TWI794147B - Compound, colored curable resin composition, color filter and liquid crystal display device - Google Patents

Abstract

The subject of this invention is providing the compound which can provide the color filter excellent in heat resistance, and the display device containing it, and a colored curable resin composition. 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 tungsten, molybdenum, silicon, and phosphorus and oxygen as essential elements; and A cation (c) containing an 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 having a cation and an anion in a molecule, a compound containing 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

It is desired that a coating film formed from a colored curable resin composition be excellent in heat resistance, and various techniques have been developed to improve heat resistance and the like.

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

prior art literature patent documents

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

Summary of the invention

In this Patent Document 1, a salt-forming compound is disclosed in terms of improving desired characteristics, but none of the Patent Documents teaches the use of a compound having both cations and anions in the molecule as a compound having heat resistance. compound.

Therefore, the subject of this invention is providing the colored curable resin composition which can form the coating film which has favorable heat resistance, and the compound used for this 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) containing at least one element selected from tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements; and A cation (c) containing an alkaline earth metal.

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

[3] The compound described in [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 independently represent a hydrogen atom, an aromatic hydrocarbon group with a carbon number of 6 to 10 that may have a substituent, or a saturated hydrocarbon group with a carbon number of 1 to 20 that may have a substituent, The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be replaced by -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 terminal -CH ₂ - will not be replaced either.

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

R ⁵ and R ⁶ independently 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 carbons, or an aralkyl group having 7 to 10 carbons. ]

[4] The compound according to any one of [1] to [3], wherein the cation (c) is at least one selected from magnesium cations, calcium cations, strontium cations, and barium cations.

[5] A colored curable resin composition comprising the compound described in 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 described in [5].

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

According to the present 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 therein.

Detailed Description of the Preferred Embodiment

1. compound

The compound of the present invention is characterized in that it comprises: a compound (a) having cations and anions in the molecule (hereinafter sometimes referred to as compound (a).); at least 1 selected from tungsten, molybdenum, silicon and phosphorus elements and oxygen as essential elements (b); and cations (c) containing alkaline earth metals.

1-1． Compound (a)

Compound (a) has cations and anions in the molecule. The cations and anions in the molecule may have the same charge number or different charge numbers, and the cations and anions having the same charge number in the molecule are preferred. It is more preferable to have cations and anions with the same number of charges of 1 to 5 in the molecule, and it is more preferable to have cations and anions with the same number of charges in the molecule from 1 to 3, and it is particularly preferable to have cations and anions with the same number of charges in the molecule. cations and anions with a charge number.

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

1-1-1． Xanthene compounds

As the xanthene compound (a1), a compound represented by the formula (a1-1) (hereinafter sometimes referred to as "compound (a1)") is preferable. Compound (a1) may be its tautomer.

[In the formula (a1-1), R ¹ to R ⁴ independently represent a hydrogen atom, an aromatic hydrocarbon group with a carbon number of 6 to 10 that may have a substituent, or a saturated hydrocarbon group with a carbon number of 1 to 20 that may have a substituent, The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be replaced by -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 terminal -CH ₂ - will not be replaced either.

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

R ⁵ and R ⁶ independently 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 carbons, or an aralkyl group having 7 to 10 carbons. ]

Examples of saturated hydrocarbon groups having 1 to 20 carbon atoms in R ¹ to R ⁴ and R ¹⁰ include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, Straight-chain alkyl groups such as decyl, dodecyl, hexadecyl, and eicosyl; branched-chain alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl alicyclic saturated hydrocarbon groups with 3 to 20 carbons such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecanyl. The saturated hydrocarbon groups of R ¹ to R ⁴ and R ¹⁰ are more preferably 1 to 15 carbons, still more preferably 1 to 10 carbons, still more preferably 1 to 6 carbons.

The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be replaced by -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 terminal -CH ₂ - will not be replaced either.

Examples of the group in which the methylene group (—CH ₂ —) contained in the saturated hydrocarbon group is replaced by —O— include the following groups (* indicates a bonding terminal).

Examples of the group in which the methylene group (—CH ₂ —) contained in the saturated hydrocarbon group is replaced by —CO— include the following groups (* indicates a bonding terminal).

Examples of the group in which the methylene group (—CH ₂ —) contained in the saturated hydrocarbon group is replaced by —NR ¹⁰ — include the following groups (* indicates a bonding terminal).

Examples of the group in which the methylene group (—CH ₂ —) contained in the saturated hydrocarbon group is replaced by —OCO— include the following groups (* indicates a bonding terminal).

Examples of the group in which the methylene group (—CH ₂ —) contained in the saturated hydrocarbon group is replaced by —COO— include the following groups (* indicates a bonding terminal).

Examples of the group in which the methylene group (—CH ₂ —) contained in the saturated hydrocarbon group is replaced by —OCONH— include the following groups (* indicates a bonding terminal).

Examples of the group in which the methylene group (—CH ₂ —) contained in the saturated hydrocarbon group is replaced by —NHCOO— include the following groups (* indicates a bonding terminal).

Examples of the group in which the methylene group (—CH ₂ —) contained in the saturated hydrocarbon group is replaced by —CONH— include the following groups (* indicates a bonding terminal).

Examples of the group in which the methylene group (—CH ₂ —) contained in the saturated hydrocarbon group is replaced by —NHCO— include the following groups (* indicates a bonding terminal).

Examples of substituents that the saturated hydrocarbon groups represented by R ¹ to R ⁴ may have include aromatic hydrocarbon groups having 6 to 10 carbon atoms or halogen atoms.

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

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, etc. are mentioned.

Examples of the ring formed by R ¹ and R ² and 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 phenyl, tolyl, xylyl, mesityl, propylphenyl, and butylphenyl.

The aromatic hydrocarbon group having 6 to 10 carbon atoms may have a substituent. Examples of substituents that the aromatic hydrocarbon group may have include halogen atoms, -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 will not be replaced by the same group at the same time, and the terminal methylene groups will not be replaced either.

R ⁸ and R ⁹ independently represent a hydroxyl group or a saturated hydrocarbon group with 1 to 10 carbon atoms that may be substituted by a halogen atom, or a hydrogen atom.

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

Examples of -OR ⁷ include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy and di Alkoxy groups such as dedecyloxy and the like.

Examples of -CO ₂ R ⁷ include alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, t-butoxycarbonyl, hexyloxycarbonyl and eicosyloxycarbonyl.

Examples of -SR ⁷ include alkylsulfanes such as methylsulfanyl, ethylsulfanyl, butylsulfanyl, hexylsulfanyl, decylsulfanyl, and eicosylsulfanyl. Base etc.

Examples of -SO ₂ R ⁷ include alkyl groups such as methylsulfonyl, ethylsulfonyl, butylsulfonyl, hexylsulfonyl, decylsulfonyl and eicosylsulfonyl. Sulfonyl, etc.

Examples of -SO ₃ R ⁷ include methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, t-butoxysulfonyl, hexyloxysulfonyl and eicosyl Alkoxysulfonyl groups such as oxysulfonyl groups and the like.

Examples of -SO ₂ N(R ⁸ )(R ⁹ ) include sulfamoyl; N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl , N-pentylsulfamoyl, N-(1-ethylpropyl)sulfamoyl, N-(1,1-dimethylpropyl)sulfamoyl, N-(1,2- Dimethylpropyl)sulfamoyl, N-(2,2-dimethylpropyl)sulfamoyl, N-(1-methylbutyl)sulfamoyl, N-(2-methyl butyl) sulfamoyl, N-(3-methylbutyl) sulfamoyl, N-cyclopentyl sulfamoyl, N-hexyl sulfamoyl, N-(1,3-di Methylbutyl)sulfamoyl, N-(3,3-dimethylbutyl)sulfamoyl, N-heptylsulfamoyl, N-(1-methylhexyl)sulfamoyl , N-(1,4-dimethylpentyl)sulfamoyl, N-octylsulfamoyl, N-(2-ethylhexyl)sulfamoyl, N-(1,5-di Methylhexyl) sulfamoyl, N-(1,1,2,2-tetramethylbutyl) sulfamoyl and other N-1 substituted sulfamoyl groups; N,N-dimethylsulfamoyl N,N-Ethylmethylsulfamoyl, N,N-Diethylsulfamoyl, N,N-Propylmethylsulfamoyl, N,N-Isopropylmethylamine Sulfonyl, N,N-tert-butylmethylsulfamoyl, N,N-butylethylsulfamoyl, N,N-bis(1-methylpropyl)sulfamoyl, N, N, N-2 substituted sulfamoyl groups such as N-heptylmethylsulfamoyl group, etc.

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

R ⁸ and R ⁹ may independently represent a 3-10 membered nitrogen-containing heterocyclic ring together with a nitrogen atom. As this heterocycle, the following heterocycles are mentioned, for example.

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

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

As the aforementioned ⁺ N(R ¹⁰ ) ₄ , at least two of the four R ^10s are preferably monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. In addition, the total carbon number of four ^R10s is preferably 20-80, more preferably 20-60. When ⁺ N(R ¹⁰ ) ₄ exists in the compound (a1), if R ¹⁰ is these groups, a color filter with less foreign matter can be formed from the colored curable resin composition of the present invention containing the compound (a1) .

Among these, -R ⁷ , -SO ₃ ^- , -SO ₃ H, -SO ₃ ^- Z ⁺ and -SO ₂ N(R ⁸ )(R ⁹ ) are preferred as substituents, and -R ⁷ , -SO are more preferred. ₃ ^- Z ⁺ and -SO ₂ N(R ⁸ )(R ⁹ ). -R ⁷ in this case is more preferably a monovalent alkyl group having 1 to 10 carbons, still more preferably an alkyl group having 1 to 5 carbons, and still more preferably a methyl group or an ethyl group. Also -SO ₃ ^- Z ⁺ in this case is preferably -SO ₃ ^-+ N(R ¹⁰ ) ₄ .

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

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

[In the formula (a1-1-1), R ^1b to R ^4b independently represent a saturated hydrocarbon group with 1 to 20 carbon atoms that may have a substituent, and the 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 terminal -CH ₂ - will not be replaced either. R ^1b and R ^2b can form a ring containing nitrogen atoms together, and R ^3b and R ^4b can form a ring containing nitrogen atoms together ring of atoms.

R ^5b and R ^6b independently represent a hydrogen atom or an alkyl group having 1 to 6 carbons.

R ^11b represents a hydrogen atom, a saturated hydrocarbon group with 1 to 20 carbons, or an aralkyl group with 7 to 10 carbons. ]

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 replaced by -O-, -CO-, -N(R ^11b )-, -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 terminal -CH ₂ - will not be replaced either.

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, toluene Base, xylyl, mesityl, propylphenyl and butylphenyl, etc.

In compound (a1-1-1), R ^1b and R ^2b , R ^3b and R ^4b among R 1b to R ^4b are preferably each the same saturated hydrocarbon group, preferably R ^1b and ^{R 2b ,} R ^3b and R ^4b are each a straight A combination of chained alkyl groups, more preferably a combination of R ^1b and R ^2b , R ^3b and R ^4b each being a linear alkyl group with 1 to 5 carbons, more preferably R ^1b and R ^2b , R ^3b and R ^4b is each a combination of two selected from methyl, ethyl, propyl, and butyl.

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 alkyl groups having 1 to 6 carbon atoms among the alkyl groups listed above. Among them, a hydrogen atom is preferable as R ^5b and R ^6b .

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

In addition, as the compound represented by formula (a1-1), a compound represented by the following formula (a1-1-2) (hereinafter may be referred to as "compound (a1-1-2)") is preferable. Compound (a1-1-2) may be its tautomer.

[In the formula (a1-1-2), R ^1c and R ^4c independently represent an alkyl group with 1 to 4 carbons, an alkylsulfanyl group with 1 to 4 carbons, or an alkyl sulfonate with 1 to 4 carbons Acyl group.

p and q mutually independently represent the integer of 0-5. 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 represent a hydrogen atom or a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have a substituent, and the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be replaced by -O- , -CO-, -N(R ^11c )-, -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 terminal -CH ₂ - will not be replaced either.

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 represent a hydrogen atom or an alkyl group having 1 to 6 carbons.

R ^11c represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbons, or an aralkyl group having 7 to 10 carbons. ]

Examples of the alkyl group having 1 to 4 carbon atoms in R ^1c and R ^4c include methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, tert-butyl and the like.

Examples of alkylsulfanyl groups having 1 to 4 carbon atoms in ^R and ^R include methylsulfanyl, ethylsulfanyl, propylsulfanyl, butylsulfanyl, and isopropyl Sulfuryl, etc.

Examples of alkylsulfonyl groups having 1 to 4 carbon atoms in ^R1c and ^R4c include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl and isopropyl Sulfonyl, etc.

Wherein, R ^1c and R ^4c are preferably alkyl groups with 1 to 4 carbon atoms, more preferably methyl groups and ethyl groups.

p and q are preferably integers of 0-2, preferably 1 or 2.

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

The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be replaced by -O-, -CO-, -N(R ^11c )-, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH- or -NHCO- substitution. However, adjacent -CH ₂ -s are not simultaneously substituted with the same group, and terminal -CH ₂ -s are not substituted either.

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.

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, etc. are mentioned.

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

Examples of the alkyl group having 1 to 6 carbon atoms in R ^5c and R ^6c include alkyl groups having 1 to 6 carbon atoms among the alkyl groups listed above. Among them, a hydrogen atom is preferable as R ^5c and R ^6c .

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

Examples of the compound (a1) include compounds represented by formulas (I-1) to (I-25). In addition, in formula (I-1) ~ formula (I-25), R ⁴⁰ represents the monovalent saturated hydrocarbon group of carbon number 1 ~ 20, preferably represents the branched chain alkyl group of carbon number 6 ~ 12, more preferably means 2-ethylhexyl.

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

1-1-2． squaraine

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

[In the formula (a2-1), R ^a1 ~ R ^a4 independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an aromatic hydrocarbon group with a carbon number of 6 to 20 or a saturated hydrocarbon group with a carbon number of 1 to 20, R ^a1 and R ^a5 , R ^a2 and R ^a6 , R ^a3 and R ^a7 , R ^a4 and R ^a8 can each form a ring with their bonded carbon atoms, 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 the nitrogen atom and the carbon atom to which they are bonded.

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

R ^a9 to R ^a12 independently represent an aromatic hydrocarbon group that may have a substituent, a saturated hydrocarbon group with 4 to 20 carbon atoms that may have a substituent, or an unsaturated aliphatic hydrocarbon group with 4 to 20 carbon atoms that may have a substituent, The methylene group constituting the saturated hydrocarbon group or unsaturated aliphatic hydrocarbon group may be replaced by an oxygen atom, a sulfur atom, -N(R ^a24 )-, a sulfonyl group, or a carbonyl group. In addition, 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 that may have a substituent, and the methylene group constituting the monovalent saturated hydrocarbon group may be replaced by an oxygen atom, a sulfur atom, -N(R ^a25 )-, a sulfonyl group, or carbonyl. However, the adjacent methylene groups will not be replaced by the same group at the same time, and the terminal methylene groups will not be replaced either.

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

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

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

As the aromatic hydrocarbon group of R ^a1 ~ R ^a4 , aryl groups such as phenyl, tolyl, xylyl, mesityl, cumenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, etc.; Aralkyl groups such as radicals, phenylethyl groups, phenylbutyl groups, etc.; aryloxy groups such as phenoxy groups, etc.

The saturated hydrocarbon groups with 1 to 20 carbons in R ^a1 to R ^a4 and R ^a23 to R ^a25 are preferably 1 to 12 carbons, more preferably 1 to 10 carbons, further preferably 1 to 8 carbons, particularly preferably Carbon number 1~7. Specifically, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, eicosyl, etc. Straight-chain alkyl groups with 1-20 carbons; isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, 1-ethylpentyl, and 2-ethylhexyl, etc. Branched-chain alkyl groups with 3 to 20 carbons; alicyclic saturated hydrocarbon groups with 3 to 20 carbons such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and tricyclodecanyl.

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 aminoformyl group; an amine Sulfonyl group; Hydroxyl group; Amino group, etc.

Examples of groups in which a methylene group constituting a monovalent saturated hydrocarbon group is replaced by an oxygen atom include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec- Alkoxy groups such as butoxy, tert-butoxy, and pentyloxy, etc.

In addition, as a group in which the methylene group constituting a monovalent saturated hydrocarbon group is replaced by an oxygen atom, and a carbonyl group, alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, and propoxycarbonyl can be cited; Alkylcarbonyloxy groups such as acyloxy groups; groups having ester bonds such as arylcarbonyloxy groups such as benzoyloxy groups.

Furthermore, examples of a group in which the methylene group constituting a monovalent saturated hydrocarbon group is replaced by -N(R ^a24 )- or -N(R ^a25 )- and a carbonyl group include N-methylaminoformyl, N-ethylaminoformyl, N-propylaminoformyl, N-isopropylaminoformyl, N-butylaminoformyl, N-isobutylaminoformyl Base, N-sec-butylaminoformyl, N-tert-butylaminoformyl, N-pentylaminoformyl, N-(1-ethylpropyl)aminoformyl N-1 substituted aminoformyl such as N-(1,1-dimethylpropyl)aminoformyl; N,N-dimethylaminoformyl, N,N-ethyl Methylaminoformyl, N,N-Diethylaminoformyl, N,N-Propylmethylaminoformyl, N,N-Isopropylmethylaminoformyl, N,N-tert-butylmethylaminoformyl, N,N-butylethylaminoformyl, N,N-bis(1-methylpropyl)aminoformyl, N,N -Heptylmethylaminoformyl, N,N-bis(2-ethylhexyl)aminoformyl, etc. N,N-2 substituted aminoformyl, etc.

As a group in which the methylene group constituting a monovalent saturated hydrocarbon group is replaced by a sulfonyl group, and -N(R ^a24 )- or -N(R ^a25 )-, N-methylsulfamoyl group, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-sec-butylsulfamoyl, N- tert-Butylsulfamoyl, N-pentylsulfamoyl, N-(1-ethylpropyl)sulfamoyl, N-cyclopentylsulfamoyl, N-hexylsulfamoyl , N-(1,3-dimethylbutyl) sulfamoyl and other N-1 substituted sulfamoyl groups; N,N-dimethylsulfamoyl, N,N-ethylmethylsulfamoyl N,N- 2 substituted sulfamoyl groups 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 )- include N-methylamino group, N-ethylamino group, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-sec-butylamino, N-tert-butylamino, N- Pentylamino, N-(1-ethylpropyl)amino, N-(1,1-dimethylpropyl)amino, N-(1,2-dimethylpropyl)aminodi N-alkylamine groups such as methylhexyl)amine, 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)aminomethyl, etc. N-alkylaminomethyl; N,N-dimethylaminomethyl Methyl, N,N-ethylmethylaminomethyl, N,N-diethylaminomethyl, N,N-propylmethylaminomethyl, N,N-isopropylmethyl Aminomethyl, N,N-tert-butylmethylaminomethyl, N,N-butylethylaminomethyl, N,N-bis(1-methylpropyl)aminomethyl, N , N-heptylmethylaminomethyl, N,N-bis(2-ethylhexyl)aminomethyl, etc. N,N-dialkylaminomethyl, etc.

Examples of the ring formed by each of R ^a1 and R ^a5 , R ^a2 and R ^a6 , R ^a3 and R ^a7 , R ^a4 and R ^a8 together with the carbon atoms to which they are bound, include structures represented by the following formulas, and the like. 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 bonded end.

Examples of the ring formed by each of R ^a1 and R ^a9 , R ^a2 and R ^a10 , R ^a3 and R ^a11 , R ^a4 and R ^a12 together with the nitrogen atom and carbon atom to which they are bonded, include structures represented by the following formula, etc. . 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 bonded end.

The aromatic hydrocarbon group which may have a substituent in R ^a9 to R ^a12 preferably has 6 or more carbon atoms, more preferably 8 or more carbon atoms, preferably 18 or less carbon atoms, more preferably 15 or less carbon atoms. As the aromatic hydrocarbon group represented by R ^a9 to R ^a12 , aryl groups with 6 to 12 carbons such as phenyl, tolyl, xylyl, mesityl, propylphenyl and butylphenyl can be mentioned; Benzyl, phenylethyl, phenylbutyl and other aralkyl groups with 7 to 12 carbons. In addition, the aryl group is particularly preferably a phenyl group, and the aralkyl group is particularly preferably a benzyl group.

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

In addition, the aryl group preferably has a substituent at the ortho position of the bonding terminal, and the aralkyl group preferably has a substituent at the ortho position of the alkylene group. As the aromatic hydrocarbon group which may have a substituent of R ^a9 -R ^a12 , the group represented by the following formula etc. are mentioned. In the formula, * represents the bonding end.

Examples of saturated hydrocarbon groups having 4 to 20 carbon atoms in R ^a9 to R ^a12 include butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and eicosyl and other straight-chain alkyl groups; 2-ethylhexyl and other branched-chain alkyl groups. Furthermore, examples of monovalent unsaturated aliphatic hydrocarbon groups having 4 to 20 carbon atoms in R ^a9 to R ^a12 include butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonyl Straight-chain alkenyl groups such as alkenyl, decenyl, dodecenyl, hexadecenyl, and eicosenyl, and the like.

The saturated hydrocarbon groups having 4 to 20 carbon atoms in R ^a9 to R ^a12 may have substituents, and examples of the substituents include halogen atoms such as fluorine atoms, chlorine atoms, and bromine atoms; cyano groups; nitro groups; aminoformyl groups ; Aminosulfonyl; Hydroxyl; Amino, etc.

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 structures represented by the following formulas, and the like.

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), a hydrogen atom is preferable as R ^a1 to R ^a4 .

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 even more preferably a hydrogen atom.

R ^a9 to R ^a12 are independently preferably an aromatic hydrocarbon group with 8 to 20 carbon atoms that may have a substituent or a saturated hydrocarbon group with 4 to 20 carbon atoms that may have a substituent, more preferably a carbon number that may have a substituent 4~20 monovalent aromatic hydrocarbon group.

R ^a23 is preferably a saturated hydrocarbon group having 1 to 20 carbons, more preferably a saturated hydrocarbon group having 1 to 8 carbons, and even more preferably a saturated hydrocarbon group having 1 to 4 carbons.

R ^a24 and R ^a25 are independently preferably a saturated hydrocarbon group having 1 to 20 carbons, more preferably a saturated hydrocarbon group having 1 to 8 carbons, and even more preferably a saturated hydrocarbon group having 1 to 4 carbons.

Moreover, as a group represented by following formula (x-1) and (x-2), respectively, the group represented by a formula (A1-1) - a formula (A1-8) is mentioned.

Furthermore, in these formulas, * represents a bonding end, and >N-* can be >N ⁺ =*.

In addition, as the groups represented by the formulas (x-1) and (x-2), for example, in addition to the groups represented by the formulas (A1-1) to (A1-8) shown above, for example, Groups represented by formulas (A2-1) to (A2-7) are produced. * indicates the bonding end, >N-* can be >N ⁺ =*.

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

Have again, in formula (AI-a) and table 1～4, R ^a1 ～R ^a8 are synonymous with R ^a1 ～R ^a8 in above-mentioned formula (a2-1) respectively, X ^a1 , X ^a2 mean respectively by formula ( The group represented by x-1), (x-2).

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

group shown. *Indicates bonded end.

From the viewpoint of raw material availability, compound (AI-16) to compound (AI-30) are more preferred, and compound (AI-16), compound (AI-17) and compound (AI-22) are further preferred.

1-2． Anion (b)

The anion (b) is an anion containing at least one element selected from tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements.

The anion is preferably an anion compound of a heteropolyacid or isopolyacid containing tungsten as an essential element, more preferably anion of phosphotungstic acid, silicotungstic acid, and tungsten-based isopolyacid.

Examples of anions of heteropolyacids or isopolyacids 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 silicotungstic acid ions α-[SiW ₁₂ O ₄₀ ] ^4- , β-[SiW ₁₂ O ₄₀ ] ^4- , γ- [SiW ₁₂ O ₄₀ ] ^4- , and further examples include [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- , etc. Among them, the Keggin-type phosphotungstic acid ion α-[PW ₁₂ O ₄₀ ] ^3- is particularly preferred.

1-3． Cation (c)

The cation (c) is a cation containing an alkaline earth metal, preferably at least one selected from magnesium cations, calcium cations, strontium cations, and barium cations, more preferably calcium cations or barium cations. These may be derived from alkaline earth metal halides that can be precipitated after forming the target substance, and the alkaline earth metal halides may be magnesium chloride, calcium chloride, strontium chloride, barium chloride, and the like.

When 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 further satisfied with the relationship of Bc ^(-) = Cd ⁽⁺⁾ . The total number of charges of Aa ⁽⁺⁾ , Bc ^(-) , Ab ^(-) , Cd ⁽⁺⁾ is preferably an even multiple, and the total charge of Aa ⁽⁺⁾ , Bc ^(-) , Ab ^(-) , Cd ⁽⁺⁾ The number of charges is more preferably 6, 8, 12, 16, 18, 24 or 36, and still more preferably 6, 8 or 12, respectively.

A is preferably an even multiple, more preferably 6, 8, 12, 16, 18, 24 or 36, even more 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, even more preferably 2.

c is preferably 3, 4 or 6.

C is preferably 3, 4 or 6.

d is preferably an even multiple, more preferably 2.

1-4. Examples of compounds containing xanthene compounds

Compounds containing the compound (a), which is a xanthene compound, the above-mentioned anion (b), and the above-mentioned cation (c) are exemplified below.

1-5． Examples of compounds containing squaraine compounds

Compounds containing the squaraine compound that is the compound (a), the above-mentioned anion (b), and the above-mentioned cation (c) are exemplified below.

Ra below represents the following groups.

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

The compounds of the invention can be used as colorants.

2. Colored Curable Resin Composition

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

A coloring agent (A1) may combine 2 or more types.

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

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

Examples of dyes for the colorant (A2) include solvents (Solvent), acid (Acid), basic (Basic), reactive (reactive), Direct (Direct), disperse (Disperse), or reduced (Vat) compounds, known dyes described in Dyeing Notes (Yorsensha). In addition, depending on the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, and the like are exemplified. These dyes may be used in combination of two or more.

Specifically, dyes with the following color index (C.I.) numbers are exemplified. Examples include: C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162; C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112 ,113,114,116,119,123,128,134,135,138,139,140,144,150,155,157,160,161,163,168,169,172,177,178,179,184 , 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; C.I. active yellow 2, 76, 116; C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94 , 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; C.I. Disperse Yellow 51, 54, 76; C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99 ; C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; C.I. Reactive Orange 16; C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; C.I. Solvent Red 24, 49 ,90,91,111,118,119,122,124,125,127,130,132,143,145,146,150,151,155,160,168,169,172,175,181,207,218 , 222, 227, 230, 245, 247; C.I. Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289; C.I. Acid Violet 34, 102; C.I. Disperse Violet 26, 27; C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. 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; C.I. Acid Blue 25, 27, 40, 45, 78, 80, 112; C.I. Direct Blue 40; C.I. Disperse Blue 1, 14, 56, 60; C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33; C.I. acid green 3, 5, 9, 25, 27, 28, 41; C.I. basic green 1; C.I. vat green 1, etc.

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

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

For pigments, if necessary, rosin treatment, surface treatment using pigment derivatives with introduced acidic groups or basic groups, etc., grafting treatment on the surface of pigments with polymer compounds, micronization with sulfuric acid, etc. Micronization treatment using the method, etc., washing treatment using organic solvents, water, etc. for removing impurities, removal treatment of ionic impurities using ion exchange methods, etc., etc. It is preferred that the particle size of the pigment is substantially uniform. The pigment is subjected to dispersion treatment by containing a pigment dispersant, and can be prepared as a pigment dispersion liquid in a state of being uniformly dispersed in a pigment dispersant solution. Pigments may be dispersed individually or in combination of multiple pigments.

(共榮社化 學(株)製造)、

(註冊商標)(

(株)製造)、EFKA(註冊商標)(BASF公司製造)、

(註冊商標)(味之素

(株)製造)、Disperbyk(註冊商標)(

公司製造)等。 Examples of the pigment dispersant include surfactants and the like, and may be any of cationic, anionic, nonionic, and amphoteric surfactants. Specifically, polyester-based, polyamine-based, acrylic-based, and other surfactants are exemplified. These pigment dispersants can be used alone or in combination of two or more. The pigment dispersant is represented by a trade name, and examples include KP (manufactured by Shin-Etsu Chemical Co., Ltd.),

(manufactured by Kyoeisha Chemical Co., Ltd.),

(Trademark)(

(manufactured by Co., Ltd.), EFKA (registered trademark) (manufactured by BASF Corporation),

(registered trademark) (Ajinomoto

(Co., Ltd.)), Disperbyk (registered trademark) (

manufactured by the company), etc.

When using a pigment dispersant, the usage-amount is preferably 100 mass parts or less with respect to 100 mass parts of pigments, More preferably, it is 5 mass parts or more and 50 mass parts or less. When the usage-amount of a pigment dispersant exists in the said range, there exists a tendency for the pigment dispersion liquid of a more uniform dispersion state to be obtained.

The content of the colorant (A1) in the colored curable resin composition is usually not less than 0.01% by mass and not more than 70% by mass, preferably not less than 0.1% by mass and not more than 60% by mass based on the total solid content, and more preferably Preferably it is 0.2 mass % or more and 60 mass % or less, Especially preferably, it is 0.3 mass % or more and 50 mass % or less. When the content rate of a coloring agent (A1) exists in the said range, desired light spectrum and color density will be acquired more easily. In addition, "the total amount of solid content" in this specification means the total amount of the component which removed the solvent from the colored curable resin composition of this invention. The total amount of solid content and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography and gas chromatography, for example.

When the coloring agent (A2) may be further included, the ratio of the amount of the coloring agent (A1) to the amount of the coloring agent (A2) (coloring agent (A1) (in terms of solid content)/coloring agent (A2) (solid Component conversion)) is preferably 0.1 to 100, more preferably 0.5 to 50, further preferably 1 to 25, particularly preferably 1 to 10, and most preferably 2 to 6.

<Resin (B)>

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

Resin [K1]: at least one (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)"), and cyclic ether structures and alkenes having 2 to 4 carbon atoms Copolymers of monomers (b) (hereinafter sometimes referred to as "(b)") that are unsaturated bonds;

Resin [K2]: (a), (b), and monomer (c) copolymerizable with (a) (However, it is different from (a) and (b).) (hereinafter sometimes referred to as "(c) ”) of copolymers

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

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

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

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

Examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, ortho-, meta-, and p-vinylbenzoic acid; unsaturated dicarboxylic acids such as maleic acid; methyl-5 -norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, etc. unsaturated compounds; Unsaturated dicarboxylic anhydrides such as maleic anhydride; unsaturated acrylic acid esters containing hydroxyl and carboxyl groups in the same molecule, such as α-(hydroxymethyl)acrylic acid.

Among them, acrylic acid, methacrylic acid, and maleic anhydride are preferable from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an aqueous alkali solution.

(b) refers to the polymerization of a cyclic ether structure (for example, at least one selected from an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) with a carbon number of 2 to 4 and an ethylenically unsaturated bond Sexual compounds. (b) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms and a (meth)acryloyloxy group. In addition, in this specification, "(meth)acrylic acid" means at least 1 sort(s) chosen from acrylic acid and methacrylic acid. The expressions "(meth)acryl" and "(meth)acrylate" also have the same meaning.

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

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

(b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond. Specific examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, (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(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis (glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3 ,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene and 2,4,6-tris(glycidyloxymethyl)styrene .

(註冊商標)2000；(株)大賽璐製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如，

(註冊商標)A400；(株)大賽璐製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如，

M100；(株)大賽璐製造)、由式(1)表示的化合物和由式(2)表示的化合物。 Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example,

(registered trademark) 2000; manufactured by Daicel), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example,

(registered trademark) A400; manufactured by Daicel), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example,

M100; manufactured by Daicel), a compound represented by formula (1), and a compound represented by formula (2).

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

X ^a and X ^b independently represent 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 bonded end with O. ]

As the compound represented by formula (1), compounds represented by formula (1-1) to formula (1-15) can be enumerated, among which, formula (1-1), formula (1-3), formula (1-5), formula (1-7), formula (1-9) and the compound represented by formula (1-11) ~ formula (1-15), more preferably by formula (1-1), formula (1 -7), compounds represented by formula (1-9) and formula (1-15).

As the compound represented by formula (2), compounds represented by formula (2-1) to formula (2-15) can be enumerated, among which, formula (2-1), formula (2-3), formula (2-5), formula (2-7), formula (2-9) and the compound represented by formula (2-11) ~ formula (2-15), more preferably by formula (2-1), formula (2 -7), compounds represented by formula (2-9) and formula (2-15).

The compound represented by formula (1) and the compound represented by formula (2) may be used alone, or the compound represented by formula (1) and the compound represented by formula (2) may be used in combination. 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)) is on a molar basis, Preferably it is 5:95~95:5, More preferably, it is 10:90~90:10, More preferably, it is 20:80~80:20.

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

(b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloxy group.

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

Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, and tert-butyl (meth)acrylate. , 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, Cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate (in this technical field , as a common name, it is called "dicyclopentyl (meth)acrylate". In addition, it is sometimes called "tricyclodecanyl (meth)acrylate".), tricyclo[5.2.1.0 ^{2 ,6} ] Decen-8-yl ester (in this technical field, as a common name, it is called "(meth)acrylate dicyclopentenyl ester".), (meth)acrylate dicyclopentyloxyethyl ester, (meth)acrylate base) isobornyl acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, (Meth)acrylates such as benzyl (meth)acrylate; (meth)acrylates containing hydroxyl groups such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; maleic acid Diethyl ester, diethyl fumarate, diethyl itaconate and other dicarboxylic acid diesters; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2- ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-Hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1] Hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6- Bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo [2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene , 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonyl Bicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept -2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; N-phenylmaleimide, N-cyclohexylmale Amide, N-benzylmaleimide, N-succinimidyl-3-maleimide Laylimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide hexanoate, N-succinimidyl Dicarbonylimide compounds such as imido-3-maleimide propionate, N-(9-acridyl)maleimide, etc.; styrene, α-methylstyrene, m-formaldehyde Vinyl styrene, p-methylstyrene, vinyl toluene, p-methoxystyrene and other vinyl-containing aromatic compounds; acrylonitrile, methacrylonitrile and other vinyl-containing nitriles; vinyl chloride, partial chloride Halogenated hydrocarbons such as ethylene; amides containing vinyl groups such as acrylamide and methacrylamide; esters such as vinyl acetate; 1,3-butadiene, isoprene and 2,3-dimethyl- Dienes such as 1,3-butadiene, etc.

Among these, vinyl group-containing aromatic compounds, dicarbonylimine compounds, and bicyclic unsaturated compounds are preferable from the viewpoint of copolymerization reactivity and heat resistance. Specifically, styrene, vinyltoluene, benzyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, N-phenylmaleimide Amine, N-cyclohexylmaleimide, N-benzylmaleimide, and bicyclo[2.2.1]hept-2-ene.

Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, Dicarboxylic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride. The usage-amount of carboxylic anhydride is preferably 0.5-1 mole with respect to 1 mole of the usage-amount of (a).

Examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxycyclohexyl (meth)acrylate [5.2.1.0 ^2.6 ]decyl ester/(meth)acrylic acid copolymer and other resins [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[5.2.1.0 ^2.6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3-methyl-3-(meth)acryloxy Resins such as methyl oxetane/(meth)acrylic acid/styrene copolymer [K2]; benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer Resins such as benzyl (meth)acrylate/tricyclodecanyl (meth)acrylate/(meth)acrylic acid copolymer [K3]; make glycidyl (meth)acrylate and benzyl (meth)acrylate /Resin obtained by addition of (meth)acrylic acid copolymer, resin obtained by addition of glycidyl (meth)acrylate and tricyclodecanyl (meth)acrylate/styrene/(meth)acrylic acid copolymer Resins, resins such as resins obtained by adding glycidyl (meth)acrylate to tricyclodecanyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymers [K4]; (Meth)acrylic acid and tricyclodecanyl (meth)acrylate/glycidyl (meth)acrylate copolymer reaction resin, made of (meth)acrylic acid and tricyclodecanyl (meth)acrylate/ Resins such as resins formed by the reaction of copolymers of styrene/glycidyl (meth)acrylate [K5]; The resin formed by the reaction of the copolymer is further reacted with tetrahydrophthalic anhydride and other resins [K6].

The polystyrene-equivalent weight-average molecular weight of the resin (B) is usually 3,000 to 100,000, preferably 5,000 to 50,000, more preferably 5,000 to 35,000, further preferably 5,000 to 30,000, particularly preferably 6,000 to 25,000. When the molecular weight is within the above-mentioned range, the hardness of the coating film increases, the residual film rate is also high, the solubility of the unexposed portion to the developing solution becomes favorable, and the resolution of the colored pattern tends to improve.

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

The acid value (solid content conversion) of the resin (B) is preferably 20 to 170 mg-KOH/g, more preferably 30 to 170 mg-KOH/g, wherein, Preferably 40-170 mg-KOH/g, preferably 50-170 mg-KOH/g, more preferably 150 mg-KOH/g or less, further 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 an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 7 to 65% by mass, particularly preferably 10 to 60% by mass, particularly preferably 13 to 60% by mass, particularly preferably 17 to 55% by mass, based on the total solid content. When the content of the resin (B) is within the above-mentioned range, it is easy to form a colored pattern, and the resolution and remaining film ratio of the colored pattern tend to improve.

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized by active radicals and/or acids generated by a polymerization initiator, and examples thereof include polymerizable compounds having an ethylenically unsaturated bond, preferably having a (meth)acrylate structure compound. The polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds, more preferably a polymerizable compound having 5 to 6 ethylenically unsaturated bonds.

Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, and 2-ethylhexyl carbitol acrylate. , 2-hydroxyethyl acrylate, N-vinylpyrrolidone, (a), (b) and (c) above. Examples of polymerizable compounds having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol Di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloxyethyl)ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate. Examples of polymerizable compounds having three or more ethylenically unsaturated bonds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, di Pentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetra Pentaerythritol nona(meth)acrylate, tris(2-(meth)acryloxyethyl)isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified di 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 to 2900, more preferably 250 to 1500.

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, more preferably 10 to 60% by mass based on the total amount of solid content. % by mass, more preferably 13 to 60% by mass, 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 20:80~80:20, preferably 35: 65~80: 20. When content of a polymeric compound (C) exists in the said range, there exists a tendency for the residual film rate at the time of color pattern formation and the chemical resistance of a color filter to improve.

<Polymerization Initiator (D)>

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

Examples of the polymerization initiator (D) include O-acyl oxime compounds, alkyl phenone compounds, triazine compounds, acyl phosphine oxide compounds, and biimidazole compounds.

Examples of O-acyl oxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy -1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3- Cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl ]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxa Cyclopentylmethoxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-(2- Methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine and N-benzoyloxy-1-[9-ethyl-6-(2 -methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine. Commercially available items such as Irgacure (registered trademark) OXE01 and OXE02 (the above are manufactured by BASF Corporation), and N-1919 (manufactured by ADEKA Corporation) can be used. Among them, preferably selected from N-benzoyloxy-1-(4-phenylsulfanylphenyl) butane-1-one-2-imine, N- Benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl At least one of -3-cyclopentylpropane-1-one-2-imine, more preferably N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- 1-keto-2-imine.

Alkyl phenyl ketone compounds include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl)-2-benzylbutan-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4 -(4-morpholinyl)phenyl]butan-1-one. Commercial items such as Irgacure 369, 907, and 379 (the above are manufactured by BASF Corporation) can be used.

Alkyl phenyl ketone compounds, which can be 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy) Phenyl]propan-1-one, oligomers of 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α, Alpha-diethoxyacetophenone and benzoyl dimethyl ketal.

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

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercial items such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) can be used.

As the biimidazole compound, specifically, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3 -dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to 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. 48-38403, Japanese Patent Laid-Open 62-174204, etc.) and imidazole compounds in which the phenyl at the 4,4', 5,5'-position is substituted by an alkoxycarbonyl group (for example, refer to JP-A-7-10913, etc.). Among them, compounds represented by the following formulas and mixtures thereof are preferred.

Examples of other polymerization initiators include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl Benzoin compounds such as base ethers; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide , 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone and other benzophenone compounds; 9,10- Quinone compounds such as phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzoyl, methyl phenylglyoxylate, titanocene compounds, etc. These are preferably used in combination with a polymerization initiation adjuvant (especially an amine-based polymerization initiation adjuvant) 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 30 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). 30 parts by mass, particularly preferably 1 to 20 parts by mass.

<Polymerization Initiation Auxiliary>

The polymerization initiation adjuvant is a compound or a sensitizer for accelerating the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D). When the colored curable resin composition of this invention contains a polymerization initiation adjuvant, it is used together normally with a polymerization initiator (D).

Examples of the polymerization initiation adjuvant include an amine-based polymerization initiation adjuvant, an alkoxyanthracene-based polymerization initiation adjuvant, a thioxanthone-based polymerization initiation adjuvant, and a carboxylic acid-based polymerization initiation adjuvant.

Examples of amine-based polymerization initiation aids include alkanolamines such as triethanolamine, methyldiethanolamine, and triisopropanolamine; methyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoic acid Aminobenzoates such as ethyl ester, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate ; N,N-Dimethyl-p-toluidine; 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis(ethyl (methylamino)benzophenones, among which, alkylaminobenzophenones such as 4,4'-bis(diethylamino)benzophenone are preferable. Among them, alkylaminobenzophenones are preferred, and 4,4'-bis(diethylamino)benzophenone is preferred. Commercial items such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used.

Examples of alkoxyanthracene-based polymerization initiation aids include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2- Ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene and 2-ethyl-9,10-dibutoxyanthracene.

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

Examples of carboxylic acid-based polymerization initiation aids include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethyl Phenylsulfanyl acetic acid, methoxyphenylsulfanyl acetic acid, dimethoxyphenylsulfanyl acetic acid, chlorophenylsulfanyl acetic acid, dichlorophenylsulfanyl acetic acid, N-phenylglycerin Amino acid, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthyloxyacetic acid.

When using a polymerization initiation adjuvant, the content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When content of a polymerization start adjuvant exists in this range, a colored pattern can be formed with higher sensitivity, and the productivity of a color filter tends to improve.

<Solvent (E)>

The solvent (E) is not limited, and solvents generally used in the field can be used alone or in combination of two or more. Specifically, ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (in Solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (containing OH in the molecule, not containing -O-, - CO- and -COO- solvents), aromatic hydrocarbon solvents, amide solvents, and dimethylsulfoxide.

Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, propyl Butyl Butyrate, Isopropyl Butyrate, Ethyl Butyrate, Butyl Butyrate, Methyl Pyruvate, Ethyl Pyruvate, Propyl Pyruvate, Methyl Acetyl Acetate, Ethyl Acetyl Acetate, Cyclohexanol Acetate and gamma-butyrolactone.

Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monomethyl ether, and diethylene glycol monomethyl ether. 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-methoxy 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, phenetole, and methyl anisole.

Examples of ether ester solvents include methyl methoxyacetate, methyl Ethyl oxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, 3-ethyl Methyl oxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, 2-ethyl Methyl oxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methylpropionate Oxybutyl 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 ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, and 4-methyl-2-pentanone ketone, cyclopentanone, cyclohexanone, and isophorone.

As the alcohol solvent, methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin are exemplified.

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

As the amide solvent, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone can be cited.

These solvents may combine 2 or more types.

Among the solvents described above, organic solvents having a boiling point at 1 atm (atmospheric pressure) of 120° C. or higher and 210° C. or lower are preferable from the viewpoint of coating properties and drying properties. Among them, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, 3-ethoxy ethyl propionate, ethylene glycol monomethyl ether Diethylene 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, 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 within the above range, the flatness at the time of coating becomes favorable, and the color density does not become insufficient when forming a color filter, so the display characteristics tend to become favorable.

<Leveling agent>

Examples of the leveling agent include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may have a polymerizable group in a side chain.

DC3PA、SH7PA、DC11PA、SH21PA、SH28PA、SH29PA、SH30PA、SH8400(東麗-道康寧(株)製造)、KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化學工業(株)製造)、TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF4446、TSF4452和TSF4460(

‧

‧

‧

合同會社製造)等。 Examples of silicone-based surfactants include surfactants having a siloxane bond in the molecule. Specifically, it can be cited

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 manufacturing), etc.

(註冊商標)FC430、FC431(住友3M(株)製造)、

(註冊商標)F142D、F171、F172、F173、F177、F183、F554、R30、RS-718-K(DIC(株)製造)、

(註冊商標)EF301、EF303、EF351、EF352(三菱

電子化成(株)製造)、

(註冊商標)S381、S382、SC101、SC105(旭硝子(株)製造)和E5844((株)

研究所製造)。 Examples of the fluorine-based surfactant include those having a fluorocarbon chain in the molecule. Specifically, it can be cited

(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 Co., Ltd.),

(registered trademark) EF301, EF303, EF351, EF352 (Mitsubishi

manufactured by Denshi Kasei Co., Ltd.),

(registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 ((Co., Ltd.)

manufactured by the Institute).

(註冊商標)R08、BL20、F475、F477和F443(DIC(株)製造)。 Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, it can be cited

(registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Co., Ltd.).

The content of the leveling agent is usually not less than 0.0005 mass % and not more than 0.6 mass %, preferably not less than 0.001 mass % and not more than 0.5 mass %, more preferably not less than 0.001 mass % and not more than the total amount of the colored curable resin composition. 0.2 mass % or less, more preferably 0.002 mass % or more and 0.1 mass % or less, particularly preferably 0.005 mass % or more and 0.07 mass % or less. The flatness of a color filter can be made favorable that content of a leveling agent exists in the said range.

<other ingredients>

The colored curable resin composition of the present invention may contain fillers, other polymer compounds, adhesion promoters, antioxidants, Additives known in the technical field such as light stabilizers and chain transfer agents.

<Manufacturing method of colored curable resin composition>

The colored curable resin composition of the present invention can be obtained by, for example, adding a compound (colorant (A1)), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E) and, if necessary, It is prepared by mixing leveling agent, polymerization initiation aid and other ingredients. In addition to the colorant (A1), colorants (A2) such as pigments and dyes can also be further mixed. The pigment is preferably mixed with part or all of the solvent (E) in advance, and dispersed using a bead mill or the like until the pigment has an average particle diameter of about 0.2 μm or less and is used in the state of a pigment dispersion. At this time, 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.

<Manufacturing method of color filter>

As a method of manufacturing a colored pattern from the colored curable resin composition of this invention, a photolithography method, an inkjet method, a printing method, etc. are mentioned. Among them, photolithography is preferable. The photolithography method is a method of applying a colored curable resin composition to a substrate, drying it to form a colored composition layer, exposing the colored composition layer through a photomask, and developing it. In photolithography, a colored coating film that is a cured product of the above-mentioned colored composition layer can be formed by not using a photomask and/or not developing during exposure. The colored pattern and colored coating film formed in this way are the color filter of this invention.

The film thickness of the produced color filter can be appropriately adjusted according to the purpose, application, etc., and is usually 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably Selected as 0.5~6μm.

As the substrate, a glass plate, a resin plate, silicon, or a thin film of aluminum, silver, silver/copper/palladium alloy, etc. formed on the above substrate can be used. Additional color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates.

The formation of pixels of each color by photolithography can be performed under known or commonly used equipment and conditions. For example, it can be produced as follows.

First, a colored curable resin composition is applied on a substrate, and dried by heat drying (prebaking) and/or reduced pressure drying to remove volatile components such as solvents and obtain a smooth colored composition layer. As the coating method, a spin coating method, a slit coating method, and a slit and spin coating method are exemplified.

Next, the colored composition layer is exposed through a photomask for forming a targeted colored pattern. Since it is possible to uniformly irradiate the entire exposure surface with parallel light rays and accurately align the photomask and the substrate on which the colored composition layer is formed, it is preferable to use exposure devices such as a mask aligner and a stepper. A colored pattern is formed on a board|substrate by making the exposed coloring composition layer contact a developing solution, and developing. By image development, the unexposed part of a coloring composition layer dissolves in a developing solution, and is removed. The developer is preferably an aqueous solution of a basic compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, tetramethylammonium hydroxide, or the like. The developing method may be any of spin-dip method, dip method and spray method. Furthermore, the substrate can be inclined at any angle during image development. Water washing is preferably performed after image development.

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

The color filter formed from the colored curable resin composition of this invention can be used as a color filter used for a display device (for example, a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state imaging element.

Example

Next, examples will be given to describe the present invention more specifically. In the examples, % and parts indicating the content or usage amount are based on mass unless otherwise specified.

[Example 1]

400 parts of methanol were added to 5.0 parts of the compound represented by formula (1-1), and it stirred at 20-30 degreeC for 1 hour, and obtained the solution. 400 parts of ion-exchanged water was added to this solution, and it stirred for 2 hours, and obtained the 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 3 hydrogen, and stirred at 20°C to 30°C for 1 hour. Next, 28.8 parts of methanol were added and stirred for 2 hours to obtain a solution (1- 1B). Solution (1-1B) and 1.0 parts of barium chloride were added to solution (1-1A), and it stirred at 20 to 30 degreeC for 24 hours. The generated 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) compound synonym).

[Synthesis of resin]

Into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was flowed to make it a nitrogen atmosphere, 100 parts of propylene glycol monomethyl ether acetate was charged, and it was heated to 85° C. while stirring. Next, 19 parts of methacrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and Mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-9-yl ester (50:50 by molar ratio) (trade name "E-DCPA", Daicel Co., Ltd. A solution in which 171 parts of propylene glycol monomethyl ether acetate was dissolved in 40 parts of propylene glycol monomethyl ether acetate. On the other hand, 26 parts of polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in propylene glycol monomethylvaleronitrile by dropping into the flask over about 5 hours using a separate drip pump. A solution in 120 parts of ether acetate. After completion of dropping the polymerization initiator, it was kept at the same temperature for about 3 hours, and then cooled to room temperature to obtain a solution of a copolymer and resin (B-1) having a solid content of 43.5%. The obtained resin (B-1) had a weight average molecular weight of 8000, 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 weight average molecular weight (Mw) and the number average molecular weight (Mn) of the polystyrene conversion of resin was performed on 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

Concentration of detected liquid and solid components: 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 Co., Ltd.)

The weight average molecular weight and number average molecular weight in terms of polystyrene obtained above were divided into The molecular weight ratio (Mw/Mn) was used as the molecular weight distribution.

[Preparation of colored curable resin composition]

Example 2

(註冊商標)F554(DIC(株)製造)0.1份混合，得到了著色固化性樹脂組合物。 Compound (A1): 0.8 parts of a compound represented by formula (1-1P); alkali-soluble resin (B): 50 parts of resin (B-1) (in terms of solid content); polymerizable compound (C): dipentaerythritol hexa Acrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts; polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl) octane 10 parts of alkan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation; O-acyl oxime compound); solvent (E): 700 parts of 1-methyl-2-pyrrolidone; and leveling agent (F):

(registered trademark) F554 (manufactured by DIC Corporation) 0.1 part was mixed to obtain a colored curable resin composition.

Comparative example 1

(註冊商標)F554(DIC(株) 製造)0.1份混合，得到了著色固化性樹脂組合物。 Dye (A1): 0.6 parts of the compound represented by formula (1-1); alkali-soluble resin (B): 50 parts of resin (B-1) (in terms of solid content); polymerizable compound (C): dipentaerythritol hexa Acrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts; polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl) octane 10 parts of alkan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyl oxime compound); solvent (E): 700 parts of propylene glycol monomethyl ether acetate; and leveling agent (F):

(registered trademark) F554 (manufactured by DIC Corporation) 0.1 part was mixed to obtain a colored curable resin composition.

[pattern formation]

XG；康寧公司製造)上採用旋塗法塗布著色固化性樹脂組合物後，在100℃下預烘焙3分鐘，得到了組合物層。冷卻後，使形成了組合物層的玻璃基板與石英玻璃制光掩模的間隔成為100μm，使用曝光機(TME-150RSK；

(株)製造)在大氣氣氛下、以150mJ/cm2的曝光量(365nm基準)進行光照射。作為光掩模，使用形成了100μm線和間隙圖案的光掩模。光照射後，將上述塗膜在包含非離子系表面活性劑0.12%和氫氧化鉀0.04%的水系顯影液中在23℃下浸漬顯影80秒，水洗後，在烘箱中、220℃下進行20分鐘後烘焙，得到了圖案。 On a 2-inch square glass substrate (

XG; manufactured by Corning Incorporated) was coated with a colored curable resin composition by a spin coating method, 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 photomask made of quartz glass was 100 μm, and an exposure machine (TME-150RSK;

(manufactured by Co., Ltd.) was irradiated with light at an exposure dose of 150 mJ/cm 2 (based on 365 nm) in an air atmosphere. As the photomask, a photomask formed with a 100 μm line and space pattern was used. After light irradiation, the above-mentioned coating film was dipped and developed in an aqueous developer solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 23°C for 80 seconds, washed with water, and then dried in an oven at 220°C for 20 seconds. Minutes after baking, the pattern is obtained.

[Evaluation of heat resistance]

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 colorimeter (OSP-SP-200; manufactured by OLYMPUS). As a result of evaluating the heat resistance of the coating film obtained in Example 2, the color difference (ΔEab*) was 4.3. In addition, when heat resistance was evaluated in the same manner as Comparative Example 1, the color difference (ΔEab*) was 12.9, indicating that the compound of the present application is excellent in heat resistance.

Industrial availability

When the colored curable resin composition containing this compound is used, the coating film which has favorable heat resistance can be provided. The coating film can be used in display devices (such as liquid crystal display devices, organic EL devices, electronic paper etc.) and color filters used in solid-state imaging devices.

Claims (5)

A compound characterized by comprising: a compound (a) having cations and anions with the same number of charges in the molecule; at least one element selected from tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements anion (b); and an alkaline earth metal-containing cation (c), wherein the compound (a) is a compound represented by formula (a1-1),

In the formula (a1-1), R ¹ to R ⁴ independently represent a hydrogen atom, an aromatic hydrocarbon group with a carbon number of 6 to 10 that may have a substituent, or a saturated hydrocarbon group with a carbon number of 1 to 20 that may have a substituent, and the The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group can be replaced by -O-, -CO-, -N(R ¹⁰ )-, -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 terminal -CH ₂ - will not be replaced, R ¹ and R ² can form together A nitrogen atom ring, R ³ and R ⁴ can form a nitrogen atom ring together, R ⁵ and R ⁶ independently represent a hydrogen atom or an alkyl group with a carbon number of 1 to 6, R ¹⁰ represents a hydrogen atom, a carbon number of 1 to 6 20 saturated hydrocarbon group or aralkyl group with 7~10 carbons. The compound according to claim 1, wherein the cation (c) is at least one selected from magnesium cations, calcium cations, strontium cations and barium cations. A colored curable resin composition comprising the compound according to claim 1 or 2, resin, polymerizable compound and polymerization initiator. A color filter formed from the colored curable resin composition according to claim 3. A liquid crystal display device having the color filter according to Claim 4.