Compounds

Abstract

The purpose of the present invention is to provide a compound and a colored resin composition with which it is possible to produce an optical filter having improved solvent resistance (preferably solvent resistance, heat resistance, and light resistance). It is also preferable to provide a compound and a colored resin composition with which it is possible to produce an optical filter in which the steepness of the slope on the long wavelength side from [lambda] max in the absorption spectrum in the wavelength range of 750-900 nm is improved. In the present invention, the compound is characterized by being represented by formula (I). [In formula (I), R1 represents an optionally substituted unsaturated aliphatic hydrocarbon group having 2-20 carbon atoms, and R2 represents a hydrogen atom, an optionally substituted hydrocarbon group having 1-20 carbon atoms, or a single bond connecting Z2 and R1. Z1 and Z2 each independently represent a single bond or an oxygen atom. ] # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a compound, a colored resin composition containing the compound, an optical filter formed from the colored resin composition, and a solid-state imaging device and a display device including the optical filter. Background Art

[0002] Optical filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma display panels, and solid-state imaging devices such as CCDs or CMOS sensors are manufactured from colored resin compositions. As a colorant used in such colored resin compositions, a compound represented by formula (x1) is known (Patent Document 1).

[0003]

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: Japanese Unexamined Patent Application Publication No. 2022-72558 Summary of the Invention

[0007] Optical filters are required to have excellent solvent resistance (preferably solvent resistance, heat resistance, and light resistance). However, it is known that when the compound represented by the above formula (x1) is used, the solvent resistance of the obtained optical filter is insufficient.

[0008] Therefore, an object of the present invention is to provide a compound and a colored resin composition capable of producing an optical filter with improved solvent resistance.

[0009] The gist of the present invention is as follows.

[0010] [1] A compound represented by formula (I).

[0011]

[0012] [In formula (I),

[0013] R 1 represents an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent,

[0014] R 2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a single bond connecting Z 2 to R 1 .

[0015] Z 1 and Z 2 each independently represent a single bond or an oxygen atom.

[0016] X1 to X 4 each independently represents -R 3 , -OR 3 , -SR 3 , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent.

[0017] R 3 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0018] n1 to n4 each independently represents an integer of 0 to 6.

[0019] [2] A colored resin composition comprising the compound described in [1] and a resin.

[0020] [3] The colored resin composition according to [2], further comprising at least one of a polymerizable compound and a polymerization initiator.

[0021] [4] An optical filter formed from the colored resin composition described in [2] or [3].

[0022] [5] A solid-state imaging device comprising the optical filter described in [4].

[0023] [6] A display device comprising the optical filter described in [4].

[0024] According to the present invention, a compound and a colored resin composition capable of producing an optical filter with improved solvent resistance (preferably solvent resistance, heat resistance, and light resistance) can be provided.

[0025] Furthermore, according to the present invention, in the wavelength range of 750 to 900 nm, the fall of the absorbance on the long-wavelength side from λ max in the absorption spectrum becomes steep (the steepness of the slope on the long-wavelength side from λ max is high), and the sensitivity when the optical filter is used in a solid-state imaging device for detecting near-infrared light can be improved. Detailed Description

[0026] <<Compound>>

[0027] The following shows a partial structure of the compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) to more specifically illustrate the present invention. According to the compound (I) of the present invention, the solvent resistance (preferably solvent resistance, heat resistance, and light resistance) can be improved in an optical filter formed from a colored resin composition containing the compound (I). Furthermore, it is preferred that the optical filter formed from the colored resin composition containing compound (I) has a steep fall in absorbance on the long-wavelength side from λ maxThe steepness of the slope on the long wavelength side starting from

[0028]

[0029] [In formula (I),

[0030] R 1 represents an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have substituents,

[0031] R 2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, or a single bond connecting Z 2 and R 1 is a single bond.

[0032] Z 1 and Z 2 each independently represent a single bond or an oxygen atom.

[0033] X 1 to X 4 each independently represent -R 3 -OR 3 -SR 3 a halogen atom, a nitro group, or a sulfamoyl group which may have substituents.

[0034] R 3 represents a hydrocarbon group having 1 to 20 carbon atoms which may have substituents.

[0035] [n1 to n4 each independently represent an integer from 0 to 6.]

[0036] R 1 The unsaturated aliphatic hydrocarbon group represented by has 2 to 20 carbon atoms, more preferably 2 to 15 carbon atoms, still more preferably 2 to 10 carbon atoms, and particularly preferably 2 to 8 carbon atoms.

[0037] R 1 The unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by may be linear or cyclic (alicyclic hydrocarbon group).

[0038] R 1The represented chain-like unsaturated aliphatic hydrocarbon group may be linear or branched. Specifically, examples include vinyl group, propenyl group (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylethenyl, butenyl group (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)ethenyl, 1-(1-methylethenyl)ethenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, pentenyl group (e.g., 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl), 1-(1,1-dimethylethyl)ethenyl, 1,3-dimethyl-1-butenyl, hexenyl group (e.g., 1-hexenyl, 5-hexenyl), heptenyl group (e.g., 1-heptenyl, 6-heptenyl), octenyl group (e.g., 1-octenyl, 7-octenyl), nonenyl group (e.g., 1-nonenyl, 8-nonenyl), decenyl group (e.g., 1-decenyl, 9-decenyl), undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group, icosene group, etc.;

[0039] ethynyl group, propynyl group (e.g., 1-propynyl, 2-propynyl), butynyl group (e.g., 1-butynyl, 2-butynyl, 3-butynyl), pentynyl group (e.g., 2-pentynyl, 3-pentynyl, 4-pentynyl), 1-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, hexynyl group (e.g., 2-hexynyl, 5-hexynyl), 1-ethyl-3-butynyl, heptynyl group (e.g., 2-heptynyl, 6-heptynyl), 1-ethyl-3-pentynyl, octynyl group (e.g., 1-octynyl, 2-octynyl, 7-octynyl), nonynyl group (e.g., 2-nonynyl, 8-nonynyl), decynyl group (e.g., 2-decynyl, 9-decynyl), undecynyl group, dodecynyl group, tridecynyl group, tetradecynyl group, pentadecynyl group, hexadecynyl group, heptadecynyl group, octadecynyl group, nonadecynyl group, icosynyl group, etc.

[0040] R 1 The represented unsaturated aliphatic chain hydrocarbon group (i.e., alkenyl group, alkynyl group) preferably has 2 to 15 carbon atoms, more preferably 2 to 10 carbon atoms, and still more preferably 2 to 8 carbon atoms.

[0041] As the unsaturated alicyclic hydrocarbon group represented by R 1 the following can be cited:

[0042] cyclohexenyl group (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl group, cyclooctenyl group, etc.

[0043] Norbornenyl and other unsaturated polycyclic hydrocarbon groups, etc.

[0044] R 1 The number of carbon atoms of the unsaturated alicyclic hydrocarbon group represented is preferably 3 to 10.

[0045] R 1 The unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R may have substituents.

[0046] As the substituent of the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R, there may be mentioned an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have substituents, a heterocyclic group which may have substituents, a halogen atom, a nitro group, a cyano group, -OR 1 、 -CO a1 、 -CO 2 R a1 、 -SR a1 、 -SO 2 R a1 、 -SO 3 R a1 、 -SO 2 、 -SO a1 NR a2 R a1 、 -NR a2 R

[0047] Among them, R a1 and R a2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. R a1 and R a2 The hydrocarbon group having 1 to 20 carbon atoms represented is the same as the hydrocarbon group having 1 to 20 carbon atoms represented by R 2 and R 3 described later.

[0048] As the aromatic hydrocarbon group having 6 to 20 carbon atoms which is used as the substituent of the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R, there may be mentioned: 1 、

[0049] 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 - bis(tert - butyl)phenyl, 3,5 - bis(tert - butyl)-4 - methylphenyl, 4 - n - 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, anthryl, 2 - dodecylphenyl, 3 - dodecylphenyl, 4 - dodecylphenyl, perylenyl, groups and pyrenyl and other aromatic hydrocarbon groups and the like.

[0050] The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 - 10, more preferably 6 - 8.

[0051] The aromatic hydrocarbon group may have substituents. Examples of the substituents include halogen atoms, nitro groups, cyano groups, -OR a1 , -CO 2 R a1 , -SR a1 , -SO 2 R a1 , -SO 3 R a1 , -SO 2 , -SO a1 R a2 and -NR a1 R a2 etc. (where R a1 and R a2 are the same as above).

[0052] The heterocyclic ring of the heterocyclic group that constitutes the substituent of the unsaturated aliphatic hydrocarbon group having 2 - 20 carbon atoms represented by R 1 can be a monocyclic ring or a polycyclic ring, and is preferably a heterocyclic ring containing a heteroatom as a ring - forming element. Examples of the heteroatom include nitrogen atoms, oxygen atoms, and sulfur atoms, etc.

[0053] As heterocycles containing only nitrogen atoms as heteroatoms, monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine, piperazine, etc. can be cited; five-membered ring unsaturated heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, etc.; six-membered ring unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, etc.; fused bicyclic heterocycles such as indazole, indoline, isoindoline, isoindoline-1,3-dione, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine, etc.; fused tricyclic heterocycles such as carbazole, acridine, phenazine, etc.

[0054] As heterocycles containing only oxygen atoms as heteroatoms, monocyclic saturated heterocycles such as ethylene oxide, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-di ane, 1,4-di ane, etc. can be cited; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane, etc.; lactone heterocycles such as α-ethyl lactone, β-propyl lactone, γ-butyl lactone, δ-valerolactone, etc.; five-membered ring unsaturated heterocycles such as furan, etc.; six-membered ring unsaturated heterocycles such as 2H-pyran, 4H-pyran, etc.; fused bicyclic heterocycles such as 1-benzofuran, benzopyran, benzodioxole, chromane, isochromane, etc.; fused tricyclic heterocycles such as xanthene, dibenzofuran, etc.

[0055] As heterocycles containing only sulfur atoms as heteroatoms, five-membered ring saturated heterocycles such as dithiolane, etc. can be cited; six-membered ring saturated heterocycles such as tetrahydrothiopyran, 1,3-dithiane, etc.; five-membered ring unsaturated heterocycles such as thiophene, etc.; six-membered ring unsaturated heterocycles such as 4H-thiopyran, etc.; fused bicyclic heterocycles such as benzotetrahydrothiopyran, benzothiopyran, benzothiophene, etc.; fused tricyclic heterocycles such as thianthrene, dibenzothiophene, etc.

[0056] As heterocycles containing nitrogen atoms and oxygen atoms as heteroatoms, monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-piperidone, etc. can be cited; azole, iso azole and other monocyclic unsaturated heterocycles; benzo azole, benzoiso azole, benzo azine, benzo dioxane, benzimidazoline and other fused bicyclic heterocycles; phen azine and other fused tricyclic heterocycles, etc.

[0057] As heterocycles containing nitrogen atoms and sulfur atoms as heteroatoms, monocyclic heterocycles such as thiazole, etc. can be cited; fused bicyclic heterocycles such as benzothiazole, etc.; fused tricyclic heterocycles such as phenothiazine, etc.

[0058] It should be noted that the heterocyclic group refers to a group in which any hydrogen atom contained in the above heterocycle is removed to form a bonding site.

[0059] The number of carbon atoms of the heterocyclic group is preferably 2 to 30, more preferably 3 to 22, and still more preferably 3 to 20.

[0060] The heterocyclic group may have a substituent. Examples of the substituent include a halogen atom, a nitro group, a cyano group, -OR a1 , -CO 2 R a1 , -SR a1 , -SO 2 R a1 , -SO 3 R a1 , -SO 2 , -SO a1 NR a2 R a1 R a2 etc. (wherein R a1 and R a2 are the same as above).

[0061] Examples of the halogen atom used as a substituent for the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R 1 , and the halogen atom used as a substituent for the above heterocyclic group include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.

[0062] R 2 and R 3 The hydrocarbon group having 1 to 20 carbon atoms represented by may be any of an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining them. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).

[0063] Examples of the saturated or unsaturated linear hydrocarbon group include: linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, and n-icosyl;

[0064] branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-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;

[0065] vinyl group, propenyl groups (such as 1-propenyl, 2-propenyl (allyl)), 1-methylethenyl, butenyl groups (such as 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)ethenyl, 1-(1-methylethenyl)ethenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, pentenyl groups (such as 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl), 1-(1,1-dimethylethyl)ethenyl, 1,3-dimethyl-1-butenyl, hexenyl groups (such as 1-hexenyl, 5-hexenyl), heptenyl groups (such as 1-heptenyl, 6-heptenyl), octenyl groups (such as 1-octenyl, 7-octenyl), nonenyl groups (such as 1-nonenyl, 8-nonenyl), decenyl groups (such as 1-decenyl, 9-decenyl), undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, icoseneyl, and the like;

[0066] Ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), butynyl (e.g., 1-butynyl, 2-butynyl, 3-butynyl), pentynyl (e.g., 2-pentynyl, 3-pentynyl, 4-pentynyl), 1-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, hexynyl (e.g., 2-hexynyl, 5-hexynyl), 1-ethyl-3-butynyl, heptynyl (e.g., 2-heptynyl, 6-heptynyl), 1-ethyl-3-pentynyl, octynyl (e.g., 1-octynyl, 2-octynyl, 7-octynyl), nonynyl (e.g., 2-nonyl, 8-nonyl), decynyl (e.g., 2-decynyl, 9-decynyl), undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecynyl, octadecynyl, nonadecynyl, icosynyl and other alkynyl groups such as etc.

[0067] The number of carbon atoms of the saturated acyclic hydrocarbon group (i.e., straight-chain alkyl group, branched-chain alkyl group) is preferably 1 to 10, more preferably 1 to 7, and still more preferably 1 to 5.

[0068] The number of carbon atoms of the unsaturated acyclic hydrocarbon group (i.e., alkenyl group, alkynyl group) is preferably 2 to 15, more preferably 2 to 10, and still more preferably 2 to 8.

[0069] Examples of the saturated or unsaturated alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl;

[0070] Cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl and cyclooctenyl;

[0071] Saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl, etc.

[0072] The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 10.

[0073] Examples of the aromatic hydrocarbon group include those used as R 1A group represented by an aromatic hydrocarbon group having 6 to 20 carbon atoms as a substituent of an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms.

[0074] The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 15, more preferably 6 to 10, and still more preferably 6 to 8.

[0075] R 2 and R 3 As long as the total number of carbon atoms of the hydrocarbon groups represented by R and R is 20 or less, they may be groups formed by combining the above-listed hydrocarbon groups. Examples of such groups include groups formed by combining at least one of an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group with an aromatic hydrocarbon group; groups formed by combining an aliphatic hydrocarbon group with an alicyclic hydrocarbon group, etc.

[0076] Examples of groups formed by combining at least one of an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group with an aromatic hydrocarbon group include:

[0077] Arylalkyl groups such as 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;

[0078] Arylene groups such as 1-phenylethenyl, 2-phenylethenyl (phenylethenyl), 2,2-diphenylethenyl, 2-phenyl-2-(1-naphthyl)ethenyl;

[0079] Arylalkynyl groups such as phenyl ethynyl, 3-phenyl-2-propynyl;

[0080] Phenyl groups having one or more phenyl groups bonded thereto, such as biphenyl and terphenyl;

[0081] Cyclohexylmethylphenyl, benzylphenyl, (dimethyl(phenyl)methyl)phenyl, etc.

[0082] The number of carbon atoms thereof is preferably 7 to 18, more preferably 7 to 15.

[0083] Examples of groups formed by combining an aliphatic hydrocarbon group with an alicyclic hydrocarbon group include alkyl groups having one or more alicyclic hydrocarbon groups bonded thereto, such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl)methyl, cyclohexylethyl, and adamantylmethyl. The number of carbon atoms thereof is preferably 4 to 15, more preferably 4 to 10.

[0084] R 2 and R 3 The hydrocarbon group having 1 to 20 carbon atoms represented by may have a substituent. Examples of the above-mentioned substituent include a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group, -OR a1 , -CO 2 R a1 , -SR a1 , -SO 2 R a1 , -SO 3 R a1 , -SO 2 NR a1 R a2 and -NR a1 R a2 etc. (wherein R a1 and R a2 are the same as those described above).

[0085] As the "heterocyclic group which may have a substituent" serving as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R 2 and R 3 , groups the same as the "heterocyclic group which may have a substituent" serving as a substituent of the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R 1 can be exemplified.

[0086] As the halogen atom serving as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R 2 and R 3 , fluorine atom, chlorine atom, bromine atom, iodine atom, etc. can be exemplified.

[0087] R 2 is a single bond connecting Z 2 and R 1 , a part or all of R 1 and *-Z 2 -P(=O)-Z 1 -* (* represents the bonding site) form a ring together. That is, when R 2 is a single bond connecting Z 2 and R 1 , a bond formed by sharing a pair of electrons between any carbon atom in the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent represented by R 1 and Z 2 corresponds to the single bond represented by R 2 .

[0088] When a part or all of R 1 and *-Z 2 -P(=O)-Z 1In the ring formed together with -* (* represents a bonding site), an unsaturated bond can be formed between carbon atoms that are members of the ring, an unsaturated bond can be formed between a carbon atom that is a member of the ring and a carbon atom outside the members of the ring, and an unsaturated bond can also be formed between carbon atoms outside the members of the ring.

[0089] As the group bonded to the bonding site in the above -* - Z 2 -P(=O)-Z 1 -* (* represents a bonding site), groups represented by the formulas (cy1) to (cy3) can be exemplified.

[0090]

[0091] [In the formula, R 15 ~R 16 independently represent a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, R 17 represents an unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms which may have a substituent, R 18 represents a hydrogen atom or a hydroxyl group. * represents a bonding site.]

[0092] As the hydrocarbon group having 1 to 8 carbon atoms which may have a substituent represented by R 15 ~R 16 groups in which the number of carbon atoms of the hydrocarbon group is 1 to 8 among the groups described for the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent represented by R 2 and R 3 can be exemplified. As the unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms which may have a substituent represented by R 17 groups in which the number of carbon atoms of the unsaturated aliphatic hydrocarbon group is 2 to 10 among the groups described for the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent represented by R 1 can be exemplified.

[0093] As R 15 ~R 16 , they are independently preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which may have a substituent.

[0094] As R 17 , it is preferably an alkenyl or alkynyl group having 2 to 10 carbon atoms which may have an aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0095] As the halogen atom represented by X 1 ~X 4 , fluorine atom, chlorine atom, bromine atom, iodine atom, etc. can be exemplified.

[0096] X 1~X 4 The sulfamoyl group represented is *-SO 2 -NH 2 (* indicates the bonding site).

[0097] X 1 ~X 4 The sulfamoyl group represented may have substituents. X 1 ~X 4 Examples of the substituents of the sulfamoyl group represented by X 1 ~X are the same as those of the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R a1 -CO 2 R a1 -SR a1 -SO 2 R a1 -SO 3 R a1 -SO 2 NR a1 R a2 and -NR a1 R a2 etc. (where R a1 and R a2 are the same as those above).

[0098] X 1 ~X 4 The -R 3 -OR 3 and -SR 3 represented by X 3 is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a saturated chain hydrocarbon group having 1 to 20 carbon atoms, still more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, and even more preferably a linear or branched alkyl group having 1 to 5 carbon atoms, particularly preferably methyl, ethyl, n-propyl, isopropyl, or tert-butyl.

[0099] The above R a1 and R a2 are each independently preferably a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0100] In formula (I), R 1 is preferably an unsaturated aliphatic chain hydrocarbon group having 2 to 20 carbon atoms that may have substituents (i.e., alkenyl, alkynyl),

[0101] More preferably, it is an unsaturated aliphatic chain hydrocarbon group having 2 to 10 carbon atoms which may have substituents.

[0102] In particular, from the viewpoint of further increasing the steepness of the slope from λ in the absorption spectrum of the obtained optical filter max onward, R 1 is preferably an alkynyl group having 2 to 20 carbon atoms which may have substituents, and more preferably an alkynyl group having 2 to 10 carbon atoms which may have substituents.

[0103] R 1 When the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by has substituents, as the substituents, an aromatic hydrocarbon group having 6 to 20 carbon atoms is preferred, an aromatic hydrocarbon group having 6 to 10 carbon atoms is more preferred, and a phenyl group is particularly preferred. That is, as R 1 , particularly preferred are an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have substituents, an arylene group having 8 to 20 carbon atoms which may have substituents, or an aryne group having 8 to 20 carbon atoms which may have substituents. As the substituents, halogen atoms, nitro groups, cyano groups, -OR a1 , -CO 2 R a1 , -SR a1 , -SO 2 R a1 , -SO 3 R a1 , -SO 2 NR a1 R a2 and -NR a1 R a2 etc. (wherein R a1 and R a2 are the same as above).

[0104] In formula (I), R 2 is preferably a hydrogen atom, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have substituents, an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have substituents, an arylene group having 8 to 20 carbon atoms which may have substituents, an aryne group having 8 to 20 carbon atoms which may have substituents, or a single bond connecting Z 2 and R 1 ,

[0105] More preferably, it is a hydrogen atom, an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have substituents, an unsaturated aliphatic chain hydrocarbon group having 2 to 10 carbon atoms which may have substituents, an arylene group having 8 to 15 carbon atoms which may have substituents, an aryne group having 8 to 15 carbon atoms which may have substituents, or a single bond connecting Z 2 and R 1The single bond.

[0106] Especially from the viewpoint of further improving the steepness of the slope starting from λ in the absorption spectrum of the obtained optical filter max starting, R 2 is preferably an alkynyl group having 2 to 20 carbon atoms which may have substituents, and more preferably an alkynyl group having 2 to 10 carbon atoms which may have substituents.

[0107] Especially when Z 1 and Z 2 are single bonds, and in the case where Z 1 is an oxygen atom and Z 2 is a single bond, preferably R 1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 20 carbon atoms which may have substituents, and R 2 is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have substituents; more preferably R 1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 10 carbon atoms which may have substituents, and R 2 is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have substituents.

[0108] In addition, when Z 1 and Z 2 are oxygen atoms, preferably R 1 and R 2 are unsaturated aliphatic chain hydrocarbon groups having 2 to 20 carbon atoms which may have substituents, or R 1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 20 carbon atoms which may have substituents, R 2 is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have substituents or a single bond connecting Z 2 and R 1 ; more preferably R 1 and R 2 are unsaturated aliphatic chain hydrocarbon groups having 2 to 10 carbon atoms which may have substituents, or R 1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 10 carbon atoms which may have substituents, R 2 is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have substituents or a single bond connecting Z 2 and R 1 .

[0109] Furthermore, when Z 1 is a single bond and Z 2 is an oxygen atom, preferably R 1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 20 carbon atoms which may have substituents, R 2is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have substituents or a hydrogen atom; more preferably, R 1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 10 carbon atoms which may have substituents, and R 2 is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have substituents or a hydrogen atom.

[0110] X 1 ~X 4 are each independently preferably -R 3 , -OR 3 or a halogen atom (particularly preferably in the case where the above R 3 is a saturated chain hydrocarbon group having 1 to 10 carbon atoms), more preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a halogen atom, and still more preferably a halogen atom.

[0111] n1 to n4 are each independently preferably 0, 1, 2 or 6.

[0112] In particular, from the viewpoint of further improving the solvent resistance of the obtained optical filter, n1 to n4 are each independently preferably an integer of 2 or less, more preferably 0 or 1.

[0113] In addition, from the viewpoint of further improving the heat resistance and light resistance of the obtained optical filter, n1 to n4 are each independently preferably an integer of 1 or more, more preferably 1, 2 or 6, and still more preferably 1 or 2.

[0114] In addition, from the viewpoint of further improving the steepness of the slope from λ max in the absorption spectrum of the obtained optical filter, n1 to n4 are each independently preferably an integer of 2 or less, more preferably 0.

[0115] As the naphthalene ring to which X 1 ~X 4 in formula (I) can be bonded, for example, the structures represented by formulas (t2-1) to (t2-10) can be cited. In the formula, m represents an integer of 1 to 5, and * represents the bonding site to the pyrrole ring in formula (I).

[0116]

[0117] The four naphthalene rings to which X 1 ~X 4 contained in compound (I) can be bonded may be the same or different, but are preferably the same.

[0118] As compound (I), specifically, compounds represented by the following formulas (I-1) to (I-10) can be cited, in which R 1 , R 2 , Z 1and Z 2 is a compound of any one of No.1 to 132 described in Tables 1 to 2. It should be noted that in the formula, n represents an integer of 1 to 5.

[0119]

[0120] [Table 1]

[0121]

[0122] [Table 2]

[0123]

[0124] It should be noted that in Tables 1 to 2, i-1 to i-22 respectively represent the groups represented by the following formulas (i-1) to (i-22), and ii-1 to ii-2 respectively represent the groups represented by the following formulas (ii-1) to (ii-2). In the following formulas, * represents the bonding site.

[0125]

[0126] *-H (ii-2)

[0127] Compound (I) can be produced, for example, by the following method. That is, a compound represented by formula (I') (hereinafter sometimes referred to as compound (I')) can be synthesized by appropriately reacting aluminum halide with a compound represented by formulas (ta1) to (ta4), and then the obtained compound (I') is appropriately reacted with a compound represented by formula (p1) to synthesize compound (I).

[0128]

[0129] [In the formula, R 1 ~R 2 、Z 1 ~Z 2 、X 1 ~X 4 and n1 to n4 have the same meanings as described above, and X represents a halogen atom.]

[0130] In addition, compound (I) can be synthesized by appropriately reacting aluminum halide with urea and a compound represented by formulas (tb1) to (tb4) to synthesize compound (I'), and then appropriately reacting the obtained compound (I') with a compound represented by formula (p1).

[0131]

[0132] [In the formula, R 1 ~R 2 、Z1 ~Z 2 、X 1 ~X 4 、n1 to n4 and X represent the same meanings as described above.

[0133] <<Colored Resin Composition>>

[0134] The present invention includes a colored resin composition containing the above compound (I) and a resin (hereinafter sometimes referred to as resin (B)).

[0135] The colored resin composition of the present invention preferably contains the above compound (I) as a colorant (hereinafter sometimes referred to as colorant (A)).

[0136] The colored resin composition of the present invention preferably further contains at least one of a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)).

[0137] The colored resin composition of the present invention preferably further contains a solvent (hereinafter sometimes referred to as solvent (E)).

[0138] The colored resin composition of the present invention may contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)).

[0139] In this specification, unless otherwise specified, the compounds exemplified as each component can be used alone or in combination of multiple kinds.

[0140] <Colorant (A)>

[0141] In the total amount of the solid components of the colored resin composition, the content rate of the compound (I) is preferably 0.5 to 70% by mass, more preferably 1 to 55% by mass, further preferably 2 to 50% by mass, and particularly preferably 8 to 40% by mass.

[0142] It should be noted that in this specification, the "total amount of solid components" refers to the total amount of components obtained by removing the solvent from the colored resin composition of the present invention. The total amount of solid components and the content of each component relative thereto can be measured by known analytical methods such as liquid chromatography and gas chromatography.

[0143] In addition, in the total amount of the colorant (A), the content rate of the compound (I) is preferably 20 to 100% by mass, more preferably 30 to 100% by mass, and further preferably 40 to 100% by mass. If the content rate of the compound (I) in the solid components of the colored resin composition or the colorant (A) is within the above range, it is easier to obtain the desired spectrum, and in addition, it is easy to improve the reliability such as heat resistance, light resistance, and solvent resistance.

[0144] In particular, when the optical filter formed from the colored resin composition of the present invention is used as a near-infrared transmission filter in a solid-state imaging device that senses near-infrared light, it is preferable to adjust the content ratio of the compound (I) in the colorant (A) to the above range. When the optical filter formed from the colored resin composition of the present invention is used as a color filter such as a primary color filter (RGB filter) or a complementary color filter (CMY filter), the content ratio of the compound (I) in the total amount of the colorant (A) can be 1 to 80% by mass, can be 2 to 50% by mass, or can be 3 to 30% by mass. By adjusting the content ratio of the compound (I) to the above range, the wavelength of the obtained color filter can be controlled.

[0145] The colorant (A) may further contain a colorant different from the compound (I) (hereinafter sometimes referred to as the colorant (A1)). The colorant (A1) can be either a dye or a pigment.

[0146] As dyes, for example, compounds classified in the Color Index (published by The Society of Dyers and Colourists) as substances having hues other than pigments, and known dyes described in the Dyeing Guide (Color Dyeing Co., Ltd.) can be cited.

[0147] As dyes, for example, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, thiazole dyes, azine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methylene dyes, azomethine dyes, squaric dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes, etc. Among these, organic solvent-soluble dyes are preferred.

[0148] As dyes, specifically, C.I. Solvent Yellow 4 (hereinafter, the description of C.I. Solvent Yellow is omitted, and only the number is recorded, and the same applies to others), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189,

[0149] C.I. Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247,

[0150] C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99,

[0151] C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60,

[0152] C.I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139,

[0153] C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 etc. C.I. Solvent Dyes;

[0154] 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,

[0155] C.I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426,

[0156] C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173,

[0157] C.I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102,

[0158] 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, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340,

[0159] 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 other C.I. acid dyes;

[0160] C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141,

[0161] 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,

[0162] C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107,

[0163] C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104,

[0164] 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, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293,

[0165] C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82 and other C.I. direct dyes;

[0166] C.I. Disperse Yellow 51, 54, 76,

[0167] C.I. Disperse Violet 26, 27,

[0168] C.I. Disperse Blue 1, 14, 56, 60 and other C.I. disperse dyes;

[0169] C.I. Basic Red 1, 9, 10,

[0170] 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, C.I. Basic Violet 2,

[0171] C.I. Basic Green 1 etc. C.I. basic dyes;

[0172] C.I. Reactive Yellow 2, 76, 116,

[0173] C.I. Reactive Orange 16,

[0174] C.I. Reactive Red 36 etc. C.I. reactive dyes;

[0175] C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65,

[0176] C.I. Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95,

[0177] 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,

[0178] 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,

[0179] 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,

[0180] C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other C.I. mordant dyes;

[0181] C.I. Vat Green 1 and other C.I. vat dyes.

[0182] These dyes can be used individually or in combination for each color, or dyes of different colors can be combined.

[0183] As pigments, for example, pigments classified as Pigment in the Color Index (published by The Society of Dyers and Colourists) can be cited.

[0184] As pigments classified as Pigment, for example, 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, 231 and other yellow pigments can be cited.

[0185] C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments.

[0186] C.I. Pigment Red 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273 and other red pigments.

[0187] C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments.

[0188] C.I. Pigment Violet 1, 19, 23, 32, 36, 38 and other purple pigments.

[0189] C.I. Pigment Green 7, 36, 58, 59, 62, 63 and other green pigments.

[0190] C.I. Pigment Brown 23, 25 and other brown pigments.

[0191] C.I. Pigment Black 1, 7 and other black pigments.

[0192] These pigments can use one pigment or multiple pigments for each color, or can combine pigments of various colors.

[0193] The pigments can be subjected to surface treatments such as rosin treatment as needed, surface treatment using pigment derivatives into which an acidic group or a basic group has been introduced, graft treatment of the pigment surface using a polymer compound, etc., micronization treatment by a sulfuric acid micronization method, etc., cleaning treatment using an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method, etc. The particle size of the pigments is preferably substantially uniform.

[0194] Relative to the total amount of the solid components, 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, still more preferably 2 to 55% by mass, and particularly preferably 8 to 50% by mass. If the content of the colorant (A) is within the above range, it is easier to obtain the desired spectral properties and color density.

[0195] <Resin (B)>

[0196] The resin (B) is not particularly limited, and an alkali-soluble resin is preferred. As the resin (B), the following resins [K1] to [K6] etc. can be mentioned.

[0197] Resin [K1]: A copolymer of at least one monomer (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)") and a monomer (b) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b)");

[0198] Resin [K2]: A copolymer of (a), (b), and a monomer (c) copolymerizable with (a) (wherein (c) is different from (a) and (b)) (hereinafter sometimes referred to as "(c)");

[0199] Resin [K3]: A copolymer of (a) and (c);

[0200] Resin [K4]: A resin obtained by reacting a copolymer of (a) and (c) with (b);

[0201] Resin [K5]: A resin obtained by reacting a copolymer of (b) and (c) with (a);

[0202] Resin [K6]: A resin obtained by reacting a copolymer of (b) and (c) with (a) and further reacting with a polycarboxylic acid and / or a carboxylic anhydride;

[0203] As (a), specifically, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, etc. can be mentioned;

[0204] 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-cyclohexenedicarboxylic acid;

[0205] 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;

[0206] 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;

[0207] Unsaturated mono-[(meth)acryloyloxyalkyl] esters of polycarboxylic acids with two or more carboxyl groups such as succinic acid mono[2-(meth)acryloyloxyethyl] ester, phthalic acid mono[2-(meth)acryloyloxyethyl] ester;

[0208] Unsaturated acrylic esters containing a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl) acrylate.

[0209] Among these, from the viewpoints of copolymerization reactivity and the solubility of the resulting resin in an alkaline aqueous solution, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred.

[0210] (b) refers to a polymerizable compound having a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from an ethylene oxide ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0211] It should be noted that in this specification, “(meth)acrylic acid” means at least one selected from acrylic acid and methacrylic acid. Expressions such as “(meth)acryloyl” and “(meth)acrylate” also have the same meaning.

[0212] As (b), for example, monomers (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), monomers (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), monomers (b3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), etc. can be cited.

[0213] As (b1), for example, monomers (b1-1) having a structure obtained by epoxidizing a linear or branched unsaturated aliphatic hydrocarbon (hereinafter sometimes referred to as "(b1-1)"), monomers (b1-2) having a structure obtained by epoxidizing an alicyclic unsaturated hydrocarbon (hereinafter sometimes referred to as "(b1-2)") can be cited.

[0214] As (b1-1), glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, etc. can be cited.

[0215] As (b1-2), vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, CYCLOMER A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, CYCLOMERM100; manufactured by Daicel Corporation), 3,4-epoxytricyclo[5.2.1.0 2,6 decyl ester, the compound represented by formula (R1) and the compound represented by formula (R2), etc. can be cited.

[0216]

[0217] [In formula (R1) and formula (R2), R ra and R rbrepresents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atoms contained in the alkyl group may be substituted with hydroxyl groups.

[0218] X ra and X rb represent a single bond, *-R rc -, *-R rc -O-, *-R rc -S- or *-R rc -NH-.

[0219] R rc represents an alkanediyl group having 1 to 6 carbon atoms.

[0220] * represents the bonding site to O.

[0221] Examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.

[0222] Examples of the alkyl group in which the hydrogen atom is substituted with a hydroxyl group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc.

[0223] As for R ra and R rb , preferably, a hydrogen atom, methyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl are selected, and more preferably, a hydrogen atom and methyl are selected.

[0224] Examples of the alkanediyl group include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, etc.

[0225] As for X ra and X rb , preferably, a single bond, methylene, ethylene, *-CH 2 -O- and *-CH 2 CH 2 -O- are selected, and more preferably, a single bond, *-CH 2 CH 2 -O- (* represents the bonding site to O).

[0226] As the compound represented by the formula (R1), compounds represented by any one of the formulas (R1-1) to (R1-15) can be cited. Among them, compounds represented by the formula (R1-1), the formula (R1-3), the formula (R1-5), the formula (R1-7), the formula (R1-9), or the formulas (R1-11) to (R1-15) are preferred, and compounds represented by the formula (R1-1), the formula (R1-7), the formula (R1-9), or the formula (R1-15) are more preferred.

[0227]

[0228]

[0229] As the compound represented by the formula (R2), compounds represented by any one of the formulas (R2-1) to (R2-15) can be cited. Among them, compounds represented by the formula (R2-1), the formula (R2-3), the formula (R2-5), the formula (R2-7), the formula (R2-9), or the formulas (R2-11) to (R2-15) are preferred, and compounds represented by the formula (R2-1), the formula (R2-7), the formula (R2-9), or the formula (R2-15) are more preferred.

[0230]

[0231] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloxymethyloxetane, 3-methyl-3-acryloxymethyloxetane, 3-ethyl-3-methacryloxymethyloxetane, 3-ethyl-3-acryloxymethyloxetane, 3-methyl-3-methacryloxyethyloxetane, 3-methyl-3-acryloxyethyloxetane, 3-ethyl-3-methacryloxyethyloxetane, 3-ethyl-3-acryloxyethyloxetane, etc.

[0232] As (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred. Specifically, examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0233] As (b), (b1) is preferred from the viewpoint of being able to further improve the reliability such as heat resistance and chemical resistance of the obtained optical filter. And (b1-2) is more preferred from the viewpoint of excellent storage stability of the colored resin composition.

[0234] As (c), for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 decane-8-yl (meth)acrylate (in the present technical field, it is commonly known as “dicyclopentyl (meth)acrylate”. In addition, it is sometimes referred to as “tricyclodecyl (meth)acrylate”), tricyclo[5.2.1.0 2,6 decene-8-yl (meth)acrylate (in the present technical field, it is commonly known as “dicyclopentenyl (meth)acrylate”), dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate and other (meth)acrylates;

[0235] (meth)acrylates containing hydroxyl groups such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

[0236] Diesters of dicarboxylic acids such as diethyl maleate, diethyl fumarate, and diethyl itaconate;

[0237] 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-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds;

[0238] 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 other dicarbonylimide derivatives;

[0239] Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.

[0240] 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, etc. are preferred, and from the viewpoints of copolymerization reactivity and heat resistance, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, etc. are more preferred.

[0241] In the resin [K1], among all the structural units constituting the resin [K1], the ratio of the structural units derived from each monomer is preferably:

[0242] Structural units derived from (a): 2 to 60 mol%,

[0243] Structural units derived from (b): 40 to 98 mol%,

[0244] More preferably:

[0245] Structural units derived from (a): 10 to 50 mol%,

[0246] Structural units derived from (b): 50 to 90 mol%.

[0247] If the ratio of the structural units of the resin [K1] is within the above range, there is a tendency for the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained optical filter to be more excellent.

[0248] The resin [K1] can be produced, for example, with reference to the methods described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Publishing Co., Ltd., 1st edition, 1st printing, issued on March 1, 1972) and the cited references in this literature.

[0249] Specifically, the following methods can be cited: By adding a specified amount of (a) and (b), a polymerization initiator, a solvent, etc. to a reaction vessel, forming a deoxidized atmosphere by replacing oxygen with nitrogen, for example, and heating and maintaining the temperature while stirring. It should be noted that the polymerization initiator and solvent used here are not particularly limited, and substances commonly used in the art can be used. For example, as the polymerization initiator, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.), organic peroxides (benzoyl peroxide, etc.) can be cited. As the solvent, as long as it can dissolve each monomer, solvents such as the solvent (E) described later can be cited.

[0250] It should be noted that the obtained copolymer can be used directly as the reaction solution, or a concentrated or diluted solution can be used, or a substance taken out in the form of a solid (powder) by methods such as reprecipitation can be used. In particular, by using the solvent contained in the colored resin composition as the solvent during this polymerization, the reaction solution can be directly used for the preparation of the colored resin composition, so the manufacturing process of the colored resin composition can be simplified.

[0251] In the resin [K2], among all the structural units constituting the resin [K2], the ratio of the structural units derived from each monomer is preferably:

[0252] Structural units from (a): 2 to 45 mol%,

[0253] Structural units from (b): 2 to 95 mol%,

[0254] Structural units from (c): 1 to 65 mol%,

[0255] More preferably:

[0256] Structural units from (a): 5 to 40 mol%,

[0257] Structural units from (b): 5 to 80 mol%,

[0258] Structural units from (c): 5 to 60 mol%.

[0259] If the ratio of the structural units of the resin [K2] is within the above range, there is a tendency for the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained optical filter to be more excellent.

[0260] The resin [K2] can be produced, for example, in the same manner as the method described for the production method of the resin [K1].

[0261] In the resin [K3], among all the structural units constituting the resin [K3], the ratio of the structural units from each monomer is preferably:

[0262] Structural units from (a): 2 to 60 mol%,

[0263] Structural units from (c): 40 to 98 mol%,

[0264] More preferably:

[0265] Structural units from (a): 10 to 50 mol%,

[0266] Structural units from (c): 50 to 90 mol%.

[0267] The resin [K3] can be produced, for example, in the same manner as the method described for the production method of the resin [K1].

[0268] 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 of (b) to the carboxylic acid and / or carboxylic anhydride of (a).

[0269] First, a copolymer of (a) and (c) is produced in the same manner as the method described for the production method of the resin [K1]. In this case, the ratio of the structural units from each monomer is preferably the same as the ratio listed in the resin [K3].

[0270] Next, a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the above copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms in (b).

[0271] After producing the copolymer of (a) and (c), the atmosphere in the flask is then replaced from nitrogen to air, and (b), a reaction catalyst for the carboxylic acid or carboxylic anhydride and the cyclic ether (such as tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (such as hydroquinone, etc.) are added to the flask. Then, for example, the reaction is carried out at 60 to 130 °C for 1 to 10 hours to produce Resin [K4].

[0272] With respect to 100 moles of (a), the usage amount of (b) is preferably 5 to 80 moles, more preferably 10 to 75 moles. By being in this range, there is a tendency for the balance of the storage stability of the colored resin composition, the developability during pattern formation, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern to become good. From the perspective that the cyclic ether has high reactivity and it is not easy to leave unreacted (b), as (b) used in Resin [K4], (b1) is preferred, and (b1-1) is further preferred.

[0273] With respect to 100 parts by mass of the total of (a), (b), and (c), the usage amount of the above reaction catalyst is preferably 0.001 to 5 parts by mass. With respect to 100 parts by mass of the total of (a), (b), and (c), the usage amount of the above polymerization inhibitor is preferably 0.001 to 5 parts by mass.

[0274] Reaction conditions such as the feeding method, reaction temperature, and time can be appropriately adjusted in consideration of the manufacturing equipment, the heat generated by polymerization, etc. It should be noted that, similarly to the polymerization conditions, the feeding method and reaction temperature can be appropriately adjusted in consideration of the manufacturing equipment, the heat generated by polymerization, etc.

[0275] For Resin [K5], as the first step, a copolymer of (b) and (c) is obtained in the same manner as the manufacturing method of the above Resin [K1]. Similarly to the above, the obtained copolymer can directly use the solution after the reaction, or can use the concentrated or diluted solution, or can also use the substance taken out in the form of a solid (powder) by methods such as reprecipitation.

[0276] With respect to the total molar number of all structural units constituting the above copolymer, the ratios of the structural units derived from (b) and (c) are respectively preferably:

[0277] Structural units derived from (b): 5 to 95 mol%,

[0278] Structural units derived from (c): 5 to 95 mol%,

[0279] More preferably:

[0280] Structural units from (b): 10 to 90 mol%

[0281] Structural units from (c): 10 to 90 mol%.

[0282] In addition, resin [K5] can be obtained by reacting the cyclic ether from (b) in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride of (a) under the same conditions as the production method of resin [K4].

[0283] The amount of (a) used for reacting with the above copolymer is preferably 5 to 100 mol relative to 100 mol of (b). From the perspective that the cyclic ether has high reactivity and it is not easy to leave unreacted (b), as (b) used in resin [K5], (b1) is preferred, and (b1-1) is more preferred.

[0284] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic anhydride. The hydroxyl group generated from the reaction of the cyclic ether with the carboxylic acid or carboxylic anhydride is reacted with the carboxylic anhydride.

[0285] Examples of the carboxylic anhydride include 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-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic anhydride used is preferably 0.1 to 1 mol relative to 1 mol of the amount of (a) used.

[0286] As specific resin (B), examples include (meth)acrylic acid 3,4-epoxycyclohexylmethyl ester / (meth)acrylic acid copolymer, acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 decyl ester / (meth)acrylic acid copolymer and other resins [K1]; acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 decyl ester / (meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer, (meth)acrylic acid glycidyl ester / (meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer, (meth)acrylic acid glycidyl ester / styrene / (meth)acrylic acid copolymer, acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6Resins such as decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(methacryloyloxymethyl)oxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins such as the resin obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, the resin obtained by adding glycidyl (meth)acrylate to tricyclodecanyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, the resin obtained by adding glycidyl (meth)acrylate to tricyclodecanyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer [K4]; resins such as the resin obtained by reacting a copolymer of tricyclodecanyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, the resin obtained by reacting a copolymer of tricyclodecanyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid [K5]; resins such as the resin obtained by further reacting the resin obtained by reacting a copolymer of tricyclodecanyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid with tetrahydrophthalic anhydride, the resin obtained by further reacting the resin obtained by reacting a copolymer of 2-ethylhexyl (meth)acrylate / glycidyl (meth)acrylate / dicyclopentanyl (meth)acrylate with (meth)acrylic acid with succinic anhydride [K6], etc.

[0287] Among them, as the resin (B), a copolymer (resin [K1] or resin [K2]) containing a structural unit derived from at least 1 kind selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit having a cyclic ether structure and an ethylenic unsaturated bond with 2 to 4 carbon atoms, or resin [K6] is preferred, and resin [K1] or resin [K2] is more preferred.

[0288] The polystyrene-reduced weight-average molecular weight of the resin (B) is preferably 500 to 100,000, more preferably 600 to 50,000, and still more preferably 700 to 30,000. If the molecular weight is within the above range, there is a tendency to improve the hardness of the optical filter, high residual film ratio, good solubility of the unexposed portion in the developer, and improved resolution of the colored pattern.

[0289] The dispersity [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.

[0290] The acid value of resin (B) in terms of solid content is preferably 10 to 170 mg-KOH / g, more preferably 20 to 150 mg-KOH / g, and still more preferably 30 to 135 mg-KOH / g. Here, the acid value is the value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0291] The content rate of resin (B) relative to the total amount of the solid content of the colored resin composition is preferably 7 to 80% by mass, more preferably 13 to 75% by mass, still more preferably 17 to 70% by mass, and even more preferably 17 to 55% by mass. When the content rate of resin (B) is within the above range, there is a tendency that a colored pattern can be formed and the resolution and residual film rate of the colored pattern are improved.

[0292] In addition, the content of compound (I) relative to 100 parts by mass of resin (B) is preferably 1 to 100 parts by mass, more preferably 8 to 70 parts by mass, and still more preferably 15 to 50 parts by mass.

[0293] <Polymerizable compound (C)>

[0294] The polymerizable compound (C) is a compound capable of polymerizing by active radicals and / or acids generated by a polymerization initiator (D). For example, compounds having a polymerizable ethylenically unsaturated bond can be cited, and (meth)acrylate compounds are preferred.

[0295] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylate (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylate (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylate (e.g., tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylate (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl) isocyanurate, alkoxylated pentaerythritol poly(meth)acrylate (e.g., ethoxylated pentaerythritol tri(meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, propoxylated pentaerythritol tri(meth)acrylate, propoxylated pentaerythritol tetra(meth)acrylate), alkoxylated dipentaerythritol poly(meth)acrylate (e.g., ethoxylated dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol penta(meth)acrylate, propoxylated dipentaerythritol hexa(meth)acrylate), caprolactone-modified pentaerythritol poly(meth)acrylate (e.g., caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylate (e.g., caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate), etc.

[0296] Among them, it is preferably to contain at least one selected from trimethylolpropane tri(meth)acrylate and dipentaerythritol poly(meth)acrylate, and more preferably to contain at least one selected from trimethylolpropane triacrylate and dipentaerythritol polyacrylate.

[0297] The weight-average molecular weight of the polymerizable compound (C) is preferably 150 to 2900, and more preferably 250 to 1500.

[0298] With respect to the total amount of the solid components of the colored resin composition, the content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 55% by mass. If the content of the polymerizable compound (C) is within the above range, there is a tendency that the residual film rate when forming a colored pattern and the chemical resistance of the optical filter are further improved.

[0299] <Polymerization initiator (D)>

[0300] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active free radicals, acids, etc. by the action of light or heat to initiate polymerization, and known polymerization initiators can be used.

[0301] Examples of the polymerization initiator that generates active free radicals include alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds.

[0302] The above O-acyl oxime compound is a compound having a partial structure represented by the formula (d1). Hereinafter, * represents a bonding site.

[0303]

[0304] As the above O-acyl oxime compounds, for example, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxocyclopentylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[4-(2-hydroxyethyloxy)phenylthiophenyl]propane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetoxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one and the like can be mentioned. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, PBG-329 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) and the like can be used. Among them, the O-acyl oxime compound is preferably at least one selected from N-acetoxy-1-[4-(2-hydroxyethyloxy)phenylthiophenyl]propane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetoxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and more preferably at least one selected from 2-[(acetoxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine. If these O-acyl oxime compounds are used, there is a tendency to obtain an optical filter with high brightness.

[0305] The above alkyl phenyl ketone compounds are compounds having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have substituents.

[0306]

[0307] Examples of the compounds having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylthiophenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907, 379 (manufactured by BASF above) can be used.

[0308] Examples of the compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, benzil dimethyl ketal, etc.

[0309] From the perspective of sensitivity, as the alkyl phenyl ketone compound, a compound having a partial structure represented by formula (d2) is preferred.

[0310] Examples of the above triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0311] As the above-mentioned acylphosphine oxide compound, 2,4,6-trimethylbenzoyl diphenylphosphine oxide etc. can be cited. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can be used.

[0312] As the above-mentioned benzimidazole compound, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(alkoxyphenyl)benzimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)benzimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)benzimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Laid-Open No. 62-174204, etc.), benzimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carbalkoxy groups (for example, refer to Japanese Patent Laid-Open No. 7-10913, etc.) etc.

[0313] In addition, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, etc. can be cited; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, etc.; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, camphorquinone, etc.; 10-butyl-2-chloroacridone, benzil, methyl phenylglyoxylate, titanocene compounds, etc. They are preferably used in combination with the polymerization initiator assistant (D1) (especially amines) described later.

[0314] As the polymerization initiator that generates acid, for example, 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, etc. salts, nitrobenzyl p-toluenesulfonates, benzoin p-toluenesulfonates, etc.

[0315] As the polymerization initiator (D), a polymerization initiator containing at least one selected from alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds is preferred, and a polymerization initiator containing an O-acyl oxime compound is more preferred.

[0316] With respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C), the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass. If the content of the polymerization initiator (D) is within the above range, there is a tendency to increase the sensitivity and shorten the exposure time, and thus the productivity of the optical filter is improved.

[0317] <Polymerization initiator assistant (D1)>

[0318] The polymerization initiator assistant (D1) is a compound or sensitizer for promoting the polymerization of the polymerizable compound polymerized by the polymerization initiator. When the polymerization initiator assistant (D1) is included, it is usually used in combination with the polymerization initiator (D).

[0319] Examples of the polymerization initiator assistant (D1) include amine compounds, alkoxy anthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0320] Examples of the above amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc., and 4,4'-bis(diethylamino)benzophenone is preferred among them. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) can also be used.

[0321] Examples of the above alkoxy anthracene compounds include 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.

[0322] Examples of the above thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, etc.

[0323] Examples of the carboxylic acid compound include 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.

[0324] When using these polymerization initiation aids (D1), its content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and there is a tendency to improve the productivity of the optical filter.

[0325] <Solvent (E)>

[0326] The solvent (E) is not particularly limited, and solvents commonly used in the art can be used. For example, ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. can be mentioned.

[0327] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexyl acetate, and γ-butyrolactone, etc.

[0328] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole, etc. Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole, etc.

[0329] Examples of the ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 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, and diethylene glycol monobutyl ether acetate.

[0330] Examples of the ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0331] Examples of the alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0332] Examples of the aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0333] Examples of the amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0334] Among the above solvents, from the viewpoints of coatability and drying property, an organic solvent having a boiling point of 120°C to 180°C at 1 atm is preferred. As the solvent, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide are preferred, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate, and ethyl 3-ethoxypropionate are more preferred.

[0335] The content rate of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on 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, more preferably 8 to 25% by mass. When the content rate of the solvent (E) is within the above range, the flatness during coating becomes good, and the color density is not insufficient when forming an optical filter, so there is a tendency for the display characteristics and sensitivity to become good.

[0336] <Levelling agent (F)>

[0337] Examples of the leveling agent (F) include silicone surfactants, fluorosurfactants, and silicone surfactants having fluorine atoms, etc. They may have a polymerizable group in the side chain.

[0338] Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule, etc. 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 Co., Ltd.) etc.

[0339] Examples of the above-mentioned fluorosurfactant include surfactants having a fluorocarbon chain in the molecule, etc. Specifically, FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Limited), 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 Corporation), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by AGC Inc. (formerly known as Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.) etc.

[0340] Examples of the organosilicon surfactant having a fluorine atom as described above include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, examples include MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation).

[0341] The content rate of the leveling agent (F) is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, and still more preferably 0.005 to 0.05% by mass, relative to the total amount of the colored resin composition. It should be noted that this content rate does not include the content rate of the pigment dispersant described later. If the content rate of the leveling agent (F) is within the above range, the flatness of the optical filter can be made good.

[0342] <Other components>

[0343] The colored resin composition may contain, as needed, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and other additives known in the art.

[0344] <Method for producing colored resin composition>

[0345] The colored resin composition can be prepared, for example, by mixing the colorant (A), the resin (B), and, as needed, the polymerizable compound (C), the polymerization initiator (D), the solvent (E), the leveling agent (F), the polymerization initiator auxiliary (D1), and other components. It is preferable to filter the mixed colored resin composition through a filter having a pore size of about 0.01 to 10 μm.

[0346] The compound (I) as the colorant (A) and the pigment used as needed can be used in the form of a dispersion in a state of being uniformly dispersed in a solution by being dispersed using a pigment dispersant. The target colored resin composition can be prepared by mixing the remaining components in such a dispersion to a prescribed concentration. The compound (I) and the pigment can be dispersed separately or a plurality of them can be mixed and dispersed.

[0347] As a pigment dispersant, surfactants etc. can be cited, and any of cationic, anionic, nonionic and amphoteric surfactants can be used. Specifically, surfactants such as polyester-based, polyamine-based and acrylic-based surfactants etc. can be cited. These dispersants can be used alone or in combination of two or more. When represented by trade names as the dispersant, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Inc.), Disperbyk (registered trademark), BYK (registered trademark) (manufactured by BYK-Chemie) etc. can be cited.

[0348] When using the pigment dispersant, its usage amount is preferably 10 to 200 parts by mass, more preferably 15 to 180 parts by mass, still more preferably 20 to 160 parts by mass with respect to 100 parts by mass of the compound (I) and the pigment in the dispersion liquid. If the usage amount of the pigment dispersant is within the above range, there is a tendency to obtain a dispersion liquid with a more uniform dispersion state.

[0349] In addition, when the colorant (A) contains a dye, the dye can be previously dissolved in a part or all of the solvent (E) to prepare a solution. It is preferable to filter this solution through a filter with a pore size of about 0.01 to 1 μm.

[0350] [Optical filter]

[0351] As a method for forming a pattern of an optical filter from the colored resin composition of the present invention, photolithography, inkjet method, printing method etc. can be cited. Among them, photolithography is preferred. Photolithography is a method of coating the above-mentioned colored resin composition on a substrate and drying it to form a composition layer, and then exposing and developing the composition layer through a photomask. In photolithography, a coating film which is a cured product of the above-mentioned composition layer can be formed by not using a photomask and / or not performing development during exposure.

[0352] The film thickness of the optical filter is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, still more preferably 3 μm or less, even more 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, still more preferably 0.3 μm or more.

[0353] As the substrate, glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass with a silica coating on the surface, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, and substrates with aluminum, silver, silver / copper / palladium alloy thin films, etc. formed on the above substrates can be used. Other optical filter layers, resin layers, transistors, circuits, etc. can be formed on these substrates. In addition, a substrate subjected to HMDS treatment on a silicone substrate can be used.

[0354] The formation of a coating film or pattern by photolithography can be carried out under known or conventional devices and conditions. For example, it can be made as follows. First, the colored resin composition is coated on the substrate, and heated and dried (pre-baked) and / or dried under reduced pressure to remove volatile components such as solvents to make it dry, obtaining a smooth composition layer. As the coating method, spin coating method, slit coating method, slit and spin coating method, etc. can be cited. The temperature during heating and drying is preferably 30 to 120 °C, more preferably 50 to 110 °C. In addition, as the heating time, it is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying under reduced pressure, it is preferably carried out in the temperature 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 according to the film thickness of the target optical filter.

[0355] Next, the composition layer can be exposed through a photomask for forming the target pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the intended use can be used. As the light source used in the exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferred. For example, light with a wavelength less than 250 nm can be cut off using a filter that cuts off this wavelength range, or light near 436 nm, near 408 nm, near 365 nm can be selectively extracted using a band-pass filter that extracts these wavelength ranges. Specifically, mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, etc. can be cited. In order to be able to uniformly irradiate parallel light on the entire exposure surface, or to perform precise alignment of the photomask and the substrate, it is preferred to use a reduction projection exposure device or a proximity exposure device such as a mask aligner and a stepper.

[0356] The exposed composition layer is developed by contacting it with a developer, thereby forming a pattern on the substrate. The unexposed portion of the composition layer is dissolved in the developer and removed by development. 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 of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. In addition, the developer can contain a surfactant. The development method can be any one of the paddle method, dipping method, and spraying method, etc. And, the substrate can be tilted at an arbitrary angle during development.

[0357] After development, it is preferably washed with water.

[0358] In addition, it is preferable to perform post-baking on the obtained pattern or coating film. 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.

[0359] The patterns and coating films thus obtained are useful as optical filters and can be applied to color filters such as near-infrared transmission filters, primary color filters (RGB filters), and complementary color filters (CMY filters) used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging elements, etc.

[0360] In particular, in recent years, there has been research on using solid-state imaging elements that sense near-infrared rays in cameras, sensors, etc. such as smartphones, surveillance cameras, in-vehicle cameras, cameras for IoT (Internet of Things), and infrared sensors. The optical filter formed from the coloring resin composition of the present invention preferably has a steep drop in absorbance on the long-wavelength side from λ max onward in the wavelength range of 750 to 900 nm (the steepness of the slope on the long-wavelength side from λ max onward is high). The higher the steepness of this slope, the easier it is to increase the light absorbency in the visible region (especially the long-wavelength side of the visible region). As a result, the sensitivity to near-infrared rays becomes high, so it can be suitably used as a near-infrared transmission filter in solid-state imaging elements. In addition, the higher the steepness of the above slope, the better the sensitivity can be in the vicinity of 940 nm where the influence of sunlight is small, so it can be suitably used as a near-infrared transmission filter in solid-state imaging elements that are not easily affected by near-infrared rays generated by the sun.

[0361] Examples

[0362] Examples are given below to illustrate the present invention more specifically. However, the present invention is obviously not limited by the following examples. Of course, it can be appropriately modified and implemented within the scope suitable for the foregoing and following gists, and all of these are included in the technical scope of the present invention. It should be noted that hereinafter, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

[0363] The structure of the compound was confirmed by mass spectrometry (MALDI-TOF MS; JMS-S3000 manufactured by JEOL Ltd.).

[0364] The measurement of the polystyrene-reduced weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin was carried out by the GPC method under the following conditions.

[0365] Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)

[0366] Column: TSK-GEL G2000HXL

[0367] Column temperature: 40 °C

[0368] Solvent: Tetrahydrofuran

[0369] Flow rate: 1.0 mL / min

[0370] Solid component concentration of the analysis sample: 0.001 - 0.01 mass %

[0371] Injection volume: 50 μL

[0372] Detector: RI

[0373] Standard substance for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0374] The ratio (Mw / Mn) of the weight-average molecular weight to the number-average molecular weight in terms of polystyrene obtained above is defined as the dispersity.

[0375] [Synthesis of the colorant]

[0376] (Example 1: Synthesis of compound (3))

[0377] <Preparation of compound (1)>

[0378] Under a nitrogen atmosphere, 1.0 part of aluminum chloride (manufactured by Fujifilm Wako Chemicals Corporation), 4.0 parts of 2,3-dicyanonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.6 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) and 15 parts of 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150 °C and stirred for 20 hours. After cooling the reaction solution to room temperature, 75 parts of ethyl acetate was added. The precipitate obtained was collected in the form of the residue by suction filtration, washed with 75 parts of ethyl acetate and then washed with 150 parts of ion-exchanged water. The resulting residue was dried under reduced pressure at 60 °C to obtain 3.5 parts of the compound represented by formula (1) (hereinafter referred to as compound (1)).

[0379]

[0380] Identification of compound (1)

[0381] (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z = 774

[0382] Exact mass: 774

[0383] <Preparation of Compound (2)>

[0384] The compound represented by formula (2) (hereinafter referred to as compound (2)) was obtained in the same manner as the synthesis method of the compound represented by formula (8) described in Example 4 of International Publication No. 2022 / 024926.

[0385]

[0386] <Preparation of Compound (3)>

[0387] 1.0 part of compound (1), 0.3 part of compound (2), and 5.0 parts of propylene glycol monomethyl ether acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, and the temperature was raised to 150 °C and stirred for 10 hours. After the reaction solution was cooled to room temperature, 50 parts of ethyl acetate was added. The precipitate obtained was collected as the residue by suction filtration and washed with 50 parts of ethyl acetate. After adding 50 parts of ethyl acetate to the obtained residue and stirring, the residue was filtered and washed with 50 parts of ethyl acetate. The obtained residue was dried under reduced pressure by heating at 60 °C to obtain 1.0 part of the compound represented by formula (3) (hereinafter referred to as compound (3)).

[0388]

[0389] Identification of Compound (3)

[0390] (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z = 940

[0391] Exact mass: 940

[0392] (Example 2: Synthesis of Compound (6))

[0393] <Preparation of Compound (4)>

[0394] The compound represented by formula (4) (hereinafter referred to as compound (4)) was obtained in the same manner as the synthesis method of the compound represented by formula (6) described in Example 3 of International Publication No. 2022 / 024926.

[0395]

[0396] <Preparation of Compound (5)>

[0397] The 1-chloronaphthalene, urea, 4-fluorophthalonitrile, and aluminum trichloride used as raw materials were changed to 2.1 parts of 1-chloronaphthalene, 0.008 parts of urea, 1.0 part of 2,3-dibromo-6,7-dicyanonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), and 0.11 part of aluminum trichloride. Except for this, the compound represented by formula (5) (hereinafter referred to as compound (5)) was synthesized by the same method as described in

[0071] to

[0072] of Japanese Patent Application Laid-Open No. 2012-507743.

[0398]

[0399] Identification of Compound (5)

[0400] (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z = 1397

[0401] Exact mass: 1397

[0402] <Preparation of Compound (6)>

[0403] 0.062 part of compound (4) and 3.5 parts of NMP were mixed at room temperature. After heating to 50°C, 0.35 part of compound (5) was added, and the temperature was raised to 150°C and stirred for 10 hours. After cooling the reaction solution to room temperature, the obtained reaction solution was added to 35 parts of ion-exchanged water. The obtained precipitate was obtained in the form of the residue by suction filtration, washed with 20 parts of ion-exchanged water, and dried under reduced pressure at 60°C to obtain 0.32 part of the compound represented by formula (6) (hereinafter referred to as compound (6)).

[0404]

[0405] Identification of Compound (6)

[0406] (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z = 1567

[0407] Exact mass: 1567

[0408] (Example 3: Synthesis of Compound (8))

[0409] <Preparation of Compound (7)>

[0410] Change 1-chloronaphthalene, urea, 4-fluorophthalonitrile, and aluminum trichloride, which are used as raw materials, to 4.0 parts of 1-chloronaphthalene, 0.015 parts of urea, 1.5 parts of 6-bromo-2,3-dicyanonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), and 0.20 parts of aluminum trichloride. Except for this, synthesize the compound represented by formula (7) by the same method as the method described in

[0071] to

[0072] of Japanese Patent Application Laid-Open No. 2012-507743.

[0411]

[0412] Identification of Compound (7)

[0413] (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z = 1086

[0414] Exact mass: 1086

[0415] <Preparation of Compound (8)>

[0416] Mix 0.18 part of Compound (4) and 8.0 parts of NMP at room temperature. After heating to 50°C, add 0.80 part of Compound (7), heat to 150°C, and stir for 10 hours. After cooling the reaction solution to room temperature, add the obtained reaction solution to 80 parts of ion-exchanged water. Obtain the precipitate in the form of the residue by suction filtration, wash it with 25 parts of ion-exchanged water, and then perform drying under reduced pressure at 60°C to obtain 0.98 part of the compound represented by formula (8) (hereinafter referred to as Compound (8)).

[0417]

[0418] Identification of Compound (8)

[0419] (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z = 1256

[0420] Exact mass: 1256

[0421] (Comparative Example 1: Synthesis of Compound (x1))

[0422] Obtain the compound represented by formula (x1) (hereinafter referred to as Compound (x1)) by the synthesis method described in Japanese Patent Application Laid-Open No. 2022-72558.

[0423]

[0424] Identification of Compound (x1)

[0425] (Mass spectrometry) Ionization mode = MALDI-TOF -: m / z = 988

[0426] Exact mass: 988

[0427] [Synthesis of resin]

[0428] (Preparation of resin (B-1))

[0429] An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen. 340 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80 °C with stirring. Next, a mixed solution of 57 parts of acrylic acid, 54 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 decane-9-yl acrylate (containing a molar ratio of 1:1), and 239 parts of benzyl methacrylate and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, an initiator solution prepared by dissolving 40 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition of the initiator solution was completed, the mixture was maintained at 80 °C for 3 hours and then cooled to room temperature (18 - 24 °C) to obtain a copolymer (resin (B-1)) solution having a viscosity of 127 mPas measured with a B-type viscometer (23 °C) and a solid content of 37.0%. The weight-average molecular weight Mw of the resulting copolymer was 9.4×10 3 , the dispersity was 1.89, and the acid value in terms of solid content was 114 mg-KOH / g. Resin (B-1) has the following structural units.

[0430]

[0431] [Preparation of dispersion liquid]

[0432] (Production example 1 of dispersion liquid)

[0433] 5 parts of the compound (3) obtained in Example 1, 3 parts of a dispersant (BYKLPN-6919 manufactured by BYK) (in terms of solid content), 3 parts of resin (B-1) (in terms of solid content), and 89 parts of propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.2 μm zirconia beads were added, and the mixture was shaken for 0.5 hours using a paint disperser (manufactured by LAU). Thereafter, the zirconia beads were removed by filtration to obtain a dispersion liquid (A-1).

[0434] (Production examples 2 - 3 of dispersion liquid)

[0435] The compound (3) obtained in Example 1 was changed to the following compounds, and dispersion liquids (A-2) - (A-3) were obtained in the same manner as in Production example 1 of dispersion liquid except for this.

[0436] Preparation Example 2 of Dispersion (Preparation of Dispersion (A-2)): Compound (6) obtained in Example 2

[0437] Preparation Example 3 of Dispersion (Preparation of Dispersion (A-3)): Compound (8) obtained in Example 3

[0438] (Preparation Example 4 of Dispersion)

[0439] 5 parts of Compound (x1) obtained in Comparative Example 1, 4 parts of dispersant (BYK LPN-6919 manufactured by BYK) (in terms of solid content), 4 parts of resin (B-1) (in terms of solid content), and 87 parts of propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.2 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint disperser (manufactured by LAU). Thereafter, the zirconia beads were removed by filtration to obtain Dispersion (X-1).

[0440] (Example 1A)

[0441] <Preparation of Colored Resin Composition 1>

[0442] Colored Resin Composition 1 was obtained by mixing the following components.

[0443] Dispersion (A-1)

[0444] 415 parts

[0445] Resin (B-1) (in terms of solid content)

[0446] 48 parts

[0447] Polymerizable Compound (C-1): Dipentaerythritol polyacrylate, trade name A-9550, manufactured by Shin-Nakamura Chemical Co., Ltd.

[0448] 20 parts

[0449] Polymerizable Compound (C-2): Trimethylolpropane triacrylate, trade name A-TMPT, manufactured by Shin-Nakamura Chemical Co., Ltd.

[0450] 20 parts

[0451] Polymerization Initiator (D): N-acyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, trade name PBG-327, O-acyl oxime compound, manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.

[0452] 5 parts

[0453] Solvent (E): Propylene glycol monomethyl ether acetate

[0454] 645 parts

[0455] Leveling agent (F): Polyether-modified silicone oil, trade name Toray Silicone SH8400, manufactured by Dow Toray Co., Ltd.

[0456] 0.1 part

[0457] <Film formation>

[0458] After applying the colored resin composition 1 onto a glass substrate (EAGLE 2000, manufactured by CORNING Inc.) with a size of 5 cm square by spin coating method, it was pre-baked at 100 °C for 2 minutes to obtain a film. Thereafter, the pre-baked film was post-baked at 230 °C for 5 minutes.

[0459] (Reliability evaluation)

[0460] Using a colorimeter (OSP-SP-200, manufactured by OLYMPUS Corporation), in the wavelength range of 380 nm to 780 nm, the film after post-baking was spectrophotometrically measured at 5 nm intervals, and the spectra before and after the solvent resistance test, heat resistance test, and light resistance test were respectively obtained.

[0461] (1) Solvent resistance test

[0462] The obtained film was immersed in propylene glycol monomethyl ether (PGME) or 2-butanone (MEK) at room temperature for 5 minutes, and the absorbance retention rate of the film before and after immersion was measured. Here, the absorbance retention rate is a value calculated by the following formula. The higher the absorbance retention rate, the better the solvent resistance. In addition, if the solvent resistance of the film is good, it can be said that the solvent resistance of the optical filter made of the same colored resin composition is also excellent.

[0463] Absorbance retention rate (%) = (Absorbance of the film after immersion at the maximum absorption wavelength) / (Absorbance of the film before immersion at the maximum absorption wavelength) × 100

[0464] In Example 1A, the absorbance retention rate when immersed in MEK was 100%, which was a value higher than the absorbance retention rate (85%) of Comparative Example 1A described later. In addition, in Example 1A, the absorbance retention rate when immersed in PGME was also 100%, which was a value higher than the absorbance retention rate (97%) of Comparative Example 1A described later.

[0465] (2) Heat resistance test

[0466] In an oven, in an atmospheric atmosphere, the obtained coating film was heated at 260 °C for 10 minutes, and the absorbance retention rate of the coating film before and after heating was measured. Here, the absorbance retention rate is a value calculated by the following formula. The higher the absorbance retention rate, the more excellent the heat resistance. In addition, if the heat resistance of the coating film is good, it can be said that the heat resistance of the optical filter made of the same colored resin composition is also excellent.

[0467] Absorbance retention rate (%) = (Absorbance of the coating film after heating at the maximum absorption wavelength) / (Absorbance of the coating film before heating at the maximum absorption wavelength) × 100

[0468] In Example 1A, the above absorbance retention rate was 84%, which is a value higher than the absorbance retention rate (77%) of Comparative Example 1A described later.

[0469] (3) Light resistance test

[0470] An ultraviolet cut-off filter (COLORED OPTICAL GLASS L38, manufactured by HOYA Corporation, a filter that cuts off light of 380 nm or less) was placed on the obtained coating film, and xenon lamp light was irradiated for 68 hours using a light resistance testing machine (SUNTEST CPS+, manufactured by Toyo Seiki Seisaku-sho, Ltd.), and the absorbance retention rate of the coating film before and after irradiation was measured. Here, the absorbance retention rate is a value calculated by the following formula. The higher the absorbance retention rate, the more excellent the light resistance. In addition, if the light resistance of the coating film is good, it can be said that the light resistance of the optical filter made of the same colored resin composition is also excellent.

[0471] Absorbance retention rate (%) = (Absorbance of the coating film after irradiation at the maximum absorption wavelength) / (Absorbance of the coating film before irradiation at the maximum absorption wavelength) × 100

[0472] In Example 1A, the above absorbance retention rate was 84%, which is a value higher than the absorbance retention rate (75%) of Comparative Example 1A described later.

[0473] (Spectral evaluation)

[0474] Using an ultraviolet-visible-near-infrared absorption spectrophotometer (JASCO: V-770), the coating film after post-baking was measured spectroscopically at 5 nm intervals in the wavelength range of 300 nm to 900 nm. In the obtained spectral data, the absorbance at the maximum absorption wavelength λ max was normalized to 2.0 (Abs(λ max )). In addition, in the wavelength range of 750 to 900 nm, the absorption wavelength λ 0.2 at which the absorbance becomes 0.20 (Abs(λ 0.2 )) was obtained, and the slope between the two points was calculated based on the following formula.

[0475] Slope ( / nm) = |(Abs(λ max ) - Abs(λ 0.2 )) / (λ max - λ 0.2 )|

[0476] The larger this value is, the easier it is to improve the light absorption in the visible region (especially the visible region on the long-wavelength side), and the higher the sensitivity as a sensor. Therefore, it is preferably a characteristic of an optical filter having near-infrared transmittance. The above slope in Example 1A is 0.028 / nm, which is larger than the slope (0.022 / nm) of Comparative Example 1A described later.

[0477] (Example 2A)

[0478] The dispersion liquid (A-1) was changed to the dispersion liquid (A-2), and except for this, a coating film was formed in the same manner as in Example 1A, and each physical property was evaluated.

[0479] In Example 2A, the absorbance retention rate when immersed in MEK measured by the same method as the above (1) solvent resistance test was 93%, which is a value higher than the absorbance retention rate (85%) of Comparative Example 1A described later.

[0480] In addition, in Example 2A, the absorbance retention rate measured by the same method as the above (2) heat resistance test was 93%, which is a value higher than the absorbance retention rate (77%) of Comparative Example 1A described later.

[0481] Furthermore, in Example 2A, the absorbance retention rate measured by the same method as the above (3) light resistance test was 100%, which is a value higher than the absorbance retention rate (75%) of Comparative Example 1A described later.

[0482] (Example 3A)

[0483] The dispersion liquid (A-1) was changed to the dispersion liquid (A-3), and except for this, a coating film was formed in the same manner as in Example 1A, and each physical property was evaluated.

[0484] In Example 3A, the absorbance retention rate when immersed in MEK measured by the same method as the above (1) solvent resistance test was 100%, which is a value higher than the absorbance retention rate (85%) of Comparative Example 1A described later. Also, the absorbance retention rate when immersed in PGME was 100%, which is a value higher than the absorbance retention rate (97%) of Comparative Example 1A described later.

[0485] In addition, in Example 3A, the absorbance retention rate measured by the same method as the above (2) heat resistance test was 92%, which is a value higher than the absorbance retention rate (77%) of Comparative Example 1A described later.

[0486] In addition, in Example 3A, the absorbance retention rate measured by the same method as the above-mentioned (3) light resistance test was 96%, which was a higher value than the absorbance retention rate (75%) of Comparative Example 1A described later.

[0487] (Comparative Example 1A)

[0488] The dispersion liquid (A-1) was changed to the dispersion liquid (X-1), and except for this, a coating film was formed by the same method as in Example 1A, and each physical property was evaluated.

[0489] In Comparative Example 1A, the absorbance retention rate when immersed in MEK measured by the same method as the above-mentioned (1) solvent resistance test was 85%. In addition, the absorbance retention rate when immersed in PGME was 97%.

[0490] In addition, in Comparative Example 1A, the absorbance retention rate measured by the same method as the above-mentioned (2) heat resistance test was 77%.

[0491] In addition, in Comparative Example 1A, the absorbance retention rate measured by the same method as the above-mentioned (3) light resistance test was 75%.

[0492] In addition, in Comparative Example 1A, the value of the slope obtained by the above spectral evaluation was 0.022 / nm.

Claims

1. A compound represented by formula (I), In formula (I), R 1 represents an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have substituents, R 2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, or a single bond connecting Z 2 to R 1 and the single bond of R Z 1 and Z 2 each independently represents a single bond or an oxygen atom, X 1 ~X 4 each independently represents -R 3 , -OR 3 , -SR 3 , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent, R 3 represents a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, n1 to n4 each independently represent an integer of 0 to 6.

2. A colored resin composition comprising the compound according to claim 1 and a resin.

3. The colored resin composition according to claim 2, wherein, it further contains at least one of a polymerizable compound and a polymerization initiator.

4. An optical filter formed from the colored resin composition according to claim 3.

5. A solid-state imaging device comprising the optical filter according to claim 4.

6. A display device comprising the optical filter according to claim 4.

Images