TW202413540A - Compound, colored resin composition, optical filter, solid state imaging element and display device - Google Patents

Abstract

The purpose of the present invention is to provide a compound and a colored resin composition which make it possible to produce an optical filter having improved solvent resistance (and preferably, improved solvent resistance, heat resistance, and light resistance). More preferably, the purpose of the present invention is to provide a compound and a colored resin composition which make it possible to produce an optical filter which, in the wavelength range of 750-900 nm, has increased steepness of inclination from [lambda]max to the long wavelength side in the absorption spectrum thereof. A compound according to the present invention is characterized by being represented by formula (I). [In formula (I), R1 represents a C2-20 unsaturated aliphatic hydrocarbon group that may have a substituent, and R2 represents a hydrogen atom, a C1-20 hydrocarbon group that may have a substituent, or a single bond that joins Z2 and R1. Z1 and Z2 independently represent a single bond or an oxygen atom.].

Description

Compound

The present invention relates to a compound, a coloring resin composition containing the compound, an optical filter formed by the coloring resin composition, and a solid-state imaging element and a display device containing the optical filter.

Optical filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays, or solid-state imaging devices such as charge coupled devices (CCD) and complementary metal oxide semiconductor (CMOS) sensors are made from a coloring resin composition. As a coloring agent used in such a coloring resin composition, a compound represented by formula (x1) is known (Patent Document 1).

[Prior art literature] [Patent literature]

[Patent Document 1] Japanese Patent Publication No. 2022-72558

[Problem to be solved by the invention] 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 formula (x1) is used, the solvent resistance of the obtained optical filter is not sufficient. Therefore, the problem of the present invention is to provide a compound and a coloring resin composition that can be used to prepare an optical filter with improved solvent resistance. [Means for solving the problem]

The gist of the present invention is as follows. [1] A compound represented by formula (I). [In formula (I), ^R1 represents an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, ^R2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a single bond linking ^Z2 to ^R1 ; ^Z1 and ^Z2 each independently represent a single bond or an oxygen atom; ^X1 to ^X4 each independently represent ^-R3 , ^-OR3 , ^-SR3 , a halogen atom, a nitro group, or an aminosulfonyl group which may have a substituent; ^R3 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent; n1 to n4 each independently represent an integer of 0 to 6] [2] A coloring resin composition comprising the compound described in [1] and a resin. [3] The coloring resin composition as described in [2], further comprising at least one of a polymerizable compound and a polymerization initiator. [4] An optical filter formed by the coloring resin composition as described in [2] or [3]. [5] A solid-state imaging element comprising the optical filter as described in [4]. [6] A display device comprising the optical filter as described in [4]. [Effects of the invention]

The present invention provides a compound and a coloring resin composition for producing an optical filter having improved solvent resistance (preferably solvent resistance, heat resistance and light resistance). In addition, according to the present invention, the drop of absorbance on the long-wavelength side from λ _max in the absorption spectrum becomes steeper (the steepness of the slope on the long-wavelength side from λ _max is high) in the wavelength range of 750 nm to 900 nm, and the sensitivity of the optical filter used in a solid-state imaging element that senses near-infrared rays can be improved.

＜＜Compound＞＞ The present invention is described in more detail below by listing partial structures of compounds represented by formula (I) (hereinafter, sometimes referred to as compound (I)). According to the compound (I) of the present invention, in an optical filter formed from a coloring resin composition containing the compound (I), solvent resistance (preferably solvent resistance, heat resistance, and light resistance) can be improved. In addition, it is preferred that the optical filter formed from a coloring resin composition containing the compound (I) has an improved steepness of the slope on the long-wavelength side from λ _max in the absorption spectrum in the wavelength range of 750 nm to 900 nm.

[In formula (I), ^R1 represents an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, ^R2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a single bond linking ^Z2 to ^R1 ; ^Z1 and ^Z2 each independently represent a single bond or an oxygen atom; ^X1 to ^X4 each independently represent ^-R3 , ^-OR3 , ^-SR3 , a halogen atom, a nitro group, or an aminosulfonyl group which may have a substituent; ^R3 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent; n1 to n4 each independently represent an integer from 0 to 6]

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

The unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R ¹ may be in the form of a chain or a ring (alicyclic hydrocarbon group).

The chain unsaturated aliphatic hydrocarbon group represented by ^R1 may be a straight chain or a branched chain. Specifically, the following may be mentioned: vinyl, propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1-methyl-1-butenyl, 3-methyl-2-butenyl, 1,3-butadienyl, 3-methyl-1,2-butadienyl, 1-(2-propenyl)vinyl, 1-(1-methylvinyl)vinyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, pentenyl (e.g., 1-pentenyl, 2-pentenyl), alkenyl groups such as 1-decenyl, 2-decenyl, 3-pentenyl, 4-pentenyl, 1-(1,1-dimethylethyl)vinyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), decenyl (e.g., 1-decenyl, 9-decenyl), undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, and eicosenyl; 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), The unsaturated aliphatic chain alkyl group (i.e., alkenyl, alkynyl) represented by R1 preferably has 2 to 15 carbon atoms, more preferably 2 to 10 carbon atoms, and ^still more preferably 2 to 8 carbon atoms.

Examples of the unsaturated alicyclic alkyl group represented by ^R1 include: cyclohexenyl (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl, cyclooctenyl and other cycloalkenyl groups; norbornene and other unsaturated polycyclic alkyl groups, etc. The unsaturated alicyclic alkyl group represented by ^R1 preferably has 3 to 10 carbon atoms.

The substituent that the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by ^R1 may have. Examples of the substituent of the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by ^R1 include an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have a substituent, a heterocyclic group that may have a substituent, a halogen atom, a ^nitro group, a cyano group, ^-ORa1 , _-CO2Ra1 , ^-SRa1 , _-SO2Ra1 , ^{-SO3Ra1 ,} _-SO2NRa1Ra2 ^, and ^-NRa1Ra2 . Here, ^{Ra1 and Ra2 each} independently represent a hydrogen atom or a hydrocarbon group ^having 1 to ₂₀ carbon atoms. The alkyl group having 1 to 20 carbon atoms represented by ^Ra1 and ^Ra2 is the same as the alkyl group having 1 to 20 carbon atoms represented by ^R2 and ^R3 described later.

Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms used as a substituent for the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by ^R1 include phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-t-butylphenyl, m-t-butylphenyl, p-t-butylphenyl, 3,5-di(t-butyl)phenyl, 3,5-di(t-butyl)-4-methylphenyl, and 4-n-butylphenyl. , 4-pentylphenyl, 2,6-bis(1-methylethyl)phenyl, 2,4,6-tri(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, phenanthrenyl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, peryl, chrysyl, pyrenyl and other aromatic hydrocarbon groups. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 10, more preferably 6 to 8. The aromatic hydrocarbon group may have a substituent. _Examples ^{of the} substituent include a halogen atom, ^a nitro group, a cyano group, ^-ORa1 , ^-CO2Ra1 , _-SRa1 , ^-SO2Ra1 , _-SO3Ra1 , _-SO2NRa1Ra2 and ^-NRa1Ra2 (wherein ^{Ra1 and Ra2} are ^the same as described above).

The heterocyclic ring constituting the heterocyclic group used as a substituent of the unsaturated aliphatic alkyl group having 2 to 20 carbon atoms represented by ^R1 may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a hetero atom as a constituent element of the ring. Examples of the heterocyclic ring containing only a nitrogen atom include a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of the heterocyclic ring containing only a nitrogen atom include a monocyclic saturated heterocyclic ring such as aziridine, azetidine, pyrrolidine, piperidine, and piperazine; a 5-membered unsaturated heterocyclic ring such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, and 1,2,4-triazole; and a 5-membered unsaturated heterocyclic ring such as pyridine, pyrazine, pyrimidine, pyrazine, 1,3,5-triazole. unsaturated six-membered ring heterocycles such as indazole, indoline, isoindoline, isoindoline-1,3-dione, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine and the like; condensed tricyclic heterocycles such as carbazole, acridine, phenazine and the like. Examples of heterocyclic rings containing only oxygen atoms as heteroatoms include: monocyclic saturated heterocyclic rings such as cyclohexane, cyclohexane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, and 1,4-dioxane; bicyclic saturated heterocyclic rings such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; α-acetone, β-propiolactone, γ-butyrolactone, δ- -valerolactone and other lactone-based heterocyclic rings; furan and other 5-membered unsaturated heterocyclic rings; 2H-pyran, 4H-pyran and other 6-membered unsaturated heterocyclic rings; 1-benzofuran, benzopyran, benzodioxole, chromane, isochromane and other condensed bicyclic heterocyclic rings; oxanthracene, dibenzofuran and other condensed tricyclic heterocyclic rings, etc. Examples of heterocyclic rings containing only sulfur atoms as heteroatoms include: 5-membered saturated heterocyclic rings such as dithiocyclopentane; 6-membered saturated heterocyclic rings such as thiane and 1,3-dithiane; 5-membered unsaturated heterocyclic rings such as thiophene; 6-membered unsaturated heterocyclic rings such as 4H-thiopyran; condensed bicyclic heterocyclic rings such as benzothiopyran and benzothiophene; and condensed tricyclic heterocyclic rings such as thianthrene and dibenzothiophene. Examples of heterocyclic rings containing nitrogen and oxygen atoms as heteroatoms include: monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, and 2-piperidone; monocyclic unsaturated heterocyclic rings such as oxazole and isoxazole; condensed bicyclic heterocyclic rings such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzimidazolin; condensed tricyclic heterocyclic rings such as phenoxazine, etc. Examples of heterocyclic rings containing nitrogen and sulfur atoms as heteroatoms include: monocyclic heterocyclic rings such as thiazole; condensed bicyclic heterocyclic rings such as benzothiazole; condensed tricyclic heterocyclic rings such as phenoxathiazine, etc. Furthermore, the so-called heterocyclic group refers to a group in which any hydrogen atom contained in the heterocyclic ring is separated to form a bonding site. The carbon number of the heterocyclic group is preferably 2 to 30, more preferably 3 to 22, and even more preferably 3 to 20. The heterocyclic group may have a substituent, and 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 NR ^a1 R ^a2 and -NR ^a1 R ^a2 (wherein R ^a1 and R ^a2 are the same as described above).

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

The alkyl group having 1 to 20 carbon atoms represented by ^R2 and ^R3 may be any of an aliphatic alkyl group, an aromatic alkyl group, and a combination thereof. The aliphatic alkyl group may be saturated or unsaturated and may be in the form of a chain or a ring (alicyclic alkyl group).

As the saturated or unsaturated chain hydrocarbon group, there can be listed: methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecayl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and n-eicosyl linear alkyl groups; 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, Branched chain alkyl groups such as 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; vinyl, propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1-methyl-1-butenyl, 3-methyl-2-butenyl, 1,3-butadienyl, 3-methyl-1,2-butadienyl, 1-(2-propenyl)vinyl, 1-(1-methylvinyl)vinyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, pentenyl (e.g., 1-pentenyl, 2-pentenyl 1-(1,1-dimethylethyl)vinyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), decenyl (e.g., 1-decenyl, 9-decenyl), undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosene and other alkenyl groups; 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- alkynyl groups such as 1-octynyl, 2-octynyl, 7-octynyl, nonynyl (e.g., 2-nonynyl, 8-nonynyl), decynyl (e.g., 2-decynyl, 9-decynyl), undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecenyl, octadecynyl, nonadecenyl, and eicosynyl.

The carbon number of the saturated chain alkyl group (i.e., straight chain alkyl group, branched chain alkyl group) is preferably 1 to 10, more preferably 1 to 7, and even more preferably 1 to 5. The carbon number of the unsaturated chain alkyl group (i.e., alkenyl group, alkynyl group) is preferably 2 to 15, more preferably 2 to 10, and even more preferably 2 to 8.

As the saturated or unsaturated alicyclic alkyl group, there can be mentioned 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; 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; Saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl, etc.

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

Examples of the aromatic hydrocarbon group include the groups explained as the aromatic hydrocarbon group having 6 to 20 carbon atoms used as a substituent for the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R ¹ .

The carbon number of the aromatic hydrocarbon group is preferably 6-15, more preferably 6-10, further preferably 6-8.

The alkyl group represented by ^R2 and ^R3 may be a group in which the alkyl groups listed above are combined, as long as the total number of carbon atoms is 20 or less. Examples of such a group include a group in which an aromatic alkyl group is combined with at least one of a chain alkyl group, an alicyclic alkyl group and an aromatic alkyl group; a group in which a chain alkyl group is combined with an alicyclic alkyl group, and the like.

Examples of the group formed by combining an aromatic hydrocarbon group with at least one of a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group include: 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; Arylalkenyl groups such as 1-phenylvinyl, 2-phenylvinyl (phenyl ethenyl) (phenyl vinyl), 2,2-diphenylvinyl, and 2-phenyl-2-(1-naphthyl)vinyl; Aryl alkynyl such as phenylethynyl and 3-phenyl-2-propynyl; Phenyl groups bonded to more than one phenyl group such as biphenyl and terphenyl; Cyclohexylmethylphenyl, benzylphenyl, (dimethyl(phenyl)methyl)phenyl, etc. The carbon number of these groups is preferably 7 to 18, more preferably 7 to 15.

Examples of the group formed by combining a chain alkyl group and an alicyclic alkyl group include an alkyl group bonded to one or more alicyclic alkyl groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl)methyl, cyclohexylethyl, and adamantylmethyl. The carbon number of these groups is preferably 4 to 15, more preferably 4 to 10.

The alkyl group having 1 to 20 carbon atoms represented by ^R2 and ^R3 may have a substituent. Examples of the substituent include ^a heterocyclic group which may have a substituent, a _halogen ^atom , a nitro group, a cyano group, ^-ORa1 , _-CO2Ra1 , ^-SRa1 , ^-SO2Ra1 , _-SO3Ra1 , _-SO2NRa1Ra2 and ^{-NRa1Ra2 (} wherein ^{Ra1 and Ra2 are} the same as those described above).

Examples of the "heterocyclic group which may have a substituent" used as a substituent for the alkyl group having 1 to 20 carbon atoms represented by ^R2 and ^R3 include the same as the "heterocyclic group which may have a substituent" used as a substituent for the unsaturated aliphatic alkyl group having 2 to 20 carbon atoms represented by ^R1 .

Examples of the halogen atom as a substituent of the alkyl group having 1 to 20 carbon atoms represented by R ² and R ³ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

When ^R2 is a single bond linking ^Z2 and ^R1 , a part or all of ^R1 forms a ring together with * ^-Z2 -P(=O) ^-Z1- * (* represents a bond). That is, when ^R2 is a single bond linking ^Z2 and ^R1 , 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 ^R1 and ^Z2 is equivalent to the single bond represented by ^R2 .

In the ring formed by a part or all of R ¹ together with *-Z ² -P(=O)-Z ¹ -* (* represents a bond), unsaturated bonds may be formed between carbon atoms constituting the ring, between carbon atoms constituting the ring and carbon atoms other than the ring, or between carbon atoms other than the ring.

Examples of the group bonded to the bonding bond in the above-mentioned *-Z ² -P(=O)-Z ¹ -* (* represents a bonding bond) include groups represented by formulas (cy1) to (cy3).

[In the formula, R ¹⁵ to R ¹⁶ independently represent a hydrogen atom or a carbon number of 1 to 8 which may have a substituent, R ¹⁷ represents an unsaturated aliphatic carbon number of 2 to 10 which may have a substituent, and R ¹⁸ represents a hydrogen atom or a hydroxyl group; * represents a bonding bond]

Examples of the alkyl group having 1 to 8 carbon atoms which may be substituted and represented by ^R15 and ^R16 include groups having 1 to 8 carbon atoms in the groups explained as the alkyl group having 1 to 20 carbon atoms which may be substituted and represented by ^R2 and ^R3 . Examples of the unsaturated aliphatic alkyl group having 2 to 10 carbon atoms which may be substituted and represented by ^R17 include groups having 2 to 10 carbon atoms in the groups explained as the unsaturated aliphatic alkyl group having 2 to 20 carbon atoms which may be substituted and represented by ^R1 .

R ¹⁵ and R ¹⁶ are preferably independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which may have a substituent.

R ¹⁷ is preferably an alkenyl group or alkynyl group having 2 to 10 carbon atoms which may have an aromatic hydrocarbon group having 6 to 10 carbon atoms.

Examples of the halogen atom represented by X ¹ to X ⁴ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

The sulfonamide group represented by X ¹ to X ⁴ is represented by *-SO ₂ -NH ₂ (* indicates a bond). The sulfonamide group represented by X ¹ to X ⁴ may have a substituent. Examples of the substituent of the sulfonamide group represented by X ¹ to X ⁴ are the same as the substituent of the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R ¹ , and specifically, there can be mentioned an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, 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 (wherein R ^a1 and R ^a2 are the same as described above).

R ³ in -R ³ , -OR ³ and -SR ³ represented by X ¹ to X ⁴ 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, further preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, further preferably a linear or branched chain alkyl group having 1 to 5 carbon atoms, particularly preferably a methyl group, ethyl group, n-propyl group, isopropyl group or t-butyl group.

The ^Ra1 and ^Ra2 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, and 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.

In formula (I), R ¹ is preferably an unsaturated aliphatic chain hydrocarbon group having 2 to 20 carbon atoms (i.e., alkenyl group, alkynyl group) which may have a substituent, and more preferably an unsaturated aliphatic chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent. In particular, from the viewpoint of further improving the steepness of the slope from λ _max in the absorption spectrum of the obtained optical filter, R ¹ is preferably an alkynyl group having 2 to 20 carbon atoms which may have a substituent, and more preferably an alkynyl group having 2 to 10 carbon atoms which may have a substituent.

When the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R ¹ has a substituent, the substituent is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, and particularly preferably a phenyl group. That is, R ¹ is particularly preferably an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 20 carbon atoms which 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 NR ^a1 R ^a2 and -NR ^a1 R ^a2 (wherein R ^a1 and R ^a2 are the same as described above).

In formula (I), R ² is preferably a hydrogen atom, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, an arylalkynyl group having 8 to 20 carbon atoms which may have a substituent, or a single bond connecting Z ² and R ^1. More preferably, it is a hydrogen atom, an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, an unsaturated aliphatic chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 15 carbon atoms which may have a substituent, an arylalkynyl group having 8 to 15 carbon atoms which may have a substituent, or a single bond connecting Z ² and R ¹ . In particular, from the viewpoint of further improving the steepness of the slope from λ _max in the absorption spectrum of the obtained optical filter, R ² is preferably an alkynyl group having 2 to 20 carbon atoms which may have a substituent, and more preferably an alkynyl group having 2 to 10 carbon atoms which may have a substituent.

In particular, when ^Z1 and ^Z2 are a single bond and when ^Z1 is an oxygen atom and ^Z2 is a single bond, it is preferred that ^R1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, and ^R2 is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent; it is more preferred that ^R1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent, and ^R2 is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent.

In addition, when ^Z1 and ^Z2 are oxygen atoms, it is preferred that ^R1 and ^R2 are unsaturated aliphatic chain hydrocarbon groups having 2 to 20 carbon atoms which may have a substituent, or ^R1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, and ^R2 is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or a single bond connecting ^Z2 to ^R1 ; it is more preferred that ^R1 and ^R2 are unsaturated aliphatic chain hydrocarbon groups having 2 to 10 carbon atoms which may have a substituent, or ^R1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent, and ^R2 is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, or a single bond connecting ^Z2 to ^R1 .

In addition, when ^Z1 is a single bond and ^Z2 is an oxygen atom, it is preferred that ^R1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, and ^R2 is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or a hydrogen atom; it is more preferred that ^R1 is an unsaturated aliphatic chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent, and ^R2 is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent or a hydrogen atom.

X ¹ to X ⁴ are each independently preferably -R ³ , -OR ³ or a halogen atom (particularly preferably 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 most preferably a halogen atom.

n1 to n4 are each independently preferably 0, 1, 2 or 6. 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, and more preferably 0 or 1. 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, and more preferably 1, 2 or 6, and further preferably 1 or 2. 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, and more preferably 0.

Examples of the naphthyl ring to which X ¹ to X ⁴ in formula (I) may be bonded include structures represented by formula (t2-1) to formula (t2-10), wherein m represents an integer of 1 to 5, and * represents a bond with the pyrrole ring in formula (I).

The four naphthyl rings to which X ¹ to X ⁴ in compound (I) can be bonded may be the same or different, but are preferably the same.

Specifically, the compound (I) includes compounds represented by the following formulae (I-1) to (I-10), wherein R ¹ , R ² , Z ¹ and Z ² are any of No. 1 to No. 132 listed in Tables 1 and 2. In the formulae, n represents an integer of 1 to 5.

[Table 1] No. Z ¹ Z ² R ¹ R ² No. Z ¹ Z ² R ¹ R ² 1 Oxygen atom Oxygen atom i-1 i-1 45 Oxygen atom Single button i-1 ii-1 2 Oxygen atom Oxygen atom i-2 i-2 46 Oxygen atom Single button i-2 ii-1 3 Oxygen atom Oxygen atom i-3 i-3 47 Oxygen atom Single button i-3 ii-1 4 Oxygen atom Oxygen atom i-4 i-4 48 Oxygen atom Single button i-4 ii-1 5 Oxygen atom Oxygen atom i-5 i-5 49 Oxygen atom Single button i-5 ii-1 6 Oxygen atom Oxygen atom i-6 i-6 50 Oxygen atom Single button i-6 ii-1 7 Oxygen atom Oxygen atom i-7 i-7 51 Oxygen atom Single button i-7 ii-1 8 Oxygen atom Oxygen atom i-8 i-8 52 Oxygen atom Single button i-8 ii-1 9 Oxygen atom Oxygen atom i-9 i-9 53 Oxygen atom Single button i-9 ii-1 10 Oxygen atom Oxygen atom i-10 i-10 54 Oxygen atom Single button i-10 ii-1 11 Oxygen atom Oxygen atom i-11 i-11 55 Oxygen atom Single button i-11 ii-1 12 Oxygen atom Oxygen atom i-12 i-12 56 Oxygen atom Single button i-12 ii-1 13 Oxygen atom Oxygen atom i-13 i-13 57 Oxygen atom Single button i-13 ii-1 14 Oxygen atom Oxygen atom i-14 i-14 58 Oxygen atom Single button i-14 ii-1 15 Oxygen atom Oxygen atom i-15 i-15 59 Oxygen atom Single button i-15 ii-1 16 Oxygen atom Oxygen atom i-16 i-16 60 Oxygen atom Single button i-16 ii-1 17 Oxygen atom Oxygen atom i-17 i-17 61 Oxygen atom Single button i-17 ii-1 18 Oxygen atom Oxygen atom i-18 i-18 62 Oxygen atom Single button i-18 ii-1 19 Oxygen atom Oxygen atom i-19 i-19 63 Oxygen atom Single button i-19 ii-1 20 Oxygen atom Oxygen atom I-20 I-20 64 Oxygen atom Single button I-20 ii-1 twenty one Oxygen atom Oxygen atom I-21 I-21 65 Oxygen atom Single button I-21 ii-1 twenty two Oxygen atom Oxygen atom i-22 i-22 66 Oxygen atom Single button i-22 ii-1 twenty three Oxygen atom Oxygen atom i-1 ii-1 67 Single button Single button i-1 ii-1 twenty four Oxygen atom Oxygen atom i-2 ii-1 68 Single button Single button i-2 ii-1 25 Oxygen atom Oxygen atom i-3 ii-1 69 Single button Single button i-3 ii-1 26 Oxygen atom Oxygen atom i-4 ii-1 70 Single button Single button i-4 ii-1 27 Oxygen atom Oxygen atom i-5 ii-1 71 Single button Single button i-5 ii-1 28 Oxygen atom Oxygen atom i-6 ii-1 72 Single button Single button i-6 ii-1 29 Oxygen atom Oxygen atom i-7 ii-1 73 Single button Single button i-7 ii-1 30 Oxygen atom Oxygen atom i-8 ii-1 74 Single button Single button i-8 ii-1 31 Oxygen atom Oxygen atom i-9 ii-1 75 Single button Single button i-9 ii-1 32 Oxygen atom Oxygen atom i-10 ii-1 76 Single button Single button i-10 ii-1 33 Oxygen atom Oxygen atom i-11 ii-1 77 Single button Single button i-11 ii-1 34 Oxygen atom Oxygen atom i-12 ii-1 78 Single button Single button i-12 ii-1 35 Oxygen atom Oxygen atom i-13 ii-1 79 Single button Single button i-13 ii-1 36 Oxygen atom Oxygen atom i-14 ii-1 80 Single button Single button i-14 ii-1 37 Oxygen atom Oxygen atom i-15 ii-1 81 Single button Single button i-15 ii-1 38 Oxygen atom Oxygen atom i-16 ii-1 82 Single button Single button i-16 ii-1 39 Oxygen atom Oxygen atom i-17 ii-1 83 Single button Single button i-17 ii-1 40 Oxygen atom Oxygen atom i-18 ii-1 84 Single button Single button i-18 ii-1 41 Oxygen atom Oxygen atom i-19 ii-1 85 Single button Single button i-19 ii-1 42 Oxygen atom Oxygen atom I-20 ii-1 86 Single button Single button I-20 ii-1 43 Oxygen atom Oxygen atom I-21 ii-1 87 Single button Single button I-21 ii-1 44 Oxygen atom Oxygen atom i-22 ii-1 88 Single button Single button i-22 ii-1

[Table 2] No. Z ¹ Z ² R ¹ R ² No. Z ¹ Z ² R ¹ R ² 89 Single button Oxygen atom i-1 ii-1 111 Single button Oxygen atom i-1 ii-2 90 Single button Oxygen atom i-2 ii-1 112 Single button Oxygen atom i-2 ii-2 91 Single button Oxygen atom i-3 ii-1 113 Single button Oxygen atom i-3 ii-2 92 Single button Oxygen atom i-4 ii-1 114 Single button Oxygen atom i-4 ii-2 93 Single button Oxygen atom i-5 ii-1 115 Single button Oxygen atom i-5 ii-2 94 Single button Oxygen atom i-6 ii-1 116 Single button Oxygen atom i-6 ii-2 95 Single button Oxygen atom i-7 ii-1 117 Single button Oxygen atom i-7 ii-2 96 Single button Oxygen atom i-8 ii-1 118 Single button Oxygen atom i-8 ii-2 97 Single button Oxygen atom i-9 ii-1 119 Single button Oxygen atom i-9 ii-2 98 Single button Oxygen atom i-10 ii-1 120 Single button Oxygen atom i-10 ii-2 99 Single button Oxygen atom i-11 ii-1 121 Single button Oxygen atom i-11 ii-2 100 Single button Oxygen atom i-12 ii-1 122 Single button Oxygen atom i-12 ii-2 101 Single button Oxygen atom i-13 ii-1 123 Single button Oxygen atom i-13 ii-2 102 Single button Oxygen atom i-14 ii-1 124 Single button Oxygen atom i-14 ii-2 103 Single button Oxygen atom i-15 ii-1 125 Single button Oxygen atom i-15 ii-2 104 Single button Oxygen atom i-16 ii-1 126 Single button Oxygen atom i-16 ii-2 105 Single button Oxygen atom i-17 ii-1 127 Single button Oxygen atom i-17 ii-2 106 Single button Oxygen atom i-18 ii-1 128 Single button Oxygen atom i-18 ii-2 107 Single button Oxygen atom i-19 ii-1 129 Single button Oxygen atom i-19 ii-2 108 Single button Oxygen atom I-20 ii-1 130 Single button Oxygen atom I-20 ii-2 109 Single button Oxygen atom I-21 ii-1 131 Single button Oxygen atom I-21 ii-2 110 Single button Oxygen atom i-22 ii-1 132 Single button Oxygen atom i-22 ii-2

In Tables 1 and 2, i-1 to i-22 represent groups represented by the following formulae (i-1) to (i-22), and ii-1 to ii-2 represent groups represented by the following formulae (ii-1) to (ii-2), respectively. In the following formulae, * represents a bond.

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

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

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

[In the formula, R ¹ to R ² , Z ¹ to Z ² , X ¹ to X ⁴ , n1 to n4 and X have the same meanings as described above]

<<Coloring resin composition>> The present invention includes a coloring resin composition containing the compound (I) and a resin (hereinafter, sometimes referred to as resin (B)). The coloring resin composition of the present invention preferably includes the compound (I) as a coloring agent (hereinafter, sometimes referred to as coloring agent (A)). The coloring resin composition of the present invention preferably further includes 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)). The coloring resin composition of the present invention preferably further includes a solvent (hereinafter, sometimes referred to as solvent (E)). The coloring resin composition of the present invention may also include a leveling agent (hereinafter, sometimes referred to as leveling agent (F)). In this specification, compounds exemplified as components may be used alone or in combination unless otherwise specified.

<Coloring agent (A)> The content of compound (I) in the total amount of solid components of the coloring resin composition is preferably 0.5 mass% to 70 mass%, more preferably 1 mass% to 55 mass%, further preferably 2 mass% to 50 mass%, and particularly preferably 8 mass% to 40 mass%. In addition, in this specification, the so-called "total amount of solid components" refers to the total amount of components after removing the solvent from the coloring resin composition of the present invention. The total amount of solid components and the content of each component relative to the total amount of solid components can be measured by known analytical methods such as liquid chromatography and gas chromatography.

In addition, the content of compound (I) in the total amount of colorant (A) is preferably 20 mass% to 100 mass%, more preferably 30 mass% to 100 mass%, and further preferably 40 mass% to 100 mass%. If the solid content of the coloring resin composition or the content of compound (I) in the coloring agent (A) is within the above range, it is easier to obtain the desired spectral distribution, and it is easy to improve the reliability of heat resistance/light resistance/solvent resistance. In particular, when the optical filter formed by the coloring resin composition of the present invention is used as a near-infrared transmission filter in a solid-state imaging element that senses near-infrared rays, it is preferable to adjust the content of compound (I) in the coloring agent (A) to the above range. When the optical filter formed by the coloring 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 of the compound (I) in the total amount of the colorant (A) may be 1% to 80% by mass, 2% to 50% by mass, or 3% to 30% by mass. By adjusting the content of the compound (I) to the above range, the wavelength of the obtained color filter can be controlled.

The coloring agent (A) may further include a coloring agent different from the compound (I) (hereinafter, sometimes referred to as the coloring agent (A1)). The coloring agent (A1) may be any of a dye and a pigment.

Examples of dyes include compounds classified as having a hue other than pigments in the Color Index (published by The Society of Dyers and Colourists) or known dyes listed in Dyeing Notes (published by Dyeing Co., Ltd.).

Examples of dyes include azo dyes, cyanine dyes, triphenylmethane dyes, oxanthracene dyes, thiazole dyes, oxazine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Among these, organic solvent-soluble dyes are preferred.

As dyes, specifically, they include: C.I. Solvent Yellow 4 (hereinafter, C.I. Solvent Yellow is omitted, only the number is recorded; 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; C.I. Solvent Red 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; C.I. solvent orange (solvent orange) 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; C.I. solvent violet (solvent violet) 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. solvent blue (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; C.I. solvent green (solvent green) 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and other C.I. solvent dyes; C.I. acid yellow (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, 156 7, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; C.I. Acid Red (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; 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; C.I. Acid violet: 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; C.I. Acid blue: 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, 124 6, 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; C.I. acid green (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; C.I. direct yellow (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; C.I. direct red (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; C.I. direct orange (direct orange) 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; C.I. direct purple (direct violet) 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; C.I. direct blue (direct blue)1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 1 67, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; 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; C.I. disperse yellow 51, 54, 76; C.I. disperse violet 26, 27; C.I. disperse blue 1, 14, 56, 60 and other C.I. disperse dyes; C.I. basic red 1, 9, 10; C.I. basic blue 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 (basic violet) 2; C.I. basic green (basic green) 1 and other C.I. alkaline dyes; C.I. reactive yellow (reactive yellow) 2, 76, 116; C.I. reactive orange (reactive orange) 16; C.I. reactive red (reactive red) 36 and other C.I. reactive dyes; C.I. mordant yellow (mordant yellow yellow) 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C.I. mordant red (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; C.I. mordant orange (mordant orange) 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; 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; C.I. mordant blue (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; C.I. mordant green (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; C.I. vat green (vat green) 1 and other C.I. vat dyes, etc. These dyes can use one dye or multiple dyes for various colors, and can also combine dyes of various colors.

As pigments, for example, there are pigments classified as pigments in the Colour Index (published by The Society of Dyers and Colourists). Examples of pigments that are classified as pigments include: 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, etc.; C.I. pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.; C.I. pigment red 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc. C.I. pigment blue (pigment blue) 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments; C.I. pigment violet (pigment violet) 1, 19, 23, 32, 36, 38 and other purple pigments; C.I. pigment green (pigment green) 7, 36, 58, 59, 62, 63 and other green pigments; C.I. pigment brown (pigment Brown) 23, 25 and other brown pigments; C.I. pigment black 1, 7 and other black pigments. These pigments can use one pigment or multiple pigments for various colors, and can also combine pigments of various colors.

The pigment may be subjected to rosin treatment, surface treatment using a pigment derivative into which an acidic or alkaline group is introduced, grafting treatment on the pigment surface using a polymer compound, micronization treatment using a sulfuric acid micronization method, washing treatment using an organic solvent or water to remove impurities, and treatment to remove ionic impurities using an ion exchange method. The particle size of the pigment is preferably substantially uniform.

The content of the coloring agent (A) in the coloring resin composition is preferably 0.5 mass % to 80 mass %, more preferably 1 mass % to 70 mass %, further preferably 2 mass % to 55 mass %, and particularly preferably 8 mass % to 50 mass % relative to the total amount of the solid components. When the content of the coloring agent (A) is within the above range, it is easier to obtain the desired light distribution or color concentration.

<Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6]. Resin [K1]: A copolymer of at least one monomer (a) selected from the group consisting of 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)"); Resin [K2]: A copolymer of (a), (b), and a monomer (c) copolymerizable with (a) (wherein, different from (a) and (b)) (hereinafter, sometimes referred to as "(c)"); Resin [K3]: A copolymer of (a) and (c); Resin [K4]: A resin obtained by reacting a copolymer of (a) and (c) with (b); Resin [K5]: A resin obtained by reacting a copolymer of (b) and (c) with (a); Resin [K6]: A resin obtained by reacting a copolymer of (b) and (c) with (a), and then reacting the resulting mixture with a polycarboxylic acid and/or a carboxylic anhydride.

As (a), specifically, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid can be cited; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citric acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexene dicarboxylic acid can be cited; Bicyclic unsaturated compounds containing carboxyl groups, 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, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic anhydrides such as maleic anhydride, conic 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; Unsaturated mono[(meth)acryloxyalkyl]esters of polycarboxylic acids having a valence of more than two or more such as mono[2-(meth)acryloxyethyl]succinate and mono[2-(meth)acryloxyethyl]phthalate; Unsaturated acrylic esters containing a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl)acrylic acid, etc. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred in terms of copolymerization reactivity or solubility of the obtained resin in alkaline aqueous solution.

(b) refers to a polymerizable compound having, for example, a cyclic ether structure having 2 to 4 carbon atoms (e.g., at least one selected from the group consisting of cyclohexane ring, cyclohexane ring, and tetrahydrofuran ring) and an ethylenic unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group. In addition, in this specification, the so-called "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. Expressions such as "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

Examples of (b) include a monomer having an oxycyclopropyl group and an ethylenic unsaturated bond (b1) (hereinafter, sometimes referred to as "(b1)"), a monomer having an oxycyclobutyl group and an ethylenic unsaturated bond (b2) (hereinafter, sometimes referred to as "(b2)"), and a monomer having a tetrahydrofuranyl group and an ethylenic unsaturated bond (b3) (hereinafter, sometimes referred to as "(b3)"), etc.

Examples of (b1) include a monomer (b1-1) having a structure in which a linear or branched chain unsaturated aliphatic hydrocarbon is epoxidized (hereinafter, sometimes referred to as "(b1-1)") and a monomer (b1-2) having a structure in which alicyclic unsaturated hydrocarbon is epoxidized (hereinafter, sometimes referred to as "(b1-2)").

Examples of (b1-1) include: (meth) glycidyl acrylate, (meth) acrylate β-methyl glycidyl acrylate, (meth) acrylate β-ethyl glycidyl acrylate, glycidyl vinyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p-vinyl benzyl glycidyl ether, α-methyl-o-vinyl benzyl glycidyl ether, α-methyl-m-vinyl benzyl glycidyl ether, α-methyl-p-vinyl benzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)benzene Ethylene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tri(glycidyloxymethyl)styrene, 2,3,5-tri(glycidyloxymethyl)styrene, 2,3,6-tri(glycidyloxymethyl)styrene, 3,4,5-tri(glycidyloxymethyl)styrene, 2,4,6-tri(glycidyloxymethyl)styrene, and the like.

Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Co., Ltd.), 3,4-epoxyepoxyhexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Co., Ltd.), 3,4-epoxyepoxyhexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Co., Ltd.), 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate, a compound represented by formula (R1), and a compound represented by formula (R2).

[In formula (R1) and formula (R2), ^Rra and ^Rrb represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted by a hydroxyl group; ^Xra and ^Xrb represent a single bond, * ^-Rrc- , * ^-Rrc -O-, * ^-Rrc -S- or * ^-Rrc -NH-; ^Rrc represents an alkanediyl group having 1 to 6 carbon atoms; * represents a bond with O]

Examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc. Examples of the alkyl group in which a hydrogen atom is substituted by a hydroxyl group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc. Examples of ^Rra and ^Rrb include preferably a hydrogen atom, methyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, and more preferably a hydrogen atom and methyl.

Examples of the alkanediyl group include methylene, ethylidene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, etc. Examples of ^Xra and ^Xrb include preferably a single bond, methylene, ethylidene, * _-CH2 -O-, and * _-CH2CH2 -O-, and more preferably a single bond _and * _{-CH2CH2 -} O- (* represents a bond with O).

Examples of the compound represented by formula (R1) include compounds represented by any one of formula (R1-1) to formula (R1-15). Among them, preferred are compounds represented by formula (R1-1), formula (R1-3), formula (R1-5), formula (R1-7), formula (R1-9) or formula (R1-11) to formula (R1-15), and more preferred are compounds represented by formula (R1-1), formula (R1-7), formula (R1-9) or formula (R1-15).

Examples of the compound represented by formula (R2) include compounds represented by any one of formula (R2-1) to formula (R2-15). Among them, preferred are compounds represented by formula (R2-1), formula (R2-3), formula (R2-5), formula (R2-7), formula (R2-9) or formula (R2-11) to formula (R2-15), and more preferred are compounds represented by formula (R2-1), formula (R2-7), formula (R2-9) or formula (R2-15).

As (b2), a monomer having an oxycyclobutyl group and a (meth)acryloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloxymethyloxycyclobutane, 3-methyl-3-acryloxymethyloxycyclobutane, 3-ethyl-3-methacryloxymethyloxycyclobutane, 3-ethyl-3-acryloxymethyloxycyclobutane, 3-methyl-3-methacryloxyethyloxycyclobutane, 3-methyl-3-acryloxyethyloxycyclobutane, 3-ethyl-3-methacryloxyethyloxycyclobutane, and 3-ethyl-3-acryloxyethyloxycyclobutane.

As (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

As (b), (b1) is preferred in terms of further improving the reliability of the obtained optical filter in terms of heat resistance, chemical resistance, etc. Furthermore, (b1-2) is more preferred in terms of excellent storage stability of the colored resin composition.

Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate (usually referred to as "dicyclopentane (meth)acrylate" in the art; sometimes referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 ^2,6 ] (Meth)acrylates such as decen-8-yl ester (usually referred to as "dicyclopentenyl (meth)acrylate" in the art), dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate; (meth)acrylates containing a hydroxyl group such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; 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-methoxy 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[ 2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2. Bicyclic unsaturated compounds such as bis(cyclohexyloxycarbonyl)bis(cyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbis(cyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bis(cyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bis(cyclo[2.2.1]hept-2-ene; 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 dicarbonyl imide derivatives; 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. As (c), 2-ethylhexyl (meth)acrylate, dicyclopentane (meth)acrylate, benzyl (meth)acrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and the like are preferred. In terms of copolymerization reactivity and heat resistance, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and the like are more preferred.

Among all the structural units constituting the resin [K1], the ratio of the structural units derived from each in the resin [K1] is preferably: Structural unit derived from (a): 2 mol% to 60 mol% Structural unit derived from (b): 40 mol% to 98 mol% More preferably: Structural unit derived from (a): 10 mol% to 50 mol% Structural unit derived from (b): 50 mol% to 90 mol%. If the ratio of the structural units of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developing property when forming a colored pattern, and the solvent resistance of the obtained optical filter tend to be better.

The resin [K1] can be produced, for example, by referring to the method described in the document "Experimental Methods for Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Publishing Co., Ltd., 1st edition, 1st printing, published on March 1, 1972) and the cited documents described in the document.

Specifically, the following method can be cited: prescribed amounts of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, oxygen is replaced by nitrogen, for example, to create a deoxygenated environment, and the mixture is heated and kept warm while being stirred. The polymerization initiator and solvent used here are not particularly limited, and those commonly used in this field can be used. As the polymerization initiator, for example, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) can be cited, and as the solvent, any solvent that dissolves each monomer can be cited, and the solvent described later can be cited as the solvent (E).

Furthermore, the obtained copolymer may be used directly as a solution after the reaction, or as a concentrated or diluted solution, or as a solid (powder) obtained by reprecipitation or the like. In particular, the solvent contained in the coloring resin composition is used as a solvent during the polymerization, whereby the solution after the reaction can be directly used for the preparation of the coloring resin composition, thereby simplifying the production steps of the coloring resin composition.

Among all the structural units constituting the resin [K2], the ratio of the structural units derived from each in the resin [K2] is preferably: Structural unit derived from (a): 2 mol% to 45 mol% Structural unit derived from (b): 2 mol% to 95 mol% Structural unit derived from (c): 1 mol% to 65 mol% More preferably: Structural unit derived from (a): 5 mol% to 40 mol% Structural unit derived from (b): 5 mol% to 80 mol% Structural unit derived from (c): 5 mol% to 60 mol% If the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the coloring resin composition, the developing properties when forming a coloring pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained optical filter tend to be better.

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

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

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

Next, the cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a portion of the carboxylic acid and/or carboxylic anhydride derived from (a) in the copolymer. After the copolymer of (a) and (c) is produced, the atmosphere in the flask is replaced from nitrogen to air, and (b), a reaction catalyst of carboxylic acid or carboxylic anhydride and cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (e.g., hydroquinone, etc.) are placed in the flask, and the reaction is carried out at, for example, 60°C to 130°C for 1 hour to 10 hours, thereby producing the resin [K4]. The amount of (b) used is preferably 5 mol to 80 mol, more preferably 10 mol to 75 mol, relative to 100 mol of (a). By setting the amount within this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern tend to be improved. In terms of the high reactivity of the cyclic ether and the fact that unreacted (b) is not likely to remain, (b1) is preferably used as the (b) in the resin [K4], and further preferably (b1-1). The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted by considering the production equipment or the amount of heat generated by polymerization. In addition, similar to the polymerization conditions, the charging method or reaction temperature can be appropriately adjusted by considering the production equipment or the amount of heat generated by polymerization.

Regarding resin [K5], as the first stage, a copolymer of (b) and (c) is obtained in the same manner as the production method of the resin [K1]. As described above, the obtained copolymer can be used directly as a solution after the reaction, or as a concentrated or diluted solution, or can be used as a solid (powder) obtained by reprecipitation or the like. Relative to the total molar number of all structural units constituting the copolymer, the ratios of the structural units derived from (b) and (c) are preferably: Structural units derived from (b): 5 mol% to 95 mol% Structural units derived from (c): 5 mol% to 95 mol% More preferably: Structural units derived from (b): 10 mol% to 90 mol% Structural units derived from (c): 10 mol% to 90 mol%

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

Resin [K6] is a resin obtained by further reacting carboxylic acid anhydride with resin [K5]. Carboxylic acid anhydride and hydroxyl groups generated by the reaction of cyclic ether with carboxylic acid or carboxylic acid anhydride are reacted. Examples of carboxylic acid anhydride include succinic anhydride, maleic anhydride, succinic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride. The amount of carboxylic acid anhydride used is preferably 0.1 mol to 1 mol relative to 1 mol of (a).

Specific examples of the resin (B) include: 3,4-epoxyhexylmethyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid copolymers, and the like resins [K1]; 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymers, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymers, glycidyl (meth)acrylate/styrene/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymers, 3,4-epoxytricyclo[5.2.1.0 ^[K2 ]; resins such as benzyl (meth)acrylate/(meth)acrylic acid copolymers and styrene/(meth)acrylic acid copolymers [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate/(meth)acrylic acid copolymers, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymers, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymers, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymers, and resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymers. [K4]; a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate, a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate/styrene/glycidyl (meth)acrylate, etc. [K5]; a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate, further reacting with tetrahydrophthalic anhydride, a resin obtained by reacting (meth)acrylic acid with a copolymer of 2-ethylhexyl (meth)acrylate/glycidyl (meth)acrylate/dicyclopentane (meth)acrylate, further reacting with succinic anhydride, etc. [K6], etc. Among them, the resin (B) is preferably a copolymer comprising a structural unit derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides and a structural unit having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenic unsaturated bond (resin [K1] or resin [K2]) or resin [K6], and more preferably resin [K1] or resin [K2].

The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 500 to 100,000, more preferably 600 to 50,000, and still more preferably 700 to 30,000. When the molecular weight is within the above range, the hardness of the optical filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern is improved.

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

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

The content of the resin (B) relative to the total amount of the solid components of the coloring resin composition is preferably 7% to 80% by mass, more preferably 13% to 75% by mass, further preferably 17% to 70% by mass, further preferably 17% to 55% by mass. When the content of the resin (B) is within the above range, a coloring pattern can be formed, and the resolution and residual film rate of the coloring pattern tend to be improved. In addition, the content of the compound (I) relative to 100 parts by mass of the resin (B) is preferably 1 part by mass to 100 parts by mass, more preferably 8 parts by mass to 70 parts by mass, further preferably 15 parts by mass to 50 parts by mass.

<Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active free radicals and/or acids generated from the polymerization initiator (D), and examples thereof include polymerizable compounds having ethylenic unsaturated bonds, and preferably (meth)acrylate compounds.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trihydroxymethylpropane 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), isocyanuric acid tri(2-(meth)acryloyloxyethyl) ester, alkoxylated pentaerythritol poly(meth)acrylate (e.g., ethoxylated pentaerythritol tri(meth)acrylate, tetrapentaerythritol tri(meth)acrylate), and tetrapentaerythritol poly(meth)acrylate. Alkylated pentaerythritol poly(meth)acrylate (e.g., 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. Among them, it is preferred to include at least one selected from the group consisting of trihydroxymethylpropane tri(meth)acrylate and dipentaerythritol poly(meth)acrylate, and it is more preferred to include at least one selected from the group consisting of trihydroxymethylpropane triacrylate and dipentaerythritol polyacrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

The content of the polymerizable compound (C) is preferably 7% by mass to 65% by mass, more preferably 13% by mass to 60% by mass, and even more preferably 17% by mass to 55% by mass, relative to the total amount of the solid components of the coloring resin composition. When the content of the polymerizable compound (C) is within the above range, the residual film rate during the formation of the coloring pattern and the chemical resistance of the optical filter tend to be further improved.

<Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. to start polymerization by the action of light or heat, and a known polymerization initiator can be used.

Examples of the polymerization initiator that generates active free radicals include alkyl phenoxide compounds, triazine compounds, acyl phosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds.

The O-acyl oxime compound is a compound having a partial structure represented by formula (d1). Hereinafter, * represents a bond.

Examples of the O-acyl oxime compound include 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-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane -1-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzyloxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylthiophenyl]propane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, and the like. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (all manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, PBG-329 (all manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) may also be used. Among them, the O-acyl oxime compound is preferably selected from N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylthiophenyl]propane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetyloxy)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, Preferably, the present invention is at least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine. In the case of these O-acyl oxime compounds, an optical filter with high brightness tends to be obtained.

The phenylalkyl ketone compound is a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have a substituent.

Examples of the compound having a partial structure represented by formula (d2) include 2-methyl-2-morpholinyl-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinylphenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butane-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can also be used.

Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-〔4-(2-hydroxyethoxy)phenyl〕propane-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzoyl dimethyl ketal. In terms of sensitivity, the phenyl alkyl ketone compound is preferably a compound having a partial structure represented by formula (d2).

Examples of the triazine compound 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-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, [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.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, azole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, see Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. 62-174204, etc.), biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (for example, see Japanese Patent Publication No. 7-10913, etc.), and the like.

Furthermore, the polymerization initiator (D) includes benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzoyl, methyl phenylglyoxylate, and titaniumocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) (particularly amines) described later.

Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyldimethylzincium p-toluenesulfonate, 4-hydroxyphenyldimethylzincium hexafluoroanticorbic acid salt, 4-acetoxyphenyldimethylzincium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylzincium hexafluoroanticorbic acid salt, triphenylzincium p-toluenesulfonate, triphenylzincium hexafluoroanticorbic acid salt, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroanticorbic acid salt, nitrobenzyl toluenesulfonate salts, and benzoin toluenesulfonate salts.

The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of an alkyl phenoxide compound, a triazine compound, an acyl phosphine oxide compound, an O-acyl oxime compound and a biimidazole compound, and more preferably a polymerization initiator comprising an O-acyl oxime compound.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be high and the exposure time tends to be shortened, thereby improving the productivity of the optical filter.

<Polymerization initiator (D1)> The polymerization initiator (D1) is a compound or sensitizer for promoting the polymerization of a polymerizable compound that starts polymerization by the polymerization initiator. When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D). As the polymerization initiator (D1), there can be listed: amine compounds, alkoxyanthracene compounds, thioxanone compounds and carboxylic acid compounds.

Examples of the amine compound 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, and 4,4'-bis(ethylmethylamino)benzophenone. Among them, 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

Examples of the thiothione compound include 2-isopropylthiothione, 4-isopropylthiothione, 2,4-diethylthiothione, 2,4-dichlorothiothione, and 1-chloro-4-propoxythiothione.

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, and the like.

When the polymerization initiator (D1) is used, the content of the polymerization initiator (D1) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiator (D1) is within the above range, a colored pattern can be formed with high sensitivity, and the productivity of the optical filter tends to be improved.

<Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used. For example, ester solvents (solvents containing -COO- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -COO- in the molecule), alcohol solvents (solvents containing OH and not containing -O-, -CO- and -COO- in the molecule), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc.

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 acetylacetate, ethyl acetylacetate, cyclohexanol acetate, and γ-butyrolactone.

As the ether solvent, there can be listed: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether and methyl anisole.

As the ether ester solvent, there can be mentioned methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate and diethylene glycol monobutyl ether acetate.

Examples of 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.

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

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

Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone.

Among the above solvents, an organic solvent having a boiling point of 120° C. or higher and 180° C. or lower at 1 atm is preferred in terms of coating properties and drying properties. 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.

The content of the solvent (E) is preferably 70% by mass to 95% by mass, more preferably 75% by mass to 92% by mass, relative to the total amount of the coloring resin composition. In other words, the solid content of the coloring resin composition is preferably 5% by mass to 30% by mass, more preferably 8% by mass to 25% by mass. When the content of the solvent (E) is within the above range, the flatness during coating is improved, and the color concentration is not insufficient when forming an optical filter, so that the display characteristics or sensitivity tend to be improved.

<Leveling agent (F)> As the leveling agent (F), there can be listed: silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may also have polymerizable groups on the side chains.

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

As the fluorine-based surfactant, there can be cited surfactants having a fluorine-carbon chain in the molecule. Specifically, there can be cited: Fluorad (registered trademark) FC430, Fluorad (Fluorad) FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS- 718-K (manufactured by DIC Corporation), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by AGC Corporation (formerly Asahi Glass Corporation)), and E5844 (manufactured by Daikin Fine Chemical Laboratories, Ltd.), etc.

Examples of the silicone-based surfactants having fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in the molecule. Specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, and Megafac F443 (manufactured by DIC Corporation) are listed.

The content of the leveling agent (F) relative to the total amount of the coloring resin composition is preferably 0.001 mass % to 0.2 mass %, more preferably 0.002 mass % to 0.1 mass %, and further preferably 0.005 mass % to 0.05 mass %. In addition, the content does not include the content of the pigment dispersant described later. If the content of the leveling agent (F) is within the above range, the flatness of the optical filter can be improved.

<Other ingredients> The coloring resin composition may also contain fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and other additives known in the art as needed.

<Method for producing a coloring resin composition> The coloring resin composition can be prepared by, for example, mixing a coloring agent (A) and a resin (B), and optionally, a polymerizable compound (C), a polymerization initiator (D), a solvent (E), a leveling agent (F), a polymerization initiation aid (D1), and other components. It is preferred to filter the mixed coloring resin composition using a filter having a pore size of about 0.01 μm to 10 μm.

The compound (I) as the colorant (A) and the pigment used as required can be dispersed by containing a pigment dispersant to be used as a dispersion in a state of being uniformly dispersed in a solution. The target coloring resin composition can be prepared by mixing the remaining components in such a dispersion to a predetermined concentration. The compound (I) and the pigment can be dispersed individually or in combination.

As the pigment dispersant, surfactants can be listed, which can be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, polyester-based, polyamine-based and acrylic-based surfactants can be listed. These dispersants can be used alone or in combination of two or more. Dispersants that are indicated by trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark), BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), etc.

When a pigment dispersant is used, the amount of the pigment dispersant used is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 15 parts by mass or more and 180 parts by mass or less, and further preferably 20 parts by mass or more and 160 parts by mass or less, relative to 100 parts by mass of the compound (I) and the pigment in the dispersion. If the amount of the pigment dispersant used is within the above range, a dispersion having a more uniform dispersion state tends to be obtained.

When the coloring agent (A) includes a dye, the dye may be dissolved in part or all of the solvent (E) to prepare a solution. The solution is preferably filtered using a filter having a pore size of about 0.01 μm to 1 μm.

[Optical filter] As methods for producing the 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 applying the colored resin composition on a substrate, drying it to form a composition layer, and exposing and developing the composition layer through a photomask. In photolithography, a coating film that is a cured product of the composition layer can be formed by not using a photomask and/or not developing during exposure.

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, further preferably 3 μm or less, further preferably 1.5 μm or less, particularly preferably 0.5 μm or less, and preferably 0.1 μm or more, more preferably 0.2 μm or more, further preferably 0.3 μm or more.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, sodium calcium glass with silicon dioxide coating on the surface, or resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, or aluminum, silver, silver/copper/palladium alloy thin films, etc. can be used. Other optical filter layers, resin layers, transistors, circuits, etc. can also be formed on these substrates. In addition, a substrate formed by treating a silicon substrate with hexamethyl disilazane (HMDS) can also be used.

The formation of coatings or patterns by photolithography can be performed by known or customary devices or conditions. For example, it can be produced as follows. First, a colored resin composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and/or reduced pressure drying to obtain a smooth composition layer. Examples of coating methods include spin coating, slit coating, slit and spin coating, etc. The temperature during heat drying is preferably 30°C to 120°C, and more preferably 50°C to 110°C. In addition, the heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. When the reduced pressure drying is performed, it is preferably performed at a pressure of 50 Pa to 150 Pa and a temperature range of 20° C. to 25° C. The film thickness of the component layer is not particularly limited and can be appropriately selected according to the film thickness of the target optical filter.

Secondly, the composition layer is separated by a photomask for forming a target pattern for exposure. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target purpose can be used. As the light source used in the exposure, a light source that generates light with a wavelength of 250 nm to 450 nm is preferably used. For example, a filter that cuts off the wavelength range can be used to cut off light less than 250 nm, or a bandpass filter that extracts light in the wavelength range near 436 nm, 408 nm, and 365 nm can be used to selectively extract light. Specifically, the following can be listed: mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, etc. In order to evenly irradiate the entire exposure surface with parallel light or accurately align the mask and the substrate, it is preferable to use a reduced projection exposure device or a proximity exposure device such as a mask aligner and a stepper.

The exposed component layer is brought into contact with a developer to form a pattern on the substrate. By developing, the unexposed part of the component layer is dissolved in the developer and removed. As the developer, for example, an aqueous solution of alkaline compounds 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 mass% to 10 mass%, and more preferably 0.03 mass% to 5 mass%. Furthermore, the developer may also contain a surfactant. The developing method may be any of a coating method, an immersion method, and a spray method. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferred to wash with water.

Preferably, the obtained pattern or coating is further post-baked. The post-baking temperature is preferably 80°C to 250°C, more preferably 100°C to 245°C. The post-baking time is preferably 1 minute to 120 minutes, more preferably 2 minutes to 30 minutes.

The patterns and coatings thus obtained are effectively used as optical filters, and can be suitably used in near-infrared transmission filters or color filters such as primary color filters (RGB filters) and complementary color filters (CMY filters) used in display devices (e.g., liquid crystal display devices, organic electroluminescence (EL) devices, etc.), electronic paper, solid-state imaging elements, etc.

In particular, in recent years, solid-state imaging elements that sense near-infrared rays are being studied in cameras and sensors such as smartphones, surveillance cameras, car cameras, cameras for the Internet of Things (IoT), and infrared sensors. The optical filter formed by the colored resin composition of the present invention preferably has a steep drop in absorbance on the long-wavelength side from λ _max in the wavelength range of 750 nm to 900 nm (the steepness of the slope on the long-wavelength side from λ _max is improved). The higher the steepness of the slope, the easier it is to increase the absorbance in the visible region (especially the visible region on the long-wavelength side), thereby increasing the sensitivity to near-infrared rays, and therefore it can also be suitably used as a near-infrared transmission filter in a solid-state imaging element. In addition, the steeper the slope is, the better the sensitivity can be achieved near 940 nm where the influence of sunlight is small, and thus it can be suitably used as a near-infrared transmission filter in a solid-state imaging element that is not easily affected by near-infrared rays generated by the sun. [Example]

The present invention is described in more detail below by way of examples, but the present invention is not limited to the following examples and can be implemented with appropriate modifications within the scope of the above/later described subject matter, all of which are included in the technical scope of the present invention. Furthermore, below, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

The structures of the compounds were confirmed by mass analysis (Matrix Assisted Laser Desorption Ionization (MALDI)-Time of Flight Mass Spectrometry (TOF MS); JMS-S3000, JEOL Ltd.).

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were determined by gel permeation chromatography (GPC) under the following conditions. Device: HLC-8120GPC (manufactured by Tosoh Co., Ltd.) Column: TSK-GELG2000HXL Column temperature: 40°C Solvent: tetrahydrofuran Flow rate: 1.0 mL/min Solid content concentration of the analyzed sample: 0.001 mass% to 0.01 mass% Injection volume: 50 μL Detector: RI Calibration standard substances: TSK standard polystyrene F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.)

The ratio (Mw/Mn) of the obtained polystyrene-equivalent weight average molecular weight and number average molecular weight was defined as the dispersion degree.

[Synthesis of coloring agent] (Example 1: Synthesis of compound (3)) <Preparation of compound (1)> In a nitrogen atmosphere, 1.0 parts of aluminum chloride (manufactured by Fuji Films Wako Pure Chemical Industries, Ltd.), 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 the reaction solution was cooled to room temperature, 75 parts of ethyl acetate were added. The obtained precipitate was obtained as a residue by suction filtration, washed with 75 parts of ethyl acetate, and then washed with 150 parts of ion-exchanged water. The obtained 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)).

Identification (mass analysis) of compound (1) Ionization mode = MALDI-TOF ^- : m/z = 774 Exact Mass: 774

<Preparation of Compound (2)> The compound represented by Formula (2) (hereinafter referred to as Compound (2)) is 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.

<Preparation of compound (3)> 1.0 parts of compound (1), 0.3 parts 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, heated to 150°C and stirred for 10 hours. After cooling the reaction solution to room temperature, 50 parts of ethyl acetate were added. The obtained precipitate was obtained as a residue after suction filtration and washed with 50 parts of ethyl acetate. 50 parts of ethyl acetate were added to the obtained residue and stirred, and then the residue was filtered and washed with 50 parts of ethyl acetate. The obtained residue was dried under reduced pressure at 60°C to obtain 1.0 parts of the compound represented by formula (3) (hereinafter referred to as compound (3)).

Identification (mass analysis) of compound (3) Ionization mode = MALDI-TOF ^- : m/z = 940 Exact Mass: 940

(Example 2: Synthesis of Compound (6)) <Preparation of Compound (4)> The compound represented by Formula (4) (hereinafter referred to as Compound (4)) is 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.

<Preparation of Compound (5)> 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 Publication No. 2012-507743 except that 1-chloronaphthalene, urea, 4-fluorophthalonitrile and aluminum trichloride as raw materials were changed to 2.1 parts of 1-chloronaphthalene, 0.008 parts of urea, 1.0 parts of 2,3-dibromo-6,7-dicyanonaphthalene (produced by Tokyo Chemical Industry Co., Ltd.) and 0.11 parts of aluminum trichloride.

Identification (mass analysis) of compound (5) Ionization mode = MALDI-TOF ^- : m/z = 1397 Exact Mass: 1397

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

Identification (mass analysis) of compound (6) Ionization mode = MALDI-TOF ^- : m/z = 1567 Exact Mass: 1567

(Example 3: Synthesis of compound (8)) <Preparation of compound (7)> The compound represented by formula (7) was synthesized by the same method as described in [0071] to [0072] of Japanese Patent Publication No. 2012-507743 except that 1-chloronaphthalene, urea, 4-fluorophthalonitrile and aluminum trichloride as raw materials were changed to 4.0 parts of 1-chloronaphthalene, 0.015 parts of urea, 1.5 parts of 6-bromo-2,3-dicyanonaphthalene (produced by Tokyo Chemical Industry Co., Ltd.) and 0.20 parts of aluminum trichloride.

Identification (mass analysis) of compound (7) Ionization mode = MALDI-TOF ^- : m/z = 1086 Exact Mass: 1086

<Preparation of compound (8)> 0.18 parts of compound (4) and 8.0 parts of NMP were mixed at room temperature, heated to 50°C, and then 0.80 parts of compound (7) were added. The temperature was raised to 150°C and stirred for 10 hours. After the reaction solution was cooled to room temperature, the obtained reaction solution was added to 80 parts of ion-exchanged water. The obtained precipitate was obtained as a residue by suction filtration, washed with 25 parts of ion-exchanged water, and then dried under reduced pressure at 60°C to obtain 0.98 parts of the compound represented by formula (8) (hereinafter referred to as compound (8)).

Identification (mass analysis) of compound (8) Ionization mode = MALDI-TOF ^- : m/z = 1256 Exact Mass: 1256

(Comparative Example 1: Synthesis of Compound (x1)) The compound represented by formula (x1) (hereinafter referred to as compound (x1)) was obtained by the synthesis method described in Japanese Patent Publication No. 2022-72558.

Identification (mass analysis) of compound (x1) Ionization mode = MALDI-TOF ^- : m/z = 988 Exact Mass: 988

[Synthesis of Resin] (Preparation of Resin (B-1)) A suitable amount of nitrogen was introduced into a flask equipped with a reflux cooler, a dropping funnel and a stirrer to replace the atmosphere with a nitrogen atmosphere, and 340 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C while stirring. Subsequently, 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 ratio of 1:1 in molar ratio), 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 polymerization initiator 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 kept at 80°C for 3 hours and then cooled to room temperature (18°C to 24°C) to obtain a copolymer (resin (B-1)) solution having a viscosity of 127 mPa·s and a solid content of 37.0% as measured by a B-type viscometer (23°C). The weight average molecular weight Mw of the generated copolymer was 9.4×10 ³ , the degree of dispersion was 1.89, and the acid value calculated as solid content was 114 mg-KOH/g. Resin (B-1) has the following structural units.

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

(Dispersion Preparation Example 2 to Dispersion Preparation Example 3) Dispersions (A-2) to (A-3) were obtained by the same method as in Dispersion Preparation Example 1 except that the compound (3) obtained in Example 1 was replaced with the following compound. Dispersion Preparation Example 2 (Preparation of Dispersion (A-2)): Compound (6) obtained in Example 2 Dispersion Preparation Example 3 (Preparation of Dispersion (A-3)): Compound (8) obtained in Example 3

(Example 4 for preparing dispersion) 5 parts of the compound (x1) obtained in Comparative Example 1, 4 parts of a dispersant (BYK LPN-6919 manufactured by BYK) (converted as solid content), 4 parts of a resin (B-1) (converted as solid content), and 87 parts of propylene glycol monomethyl ether acetate were mixed, and 300 parts of 0.2 μm zirconia beads were added. The mixture was shaken for 1 hour using a paint mixer (manufactured by LAU). The zirconia beads were then removed by filtration to obtain a dispersion (X-1).

(Example 1A) <Preparation of coloring resin composition 1> The coloring resin composition 1 is obtained by mixing the following components. Dispersion (A-1)                                                                         415 parts Resin (B-1) (solid content conversion)                                             48 parts Polymerizable compound (C-1): dipentaerythritol polyacrylate: trade name A-9550: manufactured by Shin-Nakamura Chemical Industry Co., Ltd.                                                                 20 parts Polymerizable compound (C-2): trihydroxymethylpropane triacrylate: trade name A-TMPT: manufactured by Shin-Nakamura Chemical Industry Co., Ltd.                                             20 parts Polymerization initiator (D): N-acetyloxy-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.)     ...

<Formation of coating film> The coloring resin composition 1 was applied by spin coating on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning) and then pre-baked at 100°C for 2 minutes to obtain a coating film. Thereafter, the pre-baked coating film was post-baked at 230°C for 5 minutes.

(Reliability evaluation) For the coating after post-baking, a colorimeter (OSP-SP-200; manufactured by Olympus) was used to measure the spectrum at 5 nm intervals within the wavelength range of 380 nm to 780 nm, and the spectra before and after the solvent resistance test/heat resistance test/light resistance test were obtained.

(1) Solvent resistance test The obtained coating was immersed in propylene glycol monomethyl ether (PGME) or 2-butanone (MEK) at room temperature for 5 minutes, and the absorbance maintenance rate of the coating before and after immersion was measured. Here, the absorbance maintenance rate refers to the value calculated according to the following formula. The higher the absorbance maintenance rate, the better the solvent resistance. In addition, if the solvent resistance of the coating is good, it can be said that the solvent resistance of the optical filter made of the same coloring resin composition is also excellent. Absorbance maintenance rate (%) = (absorbance of the coating after immersion at the maximum absorption wavelength) / (absorbance of the coating before immersion at the maximum absorption wavelength) × 100 In Example 1A, the absorbance maintenance rate when immersed in MEK is 100%, which is a higher value than the absorbance maintenance rate (85%) of Comparative Example 1A described later. In addition, in Example 1A, the absorbance maintenance rate when immersed in PGME is also 100%, which is a higher value than the absorbance maintenance rate (97%) of Comparative Example 1A described later.

(2) Heat resistance test The obtained coating film was heated at 260°C for 10 minutes in an oven in an atmospheric environment, and the absorbance maintenance rate of the coating film before and after heating was measured. Here, the absorbance maintenance rate refers to the value calculated according to the following formula. The higher the absorbance maintenance rate, the better 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. Absorbance maintenance rate (%) = (absorbance of the coating after heating at the maximum absorption wavelength) / (absorbance of the coating before heating at the maximum absorption wavelength) × 100 In Example 1A, the absorbance maintenance rate is 84%, which is a higher value than the absorbance maintenance rate (77%) of Comparative Example 1A described later.

(3) Light resistance test A UV cut filter (Colored Optical Glass L38, manufactured by Hoya Co., Ltd., a filter that cuts off light below 380 nm) was placed on the obtained coating film, and the coating film was irradiated with xenon light for 68 hours using a light resistance tester (Suntest CPS+, manufactured by Toyo Seiki Seisaku-sho Co., Ltd.). The absorbance maintenance rate of the coating film before and after irradiation was measured. Here, the absorbance maintenance rate refers to a value calculated according to the following formula. The higher the absorbance maintenance rate, the better 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 from the same coloring resin composition is also excellent. Absorbance maintenance rate (%) = (absorbance of the coating after irradiation at the maximum absorption wavelength) / (absorbance of the coating before irradiation at the maximum absorption wavelength) × 100 In Example 1A, the absorbance maintenance rate is 84%, which is a higher value than the absorbance maintenance rate (75%) of Comparative Example 1A described later.

(Spectral evaluation) The coating after post-baking was measured at 5 nm intervals in the wavelength range of 300 nm to 900 nm using an ultraviolet-visible near-infrared absorption spectrometer (JASCO Corporation: V-770). 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 nm to 900 nm, the absorption wavelength λ _0.2 at which the absorbance became 0.20 (Abs(λ _0.2 )) was determined, and the slope between the two points was calculated based on the following formula. Slope (/nm) = |(Abs(λ _max )-Abs(λ _0.2 ))/(λ _max -λ _0.2 )| The larger the value, the easier it is to improve the absorbance in the visible region (especially the visible region on the long wavelength side), and the higher the sensitivity of the sensor, so it is better as a characteristic of an optical filter with near-infrared transmittance. The slope in Example 1A is 0.028/nm, which is larger than the slope (0.022/nm) of Comparative Example 1A described later.

(Example 2A) Except that the dispersion (A-1) was changed to the dispersion (A-2), a coating film was formed by the same method as in Example 1A, and various physical properties were evaluated. In Example 2A, the absorbance maintenance rate when immersed in MEK measured by the same method as in the (1) solvent resistance test was 93%, which is a higher value than the absorbance maintenance rate (85%) of the comparative example 1A described later. In addition, in Example 2A, the absorbance maintenance rate when measured by the same method as in the (2) heat resistance test was 93%, which is a higher value than the absorbance maintenance rate (77%) of the comparative example 1A described later. In addition, in Example 2A, the absorbance maintenance rate when measured using the same method as the light resistance test (3) is 100%, which is a higher value than the absorbance maintenance rate (75%) of Comparative Example 1A described later.

(Example 3A) Except that the dispersion (A-1) was changed to the dispersion (A-3), a coating was formed by the same method as in Example 1A, and various physical properties were evaluated. In Example 3A, the absorbance maintenance rate when immersed in MEK measured by the same method as in the above-mentioned (1) solvent resistance test was 100%, which was a higher value than the absorbance maintenance rate (85%) of Comparative Example 1A described later. In addition, the absorbance maintenance rate when immersed in PGME was 100%, which was a higher value than the absorbance maintenance rate (97%) of Comparative Example 1A described later. In addition, in Example 3A, the absorbance maintenance rate when measured by the same method as the (2) heat resistance test is 92%, which is a higher value than the absorbance maintenance rate (77%) of the comparative example 1A described later. In addition, in Example 3A, the absorbance maintenance rate when measured by the same method as the (3) light resistance test is 96%, which is a higher value than the absorbance maintenance rate (75%) of the comparative example 1A described later.

(Comparative Example 1A) Except that the dispersion (A-1) was changed to the dispersion (X-1), a coating film was formed by the same method as in Example 1A, and various physical properties were evaluated. In Comparative Example 1A, the absorbance maintenance rate when immersed in MEK measured by the same method as the above-mentioned (1) solvent resistance test was 85%. In addition, the absorbance maintenance rate when immersed in PGME was 97%. In addition, in Comparative Example 1A, the absorbance maintenance rate when measured by the same method as the above-mentioned (2) heat resistance test was 77%. In addition, in Comparative Example 1A, the absorbance maintenance rate when measured by the same method as the above-mentioned (3) light resistance test was 75%. In addition, in Comparative Example 1A, the value of the slope obtained by the above-mentioned spectrum evaluation was 0.022/nm.

Claims (6)

A compound represented by formula (I); In formula (I), ^R1 represents an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, ^R2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a single bond linking ^Z2 to ^R1 ; ^Z1 and ^Z2 each independently represent a single bond or an oxygen atom; ^X1 to ^X4 each independently represent ^-R3 , ^-OR3 , ^-SR3 , a halogen atom, a nitro group, or an aminosulfonyl group which may have a substituent; ^R3 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent; n1 to n4 each independently represent an integer of 0 to 6. A coloring resin composition comprises the compound as described in claim 1 and a resin. The colored resin composition as described in claim 2 further contains at least one of a polymerizable compound and a polymerization initiator. An optical filter is formed from the colored resin composition as described in claim 3. A solid-state imaging element comprises an optical filter as described in claim 4. A display device comprising the optical filter as described in claim 4.