate was obtained as a suction filtration residue, and washed with ion-exchanged water (18 parts). Then, drying under reduced pressure with heating at 60°C gave a compound represented by formula (12) (1.9 parts).

[0514]

[0515] A mixture of the compound represented by formula (12) (1.0 part), the compound represented by formula (7) (0.4 part), and dimethyl sulfoxide (5.0 parts) was stirred at room temperature for 12 hours while being warmed to 110°C. After the reaction solution was cooled to room temperature, methanol (25 parts) was added. The resulting precipitate was obtained as a suction filtration residue, and washed with methanol (25 parts). Then, drying under reduced pressure with heating at 60°C gave a compound represented by formula (13) (1.0 part).

[0516]

[0517] Identification of the compound represented by formula (13)

[0518] (Mass spectrometer) Ionization mode = MALDI-TOF - : m / z = 2031.9

[0519] Exact mass: 2032.0

[0520] Example 6

[0521] According to the experimental item of page 651 of Tamara V. Basova et al "Molecular organization in the thin films of chloroaluminium hexadecafluorophthalocyanine revealed by polarized Raman spectroscopy" (Thin Solid Films, 2013, Volume 548, 650-656), the phthalonitrile derivative to be used was changed to 4-bromophthalonitrile to obtain a compound represented by formula (14).

[0522]

[0523] A mixture of 1.0 part of the compound represented by formula (14), 0.36 part of the compound represented by formula (2), and 5.0 parts of dimethyl sulfoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) was stirred at room temperature for 12 hours while being warmed to 110°C. After the reaction solution was cooled to room temperature, 25 parts of methanol was added. The obtained precipitate was obtained as a residue of suction filtration, and washed with 25 parts of methanol. Then, drying under reduced pressure with heating at 60°C was performed to obtain 1.2 parts of a compound represented by formula (15).

[0524]

[0525] Identification of the compound represented by formula (15)

[0526] (Mass spectrometer) Ionization mode = MALDI-TOF - : m / z = [M+Na] + 2248.3

[0527] Exact mass: 2248.6

[0528] Example 7

[0529] A mixture of 1.0 part of the compound represented by formula (3) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.21 part of 1,4-benzene diphosphonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 5.0 parts of dimethyl sulfoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) was stirred at room temperature for 6 hours while being warmed to 110°C. After the reaction solution was cooled to room temperature, 25 parts of methanol (manufactured by FUJIFILM and Otsuka Pharmaceutical Co., Ltd.) was added. The obtained precipitate was obtained as a residue of suction filtration, and washed with 25 parts of methanol. Then, drying under reduced pressure with heating at 60°C was performed to obtain 1.07 parts of a mixture of the compounds represented by formula (16), formula (17), and formula (18) (hereinafter, referred to as mixture (1)).

[0530]

[0531] Identification of compound represented by formula (16) (mass spectrometer) Ionization mode = MALDI-TOF + : m / z = [M+Na] + 1337.0

[0532] Exact mass: 1337.2

[0533]

[0534] Identification of compound represented by formula (17) (mass spectrometer) Ionization mode = MALDI-TOF + : m / z = [M+Na] + 1875.1

[0535] Exact mass: 1875.3

[0536]

[0537] Identification of compound represented by formula (18)

[0538] (mass spectrometer) Ionization mode = MALDI-TOF + : m / z = [M+Na] + 2413.1

[0539] Exact mass: 2413.5

[0540] [Comparative Example 1]

[0541] The compound represented by formula (x1) was obtained according to the synthesis method described in Japanese Patent Application Publication No. 2016-75837.

[0542]

[0543] [Measurement of molar absorption coefficient]

[0544] Each of the compounds obtained in Examples 1 to 4, Examples 6 to 7, and Comparative Example 1 was diluted to 0.0280 g / L with N,N-dimethylformamide in a volumetric flask. Then, UV-Vis measurement was performed using a UV-Vis spectrometer (Shimadzu Corporation; V-650), and the molar absorption coefficient at the maximum absorption wavelength (λmax) in the range of 600 to 750 nm was calculated. The results are shown in Table 6.

[0545] [Table 6]

[0546]

[0547] (Resin Synthesis Example 1)

[0548] Into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, an appropriate amount of nitrogen was introduced and replaced with a nitrogen atmosphere, and propylene glycol monomethyl ether acetate 340 parts was charged. While stirring, the mixture was heated to 80°C. Subsequently, a mixture of acrylic acid 57 parts, acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl ester and acrylic acid 3,4-epoxytricyclo[5.2.1.0 2 ,6 ]decane-9-yl ester (containing 1:1 by mole ratio) 54 parts, benzyl methacrylate 239 parts, and propylene glycol monomethyl ether acetate 73 parts was added dropwise over 5 hours. On the other hand, a solution of polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) 40 parts dissolved in propylene glycol monomethyl ether acetate 197 parts was added dropwise over 6 hours. After the completion of the dropwise addition of the solution of the polymerization initiator, the mixture was maintained at 80°C for 3 hours, and then cooled to room temperature to obtain a copolymer (resin (B-1)) solution having a viscosity of 137 mPa-s as measured with a B-type viscometer (23°C) and a solid content of 36.8% by weight. The copolymer thus produced had a weight average molecular weight of 1.0 x 10 3 in terms of polystyrene, a dispersity of 1.97, and an acid value of 111 mg-KOH / g in terms of solid content. The resin (B-1) had the following structural units.

[0549]

[0550] (Preparation of dispersion 1)

[0551] A compound represented by formula (4) 5.0 parts, a dispersant (BYK LPN-6919 manufactured by BYK) 3.0 parts, resin (B-1) (solid content conversion) 3.0 parts, and propylene glycol monomethyl ether acetate 89 parts were mixed, and 300 parts of zirconium oxide beads of 0.4 mm were added. The mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). Then, the zirconium oxide beads were removed by filtration to obtain dispersion 1.

[0552] (Preparation of dispersion 2)

[0553] A compound represented by formula (6) 5.0 parts, a dispersant (BYK LPN-6919 manufactured by BYK) 3.0 parts, resin (B-1) (solid content conversion) 3.0 parts, and propylene glycol monomethyl ether acetate 89 parts were mixed, and 300 parts of zirconium oxide beads of 0.4 mm were added. The mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). Then, the zirconium oxide beads were removed by filtration to obtain dispersion 2.

[0554] (Preparation of dispersion 3)

[0555] A compound represented by formula (x1) 5.0 parts, a dispersing agent (BYK LPN-6919 manufactured by BYK Co.) 8.0 parts, a resin (B-1) (solid content conversion) 8.0 parts, and propylene glycol monomethyl ether acetate 79 parts were mixed, 300 parts of zirconium oxide beads of 0.4 mm were added, and oscillation was performed using a paint conditioner (manufactured by LAU Co.) for 1 hour. Then, the zirconium oxide beads were removed by filtration to obtain dispersion liquid 3.

[0556] (Preparation of dispersion liquid 4)

[0557] A compound represented by formula (4) 5.00 parts, a dispersing agent (BYK LPN-6919 manufactured by BYK Co.) 2.86 parts, a resin (B-1) (solid content conversion) 2.38 parts, and propylene glycol monomethyl ether acetate 89.76 parts were mixed, 300 parts of zirconium oxide beads of 0.4 mm were added, and oscillation was performed using a paint conditioner (manufactured by LAU Co.) for 1 hour. Then, the zirconium oxide beads were removed by filtration to obtain dispersion liquid 4.

[0558] (Preparation of dispersion liquid 5)

[0559] C.I. Pigment Blue 15:4 12.02 parts, a dispersing agent (BYK LPN-6919 manufactured by BYK Co.) 3.61 parts, a resin (B-1) (solid content conversion) 5.41 parts, diacetone alcohol 12.02 parts, and propylene glycol monomethyl ether acetate 66.94 parts were mixed, 300 parts of zirconium oxide beads of 0.4 mm were added, and oscillation was performed using a paint conditioner (manufactured by LAU Co.) for 1 hour. Then, the zirconium oxide beads were removed by filtration to obtain dispersion liquid 5.

[0560] (Preparation of dispersion liquid 6)

[0561] C.I. Pigment Blue 15:6 12.0 parts, a dispersing agent (BYK LPN-6919 manufactured by BYK Co.) 2.2 parts, a resin (B-1) (solid content conversion) 5.6 parts, diacetone alcohol 0.3 parts, and propylene glycol monomethyl ether acetate 79.9 parts were mixed, 300 parts of zirconium oxide beads of 0.4 mm were added, and oscillation was performed using a paint conditioner (manufactured by LAU Co.) for 1 hour. Then, the zirconium oxide beads were removed by filtration to obtain dispersion liquid 6.

[0562] (Preparation of dispersion liquid 7)

[0563] C.I. Pigment Yellow 150 12.0 parts, a dispersing agent (BYK LPN-6919 manufactured by BYK Co.) 2.4 parts, a resin (B-1) (solid content conversion) 5.2 parts, and propylene glycol monomethyl ether acetate 80.4 parts were mixed, 300 parts of zirconium oxide beads of 0.4 mm were added, and oscillation was performed using a paint conditioner (manufactured by LAU Co.) for 1 hour. Then, the zirconium oxide beads were removed by filtration to obtain dispersion liquid 7.

[0564] (Preparation of dispersion 8)

[0565] A mixture of 10.0 parts of C.I. Pigment Yellow 185, 3.5 parts of dispersant (BYK LPN-6919 manufactured by BYK), 3.5 parts of resin (B-1) (solid content conversion), and 83.0 parts of propylene glycol monomethyl ether acetate was prepared, 300 parts of zirconia beads of 0.4 mm were added, and the mixture was shaken for 1 hour using a paint shaker (manufactured by LAU). Then, the zirconia beads were removed by filtration to obtain dispersion 8.

[0566] (Preparation of dispersion 9)

[0567] A mixture of 5.0 parts of the compound represented by formula (8), 2.0 parts of dispersant (BYK LPN-6919 manufactured by BYK), 2.0 parts of resin (B-1) (solid content conversion), and 91.0 parts of propylene glycol monomethyl ether acetate was prepared, 300 parts of zirconia beads of 0.4 mm were added, and the mixture was shaken for 1 hour using a paint shaker (manufactured by LAU). Then, the zirconia beads were removed by filtration to obtain dispersion 9.

[0568] (Preparation of dispersion 10)

[0569] A mixture of 5.0 parts of the compound represented by formula (10), 2.0 parts of dispersant (BYK LPN-6919 manufactured by BYK), 2.0 parts of resin (B-1) (solid content conversion), and 91.0 parts of propylene glycol monomethyl ether acetate was prepared, 300 parts of zirconia beads of 0.4 mm were added, and the mixture was shaken for 1 hour using a paint shaker (manufactured by LAU). Then, the zirconia beads were removed by filtration to obtain dispersion 10.

[0570] (Preparation of dispersion 11)

[0571] A mixture of 5.0 parts of the compound represented by formula (15), 2.0 parts of dispersant (BYK LPN-6919 manufactured by BYK), 2.0 parts of resin (B-1) (solid content conversion), and 91.0 parts of propylene glycol monomethyl ether acetate was prepared, 300 parts of zirconia beads of 0.4 mm were added, and the mixture was shaken for 1 hour using a paint shaker (manufactured by LAU). Then, the zirconia beads were removed by filtration to obtain dispersion 11.

[0572] (Preparation of dispersion 12)

[0573] A mixture of 5.0 parts of the compound represented by formula (15), 2.0 parts of dispersant (BYK LPN-6919 manufactured by BYK), 2.0 parts of resin (B-1) (solid content conversion), and 91.0 parts of propylene glycol monomethyl ether acetate was prepared, 300 parts of zirconia beads of 0.4 mm were added, and the mixture was shaken for 1 hour using a paint shaker (manufactured by LAU). Then, the zirconia beads were removed by filtration to obtain dispersion 11.

[0574] Examples 8 to 16, Comparative Example 2

[0575] (Preparation of colored resin composition)

[0576] The components shown in Table 7 were mixed to obtain each colored resin composition.

[0577] [Table 7]

[0578]

[0579] In Table 7, each component was as follows.

[0580] Dispersion (A-1): Dispersion 1

[0581] Dispersion (A-2): Dispersion 2

[0582] Dispersion (A-3): Dispersion 3

[0583] Dispersion (A-4): Dispersion 4

[0584] Dispersion (A-5): Dispersion 5

[0585] Dispersion (A-6): Dispersion 6

[0586] Dispersion (A-7): Dispersion 7

[0587] Dispersion (A-8): Dispersion 8

[0588] Dispersion (A-9): Dispersion 9

[0589] Dispersion (A-10): Dispersion 10

[0590] Dispersion (A-11): Dispersion 11

[0591] Dispersion (A-12): Dispersion 12

[0592] Resin (B-1): Resin (B-1) (conversion of solid content)

[0593] Polymerizable compound (C-1): "A-9550" manufactured by Shin-Nakamura Chemical Co., Ltd. (conversion of solid content)

[0594] Polymerizable compound (C-2): "A-TMPT" manufactured by Shin-Nakamura Chemical Co., Ltd. (conversion of solid content)

[0595] Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylthio phenyl)-3-cyclohexylpropane-1-ketone-2-imine ("TR-PBG327" manufactured by Changzhou Qiangli Electronic New Material Co., Ltd.)

[0596] Solvent (E-1): propylene glycol monomethyl ether acetate

[0597] Solvent (E-2): diacetone alcohol

[0598] Leveling agent (F-1): polyether-modified silicone oil: trade name Toray Silicone SH8400: manufactured by Dow Corning Toray Co., Ltd. (solid content conversion)

[0599] Note that the solid content of the colored resin composition in Examples 8 to 16 and Comparative Example 2 was 12.0% respectively. In addition, the content of the colorant in the colored resin composition of Examples 8 to 16 and Comparative Example 2 was 15.0% respectively in the solid content of the colored resin composition.

[0600] (Production of the color filter (colored coating film))

[0601] The colored resin composition was applied to a 5 cm square glass substrate (EAGLE 2000; manufactured by Corning Inc.) by a spin coating method, and then prebaked at 90°C for 2 minutes to form a colored composition layer. After cooling, the colored composition layer was subjected to light irradiation under an atmosphere at an exposure amount of 1000 mJ / cm2(365 nm reference) using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). 2 Then, a postbaking was performed at 220°C for 5 minutes using a hot plate to obtain a color filter.

[0602] 〔Spectral evaluation〕

[0603] The color filter obtained was measured for a spectral distribution at intervals of 5 nm using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the spectrum after prebaking and the spectrum after postbaking were respectively calculated. The wavelength at which the maximum transmittance was 50% in the spectral data obtained was shown, and the wavelength (visible side T50 wavelength) present in the visible light region (400 to 700 nm) was calculated. The half value shift before and after postbaking was calculated based on the following formula. The results are shown in Table 8. The smaller the half value shift, the better the stability before and after postbaking can be said. If the visible side T50 wavelength before and after postbaking is slightly shifted, the color gamut can be affected (the target chromaticity cannot be achieved). Therefore, it can be said that the colored resin composition of the present application which can reduce the above half value shift to 5 nm or less (particularly 3 nm or less or 1 nm or less) is very meaningful in the field of color filters.

[0604] Half value shift (nm) = |visible side T50 wavelength after prebaking - visible side T50 wavelength after postbaking|

[0605] It should be noted that when the visible-side T50 wavelength exists between two measurement points, the visible-side T50 wavelength can be calculated from the measured values of the transmittances of the two measurement points using the TREND function.

[0606] [Table 8]

[0607] Half value offset Example 8 0 nm Example 9 1 nm Example 10 0 nm Example 11 1 nm Example 12 4 nm Example 13 5 nm Example 14 0 nm Example 15 3 nm Example 16 1 nm Comparative Example 2 7 nm

Claims

1. The compound represented by formula (I), In formula (I), X 1 ~X 8 Each can be independently represented as -OC2H5 or Br, and n1 to n8 can be independently represented as 0 or 1. Z 1 and Z 2 Each of the following groups can be represented independently. OH, or R 3 Represents the following groups, 2. A coloring resin composition comprising the compound and resin of claim 1.

3. The coloring resin composition according to claim 2, wherein, It 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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