JP2024091468A - Colored curable composition, color filter, and display device - Google Patents

Abstract

The present invention provides a colored curable composition capable of forming a cured coating film that is resistant to surface roughening due to an ashing treatment.
[Solution] The colored curable composition contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), composite oxide particles (E), and a solvent (F), in which the polymerization initiator (D) contains an O-acyloxime compound, and the composite oxide particles (E) are oxide particles represented by the formula _ABO3 (in the formula, A represents a Group 2 metal atom, and B represents a Group 4 metal atom).
[Selection diagram] None

Description

The present invention relates to a colored curable composition, a color filter, and a display device.

Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays; and solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored curable compositions. As such colored curable compositions, inks for color filters containing colorants, resin materials, and the like are known (for example, Patent Document 1).

JP 2010-286692 A

In the film formation process of color filters, an ashing treatment is sometimes performed on the surface of a cured coating film. The ashing treatment refers to a treatment in which the surface of the cured coating film is irradiated with high-energy oxygen plasma, and unnecessary carbon atoms and oxygen atoms in the cured coating film are reacted with each other, and are vaporized and decomposed as _CO2 . However, the surface of a cured coating film formed using a conventional colored curable composition may become rough due to the ashing treatment.

The main objective of the present invention is to provide a colored curable composition capable of forming a cured coating film that is less susceptible to surface roughening due to ashing treatment.

The present invention provides a colored curable composition according to [1], a color filter according to [2], and a display device according to [3].
[1] A colored curable composition comprising a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), composite oxide particles (E), and a solvent (F), wherein the polymerization initiator (D) contains an O-acyloxime compound, and the composite oxide particles (E) are oxide particles represented by the formula _ABO3 (wherein A represents a Group 2 metal atom and B represents a Group 4 metal atom).
[2] A color filter formed from the colored curable composition according to [1].
[3] A display device comprising the color filter according to [2].

According to the present invention, a colored curable composition capable of forming a cured coating film that is less likely to develop surface roughness due to an ashing process is provided. In addition, according to the present invention, a color filter formed from such a colored curable composition and a display device including the color filter are provided.

The following describes in detail the embodiments of the present invention. However, the present invention is not limited to the following embodiments.

In this specification, a numerical range indicated using "~" indicates a range that includes the numerical values before and after "~" as the minimum and maximum values, respectively. In numerical ranges described in stages in this specification, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. In addition, in numerical ranges described in this specification, the upper or lower limit value of the numerical range may be replaced with a value shown in the examples.

In this specification, (meth)acrylate means acrylate or the corresponding methacrylate. The same applies to other similar expressions such as (meth)acrylic acid, (meth)acryloyl, and (meth)acrylic acid esters.

Unless otherwise specified, the materials exemplified below may be used alone or in combination of two or more types within the range that meets the conditions. When multiple substances corresponding to each component are present, the content of each component means the total amount of the multiple substances unless otherwise specified.

[Colored curable composition]
The colored curable composition of the present embodiment contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), composite oxide particles (E), and a solvent (F). The colored curable composition of the present embodiment may further contain a polymerization initiator assistant (D1), a leveling agent (G), and the like.

<Colorant (A)>
The colored curable composition of the present embodiment contains a colorant (A). The colorant (A) preferably contains at least one compound selected from the group consisting of a xanthene compound, a phthalocyanine compound, a quinophthalone compound, an isoindoline compound, an azo compound, a diketopyrrolopyrrole compound, a perylene compound, a dioxazine compound, an anthraquinone compound, a squarylium compound, a cyanine compound, and a coumarin compound, more preferably contains at least one compound selected from the group consisting of a xanthene compound, a phthalocyanine compound, a quinophthalone compound, an isoindoline compound, an azo compound, a diketopyrrolopyrrole compound, a perylene compound, a dioxazine compound, and an anthraquinone compound, more preferably contains a xanthene compound or a phthalocyanine compound, particularly preferably contains a phthalocyanine compound. Each compound may be a dye or a pigment.

Xanthene compounds are compounds that have a xanthene skeleton in the molecule. Examples of xanthene compounds include Acid Red 52; C.I. Pigment Red 81, 81:1, 169, 173; and C.I. Pigment Violet 1.

An example of a xanthene compound is a compound represented by formula (I) (hereinafter, sometimes referred to as "compound (I)"). Compound (I) may be a tautomer thereof.

In formula (I), R ¹ to R ⁴ each independently represent a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and -CH ₂ - contained in the saturated hydrocarbon group may be substituted with -O-, -CO- or -NR ¹¹ -.
^R5 represents -OH _{, -SO3-} ^, _-SO3H ^, _-SO3 ^- Z ⁺ _, ^-CO2H , _{-CO2- Z} ⁺ , -CO2R8 _, ^-SO3R8 , ^{or -SO2NR9R10 .}
R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
m represents an integer of 0 to 5. When m is 2 or more, multiple R ^5s may be the same or different.
a represents an integer of 0 or 1.
X represents a halogen atom.
Z ⁺ represents ⁺ N(R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and the four R ¹¹ may be the same or different.
R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
R ⁹ and R ¹⁰ each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, in which -CH ₂ - contained in the saturated hydrocarbon group may be substituted with -O-, -CO-, -NH- or -NR ⁸ -, and R ⁹ and R ¹⁰ may be bonded to form a 3- to 10-membered heterocycle together with the adjacent nitrogen atom.
R ¹¹ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ¹ to R ⁴ include linear alkyl groups such as methyl, ethyl, propyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and icosyl groups; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl groups; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl groups. The number of carbon atoms in the saturated hydrocarbon group includes the number of carbon atoms in the substituent, if any. Examples of the substituent that the saturated hydrocarbon group may have include a halogen atom, -OH, -OR ⁸ , -SO ₃ ^- , -SO ₃ H, -SO ₃ ^- Z ⁺ , -CO ₂ H, -CO ₂ R ⁸ , -SR ⁸ , -SO ₂ R ⁸ , -SO ₃ R ⁸ , -SO ₂ NR ⁹ R ¹⁰ , and -Si(OR ¹² )(OR ¹³ )(OR ¹⁴ ). R ¹² , R ¹³ , and R ¹⁴ each independently represent a monovalent saturated hydrocarbon group having 1 to 4 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.

Examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms in R ¹ to R ⁴ include a phenyl group, a biphenyl group, a triphenyl group (o-terphenyl group, m-terphenyl group, p-terphenyl group), etc. Examples of the monovalent aromatic hydrocarbon group having a substituent include a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, a butylphenyl group, etc. When the aromatic hydrocarbon group has a substituent, the number of carbon atoms in the substituent is the number including the carbon atoms in the substituent. Examples of substituents that the aromatic hydrocarbon group may have include a halogen atom, -R ⁸ , -OH, -OR ⁸ , -SO ₃ ^- , -SO ₃ H, -SO ₃ ^- Z ⁺ , -CO ₂ H, -CO ₂ R ⁸ , -SR ⁸ , -SO ₂ R ⁸ , -SO ₃ R ⁸ , -SO ₂ NR ⁹ R ¹⁰ , or -Si(OR ¹² )(OR ¹³ )(OR ¹⁴ ).

Examples of the monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms for R ⁸ to R ¹¹ include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and icosyl groups; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl groups; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl groups.

The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ⁹ and R ¹⁰ may have a substituent, such as a hydroxy group or a halogen atom.

Examples of the monovalent saturated hydrocarbon group having 1 to 4 carbon atoms for R ¹² to R ¹⁴ include linear alkyl groups such as a methyl group, an ethyl group, a propyl group, and a butyl group; branched alkyl groups such as an isopropyl group and an isobutyl group; and alicyclic saturated hydrocarbon groups having 3 to 4 carbon atoms such as a cyclopropyl group.

Z ⁺ is N ⁺ ( ^R11 ) ₄ , Na ⁺ or K ⁺ , and is preferably N ⁺ ( ^R11 ) ₄ . Of the four ^R11 in N ⁺ ( ^R11 ) ₄ , it is preferred that at least two are monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. The total number of carbon atoms of the four ^R11 is preferably 20 to 80, and more preferably 20 to 60.

Examples of --OR ⁸ include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, and an icosyloxy group.

Examples of --CO ₂ R ⁸ include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.

Examples of --SR ⁸ include a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, and an icosylsulfanyl group.

Examples of --SO ₂ R ⁸ include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group.

Examples of --SO ₃ R ⁸ include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group.

Examples of —SO ₂ NR ⁹ R ¹⁰ include a sulfamoyl group; an N-methylsulfamoyl group, an N-ethylsulfamoyl group, an N-isopropylsulfamoyl group, an N-butylsulfamoyl group, an N-pentylsulfamoyl group, an N-(1-ethylpropyl)sulfamoyl group, an N-(1,1-dimethylpropyl)sulfamoyl group, an N-(2-methylbutyl)sulfamoyl group, an N-cyclopentylsulfamoyl group, an N-hexylsulfamoyl group, an N-(3,3-dimethylbutyl)sulfamoyl group, an N-(1- N-1 substituted sulfamoyl groups such as N-(methylhexyl)sulfamoyl group, N-octylsulfamoyl group, N-(2-ethylhexyl)sulfamoyl group, and N-(1,1,2,2-tetramethylbutyl)sulfamoyl group; and N,N-2 substituted sulfamoyl groups such as N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, N,N-bis(1-methylpropyl)sulfamoyl group, and N,N-heptylmethylsulfamoyl group.

Examples of —Si(OR ¹² )(OR ¹³ )(OR ¹⁴ ) include a trimethoxysilyl group and a triethoxysilyl group.

R ⁵ is preferably —CO ₂ H, —CO ₂ ⁻ Z ⁺ , —CO ₂ R ⁸ , —SO ₃ ⁻ , —SO ₃ ⁻ Z ⁺ , —SO ₃ H or SO ₂ NHR ⁹ , more preferably SO ₃ ⁻ , —SO ₃ ⁻ Z ⁺ , —SO ₃ H or SO ₂ NHR ⁹ .

m represents an integer from 0 to 5, preferably 1 to 4, more preferably 1 or 2, and even more preferably 1.

Examples of the alkyl group having 1 to 6 carbon atoms in ^R6 and ^R7 include the alkyl groups exemplified above that have 1 to 6 carbon atoms. The alkyl group having 1 to 6 carbon atoms in ^R6 and ^R7 is preferably an alkyl group having 1 to 2 carbon atoms. It is more preferable that ^R6 and ^R7 are hydrogen atoms.

Examples of the aralkyl group having 7 to 10 carbon atoms for R ¹¹ include a benzyl group, a phenylethyl group, and a phenylbutyl group.

a represents an integer of 0 or 1, preferably 0.

In compound (I), R ¹ and R ⁴ are each independently a monovalent aromatic hydrocarbon group which may have one or two monovalent saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms, and R ² and R ³ are each independently a hydrogen atom, a methyl group, or an ethyl group.

Examples of compound (I) include compounds 1 to 38 and compounds represented by formulas A3-1 to A3-8, which are specified in formula (IaX) and Table 1 or Table 2.

The symbols in the table represent the following groups (below, * represents a bond).

Phthalocyanine compounds are compounds that have a phthalocyanine skeleton in the molecule. Examples of phthalocyanine compounds include C.I. Pigment Green 7, 36, 58, 59, 62, and 63; and C.I. Pigment Blue 15:1, 15:2, 15:3, 15:4, 15:6, 16, and 75.

Examples of phthalocyanine compounds include a compound represented by formula (II) (hereinafter, sometimes referred to as "compound (II)") and a compound represented by formula (III) (hereinafter, sometimes referred to as "compound (III)").

In formula (II),
R ²¹ represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent;
R ²² represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a single bond connecting Z ²² and R ²¹ .
Z ²¹ and Z ²² each independently represent a single bond or an oxygen atom.
X ²¹ to X ²⁴ each independently represent -R ²⁴ , -OR ²⁴ , -SR ²⁴ , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent.
R ²⁴ represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
n21 to n24 each independently represent an integer of 0 to 4.
In formula (III),
R ²³ represents an optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms.
Z ²³ represents a single bond or an oxygen atom.
X ²⁵ to X ³² each independently represent -R ²⁵ , -OR ²⁵ , -SR ²⁵ , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent.
R ²⁵ represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
n25 to n32 each independently represent an integer of 0 to 4.

The unsaturated hydrocarbon group represented by ^R21 has 2 to 20 carbon atoms, preferably 2 to 10, more preferably 2 to 7, and even more preferably 2 to 5. The lower limit of the carbon number may be 3 or 4, and the upper limit of the carbon number may be 8.

The unsaturated hydrocarbon group represented by R ²¹ may be an aliphatic unsaturated hydrocarbon group, and may be a chain or cyclic (alicyclic hydrocarbon group).

The unsaturated chain hydrocarbon group represented by ^R21 may be linear or branched, and specifically,
Ethenyl group (vinyl group), propenyl group (for example, 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (for example, 1-butenyl group, 2-butenyl group, 3-butenyl group), 3-methyl-1-butenyl group, 1-methyl-1-butenyl group, 3-methyl-2-butenyl group, 1,3-butadienyl group, 3-methyl-1,2-butadienyl group, 1-(2-propenyl)ethenyl group, 1-(1-methylethenyl)ethenyl group, 1,1-dimethyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1-ethyl-2-propenyl group, pentenyl group (for example, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, alkenyl groups such as 1-(1,1-dimethylethyl)ethenyl group, 1,3-dimethyl-1-butenyl group, hexenyl group (e.g., 1-hexenyl group, 5-hexenyl group), heptenyl group (e.g., 1-heptenyl group, 6-heptenyl group), octenyl group (e.g., 1-octenyl group, 7-octenyl group), nonenyl group (e.g., 1-nonenyl group, 8-nonenyl group), decenyl group (e.g., 1-decenyl group, 9-decenyl group), undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group, and icosenyl group;
Ethynyl group, propynyl group (e.g., 1-propynyl group, 2-propynyl group), butynyl group (e.g., 1-butynyl group, 2-butynyl group, 3-butynyl group), pentynyl group (e.g., 2-pentynyl group, 3-pentynyl group, 4-pentynyl group), 1-methyl-3-butynyl group, 1,1-dimethyl-2-propynyl group, hexynyl group (e.g., 2-hexynyl group, 5-hexynyl group), 1-ethyl-3-butynyl group, heptynyl group (e.g., 2-heptynyl group, 6 alkynyl groups such as 1-heptynyl group), 1-ethyl-3-pentynyl group, octynyl group (for example, 1-octynyl group, 2-octynyl group, 7-octynyl group), nonynyl group (for example, 2-nonynyl group, 8-nonynyl group), decynyl group (for example, 2-decynyl group, 9-decynyl group), undecynyl group, dodecynyl group, tridecynyl group, tetradecynyl group, pentadecynyl group, hexadecinyl group, heptadecynyl group, octadecynyl group, nonadecinyl group, and icosynyl group;
etc.

Examples of the unsaturated alicyclic hydrocarbon group represented by ^R21 include
cycloalkenyl groups such as a cyclohexenyl group (for example, a cyclohex-1-en-1-yl group, a cyclohex-2-en-1-yl group, a cyclohex-3-en-1-yl group), a cycloheptenyl group, and a cyclooctenyl group;
Unsaturated polycyclic hydrocarbon groups such as a norbornenyl group;
etc.

The unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R ²¹ may have a substituent. Examples of the substituent of the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R ²¹ include 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 ^a21 , -CO ₂ R ^a21 , -SR ^a21 , -SO ₂ R ^a21 , -SO ₃ R ^a21 , -SO ₂ NR ^a21 R ^a22 , -NR ^a21 R ^a22 , etc. Here, R ^a21 and R ^a22 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon group having 1 to 20 carbon atoms represented by R ^a21 and R ^a22 is the same as the hydrocarbon group having 1 to 20 carbon atoms represented by R ²² , R ²⁴ , and R ²⁵ described below.

Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms and used as a substituent of the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R ²¹ include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2-ethylphenyl group, a 3-ethylphenyl group, a 4-ethylphenyl group, a 2,3-dimethylphenyl group, a 2,4-dimethylphenyl group, a 2,5-dimethylphenyl group, a 2,6-dimethylphenyl group, a 3,4-dimethylphenyl group, a 3,5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, an m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, an m-tert-butylphenyl group, a p-tert-butylphenyl group, a 3,5-di(tert-butyl) ... Examples of such alkyl groups include di(tert-butyl)-4-methylphenyl group, 4-butylphenyl group, 4-pentylphenyl group, 2,6-bis(1-methylethyl)phenyl group, 2,4,6-tris(1-methylethyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-(1,1,3,3-tetramethylbutyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 6-methyl-2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecylphenyl group, perylenyl group, chrysenyl group, and pyrenyl group.

The aromatic hydrocarbon group preferably has 6 to 10 carbon atoms, more preferably 6 to 8 carbon atoms.

The aromatic hydrocarbon group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, -OR ^a21 , -CO ₂ R ^a21 , -SR ^a21 , -SO ₂ R ^a21 , -SO ₃ R ^a21 , -SO ₂ NR ^a21 R ^a22 , -NR ^a21 R ^a22 , and the like (wherein R ^a21 and R ^a22 are the same as above).

The heterocyclic group used as a substituent of the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by ^R21 may be a monocyclic or polycyclic ring, and is preferably a heterocyclic ring containing a heteroatom as a ring component. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

Heterocycles containing only nitrogen atoms as heteroatoms include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine, and piperazine; 5-membered unsaturated heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, and 1,2,4-triazole; 6-membered unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, and 1,3,5-triazine; condensed bicyclic heterocycles such as indazole, indoline, isoindoline, isoindoline-1,3-dione, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, and benzopiperidine; and condensed tricyclic heterocycles such as carbazole, acridine, and phenazine.

Heterocycles containing only oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, and 1,4-dioxane; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; lactone heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, and δ-valerolactone; 5-membered unsaturated heterocycles such as furan; 6-membered unsaturated heterocycles such as 2H-pyran and 4H-pyran; condensed bicyclic heterocycles such as 1-benzofuran, benzopyran, benzodioxole, chroman, and isochroman; and condensed tricyclic heterocycles such as xanthene and dibenzofuran.

Heterocycles containing only sulfur atoms as heteroatoms include 5-membered saturated heterocycles such as dithiolane; 6-membered saturated heterocycles such as thiane and 1,3-dithiane; 5-membered unsaturated heterocycles such as thiophene; 6-membered unsaturated heterocycles such as 4H-thiopyran; condensed bicyclic heterocycles such as benzothiopyrans, benzotetrahydrothiopyran, and benzothiophene; and condensed tricyclic heterocycles such as thianthrene and dibenzothiophene.

Heterocycles containing nitrogen and oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, and 2-piperidone; monocyclic unsaturated heterocycles such as oxazole and isoxazole; condensed bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; and condensed tricyclic heterocycles such as phenoxazine.

Heterocycles containing nitrogen and sulfur atoms as heteroatoms include monocyclic heterocycles such as thiazole; condensed bicyclic heterocycles such as benzothiazole; and condensed tricyclic heterocycles such as phenothiazine.

The number of carbon atoms in 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 ^a21 , -CO ₂ R ^a21 , -SR ^a21 , -SO ₂ R ^a21 , -SO ₃ R ^a21 , -SO ₂ NR ^a21 R ^a22 , -NR ^a21 R ^a22 and the like (wherein R ^a21 and R ^a22 are the same as above).

The bonding position of the heterocycle is the portion where any hydrogen atom contained in each ring has been removed.

Examples of the halogen atom used as a substituent of the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R ²¹ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

The aliphatic unsaturated hydrocarbon group represented by R ²³ is the same as the aliphatic unsaturated hydrocarbon group represented by R ²¹ .

The hydrocarbon groups represented by R ²² , R ²⁴ and R ²⁵ each have 1 to 20 carbon atoms, and preferably 1 to 15 carbon atoms.

The hydrocarbon groups having 1 to 20 carbon atoms represented by R ²² , R ²⁴ , and R ²⁵ may be aliphatic hydrocarbon groups and aromatic hydrocarbon groups, and the aliphatic hydrocarbon groups may be saturated or unsaturated and may be linear or cyclic (alicyclic hydrocarbon groups).

The saturated or unsaturated chain hydrocarbon group represented by R ²² , R ²⁴ , and R ²⁵ includes,
linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and icosyl groups;
Isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, 1,1,3,3-tetramethylbutyl group, 1-methylbutyl group, 1-ethylpropyl group, 3-methylbutyl group, neopentyl group, 1,1-dimethylpropyl group, 2-methylpentyl group, 3-ethylpentyl group, 1,3-dimethylbutyl group, 2-propylpentyl group, 1-ethyl-1,2-dimethylpropyl group, 1-methylpentyl group, 4-methylpentyl group, 4-methyl branched alkyl groups such as a 5-ethylhexyl group, a 2-ethylhexyl group, a 1-methylhexyl group, a 1-ethylpentyl group, a 1-propylbutyl group, a 3-ethylheptyl group, a 2,2-dimethylheptyl group, a 1-methylheptyl group, a 1-ethylhexyl group, a 1-propylpentyl group, a 1-methyloctyl group, a 1-ethylheptyl group, a 1-propylhexyl group, a 1-butylpentyl group, a 1-methylnonyl group, a 1-ethyloctyl group, a 1-propylheptyl group, and a 1-butylhexyl group;
Ethenyl group (vinyl group), propenyl group (for example, 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (for example, 1-butenyl group, 2-butenyl group, 3-butenyl group), 3-methyl-1-butenyl group, 1-methyl-1-butenyl group, 3-methyl-2-butenyl group, 1,3-butadienyl group, 3-methyl-1,2-butadienyl group, 1-(2-propenyl)ethenyl group, 1-(1-methylethenyl)ethenyl group, 1,1-dimethyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1-ethyl-2-propenyl group, pentenyl group (for example, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, alkenyl groups such as 1-(1,1-dimethylethyl)ethenyl group, 1,3-dimethyl-1-butenyl group, hexenyl group (e.g., 1-hexenyl group, 5-hexenyl group), heptenyl group (e.g., 1-heptenyl group, 6-heptenyl group), octenyl group (e.g., 1-octenyl group, 7-octenyl group), nonenyl group (e.g., 1-nonenyl group, 8-nonenyl group), decenyl group (e.g., 1-decenyl group, 9-decenyl group), undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group, and icosenyl group;
Ethynyl group, propynyl group (e.g., 1-propynyl group, 2-propynyl group), butynyl group (e.g., 1-butynyl group, 2-butynyl group, 3-butynyl group), pentynyl group (e.g., 2-pentynyl group, 3-pentynyl group, 4-pentynyl group), 1-methyl-3-butynyl group, 1,1-dimethyl-2-propynyl group, hexynyl group (e.g., 2-hexynyl group, 5-hexynyl group), 1-ethyl-3-butynyl group, heptynyl group (e.g., 2-heptynyl group, 6 alkynyl groups such as 1-heptynyl group), 1-ethyl-3-pentynyl group, octynyl group (for example, 1-octynyl group, 2-octynyl group, 7-octynyl group), nonynyl group (for example, 2-nonynyl group, 8-nonynyl group), decynyl group (for example, 2-decynyl group, 9-decynyl group), undecynyl group, dodecynyl group, tridecynyl group, tetradecynyl group, pentadecynyl group, hexadecinyl group, heptadecynyl group, octadecynyl group, nonadecinyl group, and icosynyl group;
etc.

The saturated chain hydrocarbon group (i.e., straight chain alkyl group, branched chain alkyl group) represented by R ²² , R ²⁴ , and R ²⁵ preferably has 1 to 10 carbon atoms, more preferably 1 to 7 carbon atoms, and even more preferably 1 to 5 carbon atoms.

The unsaturated chain hydrocarbon group (that is, alkenyl group, alkynyl group) represented by R ²² , R ²⁴ , and R ²⁵ preferably has 2-10 carbon atoms, more preferably 2-7 carbon atoms, and even more preferably 2-5 carbon atoms.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ²² , R ²⁴ , and R ²⁵ include a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 1,4-dimethylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 2,4-dimethylcyclohexyl group, a 2,5-dimethylcyclohexyl group, cycloalkyl groups such as a silyl group, a 2,6-dimethylcyclohexyl group, a 3,4-dimethylcyclohexyl group, a 3,5-dimethylcyclohexyl group, a 2,2-dimethylcyclohexyl group, a 3,3-dimethylcyclohexyl group, a 4,4-dimethylcyclohexyl group, a cyclooctyl group, a 2,4,6-trimethylcyclohexyl group, a 2,2,6,6-tetramethylcyclohexyl group, a 3,3,5,5-tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group;
cycloalkenyl groups such as a cyclohexenyl group (for example, a cyclohex-1-en-1-yl group, a cyclohex-2-en-1-yl group, a cyclohex-3-en-1-yl group), a cycloheptenyl group, and a cyclooctenyl group;
Saturated or unsaturated polycyclic hydrocarbon groups such as a norbornyl group, a norbornenyl group, an adamantyl group, or a bicyclo[2.2.2]octyl group;
etc.

The saturated or unsaturated alicyclic hydrocarbon group represented by R ²² , R ²⁴ and R ²⁵ preferably has 3 to 10 carbon atoms.

Examples of the aromatic hydrocarbon group represented by R ²² , R ²⁴ , and R ²⁵ include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2-ethylphenyl group, a 3-ethylphenyl group, a 4-ethylphenyl group, a 2,3-dimethylphenyl group, a 2,4-dimethylphenyl group, a 2,5-dimethylphenyl group, a 2,6-dimethylphenyl group, a 3,4-dimethylphenyl group, a 3,5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, an m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, an m-tert-butylphenyl group, a p-tert-butylphenyl group, a 3,5-di(tert-butyl)phenyl group, a 3,5-di(tert-butyl)-4-methylphenyl group, a ... aromatic hydrocarbon groups such as 1-butylphenyl group, 4-pentylphenyl group, 2,6-bis(1-methylethyl)phenyl group, 2,4,6-tris(1-methylethyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-(1,1,3,3-tetramethylbutyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 6-methyl-2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecylphenyl group, perylenyl group, chrysenyl group and pyrenyl group; and the like.

The aromatic hydrocarbon group represented by R ²² , R ²⁴ and R ²⁵ preferably has 6 to 20 carbon atoms, more preferably 6 to 10 carbon atoms, and even more preferably 6 to 8 carbon atoms.

The hydrocarbon group represented by R ²² , R ²⁴ , and R ²⁵ may be a group formed by combining the above-mentioned hydrocarbon groups (for example, a group formed by combining an aromatic hydrocarbon group with at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group),
aralkyl groups such as a benzyl group, a (2-methylphenyl)methyl group, a (3-methylphenyl)methyl group, a (4-methylphenyl)methyl group, a (2-ethylphenyl)methyl group, a (3-ethylphenyl)methyl group, a (4-ethylphenyl)methyl group, a (2-(tert-butyl)phenyl)methyl group, a (3-(tert-butyl)phenyl)methyl group, a (4-(tert-butyl)phenyl)methyl group, a (3,5-dimethylphenyl)methyl group, a 1-phenylethyl group, a 1-methyl-1-phenylethyl group, a 1,1-diphenylethyl group, a (1-naphthyl)methyl group and a (2-naphthyl)methyl group;
Arylalkenyl groups such as a 1-phenylethenyl group, a 2-phenylethenyl group (a phenylvinyl group), a 2,2-diphenylethenyl group, and a 2-phenyl-2-(1-naphthyl)ethenyl group;
Arylalkynyl groups such as a phenylethynyl group, a 3-phenyl-2-propynyl group, etc.;
A phenyl group having one or more phenyl groups bonded thereto, such as a biphenylyl group or a terphenylyl group;
A cyclohexylmethylphenyl group, a benzylphenyl group, a (dimethyl(phenyl)methyl)phenyl group;
etc.

These preferably have 7 to 18 carbon atoms, more preferably 7 to 15.

The groups represented by R ²² , R ²⁴ , and R ²⁵ may be groups formed by combining the above-mentioned hydrocarbon groups (for example, a group combining a chain hydrocarbon group and an alicyclic hydrocarbon group), and may be, for example, an alkyl group to which one or more alicyclic hydrocarbon groups are bonded, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a (2-methylcyclohexyl)methyl group, a cyclohexylethyl group, or an adamantylmethyl group.

These preferably have 4 to 15 carbon atoms, more preferably 4 to 10.

The hydrocarbon groups having 1 to 20 carbon atoms represented by R ²² , R ²⁴ and R ²⁵ may have a substituent.

Substituents for the hydrocarbon group having 1 to 20 carbon atoms represented by R ²² , R ²⁴ , and R ²⁵ include heterocyclic groups which may have a substituent, halogen atoms, a nitro group, a cyano group, -OR ^a21 , -CO ₂ R ^a21 , -SR ^a21 , -SO ₂ R ^a21 , -SO ₃ R ^a21 , -SO ₂ NR ^a21 R ^a22 , -NR ^a21 R ^a22 , and the like (wherein R ^a21 and R ^a22 are as defined above).

The heterocyclic group used as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R ²² , R ²⁴ , and R ²⁵ may be a monocyclic or polycyclic ring, and is preferably a heterocyclic ring containing a heteroatom as a ring component. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

Examples of the heterocyclic ring include the same heterocyclic groups as those used as the substituents of the unsaturated hydrocarbon groups having 2 to 20 carbon atoms represented by R ²¹ and R ²³ .

The number of carbon atoms in 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 ^a21 , -CO ₂ R ^a21 , -SR ^a21 , -SO ₂ R ^a21 , -SO ₃ R ^a21 , -SO ₂ NR ^a21 R ^a22 , -NR ^a21 R ^a22 and the like (wherein R ^a21 and R ^a22 are the same as above).

The bonding position of the heterocycle is the portion where any hydrogen atom contained in each ring has been removed.

Examples of halogen atoms used as substituents on the hydrocarbon groups having 1 to 20 carbon atoms represented by R ²² , R ²⁴ and R ²⁵ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

When R ²² is a single bond connecting Z ²² and R ²¹ , a part or all of R ²¹ is taken together with *-Z ²² -P(═O)-Z ²¹ -* (* represents a bond) to form a ring. In other words, when R ²² is a single bond connecting Z ²² and R ²¹ , a bond formed by sharing a pair of electrons between Z ²² and any carbon atom in the unsaturated hydrocarbon group having 2 to ²⁰ carbon atoms which may have a substituent represented by R 21 corresponds to the single bond represented by R ²² .

In the ring formed by part or all of R ²¹ taken together with *-Z ²² -P(═O)-Z ²¹ -* (* represents a bond), an unsaturated bond may be formed between carbon atoms that are members of the ring, an unsaturated bond may be formed between a carbon atom that is a member of the ring and a carbon atom that is not a member of the ring, or an unsaturated bond may be formed between carbon atoms that are not members of the ring.

Examples of the halogen atom represented by X ²¹ to X ³² include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. The halogen atom is preferably a fluorine atom.

The sulfamoyl group represented by X ²¹ to X ³² is represented by *-SO ₂ -NH ₂ (* represents a bond).

The sulfamoyl group represented by X ²¹ to X ³² may have a substituent. The substituent of the sulfamoyl group represented by X ²¹ to X ³² is the same as the substituent of the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R ²¹ and R ²³ , and specific examples thereof include 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 a21} , -CO ₂ R ^a21 , -SR ^a21 , -SO ₂ R a21 , -SO ₃ R ^a21 , -SO ₂ NR ^a21 R ^a22 , -NR ^a21 R ^a22 and the like (wherein R ^a21 and R ^a22 are the same as above).

-R ²⁴ represented by X ²¹ to X ²⁴ and -R ²⁵ represented by X ²⁵ to X ³² are preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a saturated chain hydrocarbon group having 1 to 20 carbon atoms, even more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, particularly preferably a branched alkyl group having 1 to 5 carbon atoms, and most preferably a tert-butyl group.

Specific examples of compound (II) and compound (III) include the compounds described in WO 2022/024926.

Quinophthalone compounds are compounds that have a quinophthalone skeleton in the molecule. Examples of quinophthalone compounds include C.I. Pigment Yellow 138, 231, and 233.

An isoindoline compound is a compound that has an isoindoline skeleton in the molecule. Examples of isoindoline compounds include C.I. Pigment Yellow 109, 139, and 185; and C.I. Pigment Orange 69.

An azo compound is a compound having an azo skeleton in the molecule. Examples of azo compounds include
C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 9, 10, 13, 14, 16, 17, 55, 61, 65, 73, 74, 75, 81, 83, 93, 94, 95, 97, 100, 104, 116, 120, 128, 150, 151, 152, 166, 167, 168, 169, 170, 174, 176, 180, 181, 182, 183, 188, 191, 184;
C.I. Pigment Orange 1, 5, 16, 17, 19, 22, 24, 34, 36, 38, 46, 62, 64, 65;
C.I. Pigment Red 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 48:1, 48:2, 48:3, 49, 49:1, 49:2, 50:1, 52:2, 53, 53:2, 53:3, 57, 57:2, 60, 63:1, 63:2, 64, 64:1, 112, 114, 147, 150, 151, 166, 170, 266, 175, 184, 188, 187, 188, 200, 210, 242, 243, 245, 247, 253, 258, 267, 268, 269, 273, 274;
C.I. Pigment Violet 50;
C.I. Pigment Blue 25;
C.I. Pigment Brown 1, 23
Examples include:

Diketopyrrolopyrrole compounds are compounds that have a diketopyrrolopyrrole skeleton in the molecule. Examples of diketopyrrolopyrrole compounds include C.I. Pigment Red 254, 255, 272, and 291.

A perylene compound is a compound that has a perylene skeleton in the molecule. Examples of perylene compounds include C.I. Pigment Red 123, 149, 178, 179, and 224; C.I. Pigment Violet 29; and C.I. Pigment Black 31 and 32.

Dioxazine compounds are compounds that have a dioxazine skeleton in the molecule. Examples of dioxazine compounds include V23 and V37.

An anthraquinone compound is a compound that has an anthraquinone skeleton in the molecule. Examples of anthraquinone compounds include Y147, Y193, R83, R177, and V5.

The content of colorant (A) is preferably 1 to 60 mass%, more preferably 5 to 50 mass%, and even more preferably 10 to 40 mass%, based on the total amount of solids in the colored curable composition. When the content of colorant (A) is within the above range, the desired spectrum and color density tend to be obtained more easily. In this specification, the "total amount of solids in the colored resin composition" means the total amount of components excluding the solvent from the colored resin composition. The total amount of solids in the colored resin composition and the content of each component relative to the total amount can be measured by known analytical means such as liquid chromatography and gas chromatography.

<Resin (B)>
The colored curable composition of the present embodiment contains a resin (B). The resin (B) is preferably an alkali-soluble resin. Examples of the alkali-soluble resin include the following resins [K1] to [K6].

Resin [K1]: a copolymer having a structural unit derived from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure and an ethylenically unsaturated bond having 2 to 4 carbon atoms; Resin [K2]: a copolymer having a structural unit derived from (a), a structural unit derived from (b), and a structural unit derived from a monomer (c) (however different from (a) and (b)) (hereinafter sometimes referred to as "(c)") copolymerizable with (a); Resin [K3]: a copolymer having a structural unit derived from (a) and a structural unit derived from (c); Resin [K4]: a copolymer having a structural unit obtained by adding (b) to a structural unit derived from (a), and a structural unit derived from (c). Resin [K5]: A copolymer having a structural unit derived from (c) and a structural unit derived from (a) added to a structural unit derived from (b) (may contain a structural unit derived from (b) to which (a) has not been added, but preferably does not contain such a structural unit).
Resin [K5']: A copolymer having a structural unit derived from (c) and a structural unit derived from (a) to which (b) has been added (although it may contain a structural unit derived from (a) to which (b) has not been added, it is preferable that it does not contain such a structural unit).
Resin [K6]: A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a polyvalent carboxylic acid and/or a carboxylic acid anhydride, and a structural unit derived from (c).

Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid;
Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid;
Bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;
Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;
Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate;
Examples of such an unsaturated acrylate include those containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid.

Of these, (a) is preferably acrylic acid, methacrylic acid, etc., in terms of copolymerization reactivity and the solubility of the resulting resin in an alkaline aqueous solution.

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

Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), etc.

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

(b1-1) includes glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000 (manufactured by Daicel Corporation)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400 (manufactured by Daicel Corporation)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100 (manufactured by Daicel Corporation)), 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate (3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-yl (meth)acrylate, etc.), 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate, ]decyloxyethyl (meth)acrylate, and the like.

(b2) is more preferably a monomer having an oxetanyl group and a (meth)acryloyloxy group. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and 3-ethyl-3-acryloyloxyethyloxetane.

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

(b) is preferably (b1) in that it can further increase the reliability of the heat resistance, chemical resistance, etc. of the resulting color filter. Furthermore, (b) is more preferably (b1-2) in that the storage stability of the colored curable composition is excellent.

Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate (commonly known in the art as "dicyclopentanyl (meth)acrylate" and sometimes referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 ^2,6 ](meth)acrylic acid esters such as decene-8-yl (meth)acrylate (commonly known in the technical field as "dicyclopentenyl (meth)acrylate"), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;
Hydroxy group-containing (meth)acrylic acid esters 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-methoxybicyclo[2.2.1]hept-2-ene, chloro[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene bicyclounsaturated compounds such as ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;
dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide;
Examples of the copolymer include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene.

Of these, (c) is preferably a (meth)acrylic acid ester.

In the resin [K1], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K1] is as follows:
Structural units derived from (a): 2 to 60 mol%
Structural units derived from (b): 40 to 98 mol%
It is preferred that
Structural units derived from (a): 10 to 50 mol%
Structural units derived from (b): 50 to 90 mol%
It is more preferable that:

When the ratio of the structural units of resin [K1] is within the above range, the colored curable composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the resulting color filter.

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

Specific examples of the method include a method in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, and the mixture is heated and kept warm while stirring. The polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, etc.). The solvent may be any solvent that dissolves each monomer, and for example, those exemplified as solvent (E) described below can be used.

The resulting copolymer may be used as it is in the solution after the reaction, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. In particular, by using the solvent contained in the colored curable composition of the present invention as the solvent during this polymerization, the solution after the reaction can be used as it is in the preparation of the colored curable composition of the present invention, and the manufacturing process of the colored curable composition of this embodiment can be simplified.

In the resin [K2], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K2] is as follows:
Structural units derived from (a): 2 to 45 mol%
Structural units derived from (b): 2 to 95 mol%
Structural units derived from (c): 1 to 65 mol%
It is preferred that
Structural units derived from (a): 5 to 40 mol%
Structural units derived from (b): 5 to 80 mol%
Structural units derived from (c): 5 to 60 mol%
It is more preferable that:

When the ratio of structural units of resin [K2] is within the above range, the colored curable composition tends to have excellent storage stability, developability when forming a colored pattern, and the resulting color filter tends to have excellent solvent resistance, heat resistance, and mechanical strength.

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

In the resin [K3], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K3] is as follows:
Structural units derived from (a): 2 to 60 mol%
Structural units derived from (c): 40 to 98 mol%
It is preferred that
Structural units derived from (a): 10 to 50 mol%
Structural units derived from (c): 50 to 90 mol%
It is more preferable that:

Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

Resin [K4] can be produced by obtaining a copolymer of (a) and (c) and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and/or carboxylic anhydride contained in (a).

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

Next, a part of the carboxylic acid and/or carboxylic anhydride derived from (a) in the copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air instead of nitrogen, and (b), a catalyst for the reaction of the carboxylic acid or carboxylic anhydride with the cyclic ether (e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.), a polymerization inhibitor (e.g., hydroquinone, methoquinone, etc.), etc. are placed in the flask, and the reaction is carried out, for example, at 60 to 130°C for 1 to 10 hours to produce the resin [K4].

The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). By using this range, the storage stability of the colored curable composition, the developability when forming a colored pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained colored pattern tend to be good. Since the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferably used for resin [K4], and (b1-1) is more preferable.

The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).

The reaction conditions such as the charging method, reaction temperature, and time can be appropriately adjusted taking into consideration the production equipment, the amount of heat generated by polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted taking into consideration the production equipment, the amount of heat generated by polymerization, etc.

In the first step, resin [K5] is produced by the same method as resin [K1] described above to obtain a copolymer of (b) and (c). As in the above, the resulting copolymer may be used as it is in the form of a solution after the reaction, or a concentrated or diluted solution, or it may be extracted as a solid (powder) by a method such as reprecipitation.

The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are, respectively,
Structural units derived from (b): 5 to 95 mol%
Structural units derived from (c): 5 to 95 mol%
It is preferred that
Structural units derived from (b): 10 to 90 mol%
Structural units derived from (c): 10 to 90 mol%
It is more preferable that:

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

In the resin [K5], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K5] is as follows:
Structural units derived from (b) ((a) is not added): 0 to 30 mol%
Structural units obtained by adding (a) to a structural unit derived from (b): 5 to 95 mol%
Structural units derived from (c): 5 to 95 mol%
It is preferred that
Structural units derived from (b) ((a) is not added): 0 to 10 mol %
Structural units obtained by adding (a) to a structural unit derived from (b): 15 to 90 mol%
Structural units derived from (c): 10 to 85 mol%
It is more preferable that
Structural units derived from (b) ((a) is not added): 0 to 5 mol%
Structural units obtained by adding (a) to a structural unit derived from (b): 20 to 80 mol%
Structural units derived from (c): 20 to 80 mol%
It is even more preferable that:

The total of the structural units derived from (b) (without (a) added), the structural units derived from (b) with (a) added, and the structural units derived from (c) may be, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and even more preferably 100 mol% of all the structural units constituting the resin [K5].

The amount of (a) used to react with the above copolymer is preferably 5 to 100 moles per 100 moles of (b). Because cyclic ethers are highly reactive and it is difficult for unreacted (b) to remain, it is preferable that (b) used in resin [K5] is (b1), and more preferably (b1-1).

Resin [K5'] can be manufactured by referring to the manufacturing method of resin [K4] described above.

In the resin [K5'], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K5'] is as follows:
Structural units derived from (a) (without (b) added): 0 to 30 mol %
Structural units obtained by adding (b) to a structural unit derived from (a): 5 to 95 mol%
Structural units derived from (c): 5 to 95 mol%
It is preferred that
Structural units derived from (a) (without (b) added): 0 to 10 mol %
Structural units obtained by adding (b) to a structural unit derived from (a): 15 to 90 mol%
Structural units derived from (c): 10 to 85 mol%
It is more preferable that
Structural units derived from (a) ((b) is not added): 0 to 5 mol %
Structural units obtained by adding (b) to a structural unit derived from (a): 20 to 80 mol%
Structural units derived from (c): 20 to 80 mol%
It is more preferable that:

The total of the structural units derived from (a) (without (b) added), the structural units derived from (a) with (b) added, and the structural units derived from (c) may be, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and even more preferably 100 mol% of all the structural units constituting the resin [K5'].

Examples of structural units derived from (a) (without the addition of (b)) include structural units derived from unsaturated monocarboxylic acids such as (meth)acrylic acid. Examples of structural units in which (b) is added to a structural unit derived from (a) include structural units in which a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is added to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. Examples of structural units derived from (c) include (meth)acrylic acid esters having linear or branched aliphatic saturated hydrocarbon groups, and (meth)acrylic acid esters having cyclic saturated hydrocarbon groups.

The amount of (b) used may be more than 80 moles and not more than 100 moles per 100 moles of (a).

Resin [K6] is a resin obtained by further reacting resin [K5] with a polycarboxylic acid and/or a carboxylic anhydride. The hydroxyl group generated by the reaction of the cyclic ether derived from (b) with the carboxylic acid or carboxylic anhydride derived from (a) is further reacted with a polycarboxylic acid and/or a carboxylic anhydride.

Examples of polycarboxylic acids include oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, and tricarbanilic acid. Examples of carboxylic anhydrides include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride. The amount of polycarboxylic acid and/or carboxylic anhydride used is preferably 0.05 to 1 mol, and more preferably 0.1 to 0.5 mol, per mol of (a).

As resin (B), a resin having a structural unit with an ethylenically unsaturated bond in the side chain (resin [K4], resin [K5], or resin [K6]) is preferred, and a resin having a structural unit containing a (meth)acryloyl group in the side chain is more preferred.

Examples of resins having structural units containing a (meth)acryloyl group in the side chain include resin [K4] which uses as (b) a monomer having a (meth)acryloyl group, such as glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3-methyl-3-methacryloyloxymethyloxetane, or tetrahydrofurfuryl acrylate; resin [K5] which uses as (a) a monomer having a (meth)acryloyl group, such as acrylic acid, methacrylic acid, or succinic acid mono[2-(meth)acryloyloxyethyl]; and resin [K6] which uses as (a) a monomer having a (meth)acryloyl group, such as acrylic acid, methacrylic acid, or succinic acid mono[2-(meth)acryloyloxyethyl]. As a resin having a structural unit containing a (meth)acryloyl group in the side chain, a resin [K6] using a monomer having a (meth)acryloyl group such as acrylic acid, methacrylic acid, or succinic acid mono[2-(meth)acryloyloxyethyl] as (a) is preferred.

The weight average molecular weight of resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 4,000 to 50,000, and even more preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed parts in the developer is good, and the resolution of the colored pattern tends to be improved.

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

The content of resin (B) is preferably 5 to 60 mass %, more preferably 10 to 55 mass %, and even more preferably 20 to 50 mass %, based on the total amount of solids in the colored curable composition. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and remaining film rate of the colored pattern tend to be improved.

<Polymerizable Compound (C)>
The colored curable composition of the present embodiment contains a polymerizable compound (C) and a polymerization initiator (D). The polymerizable compound (C) is a compound that can be polymerized by an active radical and/or an acid generated from the polymerization initiator (D). Examples of the polymerizable compound (C) include a compound having a polymerizable ethylenically unsaturated bond. The polymerizable compound (C) is preferably a (meth)acrylic acid ester compound.

The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, and tetrapentaerythritol nona(meth). Examples of the polymerizable compound (C) include tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene oxide modified pentaerythritol tetra(meth)acrylate, ethylene oxide modified dipentaerythritol hexa(meth)acrylate, propylene oxide modified pentaerythritol tetra(meth)acrylate, propylene oxide modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate, and caprolactone modified dipentaerythritol hexa(meth)acrylate. Among these, the polymerizable compound (C) is preferably trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, or unmodified or modified dipentaerythritol hexa(meth)acrylate.

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

The content of the polymerizable compound (C) is preferably 1 to 60 mass %, more preferably 5 to 50 mass %, and even more preferably 10 to 40 mass %, based on the total amount of solids in the colored curable composition. When the content of the polymerizable compound (C) is within the above range, the residual film rate during color pattern formation and the chemical resistance of the color filter tend to be improved.

<Polymerization initiator (D)>
The polymerization initiator (D) includes an O-acyloxime compound. The O-acyloxime compound is a compound that generates active radicals or the like by the action of light or heat and can initiate polymerization. The O-acyloxime compound is a compound having a partial structure represented by formula (d1). Hereinafter, * represents a bond.

Examples of O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and the like. As the O-acyloxime compound, commercially available products such as Irgacure (registered trademark, hereinafter the same) OXE01 (N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine), Irgacure OXE02 (N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine) (all manufactured by BASF), N-1919, and NCI-831 (manufactured by ADEKA Corporation) may be used.

Among these, the O-acyloxime compounds are N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, and N-benzoyloxy-1-( It is preferably at least one selected from the group consisting of N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and more preferably N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, or N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine. When such an O-acyloxime compound is used, a color filter with high brightness tends to be obtained.

The content of the O-acyloxime compound may be 50 to 100 mass%, 70 to 100 mass%, or 90 to 100 mass%, or may be 100 mass%, based on the total amount of the polymerization initiator (D).

The polymerization initiator (D) may contain, in addition to the O-acyloxime compound, other compounds that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization. Known polymerization initiators can be used as such compounds. Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, and biimidazole compounds.

The alkylphenone 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 compounds having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used as compounds having a partial structure represented by formula (d2).

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

From the viewpoint of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

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

Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available acylphosphine oxide compounds such as Irgacure 819 (manufactured by BASF) may also be used.

Examples of biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl) 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).

Further examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) (especially amines) described below.

Examples of polymerization initiators that generate acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate, as well as nitrobenzyl tosylates and benzoin tosylates.

The content of the other compounds may be 0 to 50 mass%, 0 to 30 mass%, or 0 to 10 mass%, based on the total amount of the polymerization initiator (D), or may be 0 mass%.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, per 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 increased and the exposure time tends to be shortened, so that improvement in productivity of the color filter can be expected.

<Polymerization Initiator Auxiliary Agent (D1)>
The polymerization initiation aid (D1) is a compound or sensitizer used to promote polymerization of a polymerizable compound. When the colored curable composition contains the polymerization initiation aid (D1), it is usually used in combination with the polymerization initiator (D).

Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, carboxylic acid compounds, etc.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone. As the amine compound, a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used. Of these, the amine compound is preferably 4,4'-bis(diethylamino)benzophenone.

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

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

Examples of carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc.

When these polymerization initiation aids (D1) are used, the content is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with even higher sensitivity, and the productivity of the color filter tends to improve.

<Composite oxide particles (E)>
The colored curable composition of the present embodiment contains composite oxide particles (E). The composite oxide particles (E) are oxide particles represented by the formula ABO ₃ (hereinafter, sometimes referred to as "ABO ₃ particles"). According to a colored curable composition containing ABO ₃ particles as the composite oxide particles (E), it is possible to form a cured coating film that is less likely to cause surface roughness during an ashing process. Although the reason for such an effect is not necessarily clear, _{it is believed that the addition of ABO 3 particles} protects the cured coating film from oxygen plasma and suppresses excessive vaporization and decomposition of the cured coating film.

In the formula, A represents a Group 2 metal atom. A is preferably beryllium, magnesium, calcium, strontium, or barium, more preferably calcium, strontium, or barium, and even more preferably barium.

In the formula, B represents a Group 4 metal atom. A is preferably titanium, zirconium, or hafnium, more preferably titanium.

Examples of the _ABO3 particles include _CaTiO3 , _SrTiO3 , BaTiO3, _{CaZrO3 , SrZrO3} , _BaZrO3 , _CaHfO3 , _SrHfO3 , _BaHfO3 , etc. Among these, the _ABO3 particles are preferably _BaTiO3 .

From the viewpoint of transparency, the average particle diameter of the composite oxide particles (E) ( _ABO3 particles) is preferably 0.1 μm (100 nm) or less, more preferably 0.05 μm (50 nm) or less. The average particle diameter of the composite oxide particles (E) ( _ABO3 particles) is usually 0.01 μm (10 nm) or more. In this specification, the average particle diameter means the particle diameter at an integrated value of 50% in the particle size distribution obtained by a laser diffraction/scattering method.

The content of the composite oxide particles (E) (ABO ₃ particles) may be 0.5 to 70 mass% based on the total amount of solids in the colored curable composition. When the content of the composite oxide particles (E) (ABO ₃ particles) is within the above range, the effects of the present invention tend to be more fully manifested. The content of the composite oxide particles (E) (ABO ₃ particles) is preferably 1 mass% or more, more preferably 3 mass% or more, even more preferably 5 mass% or more, particularly preferably 7 mass% or more, especially preferably 10 mass% or more, and most preferably 15 mass% or more, based on the total amount of solids in the colored curable composition, and is preferably 60 mass% or less, more preferably 55 mass% or less, even more preferably 50 mass% or less, particularly preferably 45 mass% or less, especially preferably 40 mass% or less, and most preferably 35 mass% or less.

<Solvent (F)>
The solvent (F) is not particularly limited, and a solvent normally used in the relevant field can be used. Examples thereof include 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 in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and gamma-butyrolactone.

Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methylanisole, etc.

Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxypropionate, Examples include ethyl oxy-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.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, isophorone, etc.

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

Aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene, etc.

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

Among these, the solvent (F) is preferably at least one selected from the group consisting of ether ester solvents and ether solvents, and more preferably propylene glycol monomethyl ether acetate or diethylene glycol ethyl methyl ether.

The content of the solvent (F) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored curable composition. In other words, the content of the solid content of the colored curable composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass, based on the total amount of the colored curable composition. When the content of the solvent (F) is within the above range, the flatness during application is good, and the color density is less likely to be insufficient when a color filter is formed, so that the display characteristics tend to be good.

When an ether ester solvent is used, the content of the ether ester solvent is preferably 10 to 100% by mass, more preferably 15 to 90% by mass, and even more preferably 17 to 80% by mass, based on the total amount of the solvent.

When an ether solvent is used, the content of the ether solvent is preferably 20 to 90% by mass, more preferably 30 to 85% by mass, and even more preferably 40 to 80% by mass, based on the total amount of the solvent.

<Leveling Agent (G)>
Examples of the leveling agent (G) include silicone surfactants, fluorine surfactants, silicone surfactants having fluorine atoms, etc. These may have a polymerizable group in the side chain.

Examples of silicone surfactants include surfactants having a siloxane bond in the molecule. Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (product names, manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).

Examples of fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule. Specific examples include Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by AGC Corporation (formerly Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemicals Research Institute, Ltd.).

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

The content of the leveling agent (G) is preferably 0.001 to 0.2 mass %, more preferably 0.002 to 0.1 mass %, and even more preferably 0.01 to 0.05 mass %, based on the total amount of the colored curable composition. When the content of the leveling agent (G) is within the above range, the flatness of the color filter can be improved.

<Other ingredients>
The colored curable composition of the present embodiment may contain additives known in the technical field, such as a dispersant (H), an ultraviolet absorber (I), a filler, another polymer compound, an adhesion promoter, an antioxidant, a light stabilizer, a chain transfer agent, etc. The colored curable composition of the present embodiment is preferably used for transmitting infrared rays.

[Method for producing colored curable composition]
The colored curable composition of the present embodiment can be prepared, for example, by mixing the colorant (A), the resin (B), the polymerizable compound (C), the polymerization initiator (D), the zirconia particles (E), and the solvent (F), as well as the polymerization initiator aid (D1), the leveling agent (G), and other components that are used as necessary.

The colorant (A) may be mixed with, for example, a solvent (F) to prepare a colorant dispersion containing the colorant (A) in advance, which may then be used to prepare the colored curable composition. The zirconia particles (E) may be mixed with, for example, a solvent (F) to prepare a zirconia particle dispersion containing the zirconia particles (E) in advance, which may then be used to prepare the colored curable composition.

After mixing the components, the colored curable composition is preferably filtered through a filter with a pore size of about 0.01 to 10 μm.

[Color filter and method for producing the same]
Examples of methods for producing a colored pattern from the colored curable composition of the present embodiment include a photolithography method, an inkjet method, and a printing method. Among these, the method for producing a colored pattern is preferably a photolithography method. The photolithography method is a method in which a colored curable composition is applied to a substrate, dried to form a coating film, and the coating film is exposed to light through a photomask and developed. In the photolithography method, a cured coating film, which is a cured product of the coating film, can be formed by not using a photomask during exposure and/or not developing. The colored pattern (patterned cured coating film) or cured coating film thus formed is the color filter of the present embodiment.

The thickness of the color filter to be produced is not particularly limited and can be adjusted appropriately depending on the purpose and application. The thickness of the color filter may be, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

Examples of substrates include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass with a silica-coated surface; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon substrates; and substrates having thin films of aluminum, silver, silver/copper/palladium alloys, etc. formed on the substrates. On these substrates, other color filters (colored patterns or cured coatings), resin films, transistors, circuits, etc. may be formed.

The formation of each color pixel by photolithography can be carried out using known or conventional equipment, conditions, etc. The formation of each color pixel by photolithography can be produced, for example, as follows.

First, the colored curable composition is applied onto a substrate, and then the composition is dried by heating (pre-baking) and/or drying under reduced pressure to remove volatile components such as solvents, resulting in a smooth coating film.

Examples of coating methods include spin coating, slit coating, and slit and spin coating. When drying by heating, the temperature is preferably 30 to 120°C, more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying under reduced pressure, it is preferably performed under a pressure of 50 to 150 Pa at a temperature range of 20 to 25°C.

The thickness of the coating film is not particularly limited and can be selected appropriately depending on the desired film thickness of the color filter.

The coating is then exposed through a photomask to form the desired colored pattern. The pattern of the photomask is not particularly limited, and any pattern appropriate for the intended use can be used.

The light source used for exposure is preferably a light source that generates light with a wavelength of 250 to 450 nm. The light source used for exposure may be, for example, one that cuts out light less than 350 nm using a filter that cuts out this wavelength range, or one that selectively extracts light around 436 nm, 408 nm, and 365 nm using a bandpass filter that extracts these wavelength ranges. Specific examples of light sources used for exposure include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

For exposure, it is preferable to use an exposure device such as a mask aligner or stepper, since it is possible to irradiate the entire exposure surface with parallel light uniformly and to perform accurate alignment between the photomask and the substrate on which the coating film is formed.

A colored pattern is formed on the substrate by contacting the exposed coating (i.e., the cured coating) with a developer and developing it. The unexposed parts of the cured coating are dissolved in the developer and removed by development. Examples of developers include aqueous solutions (aqueous developers) containing alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide. The concentration of the alkaline compound in these aqueous developers is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The developer may further contain a surfactant.

Examples of development methods include the puddle method, dipping method, and spray method. During development, the substrate may be tilted at any angle. After development, it is preferable to wash the resulting colored pattern with water.

It is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably 150 to 250°C, more preferably 160 to 235°C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

[Display device and solid-state imaging device]
The display device of the present embodiment includes a color filter which is a colored pattern, a cured coating film, etc. The solid-state imaging device of the present embodiment includes a color filter which is a colored pattern, a cured coating film, etc.

The colored curable composition of this embodiment can be used to produce, for example, a color filter. The color filter is useful as a film for use in displays such as liquid crystal displays, electroluminescent displays, and plasma displays; and solid-state imaging devices such as CCD and CMOS sensors.

The present invention will be explained in more detail below with reference to examples. However, the present invention is not limited to the following examples, and it is of course possible to carry out the invention with appropriate modifications within the scope of the above and below aims, all of which are included in the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

In the following examples, "room temperature" means 18-24°C.

In the following examples, the structures of the compounds were confirmed using a mass spectrometer (MALDI-TOF MS: JMS-S3000 manufactured by JEOL Ltd.) or a mass spectrometer (LC: "1200" manufactured by Agilent, MASS: "LC/MSD6130" manufactured by Agilent).

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions.
Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG2000HXL
Column temperature: 40°C
Solvent: tetrahydrofuran Flow rate: 1.0 mL/min Solids concentration of analytical sample: 0.001 to 0.01% by mass
Injection volume: 50 μL
Detector: RI
Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

The ratio of the weight average molecular weight and number average molecular weight (Mw/Mn) calculated in terms of polystyrene obtained above was taken as the degree of dispersion.

(Synthesis Example 1)
<Synthesis of Compound Represented by Formula (1) (Colorant A-1)>
According to the description of WO 2022/024926, a compound represented by the following formula (1) was synthesized.

<Identification of the compound represented by formula (1)>
(Mass spectrometry) Ionization mode = MALDI-TOF ^- : m/z = 740.3
Exact Mass: 740.2

(Synthesis Example 2)
<Synthesis of Compound Represented by Formula (3) (Colorant A-3)>
2,6-diphenylaniline was synthesized with reference to the method described in ARKIVOC, 2012, 9, 62-75. 4.00 parts of the compound represented by formula (3a), 9.69 parts of 2,6-diphenylaniline, 2.69 parts of zinc chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 24.0 parts of sulfolane (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 250 ° C., and stirred for 4 hours. After cooling the reaction solution to room temperature, 48.0 parts of 1N hydrochloric acid was added, and the resulting precipitate was obtained as a residue by suction filtration, and further washed with 24.0 parts of toluene, 18.0 parts of DMF, and 20.0 parts of DMF in sequence. The obtained residue was dried to obtain 5.18 parts of the compound represented by formula (3). The yield was 64%.

<Identification of the compound represented by formula (3)>
(Mass spectrometry) Ionization mode = ESI ⁺ : m/z = [M+H] ⁺ 823.3
Exact Mass: 823.3

(Synthesis Example 3)
<Synthesis of Resin B-1>
A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, 340 parts of PGMEA was added, and the mixture was heated to 80°C while stirring. Next, a mixed solution of 57 parts of acrylic acid, 54 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-yl acrylate (content ratio is 1:1 by molar ratio), 239 parts of benzyl methacrylate, and 73 parts of PGMEA was dropped over 5 hours. Meanwhile, a solution of 40 parts of polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 197 parts of PGMEA was dropped over 6 hours. After the dropwise addition of the polymerization initiator-containing solution was completed, the mixture was kept at 80°C for 3 hours and then cooled to room temperature to obtain a copolymer (Resin B-1) solution having a viscosity of 137 mPa·s measured with a Brookfield viscometer (23°C) and a solid content of 36.8 mass%. The polystyrene-equivalent weight average molecular weight of the produced copolymer was 1.0×10 ³ , the degree of dispersion was 1.97, and the solid content-equivalent acid value was 111 mg-KOH/g. Resin B-1 has the following structural units.

(Synthesis Example 4)
<Synthesis of Resin B-2>
276.8 parts of PGMEA was added to a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, and the mixture was stirred and heated to 120° C. while replacing with nitrogen. Next, 35.3 parts of t-butylperoxy-2-ethylhexanoate (polymerization initiator) was added to a monomer mixture consisting of 92.4 parts of 2-ethylhexyl acrylate, 184.9 parts of glycidyl methacrylate, and 12.3 parts of dicyclopentanyl methacrylate, and this was dropped into the flask from the dropping funnel over 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes at 120° C. to carry out a copolymerization reaction, and an addition copolymer was synthesized. Thereafter, the flask was replaced with air, and 93.7 parts of acrylic acid, 1.5 parts of triphenylphosphine (catalyst), and 0.8 parts of methoquinone (polymerization inhibitor) were added to the addition copolymer solution, and the reaction was continued for 10 hours at 110 ° C., and the epoxy group was cleaved by the reaction of the epoxy group derived from glycidyl methacrylate with acrylic acid, and a polymerizable unsaturated bond was introduced into the side chain of the addition copolymer. Next, 24.2 parts of succinic anhydride were added to the reaction system, and the reaction was continued for 1 hour at 110 ° C., and the hydroxyl group generated by the cleavage of the epoxy group was reacted with succinic anhydride to introduce a carboxyl group into the side chain, thereby obtaining a copolymer (resin B-2). Finally, 383.3 parts of PGMEA were added to the reaction solution, and a copolymer (resin B-2) solution with a solid content of 40% by mass was obtained. The weight average molecular weight of the resulting copolymer in terms of polystyrene was 6.3 × 10 ³ , and the acid value in terms of solid content was 34 mg-KOH / g.

(Synthesis Example 5)
<Preparation of Dispersion 1>
5.0 parts of the compound represented by formula (1), 2.9 parts of a dispersant (BYKLPN-6919 manufactured by BYK Corporation), 2.4 parts of resin B-1 (solid content equivalent), and 89.7 parts of PGMEA (including the solvent content of the resin B-1 solution) were mixed, 300 parts of 0.4 mm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU Corporation). Thereafter, the zirconia beads were removed by filtration to obtain dispersion 1.

(Synthesis Example 6)
<Preparation of Dispersion 2>
8.0 parts of the compound represented by formula (2) (colorant A-2, "Pink Base" manufactured by Taiyo Fine Chemical Co., Ltd.), 2.9 parts of a dispersant ("BYKLPN-6919" manufactured by BYK Corporation), 2.9 parts of resin B-1 (solid content equivalent), and 86.2 parts of PGMEA (including the solvent content of the resin B-1 solution) were mixed, 300 parts of 0.4 mm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU Corporation). Thereafter, the zirconia beads were removed by filtration to obtain dispersion 2.

(Synthesis Example 7)
<Preparation of Dispersion 3>
8.0 parts of the compound represented by formula (3), 2.9 parts of a dispersant (BYKLPN-6919 manufactured by BYK Corporation), 2.9 parts of resin B-1 (solid content equivalent), and 86.2 parts of PGMEA (including the solvent content of the resin B-1 solution) were mixed, 300 parts of 0.4 mm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU Corporation). Thereafter, the zirconia beads were removed by filtration to obtain dispersion 3.

(Synthesis Example 8)
<Preparation of _BaTiO3 Dispersion 1>
9.6 parts of barium titanate (BaTiO ₃ ) powder, 4.8 parts of a dispersant (BYK's "BYKLPN-6919"), and 85 parts of PGMEA were mixed, to which 300 parts of 0.4 mm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU's). The zirconia beads were then removed by filtration to obtain BaTiO ₃ Dispersion 1.

(Synthesis Example 9)
<Preparation of Dispersion 4>
12.1 parts of C.I. Pigment Red 254, 2.4 parts of a dispersant (BYK's "BYKLPN-6919"), 3.0 parts of resin B-1 (solid content equivalent), and 82.5 parts of PGMEA (including the solvent content of the resin B-1 solution) were mixed, 300 parts of 0.4 mm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 4.

(Synthesis Example 10)
<Preparation of Dispersion 5>
15.0 parts of C.I. Pigment Green 58, 3.0 parts of dispersant (BYK's "BYKLPN-6919"), 3.7 parts of resin B-1 (solid content equivalent), and 78.3 parts of PGMEA (including the solvent content of the resin B-1 solution) were mixed, 300 parts of 0.4 mm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 5.

(Synthesis Example 11)
<Preparation of Dispersion 6>
14.0 parts of C.I. Pigment Green 36, 2.8 parts of a dispersant (BYK's "BYKLPN-6919"), 2.8 parts of resin B-1 (solid content equivalent), and 80.4 parts of PGMEA (including the solvent content of the resin B-1 solution) were mixed, 300 parts of 0.4 mm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 6.

(Synthesis Example 12)
<Preparation of Dispersion 7>
12.0 parts of C.I. Pigment Blue 15:6, 4.4 parts of a dispersant (BYK's "BYKLPN-6919"), 4.8 parts of resin B-1 (solid content equivalent), and 78.8 parts of PGMEA (including the solvent content of the resin B-1 solution) were mixed, 300 parts of 0.4 mm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 7.

(Examples 1 to 10 and Comparative Example 1)
<Preparation of Colored Curable Composition>
The colored curable compositions of Examples 1 to 10 and Comparative Example 1 were prepared by mixing the components (unit: parts) shown in Tables 3 and 4.

(1) Dispersion 1 (Synthesis Example 5)
(Colorant A-1: Compound represented by formula (1) (Synthesis Example 1) 5.0 parts Resin B-1: Resin (Synthesis Example 3) (solid content equivalent) 2.4 parts Solvent F-1: PGMEA 89.7 parts (including the solvent content of the resin B-1 solution)
Dispersant H-1: Dispersant (BYKLPN-6919 manufactured by BYK) 2.9 parts
(2) Dispersion 2 (Synthesis Example 6)
(Colorant A-2: Compound represented by formula (2) (Pink Base manufactured by Taiyo Fine Chemical Co., Ltd.) 8.0 parts Resin B-1: Resin (Synthesis Example 3) (solid content equivalent) 2.9 parts Solvent F-1: PGMEA 86.2 parts (including the solvent content of the resin B-1 solution)
Dispersant H-1: Dispersant (BYKLPN-6919 manufactured by BYK) 2.9 parts
(3) Dispersion 3 (Synthesis Example 7)
(Colorant A-3: Compound represented by formula (3) (Synthesis Example 2) 8.0 parts Resin B-1: Resin (Synthesis Example 3) (solid content equivalent) 2.9 parts Solvent F-1: PGMEA 86.2 parts (including the solvent content of the resin B-1 solution)
Dispersant H-1: Dispersant (BYKLPN-6919 manufactured by BYK) 2.9 parts
(4) Dispersion 4 (Synthesis Example 9)
(Colorant A-4: C.I. Pigment Red 254 12.1 parts Resin B-1: Resin (Synthesis Example 3) (solid content equivalent) 3.0 parts Solvent F-1: PGMEA 82.5 parts (including the solvent content of the resin B-1 solution)
Dispersant H-1: Dispersant (BYK Corporation "BYKLPN-6919") 2.4 parts)
(5) Dispersion 5 (Synthesis Example 10)
(Colorant A-5: C.I. Pigment Green 58 15.0 parts Resin B-1: Resin (Synthesis Example 3) (solid content equivalent) 3.7 parts Solvent F-1: PGMEA 78.3 parts (including the solvent content of the resin B-1 solution)
Dispersant H-1: Dispersant (BYK Corporation "BYKLPN-6919") 3.0 parts)
(6) Dispersion 6 (Synthesis Example 11)
(Colorant A-6: C.I. Pigment Green 36 14.0 parts Resin B-1: Resin (Synthesis Example 3) (solid content equivalent) 2.8 parts Solvent F-1: PGMEA 80.4 parts (including the solvent content of the resin B-1 solution)
Dispersant H-1: Dispersant (BYK Corporation "BYKLPN-6919") 2.8 parts)
(7) Dispersion 7 (Synthesis Example 12)
(Colorant A-7: C.I. Pigment Blue 15:6 12.0 parts Resin B-1: Resin (Synthesis Example 3) (solid content equivalent) 4.8 parts Solvent F-1: PGMEA 78.8 parts (including the solvent content of the resin B-1 solution)
Dispersant H-1: Dispersant (BYK Corporation "BYKLPN-6919") 4.4 parts)
(8) _BaTiO3 Dispersion 1 (Synthesis Example 8)
( _BaTiO3 particles E-1: 9.6 parts _BaTiO3 particles, Dispersant H-1: 4.8 parts dispersant (BYKLPN-6919 manufactured by BYK), Solvent F-1: 85 parts PGMEA)
(9) Resin B-2: Resin (Synthesis Example 4) (solid content calculation)
(10) Polymerizable compound C-1: Ethylene oxide modified dipentaerythritol hexaacrylate (A-DPH12E manufactured by Shin-Nakamura Chemical Co., Ltd., number of ethylene oxide chains: 6, calculated as solid content)
(11) Polymerization initiator D-1: N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine (12) Solvent F-1: Propylene glycol monomethyl ether (PGME)
(13) Solvent F-2: Diacetone alcohol (DAA)
(14) Solvent F-3: PGMEA (Note that the values in Tables 3 and 4 include the solvent content of the resin B-2 solution.)
(15) Leveling agent G-1: Polyether modified silicone oil (Toray Silicone SH8400 manufactured by Dow Corning Toray Co., Ltd., solid content equivalent)
(16) Ultraviolet absorber I-1: DAINSORB-T0 manufactured by Daiwa Kasei Co., Ltd.

<Evaluation of Colored Pattern>
Preparation of colored pattern for evaluation Each of the colored curable compositions of Examples 1 to 10 and Comparative Example 1 was applied by spin coating onto a 4-inch silicon substrate so that the film thickness after post-baking was 0.8 μm, and then pre-baked at 80° C. for 2 minutes to obtain a coating film. After cooling, the substrate on which the coating film was formed was irradiated with light at an exposure dose of 300 mJ/cm ² (based on 365 nm) through a photomask using an exposure machine (NSR-1755i7A; manufactured by Nikon Corporation). The photomask used was one that formed a dot pattern of 5.0 μm square on the substrate. The coating film (cured coating film) after light irradiation was immersed and developed in an aqueous developer containing tetramethylammonium hydroxide at 23° C. for 30 seconds, washed with water, and post-baked at 230° C. for 10 minutes to obtain a plurality of silicon substrates having a colored pattern I after post-baking.

The silicon substrate having the colored pattern I was placed in a plasma dry cleaner (PDC510 manufactured by Yamato Scientific Co., Ltd.) and subjected to _O2 plasma treatment under the conditions of an _O2 flow rate of 90 cc (mL), an RF treatment time of 20 seconds, and an RF output of 300 W, to obtain a silicon substrate having a colored pattern II.

Evaluation of surface roughness of colored patterns for evaluation For the silicon substrate having colored pattern I or colored pattern II obtained above, the colored pattern formed at a magnification of 30,000 times was observed from above using an electron microscope (S-4100 manufactured by Hitachi High-Technologies Corporation), and an image with a width of 720 pixels and a height of 480 pixels was obtained. The obtained image was converted to grayscale, and the brightness distribution of each pixel was output as a histogram. The histogram of each image was approximated with a Gaussian function, and its half-width was evaluated. In the case of an image with small and uniform surface roughness, the half-width is narrow, and in principle, in the case of an image with large surface roughness, the half-width is wide. The evaluation was performed on a five-level scale from A to E based on the following criteria. The results are shown in Tables 5 and 6.
A: The half width was 65 or less.
B: The half width was more than 65 and 70 or less.
C: The half width was more than 70 and 80 or less.
D: The half width was more than 80 and 85 or less.
E: The half width exceeded 85.

As shown in Tables 5 and 6, the colored patterns of Examples 1 to 10, which contain the specified oxide particles as the composite oxide particles, had better surface conditions than the colored pattern of Comparative Example 1, which does not contain the specified oxide particles. These results confirm that the colored curable composition of the present invention is capable of forming a cured coating film that is less likely to develop surface roughness due to an ashing treatment.

Claims (3)

A colored curable composition comprising a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), composite oxide particles (E), and a solvent (F),
the polymerization initiator (D) contains an O-acyloxime compound,
The colored curable composition, wherein the composite oxide particles (E) are oxide particles represented by the formula _ABO3 (wherein A represents a Group 2 metal atom and B represents a Group 4 metal atom). A color filter formed from the colored curable composition according to claim 1. A display device including the color filter according to claim 2.