TWI856975B - Compound, colored resin composition, color filter and display device - Google Patents

Abstract

The present invention provides compounds of formulas (IA), (IB), (IC), or (ID) having improved thermal stability, and a colored resin composition, a color filter and display device comprising the same.

Description

Compound, coloring resin composition, color filter and display device

The present invention relates to a compound.

Color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays, and solid-state imaging devices such as CCD (Charge-Coupled Device) and CMOS (Complementary Metal-Oxide-Semiconductor) sensors are manufactured from a coloring resin composition. In such a coloring resin composition, a pigment is used as a coloring agent. Furthermore, although the use of the pigment in the resin composition is unknown, a compound represented by formula (i), i.e., CI Pigment Blue 24 (Non-patent Document 1), is known as a pigment.

[Prior technical literature] [Non-patent literature] [Non-patent literature 1] Colour Index International (British Society of Dyers and Colorists, American Society of Fiber Chemists and Colorists)

[Problem to be solved by the invention]

However, the conventionally known C.I. pigment blue 24 has low heat resistance and is not suitable for a coloring resin composition for forming a color filter. In view of this, the present invention provides a compound having excellent heat resistance. [Means for solving the problem]

The present invention includes the following inventions.

[1] A compound represented by formula (IA), formula (IB), formula (IC), or formula (ID): [In formula (IA), ^RA1 to ^RA10 each independently represent a hydrogen atom, a hydroxyl ^group , _-CO2- ^, _-SO3- , ^-O- , a group represented by formula (a), or a alkyl group having 1 to 20 carbon atoms which may have a substituent, and at least two of ^RA1 to ^RA10 represent _-CO2- ^, _-SO3- , ^{-O- ,} or a group represented by formula (a). (In formula (a), ^RA11 represents a hydrogen atom or a carbon number of 1 to 20 which may have a substituent. ^LA1 represents a divalent aromatic carbon group which may have a substituent. Aa ^㊀ represents -CO ₂ ^- or -SO ₃ ^- . However, the * in the formula means a bond terminal.) ^TA1 represents an aromatic carbon group which may have a substituent and has a carbon number of 6 to 10. However, the aromatic carbon group does not have -SO ₃ ^- as a substituent. An represents the sum of the numbers of -CO ₂ ^- , -SO ₃ ^- , and -O ^- possessed by the compound represented by formula (IA). Am represents an integer greater than 1. ^{AXAk ㊉} represents a metal cation with an Ak valence. Ak represents an integer greater than 2. ] [In formula (IB), ^RB1 to ^RB10 each independently represent a hydrogen atom, a hydroxyl ^group , _-CO2- ^, _-SO3- , ^-O- , a group represented by formula (b), or a alkyl group having 1 to 20 carbon atoms which may have a substituent, and at least two of ^RB1 to ^RB10 represent _-CO2- ^, _-SO3- , ^{-O- ,} or a group represented by formula (b). (In formula (b), ^RB11 represents a hydrogen atom or a carbon number of 1 to 20 which may have a substituent. ^LB1 represents a divalent aromatic carbon group which may have a substituent. ^Bb represents _-CO2- or ^-SO3- . However, the * in the formula means a bond terminal.) Bn represents the sum of the numbers of _-CO2- ^, _-SO3- ^, and ^-O- possessed by the compound represented by formula (IB). ^TB1 represents a divalent aromatic carbon group which may have ^a carbon number of 6 to 14 which may have a substituent. However, the _aromatic carbon group does not have _-SO3- as a ^substituent . ^LB0 represents a Bm-valent linking group. Bm represents an integer greater than 2. ^{BXBk represents} a Bk-valent metal cation. Bk represents an integer greater than 1. ] [In formula (IC), ^RC1 to ^RC4 each independently represent a hydrogen atom or a alkyl group having 1 to 20 carbon atoms which may have a substituent. ^RC5 to ^RC12 each independently represent a hydrogen atom or a alkyl group having 1 to 8 carbon atoms. ^TC1 represents a trivalent aromatic alkyl group having 6 to 14 carbon atoms which may have a substituent. CX ^Ck represents a metal cation having a ^valence of Ck. Ck represents an integer greater than 1.] [In formula (ID), ^RD1 to ^RD10 each independently represent a hydrogen atom, a hydroxyl ^group , _-CO2- ^, _-SO3- , ^-O- , a group represented by formula (d), or a alkyl group having 1 to 20 carbon atoms which may have a substituent, and at least two of ^RD1 to ^RD10 represent _-CO2- ^, _-SO3- , ^{-O- ,} or a group represented by formula (d). (In formula (d), ^RD11 represents a hydrogen atom or a alkyl group having 1 to 20 carbon atoms which may have a substituent. ^LD1 represents a divalent aromatic alkyl group which may have a substituent. Dd ^㊀ represents -CO ₂ ^- or -SO ₃ ^- . However, * in the formula means a bond terminal.) ^TD1 represents a divalent aromatic alkyl group having 6 to 10 carbon atoms which may have a substituent. However, the aromatic alkyl group does not have -SO ₃ ^- as a substituent. ^RD21 represents a hydrogen atom or a alkyl group having 1 to 20 carbon atoms which may have a substituent. DX ^㊉ represents a monovalent metal cation. ]

[2] A coloring resin composition comprising a coloring agent and a resin, wherein the coloring agent comprises at least one selected from the group consisting of a compound represented by formula (IA), a compound represented by formula (IB), a compound represented by formula (IC), and a compound represented by formula (ID) as described in [1].

[3] A coloring resin composition comprising the coloring resin composition as described in [2], a polymerizable compound, and a polymerization initiator.

[4] A color filter formed from the colored resin composition as described in [3].

[5] A display device comprising the color filter as described in [4]. [Effect of the invention]

According to the present invention, a novel compound having excellent heat resistance can be provided. In addition, the compound according to the present invention can form a color filter having excellent heat resistance.

>Compounds>

The compound involved in the present invention is a compound represented by formula (IA) (hereinafter, sometimes referred to as compound (IA)), a compound represented by formula (IB) (hereinafter, sometimes referred to as compound (IB)), a compound represented by formula (IC) (hereinafter, sometimes referred to as compound (IC)), or a compound represented by formula (ID) (hereinafter, sometimes referred to as compound (ID)). Although formula (IA), formula (IB), formula (IC), or formula (ID) is used to explain the present invention in detail below, compound (IA), compound (IB), compound (IC), or compound (ID) includes tautomers of formula (IA), formula (IB), formula (IC), or formula (ID), and includes compounds obtained by rotating each group in formula (IA), formula (IB), formula (IC), or formula (ID) about the bond axis of a carbon-carbon single bond.

>>Compound (IA)>>

A compound represented by formula (IA). [In formula (IA), ^RA1 to ^RA10 each independently represent a hydrogen atom, a hydroxyl ^group , _-CO2- ^, _-SO3- , ^-O- , a group represented by formula (a), or a alkyl group having 1 to 20 carbon atoms which may have a substituent, and at least two of ^RA1 to ^RA10 represent _-CO2- ^, _-SO3- , ^{-O- ,} or a group represented by formula (a). (In formula (a), ^RA11 represents a hydrogen atom or a carbon number of 1 to 20 which may have a substituent. ^LA1 represents a divalent aromatic carbon group which may have a substituent. Aa ^㊀ represents -CO ₂ ^- or -SO ₃ ^- . However, the * in the formula means a bond terminal.) ^TA1 represents an aromatic carbon group which may have a substituent and has a carbon number of 6 to 10. However, the aromatic carbon group does not have -SO ₃ ^- as a substituent. An represents the sum of the numbers of -CO ₂ ^- , -SO ₃ ^- , and -O ^- possessed by the compound represented by formula (IA). Am represents an integer greater than 1. ^{AXAk ㊉} represents a metal cation with an Ak valence. Ak represents an integer greater than 2. ]

Examples of the carbonyl group having 1 to 20 carbon atoms represented by ^RA1 to ^RA10 and ^RA11 include an aliphatic carbonyl group having 1 to 20 carbon atoms and an aromatic carbonyl group having 6 to 20 carbon atoms.

The aliphatic hydrocarbon group having 1 to 20 carbon atoms may be saturated or unsaturated, and may be linear, branched, or cyclic.

Examples of the linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms include linear aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, vinyl, 1-propenyl, 2-propenyl (allyl); and branched aliphatic hydrocarbon groups such as isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl.

The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic aliphatic hydrocarbon group include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include phenyl, thiophene, trimethylphenyl, dipropylphenyl, di(2,2-dimethylpropyl)phenyl, and naphthyl.

Substituents that may be possessed by the alkyl group having 1 to 20 carbon atoms represented by ^RA1 to ^RA10 and ^RA11 include halogen atoms such as fluorine, chlorine and iodine atoms; hydroxyl groups; carboxyl groups; sulfamoyl groups; nitro groups; alkoxy groups having 1 to 10 carbon atoms such as methoxy and ethoxy groups; and alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl groups.

The divalent aromatic hydrocarbon group represented by L ^A1 is preferably a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and includes groups having one of the hydrogen atoms contained in the monovalent aromatic hydrocarbon groups among ^RA1 to ^RA10 and ^RA11 as a bonding terminal.

The substituents which the divalent aromatic hydrocarbon group represented by ^LA1 may have are the same as the substituents which the hydrocarbon groups having 1 to 20 carbon atoms represented by ^RA1 to ^RA10 and ^RA11 may have.

When compound (IA) has a plurality of groups represented by formula (a), and when a plurality of R ^A11 , L ^A1 , and Aa ^㊀ exist in compound (IA), they may be the same or different.

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms represented by ^TA1 include phenyl, phthalyl, trimethylphenyl, naphthyl and the like.

Substituents that the aromatic hydrocarbon group having 6 to 10 carbon atoms represented by ^TA1 may have include: halogen atoms such as fluorine atom, chlorine atom and iodine atom; hydroxyl group; carboxyl group; sulfonamide group; ^-NRxRy ( ^Rx and ^Ry are each independently a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent); nitro group; alkoxy groups having 1 to 10 carbon atoms such as methoxy and ethoxy ^groups ; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl groups, etc.

Specific examples of the carbonyl group having 1 to 20 carbon atoms represented by ^Rx and ^Ry , and the substituent which the carbonyl group may have, are the same as those for ^RA1 to ^RA10 and ^RA11 .

Among the metal cations with an Ak value represented by AX ^{Ak ㊉} , examples of metals with an Ak value of 2 (i.e., divalent metals) include alkaline earth metals such as magnesium, calcium, strontium, and barium, and transition metals such as zinc, copper, nickel, and manganese; examples of metals with an Ak value of 3 (i.e., trivalent metals) include typical metals such as aluminum, and transition metals such as cobalt and iron.

As compound (IA), preferably, ^RA1 to ^RA10 , ^TA1 , An, Am, and AX ^{Ak are as} described below.

In ^RA1 to ^RA10 , the number of -CO ₂ ^- , -SO ₃ ^- , -O ^- or the group represented by formula (a) is preferably 2 to 6, more preferably 2 to 4, and further preferably 2 to 3. In other words, An is preferably 2 to 6, more preferably 2 to 4, and further preferably 2 to 3. When there are two or more -CO ₂ ^- , -SO ₃ ^- , -O ^- or a group represented by formula (a) among ^RA1 to ^RA10 , it is preferred that at least one of ^RA1 to ^RA6 is -CO ₂ ^- , -SO ₃ ^- , -O ^- or a group represented by formula (a), and at least one of ^RA7 to ^RA10 is -CO ₂ ^- , -SO ₃ ^- , -O ^- or a group represented by formula (a).

When compound (IA) has a substituent represented by formula (a), it is preferred that at least two of ^RA1 to ^RA10 are groups represented by formula (a); it is more preferred that two to four of ^RA1 to ^RA10 are groups represented by formula (a) and do not have -CO ₂ ^- , -SO ₃ ^- , or -O ^- ; it is further preferred that two of ^RA1 to ^RA10 are groups represented by formula (a) and do not have -CO ₂ ^- , -SO ₃ ^- , or -O ^- . In addition, when compound (IA) has a plurality of groups represented by formula (a), it is preferred that the plurality of groups represented by formula (a) are the same.

The group represented by formula (a) is preferably a group in which L ^A1 is a phenylene methylene group, a methylphenylene methylene group, or a dimethylphenylene methylene group which may have a substituent. More preferably, L ^A1 is a phenylene methylene group, a methylphenylene methylene group, or a dimethylphenylene methylene group which does not have a substituent, ^RA11 is a hydrogen atom or a saturated hydrocarbon group having 1 to 2 carbon atoms which does not have a substituent, and ^Aa is -SO ₃ ^- .

As the group represented by the formula (a), for example, the groups represented by the following formulae (a-1) to (a-8) can be cited. (The * in the formula refers to the bond end.)

When compound (IA) has no substituent represented by formula (a), it is preferred that at least two of ^RA1 to ^RA10 are -CO ₂ ^- or -O ^- , more preferably that two to four of ^RA1 to ^RA10 are -CO ₂ ^- or -O ^- , and further preferably that two of ^RA1 to ^RA10 are -CO ₂ ^- and one of ^RA1 to ^RA10 is -O ^- .

The group other than -CO ₂ ^- , -SO ₃ ^- , -O ^- and the group represented by formula (a) represented by ^RA1 to ^RA10 is preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or a linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, further preferably a hydrogen atom or a linear aliphatic hydrocarbon group having 1 to 5 carbon atoms, and further preferably a hydrogen atom or a methyl group.

In ^RA1 to ^RA10 , the number of hydrogen atoms is preferably 4 to 8, more preferably 6 to 8.

T ^A1 is preferably a phenyl group which may have a substituent; more preferably a phenyl group having a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, or -NR ^x R ^y as a substituent; further preferably a phenyl group having a chlorine atom or -NR ^x R ^y as a substituent.

In the above- ^{NRxRy , Rx} is preferably a hydrogen atom, and ^Ry is a alkyl group having 1 to 10 carbon atoms which may have a substituent, more preferably an aromatic alkyl group having 6 to 10 carbon atoms which may have a substituent, ^and further ^preferably an aromatic alkyl group having 6 to 10 carbon atoms which has an alkoxy group having 1 to 5 carbon atoms as a substituent.

Examples of T ^A1 include groups represented by the following formulae (aa-1) to (aa-8). (The * in the formula refers to the key end.)

Am is preferably 2 to 5, more preferably 2 to 3, and further preferably 2.

The Ak-valent metal cation represented by AX ^{Ak ㊉} is preferably a cation of a metal having an Ak of 2 to 3 (i.e., a divalent to trivalent metal), and more preferably a cation of barium, zinc, or manganese, which is a metal having an Ak of 2 (i.e., a divalent metal).

Examples of the compound (IA) include compounds represented by formula (A-1) to formula (A-27) shown in Table 1.

[Table 1]

In Table 1, Me represents a methyl group; a-6, aa-1, aa-2, and aa-6 respectively mean groups represented by the above formulae (a-6), (aa-1), (aa-2), and (aa-6).

>>Compound (IB)>>

A compound represented by formula (IB). [In formula (IB), ^RB1 to ^RB10 each independently represent a hydrogen atom, a hydroxyl ^group , _-CO2- ^, _-SO3- , ^-O- , a group represented by formula (b), or a alkyl group having 1 to 20 carbon atoms which may have a substituent, and at least two of ^RB1 to ^RB10 represent _-CO2- ^, _-SO3- , ^{-O- ,} or a group represented by formula (b). (In formula (b), ^RB11 represents a hydrogen atom or a carbon number of 1 to 20 which may have a substituent. ^LB1 represents a divalent aromatic carbon group which may have a substituent. ^Bb represents _-CO2- or ^-SO3- . However, the * in the formula means a bond terminal.) Bn represents the sum of the numbers of _-CO2- ^, _-SO3- ^, and ^-O- possessed by the compound represented by formula (IB). ^TB1 represents a divalent aromatic carbon group which may have ^a carbon number of 6 to 14 which may have a substituent. However, the _aromatic carbon group does not have _-SO3- as a ^substituent . ^LB0 represents a Bm-valent linking group. Bm represents an integer greater than 2. ^{BXBk represents} a Bk-valent metal cation. Bk represents an integer greater than 1. ]

Examples of the carbonyl group having 1 to 20 carbon atoms represented by ^RB1 to ^RB10 and ^RB11 include an aliphatic carbonyl group having 1 to 20 carbon atoms and an aromatic carbonyl group having 6 to 20 carbon atoms.

The aliphatic hydrocarbon group having 1 to 20 carbon atoms may be saturated or unsaturated, and may be linear, branched, or cyclic.

Examples of the linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms include linear aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, vinyl, 1-propenyl, 2-propenyl (allyl); and branched aliphatic hydrocarbon groups such as isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl.

The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic, or may be an aliphatic hydrocarbon group containing two or more aliphatic hydrocarbon rings. Examples of the cyclic aliphatic hydrocarbon group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, ethylcyclohexyl, dimethyl norbornane, and dimethyl norbornane. A hydrogen atom of dimethyladamantane becomes a bond-terminal group, a hydrogen atom of diethyladamantane becomes a bond-terminal group, a hydrogen atom of di(methylcyclohexyl)methane becomes a bond-terminal group, a hydrogen atom of di(ethylcyclohexyl)methane becomes a bond-terminal group, a hydrogen atom of di(dimethylcyclohexyl)methane becomes a bond-terminal group, a hydrogen atom of di(dimethylcyclohexyl)methane becomes a bond-terminal group, a hydrogen atom of di(dimethylcyclohexyl)methane becomes a bond-terminal group, One hydrogen atom of alkane becomes a bond-terminal group, one hydrogen atom of di(diethylcyclohexyl)methane becomes a bond-terminal group, one hydrogen atom of di(trimethylcyclohexyl)methane becomes a bond-terminal group, one hydrogen atom of di(triethylcyclohexyl)methane becomes a bond-terminal group, one hydrogen atom of di(methylcyclohexyl)dimethylmethane becomes a bond-terminal group, one hydrogen atom of di(ethylcyclohexyl)dimethylmethane becomes a bond-terminal group, etc.

Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include phenyl, thiophene, trimethylphenyl, dipropylphenyl, di(2,2-dimethylpropyl)phenyl, and naphthyl.

Substituents that may be possessed by the alkyl group having 1 to 20 carbon atoms represented by ^RB1 to ^RB10 and ^RB11 include halogen atoms such as fluorine, chlorine and iodine atoms; hydroxyl groups; carboxyl groups; sulfonamide groups; nitro groups; alkoxy groups having 1 to 10 carbon atoms such as methoxy and ethoxy groups; and alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl groups.

The divalent aromatic hydrocarbon group represented by L ^B1 is preferably a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and includes a group having one of the hydrogen atoms contained in the monovalent aromatic hydrocarbon groups among R ^B1 to R ^B10 and R ^B11 (excluding the aromatic hydrocarbon group having 11 to 20 carbon atoms) as a bond terminal.

The substituents which the divalent aromatic hydrocarbon group represented by L ^B1 may have are the same as the substituents which the hydrocarbon groups having 1 to 20 carbon atoms represented by ^RB1 to ^RB10 and ^RB11 may have.

When compound (IB) has a plurality of groups represented by formula (b), and a plurality of R ^B11 , L ^B1 , and Bb ^㊀ exist in compound (IB), they may be the same or different.

As the divalent aromatic hydrocarbon group having 6 to 14 carbon atoms represented by ^TB1 , there can be cited a group having one of the hydrogen atoms contained in the monovalent aromatic hydrocarbon groups among ^RB1 to ^RB10 and ^RB11 (excluding the aromatic hydrocarbon group having 15 to 20 carbon atoms) as a bond terminal.

Specific examples of the substituent which the divalent aromatic hydrocarbon group having 6 to 14 carbon atoms represented by ^TB1 may have are the same as the substituent which the hydrocarbon group having 1 to 20 carbon atoms represented by ^RB1 to ^RB10 and ^RB11 may have.

The Bm-valent linking group represented by L ^B0 is preferably a divalent to pentavalent hydrocarbon group having 1 to 20 carbon atoms, wherein a portion of -CH ₂ - contained in the hydrocarbon group may be replaced by an oxygen atom or a sulfur atom, or a portion of >CH- contained in the hydrocarbon group may be replaced by a nitrogen atom. More preferably, it is a divalent to pentavalent hydrocarbon group having 1 to 20 carbon atoms, wherein a portion of -CH ₂ - contained in the hydrocarbon group may be replaced by an oxygen atom or a sulfur atom, or a portion of >CH- contained in the hydrocarbon group may be replaced by a nitrogen atom, and at least one of the oxygen atom, sulfur atom, and nitrogen atom has all the bonding ends of the linking group. As the Bm-valent linking group, the following groups can be cited: a group having (Bm-1) hydrogen atoms contained in the monovalent carbon groups of ^RB1 to ^RB10 and ^RB11 as bonding ends, a part of _-CH2- contained in the carbon group can be replaced by an oxygen atom or a sulfur atom, and a part of >CH- contained in the carbon group can be replaced by a nitrogen atom.

Among the metal cations with a Bk value represented by BX ^{Bk ㊉} , examples of metals with a Bk value of 1 (i.e., monovalent metals) include alkaline metals such as lithium, sodium, potassium, and cesium; examples of metals with a Bk value of 2 (i.e., divalent metals) include alkaline earth metals such as magnesium, calcium, strontium, and barium, and transition metals such as zinc, copper, nickel, and manganese; examples of metals with a Bk value of 3 (i.e., trivalent metals) include typical metals such as aluminum, and transition metals such as cobalt and iron.

As compound (IB), ^RB1 to ^RB10 , Bn, ^TB1 , ^LB0 , Bm, and ^{BXBk are} preferably as follows.

Among ^RB1 to ^RB10 , the number of -CO ₂ ^- , -SO ₃ ^- , -O ^- or the group represented by formula (b) is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2. In other words, Bn is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2. Among ^RB1 to ^RB10 , when there are 2 or more -CO ₂ ^- , -SO ₃ ^- , -O ^- or the group represented by formula (b), it is preferred that at least one of ^RB1 to ^RB6 is -CO ₂ ^- , -SO ₃ ^- , -O ^- , or the group represented by formula (b), and at least one of ^RB7 to ^RB10 is -CO ₂ ^- , -SO ₃ ^- , -O ^- , or the group represented by formula (b).

When compound (IB) has a substituent represented by formula (b), it is preferred that at least two of ^RB1 to ^RB10 are groups represented by formula (b); it is more preferred that two to four of ^RB1 to ^RB10 are groups represented by formula (b) and do not have _-CO2- ^, _-SO3- , or ^-O- ; ^it is further preferred that two of ^RB1 to ^RB10 are groups represented by formula (b) and do not have _{-CO2-, -SO3-} ^{, or -O-} . In addition, when compound (IB) has a plurality of groups represented by formula (b), _it is preferred that the plurality of groups represented by formula (b) are the same.

The group represented by formula (b) is preferably a group in which L ^B1 is a phenylene methylene group, a methylphenylene methylene group or a dimethylphenylene methylene group which may have a substituent. More preferably, L ^B1 is a phenylene methylene group, a methylphenylene methylene group or a dimethylphenylene methylene group which does not have a substituent, ^RB11 is a hydrogen atom or a saturated hydrocarbon group having 1 to 2 carbon atoms which does not have a substituent, and ^Bb is -SO ₃ ^- .

As the group represented by the formula (b), for example, there can be mentioned groups represented by the following formulae (b-1) to (b-8). (The * in the formula refers to the key end.)

The groups other than -CO ₂ ^- , -SO ₃ ^- , -O ^- and the group represented by formula (b) represented by ^RB1 to ^RB10 are preferably each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or a linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, further preferably a hydrogen atom or a linear aliphatic hydrocarbon group having 1 to 5 carbon atoms, and further preferably a hydrogen atom or a methyl group.

Among ^RB1 to ^RB10 , the number of hydrogen atoms is preferably 4 to 8, more preferably 6 to 8.

T ^B1 is preferably a phenylene group or a naphthyl group which may have a substituent, and more preferably a phenylene group or a naphthyl group which does not have a substituent.

L ^B0 is preferably a divalent hydrocarbon group having 1 to 20 carbon atoms, more preferably a divalent saturated cyclic hydrocarbon group having 1 to 20 carbon atoms, further preferably a group in which a carbon atom contained in the saturated cyclic hydrocarbon group is replaced by a nitrogen atom, and further preferably the carbon atom replaced by the nitrogen atom is bonded to the carbon atom of ^TB1 .

As L ^B0 , for example, linking groups represented by the following formulae (LB-1) to (LB-8) can be cited. (The * in the formula refers to the key end.)

Bm is preferably 2 to 5, more preferably 2 to 3, and most preferably 2.

The Bk-valent metal cation represented by BX ^{Bk ㊉} is preferably a cation of a metal having a Bk of 1 to 3 (i.e., a 1-valent to 3-valent metal), and more preferably a cation of barium, zinc, or manganese, which is a metal having a Bk of 2 (i.e., a 2-valent metal).

Examples of the compound (IB) include compounds represented by formula (B-1) to formula (B-48) shown in Table 2.

[Table 2]

In Table 2, Me represents a methyl group, phe represents a phenylene group, naph represents a naphthylene group, and b-6, b-7, LB-3, and LB-4 respectively mean the groups represented by the above formulae (b-6), (b-7), (LB-3), and (LB-4).

>>Compounds (IC)>>

A compound represented by formula (IC). [In formula (IC), ^RC1 to ^RC4 each independently represent a hydrogen atom or a alkyl group having 1 to 20 carbon atoms which may have a substituent. ^RC5 to ^RC12 each independently represent a hydrogen atom or a alkyl group having 1 to 8 carbon atoms. ^TC1 represents a trivalent aromatic alkyl group having 6 to 14 carbon atoms which may have a substituent. CX ^Ck represents a metal cation having a ^valence of Ck. Ck represents an integer greater than 1.]

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ^C1 to R ^C4 include an aliphatic alkyl group having 1 to 20 carbon atoms and an aromatic alkyl group having 6 to 20 carbon atoms.

The aliphatic hydrocarbon group having 1 to 20 carbon atoms may be saturated or unsaturated, and may be linear, branched, or cyclic.

Examples of the linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms include linear aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, vinyl, 1-propenyl, 2-propenyl (allyl); and branched aliphatic hydrocarbon groups such as isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl.

The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic aliphatic hydrocarbon group include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include phenyl, thiophene, trimethylphenyl, dipropylphenyl, di(2,2-dimethylpropyl)phenyl, and naphthyl.

Substituents that may be possessed by the alkyl group having 1 to 20 carbon atoms represented by R ^C1 to R ^C4 include: halogen atoms such as fluorine atom, chlorine atom and iodine atom; hydroxyl group; carboxyl group; sulfonamide group; nitro group; alkoxy groups having 1 to 10 carbon atoms such as methoxy group and ethoxy group; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl group and ethoxycarbonyl group, etc.

Specific examples of the carbonyl group having 1 to 8 carbon atoms represented by R ^C5 to R ^C12 , and the substituent that the carbonyl group may have, are the same as those for R ^C1 to R ^C4 , except that the group having 9 to 20 carbon atoms is not included.

As the trivalent aromatic hydrocarbon group having 6 to 14 carbon atoms represented by T ^C1 , there can be exemplified a group having two hydrogen atoms contained in a monovalent aromatic hydrocarbon group among R ^C1 to R ^C4 (but excluding an aromatic hydrocarbon group having 15 to 20 carbon atoms) as bonding terminals.

Specific examples of the substituent which the trivalent aromatic hydrocarbon group having 6 to 14 carbon atoms represented by T ^C1 may have are the same as the substituent which the hydrocarbon group having 1 to 20 carbon atoms represented by R ^C1 to R ^C4 may have.

In the Ck-valent metal cations represented by CX ^{Ck ㊉} , examples of metals with Ck of 1 (i.e., monovalent metals) include alkaline metals such as lithium, sodium, potassium, and cesium; examples of metals with Ck of 2 (i.e., divalent metals) include alkaline earth metals such as magnesium, calcium, strontium, and barium, and transition metals such as zinc, copper, nickel, and manganese; examples of metals with Ck of 3 (i.e., trivalent metals) include typical metals such as aluminum, and transition metals such as cobalt and iron.

As compound (IC), ^RC1 to ^RC12 , T ^C1 and CX ^Ck are ^preferably as follows.

R ^C1 to R ^C4 are preferably each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 10 carbon atoms; more preferably a saturated linear aliphatic hydrocarbon group having 1 to 8 carbon atoms; further preferably a saturated linear aliphatic hydrocarbon group having 1 to 5 carbon atoms; further more preferably a methyl group or an ethyl group.

It is preferred ^{that RC1} to ^RC4 are the same group as ^RC3 , and ^RC2 and ^RC4 are the same group, and it is more preferred that ^RC1 to ^RC4 are all the same group.

R ^C5 to R ^C12 are preferably each independently a hydrogen atom or a saturated linear aliphatic hydrocarbon group having 1 to 5 carbon atoms, more preferably a hydrogen atom.

T ^C1 is preferably a trivalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and more preferably a trivalent aromatic hydrocarbon group having 6 to 10 carbon atoms which does not have a substituent, or a trivalent aromatic hydrocarbon group having 6 to 10 carbon atoms which has a hydroxyl group as a substituent.

Examples of the group having two -SO ₃ ^- bonded to T ^C1 include groups represented by the following formulae (cc-1) to (cc-22). (The * in the formula refers to the key end.)

The Ck-valent metal cation represented by CX ^{Ck ㊉} is preferably a cation of a metal having a Ck of 1 to 3 (i.e., a 1-valent to 3-valent metal), and more preferably a cation of barium, zinc, or manganese belonging to a metal having a Ck of 2 (i.e., a 2-valent metal).

Examples of the compound (IC) include compounds represented by formula (C-1) to formula (C-18) shown in Table 3.

[Table 3]

In Table 3, Me represents a methyl group, Et represents an ethyl group, and cc-3, cc-8, and cc-20 respectively mean the groups represented by the above formulae (cc-3), (cc-8), and (cc-20).

>>Compound（ID）>>

A compound represented by formula (ID). [In formula (ID), ^RD1 to ^RD10 each independently represent a hydrogen atom, a hydroxyl ^group , _-CO2- ^, _-SO3- , ^-O- , a group represented by formula (d), or a alkyl group having 1 to 20 carbon atoms which may have a substituent, and at least two of ^RD1 to ^RD10 represent _-CO2- ^, _-SO3- , ^{-O- ,} or a group represented by formula (d). (In formula (d), ^RD11 represents a hydrogen atom or a alkyl group having 1 to 20 carbon atoms which may have a substituent. ^LD1 represents a divalent aromatic alkyl group which may have a substituent. Dd ^㊀ represents -CO ₂ ^- or -SO ₃ ^- . However, * in the formula means a bond terminal.) ^TD1 represents a divalent aromatic alkyl group having 6 to 10 carbon atoms which may have a substituent. However, the aromatic alkyl group does not have -SO ₃ ^- as a substituent. ^RD21 represents a hydrogen atom or a alkyl group having 1 to 20 carbon atoms which may have a substituent. DX ^㊉ represents a monovalent metal cation. ]

Examples of the carbonyl group having 1 to 20 carbon atoms represented by R ^D1 to R ^D10 , R ^D11 , and R ^D21 include an aliphatic carbonyl group having 1 to 20 carbon atoms and an aromatic carbonyl group having 6 to 20 carbon atoms.

The aliphatic hydrocarbon group having 1 to 20 carbon atoms may be saturated or unsaturated, and may be linear, branched, or cyclic.

Examples of the linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms include linear aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, vinyl, 1-propenyl, 2-propenyl (allyl); and branched aliphatic hydrocarbon groups such as isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl.

The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic aliphatic hydrocarbon group include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include phenyl, thiophene, trimethylphenyl, dipropylphenyl, di(2,2-dimethylpropyl)phenyl, and naphthyl.

Substituents that may be possessed by the alkyl group having 1 to 20 carbon atoms represented by R ^D1 to R ^D10 , R ^D11 , and R ^D21 include: halogen atoms such as fluorine atom, chlorine atom, iodine atom; hydroxyl group; carboxyl group; sulfonamide group; nitro group; alkoxy group having 1 to 10 carbon atoms such as methoxy group and ethoxy group; alkoxycarbonyl group having 1 to 10 carbon atoms such as methoxycarbonyl group and ethoxycarbonyl group, etc.

The divalent aromatic hydrocarbon group represented by L ^D1 is preferably a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and includes groups in which one of the hydrogen atoms contained in the monovalent aromatic hydrocarbon groups of R ^D1 to R ^D10 , R ^D11 , and R ^D21 is used as a bond terminal.

The substituents which the divalent aromatic hydrocarbon group represented by ^LD1 may have are the same as the substituents which the hydrocarbon groups having 1 to 20 carbon atoms represented by ^RD1 to ^RD10 , ^RD11 and ^RD21 may have.

When compound (ID) has a plurality of groups represented by formula (d), and a plurality of R ^D11 , L ^D1 , and Dd ^㊀ exist in compound (ID), they may be the same or different.

As the divalent aromatic hydrocarbon group having 6 to 10 carbon atoms represented by ^TD1 , there can be exemplified a group having one of the hydrogen atoms contained in the monovalent aromatic hydrocarbon groups of ^RD1 to ^RD10 , ^RD11 , and ^RD21 (excluding the aromatic hydrocarbon group having 11 to 20 carbon atoms) as a bond terminal.

The substituents which the divalent aromatic hydrocarbon group having 6 to 10 carbon atoms represented by ^TD1 may have are the same as the substituents which the hydrocarbon groups having 1 to 20 carbon atoms represented by ^RD1 to ^RD10 , ^RD11 and ^RD21 may have.

Examples of metals that are monovalent metal cations represented by DX ^㊉ include alkaline metals such as lithium, sodium, potassium, and cesium.

As compound (ID), ^RD1 to ^RD10 , ^TD1 , ^RD21 and DX ^are preferably as follows.

Among ^RD1 to ^RD10 , the number of -CO ₂ ^- , -SO ₃ ^- , -O ^- or the group represented by formula (d) is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2. When there are 2 or more -CO ₂ ^- , -SO ₃ ^- , -O ^- or the group represented by formula (d) among ^RD1 to ^RD10 , it is preferred that at least one of ^RD1 to ^RD6 is -CO ₂ ^- , -SO ₃ ^- , -O ^- or the group represented by formula (b), and at least one of ^RD7 to ^RD10 is -CO ₂ ^- , -SO ₃ ^- , -O ^- or the group represented by formula (b).

When compound (ID) has a substituent represented by formula (d), it is preferred that at least two of ^RD1 to ^RD10 are groups represented by formula (d); more preferably, two to four of ^RD1 to ^RD10 are groups represented by formula (d) and do not have -CO ₂ ^- , -SO ₃ ^- , or -O ^- ; further preferably, two of ^RD1 to ^RD10 are groups represented by formula (d) and do not have -CO ₂ ^- , -SO ₃ ^- , or -O ^- . In addition, when compound (ID) has a plurality of groups represented by formula (d), it is preferred that the plurality of groups represented by formula (d) are the same.

The group represented by formula (d) is preferably a group in which L ^D1 is a phenylene methylene group, a methylphenylene methylene group or a dimethylphenylene methylene group which may have a substituent. More preferably, L ^D1 is a phenylene methylene group, a methylphenylene methylene group or a dimethylphenylene methylene group which does not have a substituent, R ^D11 is a hydrogen atom or a saturated hydrocarbon group having 1 to 2 carbon atoms which does not have a substituent, and ^Dd is -SO ₃ ^- .

As the group represented by the formula (d), for example, there can be mentioned groups represented by the following formulae (d-1) to (d-8). (The * in the formula refers to the bond end.)

The group other than -CO ₂ ^- , -SO ₃ ^- , -O ^- and the group represented by formula (d) represented by ^RD1 to ^RD10 is preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or a linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, further preferably a hydrogen atom or a linear aliphatic hydrocarbon group having 1 to 5 carbon atoms, and further preferably a hydrogen atom or a methyl group.

In ^RD1 to ^RD10 , the number of hydrogen atoms is preferably 4 to 8, more preferably 6 to 8.

T ^D1 is preferably a phenylene group which may have a substituent, and more preferably a phenylene group which does not have a substituent.

R ^D21 is preferably a phenylene group which may have a substituent, and more preferably a phenylene group having an alkoxy group having 1 to 5 carbon atoms as a substituent.

As ^RD21 , for example, there can be listed the groups represented by the following formulae (dd-1) to (dd-8). (The * in the formula refers to the bond end.)

The monovalent metal cation represented by DX ^㊉ is preferably an alkali metal cation, more preferably a cesium cation.

As compound (ID), groups represented by formula (D-1) to formula (D-8) shown in Table 4 can be listed.

[Table 4]

In Table 4, Me represents a methyl group, phe represents a phenylene group, and d-6, d-7, dd-1, and dd-4 respectively mean the groups represented by the above formulae (d-6), (d-7), (dd-1), and (dd-4).

Compound (IA), compound (IB), compound (IC), and compound (ID) can be produced according to known methods. For example, they can be produced by reacting a known dye with an acetate, carbonate, phosphate, sulfate, silicate, cyanide, or halide (preferably chloride) of an r-valent metal ion Mr ⁺ . In addition, the production method of the linking portion of compound (IB) can be appropriately referred to International Application Publication No. 2018/003708.

>Coloring resin composition>

The coloring resin composition of the present invention comprises a coloring agent (hereinafter, sometimes referred to as "coloring agent (A)") and a resin (hereinafter, referred to as "resin (B)"), wherein the coloring agent (A) comprises at least one selected from the following group: compound (IA), compound (IB), compound (IC), and compound (ID).

The coloring resin composition of the present invention preferably further comprises a polymerizable compound (hereinafter, sometimes referred to as "polymerizable compound (C)") and a polymerization initiator (hereinafter, sometimes referred to as "polymerization initiator (D)").

The coloring resin composition of the present invention may further include a polymerization initiation aid (hereinafter, sometimes referred to as "polymerization initiation aid (D1)"), a solvent (hereinafter, sometimes referred to as "solvent (E)"), and a leveling agent (hereinafter, sometimes referred to as "leveling agent (F)").

In the present specification, unless otherwise specified, compounds exemplified as components may be used alone or in combination of plural types.

>Coloring agent (A)>

The coloring resin composition of the present invention comprises at least one selected from the following group as a coloring agent (A): compound (IA), compound (IB), compound (IC), and compound (ID). The content of compound (IA), compound (IB), compound (IC), and/or compound (ID) is preferably 0.1 to 150 parts by mass, more preferably 0.5 to 100 parts by mass, and further preferably 1 to 80 parts by mass relative to 100 parts by mass of resin (B).

The content of compound (IA), compound (IB), compound (IC), and/or compound (ID) in the total amount of the coloring agent (A) is preferably 50 mass % or more, more preferably 80 mass % or more, and even more preferably 90 mass % or more.

In addition to compound (IA), compound (IB), compound (IC), and/or compound (ID), the colored resin composition of the present invention may also contain dyes (A1) and pigments (A2) as colorants (A).

The dye (A1) is not particularly limited, and known dyes can be used, for example, solvent dyes, acid dyes, direct dyes, mordant dyes, etc. Examples of the dye include compounds classified as substances having hues other than pigments in the Colour Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Color Dyeing Company). In addition, based on the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes (but excluding compound (IA), compound (IB), compound (IC), and compound (ID)), xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azo methine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes can be listed. Among them, organic solvent-soluble dyes are preferred.

The pigment (A2) is not particularly limited and known pigments can be used. For example, pigments classified as pigments in the Colour Index (published by the British Institute of Dyers and Colourists) can be cited.

For example, as pigments, we can cite: 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, 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, 15:6, 60 and other blue pigments; C.I. pigment purple 1, 19, 23, 29, 32, 36, 38 and other purple pigments; C.I. pigment green 7, 36, 58 and other green pigments; C.I. pigment brown 23, 25 and other brown pigments; C.I. pigment black 1, 7 and other black pigments, etc.

The amount of the coloring agent (A) is preferably 0.1 to 70 mass %, more preferably 0.5 to 60 mass %, and even more preferably 1 to 50 mass %, relative to the total amount of the solid components of the coloring resin composition.

Here, the "total amount of solid components" in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the coloring resin composition or the coloring curable resin composition. The total amount of solid components and the content of each component relative thereto can be measured by a known analytical method such as liquid chromatography or gas chromatography.

>Resin (B)>

The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably a resin having a structural unit derived from at least one monomer (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)"). Preferably, the resin (B) further has at least one structural unit selected from the group consisting of the following structural units: a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)"), a structural unit derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)"), and a structural unit having an ethylenically unsaturated bond on a side chain.

Specific examples of (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and mono[2-(meth)acryloxyethyl]succinate. Preferred examples include acrylic acid, methacrylic acid, and maleic anhydride.

(b) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxadiazine ring and a tetrahydrofuran ring) and a (meth)acryloyloxy group.

Furthermore, in this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. "(meth)acryl" and "(meth)acrylate" also have the same meaning.

Examples of (b) include glycidyl (meth)acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxycarbonyl, and tetrahydrofurfuryl (meth)acrylate. Glycidyl (meth)acrylate, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate, and 3-ethyl-3-(meth)acryloyloxymethyloxycarbonyl are preferred.

As (c), for example, there can be mentioned: methyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-9-yl (meth)acrylate, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene, etc.; preferably styrene, vinyltoluene, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-9-yl (meth)acrylate, etc.

The resin having a structural unit having an ethylenically unsaturated bond in the side chain can be prepared by adding (b) to a copolymer of (a) and (c), or by adding (a) to a copolymer of (b) and (c). The resin may also be a resin obtained by adding (a) to a copolymer of (b) and (c) and further reacting the resulting mixture with a carboxylic anhydride.

The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and more preferably 5,000 to 30,000.

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

The acid value of the resin (B) is preferably 20 mg-KOH/g (milligram-KOH/gram) to 170 mg-KOH/g, more preferably 30 mg-KOH/g to 150 mg-KOH/g, and further preferably 40 mg-KOH/g to 135 mg-KOH/g, calculated on a solid basis. Here, the acid value is a value measured as the amount (milligram) of potassium hydroxide required to neutralize 1 gram of the resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 5 to 65% by mass, more preferably 15 to 60% by mass, and further preferably 20 to 55% by mass, relative to the total solid content of the coloring resin composition.

>Polymerizable compound (C)>

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

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trihydroxymethylpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate.

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

When the polymerizable compound (C) is contained, the content of the polymerizable compound (C) is preferably 5 to 65% by mass, more preferably 15 to 60% by mass, and further preferably 20 to 55% by mass relative to the total amount of the solid component.

>Polymerization initiator (D)>

The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat to initiate polymerization, and a known polymerization initiator can be used. Examples of the polymerization initiator that generates active radicals include N-benzoyloxy-1-(4-phenylthiohydrophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiohydrophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiohydrophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiohydrophenyl)-3-cyclohexylpropane-1-one-2-imine, -Keto-2-imine, 2-methyl-2-oxo-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-oxo-1-phenyl)-2-benzylbutane-1-one, 1-hydroxycyclohexylphenyl ketone, 2,4-bis(trichloromethyl)-6-sunflower-1,3,5-triazine, 2,4,6-trimethylbenzyldiphenylphosphine oxide, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, etc.

When the polymerization initiator (D) is included, the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the content of the polymerization initiator (D) is within the above range, there is a tendency for high sensitivity to be achieved and the exposure time to be shortened, so that the productivity of the color filter can be improved.

>Polymerization initiation aid (D1)>

The polymerization initiator (D1) is a compound for promoting the polymerization of the polymerizable compound that starts polymerization by the polymerization initiator, or a sensitizer. When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

Examples of the polymerization initiator (D1) include 4,4'-bis(dimethylamino)benzophenone (commonly known as michler's ketone), 4,4'-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethyl thioxanthone, and N-phenylglycine.

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

>Solvent (E)>

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

As the solvent (E), there can be listed: Ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetylacetate, cyclohexanol acetate and γ-butyrolactone (solvents containing -COO- but not -O- in the molecule); Ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether (solvents containing -O- but not -COO- in the molecule); Methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl ethyl Ether ester solvents such as esters, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and diethylene glycol monoethyl ether acetate (solvents containing -COO- and -O- in the molecule); Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), heptanone, 4-methyl-2-pentanone, and cyclohexanone (solvents containing -CO- but not -COO- in the molecule); Alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents containing OH but not -O-, -CO-, and -COO- in the molecule); Amine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, etc.

As the solvent (E), more preferred are propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, N-methylpyrrolidone, 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), ethyl lactate and ethyl 3-ethoxypropionate.

When the solvent (E) is contained, the content of the solvent (E) is preferably 60 to 97% by mass, more preferably 65 to 95% by mass, relative to the total amount of the coloring resin composition of the present invention. In other words, the total amount of the solid components of the coloring resin composition is preferably 3 to 40% by mass, more preferably 5 to 35% by mass. If the content of the solvent (E) is within the above range, the flatness during coating becomes good, and the color concentration is not insufficient when forming a color filter, so there is a tendency that the display characteristics become good.

>Leveling agent (F)>

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

Examples of polysilicone-based surfactants include those having siloxane bonds in their molecules. Specifically, the following can be cited: TORAY SILICONE DC3PA, TORAY SILICONE SH7PA, TORAY SILICONE DC11PA, TORAY SILICONE SH21PA, TORAY SILICONE SH28PA, TORAY SILICONE SH29PA, TORAY SILICONE SH30PA, TORAY SILICONE SH8400 (trade names, 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 (manufactured by Maitu Advanced Materials Japan Contract Co., Ltd.), etc.

As the aforementioned fluorine-based surfactant, there can be cited surfactants having a fluorine-carbon chain in the molecule. Specifically, they include: FLOURAD (registered trademark) FC430, FLOURAD (registered trademark) FC431 (manufactured by Sumitomo 3M Co., Ltd.); MEGAFAC (registered trademark) F142D, MEGAFAC (registered trademark) F171, MEGAFAC (registered trademark) F172, MEGAFAC (registered trademark) F173, MEGAFAC (registered trademark) F177, MEGAFAC (registered trademark) F183, MEGAFAC (registered trademark) F554, MEGAFAC (registered trademark) R30, MEGAFAC (registered trademark) RS- 718-K (manufactured by DIC Corporation); EFTOP (registered trademark) EF301, EFTOP (registered trademark) EF303, EFTOP (registered trademark) EF351, EFTOP (registered trademark) EF352 (manufactured by Mitsubishi Materials Corporation); SURFLON (registered trademark) S381, SURFLON (registered trademark) S382, SURFLON (registered trademark) SC101, SURFLON (registered trademark) SC105 (manufactured by Asahi Glass Co., Ltd.); and E5844 (manufactured by Daikin Fine Chemicals Laboratories, Ltd.), etc.

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

When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.001 to 0.2 mass %, more preferably 0.002 to 0.1 mass % relative to the total amount of the coloring resin composition. In addition, this content does not include the content of the pigment dispersant. If the content of the leveling agent (F) is within the above range, the flatness of the color filter may be improved.

>Other Ingredients>

The coloring resin composition of the present invention may contain fillers, polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and other additives known in the relevant technical fields as needed.

>Method for producing coloring resin composition>

The coloring resin composition of the present invention can be prepared by mixing a coloring agent (A) and a resin (B), and, if necessary, a polymerizable compound (C), a polymerization initiator (D), a polymerization initiation aid (D1), a solvent (E), a leveling agent (F) and other components.

>Method for manufacturing color filter>

As a method for producing a colored pattern from the colored resin composition of the present invention, photolithography, inkjet method, printing method, etc. can be cited. Among them, photolithography is preferred.

The coloring resin composition comprises a compound (IA), a compound (IB), a compound (IC) and/or a compound (ID) having excellent heat resistance, thereby being able to produce a color filter having excellent heat resistance. The color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL (electroluminescence) device, an electronic paper, etc.) and a solid-state imaging element.

In the following, the present invention will be described in more detail by way of examples, but the present invention is not limited to the examples. In the examples, "%" and "parts" indicating the content or dosage are all based on mass unless otherwise specified.

In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC; Model 1200 manufactured by Agilent, MASS; Model LC/MSD manufactured by Agilent).

[Example 1]

The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a condenser and a stirrer, 2.5 parts of CI Acid Blue 90 (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.2 parts of manganese chloride tetrahydrate (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.), and 15 parts of ion-exchanged water were added and stirred at 50°C for 2 hours. The obtained reaction suspension was left to cool and then filtered. The solid obtained by filtration was washed with 2.5 parts of ion-exchanged water and dried under reduced pressure at 60°C to obtain 2.3 parts of the compound represented by formula (A-16). Identification mass analysis of the compound represented by formula (A-16): ionization mode ESI+ m/z: 832.8 Exact mass [(M-Mn)/2+2H] ⁺ : 832.3

[Example 2]

The following reaction was carried out under a nitrogen atmosphere. 2.5 parts of CI Acid Blue 83 (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.0 part of cesium chloride (manufactured by Fuji Films Wako Pure Chemical Industries, Ltd.), and 20 parts of ion-exchanged water were added to a flask equipped with a condenser and a stirrer, and stirred at 50°C for 2 hours. The obtained reaction suspension was left to cool, and then filtered. The solid obtained by filtration was washed with 10 parts of ion-exchanged water, and dried under reduced pressure at 60°C to obtain 2.1 parts of the compound represented by formula (D-2). Identification mass analysis of the compound represented by formula (D-2): ionization mode ESI+ m/z: 804.5 Exact mass [M-Cs+2H] ⁺ : 804.3

[Example 3]

The following reaction was carried out under a nitrogen atmosphere. 2.5 parts of CI Acid Blue 90 (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.8 parts of zinc chloride (manufactured by Fuji Films Wako Pure Chemical Industries, Ltd.), and 20 parts of ion exchange water were added to a flask equipped with a condenser and a stirrer, and stirred at 50°C for 2 hours. The obtained reaction suspension was left to cool, then filtered, and the solid obtained by filtration was washed with 2.5 parts of ion exchange water and dried under reduced pressure at 60°C to obtain 1.9 parts of the compound represented by formula (A-18). Identification mass analysis of the compound represented by formula (A-18): ionization mode ESI+ m/z: 832.8 Exact mass [(M-Zn)/2+2H] ⁺ : 832.3

[Example 4]

The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a condenser and a stirrer, 2.5 parts of CI Acid Green 9 (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.9 parts of barium chloride dihydrate (manufactured by Fuji Films Wako Pure Chemical Industries, Ltd.), and 30 parts of ion-exchanged water were added and stirred at 50°C for 2 hours. The obtained reaction suspension was left to cool and then filtered. The solid obtained by filtration was washed with 2.5 parts of ion-exchanged water and dried under reduced pressure at 60°C to obtain 1.3 parts of the compound represented by formula (A-2). Identification mass analysis of the compound represented by formula (A-2), ionization mode ESI+ m/z: 703.5 Exact mass [(M-Ba)/2+2H] ⁺ : 703.2

[Example 5]

The following reaction was carried out under a nitrogen atmosphere. 2.5 parts of CI Mordant Blue 1 (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.4 parts of barium chloride dihydrate (manufactured by Fuji Film Co., Ltd. Wako Pure Chemical Industries, Ltd.), and 30 parts of ion-exchanged water were added to a flask equipped with a condenser and a stirrer, and stirred at 50°C for 2 hours. The obtained reaction suspension was left to cool, and then filtered. The solid obtained by filtration was washed with 2.5 parts of ion-exchanged water, and dried under reduced pressure at 60°C to obtain 2.9 parts of the compound represented by formula (A-23). Identification mass analysis of the compound represented by formula (A-23), ionization mode ESI+ m/z: 459.5 Exact mass [M-Ba+3H] ⁺ : 459.0

[Example 6]

The following reaction was carried out under a nitrogen atmosphere. 2.5 parts of CI Acid Blue 1 (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.2 parts of barium chloride dihydrate (manufactured by Fuji Films Wako Pure Chemical Industries, Ltd.), and 30 parts of ion-exchanged water were added to a flask equipped with a condenser and a stirrer, and stirred at 50°C for 2 hours. The obtained reaction suspension was left to cool, then filtered, and the solid obtained by filtration was washed with 2.5 parts of ion-exchanged water and dried under reduced pressure at 60°C to obtain 1.7 parts of the compound represented by formula (C-11). Identification mass analysis of the compound represented by formula (C-11): ionization mode ESI+ m/z: 545.5 Exact mass [(M-Ba)/2+2H] ⁺ : 545.2

[Example 7]

The following reaction was carried out under a nitrogen atmosphere. 2.5 parts of Acid Green 50 (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.1 parts of barium chloride dihydrate (manufactured by Fuji Films Wako Pure Chemical Industries, Ltd.), and 30 parts of ion-exchanged water were added to a flask equipped with a condenser and a stirrer, and stirred at 50°C for 2 hours. The obtained reaction suspension was left to cool, and then filtered. The solid obtained by filtration was washed with 2.5 parts of ion-exchanged water, and dried under reduced pressure at 60°C to obtain 2.2 parts of the compound represented by formula (C-8). Identification mass analysis of the compound represented by formula (C-8): ionization mode ESI+ m/z: 555.5 Exact mass [(M-Ba)/2+2H] ⁺ : 555.1

[Example 8]

The following reaction was carried out under a nitrogen atmosphere. 2.5 parts of Acid Green A (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.2 parts of barium chloride dihydrate (manufactured by Fuji Films Wako Pure Chemical Industries, Ltd.), and 30 parts of ion exchange water were added to a flask equipped with a condenser and a stirrer, and stirred at 50°C for 2 hours. The obtained reaction suspension was left to cool, then filtered, and the solid obtained by filtration was washed with 2.5 parts of ion exchange water and dried under reduced pressure at 60°C to obtain 0.9 parts of the compound represented by formula (C-14). Identification mass analysis of the compound represented by formula (C-14): ionization mode ESI+ m/z: 573.5 Exact mass [(M-Ba)/2+2H] ⁺ : 573.2

>Heat resistance evaluation>

Using a thermogravimetric differential thermal analyzer (TG/DTA6200, manufactured by SEIKO INSTRUMENTS Co., Ltd.), approximately 3000 μg of each compound was heated from 45°C to 550°C at a rate of 5°C/min. For each compound, the temperature T (°C) observed when the weight decreased by 5% from the initial weight was measured after 170°C. The results are shown in Table 5.

Furthermore, as a comparative example, C.I. Pigment Blue 24 was used.

[Table 5]

[Resin Synthesis Example 1]

A suitable amount of nitrogen was passed through a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, and 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added, and heated to 85°C while stirring. Then, the following mixed solution was added dropwise over 5 hours: 38 parts of acrylic acid, 25 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]dec-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]dec-9-yl acrylate (containing ratio of 1:1), 137 parts of cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate. On the other hand, a mixed solution prepared by dissolving 5 parts of 2,2-azobisisobutyronitrile in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (BX)) solution having a solid content of 25.6%. The weight average molecular weight Mw of the generated copolymer was 8000, the degree of dispersion was 2.1, and the acid value converted to solid content was 111 mg-KOH/g. Resin (BX) has the following structural units.

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin are measured using the GPC (Gel Permeation Chromatography) method under the following conditions. Device: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40°C Solvent: THF (tetrahydrofuran) Flow rate: 1.0 mL/min Concentration of solid components in the tested liquid: 0.001 mass% to 0.01 mass% Injection volume: 50 μL Detector: RI Standard substances for calibration: TSK STANDARD POLYSTYRENE (standard polystyrene) F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

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

>Production of Coloring Resin Composition>

The following components are mixed to obtain a coloring resin composition: Coloring agent (A): Compound (A-16)          0.5 parts (solid content conversion) Resin (B): Resin (B-X)               2.1 parts (solid content conversion) Polymerizable compound (C): Dipentatriol hexaacrylate (KAYARAD (registered trademark) DPHA, manufactured by Nippon Kayaku Co., Ltd.)     2.1 parts (solid content conversion) Polymerization initiator (D): N-benzoyloxy-1-(4-phenylthiothiophenyl)octan-1-one-2-imine (IRGACURE (registered trademark) OXE-01, manufactured by BASF, O-acyl oxime compound) 0.3 parts Solvent (E): Propylene glycol monomethyl ether acetate        16.1 parts Ethyl lactate                      1.2 parts N-methylpyrrolidone            24.5 parts Leveling agent (F): Polyether modified silicone oil (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.)                   0.005 parts (solid content conversion) In addition, compound (A-16) was dissolved in 24.5 parts of N-methylpyrrolidone before mixing.

>Production of color filters (colored coatings)>

The colored curable resin composition was applied to a 5 cm square glass substrate (Eagle 2000, manufactured by Corning) by a spin coating method in such a way that the film thickness after post-baking was 2 μm, and then pre-baked at 100°C for 3 minutes. After cooling, it was post-baked in an oven at 230°C for 20 minutes to obtain a color filter. The color filter exhibited high heat resistance.

without

without

Claims (5)

A triarylmethane compound is represented by formula (IA), formula (IB), or formula (ID):

In formula (IA), ^RA1 to ^RA2 are each independently a group represented by formula (a-6), ^RA3 to ^RA10 are each independently a hydrogen atom, ^TA1 is a group represented by formula (aa-1) or formula (aa-2), or ^RA1 to ^RA2 are each independently a group represented by formula (a-6), ^RA3 and ^RA10 are each independently a methyl group, ^RA4 to ^RA9 are each independently a hydrogen atom, ^TA1 is a group represented by formula (aa-1), formula (aa-2) or formula (aa-6), or ^RA1 is ^-O- , ^RA2 is a ^hydroxyl group, ^RA3 , ^RA6 , ^RA7 and ^RA10 are each independently a hydrogen atom, ^RA4 and ^RA8 are each independently a methyl group, ^RA5 and ^RA9 are each independently _-CO2- ^TA1 is a group represented by formula (aa-1), formula (aa-2) or formula (aa-6),

In the formula, * means a bond terminal; An represents the sum of the numbers of -CO ₂ ^- , -SO ₃ ^- , and -O ^- in the compound represented by formula (IA); Am represents an integer greater than 1; AX ^Ak♁ represents a metal cation with an Ak valence; Ak represents an integer greater than 2;

In formula (IB), ^RB1 to ^RB10 each independently represent a hydrogen atom, a hydroxyl ^group , _-CO2- ^, _-SO3- , ^-O- , a group represented by formula (b), or a alkyl group having 1 to 20 carbon atoms which may have a substituent, at least two of ^RB1 to ^RB10 represent _-CO2- , ^{-SO3- ,} -O- ^, or a group represented by formula (b), ^{and two of RB1 to RB10 substantially} _represent a group represented by formula (b);

In formula (b), ^RB11 represents a hydrogen atom or a carbon number of 1 to 20 which may have a substituent, ^LB1 represents a divalent aromatic hydrocarbon group which may have a substituent, ^Bbθ represents _-CO2- or _-SO3- , but the * in the formula means a bond terminal; Bn represents the ^sum of the numbers of ^-CO2- , ^-SO3- , and ^-O- possessed by the compound represented by formula ( _IB ⁾ ; ^TB1 represents a divalent aromatic hydrocarbon group which may have a carbon number of 6 to 14 which may _have a substituent; but the aromatic hydrocarbon group does not ^have _-SO3- as a substituent; ^LB0 represents a Bm-valent linking group; Bm represents an integer greater than 2; ^BXBk♁ represents a Bk-valent metal cation; Bk represents an integer greater than 1;

In formula (ID), R ^D1 to R ^D2 are each independently a group represented by formula (d-6), R ^D3 to R ^D10 are each independently a hydrogen atom, T ^D1 is a phenylene group, and R ^D21 is a group represented by formula (dd-1), or R ^D1 to R ^D2 are each independently a group represented by formula (d-6) or formula (d-7), R ^D3 and R ^D10 are each independently a methyl group, R ^D4 to R ^D9 are each independently a hydrogen atom, T ^D1 is a phenylene group, and R ^D21 is a group represented by formula (dd-1) or formula (dd-4), or R ^D1 to R ^D2 are each independently a group represented by formula (d-7), R ^D3 to R ^D10 are each independently a hydrogen atom, T ^D1 is a phenylene group, and R ^D21 is a group represented by formula (dd-1) or formula (dd-4),

In the formula, * refers to the bond end; DX ^♁ represents the monovalent metal cation. A coloring resin composition comprising a coloring agent and a resin, wherein the coloring agent comprises at least one selected from the group consisting of a compound represented by formula (IA), a compound represented by formula (IB), and a compound represented by formula (ID) as described in claim 1. The coloring resin composition as described in claim 2 further comprises a polymerizable compound and a polymerization initiator. A color filter formed from the colored resin composition as described in claim 3. A display device comprising a color filter as described in claim 4.