TW201731969A - Compound, colored curable resin composition, color filter and liquid crystal display device capable of providing a color filter with excellent thermal resistance and a display device comprising the same - Google Patents

Abstract

This invention aims to provide a compound capable of providing a color filter with excellent thermal resistance and a display device comprising the same and a colored curable resin composition. The solution is a compound characterized by comprising a compound (a) having a cation and an anion in a molecule, an anion (b) containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus, and oxygen as essential elements, and a cation (c) containing alkaline earth metal.

Description

Compound, colored curable resin composition, color filter, and liquid crystal display device

Field of invention

The present invention relates to a compound containing a compound having a cation and an anion in a molecule, a cation, and an anion, a colored curable resin composition using the same, a color filter, and a liquid crystal display device.

Background of the invention

The coating film formed of the colored curable resin composition is excellent in heat resistance and the like, and various techniques have been developed in order to improve heat resistance and the like.

Patent Document 1 describes a colored curable resin composition comprising a salt-forming compound composed of a triarylmethane-based basic dye and a counter-compound thereof.

Prior art literature Patent literature

Patent Document 1: Japanese Laid-Open Patent Publication No. 2014-170098

Summary of invention

In this Patent Document 1, a salt-forming compound is disclosed in terms of improving a desired property, but in all of the patent documents, a compound having both a cation and an anion in a molecule is not taught as having heat resistance. Compound.

Therefore, an object of the present invention is to provide a colored curable resin composition capable of forming a coating film having excellent heat resistance and a compound used in the colored curable resin composition.

That is, the gist of the present invention is as follows.

[1] a compound comprising: a compound (a) having a cation and an anion in a molecule; an anion (b) having at least one element selected from the group consisting of tungsten, molybdenum, rhenium, and phosphorus, and oxygen as an essential element; An alkaline earth metal-containing cation (c).

[2] The compound according to [1], wherein the compound (a) is a xanthene compound (a1).

[3] The compound according to [2], wherein the xanthene compound (a1) is a compound represented by the formula (a1-1).

In the formula (a1-1), R ¹ to R ⁴ each independently represent a hydrogen atom, an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be -O-, -CO-, -N(R ¹⁰ )-, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH-, or -NHCO- replacement. However, the adjacent -CH ₂ - will not be replaced by the same group at the same time, and the -CH ₂ - at the end will not be replaced.

R ¹ and R ² may together form a ring containing a nitrogen atom, and R ³ and R ⁴ may together form a ring containing a nitrogen atom.

R ⁵ and R ⁶ independently of each other represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

R ¹⁰ 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. ]

[4] The compound according to any one of [1], wherein the cation (c) is at least one selected from the group consisting of a magnesium cation, a calcium cation, a phosphonium cation, and a phosphonium cation.

[5] A colored curable resin composition, which comprises the compound according to any one of [1] to [4], a resin, a polymerizable compound, and a polymerization initiator.

[6] A color filter formed from the colored curable resin composition according to [5].

[7] A liquid crystal display device having the color filter according to [6].

According to the invention, it is possible to provide a colored curable resin composition capable of forming a coating film having improved heat resistance, and a compound used therefor.

Detailed description of the preferred embodiment

1. Compound

The compound of the present invention is characterized by comprising: a compound (a) having a cation and an anion in a molecule (hereinafter sometimes referred to as a compound (a);); at least 1 selected from the group consisting of tungsten, molybdenum, rhodium and phosphorus. An anion (b) with an element and oxygen as essential elements; and a cation (c) containing an alkaline earth metal.

1-1. Compound (a)

The compound (a) has a cation and an anion in the molecule. The cations and anions in the molecule may be the same number of charges or different numbers of charges, preferably cations and anions having the same number of charges in the molecule. More preferably, the cation and the anion having the same number of charges of 1 or more and 5 or less in the molecule are more preferably a cation and an anion having the same number of charges of 1 or more and 3 or less in the molecule, and particularly preferably 1 in the molecule. A charge number of cations and anions.

The compound (a) is preferably a xanthene compound (a1) or a squaraine compound (a2).

1-1-1. Xanthene compound

The xanthene compound (a1) is preferably a compound represented by the formula (a1-1) (hereinafter sometimes referred to as "compound (a1)"). Compound (a1) may be a tautomer thereof.

In the formula (a1-1), R ¹ to R ⁴ each independently represent a hydrogen atom, an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be -O-, -CO-, -N(R ¹⁰ )-, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH-, or -NHCO- replacement. However, the adjacent -CH ₂ - will not be replaced by the same group at the same time, and the -CH ₂ - at the end will not be replaced.

R ¹ and R ² may together form a ring containing a nitrogen atom, and R ³ and R ⁴ may together form a ring containing a nitrogen atom.

R ⁵ and R ⁶ independently of each other represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

R ¹⁰ 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 saturated hydrocarbon group having 1 to 20 carbon atoms in R ¹ to R ⁴ and R ¹⁰ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. a linear alkyl group such as a decyl group, a dodecyl group, a hexadecyl group or an eicosyl group; a branched chain alkyl group such as an isopropyl group, an isobutyl group, an isopentyl group, a neopentyl group or a 2-ethylhexyl group; An alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group or a tricyclodecyl group. The saturated hydrocarbon group of R ¹ to R ⁴ and R ¹⁰ is more preferably a carbon number of 1 to 15, more preferably a carbon number of 1 to 10, still more preferably a carbon number of 1 to 6.

The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be -O-, -CO-, -N(R ¹⁰ )-, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH- or -NHCO- replacement. However, the adjacent -CH ₂ - will not be replaced by the same group at the same time, and the -CH ₂ - at the end will not be replaced.

The group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -O- includes, for example, the following groups (* represents a bonding end).

The group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -CO- includes, for example, the following group (* represents a bonding end).

The group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -NR ¹⁰ - may, for example, be the following group (* represents a bonding end).

The group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -OCO- includes, for example, the following groups (* represents a bonding end).

The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -COO-, and examples thereof include the following groups (* represents a bonding end).

The group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -OCONH- includes, for example, the following group (* represents a bonding end).

The group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -NHCOO- includes, for example, the following group (* represents a bonding end).

The group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -CONH- includes, for example, the following group (* represents a bonding end).

The group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -NHCO- includes, for example, the following group (* represents a bonding end).

Examples of the substituent which the saturated hydrocarbon group represented by R ¹ to R ⁴ may have include an aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom.

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include a phenyl group, a tolyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group.

Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.

Examples of the ring formed by R ¹ and R ² together with the ring formed by R ³ and R ⁴ include the following rings.

Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R ¹ to R ⁴ include a phenyl group, a tolyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group.

The aromatic hydrocarbon group having 6 to 10 carbon atoms may have a substituent. Examples of the substituent which the aromatic hydrocarbon group may have include a halogen atom, -R ⁷ , -OH, -OR ⁷ , -SO ₃ ^- , -SO ₃ H, -SO ₃ ^- Z ⁺ , -CO ₂ H, -CO ₂ R ⁷ , -SR ⁷ , -SO ₂ R ⁷ , -SO ₃ R ⁷ and -SO ₂ N(R ⁸ )(R ⁹ ).

R ⁷ represents an alkyl group having 1 to 10 carbon atoms which may have a halogen atom. The methylene group contained in the alkyl group having 1 to 10 carbon atoms may be replaced by an oxygen atom, a carbon group or -N(R ⁷ )-. However, the adjacent methylene groups are not replaced by the same group at the same time, and the methylene group at the end is not replaced.

R ⁸ and R ⁹ independently of each other represent a hydroxyl group or a saturated hydrocarbon group having 1 to 10 carbon atoms or a hydrogen atom which may be substituted by a halogen atom.

Examples of the saturated hydrocarbon group having 1 to 10 carbon atoms include alkyl groups having 1 to 10 carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group and a heptyl group.

Examples of -OR ⁷ include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group and two. An alkoxy group such as a decadecyloxy group.

Examples of the -CO ₂ R ⁷ include alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an eicosyloxycarbonyl group.

Examples of -SR ⁷ include alkylsulfane groups such as methylsulfanyl, ethylsulfanyl, butylsulfanyl, hexylsulfanyl, mercaptosulfanyl and eicosylsulfanyl groups. Base.

Examples of the -SO ₂ R ⁷ include an alkyl group such as a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a nonylsulfonyl group, and an eicosylsulfonyl group. Sulfonyl and the like.

Examples of -SO ₃ R ⁷ include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an eicosane. An alkoxysulfonyl group such as oxysulfonyl group.

Examples of -SO ₂ N(R ⁸ )(R ⁹ ) include an aminesulfonyl group; an N-methylaminesulfonyl group, an N-ethylaminesulfonyl group, and an N-propylaminesulfonyl group; N-isopropylamine sulfonyl, N-butylamine sulfonyl, N-isobutylamine sulfonyl, N-sec-butylamine sulfonyl, N-tert-butylamine sulfonyl , N-pentylamine sulfonyl, N-(1-ethylpropyl)amine sulfonyl, N-(1,1-dimethylpropyl)amine sulfonyl, N-(1,2- Dimethylpropyl)aminesulfonyl, N-(2,2-dimethylpropyl)aminesulfonyl, N-(1-methylbutyl)aminesulfonyl, N-(2-A Alkyl butyl sulfonyl, N-(3-methylbutyl) sulfonyl, N-cyclopentylamine sulfonyl, N-hexylamine sulfonyl, N-(1,3-) Methylbutyl)aminesulfonyl, N-(3,3-dimethylbutyl)aminesulfonyl, N-heptylaminesulfonyl, N-(1-methylhexyl)aminesulfonyl , N-(1,4-dimethylpentyl)amine sulfonyl, N-octylamine sulfonyl, N-(2-ethylhexyl)amine sulfonyl, N-(1,5-di N-substituted sulfonyl group such as methylhexyl)aminesulfonyl, N-(1,1,2,2-tetramethylbutyl)aminesulfonyl; N,N-dimethylaminesulfonate Base, N, N-ethylmethylamine sulfonyl, N,N-diethylamine sulfonyl, N,N- Methylamine sulfonyl, N,N-isopropylmethylamine sulfonyl, N,N-tert-butylmethylamine sulfonyl, N,N-butylethylamine sulfonyl, N, An N,N-2 substituted amine sulfonyl group such as N-bis(1-methylpropyl)amine sulfonyl group or N,N-heptylmethylamine sulfonyl group.

Examples of the alkyl group having 1 to 6 carbon atoms in R ⁵ and R ⁶ include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, an isopentyl group, and a pentyl group. Among them, as R ⁵ and R ⁶ , a hydrogen atom is preferred.

R ⁸ and R ⁹ independently of each other represent a 3 to 10 membered nitrogen-containing heterocyclic ring together with a nitrogen atom. Examples of the hetero ring include the following heterocyclic rings.

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

Z ⁺ is ⁺ N(R ¹⁰ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N(R ¹⁰ ) ₄ .

As the above ⁺ N(R ¹⁰ ) ₄ , at least two of the four R ¹⁰ are preferably a monovalent saturated hydrocarbon group having 5 to 20 carbon atoms. Further, the total carbon number of the four R ¹⁰ is preferably 20 to 80, and more preferably 20 to 60. In the case where ⁺ N(R ¹⁰ ) ₄ is present in the compound (a1), when R ¹⁰ is such a group, the color-developable resin composition of the present invention containing the compound (a1) can form a color filter having less foreign matter. .

Among these, as the substituent, -R ⁷ , -SO ₃ ^- , -SO ₃ H, -SO ₃ ^- Z ⁺ and -SO ₂ N(R ⁸ )(R ⁹ ) are preferable, and -R ⁷ and -SO are more preferable. ₃ ^- Z ⁺ and -SO ₂ N(R ⁸ )(R ⁹ ). The -R ^{7 in} this case is more preferably a monovalent alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, still more preferably a methyl group or an ethyl group. Further, as -SO ₃ ^- Z ^{+ in} this case, -SO ₃ ^-+ N(R ¹⁰ ) ₄ is preferable.

In the formula (a1-1), -SO ₃ ^- is preferably selected from the following formulas (Z ⁵ -1) to (Z ⁵ -5), and more preferably the formula (Z ⁵ -1).

The compound represented by the formula (a1-1) is preferably a compound represented by the formula (a1-1-1) (hereinafter sometimes referred to as "compound (a1-1-1)"). The compound (a1-1-1) may be a tautomer thereof.

In the formula (a1-1-1), R ^1b to R ^4b independently of each other represent a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and a methylene group (-CH ₂ -) contained in the saturated hydrocarbon group Can be replaced by -O-, -CO-, -N(R ^11b )-, -OCO-, -(OOO-, -OCONH-, -NHCOO-, -CONH- or -NHCO-. However, adjacent -CH ₂ - will not be replaced by the same group at the same time, and the -CH ₂ - at the end will not be replaced. R ^1b and R ^2b may together form a ring containing a nitrogen atom, and R ^3b and R ^4b may together form a nitrogen-containing ring. The ring of atoms.

R ^5b and R ^6b independently of each other represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

R ^11b represents a hydrogen atom, a 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 ^1b to R ^4b and R ^11b include the same groups as the saturated hydrocarbon group having 1 to 20 carbon atoms in R ¹ to R ⁴ and R ¹⁰ .

The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be -O-, -CO-, -N(R ^11b )-, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH- or -NHCO- replacement. However, the adjacent -CH ₂ - will not be replaced by the same group at the same time, and the -CH ₂ - at the end will not be replaced.

The saturated hydrocarbon group in R ^1b to R ^4b may have a substituent, and examples of the substituent include an aromatic hydrocarbon group having 6 to 10 carbon atoms and a halogen atom.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl and toluene. Base, xylyl, mesityl, propylphenyl and butylphenyl.

Compound (a1-1-1) is preferably ~ R ^1b and R ^1b R ^4b in R ^2b, R ^3b and R ^4b are each the same saturated hydrocarbon group, preferably R ^1b and R ^2b, R ^3b and R ^4b are each linear The combination of a chain alkyl group is more preferably a combination of R ^1b and R ^2b , and R ^3b and R ^4b are each a linear alkyl group having 1 to 5 carbon atoms, and more preferably R ^1b and R ^2b , R ^3b and R. Each of ^{4b is} selected from a combination of two of a methyl group, an ethyl group, a propyl group, and a butyl group.

Examples of the ring formed by R ^1b and R ^2b and the ring formed by R ^3b and R ^4b include the following rings.

Examples of the alkyl group having 1 to 6 carbon atoms in R ^5b and R ^6b include an alkyl group having 1 to 6 carbon atoms in the above-exemplified alkyl group. Among them, as R ^5b and R ^6b , a hydrogen atom is preferred.

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

In addition, the compound represented by the formula (a1-1) is preferably a compound represented by the following formula (a1-1-2) (hereinafter sometimes referred to as "compound (a1-1-2)"). The compound (a1-1-2) may be a tautomer thereof.

In the formula (a1-1-2), R ^1c and R ^4c independently of each other represent an alkyl group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms or an alkylsulfonyl group having 1 to 4 carbon atoms.醯基.

p and q independently represent an integer of 0 to 5. When p is 2 or more, a plurality of R ^1c may be the same or different, and when q is 2 or more, a plurality of R ^4c may be the same or different.

R ^2c and R ^3c independently of each other represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be -O- , -CO-, -N(R ^11c )-, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH- or -NHCO-. However, the adjacent -CH ₂ - will not be replaced by the same group at the same time, and the -CH ₂ - at the end will not be replaced.

R ^1c and R ^2c may together form a ring containing a nitrogen atom, and R ^3c and R ^4c may together form a ring containing a nitrogen atom.

R ^5c and R ^6c independently of each other represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

R ^11c 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 alkyl group having 1 to 4 carbon atoms in R ^1c and R ^4c include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and a t-butyl group.

Examples of the alkylsulfanyl group having 1 to 4 carbon atoms in R ^1c and R ^4c include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, a butylsulfanyl group, and an isopropyl group. Sulfuryl group and the like.

Examples of the alkylsulfonyl group having 1 to 4 carbon atoms in R ^1c and R ^4c include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, and an isopropyl group. Sulfonyl and the like.

Among them, R ^1c and R ^{4c are} preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group.

p and q are preferably an integer of 0 to 2, preferably 1 or 2.

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms in R ^2c , R ^3c and R ^11c include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group and a decyl group. a linear alkyl group such as a decyl group, a dodecyl group, a hexadecyl group or an eicosyl group; a branched chain alkyl group such as an isopropyl group, an isobutyl group, an isopentyl group, a neopentyl group or a 2-ethylhexyl group; An alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group or a tricyclodecyl group. The monovalent saturated hydrocarbon group of R ^2c , R ^3c and R ^11c is more preferably a carbon number of 1 to 15, more preferably a carbon number of 1 to 10, still more preferably a carbon number of 1 to 6.

The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be -O-, -CO-, -N(R ^11c )-, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH- or -NHCO- replacement. However, the adjacent -CH ₂ - will not be replaced by the same group at the same time, and in addition, the terminal -CH ₂ - will not be replaced.

The saturated hydrocarbon group in R ^2c and R ^3c may have a substituent, and examples of the substituent include a halogen atom or an aromatic hydrocarbon group having 6 to 10 carbon atoms.

Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include a phenyl group, a tolyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group.

Examples of the alkyl group having 1 to 6 carbon atoms in R ^5c and R ^6c include an alkyl group having 1 to 6 carbon atoms in the above-exemplified alkyl group. Among them, as R ^5c and R ^6c , a hydrogen atom is preferred.

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

The compound (a1) is, for example, a compound represented by the formula (I-1) to the formula (I-25). In the formula (I-1) to the formula (I-25), R ⁴⁰ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched chain alkyl group having 6 to 12 carbon atoms, more preferably Ground represents 2-ethylhexyl.

Among the above compounds, a compound represented by the formula (I-18) to the formula (I-22) is preferred, and a compound represented by the formula (I-18), the formula (I-19) or the formula (I-21) is more preferable. The compound is more preferably a compound represented by the formula (I-19).

1-1-2. Squaric acid compound

The compound (a) of the present invention is preferably a squaraine compound (a2), and more preferably a compound represented by the following formula (a2-1).

In the formula (a2-1), R ^a1 to R ^a4 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a carbon number 6 to 20 aromatic hydrocarbon group which may have a substituent, or a saturated hydrocarbon group having 1 to 20 carbon atoms. R ^a1 and R ^a5 , R ^a2 and R ^a6 , R ^a3 and R ^a7 , R ^a4 and R ^a8 each may form a ring together with the carbon atom to which they are bonded, R ^a1 and R ^a9 , R ^a2 and R ^a10 , R ^a3 and R ^a11 , R ^a4 and R ^a12 may each form a ring together with a nitrogen atom and a carbon atom to which they are bonded.

R ^a5 to R ^a8 independently of each other represent a hydrogen atom, a hydroxyl group, a -SH group, a -CF ₃ group or -NHCO-R ^a23 .

R ^a9 to R ^a12 independently of each other represent an aromatic hydrocarbon group which may have a substituent, a saturated hydrocarbon group having 4 to 20 carbon atoms which may have a substituent, or an unsaturated aliphatic hydrocarbon group having 4 to 20 carbon atoms which may have a substituent. The methylene group constituting the saturated hydrocarbon group or the unsaturated aliphatic hydrocarbon group may be replaced with an oxygen atom, a sulfur atom, -N(R ^a24 )-, a sulfonyl group, or a carbonyl group. Further, R ^a9 and R ^a10 , R ^a11 and R ^a12 may form a ring together with the nitrogen atom to which they are bonded.

R ^a23 represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and the methylene group constituting the monovalent saturated hydrocarbon group may be replaced with an oxygen atom, a sulfur atom, -N(R ^a25 )-, a sulfonyl group or Carbonyl. However, the adjacent methylene groups are not replaced by the same group at the same time, and the methylene group at the end is not replaced.

R ^a24 and R ^a25 independently of each other represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms. ]

In the formula (a2-1), examples of the halogen atom in R ^a1 to R ^a4 include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

In the formula (a2-1), the aromatic hydrocarbon group represented by R ^a1 to R ^a4 is preferably a carbon number of 6 to 20, and more preferably a carbon number of 6 to 10.

In addition, examples of the substituent which the aromatic hydrocarbon group represented by R ^a1 to R ^a4 may have include an alkenyl group having 1 to 6 carbon atoms such as a vinyl group, a propenyl group, a butenyl group, a pentenyl group or a hexenyl group; Alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group or a hexyloxy group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; An alkyl group having 1 to 6 carbon atoms substituted with a fluorine atom such as a fluoromethyl group.

Examples of the aromatic hydrocarbon group of R ^a1 to R ^a4 include an aryl group such as a phenyl group, a tolyl group, a xylyl group, a mesityl group, a cumyl group, a biphenyl group, a naphthyl group, an anthranyl group, and a phenanthryl group; An arylalkyl group such as a phenylethyl group or a phenylbutyl group; an aryloxy group such as a phenoxy group; and the like.

The saturated hydrocarbon group having 1 to 20 carbon atoms in R ^a1 to R ^a4 and R ^a23 to R ^a25 is preferably a carbon number of 1 to 12, more preferably a carbon number of 1 to 10, still more preferably a carbon number of 1 to 8, more preferably The carbon number is 1~7. Specific examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a decyl group, a dodecyl group, a hexadecyl group, and a eicosyl group. a linear alkyl group having 1 to 20 carbon atoms; isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, 1-ethylpentyl, and 2-ethylhexyl a branched chain alkyl group having 3 to 20 carbon atoms; an alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and a tricyclodecyl group.

The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^a23 may have a substituent, and examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom; a cyano group; a nitro group; an aminomethyl fluorenyl group; Sulfhydryl; hydroxyl; amine and the like.

Examples of the group in which the methylene group constituting the monovalent saturated hydrocarbon group is replaced by an oxygen atom include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a secondary group. An alkoxy group such as a butoxy group, a tert-butoxy group or a pentyloxy group.

In addition, examples of the group in which the methylene group constituting the monovalent saturated hydrocarbon group is replaced by an oxygen atom and a carbonyl group include an alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group or a propoxycarbonyl group; An alkylcarbonyloxy group such as a decyloxy group; a group having an ester bond such as an arylcarbonyloxy group such as a benzyl methoxy group.

Further, examples of the group in which the methylene group constituting the monovalent saturated hydrocarbon group is replaced by -N(R ^a24 )- or -N(R ^a25 )- and a carbonyl group may, for example, be an N-methylaminocarbamyl group. N-ethylaminomethylindenyl, N-propylaminocarbamimidyl, N-isopropylaminomethylguanidinyl, N-butylaminomethylguanidinyl, N-isobutylaminocarbamidine , N-sec-butylaminomethylhydrazine, N-tert-butylaminomethylguanidinyl, N-pentylaminomethylguanidinyl, N-(1-ethylpropyl)aminocarbamidine N-substituted aminomethyl indenyl group such as N-(1,1-dimethylpropyl)aminocarbazinyl group; N,N-dimethylaminocarbamyl, N,N-ethyl Methylaminomethylmercapto, N,N-diethylaminocarbamyl, N,N-propylmethylaminocarbamimidyl, N,N-isopropylmethylaminocarbamyl, N,N-tert-butylmethylaminocarbamimidyl, N,N-butylethylaminocarbamimidyl, N,N-bis(1-methylpropyl)aminocarbamyl, N,N An N,N-2 substituted aminomethyl fluorenyl group such as a heptylmethylaminocarbamyl group or an N,N-bis(2-ethylhexyl)aminocarbenyl group.

The group in which the methylene group constituting the monovalent saturated hydrocarbon group is replaced by a sulfonyl group and -N(R ^a24 )- or -N(R ^a25 )- includes an N-methylamine sulfonyl group. N-ethylamine sulfonyl, N-propylamine sulfonyl, N-isopropylamine sulfonyl, N-butylamine sulfonyl, N-sec-butylamine sulfonyl, N- Tert-butylamine sulfonyl, N-pentylamine sulfonyl, N-(1-ethylpropyl)amine sulfonyl, N-cyclopentylamine sulfonyl, N-hexylamine sulfonyl N-substituted sulfonyl group such as N-(1,3-dimethylbutyl)amine sulfonyl group; N,N-dimethylamine sulfonyl group, N,N-ethylmethylamine sulfonate N,N-N,N-N-propylmethylaminesulfonyl, N,N-tert-butylmethylaminesulfonyl, N,N-bis(2-ethylhexyl)aminesulfonyl, etc. 2 substituted amine sulfonyl and the like.

Examples of the group in which the methylene group constituting the monovalent saturated hydrocarbon group is replaced by -N(R ^a24 )- or -N(R ^a25 )- may, for example, be an N-methylamino group or an N-ethylamino group. N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-sec-butylamino, N-tert-butylamino, N- Amylamino, N-(1-ethylpropyl)amino, N-(1,1-dimethylpropyl)amino, N-(1,2-dimethylpropyl)amino N-alkylamino group such as methylhexyl)amino, N-(1,1,2,2-tetramethylbutyl)amine; N,N-dimethylamino, N,N-ethyl Methylamino, N,N-diethylamino, N,N-propylmethylamino, N,N-isopropylmethylamino, N,N-tert-butylmethylamino, N , N-butylethylamino, N,N-bis(1-methylpropyl)amino, N,N-heptylmethylamino, N,N-bis(2-ethylhexyl)amine N,N-dialkylamino group; N-methylaminomethyl, N-ethylaminomethyl, N-propylaminomethyl, N-isopropylaminomethyl, N -butylaminomethyl, N-isobutylaminomethyl, N-sec-butylaminomethyl, N-tert-butylaminomethyl, N-pentylaminomethyl, N -(1-ethylpropyl)aminomethyl, N-(1,1-dimethylpropyl N-alkylaminomethyl group such as aminomethyl; N,N-dimethylaminomethyl, N,N-ethylmethylaminomethyl, N,N-diethylamino N,N-propylmethylaminomethyl, N,N-isopropylmethylaminomethyl, N,N-tert-butylmethylaminomethyl, N,N-butylethyl Aminomethyl, N,N-bis(1-methylpropyl)aminomethyl, N,N-heptylmethylaminomethyl, N,N-bis(2-ethylhexyl)amine An N,N-dialkylaminomethyl group such as a methyl group.

Examples of the ring formed by the carbon atom to which R ^a1 and R ^a5 , R ^a2 and R ^a6 , R ^a3 and R ^a7 , and R ^a4 and R ^a8 are bonded to each other include a structure represented by the following formula. In the formula, R ^A1 represents the same group as R ^a1 to R ^a4 , R ^A2 represents the same group as R ^a5 to R ^a8 , and R ^A3 represents the same group as R ^a9 to R ^a12 . * indicates the bonding end.

Examples of the ring formed by the nitrogen atom and the carbon atom to which R ^a1 and R ^a9 , R ^a2 and R ^a10 , R ^a3 and R ^a11 , and R ^a4 and R ^a12 are bonded to each other include a structure represented by the following formula: . In the formula, R ^A1 represents the same group as R ^a1 to R ^a4 , R ^A2 represents the same group as R ^a5 to R ^a8 , and R ^A3 represents the same group as R ^a9 to R ^a12 . * indicates the bonding end.

The aromatic hydrocarbon group which may have a substituent in R ^a9 to R ^a12 is preferably a carbon number of 6 or more, more preferably a carbon number of 8 or more, preferably a carbon number of 18 or less, and more preferably a carbon number of 15 or less. Examples of the aromatic hydrocarbon group represented by R ^a9 to R ^a12 include an aryl group having 6 to 12 carbon atoms such as a phenyl group, a tolyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group; An aralkyl group having 7 to 12 carbon atoms such as a benzyl group, a phenylethyl group or a phenylbutyl group. Further, as the aryl group, a phenyl group is particularly preferable, and as the aralkyl group, a benzyl group is particularly preferable.

The aromatic hydrocarbon group represented by R ^a9 to R ^a12 may have a substituent, and examples of the substituent include an alkenyl group having 1 to 5 carbon atoms such as a vinyl group.

Further, in the aryl group, it is preferred to have a substituent at the ortho position of the bonding terminal, and in the aralkyl group, it is preferred to have a substituent at the ortho position of the alkylene group. Examples of the aromatic hydrocarbon group which may have a substituent of R ^a9 to R ^a12 include a group represented by the following formula. Where * represents the bond end.

Examples of the saturated hydrocarbon group having 4 to 20 carbon atoms in R ^a9 to R ^a12 include a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a decyl group, a dodecyl group, and a hexadecyl group. And a linear alkyl group such as an eicosyl group; or a branched chain alkyl group such as 2-ethylhexyl. Further, examples of the monovalent unsaturated aliphatic hydrocarbon group having 4 to 20 carbon atoms in R ^a9 to R ^a12 include a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, and an anthracene group. A linear alkenyl group such as an alkenyl group, a nonenyl group, a dodecenyl group, a hexadecenyl group, or an eicosyl group.

The saturated hydrocarbon group having 4 to 20 carbon atoms in R ^a9 to R ^a12 may have a substituent, and examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom; a cyano group; a nitro group; and an aminomethyl fluorenyl group. Aminesulfonyl; hydroxyl; amine and the like.

Examples of the ring formed by R ^a9 and R ^a10 , R ^a11 and R ^a12 together with the nitrogen atom to which they are bonded include a structure represented by the following formula.

Examples of the aralkyl group having 7 to 10 carbon atoms in R ^a24 and R ^a25 include a benzyl group, a phenylethyl group, and a phenylbutyl group.

Among them, in the formula (a2-1), as R ^a1 to R ^a4 , a hydrogen atom is preferred.

R ^a5 to R ^{a8 are} preferably a hydrogen atom, a hydroxyl group or -NHCO-R ^a23 , more preferably a hydrogen atom or a hydroxyl group, and still more preferably a hydrogen atom.

R ^a9 to R ^a12 are preferably an aromatic hydrocarbon group having 8 to 20 carbon atoms which may have a substituent or a saturated hydrocarbon group having 4 to 20 carbon atoms which may have a substituent, and more preferably a carbon number which may have a substituent a monovalent aromatic hydrocarbon group of 4 to 20.

R ^a23 is preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, more preferably a saturated hydrocarbon group having 1 to 8 carbon atoms, and still more preferably a saturated hydrocarbon group having 1 to 4 carbon atoms.

R ^a24 and R ^a25 are each preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, more preferably a saturated hydrocarbon group having 1 to 8 carbon atoms, and still more preferably a saturated hydrocarbon group having 1 to 4 carbon atoms.

In addition, examples of the group represented by the following formulas (x-1) and (x-2) include groups represented by the formula (A1-1) to the formula (A1-8).

Further, in these formulas, * represents the bonding end, and >N-* may be >N ⁺ =*.

In addition, examples of the groups represented by the formulae (x-1) and (x-2) include, for example, the groups represented by the formulae (A1-1) to (A1-8). The groups represented by the formulae (A2-1) to (A2-7) are given. * indicates the bonding end, >N-* can be >N ⁺ =*.

In Tables 1 to 4, as a specific example of the compound represented by the formula (a2-1), the compound (AI-1) to the compound (AI-97) is listed based on the following formula (AI-a), but it is not Limited to this.

Further, in the formula (AI-a) and Tables 1 to 4, R ^a1 to R ^a8 are respectively synonymous with R ^a1 to R ^a8 in the above formula (a2-1), and X ^a1 and X ^a2 respectively mean a formula ( a group represented by x-1) and (x-2).

In addition, in Tables 1 to 4, (A1-1) to (A1-8) and (A2-1) to (A2-7) mean that the equations (A1-1) to (A1-8) are respectively equivalent. a group represented by the formula (A2-1) to the formula (A2-7). In the formula (x-1) and the formula (x-2), * represents a bonding end, and >N-* may be >N ⁺ =*. Furthermore, in Tables 1-4, NHCO-EHC means:

The group shown. * indicates the bonding end.

From the viewpoint of availability of raw materials, the compound (AI-16) to the compound (AI-30) is more preferable, and among them, the compound (AI-16), the compound (AI-17) and the compound (AI-22) are further preferable.

1-2. Anion (b)

The anion (b) is an anion having at least one element selected from the group consisting of tungsten, molybdenum, rhenium, and phosphorus, and oxygen as an essential element.

As the anion, an anionic compound containing a heteropoly acid or a homopoly acid containing tungsten as an essential element is preferable, and an anion of a phosphotungstic acid, a tungstic acid, and a tungsten-based polyacid is more preferable.

Examples of the anion of the heteropoly acid or the homopoly acid containing tungsten as an essential element include Keggin-type phosphotungstic acid ion α-[PW ₁₂ O ₄₀ ] ^3- , Dawson-type phosphotungstic acid ion α-[P ₂ W ₁₈ O ₆₂ ] ^6- , β-[P ₂ W ₁₈ O ₆₂ ] ^6- , Keggin-type lanthanum tungstate ion α-[SiW ₁₂ O ₄₀ ] ^4- , β-[SiW ₁₂ O ₄₀ ] ^4- , γ- [SiW ₁₂ O ₄₀ ] ^4- Further, as another example, [P ₂ W ₁₇ O ₆₁ ] ¹⁰ , [P ₂ W ₁₅ O ₅₆ ] ^12- , [H ₂ P ₂ W ₁₂ O ₄₈ ^12- , [NaP ₅ W ₃₀ O ₁₁₀ ] ^14- , α-[SiW ₉ O ₃₄ ] ^10- , γ-[SiW ₁₀ O ₃₆ ] ^8- , α-[SiW ₁₁ O ₃₉ ] ^8- , β- [SiW ₁₁ O ₃₉ ] ^8- , [W ₆ O ₁₉ ] ^2- , [W ₁₀ O ₃₂ ] ^4- , WO ₄ ^2-, and the like. Among them, a Keggin-type phosphotungstic acid ion α-[PW ₁₂ O ₄₀ ] ^{3- is} particularly preferable.

1-3. Cation (c)

The cation (c) is a cation containing an alkaline earth metal, and is preferably at least one selected from the group consisting of a magnesium cation, a calcium cation, a phosphonium cation, and a phosphonium cation, and more preferably a calcium cation or a phosphonium cation. These may be derived from a halogenated alkaline earth metal which can be precipitated after formation of a target, and the halogenated alkaline earth metal may be magnesium chloride, calcium chloride, barium chloride, barium chloride or the like.

In the case where the compound of the present invention is A [compound (a)] ^{a + b -} ‧ B [anion (b)] ^{c -} ‧ C [cation (c)] ^{d +} , the charge balance preferably satisfies Aa ⁽⁺⁾ = The relationship of Bc ^(-) and Ab ^(-) = Cd ⁽⁺⁾ is also preferably such that the relationship of Bc ^(-) = Cd ⁽⁺⁾ is further satisfied. The total number of charges of Aa ⁽⁺⁾ , Bc ^(-) , Ab ^(-) , and Cd ⁽⁺⁾ is preferably an even multiple, and the total of Aa ⁽⁺⁾ , Bc ^(-) , Ab ^(-) , and Cd ⁽⁺⁾ More preferably, the number of charges is 6, 8, 12, 16, 18, 24 or 36, further preferably 6, 8, or 12.

A is preferably an even multiple, more preferably 6, 8, 12, 16, 18, 24 or 36, further preferably 6, 8, or 12.

a represents a monovalent positive charge, and b represents a monovalent negative charge.

B is preferably an even multiple, more preferably 2 or 4, still more preferably 2.

c is preferably 3, 4 or 6.

C is preferably 3, 4 or 6.

d is preferably an even multiple, and more preferably 2.

1-4. An illustration of a compound containing a xanthene compound

The compound containing the compound (a), that is, the xanthene compound, the above anion (b), and the above cation (c) is exemplified below.

1-5. An illustration of a compound containing a squaraine compound

The compound containing the compound (a), a squaraine compound, the above anion (b), and the above cation (c) is exemplified below.

The following Ra represents the group described below.

The compound of the present invention is preferably selected from the group consisting of the formula (Xa-1a) to the formula (Xa-1h), the formula (Xa-2a) to the formula (Xa-2h), the formula (Xa-3a) to the formula (Xa-3h), and the formula. (Xa-4a)~Formula (Xa-4h) and Formula (Xa-5a)~Formula (Xa-5h), preferably selected from the formula (SQ-1a)~Formula (SQ-1h), Formula (SQ-2a) ~Formula (SQ-2h), Formula (SQ-3a)~Formula (SQ-3h) and Formula (SQ-4a)~Formula (SQ-4h), more preferably selected From the formula (Xa-5a) to the formula (Xa-5h), further preferably the formula (Xa-5a).

The compounds of the invention can be used as colorants.

2. Colored curable resin composition

The present invention includes a colored curable resin composition containing a compound of the present invention (hereinafter sometimes referred to as a colorant (A1)), a resin (B), a polymerizable compound (C), and a polymerization initiator (D). ).

Two or more types of the coloring agent (A1) can be combined.

The content ratio of the coloring agent (A1) in the colorant is usually from 1 to 100% by mass, preferably from 3 to 100% by mass, more preferably from 3 to 70% by mass, even more preferably from 3 to 60% by mass.

In addition to the colorant (A1), a dye or pigment may be contained as the colorant (A2).

Examples of the dye of the coloring agent (A2) include a solvent index (Solvent), acidity, basicity, and reactivity in the Colour Index (published by The Society of Dyers and Colourists). A well-known dye described in Direct, Disperse, or Vat compound and dyeing note (color dyeing company). Further, examples of the chemical structure include an azo dye, an anthraquinone dye, a triphenylmethane dye, a xanthene dye, and a phthalocyanine dye. These dyes may be used in combination of two or more kinds.

Specifically, a dye having the following color index (C.I.) number can be cited. Can be enumerated: C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112 , 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184 , 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI active yellow 2, 76, 116; CI direct yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94 , 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; CI disperse yellow 51, 54, 76; CI solvent orange 2, 7, 11, 15, 26, 41, 54, 56, 99 CI oranges 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; CI Reactive Orange 16; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Solvent Red 24, 49 , 90, 91, 111, 11 8, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI acid red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289; CI Acid Violet 34, 102; CI Disperse Violet 26, 27; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI Acid Blue 25, 27, 40, 45, 78, 80, 112; CI Direct Blue 40; CI Disperse Blue 1, 14, 56, 60; CI Solvent Green 1, 3, 5, 28, 29, 32, 33; CI acid green 3, 5, 9, 25, 27, 28, 41; CI alkaline green 1; CI reduced green 1 and so on.

The pigment of the colorant (A2) is not particularly limited, and a known pigment can be used. For example, a pigment classified as a pigment in the excellent index (published by The Society of Dyers and Colourists) may be mentioned, and two or more kinds thereof may be combined.

Specifically, CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, Yellow pigments such as 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214; CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; CI Pigment Red 9, 97, 105, 122, 123, 144 Red pigments such as 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265; CI Pigment Blue 15, 15:3, 15:4, 15 : 6, 60 and other cyan pigments; CI pigment purple 1,19,23,29,32,36,38 and other purple pigments; CI pigment green 7,36,58 and other green pigments.

For the pigment, if necessary, rosin treatment, surface treatment using a pigment derivative into which an acidic group or a basic group is introduced, graft treatment on a pigment surface using a polymer compound, or the like, and sulfuric acid micronization may be used. The atomization treatment such as the method, or the organic solvent for removing impurities, the washing treatment of water or the like, the removal treatment of the ionic impurities by an ion exchange method, or the like. Preferably, the particle size of the pigment is substantially uniform. The pigment is dispersed by a pigment dispersant, and a pigment dispersion liquid in a state of being uniformly dispersed in the pigment dispersant solution can be obtained. The pigments may be separately subjected to dispersion treatment, or may be subjected to dispersion treatment by mixing a plurality of types.

The pigment dispersing agent may, for example, be a surfactant, or the like, and may be a cationic, anionic, nonionic or amphoteric surfactant. Specifically, a surfactant such as a polyester-based, polyamine-based or acrylic-based surfactant can be given. These pigment dispersants may be used singly or in combination of two or more. In the case of the pigment dispersant, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), (made by Kyoeisha Chemical Co., Ltd.), (Trademark)( Manufactured by SFKA (registered trademark) (manufactured by BASF Corporation), (registered trademark) (Ajinomoto (manufactured by the company), Disperbyk (registered trademark) ( Company manufacturing) and so on.

In the case of using a pigment dispersant, the amount thereof is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less based on 100 parts by mass of the pigment. If the amount of the pigment dispersant used is within the above range, there is a tendency that a pigment dispersion liquid having a more uniform dispersion state can be obtained.

The content ratio of the coloring agent (A1) in the colored curable resin composition is usually 0.01% by mass or more and 70% by mass or less, preferably 0.1% by mass or more and 60% by mass or less, based on the total amount of the solid content. It is preferably 0.2% by mass or more and 60% by mass or less, and particularly preferably 0.3% by mass or more and 50% by mass or less. When the content of the colorant (A1) is within the above range, it is easier to obtain desired spectral and color concentrations. In the present specification, the "total amount of the solid component" means the total amount of the components obtained by removing the solvent from the colored curable resin composition of the present invention. The total amount of the solid components and the content of each component with respect to the solid components can be measured, for example, by a known analytical means such as liquid chromatography or gas chromatography.

When the coloring agent (A2) is further contained, the ratio of the amount of the coloring agent (A1) to the amount of the coloring agent (A2) used (coloring agent (A1) (solid content conversion) / coloring agent (A2) (solid) The component conversion)) is preferably 0.1 or more and 100 or less, more preferably 0.5 or more and 50 or less, further preferably 1 or more and 25 or less, particularly preferably 1 or more and 10 or less, and most preferably 2 or more and 6 or less.

<Resin (B)>

The resin (B) contained in the colored curable resin composition of the present invention is preferably an alkali-soluble resin, and more preferably an addition polymer having a structural unit derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides. . Examples of such a resin include the following resins [K1] to [K6].

Resin [K1]: at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic anhydride (a) (hereinafter sometimes referred to as "(a)"), and a cyclic ether structure having a carbon number of 2 to 4 and an alkene a copolymer of a monomer (b) which is an unsaturated bond (hereinafter sometimes referred to as "(b)");

Resin [K2]: (a), (b), and monomer (c) copolymerizable with (a) (however, unlike (a) and (b).) (hereinafter sometimes referred to as "(c) Copolymer

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

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

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

Resin [K6]: a resin obtained by reacting the copolymer of (a) with (b) and (c) and further reacting a carboxylic anhydride.

Examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid; unsaturated dicarboxylic acids such as maleic acid; and methyl-5. - a carboxyl-containing bicyclic ring such as norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene Unsaturated compound; An unsaturated carboxylic acid anhydride such as maleic anhydride; or an unsaturated acrylate having a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid.

Among them, acrylic acid, methacrylic acid, and maleic anhydride are preferred from the viewpoints of copolymerization reactivity and solubility of the obtained resin in an aqueous alkali solution.

(b) means a polymerization of a cyclic ether structure having a carbon number of 2 to 4 (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. Sex compounds. (b) is preferably a monomer having a cyclic ether structure of 2 to 4 carbon atoms and a (meth)acryloxy group. In the present specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The expressions "(meth)acrylinyl" and "(meth)acrylate" also mean the same meaning.

Examples of (b) include a monomer (b1) having an epoxyethyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), having an oxetanyl group and an ethylenically unsaturated bond. The monomer (b2) (hereinafter sometimes referred to as "(b2)"), and the monomer (b3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").

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

As (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferred. Specific examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, and (methyl). Β-ethyl glycidyl 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-double (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 and 2,4,6-tris(glycidoxymethyl)styrene .

Examples of (b1-2) include vinylcyclohexene monooxide and 1,2-epoxy-4-vinylcyclohexane (for example, (registered trademark) 2000; manufactured by Daicel Co., Ltd., 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, (registered trademark) A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, M100; manufactured by Daicel Co., Ltd.), a compound represented by the formula (1), and a compound represented by the formula (2).

In the formulae (1) and (2), R ^a and R ^b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group.

X ^a and X ^b each independently represents a single ^{bond, * - R c -, *} - R c -O -, * - R c -S- or * -R ^c -NH-.

R ^c represents an alkylene group having 1 to 6 carbon atoms.

* indicates the bonding end with O. ]

The compound represented by the formula (1) includes a compound represented by the formula (1-1) to the formula (1-15), and among them, the formula (1-1), the formula (1-3), and the formula are preferable. (1-5), a compound represented by the formula (1-7), the formula (1-9), and the formula (1-11) to the formula (1-15), more preferably a formula (1-1) or a formula (1) -7), a compound represented by the formula (1-9) and the formula (1-15).

The compound represented by the formula (2) includes a compound represented by the formula (2-1) to the formula (2-15), and among them, the formula (2-1), the formula (2-3), and the formula are preferable. (2-5), a compound represented by the formula (2-7), the formula (2-9), and the formula (2-11) to the formula (2-15), more preferably of the formula (2-1), the formula (2) -7), a compound represented by the formula (2-9) and the formula (2-15).

The compound represented by the formula (1) and the compound represented by the formula (2) may be used singly or in combination, and the compound represented by the formula (1) may be used in combination with the compound represented by the formula (2). When they are used in combination, the ratio of the compound represented by the formula (1) and the compound represented by the formula (2) (the compound represented by the formula (1): the compound represented by the formula (2)), on a molar basis, It is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, still more preferably 20:80 to 80:20.

As (b2), a monomer having an oxetanyl group and a (meth) acryloxy group is more preferable.

As (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloxy group is more preferable.

(b) is preferably (b1), and is excellent in storage stability of the colored curable resin composition, (b1), in order to further improve the reliability of heat resistance and chemical resistance of the obtained color filter. ) is preferably (b1-2).

Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, and t-butyl (meth)acrylate. , 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, Cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo [5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate (in the technical field) As a conventional name, it is called "dicyclopentanyl (meth) acrylate." In addition, it is sometimes called "tricyclodecyl (meth) acrylate".), tricyclo(meth) acrylate [5.2.1.0 ^{2 , 6} ]nonene-8-yl ester (in the technical field, as a conventional name, it is called "dicyclopentenyl (meth) acrylate"), (di) pentyloxyethyl (meth) acrylate, (a) Isobornyl acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, (meth) acrylate such as benzyl (meth) acrylate; a hydroxyl group-containing (meth) acrylate such as 2-hydroxyethyl acrylate or 2-hydroxypropyl (meth) acrylate; diethyl maleate, diethyl fumarate, diethyl itaconate, etc. Dicarboxylic acid diester; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]heptane- 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-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2 - alkene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-A Bicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]g 2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonyl Bicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6- a bicyclic unsaturated compound such as (cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaline Yttrium, N-succinimide-3-maleimide benzoate, N-amber succinimide-4-maleimide butyrate, N-succinimide -6-maleimide caproate, N-succinimide-3-maleimide propionate, di-carbonylimine such as N-(9-acridinyl)maleimide a compound; a vinyl-containing aromatic compound such as styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene or p-methoxystyrene; acrylonitrile, A a nitrile containing vinyl such as acrylonitrile; a halogenated hydrocarbon such as vinyl chloride or vinylidene chloride; a decylamine containing vinyl such as acrylamide or methacrylamide; an ester such as vinyl acetate; a diene such as an alkene, an isoprene or a 2,3-dimethyl-1,3-butadiene or the like.

Among these, a vinyl group-containing aromatic compound, a dicarbonylimine compound, and a bicyclic unsaturated compound are preferable from the viewpoint of copolymerization reactivity and heat resistance. Specifically, styrene, vinyl toluene, benzyl (meth)acrylate, tricyclo[5.1.02 ^2,6 ]decane-8-yl ester, N-phenyl malayan Amine, N-cyclohexylmaleimide, N-benzylmaleimide and bicyclo [2.2.1]hept-2-ene.

Examples of the carboxylic anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, and 3,4,5,6-tetrahydroortylene. Dicarboxylic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride. The amount of the carboxylic anhydride used is preferably 0.5 to 1 mol based on 1 mol of the amount of (a) used.

Examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer and (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2.6 Resin such as oxime ester/(meth)acrylic copolymer [K1]; glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate /styrene/(meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl ester /(meth)acrylic acid /N-cyclohexylmaleimide copolymer , 3,4-epoxytricyclo(5.sup.3-epoxy)[5.2.1.0 ^2.6 ]decyl ester/(meth)acrylic acid/vinyltoluene copolymer, 3-methyl-3-(methyl)propene oxime Resin such as methyl oxetane/(meth)acrylic acid/styrene copolymer [K2]; benzyl (meth) acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer a resin such as benzyl (meth)acrylate/tricyclodecyl (meth)acrylate/(meth)acrylic acid copolymer [K3]; glycidyl (meth)acrylate and benzyl (meth)acrylate /(Meth)acrylic acid copolymer addition resin, make (meth)acrylic acid glycidyl a resin obtained by adding an ester to a tricyclodecyl (meth) acrylate/styrene/(meth)acrylic acid copolymer, and a glycidyl (meth)acrylate and a tricyclodealkyl (meth)acrylate/( a resin such as a resin obtained by adding a benzyl methacrylate/(meth)acrylic acid copolymer [K4]; a (meth)acrylic acid and a tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate a resin obtained by reacting an ester copolymer, a resin such as a resin obtained by reacting a copolymer of (meth)acrylic acid and tricyclodecyl (meth)acrylate/styrene/glycidyl (meth)acrylate [K5] a resin obtained by reacting a resin obtained by reacting a copolymer of (meth)acrylic acid with tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate, and further reacting with tetrahydrophthalic anhydride Resin [K6].

The polystyrene-equivalent weight average molecular weight of the resin (B) is usually from 3,000 to 100,000, preferably from 5,000 to 50,000, more preferably from 5,000 to 35,000, still more preferably from 5,000 to 30,000, still more preferably from 6,000 to 25,000. When the molecular weight is within the above range, the coating film hardness is increased, the residual film ratio is also high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern tends to be improved.

The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably from 1.1 to 6, more preferably from 1.2 to 4, still more preferably from 1.3 to 3, still more preferably from 1.5 to 2.5.

The acid value (in terms of solid content) of the resin (B) is preferably from 20 to 170 mg-KOH/g, more preferably from 30 to 170 mg-KOH/g, wherein It is preferably 40 to 170 mg-KOH/g, preferably 50 to 170 mg-KOH/g, more preferably 150 mg-KOH/g or less, still more preferably 135 mg-KOH/g or less.

Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained, for example, by titration using a potassium hydroxide aqueous solution.

The content of the resin (B) is preferably 7 to 65% by mass, more preferably 10 to 60% by mass, and particularly preferably 13 to 60% by mass, and preferably 17 to 55% by mass, based on the total amount of the solid content. When the content of the resin (B) is within the above range, the formation of a colored pattern tends to be easy, and the resolution of the colored pattern and the residual film ratio tend to be improved.

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound which can be polymerized by an active radical and/or an acid generated by a polymerization initiator, and examples thereof include a polymerizable compound having an ethylenically unsaturated bond, and preferably have a (meth) acrylate structure. Compound. The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds, and more preferably a polymerizable compound having five to six ethylenically unsaturated bonds.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, and 2-ethylhexyl carbitol acrylate. 2-hydroxyethyl acrylate, N-vinylpyrrolidone, (a), (b) and (c) above. Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, and neopentyl glycol. Di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloxyethyl)ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate. Examples of the polymerizable compound having three or more ethylenically unsaturated bonds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and Pentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, pentaerythritol deca (meth) acrylate, four Pentaerythritol 九(meth) acrylate, tris(2-(methyl) propylene methoxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified Pentaerythritol hexa(meth) acrylate, propylene glycol modified pentaerythritol tetra(meth) acrylate, propylene glycol modified dipentaerythritol hexa (meth) acrylate, caprolactone modified pentaerythritol tetra (meth) acrylate and caprolactone Modified dipentaerythritol hexa(meth) acrylate.

Among these, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate are preferable.

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

The content of the polymerizable compound (C) in the colored curable resin composition of the present invention is usually 5 to 65% by mass, preferably 7 to 65% by mass, and more preferably 10 to 60% based on the total amount of the solid content. The mass % is more preferably 13 to 60% by mass, and particularly preferably 17 to 55% by mass. The content ratio of the resin (B) to the polymerizable compound (C) (resin (B): polymerizable compound (C)) is usually 20:80 to 80:20, preferably 35: by mass: 65~80:20. When the content of the polymerizable compound (C) is within the above range, there is a tendency that the residual film ratio at the time of formation of the colored pattern and the chemical resistance of the color filter are 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 by the action of light or heat, and a known polymerization initiator can be used.

Examples of the polymerization initiator (D) include an O-fluorenyl hydrazine compound, an alkyl phenyl ketone compound, a triazine compound, a mercaptophosphine oxide compound, and a biimidazole compound.

Examples of the O-indenyl ruthenium compound include N-benzylideneoxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imide and N-benzylideneoxy group. 1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-benzylideneoxy-1-(4-phenylsulfanylphenyl)-3- Cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzylidene)-9H-indazol-3-yl Ethyl-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxa) Cyclopentylmethoxy)benzylidene}-9H-indazol-3-yl]ethane-1-imine, N-ethyloxy-1-[9-ethyl-6-(2- Methyl benzhydryl)-9H-oxazol-3-yl]-3-cyclopentylpropane-1-imine and N-benzylideneoxy-1-[9-ethyl-6-(2 -Methylbenzylidene)-9H-indazol-3-yl]-3-cyclopentylpropan-1-one-2-imine. Commercial products such as Irgacure (registered trademark) OXE01, OXE02 (above, manufactured by BASF Corporation), and N-1919 (made by ADEKA Co., Ltd.) can be used. Among them, it is preferably selected from N-benzylideneoxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N- Benzamethyleneoxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine and N-benzylideneoxy-1-(4-phenylsulfanylbenzene) At least one of benzyl-3-cyclopentylpropan-1-one-2-imine, more preferably N-benzylideneoxy-1-(4-phenylsulfanylphenyl)octane- 1-keto-2-imine.

The alkyl phenyl ketone compound may, for example, be 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one or 2-dimethylamino-1- (4-morpholinophenyl)-2-benzylbutan-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4 -(4-morpholinyl)phenyl]butan-1-one. Commercial products such as Irgacure 369, 907, and 379 (above, manufactured by BASF Corporation) can be used.

An alkyl phenyl ketone compound, which may be 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy) Oligomers of phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α, --diethoxyacetophenone and benzoin dimethyl ketal.

Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine and 2,4-bis(trichloromethyl). - 6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperidin-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)ethylene Base]-1,3,5-triazine.

The fluorenylphosphine oxide compound is exemplified by 2,4,6-trimethylbenzimidyldiphenylphosphine oxide. Commercial products such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) can be used.

Specific examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis (2,3). -Dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, see JP-A-6-75372, JP-A-6-75373, etc.), 2, 2 '-Bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5' -tetrakis(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2, 2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, refer to Japanese Patent Publication No. Sho 48-38403, JP-A-Japan) Japanese Patent Publication No. 62-174204, etc., and an imidazole compound in which a phenyl group at the 4,4', 5, 5'-position is substituted with an alkoxycarbonyl group (for example, see JP-A-7-10913, etc.). Among them, preferred are compounds represented by the following formulas and mixtures thereof.

Examples of the other polymerization initiator include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutylene. Benzoin compounds such as ethers; benzophenone, methyl o-benzhydrylbenzoate, 4-phenylbenzophenone, 4-benzylidene-4'-methyldiphenyl sulfide a benzophenone compound such as 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone or 2,4,6-trimethylbenzophenone; 9,10- Anthraquinone compounds such as phenanthrenequinone, 2-ethylhydrazine, camphorquinone; 10-butyl-2-chloroacridone, benzophenone, methyl phenylglyoxylate, titanocene compound, and the like. These are preferably used in combination with a polymerization initiation aid (particularly an amine polymerization initiation aid) to be described later.

The content of the polymerization initiator (D) is usually 0.1 to 40 parts by mass, preferably 0.1 to 30 parts by mass, more preferably 1 to 1 part by mass based on 100 parts by mass of the total of the resin (B) and the polymerizable compound (C). 30 parts by mass, particularly preferably 1 to 20 parts by mass.

<Polymerization Initiative>

The polymerization initiation aid is a compound or a sensitizer for promoting polymerization of the polymerizable compound (C) which has been polymerized by the polymerization initiator (D). When the color-curable resin composition of the present invention contains a polymerization initiation aid, it is usually used in combination with a polymerization initiator (D).

Examples of the polymerization initiation aid include an amine polymerization initiation aid, an alkoxyfluorene polymerization initiation aid, a thioxanthone polymerization initiation aid, and a carboxylic acid polymerization initiation aid.

Examples of the amine-based polymerization initiation aid include alkanolamines such as triethanolamine, methyldiethanolamine, and triisopropanolamine; methyl 4-dimethylaminobenzoate and 4-dimethylaminobenzoic acid; Ethyl benzoate such as ethyl ester, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate or 2-ethylhexyl 4-dimethylaminobenzoate N,N-dimethyl-p-toluidine; 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-double (B The methylamino) benzophenone is preferably an alkylamino benzophenone such as 4,4'-bis(diethylamino)benzophenone. Among them, an alkylaminobenzophenone is preferred, and 4,4'-bis(diethylamino)benzophenone is preferred. Commercial products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used.

Examples of the alkoxy oxime-based polymerization initiator include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, and 2- Ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene and 2-ethyl-9,10-dibutoxyanthracene.

Examples of the thioxanthone-based polymerization initiation aid include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, and 2,4-dichlorothioxanthone. And 1-chloro-4-propoxythioxanthone.

Examples of the carboxylic acid polymerization initiation aid include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, and dimethyl group. Phenylthioalkylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylgan Amine acid, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthyloxyacetic acid.

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

<Solvent (E)>

The solvent (E) is not limited, and the solvent which is usually used in the field can be used singly or in combination of two or more kinds. Specific examples thereof include an ester solvent (a solvent containing -COO- in the molecule and a solvent containing no -O-), an ether solvent (a solvent containing -O- in the molecule, a solvent containing no -COO-), and an ether ester solvent (in the case of a solvent containing -COO- and -O- in the molecule), a ketone solvent (-CO-, a solvent containing no -COO- in the molecule), an alcohol solvent (containing OH in the molecule, not containing -O-, - A solvent for CO- and -COO-), an aromatic hydrocarbon solvent, a guanamine solvent, and dimethyl hydrazine.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, and C. Butyl acrylate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate, 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, and diethylene glycol single. Ethyl 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-methyl Oxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, Diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether and methyl anisole.

As the ether ester solvent, methyl methoxyacetate, A Ethyl oxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, 3-B Methyl oxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, 2-B Methyl oxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropanoate, ethyl 2-ethoxy-2-methylpropionate, 3-methyl Oxybutyl butyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate , ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether Acetate.

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

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

Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and 1,3,5-trimethylbenzene.

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

These solvents may be used in combination of two or more kinds.

Among the above-mentioned solvents, an organic solvent having a boiling point of 120 ° C or more and 210 ° C or less at 1 atm (atmospheric pressure) is preferable from the viewpoint of coatability and drying property. Among them, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, and ethylene glycol monomethyl are preferred. Ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 3-methoxybutyl acetate, 3-methoxy-1-butanol, 4 -hydroxy-4-methyl-2-pentanone, N,N-dimethylformamide and N-methylpyrrolidone, more preferably propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethylene glycol Monobutyl ether, dipropylene glycol methyl ether acetate, ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol, ethyl 3-ethoxypropionate, N,N-dimethylformamide and N-methylpyrrolidone.

The content of the solvent (E) is usually 70 to 95% by mass, preferably 75 to 92% by mass, and more preferably 75 to 90% by mass based on the total amount of the colored curable resin composition. When the content of the solvent (E) is in the above range, the flatness at the time of coating becomes good, and the color density is not insufficient when the color filter is formed, so that the display characteristics tend to be good.

<leveling agent>

Examples of the leveling agent include an organic lanthanoid surfactant, a fluorine-based surfactant, and an organic lanthanoid surfactant having a fluorine atom. These may have a polymerizable group in the side chain.

Examples of the organic oxime-based surfactant include surfactants having a decane bond in the molecule. Specifically, it can be enumerated DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (manufactured by Toray-Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400 , TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 ( ‧ ‧ ‧ Contract company made) and so on.

The fluorine-based surfactant may, for example, be a surfactant having a fluorocarbon chain in the molecule. Specifically, it can be enumerated (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), (registered trademark) EF301, EF303, EF351, EF352 (Mitsubishi Electronic Manufacturing Co., Ltd.), (registered trademark) S381, S382, SC101, SC105 (made by Asahi Glass Co., Ltd.) and E5844 (( ) Institute of manufacturing).

The organic ruthenium-based surfactant having a fluorine atom includes a surfactant having a decane bond and a fluorocarbon chain in the molecule. Specifically, it can be enumerated (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

The content of the leveling agent is usually 0.0005 mass% or more and 0.6 mass% or less, preferably 0.001 mass% or more and 0.5 mass% or less, and more preferably 0.001 mass% or more, based on the total amount of the colored curable resin composition. 0.2% by mass or less, more preferably 0.002% by mass or more and 0.1% by mass or less, and particularly preferably 0.005% by mass or more and 0.07% by mass or less. When the content of the leveling agent is within the above range, the flatness of the color filter can be improved.

<Other ingredients>

The colored curable resin composition of the present invention may contain a filler, another polymer compound, an adhesion promoter, an antioxidant, or the like, if necessary. Light stabilizers, chain transfer agents and the like which are well known in the art.

<Method for Producing Colored Curable Resin Composition>

The colored curable resin composition of the present invention can be added, for example, by a compound (colorant (A1)), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E), and if necessary. The leveling agent, the polymerization initiator and other components are prepared by mixing. In addition to the colorant (A1), a coloring agent (A2) such as a pigment or a dye can be further mixed. The pigment is preferably used in a state in which it is mixed with a part or the whole of the solvent (E), and is dispersed in a bead mill or the like until the average particle diameter of the pigment is 0.2 μm or less. In this case, a part or all of the above-mentioned pigment dispersant and resin (B) may be blended as needed.

It is preferable to filter the mixed colored curable resin composition using a filter having a pore diameter of about 0.01 to 10 μm.

<Method of Manufacturing Color Filter>

A method of producing a colored pattern by the colored curable resin composition of the present invention includes a photolithography method, an inkjet method, a printing method, and the like. Among them, photolithography is preferred. The photolithography method is a method in which a colored curable resin composition is applied onto a substrate, dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the photolithography method, a coloring coating film which is a cured product of the coloring composition layer can be formed by using a photomask and/or no development at the time of exposure. The colored pattern and the colored coating film thus formed are the color filters of the present invention.

The film thickness of the produced color filter can be appropriately adjusted depending on the purpose, use, and the like, and is usually 0.1 to 30 μm, preferably 0.1 to 20 μm, more preferably Choose 0.5~6μm.

As the substrate, a glass plate, a resin plate, a crucible, or a product such as an aluminum, silver, silver/copper/palladium alloy film or the like can be formed on the substrate. Additional color filter layers, resin layers, transistors, circuits, and the like can be formed on these substrates.

The formation of each color pixel by photolithography can be carried out under known or conventional devices and conditions. For example, it can be produced as follows.

First, the colored curable resin composition is applied onto a substrate, and dried by heating (prebaking) and/or drying under reduced pressure to remove a volatile component such as a solvent and dry it to obtain a smooth colored composition layer. Examples of the coating method include a spin coating method, a slit coating method, and a slit and spin coating method.

Next, the colored composition layer is exposed through a photomask for forming a colored pattern of the target. Since the parallel light rays can be uniformly irradiated to the entire exposed surface, the correct alignment of the photomask and the substrate on which the colored composition layer is formed is performed. Therefore, an exposure apparatus such as a mask aligner and a stepper is preferably used. The colored composition layer after exposure is developed in contact with the developer to form a colored pattern on the substrate. By development, the unexposed portion of the colored composition layer is dissolved in the developer to be removed. As the developer, an aqueous solution of a basic compound such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate or tetramethylammonium hydroxide is preferred. The developing method may be any one of a spin coating immersion method, a dipping method, and a spray method. Further, the substrate can be inclined at an arbitrary angle during development. It is preferred to carry out water washing after development.

Preferably, the obtained colored pattern is further post-baked Baked. The color filter having the colored pattern and the colored coating film thus obtained can be further subjected to a surface coating treatment in order to impart various characteristics.

The color filter formed of the colored curable resin composition of the present invention can be used as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper, or the like) and a solid-state image sensor.

Example

The invention will now be more specifically described by way of examples. In the examples, the content and the % and the amount of the use amount are shown as the mass basis unless otherwise specified.

[Example 1]

400 parts of methanol was added to 5.0 parts of the compound represented by the formula (1-1), and the mixture was stirred at 20 to 30 ° C for 1 hour to obtain a solution. 400 parts of ion-exchanged water was added to the solution, and the mixture was stirred for 2 hours to obtain a solution (1-1A). On the other hand, 28.8 parts of ion-exchanged water was added to 9.6 parts of phosphorus 12 tungstic acid trihydrogen, and the mixture was stirred at 20 ° C to 30 ° C for 1 hour, and then 28.8 parts of methanol was added thereto, and the mixture was stirred for 2 hours to obtain a solution (1). 1B). To the solution (1-1A), a solution (1-1B) and 1.0 part of cesium chloride were added, and the mixture was stirred at 20 to 30 ° C for 24 hours. The resulting precipitate was collected by filtration, washed twice with 200 parts of ion-exchanged water, and then washed twice with 200 parts of methanol. The filtered crystals were dried at 60 ° C for 24 hours to obtain 6.3 parts of the compound represented by the formula (1-1P) (the compound represented by the above formula (1-1P) and the compound represented by the above formula (Xa-5a). Compounds are synonymous).

[Synthesis of Resin]

In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, an appropriate amount of nitrogen was allowed to flow into a nitrogen atmosphere, and 100 parts of propylene glycol monomethyl ether acetate was placed, and the mixture was heated to 85 ° C with stirring. Next, a drop pump was used in the flask for about 5 hours to make 19 parts of methacrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and acrylic acid. a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-9-yl ester (content ratio: 50:50 by molar ratio) (trade name "E-DCPA", Daicel 株式会社) Manufactured 171 parts of a solution dissolved in 40 parts of propylene glycol monomethyl ether acetate. On the other hand, an additional drip pump was used to drip into the flask over a period of about 5 hours to dissolve 26 parts of the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) in propylene glycol monomethyl. A solution of 120 parts of ether acetate. After completion of the dropwise addition of the polymerization initiator, the mixture was kept at the same temperature for about 3 hours, and then cooled to room temperature to obtain a solution of a copolymer having a solid content of 43.5% and a solution of the resin (B-1). The obtained resin (B-1) had a weight average molecular weight of 8,000, a molecular weight distribution of 1.98, and an acid value of 53 mg-KOH/g in terms of solid content.

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

Device: HLC-8120GPC (manufactured by Tosoh Corporation)

Column: TSK-GELG2000HXL

Column temperature: 40 ° C

Solvent: THF

Flow rate: 1.0mL/min

Solid concentration of the tested liquid: 0.001~0.01% by mass

Injection volume: 50μL

Detector: RI

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

The polystyrene-converted weight average molecular weight and number average obtained above The ratio of the sub-quantities (Mw/Mn) is taken as the molecular weight distribution.

[Preparation of Colored Curable Resin Composition]

Example 2

Compound (A1): 0.8 parts of a compound represented by the formula (1-1P); alkali-soluble resin (B): resin (B-1) (in terms of solid content) 50 parts; polymerizable compound (C): dipentaerythritol Acrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts; polymerization initiator (D): N-benzylideneoxy-1-(4-phenylsulfanylphenyl) octyl Alkan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation; O-mercaptopurine compound) 10 parts; solvent (E): 1-methyl-2-pyrrolidone 700 parts; And leveling agent (F): (registered trademark) F554 (manufactured by DIC Corporation) was mixed in 0.1 part to obtain a colored curable resin composition.

Comparative example 1

Dye (A1): 0.6 parts of the compound represented by the formula (1-1); alkali-soluble resin (B): resin (B-1) (in terms of solid content) 50 parts; polymerizable compound (C): dipentaerythritol Acrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts; polymerization initiator (D): N-benzylideneoxy-1-(4-phenylsulfanylphenyl) octyl Alkan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation; O-mercaptopurine compound) 10 parts; solvent (E): propylene glycol monomethyl ether acetate 700 parts; And leveling agent (F): (registered trademark) F554 (manufactured by DIC Corporation) was mixed in 0.1 part to obtain a colored curable resin composition.

[Formation of patterns]

On a 2 inch square glass substrate ( The colored curable resin composition was applied by spin coating on XG; manufactured by Corning Co., Ltd., and then prebaked at 100 ° C for 3 minutes to obtain a composition layer. After cooling, the distance between the glass substrate on which the composition layer was formed and the quartz glass photomask was 100 μm, and an exposure machine (TME-150RSK; (manufactured by Kyrgyzstan Co., Ltd.) Light irradiation was performed at an exposure amount (365 nm basis) of 150 mJ/cm 2 in an air atmosphere. As the photomask, a photomask in which a line pattern of 100 μm line and gap was formed was used. After the light irradiation, the coating film was immersed and developed in an aqueous developing solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23 ° C for 80 seconds, washed with water, and then subjected to an oven at 220 ° C. After a minute of baking, a pattern was obtained.

[Heat resistance evaluation]

The coating film of the colored curable resin composition was heated at 230 ° C for 20 minutes, and the color difference (ΔEab*) before and after heating of the coating film was measured using a color measuring machine (OSP-SP-200; manufactured by OLYMPUS). The coating film obtained in Example 2 was evaluated for heat resistance, and as a result, the color difference (ΔEab*) was 4.3. Further, in the same manner as in Comparative Example 1, the heat resistance was evaluated, and as a result, the color difference (ΔEab*) was 12.9, and it was found that the compound of the present application was excellent in heat resistance.

Industrial availability

When a colored curable resin composition containing the present compound is used, a coating film having good heat resistance can be provided. The coating film can be used as a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper) And the color filters used in the solid-state imaging device.

Claims (7)

A compound comprising: a compound (a) having a cation and an anion in a molecule; an anion (b) having at least one element selected from the group consisting of tungsten, molybdenum, niobium and phosphorus, and oxygen as an essential element; And a cation (c) containing an alkaline earth metal. The compound of claim 1, wherein the compound (a) is a xanthene compound (a1). The compound of claim 2, wherein the xanthene compound (a1) is a compound represented by the formula (a1-1): In the formula (a1-1), R ¹ to R ⁴ each independently represent a hydrogen atom, a C 6-10 aromatic hydrocarbon group which may have a substituent, or a C 1-20 saturated hydrocarbon group which may have a substituent. The methylene group (-CH ₂ -) contained in the saturated hydroxyl group may be -O-, -CO-, -N(R ¹⁰ )-, -OCO-, -COO-, -OCONH-, -NHCOO-, - CONH-, or -NHCO- substitution, however, the adjacent -CH ₂ - will not be replaced by the same group at the same time, and the -CH ₂ - at the end will not be replaced, and R ¹ and R ² may together form a ring of a nitrogen atom, R ³ and R ⁴ may together form a ring containing a nitrogen atom, and R ⁵ and R ⁶ independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ¹⁰ represents a hydrogen atom and a carbon number of 1 to 6; A saturated hydrocarbon group of 20 or an aralkyl group having 7 to 10 carbon atoms. The compound according to claim 1, wherein the cation (c) is at least one selected from the group consisting of a magnesium cation, a calcium cation, a phosphonium cation, and a phosphonium cation. A colored curable resin composition comprising the compound according to any one of claims 1 to 4, a resin, a polymerizable compound, and a polymerization initiator. A color filter formed of the colored curable resin composition as claimed in claim 5. A liquid crystal display device having the color filter of claim 6.