CN118244578A

CN118244578A - Colored curable composition, color filter and display device

Info

Publication number: CN118244578A
Application number: CN202311769733.7A
Authority: CN
Inventors: 中山智博; 荻田和宽
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2022-12-23
Filing date: 2023-12-21
Publication date: 2024-06-25

Abstract

The invention provides a colored curable composition capable of forming a cured coating film which is not easy to generate surface roughness due to ashing (Ashing) treatment. The colored curable composition contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), zirconia particles (E) and a solvent (F). The colorant (a) satisfies the following condition (i). The content of the colorant (A) is 1% by mass or more based on the total amount of solid components of the colored curable composition. The content of the zirconia particles (E) is 0.5 to 70% by mass based on the total amount of the solid components of the colored curable composition. In the condition (i), 0.1mg of the colorant (A) and 20g of propylene glycol monomethyl ether acetate are mixed at 25 ℃ for 2 hours, and the solid phase is separated by filtration, and the absorbance of the liquid phase obtained by the above is less than 2.0 at a maximum absorption wavelength in the visible light range of 380 to 780 nm.

Description

Colored curable composition, color filter and display device

Technical Field

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

Background

Color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma display devices, and solid-state imaging devices such as CCDs and CMOS sensors are manufactured from color curable compositions. As such a color curable composition, an ink for a color filter containing a colorant, a resin material, and the like is known (for example, patent document 1).

Prior art literature

Patent literature

Patent document 1 Japanese patent laid-open publication No. 2010-286692

Disclosure of Invention

In the film formation process of a color filter, the surface of a cured coating film may be subjected to ashing. The ashing treatment is a treatment of irradiating the surface of the cured coating film with oxygen plasma in a high energy state, and causing carbon atoms of unnecessary components in the cured coating film to react with oxygen atoms and gasify and decompose into CO ₂. However, cured coating films formed using conventional colored curable compositions may have rough surfaces due to ashing treatment.

The main object of the present invention is to provide a colored curable composition capable of forming a cured coating film which is less likely to cause surface roughness by ashing treatment.

The present invention provides the colored curable composition of [1], [2], the color filter of [3], and the display device of [4 ].

[1] A color curable composition comprising a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), zirconia particles (E) and a solvent (F), wherein the colorant (A) satisfies the following condition (i), the content of the colorant (A) is 1% by mass or more based on the total amount of the solid components of the color curable composition, and the content of the zirconia particles (E) is 0.5 to 70% by mass based on the total amount of the solid components of the color curable composition.

In the condition (i), 0.1mg of the colorant (A) and 20g of propylene glycol monomethyl ether acetate are mixed at 25 ℃ for 2 hours, and the solid phase is separated by filtration, and the absorbance of the liquid phase obtained by the above is less than 2.0 at a maximum absorption wavelength in the visible light range of 380 to 780 nm.

[2] The colored curable composition according to [1], wherein the colorant (A) contains a compound selected from the group consisting of xanthene compounds, phthalocyanine compounds, quinophthalone compounds, isoindoline compounds, azo compounds, diketopyrrolopyrrole compounds, perylene compounds, and diAt least 1 compound of the oxazine compound and the anthraquinone compound.

[3] A color filter formed from the colored curable composition of [1] or [2 ].

[4] A display device comprising the color filter of [3 ].

According to the present invention, there is provided a colored curable composition capable of forming a cured coating film which is less likely to cause surface roughness by ashing treatment. Further, according to the present invention, there are provided a color filter formed of such a colored curable composition and a display device including the color filter.

Detailed Description

Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments.

In the present specification, the numerical range indicated by "to" is used to indicate a range including numerical values described before and after "to" as a minimum value and a maximum value, respectively. In the numerical ranges described in stages in the present specification, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of the numerical range described in other stages. In the numerical ranges described in the present specification, the upper limit or the lower limit of the numerical range may be replaced with the values shown in the examples.

In the present specification, (meth) acrylate means acrylate or methacrylate corresponding thereto. Other similar expressions for (meth) acrylic acid, (meth) acryl, (meth) acrylic esters, and the like are also the same.

In the present specification, 1 kind of material may be used alone or 2 or more kinds may be used in combination, as long as the materials are not particularly described below, within the range that meets the conditions. When a plurality of substances corresponding to the respective components are present, the content of each component refers to the total amount of the plurality of 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), zirconia particles (E), and a solvent (F). The colored curable composition of the present embodiment may further contain a polymerization initiator (D1), a leveling agent (G), and the like.

< Colorant (A) >)

The color curable composition of the present embodiment contains a colorant (a). The colorant (a) satisfies the condition (i).

In the condition (i), 0.1mg of the colorant (A) and 20g of propylene glycol monomethyl ether acetate (hereinafter sometimes referred to as "PGMEA") are mixed at 25℃for 2 hours, and the solid phase is separated by filtration, whereby the absorbance of the liquid phase obtained is less than 2.0 at a maximum absorption wavelength in the visible light range of 380 to 780 nm.

The colorant satisfying the condition (i) may refer to a colorant having a low solubility in PGMEA at 25 ℃ and being substantially insoluble in PGMEA at 25 ℃. According to the studies by the present inventors, it has been found that the effect of the present invention can be more sufficiently obtained by the colorant (a) satisfying the above condition (i). When a plurality of compounds are contained as the colorant (a), the plurality of compounds are compounds whose solubility satisfies the above condition (i), respectively.

In the present specification, the absorbance at the maximum absorption wavelength of the condition (i) can be obtained by, for example, the following method. First, 0.1mg of colorant (A) and 20g of PGMEA were added to a sample bottle, and the mixture was stirred at 25℃for 2 hours. Then, the solid phase and the liquid phase were separated by filtration (PTFE membrane, pore size: 0.45 μm), and the absorption spectrum of the solution spectrum of the liquid phase was measured at 25℃using a spectrophotometer (for example, glass cuvette having a light path length of 10mm by Japan Spectroscopy "JASCO V-650") with PGMEA as a base line. In the obtained absorption spectrum, the absorbance was obtained from the maximum absorption wavelength in the visible light region between 380 and 780 nm.

The colorant (A) preferably contains a compound selected from the group consisting of xanthene compounds, phthalocyanine compounds, quinophthalone compounds, isoindoline compounds, azo compounds, diketopyrrolopyrrole compounds, perylene compounds, and diOxazine compound, anthraquinone compound, squaric acid/>At least 1 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, and a di/>, is more preferably containedAt least 1 compound of the oxazine compound and the anthraquinone compound is more preferably a xanthene compound or a phthalocyanine compound, and particularly preferably a phthalocyanine compound. These compounds or the compounds specifically described below have a tendency to easily satisfy the condition (i). The respective compounds may be dyes or pigments.

The xanthene compound is a compound having a xanthene skeleton in the molecule. As the xanthene compound, for example, acid red 52; c.i. pigment red 81, 81:1, 169, 173; c.i. pigment violet 1.

Examples of the xanthene compound include a compound represented by the formula (I) (hereinafter, sometimes referred to as "compound (I)"). The compound (I) may be a tautomer thereof.

In the formula (I), R ¹～R⁴ each independently represents 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, the-CH ₂ -contained in the saturated hydrocarbon group may be represented by-O-; -CO-or-NR ¹¹ -substitution.

R ⁵ represents －OH、－SO₃ ^－、－SO₃H、－SO₃ ^－Z⁺、－CO₂H、－CO₂ ^－Z⁺、－CO₂R⁸、－SO₃R⁸、 or-SO ₂NR⁹R¹⁰.

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, the plurality of R ⁵ may be the same or different.

A represents an integer of 0 or 1.

X represents a halogen atom.

Z ⁺ represents ⁺N(R¹¹)₄、Na⁺, or K ⁺, 4R ¹¹ may be identical 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, the-CH ₂ -contained in the saturated hydrocarbon group may be substituted with-O-, -CO-, -NH-or-NR ⁸ -, R ⁹ and R ¹⁰ may bond together with the adjacent nitrogen atom to form a three to ten membered heterocyclic ring.

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～R⁴ include straight-chain alkyl groups such as methyl, ethyl, propyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl and eicosyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl; alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and tricyclodecyl. The number of carbon atoms of the saturated hydrocarbon group is a number including carbon groups which also include substituents in the case of having a substituent. Examples of the substituent that the saturated hydrocarbon group may have include a halogen atom 、－OH、－OR⁸、－SO₃ ^－、－SO₃H、－SO₃ ^－Z⁺、－CO₂H、－CO₂R⁸、－SR⁸、－SO₂R⁸、－SO₃R⁸、－SO₂NR⁹R¹⁰、 OR-Si (OR ¹²)(OR¹³)(OR¹⁴).R¹²、R¹³ 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～R⁴ include phenyl, biphenyl, and triphenyl (ortho-terphenyl, meta-terphenyl, and para-terphenyl). Examples of the monovalent aromatic hydrocarbon group having a substituent include tolyl, xylyl, trimethylphenyl, propylphenyl, butylphenyl and the like. The number of carbon atoms of the aromatic hydrocarbon group is a number including carbon that also includes a substituent in the case of having a substituent. Examples of the substituent that the aromatic hydrocarbon group may have include a halogen atom 、－R⁸、－OH、－OR⁸、－SO₃ ^－、－SO₃H、－SO₃ ^－Z⁺、－CO₂H、－CO₂R⁸、－SR⁸、－SO₂R⁸、－SO₃R⁸、－SO₂NR⁹R¹⁰、 and-Si (OR ¹²)(OR¹³)(OR¹⁴).

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ⁸～R¹¹ include straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl and eicosyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl; alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and tricyclodecyl.

The monovalent saturated hydrocarbon groups of 1 to 20 carbon atoms in R ⁹ and R ¹⁰ may have a substituent. Examples of the substituent include a hydroxyl group and a halogen atom.

Examples of the monovalent saturated hydrocarbon group having 1 to 4 carbon atoms in R ¹²～R¹⁴ include straight-chain alkyl groups such as methyl, ethyl, propyl and butyl; branched alkyl groups such as isopropyl and isobutyl; alicyclic saturated hydrocarbon groups having 3 to 4 carbon atoms such as cyclopropyl.

Z ⁺ is N ⁺(R¹¹)₄、Na⁺ or K ⁺, preferably N ⁺(R¹¹)₄. Preferably, at least 2 of 4R ¹¹ in N ⁺(R¹¹)₄ are monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. The total number of carbon atoms of the 4R ¹¹ is preferably 20 to 80, more preferably 20 to 60.

Examples of-OR ⁸ include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, 2-ethylhexoxy and eicosoxy.

Examples of-CO ₂R⁸ include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, hexyloxycarbonyl and eicosyloxycarbonyl.

Examples of-SR ⁸ include methylthio, ethylthio, butylthio, hexylthio, decylthio and eicosylthio.

Examples of-SO ₂R⁸ include methylsulfonyl, ethylsulfonyl, butylsulfonyl, hexylsulfonyl, decylsulfonyl and eicosulfonyl.

Examples of-SO ₃R⁸ include methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, tert-butoxysulfonyl, hexyloxysulfonyl and eicosylsulfonyl.

Examples of the-SO ₂NR⁹R¹⁰ group include a sulfamoyl group; n-monosubstituted sulfamoyl groups such as N-methylsulfamoyl, N-ethylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N- (1, 1-dimethylpropyl) sulfamoyl, N- (2-methylbutyl) sulfamoyl, N-cyclopentylsulfamoyl, N-hexylsulfamoyl, N- (3, 3-dimethylbutyl) sulfamoyl, N- (1-methylhexyl) sulfamoyl, N-octylsulfamoyl, N- (2-ethylhexyl) sulfamoyl, N- (1, 2-tetramethylbutyl) sulfamoyl and the like; n, N-disubstituted sulfamoyl groups such as N, N-dimethyl sulfamoyl, N-ethyl methyl sulfamoyl, N-butyl ethyl sulfamoyl, N-bis (1-methylpropyl) sulfamoyl, N-heptyl methyl sulfamoyl, and the like.

Examples of-Si (OR ¹²)(OR¹³)(OR¹⁴) include trimethoxysilyl and triethoxysilyl.

R ⁵ is preferably －CO₂H、－CO₂ ^－Z⁺、－CO₂R⁸、－SO₃ ^－、－SO₃ ^－Z⁺、－SO₃H or SO ₂NHR⁹, more preferably SO ₃ ^－、－SO₃ ^－Z⁺、－SO₃ H or SO ₂NHR⁹.

M represents an integer of 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 R ⁶ and R ⁷ include the alkyl groups having 1 to 6 carbon atoms in the alkyl groups exemplified above. The alkyl group having 1 to 6 carbon atoms in R ⁶ and R ⁷ is preferably an alkyl group having 1 to 2 carbon atoms. R ⁶ and R ⁷ are more preferably hydrogen atoms.

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

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

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

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

TABLE 1

No.	R^ax1	R^ax2	R^ax3	R^ax4
					1	Ph	H	H	Ph
2	Ph	CH₃	CH₃	Ph
					3	Ph	CH₃CH₂	CH₃CH₂	Ph
4	o-Tolyl	H	H	o-Tolyl
					5	o-Tolyl	CH₃	CH₃	o-Tolyl
6	o-Tolyl	CH₃CH₂	CH₃CH₂	o-Tolyl
					7	m-Tolyl	H	H	m-Tolyl
8	m-Tolyl	CH₃	CH₃	m-Tolyl
					9	m-Tolyl	CH₃CH₂	CH₃CH₂	m-Tolyl
10	p-Tolyl	H	H	p-Tolyl
					11	p-Tolyl	CH₃	CH₃	p-Tolyl
12	p-Tolyl	CH₃CH₂	CH₃CH₂	p-Tolyl
					13	2，6-Xylyl	H	H	2，6-Xylyl
14	2，6-Xylyl	CH₃	CH₃	2，6-Xylyl
					15	2，6-Xylyl	CH₃CH₂	CH₃CH₂	2，6-Xylyl

TABLE 2

No.	R^ax1	R^ax2	R^ax3	R^ax4
					16	CH₃	CH₃	CH₃	PrTMS
17	CH₃CH₂	CH₃CH₂	CH₃	PrTMS
					18	CH₃CH₂	CH₃CH₂	CH₃CH₂	PrTMS
19	Ph	PrCOOH	PrCOOH	Ph
					20	o-Tolyl	PrCOOH	PrCOOH	o-Tolyl
21	m-Tolyl	PrCOOH	PrCOOH	m-Tolyl
					22	p-Tolyl	PrCOOH	PrCOOH	p-Tolyl
23	2，6-Xylyl	PrCOOH	PrCOOH	2，6-Xylyl
					24	MT1	H	H	MT1
25	MT1	CH₃	CH₃	MT1
					26	MT1	CH₃CH₂	CH₃CH₂	MT1
27	MT2	H	H	MT2
					28	MT2	CH₃	CH₃	MT2
29	MT2	CH₃CH₂	CH₃CH₂	MT2
					30	MT3	H	H	MT3
31	MT3	CH₃	CH₃	MT3
					32	MT3	CH₃CH₂	CH₃CH₂	MT3
33	2，4，6-Mesityl	H	H	2，4，6-Mesityl
					34	2，4，6-Mesityl	CH₃	CH₃	2，4，6-Mesityl
35	2，4，6-Mesityl	CH₃CH₂	CH₃CH₂	2，4，6-Mesityl
					36	m-terPh	H	H	m-terPh
37	m-terPh	CH₃	CH₃	m-terPh
					38	m-terPh	CH₃CH₂	CH₃CH₂	m-terPh

The symbols in the table represent the following groups (hereinafter, the bond sites are represented).

The phthalocyanine compound is a compound having a phthalocyanine skeleton in the molecule. Examples of the phthalocyanine compound include c.i. pigment green 7, 36, 58, 59, 62, 63; c.i. pigment blue 15:1, 15:2, 15:3, 15:4, 15:6, 16, 75.

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

In the formula (II) of the present invention,

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～X²⁴ each independently represents-R ²⁴、－OR²⁴、－SR²⁴, 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 represents an integer of 0 to 4.

In the formula (III) of the present invention,

R ²³ represents an aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent.

Z ²³ represents a single bond or an oxygen atom.

X ²⁵～X³² each independently represents-R ²⁵、－OR²⁵、－SR²⁵, 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 represents an integer of 0 to 4.

The unsaturated hydrocarbon group represented by R ²¹ is 2 to 20, preferably 2 to 10, more preferably 2 to 7, and even more preferably 2 to 5. The lower limit of the number of carbon atoms may be 3 or 4, and the upper limit of the number of carbon atoms may be 8.

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

The unsaturated chain hydrocarbon group represented by R ²¹ may be linear or branched, and specifically, examples thereof include: vinyl, propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylethenyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1-methyl-1-butenyl, 3-methyl-2-butenyl, 1, 3-butadienyl, 3-methyl-1, 2-butadienyl, 1- (2-propenyl) vinyl, 1- (1-methylethenyl) vinyl, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, pentenyl (e.g., 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl), 1- (1, 1-dimethylethyl) vinyl, 1, 3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), decenyl (e.g., 1-decenyl, 9-decenyl), undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosadienyl, and the like alkenyl groups; ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), butynyl (e.g., 1-butynyl, 2-butynyl, 3-butynyl), pentynyl (e.g., 2-pentynyl, 3-pentynyl, 4-pentynyl), 1-methyl-3-butynyl, 1-dimethyl-2-propynyl, hexynyl (e.g., 2-hexynyl, 5-hexynyl), 1-ethyl-3-butynyl, heptynyl (e.g., 2-heptynyl, 6-heptynyl), 1-ethyl-3-pentynyl, octynyl (e.g., 1-octynyl, 2-octynyl, 7-octynyl), nonynyl (e.g., 2-nonynyl, 8-nonynyl), decynyl (e.g., 2-decynyl, 9-decynyl), undecynyl, dodecynyl, tridecylynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecynyl, octadecenynyl, nonadecynyl, eicosynyl, and the like.

Examples of the unsaturated alicyclic hydrocarbon group represented by R ²¹ include cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl, cyclooctenyl, etc.; and unsaturated polycyclic hydrocarbon groups such as norbornene groups.

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、－CO₂R^a21、－SR^a21、－SO₂R^a21、－SO₃R^a21、－SO₂NR^a21R^a22、－NR^a21R^a22 and the like. Here, R ^a21 and R ^a22 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon groups having 1 to 20 carbon atoms represented by R ^a21 and R ^a22 are the same as the hydrocarbon groups having 1 to 20 carbon atoms represented by R ²²、R²⁴ and R ²⁵ described later.

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

The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 10, more preferably 6 to 8.

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、－CO₂R^a21、－SR^a21、－SO₂R^a21、－SO₃R^a21、－SO₂NR^a21R^a22、－NR^a21R^a22 and the like (wherein, R ^a21 and R ^a22 are the same as those described above).

The heterocyclic group used as a substituent of the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R ²¹ may be a single ring or may be a multiple ring, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.

Examples of the heterocyclic ring containing only a nitrogen atom as a hetero atom include monocyclic saturated heterocyclic rings such as aziridine, azetidine, pyrrolidine, piperidine, piperazine and the like; five-membered ring unsaturated heterocycles such as pyrrole, pyrazole, imidazole, 1,2, 3-triazole, 1,2, 4-triazole and the like; six-membered ring unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, 1,3, 5-triazine; indazole, indazoline, isoindoline-1, 3-dione, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine and other fused bicyclic heterocyclic ring systems; condensed tricyclic heterocycles such as carbazole, acridine and phenazine.

Examples of the heterocyclic ring containing only an oxygen atom as a hetero atom include an oxetane, tetrahydrofuran, tetrahydropyran, and 1, 3-di-nAlkane, 1, 4-di/>Saturated heterocyclic ring of single ring system such as alkane; bicyclic saturated heterocyclic rings such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone-based heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, and δ -valerolactone; five-membered ring system unsaturated heterocycle such as furan; six-membered ring system unsaturated heterocyclic ring such as 2H-pyran, 4H-pyran and the like; 1-benzofuran, benzopyran, benzodi/>Fused bicyclic heterocycles such as metallocene (Benzodioxole), chromane (Chromane) and heterochromane (Isochromane); condensed tricyclic heterocycles such as xanthene and dibenzofuran.

Examples of the heterocyclic ring containing only a sulfur atom as a hetero atom include five-membered ring saturated heterocyclic rings such as dithiolane; six-membered ring saturated heterocyclic rings such as thiocyclohexane and 1, 3-dithiane; five-membered ring system unsaturated heterocycles such as thiophene; unsaturated heterocyclic ring having six-membered ring system such as 4H-thiopyran; and fused bicyclic heterocycles such as benzothiopyran and benzothiophene; condensed tricyclic heterocycles such as thianthrene and dibenzothiophene.

Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom as hetero atoms include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone and 2-piperidone; Oxazole, iso/> Monocyclic unsaturated heterocycles such as oxazoles; benzo/>Azole, benzoiso/>Oxazole, benzo/>Oxazine, benzodi/>Condensed bicyclic heterocycles such as alkanes and benzimidazolines; pheno/>And condensed tricyclic heterocycles such as oxazine.

Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom as hetero atoms include monocyclic heterocyclic rings such as thiazole; fused bicyclic heterocycles such as benzothiazole; condensed tricyclic heterocycles such as phenothiazine and the like.

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

The heterocyclic group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group 、－OR^a21、－CO₂R^a21、－SR^a21、－SO₂R^a21、－SO₃R^a21、－SO₂NR^a21R^a22、－NR^a21R^a22 and the like (wherein R ^a21 and R ^a22 are the same as those described above).

The bonding position of the heterocycle is a portion after any hydrogen atom contained in each ring is detached.

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, an iodine atom and the like.

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、R²⁴ and R ²⁵ have 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms.

The hydrocarbon group having 1 to 20 carbon atoms represented by R ²²、R²⁴ and R ²⁵ may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, or may be a chain or cyclic (alicyclic hydrocarbon group).

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ²²、R²⁴ and R ²⁵ include 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 eicosyl; Isopropyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3-dimethylbutyl, 1, 3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1-dimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1, 3-dimethylbutyl, 1-methylbutyl 2-propylpentyl, 1-ethyl-1, 2-dimethylpropyl, 1-methylpentyl, 4-methylhexyl, 5-methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2-dimethylheptyl, Branched alkyl groups such as 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl, and 1-butylhexyl; Vinyl, propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylethenyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1-methyl-1-butenyl, 3-methyl-2-butenyl, 1, 3-butadienyl, 3-methyl-1, 2-butadienyl, 1- (2-propenyl) vinyl, 1- (1-methylethenyl) vinyl, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, pentenyl (e.g., 1-pentenyl), 2-pentenyl, 3-pentenyl, 4-pentenyl), 1- (1, 1-dimethylethyl) vinyl, 1, 3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), decenyl (e.g., 1-decenyl, 9-decenyl), undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, Alkenyl groups such as eicosapentaenoic acid group; Ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), butynyl (e.g., 1-butynyl, 2-butynyl, 3-butynyl), pentynyl (e.g., 2-pentynyl, 3-pentynyl, 4-pentynyl), 1-methyl-3-butynyl, 1-dimethyl-2-propynyl, hexynyl (e.g., 2-hexynyl, 5-hexynyl), 1-ethyl-3-butynyl, heptynyl (e.g., 2-heptynyl, 6-heptynyl), 1-ethyl-3-pentynyl, octynyl (e.g., 1-octynyl, 2-octynyl, 7-octynyl), nonynyl (e.g., 2-nonynyl), 8-nonynyl), decynyl (e.g., 2-decynyl, 9-decynyl), undecynyl, dodecynyl, tridecylynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecynyl, octadecyl, nonadecynyl, eicosynyl, and the like.

The number of carbon atoms of the saturated chain hydrocarbon group (i.e., linear alkyl group or branched alkyl group) represented by R ²²、R²⁴ and R ²⁵ is preferably 1 to 10, more preferably 1 to 7, and still more preferably 1 to 5.

The number of carbon atoms of the unsaturated chain hydrocarbon group (i.e., alkenyl group, alkynyl group) represented by R ²²、R²⁴ and R ²⁵ is preferably 2 to 10, more preferably 2 to 7, still more preferably 2 to 5.

As the saturated or unsaturated alicyclic hydrocarbon groups represented by R ²²、R²⁴ and R ²⁵, examples thereof include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl cycloalkyl groups such as 2,4, 6-trimethylcyclohexyl, 2, 6-tetramethylcyclohexyl, 3, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl, and 4-cyclohexylcyclohexyl; cyclohexenyl (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl, cyclooctenyl, and the like cycloalkenyl; saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, adamantyl, and bicyclo [2.2.2] octyl.

The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group represented by R ²²、R²⁴ and R ²⁵ is preferably 3 to 10.

As the aromatic hydrocarbon groups represented by R ²²、R²⁴ and R ²⁵, examples thereof include phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2, 3-dimethylphenyl, 2, 4-dimethylphenyl, 2, 5-dimethylphenyl, 2, 6-dimethylphenyl, 3, 4-dimethylphenyl, 3, 5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 3, 5-di (tert-butylphenyl), 3, 5-di (tert-butyl) -4-methylphenyl 4-butylphenyl, 4-pentylphenyl, 2, 6-bis (1-methylethyl) phenyl, 2,4, 6-tris (1-methylethyl) phenyl, 4-cyclohexylphenyl, 2,4, 6-trimethylphenyl, 4-octylphenyl, 4- (1, 3-tetramethylbutyl) phenyl, 1-naphthyl, 2-naphthyl, 6-methyl-2-naphthyl, 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, perylenyl,Aromatic hydrocarbon groups such as a radical and a pyrenyl group.

The number of carbon atoms of the aromatic hydrocarbon group represented by R ²²、R²⁴ and R ²⁵ is preferably 6 to 20, more preferably 6 to 10, and still more preferably 6 to 8.

The hydrocarbon group represented by R ²²、R²⁴ and R ²⁵ may be a group obtained by combining the above-exemplified hydrocarbon groups (for example, a group obtained by combining an aromatic hydrocarbon group with at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl group, (2-methylphenyl) methyl group, (3-methylphenyl) methyl group, (4-methylphenyl) methyl group, (2-ethylphenyl) methyl group, (3-ethylphenyl) methyl group, (4-ethylphenyl) methyl group, (2- (tert-butyl) phenyl) methyl group, (3- (tert-butyl) phenyl) methyl group, (4- (tert-butyl) phenyl) methyl group, (3, 5-dimethylphenyl) methyl group, 1-phenylethyl group, 1-methyl-1-phenylethyl group, 1-diphenylethyl group, (1-naphthyl) methyl group and (2-naphthyl) methyl group; arylalkenyl groups such as 1-phenylvinyl, 2-phenylvinyl (phenylvinyl), 2-diphenylvinyl, and 2-phenyl-2- (1-naphthyl) vinyl; arylalkynyl such as phenylethynyl and 3-phenyl-2-propynyl; phenyl in which 1 or more phenyl groups such as biphenyl and terphenyl are bonded; cyclohexylmethylphenyl, benzyl phenyl, (dimethyl (phenyl) methyl) phenyl, and the like.

The number of carbon atoms of these is preferably 7 to 18, more preferably 7 to 15.

The group represented by R ²²、R²⁴ and R ²⁵ may be a group obtained by combining the above-exemplified hydrocarbon groups (for example, a group obtained by combining a chain hydrocarbon group with an alicyclic hydrocarbon group), and may be, for example, an alkyl group having 1 or more alicyclic hydrocarbon groups bonded thereto, such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl) methyl, cyclohexylethyl, adamantylmethyl, or the like.

The number of carbon atoms of these is preferably 4 to 15, more preferably 4 to 10.

The hydrocarbon group having 1 to 20 carbon atoms represented by R ²²、R²⁴ and R ²⁵ may have a substituent.

Examples of the substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R ²²、R²⁴ and R ²⁵ include a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group 、－OR^a21、－CO₂R^a21、－SR^a21、－SO₂R^a21、－SO₃R^a21、－SO₂NR^a21R^a22、－NR^a21R^a22 and the like (wherein R ^a21 and R ^a22 are the same as described above).

The heterocyclic group used as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R ²²、R²⁴ and R ²⁵ may be a single ring or a polycyclic ring, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.

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

Examples of the halogen atom used as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R ²²、R²⁴ and R ²⁵ include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.

When R ²² is a single bond joining Z ²² and R ²¹, part or all of R ²¹ together with-Z ²²－P(＝O)－Z²¹ — (representing the bonding site) form a ring. That is, when R ²² is a single bond connecting Z ²² and R ²¹, a bond obtained 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 and is represented by R ²¹ corresponds to a single bond represented by R ²².

In the ring in which part or all of R ²¹ forms together with —z ²²－P(＝O)－Z²¹ — (representing a bonding site), an unsaturated bond may be formed between carbon atoms that are constituent atoms of the ring and carbon atoms other than constituent atoms of the ring, or an unsaturated bond may be formed between carbon atoms other than constituent atoms of the ring.

Examples of the halogen atom represented by X ²¹～X³² 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～X³² is represented by-SO ₂－NH₂ (the bond site is represented).

The sulfamoyl group represented by X ²¹～X³² may have a substituent. The substituent of the sulfamoyl group represented by X ²¹～X³² 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 specifically, 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、－CO₂R^a21、－SR^a21、－SO₂R^a21、－SO₃R^a21、－SO₂NR^a21R^a22、－NR^a21R^a22, and the like are exemplified (wherein R ^a21 and R ^a22 are the same as those described above).

The groups-R ²⁴ and-R ²⁵ represented by X ²¹～X²⁴ and X ²⁵～X³² are preferably aliphatic hydrocarbon groups having 1 to 20 carbon atoms, more preferably saturated chain hydrocarbon groups having 1 to 20 carbon atoms, still more preferably saturated chain hydrocarbon groups having 1 to 10 carbon atoms, particularly preferably branched alkyl groups having 1 to 5 carbon atoms, and most preferably tert-butyl groups.

Specific examples of the compound (II) and the compound (III) include, for example, those described in International publication No. 2022/024926.

Quinophthalone compounds are compounds having a quinophthalone skeleton in the molecule. Examples of quinophthalone compounds include c.i. pigment yellow 138, 231, and 233.

The isoindoline compound is a compound having an isoindoline skeleton in the molecule. Examples of the isoindoline compound include c.i. pigment yellow 109, 139, 185; c.i. pigment orange 69.

The azo compound is a compound having an azo skeleton in the molecule. Examples of the azo compound 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.

The diketopyrrolopyrrole compound is a compound having a diketopyrrolopyrrole skeleton in the molecule. Examples of the diketopyrrolopyrrole compound include c.i. pigment red 254, 255, 272, 291.

Perylene compounds are compounds having a perylene skeleton in the molecule. Examples of perylene compounds include c.i. pigment red 123, 149, 178, 179, 224; c.i. pigment violet 29; c.i. pigment black 31, 32.

Two (II)The oxazine compound has two/>The oxazine skeleton is a compound. As two/>Examples of the oxazine compound include V23 and V37.

Anthraquinone compounds are compounds having an anthraquinone backbone in the molecule. Examples of the anthraquinone compound include Y147, Y193, R83, R177 and V5.

The content of the colorant (A) is 1% by mass or more based on the total amount of solid components of the colored curable composition. The content of the colorant (a) is preferably 3% by mass or more, more preferably 5% by mass or more, further preferably 10% by mass or more, preferably 60% by mass or less, more preferably 50% by mass or less, further preferably 40% by mass or less, based on the total amount of the solid components of the colored curable composition. When the content of the colorant (a) is within the above range, there is a tendency that a desired spectrum of light and color density are more easily obtained. In the present specification, the term "total amount of solid components of the curable color composition" refers to the total amount of components obtained by removing the solvent from the curable color composition. The total amount of the solid components of the color curable composition and the content of each component relative to the total amount can be measured by a known analytical method such as liquid chromatography or gas chromatography.

< Resin (B) >)

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

The resin [ K1] is a copolymer having a structural unit derived from at least 1 monomer (a) (hereinafter sometimes referred to as "(a)") selected from unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and a structural unit derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenic unsaturated bond

The 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) copolymerizable with (a) (wherein the structural unit is different from (a) and (b) (hereinafter sometimes referred to as "(c)")

Resin [ K3]: copolymer having structural unit derived from (a) and structural unit derived from (c)

Resin [ K4]: copolymer having structural unit (b) added to structural unit (a) and structural unit (c)

The resin [ K5] is a copolymer having a structural unit in which (a) is added to a structural unit derived from (b) and a structural unit derived from (c) (the copolymer may contain a structural unit derived from (b) to which (a) is not added, but preferably does not contain)

Resin [ K5' ] copolymer having structural unit (b) added to structural unit (a) and structural unit (c) (structural unit (a) to which (b) is not added may be contained, but preferably not contained.)

The resin [ K6] is a copolymer comprising a structural unit obtained by adding a structural unit derived from (b) to (a) and further adding a polycarboxylic acid and/or carboxylic anhydride, and a structural unit derived from (c)

Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, ortho-, meta-, and para-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-cyclohexene dicarboxylic acid;

Carboxyl group-containing bicyclic unsaturated compounds such as methyl-5-norbornene-2, 3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5, 6-dicarboxyibicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;

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

unsaturated mono [ (meth) acryloyloxyalkyl ] esters of dibasic or higher polycarboxylic acids such as mono [2- (meth) acryloyloxyethyl ] succinate and mono [2- (meth) acryloyloxyethyl ] phthalate;

unsaturated acrylates containing a hydroxyl group and a carboxyl group in the same molecule, such as α - (hydroxymethyl) acrylic acid.

Among them, (a) is preferably acrylic acid, methacrylic acid or the like in view of copolymerization reactivity and solubility of the obtained resin in an aqueous alkali solution.

(B) For example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least 1 selected from an oxetane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond may be used. (b) Monomers having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group are preferable.

Examples of (b) include a monomer (b 1) having an oxetanyl group and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b 1)"), a monomer (b 2) having an oxetanyl group and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b 2)"), a monomer (b 3) having a tetrahydrofuranyl group and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b 3)"), and the like.

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

Examples of (b 1-1) include glycidyl (meth) acrylate, β -methyl glycidyl (meth) acrylate, β -ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α -methyl-o-vinylbenzyl glycidyl ether, α -methyl-m-vinylbenzyl glycidyl ether, α -methyl-p-vinylbenzyl glycidyl ether, 2, 3-bis (glycidoxymethyl) styrene, 2, 4-bis (glycidoxymethyl) styrene, 2, 5-bis (glycidoxymethyl) styrene, 2, 6-bis (glycidoxymethyl) styrene, 2,3, 4-tris (glycidoxymethyl) styrene, 2,3, 5-tris (glycidoxymethyl) styrene, 2,3, 6-tris (glycidoxymethyl) styrene, 3,4, 5-tris (glycidoxymethyl) styrene, 2, 4-tris (glycidoxymethyl) styrene, and the like.

Examples of the (b 1-2) include vinylcyclohexene monooxide, 1, 2-epoxy-4-vinylcyclohexane (for example, celloxide 2000 (manufactured by Daicel)), 3, 4-epoxycyclohexylmethyl (meth) acrylate (for example, cyclomer A400 (manufactured by Daicel)), 3, 4-epoxycyclohexylmethyl (meth) acrylate (for example, cyclomer M100 (manufactured by Daicel)), 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, and 3, 4-epoxytricyclo [5.2.1.0 ^2,6 ] decyloxyethyl (meth) acrylate.

(B2) More preferred are monomers having oxetanyl and (meth) acryloyloxy groups. Examples of (b 2) include 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-ethyl-3-acryloyloxymethyl oxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, and 3-ethyl-3-acryloyloxyethyl oxetane.

As (b 3), monomers having a tetrahydrofuranyl group and a (meth) acryloyloxy group are more preferable. Specific examples of (b 3) include tetrahydrofurfuryl acrylate (for example, viscoat V#150, manufactured by Osaka organic chemical industry Co., ltd.), and tetrahydrofurfuryl methacrylate.

As (b), in view of enabling higher reliability such as heat resistance and chemical resistance of the obtained color filter, it is preferable to use (b 1). Further, from the viewpoint of excellent storage stability of the color curable composition, it is more preferable that (b 1-2).

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 (in this technical field, as a conventional name, tricyclopentyl (meth) acrylate ". In addition, tricyclodecyl (meth) acrylate"), tricyclo [5.2.1.0 ] ^2,6 ] decen-8-yl (in this technical field, as a conventional name, tricyclopentenyl (meth) acrylate "), (dicyclopentenyl) acrylate, (meth) dioxolyl ethyl (meth) acrylate, (meth) isopropyl (meth) acrylate, (phenyl) acrylate, (meth) allyl (meth) acrylate, and the like).

Hydroxy group-containing (meth) acrylates 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-methylcyclo [2.2.1] hept-2-ene, 5-ethylcyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2' -hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5, 6-dihydroxybicyclo [2.2.1] hept-2-ene, 5, 6-di (hydroxymethyl) bicyclo [2.2.1] hept-2-ene, 5, 6-dimethoxybicyclo [ 2.1] hept-2-ene, 5, 6-diethoxy bicyclo [ 2.1] hept-2-ene, 5-diethoxy [ 2.1] bicyclohexa-2-ene, 5-hydroxy-2.1 ] hept-2-ene, 5-hydroxy-2.1-carbonyl, 5-di (hydroxymethyl) bicyclo [ 2.2.2.1 ] hept-2-ene, 5, 6-di (2.1 ] bicyclooxy-carbonyl-2.1 ] bicyclohept-2-ene, 5-bicyclooxy [ 2.1] hept-2-ene;

Dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N- (9-acridinyl) maleimide;

Styrene, alpha-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1, 3-butadiene, isoprene, 2, 3-dimethyl-1, 3-butadiene, and the like.

Among them, (c) is preferably (meth) acrylic acid esters.

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

When the ratio of the structural units of the resin [ K1] is in the above range, the storage stability of the colored curable composition, the developability upon forming a colored pattern, and the solvent resistance of the obtained color filter tend to be excellent.

The resin [ K1] can be produced by, for example, a method described in the literature "Experimental method for polymer synthesis" (Dain Kagaku Kogyo, ltd., chemical Co., ltd., 1 st edition, 1 st printing, release 3 months, 1972, 1 st day) and a cited literature described in the literature as references.

Specifically, a method is exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are charged into a reaction vessel, and a deoxidized atmosphere is produced by substituting oxygen with nitrogen, for example, and heating and heat preservation are performed while stirring. The polymerization initiator, solvent, and the like used herein are not particularly limited, and those commonly used in the art can be used. Examples of the polymerization initiator include azo compounds (e.g., 2 '-azobisisobutyronitrile and 2,2' -azobis (2, 4-dimethylvaleronitrile)), and organic peroxides (e.g., benzoyl peroxide and t-butyl peroxy-2-ethylhexanoate). The solvent may be any solvent as long as it dissolves the monomers, and for example, a solvent exemplified in the solvent (E) described later can be used.

The copolymer obtained may be used as it is, a concentrated or diluted solution, or a solid (powder) extracted by a method such as reprecipitation. In particular, since the solvent contained in the colored curable composition of the present invention is used as a solvent in the polymerization, the solution after the reaction can be directly used for preparing the colored curable composition of the present invention, and thus the process for producing the colored curable composition of the present embodiment can be simplified.

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

When the ratio of the structural units of the resin [ K2] is in the above range, the storage stability of the colored curable composition, the developability upon forming a colored pattern, and the solvent resistance, heat resistance and mechanical strength of the obtained color filter tend to be excellent.

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

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

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

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

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

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

(B) The amount of (a) to be used is preferably 5 to 80 moles, more preferably 10 to 75 moles, based on 100 moles of (a). In this range, there is a tendency that the balance of the storage stability of the colored curable composition, the developability at the time of forming a pattern, and the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern becomes good. The (b) used in the resin [ K4] is preferably (b 1), more preferably (b 1-1), from the viewpoint of high reactivity of the cyclic ether and less tendency of unreacted (b) to remain.

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

The reaction conditions such as the charging method, the reaction temperature, and the time may be appropriately adjusted in consideration of the production equipment, the amount of heat generated by polymerization, and the like. The method of charging and the reaction temperature may be appropriately adjusted in consideration of the production equipment, the amount of heat generated by polymerization, and the like, similarly to the polymerization conditions.

As the first stage, the copolymer of (b) and (c) was obtained in the same manner as the above-mentioned method for producing the resin [ K1 ]. As in the above, the copolymer obtained may be used as it is, or may be concentrated or diluted, or may be taken out as a solid (powder) by a method such as reprecipitation.

The ratio of the structural units derived from (b) and (c) is preferably 5 to 95 mol% of the structural units derived from (b) and 5 to 95 mol% of the structural units derived from (c), more preferably 10 to 90 mol% of the structural units derived from (b) and 10 to 90 mol% of the structural units derived from (c), respectively, based on the total mole number of all the structural units constituting the copolymer.

Further, the carboxylic acid or carboxylic anhydride of (a) and the cyclic ether of (b) of the copolymer of (b) and (c) are reacted under the same conditions as those of the process for producing the resin [ K4], whereby the resin [ K5] is obtained.

In the resin [ K5], the ratio of the structural units derived from each unit is preferably 0 to 30 mol% of the structural units derived from (b) (to which (a) is not added), 5 to 95 mol% of the structural units derived from (b) (to which (a) is added), more preferably 0 to 10 mol% of the structural units derived from (b) (to which (a) is not added), 15 to 90 mol% of the structural units derived from (b) (to which (a) is added), 10 to 85 mol% of the structural units derived from (c) (to which (a) is not added), and still more preferably 0 to 5 mol% of the structural units derived from (b) (to which (a) is not added), and 20 to 80 mol% of the structural units derived from (b) (to which (a) is added), and 20 to 80 mol% of the structural units derived from (c) among all the structural units constituting the resin [ K5 ].

The total of the structural units derived from (b) (not added with (a)), the structural units derived from (b) (added with (a) and the structural units derived from (c) may be 90 mol% or more, for example, 95 mol% or more, more preferably 98 mol% or more, and still more preferably 100 mol% of all the structural units constituting the resin [ K5 ].

The amount of (a) to be reacted with the copolymer is preferably 5 to 100 moles based on 100 moles of (b). The (b) used in the resin [ K5] is preferably (b 1), more preferably (b 1-1), from the viewpoint of high reactivity of the cyclic ether and less easiness of residue of the unreacted (b).

The resin [ K5' ] can be produced by referring to the method for producing the resin [ K4 ].

In the resin [ K5'], the ratio of the structural units derived from each unit is preferably 0 to 30 mol% of the structural units derived from (a) (to which (b) is not added), 5 to 95 mol% of the structural units derived from (a) (to which (b) is added), 5 to 95 mol% of the structural units derived from (c), more preferably 0 to 10 mol% of the structural units derived from (a) (to which (b) is not added), 15 to 90 mol% of the structural units derived from (a) (to which (b) is added), 10 to 85 mol% of the structural units derived from (c), still more preferably 0 to 5 mol% of the structural units derived from (a) (to which (b) is not added), 20 to 80 mol% of the structural units derived from (a) (to which (b) is added), and 20 to 80 mol% of the structural units derived from (c) among all the structural units constituting the resin [ K5' ].

The total of the structural units derived from (a) (not added with (b)), the structural units derived from (a) (added with (b) and the structural units derived from (c) may be 90 mol% or more, for example, 95 mol% or more, more preferably 98 mol% or more, and still more preferably 100 mol% of all the structural units constituting the resin [ K5' ].

The structural unit derived from (a) (to which (b) is not added) may be a structural unit derived from an unsaturated monocarboxylic acid such as (meth) acrylic acid. Examples of the structural unit obtained by adding the structural unit derived from (a) to (b) include structural units obtained by adding a structural unit derived from an unsaturated monocarboxylic acid such as (meth) acrylic acid to a monomer (b 1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized. Examples of the structural unit derived from (c) include (meth) acrylates having a linear or branched aliphatic saturated hydrocarbon group and (meth) acrylates having a cyclic saturated hydrocarbon group.

(B) The amount of (a) used may be more than 80 mol and 100 mol or less based on 100 mol of (a).

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

Examples of the polycarboxylic acid include oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, and tricarballylic acid (Tricarballylic acid). Examples of the carboxylic anhydride include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5, 6-tetrahydrophthalic anhydride, 1,2,3, 6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5, 6-dicarboxyibicyclo [2.2.1] hept-2-ene anhydride. The amount of the polycarboxylic acid and/or carboxylic anhydride to be used is preferably from 0.05 to 1 mol, more preferably from 0.1 to 0.5 mol, based on 1 mol of the amount of (a) to be used.

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

Examples of the resin having a structural unit having a (meth) acryloyl group in a side chain include a resin [ K4] using a monomer having a (meth) acryloyl group such as glycidyl (meth) acrylate, 3, 4-epoxycyclohexylmethyl (meth) acrylate, 3-methyl-3-methacryloxymethyl oxetane, tetrahydrofurfuryl acrylate, etc., a resin [ K5] using a monomer having a (meth) acryloyl group such as acrylic acid, methacrylic acid, succinic acid mono [2- (meth) acryloxyethyl ] ester, etc., or a resin [ K6] using a monomer having a (meth) acryloyl group such as acrylic acid, methacrylic acid, succinic acid mono [2- (meth) acryloxyethyl ] ester, etc. As the resin having a structural unit having a (meth) acryloyl group in a side chain, a monomer having a (meth) acryloyl group such as acrylic acid, methacrylic acid, and succinic acid mono [2- (meth) acryloyloxyethyl ] ester is preferably used as the resin [ K6] of (a).

The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 3000 to 100000, more preferably 4000 to 50000, and even more preferably 5000 to 30000. When the molecular weight is within the above range, the hardness of the color filter tends to be high, the residual film ratio tends to be high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern tends to be high.

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

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

The content of the resin (B) is preferably 5 to 60% by mass, more preferably 10 to 55% by mass, and even more preferably 20 to 50% by mass, based on the total amount of the solid components of the colored curable composition. When the content of the resin (B) is within the above range, a colored pattern may be formed, and the resolution of the colored pattern and the residual film ratio 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 capable of being polymerized by a living radical and/or an acid generated by the polymerization initiator (D). Examples of the polymerizable compound (C) include compounds having a polymerizable ethylenically unsaturated bond. The polymerizable compound (C) is preferably a (meth) acrylate compound.

The polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include glycerol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, ethylene 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, caprolactone modified dipentaerythritol hexa (meth) acrylate, and the like. Among them, 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% by mass, more preferably 5 to 50% by mass, and even more preferably 10 to 40% by mass, based on the total amount of the solid components of the colored curable composition. When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming a colored pattern and the chemical resistance of the color filter tend to be improved.

Polymerization initiator (D) >)

The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating a living radical, an acid, or the like under the action of light or heat and initiating polymerization, and a known polymerization initiator can be used. Examples of the polymerization initiator generating active radicals include O-acyl oxime compounds, alkyl phenone compounds, triazine compounds, acyl phosphine oxide compounds, and bisimidazole compounds.

The O-acyl oxime compound is a compound having a partial structure represented by the formula (d 1). Hereinafter, the bonding site is represented.

Examples of the O-acyloxime compound 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-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethane-1-imine, N-acetoxy-1- [ 9-ethyl-6- { 2-methyl-4- (3, 3-dimethyl-2, 4-dioxacyclopentylmethoxy) benzoyl } -9H-carbazol-3-yl ] ethane-1-imine, N-acetoxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -3-cyclopropane-1-imine, N-acetoxy-1- [ 9-ethyl-6- (2-phenylsulfanyloxy) -6-phenyloxy-methyl-3-carbazol-yl ] -3-one-imine. As the O-acyl oxime compound, commercially available products such as Irgacure (registered trademark, the same applies hereinafter) OXE01 (N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine), irgacure OXE02 (N-acetoxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethane-1-imine) (all of which are manufactured by BASF corporation), N-1919, NCI-831 ((manufactured by ADEKA) and the like can be used.

Among them, the O-acyloxime compound is preferably at least 1 selected from the group consisting of N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-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- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, more preferably N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine, or N-acetoxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9-methyl-3-yl ] ethane-1-imine. When such an O-acyl oxime compound is used, there is a tendency that a color filter with high brightness is obtained.

The alkylbenzene ketone compound is a compound having a partial structure represented by the formula (d 2) or a partial structure represented by the formula (d 3). In these partial structures, the benzene ring may have a substituent.

Examples of the compound having a partial structure represented by the formula (d 2) include 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, 2- (dimethylamino) -2- [ (4-methylphenyl) methyl ] -1- [4- (4-morpholinyl) phenyl ] butan-1-one, and the like. As the compound having a partial structure represented by the formula (d 2), commercially available products such as Irgacure 369, 907, 379 (all of them are manufactured by BASF corporation) can be used.

Examples of the compound having a partial structure represented by the formula (d 3) include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] propan-1-one, 1-hydroxycyclohexylphenyl ketone, an oligomer of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, α -diethoxyacetophenone, benzil dimethyl ketal, and the like.

The alkylbenzene ketone compound is preferably a compound having a partial structure represented by the formula (d 2) in terms of sensitivity.

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

Examples of the acylphosphine oxide compound include 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide and the like. As the acylphosphine oxide compound, commercially available products such as Irgacure 819 (manufactured by BASF) and the like can be used.

Examples of the bisimidazole compound include 2,2 '-bis (2-chlorophenyl) -4,4',5 '-tetraphenylbisimidazole and 2,2' -bis (2, 3-dichlorophenyl) -4,4', 5' -tetraphenylbisimidazole (for example, reference is made to Japanese patent application laid-open No. 6-75372, japanese patent application laid-open No. 6-75373, etc.), 2 '-bis (2-chlorophenyl) -4,4',5 '-tetraphenylbiimidazole, 2' -bis (2-chlorophenyl) -4,4',5,5' -tetrakis (alkoxyphenyl) biimidazole, 2 '-bis (2-chlorophenyl) -4,4',5 '-tetrakis (dialkoxyphenyl) biimidazole, 2' -bis (2-chlorophenyl) -4,4', 5' -tetrakis (trialkoxyphenyl) biimidazole (for example, refer to Japanese patent application laid-open No. 48-38403, japanese patent application laid-open No. 62-174204, etc.), biimidazole compounds in which the phenyl group at the 4,4', 5' -position is substituted with a carboalkoxy group (for example, refer to Japanese patent application laid-open No. 7-10913, etc.), and the like.

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, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4 ' -methyldiphenyl sulfide, 3', 4' -tetrakis (t-butylperoxycarbonyl) benzophenone, and 2,4, 6-trimethylbenzophenone; quinone compounds such as 9, 10-phenanthrenequinone, 2-ethylanthraquinone, camphorquinone, and the like; 10-butyl-2-chloroacridone, benzil, methyl benzoylformate, a titanocene compound, and the like. These are preferably used in combination with a polymerization initiator (D1) (particularly an amine) to be described later.

Examples of the polymerization initiator for acid production include onium salts such as 4-hydroxyphenyldimethyl sulfonium p-toluene sulfonate, 4-hydroxyphenyldimethyl sulfonium hexafluoroantimonate, 4-acetoxyphenyl dimethyl sulfonium p-toluene sulfonate, 4-acetoxyphenyl methylbenzyl sulfonium hexafluoroantimonate, triphenylsulfonium p-toluene sulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluene sulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyl tosylate, benzoin tosylate, and the like.

The polymerization initiator (D) is preferably a polymerization initiator containing at least 1 selected from the group consisting of an O-acyl oxime compound, an alkyl phenone compound, a triazine compound, an acyl phosphine oxide compound and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyl oxime compound.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be high and the exposure time tends to be shortened, and therefore improvement in productivity of the color filter can be expected.

Polymerization initiation aid (D1) >, polymerization initiation aid

The polymerization initiator aid (D1) is a compound or sensitizer for promoting the polymerization of the polymerizable compound. When the colored curable composition contains the polymerization initiator (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, and the like.

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-dimethyl-p-toluidine, 4 '-bis (dimethylamino) benzophenone (known as Michaelis' ketone), 4 '-bis (diethylamino) benzophenone, and 4,4' -bis (ethylmethylamino) benzophenone. As the amine compound, commercially available products such as EAB-F (manufactured by Baogu chemical Co., ltd.) can be used. Among them, the amine compound is preferably 4,4' -bis (diethylamino) benzophenone.

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

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

Examples of the carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorobenzylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthyloxyacetic acid, and the like.

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

Zirconium oxide particle (E) >)

The colored curable composition of the present embodiment contains zirconia (zirconia, zrO ₂) particles (E). According to the colored curable composition containing the zirconia particles (E), a cured coating film having less possibility of surface roughness during ashing treatment can be formed. The reason for such effects is not clear, but it is considered that the zirconia particles (E) are added to protect the cured coating film from oxygen plasma and suppress vaporization and decomposition of the cured coating film more than necessary.

The average particle diameter of the zirconia particles (E) is preferably 0.1 μm or less (100 nm), more preferably 0.05 μm or less (50 nm) from the viewpoint of transparency. The average particle diameter of the zirconia particles (E) is usually 0.01 μm or more (10 nm). In the present specification, the average particle diameter refers to a particle diameter at which 50% of the cumulative value in the particle size distribution is obtained by the laser diffraction scattering method.

The zirconia particles (E) are contained in an amount of 0.5 to 70% by mass based on the total amount of the solid components of the colored curable composition. When the content of the zirconia particles (E) is within the above range, there is a tendency that the effect of the present invention is more sufficiently exhibited. The content of the zirconia particles (E) is preferably 1 mass% or more, more preferably 3 mass% or more, further preferably 5 mass% or more, particularly preferably 7 mass% or more, particularly preferably 10 mass% or more, most preferably 15 mass% or more, preferably 60 mass% or less, more preferably 55 mass% or less, further preferably 50 mass% or less, particularly preferably 45 mass% or less, particularly preferably 40 mass% or less, and most preferably 35 mass% or less, based on the total amount of the solid components of the colored curable composition.

< Solvent (F) >)

The solvent (F) is not particularly limited, and solvents generally used in this field can be used. For example, the number of the cells to be processed, examples thereof include an ester solvent (a solvent containing-COO-and not containing-O-in the molecule) an ether solvent (a solvent containing-O-and not-COO-in the molecule), an ether ester solvent (a solvent containing-COO-and-O-in the molecule), a solvent containing-COO-in the molecule, and a solvent containing-COO-in the molecule an ether solvent (a solvent containing-O-and not-COO-in the molecule) ether ester solvents (solvents containing-COO-and-O-in the molecule).

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, 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 γ -butyrolactone.

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

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and the like.

Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, isophorone, and the like.

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

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

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

Among them, the solvent (F) is preferably at least 1 selected from ether ester solvents and ether solvents, 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 component 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, flatness at the time of coating becomes good, and color density at the time of forming a color filter is not easily insufficient, so that display characteristics tend to become good.

When the 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 still more preferably 17 to 80% by mass, based on the total amount of the solvents.

When the 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 still 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, and the like. They may have a polymerizable group in a side chain.

Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, trade names of Toray Silicone DC3PA、Toray Silicone SH7PA、Toray Silicone DC11PA、Toray Silicone SH21PA、Toray Silicone SH28PA、Toray Silicone SH29PA、Toray Silicone SH30PA、Toray Silicone SH8400( (manufactured by Kyowa Kagaku Co., ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Xinyue chemical industries, ltd.), and the like are given.

The fluorine-based surfactant may be a surfactant having a fluorocarbon chain in the molecule. Specifically, examples thereof include FLUORAD FC430 (registered trademark), FLUORAD FC431 (manufactured by Sumitomo 3M (Inc.), MEGAFAC (manufactured by registered trademark )F142D、MEGAFAC F171、MEGAFAC F172、MEGAFAC F173、MEGAFAC F177、MEGAFAC F183、MEGAFAC F554、MEGAFAC R30、MEGAFAC RS－718－K(DIC(), F-top EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi material electronics chemical corporation), surflon S381, surflon S382, surflon SC101, surflon SC105 (manufactured by Asahi Kabushiki Kaisha), and E5844 (manufactured by Mitsubishi gold fine chemical corporation).

Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, MEGAFAC F443 (DIC corporation) and the like are exemplified.

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 Components >)

The colored curable composition of the present embodiment may contain, if necessary, a dispersant (H), an ultraviolet absorber (I), a filler, another polymer compound, an adhesion promoter, an antioxidant, a light stabilizer, a chain transfer agent, and other additives known in the art. The colored curable composition of the present embodiment is suitably used for transmitting infrared rays.

[ Method for producing colored curable composition ]

The colored curable composition of the present embodiment can be prepared by mixing, for example, a colorant (a), a resin (B), a polymerizable compound (C), a polymerization initiator (D), zirconia particles (E), a solvent (F), and, if necessary, a polymerization initiator (D1), a leveling agent (G), and other components.

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

The colored curable composition is preferably obtained by mixing the components and then filtering the mixture with a filter having a pore size of about 0.01 to 10. Mu.m.

[ Color Filter and method for manufacturing the same ]

Examples of the method for producing a colored pattern from the colored curable composition of the present embodiment include photolithography, inkjet method, and printing method. Among them, the method of producing a colored pattern is preferably photolithography. Photolithography is a method of applying a colored curable composition to a substrate, drying the composition to form a coating film, and exposing and developing the coating film through a photomask. In photolithography, a cured coating film, which is a cured product of a coating film, can be formed by not using a photomask and/or not performing development at the time of exposure. The colored pattern (pattern cured coating film) or the cured coating film thus formed is the color filter of the present embodiment.

The film thickness of the color filter to be produced is not particularly limited, and may be appropriately adjusted according to the purpose, application, and the like. The film thickness of the color filter may be, for example, 0.1 to 30. Mu.m, preferably 0.1 to 20. Mu.m, more preferably 0.5 to 6. Mu.m.

Examples of the substrate include glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda lime glass having a surface coated with silica; resin sheets such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; a silicon substrate; a substrate on which aluminum, silver/copper/palladium alloy thin films are formed, and the like. Other color filters (colored patterns or cured coating films), resin films, transistors, circuits, and the like may be formed on these substrates.

The formation of each color pixel by photolithography can be performed by using a known or conventional apparatus and conditions. For example, the formation of each color pixel by photolithography can be performed as follows.

First, the colored curable composition is applied onto a substrate, and then dried by heating (prebaking) and/or drying under reduced pressure to remove volatile components such as a solvent, thereby obtaining a smooth coating film.

Examples of the coating method include a spin coating method, a slit, and a spin coating method. The temperature at the time of heat drying is preferably 30 to 120 ℃, more preferably 50 to 110 ℃. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. In the case of drying under reduced pressure, it is preferable to carry out the drying under a pressure of 50 to 150Pa at a temperature of 20 to 25 ℃.

The film thickness of the coating film is not particularly limited, and may be appropriately selected according to the target color filter film thickness.

Next, the coating film is exposed to light through a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the intended use may be used.

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

In the exposure, in order to uniformly irradiate the entire exposure surface with parallel light and to precisely align the photomask and the substrate on which the coating film is formed, an exposure apparatus such as a mask aligner and a stepper is preferably used.

The exposed coating film (i.e., cured coating film) is brought into contact with a developer and developed, whereby a colored pattern is formed on the substrate. By development, the unexposed portion of the cured coating film is dissolved in a developer and removed. Examples of the developer 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 the aqueous developer 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 the development method include spin immersion (pad method), dipping, and spraying. In the development, the substrate may be inclined at an arbitrary angle. After development, the resulting colored pattern is preferably washed with water.

The resulting colored pattern is preferably post-baked. The post-baking temperature is preferably 150 to 250 ℃, more preferably 160 to 235 ℃. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

[ Display device and solid-state imaging element ]

The display device of the present embodiment includes a color filter as a coloring pattern, a cured coating film, or the like. The solid-state imaging device of the present embodiment includes a color filter as a coloring pattern, a cured coating film, or the like.

The color curable composition according to the present embodiment can be used to produce, for example, a color filter. The color filter is useful as a film used for a display device such as a liquid crystal display device, an electroluminescent display device, or a plasma display, or a solid-state imaging element such as a CCD or CMOS sensor.

Examples

The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to the following examples, and can be carried out with appropriate modifications within the scope suitable for the above-described and the following gist, and these are included in the technical scope of the present invention. Hereinafter, "parts" means "parts by mass" and "%" means "% by mass" unless otherwise specified.

In the following examples, "room temperature" means 18 to 24 ℃.

In the following examples, the structure of the compound was confirmed by a MASS spectrometer (MALDI-TOF MS: manufactured by Japan electronics Co., ltd. "JMS-S3000") or a MASS spectrometer (LC: model 1200 by Agilent Co., ltd. "MASS: model LC/MSD6130 by Agilent Co.).

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by GPC under the following conditions.

HLC-8120GPC (manufactured by Tosoh Co., ltd.)

Column TSK-GELG HXL 2000HXL

Column temperature of 40 DEG C

Solvent tetrahydrofuran

Flow Rate 1.0 mL/min

The concentration of the solid content of the analysis sample is 0.001 to 0.01 mass%

Sample injection amount 50. Mu.L

Detector RI

Calibration standard materials TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corp.)

The dispersion was defined as the ratio (Mw/Mn) of the weight average molecular weight to the number average molecular weight in terms of polystyrene obtained above.

Synthesis example 1

Synthesis of Compound (colorant A-1) represented by the formula (1)

The compound represented by the following formula (1) was synthesized according to the description of International publication No. 2022/024926.

< Identification of Compound represented by formula (1) >)

Ionization mode (Mass Spectrometry) =MALDI-TOF ^－:m/z=740.3

Accurate molecular weight 740.2

< Absorbance of maximum absorption wavelength of Compound represented by formula (1) in visible light region >

The absorbance at the maximum absorption wavelength in the visible light region was obtained by the following method. First, 0.1mg of colorant (A) and 20g of PGMEA were added to a sample bottle, and the mixture was stirred at 25℃for 2 hours. Then, the solid phase and the liquid phase were separated by filtration ((PTFE membrane, pore size: 0.45 μm)), and the absorption spectrum of the liquid phase was measured at 25℃using a spectrophotometer (for example, glass cuvette having a light path length of 10mm by Japan Spectrometry "JASCO V-650") with PGMEA as a base line for the solution spectrum of the liquid phase. In the obtained absorption spectrum, the absorbance was obtained from the maximum absorption wavelength in the visible light region between 380 and 780nm, and was found to be 0.6.

Synthesis example 2

< Synthesis of Compound (colorant A-3) represented by formula (3) >)

2, 6-Diphenylaniline was synthesized by the method described in reference ARKIVOC,2012,9,62-75. 4.00 parts of the compound represented by the formula (3 a), 9.69 parts of 2, 6-diphenylaniline, 2.69 parts of zinc chloride (Fuji photo-Kagaku Co., ltd.) and 24.0 parts of sulfolane (Tokyo chemical Co., ltd.) were mixed at room temperature, and the mixture was heated to 250℃and stirred for 4 hours. After cooling the reaction mixture to room temperature, 48.0 parts of 1N hydrochloric acid was added, and the obtained precipitate was taken out as a residue after suction filtration, and further washed with 24.0 parts of toluene, 18.0 parts of DMF and 20.0 parts of DMF in this order. The obtained residue was dried to obtain 5.18 parts of the compound represented by the formula (3). The yield thereof was found to be 64%.

< Identification of Compound represented by formula (3) >)

Ionization mode of (mass spectrum = ESI ⁺:m/z＝[M+H]⁺ 823.3

Accurate molecular weight 823.3

< Absorbance of maximum absorption wavelength of Compound represented by formula (3) in visible light region >

The absorbance of the compound represented by formula (3) at the maximum absorption wavelength in the visible light region was obtained in the same manner as the method for measuring the absorbance of the compound represented by formula (1) at the maximum absorption wavelength in the visible light region. The absorbance at the maximum absorption wavelength was 0.7.

Synthesis example 3

< Synthesis of resin B-1 >

A flask equipped with a reflux condenser, a dropping funnel and a stirrer was charged with an appropriate amount of nitrogen and replaced with a nitrogen atmosphere, 340 parts of PGMEA was charged, and the mixture was heated to 80℃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 (containing a molar ratio of 1:1), 239 parts of benzyl methacrylate, and 73 parts of PGMEA was added dropwise over 5 hours. On the other hand, a solution in which 40 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile), a polymerization initiator, was dissolved in 197 parts of PGMEA was added dropwise over 6 hours. After completion of the addition of the solution containing the polymerization initiator, the mixture was kept at 80℃for 3 hours and then cooled to room temperature, whereby a copolymer (resin B-1) solution having a viscosity of 137 mPas and a solid content of 36.8 mass% as measured by a B-type viscometer (23 ℃) was obtained. The polystyrene-equivalent weight average molecular weight of the resulting copolymer was 1.0X10- ³, the dispersity was 1.97, and the acid value in terms of solid content was 111mg-KOH/g. The resin B-1 has the following structural units.

Synthesis example 4

< Synthesis of resin B-2 >

To a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer and a gas inlet tube, 276.8 parts of PGMEA was added, and the mixture was stirred and heated to 120 ℃ while nitrogen was being substituted. Next, 35.3 parts of t-butyl peroxy-2-ethylhexanoate (polymerization initiator) was added to a monomer mixture of 92.4 parts of 2-ethylhexyl acrylate, 184.9 parts of glycidyl methacrylate and 12.3 parts of dicyclopentanyl methacrylate, which was added dropwise from a dropping funnel to the flask over 2 hours. After the completion of the dropwise addition, the mixture was further stirred at 120℃for 30 minutes to carry out copolymerization to synthesize an addition copolymer. Then, 93.7 parts of acrylic acid, 1.5 parts of triphenylphosphine (catalyst) and 0.8 parts of methoxyphenol (polymerization inhibitor) were put into the addition copolymer solution, and the reaction was continued at 110℃for 10 hours, whereby the epoxy group derived from glycidyl methacrylate was cleaved by the reaction of the epoxy group with acrylic acid, and a polymerizable unsaturated bond was introduced into the side chain of the addition copolymer. Then, 24.2 parts of succinic anhydride was added to the reaction system, and the reaction was continued at 110℃for 1 hour, whereby the hydroxyl group generated by 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 was added to the reaction solution to obtain a 40% by mass solid content copolymer (resin B-2) solution. The polystyrene-equivalent weight average molecular weight of the resulting copolymer was 6.3X10- ³, and the acid value in terms of solid content was 34mg-KOH/g.

Synthesis example 5

< Preparation of Dispersion 1 >

5.0 Parts of the compound represented by the formula (1), 2.9 parts of a dispersant (BYK corporation "BYKLPN-6919"), 2.4 parts of resin B-1 (in terms of solid content), and 89.7 parts of PGMEA (the solvent part containing the resin B-1 solution) were mixed, and 300 parts of zirconia beads of 0.4mm were added thereto, and the mixture was shaken for 1 hour using a paint conditioner (Paint Conditioner) (manufactured by LAU corporation). Then, zirconia beads were removed by filtration to obtain a dispersion 1.

Synthesis example 6

< Preparation of Dispersion 2 >

8.0 Parts of a compound represented by the formula (2) (colorant A-2,TAIYO Fine Chemicals, inc. "Pink Base") 2.9 parts of a dispersant (BYK, inc. "BYKLPN-6919"), 2.9 parts of a resin B-1 (in terms of solid content), and 86.2 parts of PGMEA (the solvent fraction containing the resin B-1 solution) were mixed, 300 parts of a zirconia bead of 0.4mm was added, and the mixture was shaken for 1 hour using a paint conditioner (LAU, inc.). Then, zirconia beads were removed by filtration to obtain a dispersion 2.

< Absorbance of maximum absorption wavelength of Compound represented by formula (2) in visible light region >

The absorbance of the compound represented by formula (2) at the maximum absorption wavelength in the visible light region was obtained in the same manner as the method for measuring the absorbance of the compound represented by formula (1) at the maximum absorption wavelength in the visible light region. The absorbance at the maximum absorption wavelength was 0.4.

Synthesis example 7

< Preparation of Dispersion 3 >

8.0 Parts of the compound represented by the formula (3), 2.9 parts of a dispersant (BYK corporation "BYKLPN-6919"), 2.9 parts of resin B-1 (in terms of solid content), and 86.2 parts of PGMEA (the solvent part containing the resin B-1 solution) were mixed, 300 parts of zirconia beads of 0.4mm were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU corporation). Then, zirconia beads were removed by filtration to obtain a dispersion 3.

Synthesis example 8

Preparation of zirconium oxide Dispersion 1

A300 mL bottle was charged with 14 parts of a dispersant (solid content: 50% by mass, acid value in terms of solid content: 100mg-KOH/g, weight average molecular weight: 3000, solvent PGMEA), 35 parts of zirconia particles, 51 parts of PGMEA, and 150 parts of zirconia beads having an average particle diameter of 50 μm as a dispersion medium, and dispersed at 60Hz for 10 hours using a disperser ((product: SEIWAG, product: rocking Shaker RS-05W). Then, zirconia beads were removed by filtration, thereby obtaining a zirconia dispersion 1. The nonvolatile content (solid content) in the zirconia dispersion 1 was 42 mass%, and the average particle diameter of the zirconia particles was 30nm.

Synthesis example 9

< Preparation of Dispersion 4 >

C.I. pigment Red 254.1 parts, 2.4 parts of a dispersant (BYK company "BYKLPN-6919"), 3.0 parts of resin B-1 (in terms of solid content), and 82.5 parts of PGMEA (the solvent part containing the resin B-1 solution) were mixed, and 300 parts of 0.4mm zirconia beads were added thereto, followed by shaking for 1 hour using a paint conditioner (LAU company). Then, zirconia beads were removed by filtration to obtain a dispersion 4.

< Absorbance of maximum absorption wavelength of pigment Red 254 existing in visible light region >

The absorbance of c.i. pigment red 254 at the maximum absorption wavelength in the visible light region was obtained in the same manner as the method for measuring the absorbance of the compound represented by formula (1) at the maximum absorption wavelength in the visible light region. The absorbance at the maximum absorption wavelength was 0.1.

Synthesis example 10

< Preparation of Dispersion 5 >

A mixture of 58.0 parts of C.I. pigment green, 3.0 parts of dispersant (BYK company "BYKLPN-6919"), 3.7 parts of resin B-1 (in terms of solid content) and 78.3 parts of PGMEA (the solvent fraction containing the resin B-1 solution) was added to 300 parts of 0.4mm zirconia beads, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU company). Then, zirconia beads were removed by filtration to obtain a dispersion 5.

< Absorbance of maximum absorption wavelength of pigment Green 58 existing in visible light region >

The absorbance of the c.i. pigment green 58 at the maximum absorption wavelength in the visible light region was obtained in the same manner as the method for measuring the absorbance of the compound represented by formula (1) at the maximum absorption wavelength in the visible light region. The absorbance at the maximum absorption wavelength was 0.04.

Synthesis example 11

< Preparation of Dispersion 6 >

36.0 Parts of C.I. pigment green, 2.8 parts of dispersant (BYK company "BYKLPN-6919"), 2.8 parts of resin B-1 (in terms of solid content), and 80.4 parts of PGMEA (the solvent fraction containing the resin B-1 solution) were mixed, 300 parts of 0.4mm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU company). Then, zirconia beads were removed by filtration to obtain a dispersion 6.

< Absorbance of maximum absorption wavelength of pigment Green 36 existing in visible light region >

The absorbance of the c.i. pigment green 36 at the maximum absorption wavelength in the visible light region was obtained in the same manner as the method for measuring the absorbance of the compound represented by formula (1) at the maximum absorption wavelength in the visible light region. The absorbance at the maximum absorption wavelength was 0.04.

Synthesis example 12

< Preparation of Dispersion 7 >

C.I. pigment blue 15:6.0 parts, dispersant (BYK company "BYKLPN-6919") 4.4 parts, resin B-1 (in terms of solid content) 4.8 parts, and PGMEA78.8 parts (the solvent fraction containing the resin B-1 solution) were mixed, and 300 parts of 0.4mm zirconia beads were added thereto, followed by shaking for 1 hour using a paint conditioner (manufactured by LAU company). Then, zirconia beads were removed by filtration to obtain a dispersion 7.

< Absorbance of C.I. pigment blue 15:6 at maximum absorption wavelength in visible region >

The absorbance of the maximum absorption wavelength of c.i. pigment blue 15:6 in the visible light region was obtained in the same manner as the method for measuring the absorbance of the maximum absorption wavelength of the compound represented by formula (1) in the visible light region. The absorbance at the maximum absorption wavelength was 0.1.

Synthesis example 13

< Preparation of Dispersion 8 >

C.I. pigment Red 291.9 parts, 4.4 parts of a dispersant (BYK company "BYKLPN-6919"), 2.0 parts of resin B-1 (in terms of solid content), and 71.7 parts of PGMEA (the solvent fraction containing the resin B-1 solution) were mixed, and 300 parts of 0.4mm zirconia beads were added thereto, and the mixture was shaken for 1 hour using a paint conditioner (Paint Conditioner) (manufactured by LAU Co.). Then, zirconia beads were removed by filtration to obtain a dispersion 8.

< Absorbance of C.I. pigment Red 291 at maximum absorption wavelength in visible light region >

The absorbance of c.i. pigment red 291 at the maximum absorption wavelength in the visible light region was obtained in the same manner as the method for measuring the absorbance at the maximum absorption wavelength in the visible light region of the compound represented by formula (1). The absorbance at the maximum absorption wavelength was 0.1.

Synthesis example 14

< Preparation of Dispersion 9 >

150.1 Parts of C.I. pigment yellow, 4.9 parts of dispersant (BYK company "BYKLPN-6919"), 3.6 parts of resin B-1 (in terms of solid content), and 79.4 parts of PGMEA (the solvent fraction containing the resin B-1 solution) were mixed, 300 parts of 0.4mm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU company). Then, zirconia beads were removed by filtration to obtain a dispersion 9.

< Absorbance of C.I. pigment yellow 150 at maximum absorption wavelength in visible light region-

The absorbance of c.i. pigment yellow 150 at the maximum absorption wavelength in the visible light region was obtained in the same manner as the method for measuring the absorbance at the maximum absorption wavelength in the visible light region of the compound represented by formula (1). The absorbance at the maximum absorption wavelength was 0.7.

Synthesis example 15

< Preparation of Dispersion 10 >

C.I. pigment blue (16.0 parts), dispersant (BYK company "BYKLPN-6919") (4.8 parts), resin B-1 (in terms of solid content) (3.6 parts) and PGMEA (79.7 parts) (solvent part containing resin B-1 solution) were mixed, and 300 parts of 0.4mm zirconia beads were added thereto, followed by shaking for 1 hour using a paint conditioner (manufactured by LAU company). Then, zirconia beads were removed by filtration to obtain a dispersion 10.

< Absorbance of maximum absorption wavelength of pigment blue 16 existing in visible light region >

The absorbance of the c.i. pigment blue 16 at the maximum absorption wavelength in the visible light region was obtained in the same manner as the method for measuring the absorbance of the compound represented by formula (1) at the maximum absorption wavelength in the visible light region. The absorbance at the maximum absorption wavelength was 0.2.

Examples 1 to 13 and comparative example 1

< Preparation of colored curable composition >

The colored curable compositions of examples 1 to 13 and comparative example 1 were prepared by mixing the components (units: parts) shown in Table 3 and Table 4.

(1) Dispersion 1 (Synthesis example 5)

(Colorant A-1: 5.0 parts of the Compound (Synthesis example 1) represented by the formula (1)

Resin B-1 resin (Synthesis example 3) (solid content conversion) 2.4 parts

Solvent F-1 PGMEA89.7 parts (solvent fraction containing resin B-1 solution)

Dispersant H-1 dispersant (BYK company "BYKLPN-6919") 2.9 parts

(2) Dispersion 2 (Synthesis example 6)

(Colorant A-2: 8.0 parts of Compound (Pink Base manufactured by TAIYO FINE CHEMICALS Co., ltd.) represented by the formula (2)

Resin B-1 resin (Synthesis example 3) (solid content conversion) 2.9 parts

Solvent F-1 PGMA 86.2 parts (solvent fraction containing resin B-1 solution)

Dispersant H-1 dispersant (BYK company "BYKLPN-6919") 2.9 parts

(3) Dispersion 3 (Synthesis example 7)

(Colorant A-3: 8.0 parts of the Compound represented by the formula (3) (Synthesis example 2)

Resin B-1 resin (Synthesis example 3) (solid content conversion) 2.9 parts

Solvent F-1 PGMA 86.2 parts (solvent fraction containing resin B-1 solution)

Dispersant H-1 dispersant (BYK company "BYKLPN-6919") 2.9 parts

(4) Dispersion 4 (Synthesis example 9)

(Colorant A-4:C.I. pigment Red 254.1 parts)

Resin B-1 resin (Synthesis example 3) (solid content conversion) 3.0 parts

Solvent F-1 PGME82.5 parts (solvent fraction containing resin B-1 solution)

Dispersant H-1 dispersant (BYK company "BYKLPN-6919") 2.4 parts

(5) Dispersion 5 (Synthesis example 10)

(Colorant A-5: C.I. pigment Green 58.0 parts)

Resin B-1 resin (Synthesis example 3) (solid content conversion) 3.7 parts

Solvent F-1 PGMEA78.3 parts (solvent fraction containing resin B-1 solution)

Dispersant H-1 dispersant (BYK company's "BYKLPN-6919") 3.0 parts

(6) Dispersion 6 (Synthesis example 11)

(Colorant A-6: C.I. pigment Green 36.0 parts)

Resin B-1 resin (Synthesis example 3) (solid content conversion) 2.8 parts

Solvent F-1 PGMEA80.4 parts (solvent fraction containing resin B-1 solution)

Dispersant H-1 dispersant (BYK company "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 conversion) 4.8 parts

Solvent F-1 PGMEA78.8 parts (solvent fraction containing resin B-1 solution)

Dispersant H-1 dispersant (BYK company's "BYKLPN-6919") 4.4 parts

(8) Dispersion 8 (Synthesis example 13)

(Colorant A-8: C.I. pigment Red 291.9 parts)

Resin B-1 resin (Synthesis example 3) (solid content conversion) 2.0 parts

Solvent F-1 PGMEA71.7 parts (solvent fraction containing resin B-1 solution)

Dispersant H-1 dispersant (BYK company's "BYKLPN-6919") 4.4 parts

(9) Dispersion 9 (Synthesis example 14)

(Colorant A-9: C.I. pigment yellow 150.1 parts)

Resin B-1 resin (Synthesis example 3) (solid content conversion) 3.6 parts

Solvent F-1 PGMEA79.4 parts (solvent fraction containing resin B-1 solution)

Dispersant H-1 dispersant (BYK Co. "BYKLPN-6919") 4.9 parts

(10) Dispersion 10 (Synthesis example 15)

(Colorant A-10: C.I. pigment blue 16.0 parts)

Resin B-1 resin (Synthesis example 3) (solid content conversion) 3.6 parts

Solvent F-1 PGMEA79.7 parts (solvent fraction containing resin B-1 solution)

Dispersant H-1 dispersant (BYK company's "BYKLPN-6919") 4.8 parts

(11) Zirconia dispersion 1 (synthesis example 8)

(Zirconia particles E-1: zirconia particles (average particle diameter: 30 nm) 35 parts

Dispersant H-2 dispersant (solid content 50% by mass, acid value 100mgKOH/g in terms of solid content, weight average molecular weight 3000, solvent PGMEA) 14 parts

Solvent F-1:PGME51 parts)

(12) Resin B-2 resin (Synthesis example 4) (solid content conversion)

(13) Polymerizable Compound C-1 ethylene oxide-modified dipentaerythritol hexaacrylate (A-DPH-12E, new Zhongcun chemical industry Co., ltd., "number of ethylene oxide chains 6, conversion of solid content)

(14) Polymerizable Compound C-2 Glycerol triacrylate (M-930 manufactured by Toyama Synthesis Co., ltd.)

(15) Polymerization initiator D-1:N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropan-1-one-2-imine

(16) Polymerization initiator D-2 NCI-831 (manufactured by ADEKA)

(17) Solvent F-1 Propylene Glycol Monomethyl Ether (PGME)

(18) Solvent F-2 diacetone alcohol (DAA)

(19) Solvent F-3 PGMEA (the solvent fraction containing the resin B-2 solution in the values of tables 3 and 4 should be noted.)

(20) Leveling agent G-1 polyether modified silicone oil (Dow Corning Toray, co., ltd. "Toray Silicone SH8400", conversion of solid content)

(21) Ultraviolet absorber I-1, "DAINSORB-T0" manufactured by Dahe chemical Co., ltd "

TABLE 3

TABLE 4

< Evaluation of colored Pattern >

Production of colored Pattern for evaluation

The colored curable compositions of examples 1 to 13 and comparative example 1 were applied to a 4-inch silicon substrate by spin coating so that the film thickness after post-baking was 0.8. Mu.m, and then pre-baked at 80℃for 2 minutes to obtain coating films. After cooling, the substrate on which the coating film was formed was irradiated with light at an exposure dose of 300mJ/cm ² (365 nm basis) via a photomask using an exposure machine (NSR-1755 i7A; manufactured by Nikon Co., ltd.). The photomask used was one capable of forming a dot pattern having a square of 5.0 μm on the substrate. The coating film (cured coating film) after the light irradiation was immersed and developed in an aqueous developer containing tetramethylammonium hydroxide at 23 ℃ for 30 seconds, washed with water, and post-baked at 230 ℃ 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 put into a plasma dry cleaner (PDC 510 manufactured by yama science co.) and subjected to O ₂ plasma treatment under conditions of an O ₂ flow rate of 90cc (mL), an RF treatment time of 20 seconds and an RF output of 300W, to obtain a silicon substrate having a colored pattern II.

Evaluation of surface roughness of colored pattern for evaluation

The silicon substrate having the colored pattern I or II obtained as described above was observed at a magnification of 30000 times from the upper surface using an electron microscope (product of hitachi high technology S-4100), and an image of 720 pixels in width and 480 pixels in height was obtained. The acquired image is converted into a gray scale, and the luminance distribution of each pixel is output in the form of a histogram. The histogram of each image was approximated by a gaussian function, and the half-width was evaluated. The half-width becomes narrower in the case of an image having a small and uniform surface roughness, and becomes wider in principle in the case of an image having a large surface roughness. The evaluation was performed in 5 stages A to E according to the following criteria. The results are shown in tables 5 and 6.

A: the half-width is 65 or less.

B: the half-width exceeds 65 and is 70 or less.

C: the half-width exceeds 70 and is 80 or less.

D: the half-width exceeds 80 and is less than 85.

E: the half-width exceeds 85.

TABLE 5

	Coloring pattern I	Coloring pattern II
			Comparative example 1	A	E
Example 1	A	D
			Example 2	A	D
Example 3	A	B
			Example 4	A	A
Example 5	A	A

TABLE 6

	Coloring pattern I	Coloring pattern II
			Example 6	A	A
Example 7	A	D
			Example 8	A	A
Example 9	A	A
			Example 10	A	A
Example 11	A	A
			Example 12	A	A
Example 13	A	A

As shown in tables 5 and 6, the colored patterns of examples 1 to 13 containing zirconia particles in a predetermined range were superior in surface state to the colored pattern of comparative example 1 containing no zirconia particles, based on the total amount of solid components. As the content of zirconia particles increases, the surface state tends to become good. From these results, it was confirmed that the colored curable composition of the present invention can form a cured coating film which is less likely to cause surface roughness by ashing treatment.

Claims

1. A colored curable composition comprising a colorant A, a resin B, a polymerizable compound C, a polymerization initiator D, zirconia particles E and a solvent F,

The colorant a satisfies the following condition (i),

The content of the colorant A is 1% by mass or more based on the total amount of solid components of the colored curable composition,

The zirconia particles E are contained in an amount of 0.5 to 70% by mass based on the total amount of solid components of the colored curable composition,

Under the condition (i), 0.1mg of the colorant A and 20g of propylene glycol monomethyl ether acetate are mixed at 25 ℃ for 2 hours, and the solid phase is separated by filtration, and the absorbance of the liquid phase obtained by the above is less than 2.0 at a maximum absorption wavelength in the visible light region between 380 and 780 nm.

2. The colored curable composition according to claim 1, wherein the colorant A contains a compound selected from the group consisting of xanthene compounds, phthalocyanine compounds, quinophthalone compounds, isoindoline compounds, azo compounds, diketopyrrolopyrrole compounds, perylene compounds, and di-At least 1 compound of the oxazine compound and the anthraquinone compound.

3. A color filter formed from the colored curable composition according to claim 1 or 2.

4. A display device comprising the color filter of claim 3.