TWI763706B - Compound useful as colorant - Google Patents

Abstract

The present invention is a compound represented by the formula (I).

[In the formula (I), R^N1 and R^N2 each independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. A^r1 represents an aromatic hydrocarbon group having 6 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R¹ to R⁸ each independently represent a hydrogen atom, -CO-R¹⁰², -COO-R¹⁰¹, -OCO-R¹⁰², -COCO-R¹⁰², -O-R¹⁰², -SO₂-R¹⁰¹, -SO₂N(R¹⁰²)₂, -CON (R¹⁰²)₂, -N(R¹⁰²)₂, -NHCO-R¹⁰², -NHCO-N(R¹⁰²)₂, -NHCOOR¹⁰², -OCON (R¹⁰²)₂, halogen atom, cyano group, nitro group, -SO₃M, - CO₂M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R¹⁰¹ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R¹⁰² represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. When there are a plurality of R¹⁰¹, R¹⁰² and M, they may be the same or different. A^g- represents a g-valent anion. g represents an integer of 1 to 14.]

Description

Compounds useful as colorants

The present invention relates to compounds and coloring compositions useful as colorants.

Dyestuffs are used, for example, in the fields of fiber materials, liquid crystal display devices, ink jets, and the like to display colors using reflected light or transmitted light. As such a dye, Coumarin 6 (Coumarin 6) represented by the following formula is known (Japanese Patent Laid-Open No. 2006-154740).

The present invention includes the following inventions.

式(I)中，R^N1及R^N2係相互獨立地表示可具有取代基之碳數1至40的烴基或可具有取代基的雜環基。Ar¹表示可具有取代基的碳數6至40之芳香族烴基或可具有取代基的雜環基。 [1] A compound represented by the formula (I),

In formula (I), R ^N1 and R ^N2 each independently represent an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. Ar ¹ represents an optionally substituted aromatic hydrocarbon group having 6 to 40 carbon atoms or an optionally substituted heterocyclic group.

R ¹ to R ⁸ each independently represent a hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N(R ¹⁰² ) ₂ , -CON(R ¹⁰² ) ₂ , -N(R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N(R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON(R ¹⁰² ) ₂ . A halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, or an optionally substituted heterocyclic group.

R ¹⁰¹ represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.

R ¹⁰² represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, or an optionally substituted heterocyclic group.

M represents a hydrogen atom or an alkali metal atom.

When a plurality of R ¹⁰¹ , R ¹⁰² and M are present, these may be the same or different.

A ^g- represents a g-valent anion.

g represents an integer from 1 to 14.

[2] The compound according to item [1], wherein A ^g- is an anion or fluorine containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements anion.

[3] The compound according to [1] or [2], wherein A ^g- contains an anion or fluorine containing at least one element selected from the group consisting of tungsten and phosphorus and oxygen as essential elements anion.

[4] The compound according to any one of [1] to [3], wherein A ^g- contains at least one element selected from the group consisting of tungsten and phosphorus and oxygen as essential elements anion.

[5] A coloring composition comprising the compound according to any one of [1] to [4] and a solvent.

[6] The coloring composition according to the item [5], further comprising a resin.

[7] The coloring composition according to the item [5] or [6], further comprising a yellow colorant, an orange colorant, or a red colorant.

[8] A coloring curable composition comprising the coloring composition according to any one of [5] to [7].

[9] The colorable curable composition according to the item [8], further comprising a polymerization initiator.

[10] A color filter comprising the coloring composition according to any one of [5] to [7], or the coloring curable composition according to [8] or [9] .

[11] A liquid crystal display device comprising the color filter described in [10].

The compound of the present invention is a compound represented by formula (I) (hereinafter, also referred to as compound (I)). The compounds of the present invention may contain their tautomers or their salts.

Compound (I) can be used as a colorant.

The coloring composition of the present invention contains the compound (I) and a solvent (hereinafter, also referred to as a solvent (E)).

The coloring composition of this invention may contain 1 type or 2 or more types of compound (I).

Furthermore, the compound (I) is preferably dispersed in the solvent (E).

The coloring composition of the present invention may contain resin (hereinafter, also referred to as resin (B)).

The coloring composition of the present invention may contain a coloring agent (hereinafter, also referred to as a coloring agent (A1) other than the compound (I), and in the following, the compound (I) and the coloring agent (A1) may be collectively referred to as "coloring agent". (A)”).

In the coloring agent (A1), one type or two or more types of colorants may be contained.

The colorant (A1) preferably further contains a yellow colorant, an orange colorant, or a red colorant.

Furthermore, the colored curable composition of the present invention contains at least one of the compound (I), the resin (B) and the solvent (E), and the polymerizable compound (C).

The colored curable composition of the present invention may further contain a polymerization initiator (D).

The colored curable composition of the present invention may further contain a polymerization initiator (D1).

The coloring composition of the present invention may further contain a leveling agent (F) and an antioxidant.

<Compound (I)>

Compound (I) is a compound represented by formula (I).

式(I)中，R^N1及R^N2係相互獨立地表示可具有取代基的碳數1至40之烴基或可具有取代基的雜環基。

In formula (I), R ^N1 and R ^N2 each independently represent an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.

Ar ¹ represents an optionally substituted aromatic hydrocarbon group having 6 to 40 carbon atoms or an optionally substituted heterocyclic group.

R ¹ to R ⁸ each independently represent a hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N(R ¹⁰² ) ₂ , -CON(R ¹⁰² ) ₂ , -N(R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N(R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON(R ¹⁰² ) ₂ . A halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, or an optionally substituted heterocyclic group.

R ¹⁰¹ represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.

R ¹⁰² represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, or an optionally substituted heterocyclic group.

M represents a hydrogen atom or an alkali metal atom.

When a plurality of R ¹⁰¹ , R ¹⁰² and M are present, these may be the same or different. A ^g- represents a g-valent anion. g represents an integer from 1 to 14.

The carbon number of the hydrocarbon group represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, A scale of 1 to 10 is preferred.

The hydrocarbon groups represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² with 1 to 40 carbon atoms may be aliphatic hydrocarbon groups and aromatic hydrocarbon groups, and the aliphatic hydrocarbon groups may be saturated or unsaturated, or may be Is a chain or alicyclic.

Saturated or unsaturated chain hydrocarbon groups represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² include methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl , octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl and eicosyl linear alkyl groups, etc.; isopropyl, isobutyl, Second-butyl, third-butyl, (2-ethyl)butyl, isopentyl, neopentyl, third-pentyl, (1-methyl)pentyl, (2-methyl)pentyl, Branched chains such as (1-ethyl)pentyl, (3-ethyl)pentyl, isohexyl, (5-methyl)hexyl, (2-ethyl)hexyl and (3-ethyl)heptyl Alkyl, etc.; vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1,3-butadiene alkenyl, (1-(2-propenyl))vinyl, (1,2-dimethyl)propenyl, and 2-pentenyl and the like. The carbon number of the saturated or unsaturated chain hydrocarbon group is preferably from 1 to 30, more preferably from 1 to 20, more preferably from 1 to 15, more preferably from 1 to 10, still more preferably from 1 to 8, A score of 1 to 5 is preferred. Among them, straight or branched alkyl groups with 1 to 10 carbon atoms are preferred, and methyl or ethyl groups are more preferred.

Saturated or unsaturated alicyclic hydrocarbon groups represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, and cyclopentane cyclohexyl, cyclohexyl, cyclohexyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3 -Dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6 -Dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 4,4 - Dimethylcyclohexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl , 4-pentylcyclohexyl, 4-octylcyclohexyl, 4-cyclohexylcyclohexyl and other cycloalkyl groups; cyclohexenyl (such as cyclohexa-2-ene, cyclohexa-3-ene), cycloheptene cycloalkenyl, such as cyclooctenyl, cyclooctenyl; norbornyl, adamantyl, bicyclo[2.2.2]octane, etc. The carbon number of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, more preferably 4 to 20, still more preferably 4 to 15, especially 5 to 15 good, with 5 to 10 being the best. Among them, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl are particularly preferred.

The aromatic hydrocarbon groups represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² include phenyl, o-tolyl, m-tolyl, p-tolyl, and 2,3-dimethylbenzene. base, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl base, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butyl phenyl, mesityl, 4-ethylphenyl, 4-butylphenyl, 4-pentylphenyl, 2,6-bis(2-propyl)phenyl, 4-cyclohexylphenyl , 2,4,6-trimethylphenyl, 4-octylphenyl, 4-vinylphenyl, 1-naphthyl, 2-naphthyl, 5,6,7,8-tetrahydro-1- Aromatic hydrocarbon groups such as naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, intenyl, phenanthryl, anthracenyl, and pyrenyl, and the like. The carbon number of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 15.

The hydrocarbon group represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may be a combination of the above-mentioned hydrocarbon groups (for example, at least one of an aromatic hydrocarbon group, a chain hydrocarbon group and an alicyclic hydrocarbon group). Examples of the group include: aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; phenylethenyl (phenyl ethenyl, phenyl vinyl), etc. Arylalkenyl; arylalkynyl such as phenylethynyl; phenyl with one or more phenyl bonds such as biphenyl and triphenyl; Dimethyl(phenyl)methyl)phenyl and the like.

The groups represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² , which are groups in which the above-mentioned hydrocarbon groups (eg, chain hydrocarbon groups and alicyclic hydrocarbon groups) are combined, may be, for example, cyclic groups. propylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, 2-methylcyclohexylmethyl, cyclohexylethyl An alkyl group in which one or more alicyclic hydrocarbon groups are bonded, such as an adamantyl methyl group.

The carbon number of the aforementioned hydrocarbon is preferably from 4 to 30, more preferably from 6 to 30, more preferably from 6 to 20, still more preferably from 4 to 20, still more preferably from 4 to 15, and still more preferably from 6 to 20. 15 is preferred.

The hydrocarbon groups represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may have a substituent. The substituent may be monovalent or divalent. The divalent substituent is preferably one where two bonds are bonded to the same carbon atom to form a double bond.

Examples of the monovalent substituent include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a second butoxy group, a third butoxy group, and a pentyloxy group. Oxy, hexyloxy, (2-ethyl)hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl ) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, o-tolyloxy, 2,3-dimethylbenzene oxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2,6-dimethylphenyloxy, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyloxy, 2,2-dicyanophenyloxy, 2,3-dicyanophenyloxy, 2,4-dicyanophenyloxy, 2,5-dicyanophenyloxy, 2,6-dicyanophenyloxy, 3,4-dicyanophenyloxy, 3,5-dicyanophenyloxy, 4- Methoxyphenyloxy, 2-methoxyphenyloxy, 3-methoxyphenyloxy, 4-ethoxyphenyloxy, 2-ethoxyphenyloxy, 3- Ethoxyphenyloxy, etc., and groups represented by the following formula, etc., have a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfonic acid group, etc.) bonded to one side. Oxygen group of acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylaminosulfonyl group (preferably octylaminosulfonyl group) with carbon number 1 to 10, etc. derivatized);

Methylsulfanyl, ethylsulfanyl, propylsulfanyl, butylsulfanyl, tert-butylsulfanyl, pentylsulfanyl, hexylsulfanyl, (2-ethyl)hexylsulfanyl, heptylsulfanyl , octylthio, nonylthio, decylthio, undecylthio, dodecylthio, eicosylthio, phenylthio and o-tolylthio etc. Sulfanyl group having a hydrocarbon group with a carbon number of 1 to 20 (preferably with a carbon number of 1 to 10); epoxy group, oxetanyl group, tetrahydrofuranyl group, tetrahydropyranyl group; carboxyl group; acetyl group, Propionyl, butyryl, 2,2-dimethylpropionyl, pentamyl, hexyl, (2-ethyl)hexyl, heptyl, octyl, nonyl, decyl, ten Monoyl, dodecyl, behenyl, benzyl, etc., and groups represented by the following formula, etc., are bonded to a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or derivatives thereof. Derivatized with a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylaminosulfonyl group having a carbon number of 1 to 10 (preferably an octylaminosulfonyl group), etc. The carbonyl group of the base) (when the carbonyl group is used as an alkanoyl group, the carbon number is preferably 2 to 12);

Methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, tert-butoxycarbonyl, pentoxycarbonyl, hexyloxycarbonyl, (2-ethyl)hexyloxycarbonyl, heptyloxy Carbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, eicosyloxycarbonyl, phenoxycarbonyl, o-tolyloxycarbonyl, etc. and the group represented by the following formula, etc., are bonded with a hydrocarbon group with a carbon number of 1 to 20 (preferably with a carbon number of 1 to 10) or its derivative group (such as a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (with a chlorine group), etc. Atom is preferred), the oxycarbonyl group of alkylaminosulfonyl group with carbon number of 1 to 10 (octylaminosulfonyl group is preferably a derivatized group);

Amino; N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-diethylamino, N-propylamino, N,N-dipropyl amino, N-isopropylamine, N,N-diisopropylamine, N-butylamine, N,N-dibutylamine, N-isobutylamine, N, N-diisobutylamine, N-second-butylamine, N,N-di-second-butylamine, N-tert-butylamine, N,N-di-tert-butylamine , N-pentylamino, N,N-dipentylamino, N-(1-ethylpropyl)amino, N,N-bis(1-ethylpropyl)amino, N-hexyl Amino, N,N-dihexylamino, N-(2-ethyl)hexylamino, N,N-bis(2-ethyl)hexylamino, N-heptylamino, N,N- Diheptylamino, N-octylamino, N,N-dioctylamino, N-nonylamino, N,N-dinonylamino, N-phenylamino, N,N -Diphenylamine, N,N-ethylmethylamine, N,N-propylmethylamine, N,N-isopropylmethylamine, N,N-butylmethylamine, N-decylamino, N,N-decylmethylamino, N-undecylamino, N,N-undecylmethylamino, N-dodecylamino, N ,N-dodecylmethylamine, N-eicosylamine, N,N-eicosylmethylamine, N,N-tert-butylmethylamine, N,N-benzene Alkylmethylamine group, etc., and groups represented by the following formulas, etc., have one or two hydrocarbon groups with 1 to 20 carbon atoms (preferably with 1 to 10 carbon atoms) or derivatives thereof (for example, a carboxyl group, a sulfonic acid group) , nitro, hydroxyl, halogen (preferably chlorine atom), alkyl sulfamoyl group (preferably octyl sulfamoyl group) and other derivatized amine groups with carbon number 1 to 10) substituted amino groups;

Sulfamoyl; N-methylsulfamoyl, N,N-dimethylsulfamoyl, N-ethylsulfamoyl, N,N-diethylsulfamoyl, N-propyl Sulfonyl, N,N-dipropylaminesulfonyl, N-isopropylaminesulfonyl, N,N-diisopropylaminesulfonyl, N-butylaminesulfonyl, N,N-Dibutylaminesulfonyl, N-isobutylaminesulfonyl, N,N-diisobutylaminesulfonyl, N-dibutylaminesulfonyl, N,N- Di-2-butyl sulfamoyl, N-tert-butyl sulfamoyl, N,N-di-tert-butyl sulfamoyl, N-pentyl sulfamoyl, N,N-dipentane sulfamoyl, N-(1-ethylpropyl) sulfamoyl, N,N-bis(1-ethylpropyl) sulfamoyl, N-hexyl sulfamoyl, N,N - Dihexyl sulfamoyl, N-(2-ethyl) hexyl sulfamoyl, N,N-bis(2-ethyl) hexyl sulfamoyl, N-heptyl sulfamoyl, N, N, N-diheptylaminosulfonyl, N-octylaminosulfonyl, N,N-dioctylaminosulfonyl, N,N-octylmethylaminosulfonyl, N-nonylaminosulfonyl Sulfonyl, N,N-dinonylsulfamoyl, N-phenylsulfamoyl, N,N-diphenylsulfamoyl, N,N-ethylmethylsulfamoyl, N ,N-propylmethylaminosulfonyl, N,N-isopropylmethylaminosulfonyl, N,N-butylmethylaminosulfonyl, N-decylaminosulfonyl, N,N- Decylmethylaminosulfonyl, N-undecylaminosulfonyl, N,N-undecylmethylaminosulfonyl, N-dodecylaminosulfonyl, N,N- Dodecylmethylaminosulfonyl, N-icosylaminosulfonyl, N,N-eicosylmethylaminosulfonyl, N,N-tert-butylmethylaminosulfonyl, N,N-Phenylmethylaminosulfonyl, etc., and groups represented by the following formulae, etc., have one or two hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivatives thereof ( For example, a group derivatized with a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylaminosulfonyl group having a carbon number of 1 to 10 (preferably an octylaminosulfonyl group), etc. ) substituted sulfamoyl;

Carboxylamido; Acetylamino, Propionylamino, Butylamino, 2,2-dimethylpropionylamino, Pentanylamino, Hexylamino, (2- Ethyl) hexylamino, heptylamino, octylamino, nonylamino, decanoylamino, undecanoylamino, dodecanoylamino, hexadecanoylamino An amino group, a benzylamino group, etc., and a group represented by the following formula, etc., are bonded to a hydrocarbon group with a carbon number of 1 to 20 (preferably a carbon number of 1 to 12) or a derivative group thereof (for example, a carboxyl group, a sulfonic acid group) Carbonyl substituted by acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkyl sulfamoyl group having 1 to 10 carbon atoms (preferably octyl sulfamoyl group), etc. Amino group (when the carbonylamino group is used as the alkanoylamino group, the carbon number is preferably 1 to 12);

Hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; carboxyl group, -CO ₂ M ² (M ² is an alkali metal, preferably lithium, sodium and potassium); sulfonic acid group, -SO ₃ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); nitro; cyano; methoxy; Propionyloxy, Penteyloxy, Hexyloxy, (2-ethyl) Hexyloxy, Heptyloxy, Octyloxy, Nonyloxy, Decyloxy, Undecyloxy A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded to a group such as a dodecyloxy group, a dodecyloxy group, a benzyloxy group, a benzyloxy group, etc., and a group represented by the following formula, etc. or its derivative group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylaminosulfonyl group with carbon number 1 to 10 (preferably octylaminosulfonyl group) (such as the derivatized group) of the carbonyloxy group (when the carbonyloxy group is used as the alkanoyloxy group, the carbon number is preferably 1 to 10);

Methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl)hexylsulfonyl, heptylsulfonyl sulfonyl, octylsulfonyl, nonylsulfonyl, decylsulfonyl, undecylsulfonyl, dodecylsulfonyl, eicosylsulfonyl, phenylsulfonyl, p-Tolylsulfonyl group, etc., and groups represented by the following formula, etc. are bonded to a hydrocarbon group having 1 to 20 carbon atoms (preferably carbon number 1 to 10) or a derivative group thereof (for example, a carboxyl group, a sulfonic acid group, a nitro group) sulfonyl groups such as radicals, hydroxyl groups, halogens (preferably chlorine atoms), alkyl sulfamoyl groups (preferably octyl sulfamoyl groups) and other derivatized groups with carbon numbers from 1 to 10);

Aminocarboxy; N-methylaminocarboxy, N,N-dimethylaminocarboxy, N-ethylaminecarboxy, N,N-diethylaminecarboxy, N-propyl Carboxyl, N,N-dipropylamine carboxyl, N-isopropylamine carboxyl, N,N-diisopropylamine carboxyl, N-butylamine carboxyl, N,N-dibutylamine carboxyl, N-isobutylamine carboxyl, N,N-diisobutylamine carboxyl, N-dibutylamine carboxyl, N,N- Di-tert-butylamine carboxyl, N-tert-butylamine carboxyl, N,N-di-tert-butylamine carboxyl, N-pentylamine carboxyl, N,N-dipentane Aminocarboxy, N-(1-ethylpropyl)carbamoyl, N,N-bis(1-ethylpropyl)carbamoyl, N-hexylcarbamoyl, N,N -Dihexylaminocarboxy, N-(2-ethyl)hexylcarbamoyl, N,N-bis(2-ethyl)hexylcarbamoyl, N-heptylcarbamoyl, N, N-Diheptylaminocarbamoyl, N-Octylaminecarbamoyl, N,N-Dioctylaminecarbamoyl, N-Nonylaminecarbamoyl, N,N-Octylmethylcarbamoyl Carboxyl, N,N-octylbutylamine carboxyl, N,N-dinonylamine carboxyl, N-phenylamine carboxyl, N,N-diphenylamine carboxyl, N ,N-ethylmethylamine carboxyl, N,N-propylmethylamine carboxyl, N,N-isopropylmethylamine carboxyl, N,N-butylmethylamine carboxyl, N-decylaminocarboxy, N,N-decylmethylaminocarboxy, N-undecylaminocarboxy, N,N-undecylmethylcarbamoyl, N- Dodecylamine carboxyl, N,N-dodecylmethylamine carboxyl, N-eicosylamine carboxyl, N,N-eicosylmethylamine carboxyl, N,N-tert-butylmethylcarbamoyl, N,N-phenylmethylcarbamoyl, etc., and groups represented by the following formulas, etc., have one or two carbon atoms of 1 to 20 (in terms of carbon number) 1 to 10 preferably a hydrocarbon group or its derivative group (such as a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylaminosulfonyl group with a carbon number of 1 to 10 (with an octyl group) The sulfasulfonyl group is preferably a derivatized group such as a derivatized group) a substituted carbamoyl group;

Trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluoropentyl, perfluorohexyl, perfluoroheptyl, perfluorooctyl, perfluorononyl, Perfluorodecyl, perfluoroundecyl, perfluorododecyl, perfluoroeicosyl, perfluorocyclohexyl, perfluorophenyl, etc. all hydrogen atoms are substituted with fluorine atoms and the carbon number is 1 to 20 the hydrocarbon group; perfluoroethylmethyl, perfluoropropylmethyl, perfluoroisopropylmethyl, perfluorobutylmethyl, perfluoropentylmethyl, perfluorohexylmethyl, perfluoroheptylmethyl, Perfluorooctylmethyl, perfluorononylmethyl, perfluorodecylmethyl, perfluoroundecylmethyl, perfluorododecylmethyl, perfluoroeicosylmethyl, etc. are all Hydrocarbon group with 1 to 20 carbon atoms substituted by a straight or branched chain alkyl group with 1 to 20 carbon atoms substituted by a fluorine atom; 2-fluorophenyl, 3-fluorophenyl, 4-fluorobenzene Hydrocarbon groups with 1 to 20 carbon atoms (preferably with 1 to 10 carbon atoms) in which the hydrogen atoms of the 2,4,6-trifluorophenyl group are replaced by fluorine; -CO-SH, -CO-S- CH ₃ , -CO-S-CH ₂ CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₂ -CH ₃ , etc. with carbon number 1 to 20 A thiocarbonyl group bonded to an alkyl group (preferably with a carbon number of 2 to 10), -CO-SC ₆ H ₅ and the like, and a thiocarbonyl group bonded to an aryl group with a carbon number of 6 to 20; *-COCO represented by the following formula -R (in the formula, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, among the above-mentioned hydrocarbon groups satisfying 1 to 20 carbon atoms), or a derivative group thereof (for example, a carboxyl group, a sulfonic acid group, a nitro group) base, hydroxyl, halogen (preferably chlorine atom), alkyl sulfamoyl group (preferably octyl sulfamoyl group) and other derivatized bases) of carbon number 1 to 10;

*-NRCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, one of the hydrocarbon groups listed above that satisfies a carbon number of 1 to 20), or a derivative group thereof (for example, a hydrocarbon group having 1 to 20 carbon atoms) Carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylaminosulfonyl group (preferably octylaminosulfonyl group) with carbon number 1 to 10, etc. derivatized group), the R can be the same or different from each other, and can also be bonded to each other to form a ring) base;

*-OCONR ₂ represented by the following formula (in the formula, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, among the above-mentioned hydrocarbon groups satisfying 1 to 20 carbon atoms), or a derivative group thereof (for example, a hydrocarbon group having 1 to 20 carbon atoms) Carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylaminosulfonyl group with carbon number of 1 to 10 (preferably octylaminosulfonyl group) and other derivatized groups), The R can be the same or different from each other, and can also be bonded to each other to form a ring) base;

*-NRCOOR represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, among the above-mentioned hydrocarbon groups satisfying 1 to 20 carbon atoms), or a derivative group thereof (for example, a carboxyl group) , sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkyl sulfamoyl group (preferably octyl sulfamoyl group) and other derivatized bases), the R can be the same or different from each other, and can also be bonded to each other to form a ring) base;

*-OP(O)(OR) ₂ such as *-OP(O)(OCH ₃ ) ₂ (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, among the above-mentioned hydrocarbon groups satisfying carbon 1 to 20), or derivatives thereof (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably a chlorine atom), alkylaminosulfonyl group of carbon number 1 to 10 (with an octyl group) Sulfasulfonyl group is preferably a derivatized group), the R can be the same or different from each other, and can also be bonded to each other to form a ring); *-Si(CH ₃ ) ₃ , *- Si(CH ₂ CH ₃ ) ₃ , *-Si(C ₆ H ₅ ) ₃ and *-Si(CH(CH ₃ ) ₂ ) ₃ etc. *-SiR ₃ (wherein R is a hydrogen atom, carbon number from A hydrocarbon group of 20 (for example, among the above-mentioned hydrocarbon groups satisfying carbon number 1 to 20), or its derivative group (for example, through a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a carbon number 1 to 10 alkyl sulfamoyl groups (with octyl sulfamoyl groups preferably) and other derivatized groups), the R can be the same or different from each other, and can also be bonded to each other to form a ring) base.

Divalent substituents include pendant oxy groups, thio pendant oxy groups, imino groups, imino groups substituted with alkyl groups having 1 to 20 carbon atoms (preferably those having 1 to 10 carbon atoms), An aryl group substituted with an aryl group having 6 to 20 carbon atoms, and the like. Examples of the alkyl-substituted imino group include CH ₃ -N=, CH ₃ -CH ₂ -N=, CH ₃ -(CH ₂ ) ₂ -N=, CH ₃ -(CH ₂ ) ₃ -N = etc. The imino group substituted by an aryl group includes C ₆ H ₅ -N= and the like.

The substituent of the hydrocarbon group having 1 to 40 carbon atoms preferably includes the substituent of group s1. The derivatized group shown below is a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylaminosulfonyl group having 1 to 10 carbon atoms (octylaminosulfonyl group is an octylaminosulfonyl group) A derivatized base such as the best) is preferred.

[group s1]

An oxy group to which a hydrocarbon group having 1 to 20 carbon atoms or its derivative group is bonded on one side; a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative group thereof is bonded; Oxycarbonyl of a derivative group; Amine group; Amine group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or derivatives thereof; Sulfasulfonyl; Sulfasulfonyl group substituted with a hydrocarbon group or its derivative group; carbonylamino group bonded with a hydrocarbon group with a carbon number of 1 to 20 or its derivative group; hydroxyl; halogen atom; -CO ₂ M (preferably a carboxyl group) (M represents A hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO ₃ M (preferably a sulfonic acid group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); nitro group; cyano group ; A carbonyloxy group bound with a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof; A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bound; Carboxyl group substituted with a hydrocarbon group of 1 to 20 carbon atoms or its derivatives; a hydrocarbon group of 1 to 20 carbon atoms with all hydrogen atoms substituted by fluorine atoms; A hydrocarbon group with 1 to 20 carbon atoms substituted by a straight-chain or branched alkyl group; a hydrocarbon group with 1 to 20 carbon atoms substituted with a part of hydrogen atoms by fluorine; a pendant oxy group.

As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, more preferably, the substituent of group s2 is mentioned.

[group s2]

An oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded on one side; a carbonyl group to which a hydrocarbon group having 1 to 10 carbons or a derivative thereof is bonded; Oxycarbonyl of derivative group; amine group; amine group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms; sulfamoyl group; one or two hydrocarbon groups having 1 to 10 carbon atoms or its Derivative group-substituted sulfamoyl group; carbonylamino group bonded with a hydrocarbon group having 1 to 10 carbon atoms or its derivative group; hydroxyl group; fluorine atom, chlorine atom, bromine atom; -CO ₂ M (preferably a carboxyl group) ( M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO ₃ M (preferably a sulfonic acid group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); nitro; cyano group; carbonyloxy group bonded with a hydrocarbon group having 1 to 10 carbon atoms or its derivative; 2 hydrocarbon groups with 1 to 10 carbon atoms or amine carboxyl groups substituted by derivatives thereof; hydrocarbon groups with 1 to 10 carbon atoms substituted with all hydrogen atoms by fluorine atoms; carbon number substituted with all hydrogen atoms by fluorine atoms A hydrocarbon group with a carbon number of 1 to 10 substituted by a linear or branched alkyl group of 1 to 10; a hydrocarbon group with a carbon number of 1 to 10 in which a part of the hydrogen atoms are substituted by fluorine; a pendant oxy group.

The hydrocarbon group having 1 to 40 carbon atoms and having a substituent represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² includes a hydrocarbon group having 1 to 40 carbon atoms having a monovalent or divalent substituent. The hydrocarbon group preferably includes a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms having a monovalent or divalent substituent, and a saturated or unsaturated hydrocarbon group having 3 to 30 carbon atoms having a monovalent or divalent substituent. Alicyclic hydrocarbon group, aromatic hydrocarbon group with 6 to 30 carbon atoms having a monovalent or divalent substituent, or a group formed by combining hydrocarbon groups, and a group having 1 to 30 carbon atoms with a monovalent or divalent substituent , more preferably include: a saturated or unsaturated chain hydrocarbon group with a carbon number of 1 to 20 having a substituent group s1, a saturated or unsaturated alicyclic hydrocarbon group with a carbon number 3 to 20 having a substituent group s1, An aromatic hydrocarbon group having 6 to 20 carbon atoms in group s1 or a group formed by combining hydrocarbon groups, and a group having 1 to 20 carbon atoms in group s1, particularly preferably: the number of carbon atoms in the substituent group having group s2 Saturated or unsaturated chain hydrocarbon group of 1 to 15, saturated or unsaturated alicyclic hydrocarbon group of carbon number 3 to 15 with substituent of group s2, aromatic hydrocarbon group of carbon number of 6 to 15 with substituent of group s2 Or a group formed by combining a hydrocarbon group and having a substituent of group s2 and having 1 to 15 carbon atoms.

The heterocyclic group represented by R ^N1 , R ^N2 , Ar ¹ , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may be monocyclic or polycyclic, and preferably a heterocyclic ring containing a heteroatom as a constituent element of the ring . A nitrogen atom, an oxygen atom, a sulfur atom, etc. are mentioned as a hetero atom.

The carbon number of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, more preferably 3 to 20, more preferably 3 to 18, more preferably 3 to 15, more preferably 3 To 14 is preferred.

等單環系飽和雜環；2,5-二甲基吡咯等吡咯、2-甲基吡唑、3-甲基吡唑等吡唑、咪唑、1,2,3-三唑及1,2,4-三唑等5員環系不飽和雜環；吡啶、嗒

、6-甲基嘧啶等嘧啶、吡

及1,3,5-三

等6員環系不飽和雜環；吲唑、吲哚啉、異吲哚啉、吲哚、吲哚

、苯并咪唑、喹啉、異喹啉、5,6,7,8-四氫(3-甲基)喹

啉、3-甲基喹

啉等喹

啉、喹唑啉、噌啉(cinnoline)、呔

、

啶、嘌呤、喋啶(pteridine)、苯并吡唑、苯并哌啶等縮合二環系雜環；咔唑、吖啶及啡

等縮合三環系雜環；等。 The nitrogen atom-containing heterocycle includes aziridine, azetidine, pyrrolidine, piperidine, and piperidine

Saturated heterocycles such as monocyclic systems; pyrroles such as 2,5-dimethylpyrrole, pyrazoles such as 2-methylpyrazole, 3-methylpyrazole, imidazole, 1,2,3-triazole and 1,2 ,4-triazole and other 5-membered unsaturated heterocycles; pyridine, pyridine

, pyrimidines such as 6-methylpyrimidine, pyridine

and 1,3,5-three

Equal 6-membered ring system unsaturated heterocycle; indazole, indoline, isoindoline, indole, indole

, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoline

Linen, 3-methylquinoline

quinoline

quinazoline, quinazoline, cinnoline,

,

Condensed bicyclic heterocycles such as pyridine, purine, pteridine, benzopyrazole, benzopiperidine; carbazole, acridine and phenanthrene

etc. Condensed tricyclic heterocycles; etc.

烷、1,4-二

烷、1-環戊基二

烷等單環系飽和雜環；1,4-二氧雜螺[4.5]癸烷、1,4-二氧雜螺[4.5]壬烷等二環系飽和雜環；α-乙內酯、 β-丙內酯、γ-丁內酯、γ-戊內酯及δ-戊內酯等內酯系雜環；2,3-二甲基呋喃、2,5-二甲基呋喃等呋喃等5員環系不飽和雜環；2H-哌喃及4H-哌喃等6員環系不飽和雜環；1-苯并呋喃、4-甲基苯并哌喃等苯并哌喃、苯并二

呃(benzodioxole)、

唍(chroman)及異

唍等縮合二環系雜環；二苯并哌喃(xanthene)、二苯并呋喃等縮合三環系雜環；等。 Examples of the oxygen atom-containing heterocycle include ethylene oxide, oxetane, tetrahydrofuran, tetrahydropyran, and 1,3-di

Alkane, 1,4-di

Alkane, 1-cyclopentyldi

Monocyclic saturated heterocycles such as alkane; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; α-acetolactone, Lactone heterocycles such as β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone; furans such as 2,3-dimethylfuran and 2,5-dimethylfuran, etc. 5-membered ring system unsaturated heterocycle; 6-membered ring system unsaturated heterocycle such as 2H-pyran and 4H-pyran; 1-benzofuran, 4-methylbenzopyran and other benzopyran, benzopyran two

Uh (benzodioxole),

chroman and iso

Condensed bicyclic heterocycles such as sulfonium; condensed tricyclic heterocycles such as dibenzopyran (xanthene) and dibenzofuran; and the like.

Examples of the sulfur atom-containing heterocycle include 5-membered saturated heterocycles such as dithiolane; thiane, 1,3-dithiolane, 2- 6-membered saturated heterocyclic ring such as methyl 1,3-dithiane; 5-membered unsaturated heterocycles; condensed bicyclic heterocycles such as benzothiophene; condensed tricyclic heterocycles such as thianthrene, dibenzothiophene, etc.

唑等

唑、2-甲基異

唑、3-甲基異

唑等異

唑等單環系不飽和雜環；苯并

唑、苯并異

唑、苯并

、苯并二

烷、苯并咪唑啉等縮合二環系雜環；啡

等縮合三環系雜環；等。 Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 2-methyl-2-piperidone, and the like Monocyclic saturated heterocycle; 4-methyl

azole, etc.

azole, 2-methyliso

azole, 3-methyliso

azole isoiso

Monocyclic unsaturated heterocycles such as azoles; benzos

azole, benziso

azoles, benzos

, benzodi

Condensed bicyclic heterocycles such as alkane, benzimidazoline, etc.;

etc. Condensed tricyclic heterocycles; etc.

等縮合三環系雜環；等。 Examples of the heterocycle containing a nitrogen atom and a sulfur atom include monocyclic heterocycles such as thiazoles such as 3-methylthiazole and 2,4-dimethylthiazole; condensed bicyclic heterocycles such as benzothiazole;

etc. Condensed tricyclic heterocycles; etc.

The above-mentioned heterocycle may be a group formed by combining the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.

In addition, the above-mentioned heterocyclic ring may be represented by the following formula.

In addition, the above-mentioned heterocyclic group may be a heterocyclic group formed by bonding two or more of R ¹ to R ³ and R ⁵ to R ⁸ . Such a heterocyclic group has a ring structure of two or more rings together with the benzene ring to which R ¹ to R ³ and R ⁵ to R ⁸ are bonded. Examples of the ring structure having two or more rings include the structures of the following formulae.

In addition, the bonding site of the above-mentioned heterocyclic ring is a part from which any hydrogen atom contained in each ring has been removed.

The heterocyclic group represented by R ^N1 , R ^N2 , Ar ¹ , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may have a substituent. Examples of the substituent include the same substituents that the hydrocarbon groups represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may have. In addition, when the said heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group may be couple|bonded with this nitrogen atom as a substituent.

Preferable examples of the substituent include the same substituents that the hydrocarbon groups represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may have.

The heterocyclic group having a substituent represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² includes a heterocyclic group having a monovalent or divalent substituent, preferably a group having a group The heterocyclic group of the substituent of s1 is more preferably a heterocyclic group of the substituent of the group s2.

The number of substituents (first substituents) which the above-mentioned hydrocarbon group or heterocyclic group may have may be one or two or more, and two or more substituents may be the same or different independently of each other. Furthermore, the aforementioned first substituent may have another substituent (second substituent) bonded to a hydrocarbon group contained in a part of the first substituent. The second substituent may be selected from the same groups as the first substituent.

-CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) of R ¹ to R ⁸ are described below ) ₂ , -CON(R ¹⁰² ) ₂ , -N(R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N(R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON(R ¹⁰² ) ₂ , halogen atom, -SO ₃ M and -CO ₂ M.

-CO-R ¹⁰ includes: carboxyl; acetyl, propionyl, butyryl, 2,2-dimethylpropionyl, pentamyl, hexanoyl, (2-ethyl)hexanoyl base, heptylyl, octylyl, nonylyl, decylyl, undecylyl, dodecyl, hexadecyl, benzyl, etc., and the bases represented by the above formulas are bonded with carbon number 1 to 40 (preferably carbon number 1 to 20) hydrocarbon group or its derivative group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), carbon number 1 to 10 alkyl group A carbonyl group of a sulfamoyl group (preferably a derivatized group such as an octyl sulfamoyl group) (when the carbonyl group is used as an amide group, the number of carbon atoms is 2 to 41), etc., preferably, those with carbon number bonded 1 to 11 (preferably carbon number of 1 to 10) hydrocarbon group or carbonyl group of its derivative group (when the carbonyl group is used as an alkanoyl group, carbon number of 2 to 12 is more preferable) and the like.

-COO-R ¹⁰¹ includes: methoxycarbonyl, ethoxycarboxy, propoxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) yl) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenoxycarbonyl, eicosyloxy A carbonyl group, etc., and the group represented by the above formula, etc. are bonded to a hydrocarbon group with a carbon number of 1 to 40 (preferably a carbon number of 1 to 20) or its derivative group (for example, through a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen group, etc.) (preferably a chlorine atom), an oxycarbonyl group bound to an alkylaminosulfonyl group having 1 to 10 carbon atoms (preferably a derivatized group such as an octylaminosulfonyl group), etc., preferred examples include An oxycarbonyl group or the like to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded.

-OCO-R ¹⁰² includes: methoxyloxy; acetyloxyl, propionyloxy, butyryloxy, 2,2-dimethylpropionyloxy, pentamyloxy, hexyloxy , (2-ethyl) hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, hexadecyloxy , benzyloxy, etc., and the base represented by the above formula, etc. are bonded with a hydrocarbon group having a carbon number of 1 to 40 (preferably a carbon number of 1 to 20). A hydrocarbon group having 1 to 10 carbon atoms or its derivative group (such as a carbonyloxy group, an alkylamine sulfonyl group (with an octane Preferably, a sulfamoyl group is a derivatized group), a carbonyloxy group (when the carbonyloxy group is an acyloxy group, the number of carbon atoms is 2 to 41) and the like.

-COCO-R ¹⁰² includes: methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) Hexyloxalyl, Heptyloxalyl, Octyloxalyl, Nonyloxalyl, Decyloxalyl, Undecyloxalyl, Dodecyloxalyl, Eicosanyl Acryloyl, cyclopentyloxalyl, cyclohexyloxalyl, phenyloxalyl, p-tolyloxalyl, etc., and the bases represented by the above formulas are bonded with carbon number 1 to 40 (with carbon number 1). To 20 preferably) hydrocarbon group or its derivative group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), carbon number 1 to 10 alkylamine sulfonyl group (with octyl group) The sulfasulfonyl group is preferably a derivatized group such as a oxalyl group and the like.

-OR ¹⁰² includes: hydroxy; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, 2nd butoxy, 3rd butoxy, pentoxy , hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl)hexyloxy, eicosyloxy, 1 -Phenylethoxy, 1-methyl-1-phenylethoxy, phenoxy, 2,3-dimethylphenoxy, 2,4-dimethylphenoxy, 2,5- Dimethylphenoxy, 2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3,5-dimethylphenoxy, 2,2-dicyanophenoxy , 2,3-dicyanophenoxy, 2,4-dicyanophenoxy, 2,5-dicyanophenoxy, 2,6-dicyanophenoxy, 3,4-dicyanophenoxy Cyanophenoxy, 3,5-dicyanophenoxy, 4-methoxyphenoxy, 2-methoxyphenoxy, 3-methoxyphenoxy, 4-ethoxybenzene Oxy group, 2-ethoxyphenoxy group, 3-ethoxyphenoxy group, etc., and the group represented by the above formula, etc., are bonded to a hydrocarbon group having 1 to 40 carbon atoms (preferably carbon number 1 to 20) or Derivative groups (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably a chlorine atom), alkylaminosulfonyl group having 1 to 10 carbon atoms (preferably octylaminosulfonyl group), etc. The oxy group etc. of the derivatized group) preferably include an oxy group etc. to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative group thereof is bonded.

-SO ₂ -R ¹⁰¹ may include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethylsulfonyl) ) hexylsulfonyl, heptylsulfonyl, octylsulfonyl, nonylsulfonyl, decylsulfonyl, undecylsulfonyl, dodecylsulfonyl, eicosyl Sulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group, etc., and the group represented by the above formula, etc. are bonded to a hydrocarbon group with a carbon number of 1 to 40 (preferably a carbon number of 1 to 20) or its derivative group ( For example, a group derivatized with a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylaminosulfonyl group having a carbon number of 1 to 10 (preferably an octylaminosulfonyl group), etc. ), preferably a sulfonyl group and the like to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative group thereof is bonded are exemplified.

-SO ₂ N(R ¹⁰² ) ₂ may include sulfamoyl; N-methyl sulfamoyl, N-ethyl sulfamoyl, N-propyl sulfamoyl, N-isopropyl Sulfamoyl, N-Butyl Sulfonyl, N-Isobutyl Sulfonyl, N-Second-Butyl Sulfonyl, N-Terti-Butyl Sulfonyl, N-Amyl Sulfamoyl, N-(1-ethylpropyl) sulfamoyl, N-hexyl sulfamoyl, N-(2-ethyl)hexyl sulfamoyl, N-heptyl sulfamoyl , N-Octylaminosulfonyl, N-nonylaminosulfonyl, N-decylaminosulfonyl, N-undecylaminosulfonyl, N-dodecylaminosulfonyl, N-eicosylaminosulfonyl group, N-phenylaminosulfonyl group, etc., and the group represented by the above formula, etc. correspond to a hydrocarbon group having 1 to 40 carbon atoms (preferably, 1 to 20 carbon atoms). or its derivative group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylaminosulfonyl group with carbon number 1 to 10 (preferably octylaminosulfonyl group) etc. derivatized group) substituted sulfasulfonyl group, etc.; Sulfonyl, N,N-propylmethylsulfamoyl, N,N-dipropylsulfamoyl, N,N-isopropylmethylsulfamoyl, N,N-diisopropyl Sulfasulfonyl, N,N-tert-butylmethylsulfamoyl, N,N-diisobutylaminesulfonyl, N,N-di-2-butylaminesulfonyl, N,N-diisobutylaminesulfonyl Tertiary-butylaminosulfonyl, N,N-butylmethylaminosulfonyl, N,N-dibutylaminosulfonyl, N,N-dipentylaminosulfonyl, N,N-bis( 1-Ethylpropyl) sulfamoyl, N,N-dihexyl sulfamoyl, N,N-bis(2-ethyl)hexyl sulfamoyl, N,N-diheptyl sulfamoyl base, N,N-octylmethylaminosulfonyl, N,N-dioctylaminosulfonyl, N,N-dinonylaminosulfonyl, N,N-decylmethylaminosulfonyl base, N,N-undecylmethylaminosulfonyl, N,N-dodecylmethylaminosulfonyl, N,N-eicosylmethylaminosulfonyl, N,N-benzene Methylaminosulfonyl group, N,N-diphenylaminesulfonyl group, etc., and the group represented by the above formula, etc., through two hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or Derivative groups (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably a chlorine atom), alkylaminosulfonyl group having 1 to 10 carbon atoms (preferably octylaminosulfonyl group), etc. derivatized group) substituted sulfamoyl group, etc.

-CON(R ¹⁰² ) ₂ includes: carbamoyl; N-methyl carbamoyl, N-ethylamine carboxy, N-propylamine carboxy, N-isopropyl carbamide Carboxyl, N-butylamine carboxyl, N-isobutylamine carboxyl, N-2-butylamine carboxyl, N-tert-butylamine carboxyl, N-amylamine carboxyl Carboxyl, N-(1-ethylpropyl)aminocarboxy, N-hexylaminocarboxy, N-(2-ethyl)hexylcarbamoyl, N-heptylaminocarboxy, N -Octylamine carboxyl, N-nonylamine carboxyl, N-decylamine carboxyl, N-undecylamine carboxyl, N-dodecylamine carboxyl, N- Eicosylamine carboxyl group, N-phenylamine carboxyl group, etc., and the group represented by the above formula, etc., through a hydrocarbon group with a carbon number of 1 to 40 (preferably a carbon number of 1 to 20) or its derivative group (For example, it is derivatized with a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylaminosulfonyl group having 1 to 10 carbon atoms (preferably an octylaminosulfonyl group), etc. base) substituted carbamoyl, etc.; -Propylmethylamine carboxyl, N,N-dipropylamine carboxyl, N,N-isopropylmethylamine carboxyl, N,N-diisopropylamine carboxyl, N ,N-tert-butylmethylamine carboxyl, N,N-diisobutylamine carboxyl, N,N-di-tert-butylamine carboxyl, N,N-di-tert-butylamine carboxyl Carboxyl, N,N-butylmethylamine carboxyl, N,N-dibutylamine carboxyl, N,N-butyloctyl carboxyl, N,N-dipentylamine carboxyl , N,N-bis(1-ethylpropyl)amine carboxyl, N,N-dihexylamine carboxyl, N,N-bis(2-ethyl)hexylamine carboxyl, N,N -Diheptylamine carboxyl, N,N-octylmethylamine carboxyl, N,N-dioctylamine carboxyl, N,N-dinonylamine carboxyl, N,N- Decylaminocarboxy, N,N-undecylmethylaminecarboxy, N,N-dodecylmethylaminecarboxy, N,N-eicosylmethylaminecarboxy group, N,N-phenylmethylamine carboxyl group, N,N-diphenylamine carboxyl group, etc., and groups represented by the above formulas, etc. preferably) hydrocarbon group or its derivative group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylaminosulfonyl group with carbon number 1 to 10 (with octylaminesulfonyl group) The carbamide group is preferably a derivatized group such as ) substituted carbamoyl group, and the like, preferably, carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof.

-N(R ¹⁰² ) ₂ includes: amino; N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-second-butylamino, N-tert-butylamino, N-pentylamino, N-hexylamino, N-(2-ethyl)hexylamino , N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-diamino Dodecylamine, N-phenylamine, etc., and the groups represented by the above formulas, etc., are represented by a hydrocarbon group with a carbon number of 1 to 40 (preferably a carbon number of 1 to 20) or its derivative group (such as a carboxyl group, a sulfonic acid group) Amino group substituted by acid group, nitro group, hydrocarbon group, halogen (preferably chlorine atom), alkyl sulfamoyl group (preferably octyl sulfamoyl group) and other derivatized groups of carbon number 1 to 10 etc.; N,N-dimethylamino, N,N-ethylmethylamino, N,N-diethylamino, N,N-propylmethylamino, N,N-dipropyl amino, N,N-isopropylmethylamine, N,N-diisopropylamine, N,N-tert-butylmethylamine, N,N-diisobutylamine, N ,N-di-2-butylamine, N,N-di-tert-butylamine, N,N-butylmethylamine, N,N-dibutylamine, N,N-dipentylamine base, N,N-bis(1-ethylpropyl)amine, N,N-dihexylamine, N,N-bis(2-ethyl)hexylamine, N,N-diheptylamine group, N,N-dioctylamino, N,N-dinonylamino, N,N-decylmethylamino, N,N-undecylmethylamino, N,N- Dodecylmethylamine, N,N-eicosylmethylamine, N,N-phenylmethylamine, N,N-diphenylamine, etc., and groups represented by the above formulas etc. through 2 hydrocarbon groups with 1 to 40 carbon atoms (preferably with 1 to 20 carbon atoms) or derivatives thereof (for example, through carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), carbon number 1 to 10 alkyl sulfamoyl groups (the derivatized groups such as octyl sulfamoyl groups are preferred)) substituted amine groups, etc., preferably 1 or 2 carbon atoms of 1 to 10 can be exemplified. Hydrocarbyl or its derivative substituted amine group, etc.

-NHCO-R ¹⁰² includes: carboxylamino group; acetamidoamino group, propionylamino group, butylaminoamino group, 2,2-dimethylpropionylamino group, pentanylamino group, Hexylamino, (2-ethyl)hexylamino, heptylamino, octylamino, nonylamino, decanoylamino, undecylamino, dodecylamino amine group, hexadecanoyl amine group, benzyl amine group, etc., and the group represented by the above formula, etc., are bonded to a hydrocarbon group with a carbon number of 1 to 40 (preferably a carbon number of 1 to 20) or its derivatives Derivatized with a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylaminosulfonyl group having a carbon number of 1 to 10 (preferably an octylaminosulfonyl group), etc. the carbonylamino group (the carbonylamino group is an acylamino group, the carbon number is 1 to 40), etc., preferably a carbonyl group to which a hydrocarbon group with a carbon number of 1 to 10 or a derivative thereof is bonded An amino group (when the carbonylamino group is an alkanoylamino group, the number of carbon atoms is more preferably 1 to 10) and the like.

-NHCON(R ¹⁰² ) ₂ includes the above-mentioned bases and the like.

As for -NHCOOR ¹⁰² , the above-mentioned base etc. are mentioned.

-OCON(R ¹⁰² ) ₂ includes the above-mentioned bases and the like.

The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or the like.

M of -SO ₃ M and -CO ₂ M includes a hydrogen atom; an alkali metal atom such as a lithium atom, a sodium atom, and a potassium atom, and preferably includes a hydrogen atom, a sodium atom, and a potassium atom.

The above -CO-R ¹⁰² , -COO-R ¹⁰² , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰² , -SO ₂ N(R ¹⁰² ) ₂ , -CON(R ¹⁰² ) ₂ , -N(R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCON(R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON(R ¹⁰² ) ₂ may contain a substituent (first substituent) of 1 One, two or more, and two or more substituents may be the same or different independently of each other. In addition, the aforementioned first substituent may bond another substituent (second substituent) to the hydrocarbon group contained in a part thereof. The second substituent may be selected from the same groups as the first substituent.

The carbon number of the aromatic hydrocarbon group represented by Ar ¹ is 6 to 40, preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15. The aromatic hydrocarbon group may be monocyclic or polycyclic.

The aromatic hydrocarbon group represented by Ar ¹ includes a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2,3-dimethylphenyl group, a 2,4-dimethylphenyl group, and a 2,5-dimethylphenyl group. -Dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, o-isopropylphenyl, m-isopropylphenyl , p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, mesityl, 2,6-bis(2-propyl)phenyl , 2,4,6-trimethylphenyl, 1-naphthyl, 2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro- Aromatic hydrocarbon groups such as 2-naphthyl, perylene, phenanthrenyl and anthracenyl; groups formed by combining these groups, etc.

The aromatic hydrocarbon group represented by Ar ¹ may have a substituent. Examples of the substituent include the same substituents that the hydrocarbon groups represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may have.

The preferred ones of the substituents are the same as those of the substituents which the hydrocarbon groups represented by R ^N1 , R ^N2 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may have.

R ^N1 is an aliphatic hydrocarbon group, an aromatic hydrocarbon group, an aralkyl group, a (cycloalkyl) alkyl group, an aliphatic hydrocarbon group substituted with a hydroxyl group, and an oxy group having a hydrocarbon group having 1 to 20 carbon atoms bonded to one side The substituted aliphatic hydrocarbon group is preferably a linear or branched chain alkyl group, a linear or branched chain alkenyl group, a cycloalkyl group, and the following formulae (P-1) to (P-10) are represented more preferably, aralkyl, (cycloalkyl) alkyl, hydroxy-substituted straight-chain or branched-chain alkyl, and alkoxy-substituted straight-chain or branched-chain alkyl, The groups represented by the straight-chain or branched-chain alkyl groups and the below-mentioned formulae (P-1) to (P-10) are still more preferable.

R ^N2 is aliphatic substituted with aliphatic hydrocarbon group, aralkyl group, (cycloalkyl) alkyl group, aliphatic hydrocarbon group substituted with hydroxy, and an oxy group having a hydrocarbon group having 1 to 20 carbon atoms bonded on one side Hydrocarbon groups are preferably straight-chain or branched-chain alkyl groups, straight-chain or branched-chain alkenyl groups, cycloalkyl groups, aralkyl groups, (cycloalkyl) alkyl groups, straight chain substituted with hydroxyl groups A straight-chain or branched-chain alkyl group and an alkoxy-substituted straight-chain or branched-chain alkyl group are more preferred, and a straight-chain or branched-chain alkyl group is even more preferred. R ^N1 and R ^N2 may be the same or different.

Ar ¹ is preferably a group represented by the following formulae (P-1) to (P-10).

R ⁴ is preferably a hydrogen atom, and R ¹ to R ⁸ are more preferably hydrogen atoms.

The compound represented by the formula (I) may have a partial structure shown below in addition to the above-mentioned groups.

Preferably, R ^N1 and R ^N2 are independently of each other a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent, Ar ¹ is an aromatic hydrocarbon group with 6 to 40 carbon atoms that may have a substituent group, and R ¹ to R ⁸ are independently of each other are hydrogen atoms, more preferably, R ^N1 and R ^N2 are independently of each other a hydrocarbon group with 1 to 20 carbon atoms that may have a substituent, Ar ¹ is an aromatic hydrocarbon group with 6 to 20 carbon atoms that may have a substituent group, R ¹ to R ⁸ are independently of each other a hydrogen atom, and more preferably, R ^N1 and R ^N2 are independently of each other a C 1-20 alkyl group or an aryl group which may have a substituent, and Ar ¹ may have a substituent The aromatic hydrocarbon group with 6 to 20 carbon atoms, R ¹ to R ⁸ are independently hydrogen atoms, and more preferably, R ^N1 is an alkyl group or an aryl group with 1 to 10 carbon atoms that may have a substituent, R ^N2 is an optionally substituted alkyl group having 1 to 10 carbon atoms, Ar ¹ is an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, and R ¹ to R ⁸ are independently hydrogen atoms.

In the compound represented by the formula (I), A ^g- represents a g-valent anion. g is an integer of 1 to 14, preferably an integer of 1 to 10, more preferably an integer of 1 to 8, still more preferably an integer of 1 to 6, particularly preferably an integer of 1 to 4.

A ^g- includes known anions. Specific examples of ^Ag- include halide ions such as fluoride ion, chloride ion, bromide ion, and iodide ion; OH ⁻ ; CN ⁻ ; NO ₃ ⁻ ; NO ₂ ⁻ ; ClO ⁻ ; ClO ₂ ^- ; ClO ₃ ^- ; ClO ₄ ^- ; MnO ₄ ^- ; CH ₃ CO ₂ ^- , C ₆ H ₅ CO ₂ ^- ; Tosylate anion; HCO ₃ ^- ; H ₂ PO ₄ ^- ; HSO ₄ ^- ; HS ^- ; SCN ^- ; H(COO) ₂ ^- ; [Al(OH) ₄ ] ^- , [Al(OH) ₄ (H ₂ O) ₂ ] ^- ; [Ag(CN) ₂ ] ^- ; [Cr(OH) ₄ ] ^- ; [AuCl ₄ ] ^- ; O ^2- ; S ^2- ; O ₂ ^2- ; SO ₄ ^2- , HSO ₄ ^- , SO ₃ ^2- , S ₂ O ₃ ^2- ; CO ₃ ^2- ; CrO ₄ ^2- ; Cr ₂ O ₇ ^2- ; (COO) ₂ ^2- ; HPO ₄ ^2- ; [Zn(OH) ₄ ] ^2- ; [Zn(CN) ₄ ] ^2- ; [CuCl ₄ ] ^2- ; PO ₄ ^3- ; [Fe(CN) ₆ ] ^3- ; [Ag(S ₂ O ₃ ) ₂ ] ^3- ; [Fe(CN) ₆ ] ^4- ; CH ₃ O ^- , CH ₃ CH ₂ O ^- , (CH ₃ ) ₃ CO ^- alkoxy anion with carbon number 1 to 20 such as C ₆ H ₅ O ^- aryloxy anion with carbon number 6 to 20 such as C 6 H 5 O - fluorine-containing anion; and at least one element in the group consisting of phosphorus and oxygen as an anion of essential elements, etc.

From the viewpoint of improving heat resistance or reducing sublimation, A ^g- is an anion containing a fluorine-containing anion or an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements Preferably, an anion containing at least one element selected from the group consisting of tungsten and phosphorus and oxygen as essential elements, or a fluorine-containing anion, preferably containing an element selected from the group consisting of tungsten and phosphorus. It is more preferable that at least one element and oxygen are anions of essential elements.

Examples of the fluorine-containing anions include CF ₃ CO ₂ ^- and groups represented by formulae (III), (IV), (V) and (VI).

[In formula (III), W ³ and W ⁴ independently represent a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms, or represent that W ³ and W ⁴ are a fluorinated fluorine atom having 1 to 4 carbon atoms formed together Alkanediyl. ]

[In formula (IV), W ⁵ to W ⁷ each independently represent a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms. ]

[In formula (V), Y ¹ represents a fluorinated alkanediyl group having 1 to 4 carbon atoms. ]

[In formula (VI), Y ² represents a fluorinated alkyl group having 1 to 4 carbon atoms. ]

In the formulae (III), (IV) and (VI), the fluorinated alkyl group having 1 to 4 carbon atoms is preferably a perfluoroalkyl group. Examples of the perfluoroalkyl group include -CF ₃ , -CF ₂ CF ₃ , -CF ₂ CF ₂ CF ₃ , -CF(CF ₃ ) ₂ , -CF ₂ CF ₂ CF ₂ CF ₃ , -CF ₂ CF ( CF ₃ ) ₂ , -C(CF ₃ ) ₃ and the like.

In formulas (III) and (V), the fluorinated alkanediyl group having 1 to 4 carbon atoms is preferably a perfluoroalkanediyl group, and examples include: -CF ₂ -, -CF ₂ CF ₂ -, -CF ₂ CF ₂ CF ₂ -, -C(CF ₃ ) ₂ -, -CF ₂ CF ₂ CF ₂ CF ₂ - and the like.

The anions represented by formula (III) (hereinafter also referred to as "anion (III)") include the anions (hereinafter also referred to as "anion (III)") represented by formula (III-1) to formula (III-6), respectively. 1)" to "Anion (III-6)").

Examples of the anion represented by the formula (IV) (hereinafter also referred to as "anion (IV)") include the anion represented by the formula (IV-1).

Anions represented by formula (V) (hereinafter also referred to as "anions (V)") include anions (hereinafter also referred to as "anions (V-)" represented by formulas (V-1) to (V-4), respectively. 1)" to "Anion (V-4)").

The anions represented by the formula (VI) (hereinafter also referred to as "anions (VI)") include the anions (hereinafter also referred to as "anions (VI-)" represented by the formulas (VI-1) to (VI-4), respectively. 1)" to "Anion (VI-4)").

The fluorine-containing anion may be at least one anion selected from the group consisting of CF ₃ CO ₂ ⁻ , anion (III), anion (IV), anion (V), and anion (VI). Among them, CF ₃ CO ₂ ^- , anion (III-1), anion (III-2), anion (III-6), anion (IV-1), anion (V-1), anion (VI-1) , anion (V1-2), and anion (V1-3) are preferred, and CF ₃ CO ₂ ^- , anion (III-2), anion (IV-1), and anion (VI-1) are more preferred.

Examples of the anions include at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements. The anions of heteropolyacids or isopolyacids containing tungsten as an essential element are preferred, and the anions of phosphotungstic acid, silicotungstic acid, and tungsten-based isopolyacids are more preferred. When the anion is used in, for example, the coloring compound represented by the formula (I) having a fluorine-containing anion (preferably anion (VI-1)), anion exchange is performed, which contributes to the improvement of heat resistance.

Examples of such anions containing heteropolyacids or isopolyacids having tungsten as an essential element include Keggin-type phosphotungstic acid ions α-[PW ₁₂ O ₄₀ ] ^3- , Dawson-type phosphorus Tungstic acid ions α-[P ₂ W ₁₈ O ₆₂ ] ^6- , β-[P ₂ W ₁₈ O ₆₂ ] ^6- , gram gold silicotungstic acid ions α-[SiW ₁₂ O ₄₀ ] ^4- , β-[ SiW ₁₂ O ₄₀ ] ^4- , γ-[SiW ₁₂ O ₄₀ ] ^4- , and other 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- and the like. Among them, it is better to use grams of gold-type phosphotungstic acid ions α-[PW ₁₂ O ₄₀ ] ^3- .

As the compound (I), the compounds shown in Tables 1 to 7 or their alkali metal salts can be exemplified.

In addition, in the following Tables 1 to 7, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tertiary butyl group, "Hex" represents a hexyl group, and "Oct" represents a Octyl, "2EH" stands for 2-ethylhexyl, "CHM" stands for cyclohexylmethyl, "CH" stands for cyclohexyl, "BZ" stands for benzyl, "NPR" stands for propyl, "IPR" stands for isopropyl "IBu" represents isobutyl, "EOE" represents -CH ₂ CH ₂ OCH ₂ CH ₃ , "ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents -CO-CH _3. "COE" means -COO-CH ₂ CH ₃ , "OCM" means -OCO-CH ₃ , "OME" means -O-CH ₃ , "SOT" means tosyl, "SNH" means -SO ₂ NH-CH ₂ CH(CH ₂ CH ₃ )((CH ₂ ) ₃ CH ₃ ), "SN2" means -SO ₂ N(CH ₃ )((CH ₂ ) ₇ CH ₃ ), "CNM" means -CONHCH ₃ , "CN2" means -CON(CH ₃ )C ₆ H ₅ , "NPH" means -NHC ₆ H ₅ , "NOT" means -N((CH ₂ ) ₇ CH ₃ ) ₂ , "NCO" means -NHCO( (CH ₂ ) ₄ CH ₃ ), "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO2" represents a nitro group, and "SUA" represents -SO ₃ H, "CBA" stands for -CO ₂ H, "CHO" stands for -CHO, "OCH" stands for -OCOH, "OH" stands for -OH, "SFM" stands for -SO ₂ NH ₂ , "CBM" stands for -CONH ₂ , "NH2" represents _-NH2 , "NCH" represents -NHCOH, "III-1" to "III-6" represent anion (III-1) to anion (III-6), "IV-1" represents anion ( IV-1), "V-1" to "V-4" represent anions (V-1) to anions (V-4), "VI-1" to "VI-4" represent anions (VI-1) to The anions (VI-4), "P-1" to "P-10" represent groups represented by the formulae (P-1) to (P-10).

In formulas (P-1) to (P-10), ● represents a bonding bond.

For example, compound (I-1) is a compound represented by formula (I-1).

From the viewpoint of easy synthesis, compound (I) is preferably compound (I-1) to compound (I-163) and compound (I-247) to compound (I-266), and compound (I-1) is preferred. ) to compound (I-80) and compound (I-247) to compound (I-266), more preferably, compound (I-1) to compound (I-40) and compound (I-61) to compound (I) -80) is still more preferable, especially compound (I-23), compound (I-33), compound (I-73) and compound (I-74).

Compound (I) of the present invention can be obtained by combining a compound represented by formula (II) (hereinafter, also referred to as compound (II)) and a compound represented by formula (II-1) (hereinafter, also referred to as compound (II)) -1)) can be obtained by reaction, and it can also be obtained by further reacting the obtained compound with a compound containing at least one element selected from the group consisting of tungsten, silicon and phosphorus and oxygen as essential elements .

(R^N2)_gA' (II-1)[式(II)及式(II-1)中，R¹至R⁸、R^N1、R^N2、Ar¹及g表示與上述相同之意。A’表示對上述A^g-賦予g個電子者。]

(R ^N2 ) _g A' (II-1) [In formula (II) and formula (II-1), R ¹ to R ⁸ , R ^N1 , R ^N2 , Ar ¹ and g have the same meanings as described above. A' represents that which has given g electrons to the above-mentioned A ^g- . ]

The compound represented by formula (II-1) includes an alkylating agent. Examples of the alkylating agent include alkyl halides such as alkyl halides having 1 to 10 carbon atoms, preferably 1 to 3 carbon atoms (chloromethane, methyl bromide, methyl iodide, etc.); preferably Carbon number 2 to 10, more preferably carbon number 2 to 6, more preferably carbon number 2 to 4 dialkyl carbonate (dimethyl carbonate or diethyl carbonate, etc.); preferably carbon number 1 to 10, more preferably carbon number 1 to 6, more preferably carbon number 1 to 4 dialkyl sulfate (dimethyl sulfate or diethyl sulfate, etc.); preferably carbon number 2 to 10, more preferably It is carbon number 2 to 6, more preferably carbon number 2 to 4 alkyl alkanesulfonate (methyl methane sulfonate, ethyl ethane sulfonate, ethyl methane sulfonate, methyl ethane sulfonate, Methyl trifluoromethanesulfonate, ethyl trifluoromethanesulfonate, etc.).

The aforementioned alkylating agent is preferably a methylating agent, an ethylating agent, a propylating agent, a butylating agent, etc., more preferably a methylating agent.

The amount of the alkylating agent used is preferably 1 mol or more and 20 mol or less, more preferably 1 mol or more and 10 mol or less, relative to 1 mol of the compound (II).

The reaction temperature in the aforementioned reaction is preferably 0 to 150°C, more preferably 10 to 100°C. In order to make the coloring compound precursor represented by the formula (I) sufficiently soluble, it may be premixed with a predetermined organic solvent at about 70 to 100°C. The reaction time is preferably 10 minutes to 24 hours, more preferably 1 to 12 hours.

From the viewpoint of yield, it is preferable to carry out the reaction in an organic solvent. Examples of the organic solvent include aromatic hydrocarbon solvents such as toluene and xylene; aliphatic hydrocarbon solvents such as hexane; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, dichloromethane, and chloroform; methanol, ethanol, isopropanol, and butyl alcohol. Alcohol solvents such as alcohol; nitro hydrocarbon solvents such as nitrobenzene; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; ether solvents such as diethyl ether and tetrahydrofuran; nitrile solvents such as acetonitrile; Amide solvents such as methylformamide, N,N-dimethylacetamide, and 1-methyl-2-pyrrolidone, etc., preferably include aromatic hydrocarbon solvents, more preferably include toluene and Xylene.

The amount of the organic solvent used is preferably 1 part by mass or more and 300 parts by mass or less, more preferably 1 part by mass or more and 100 parts by mass or less, relative to 1 part by mass of compound (II).

The method for obtaining the compound from the reaction mixture is not particularly limited, and various known methods can be employed. For example, a method of filtering the reaction mixture, washing with a solvent such as an aromatic hydrocarbon solvent such as toluene, and drying the obtained residue can be mentioned. If necessary, it can also be further purified by using a solvent for recrystallization or by silica gel separation column chromatography. The obtained compound becomes, for example, a compound represented by formula (I).

Next, a method of exchanging the anion of the compound represented by the formula (I) may be employed, and the method may include adding an element containing at least one element selected from the group consisting of tungsten, silicon, and phosphorus and oxygen as essential elements. compounds, etc.

Compounds containing at least one element selected from the group consisting of tungsten, silicon, and phosphorus, and oxygen as essential elements (hereinafter, also referred to as anion exchangers in this specification) can be produced by known common methods. Commercially available products can be used as they are. Such compounds include, for example, corresponding heteropoly acid salts, isopoly acid salts, silicates, phosphates, etc., and may also be phosphotungstic acid, silicotungstic acid, phosphomolybdic acid, silico-molybdic acid, and the like.

The use amount of the anion exchanger is preferably 0.01 mol or more and 5 mol or less, more preferably 0.01 mol or more and 1 mol or less, relative to 1 mol of the coloring compound represented by the formula (I).

The reaction temperature is preferably 0 to 150°C, more preferably 10 to 100°C. The reaction time is preferably 10 minutes to 36 hours, more preferably 10 minutes to 24 hours.

From the viewpoint of yield, the reaction is preferably carried out in water, an organic solvent or a mixture of these.

Examples of the organic solvent include aromatic hydrocarbon solvents such as toluene and xylene; aliphatic hydrocarbon solvents such as hexane; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, dichloromethane, and chloroform; methanol, ethanol, isopropanol, and butyl alcohol. Alcohol solvents such as alcohol; nitro hydrocarbon solvents such as nitrobenzene; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; ether solvents such as diethyl ether and tetrahydrofuran; nitrile solvents such as acetonitrile; Methylformamide, N,N-dimethylacetamide, 1-methyl-2-pyrrolidone and other amide solvents; etc.

The solvent system is preferably water, alcohol solvent, ketone solvent, ether solvent, nitrile solvent, amide solvent and mixtures thereof, more preferably water, alcohol solvent, ketone solvent, nitrile solvent, amide solvent and mixtures thereof , water, alcohol solvents and mixtures of these are more preferred, especially water, methanol and mixtures of these.

The amount of the solvent used is preferably 1 part by mass or more and 1,000 parts by mass or less, more preferably 10 parts by mass or more and 500 parts by mass or less, relative to 1 part by mass of the compound represented by the formula (I).

In this method, the anion of the compound represented by the formula (I) is exchanged, and it becomes a compound suitable for improving heat resistance or reducing sublimation.

Compound (II) can be obtained by making the compound represented by formula (VII) (hereinafter, also referred to as compound (VII)) and the compound represented by formula (VIII) (hereinafter, also referred to as compound (VIII)) in the presence of a base produced by the reaction.

[式(VII)及式(VIII)中，R¹至R³、R⁵至R⁸、R^N1及Ar¹表示與上述相同意思。R⁹表示碳數1至20的烷基。]

[In formula (VII) and formula (VIII), R ¹ to R ³ , R ⁵ to R ⁸ , R ^N1 and Ar ¹ have the same meanings as above. R ⁹ represents an alkyl group having 1 to 20 carbon atoms. ]

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ⁹ include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl, and preferably An alkyl group having 1 to 6 carbon atoms is exemplified.

Examples of the base include organic bases such as triethylamine and piperidine, and the amount of the base used is usually 0.05 to 20 mol per 1 mol of compound (VII).

The amount of compound (VIII) used is usually 1 to 10 mol, preferably 1 to 4 mol, relative to 1 mol of compound (VII).

The reaction of compound (VII) and compound (VIII) is usually carried out in the presence of a solvent, and the solvent includes nitrile solvents such as acetonitrile; methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and Alcohol solvents such as 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; Amide solvents such as N,N-dimethylformaldehyde and N-methylpyrrolidone include preferably nitrile solvents, alcohol solvents, and aromatic hydrocarbon solvents, and more preferably acetonitrile, methanol, and toluene. The usage-amount of a solvent is 1-100 mass parts normally with respect to 1 mass part of compound (VII).

The reaction temperature is usually 0 to 200°C, preferably 0 to 150°C. The reaction time is usually 0.5 to 36 hours.

After completion of the reaction, compound (II) can be taken out, for example, by mixing a solvent that hardly dissolves compound (II) with the resulting reaction mixture and filtering. According to needs, it can also be purified by further using a solvent for recrystallization or silica gel separation column chromatography.

Compound (VII) can be obtained by reacting a compound represented by formula (IX) (hereinafter, also referred to as compound (IX)) with a compound represented by formula (X) (hereinafter, also referred to as compound (X)) in a solvent And manufacture.

[式(IX)及式(X)中，R⁵至R⁹表示與上述相同意思。R¹⁰表示碳數1至4的烷基。]

[In formula (IX) and formula (X), R ⁵ to R ⁹ have the same meanings as above. R ¹⁰ represents an alkyl group having 1 to 4 carbon atoms. ]

The alkyl group having 1 to 4 carbon atoms represented by R ¹⁰ includes a methyl group, an ethyl group, a propyl group and a butyl group.

The compound (X) is usually used in an amount of 1 to 5 mol, preferably 1 to 3 mol, relative to 1 mol of the compound (IX).

Examples of the solvent include alcohol solvents such as methanol, and the amount of the solvent used is usually 1 to 200 parts by mass relative to 1 part by mass of the compound (IX).

The reaction temperature is usually -20 to 100°C, and the reaction time is usually 1 to 72 hours.

After completion of the reaction, for example, if necessary, the reaction mixture can be mixed with water, and then the compound (VII) can be taken out by filtration. Furthermore, after the completion of the reaction, for example, as required, the reaction mixture can be mixed with water, extracted with a water-insoluble organic solvent such as ethyl acetate, and the resulting organic layer can be concentrated, whereby the compound (VII) can also be taken out. . If necessary, it can also be purified by a method of recrystallization using a solvent or a silica gel separation column chromatography.

Compound (X) can be produced according to known methods such as the method described in J. Med. Chem. 2012, 55, 3398-3413.

The coloring composition of this invention may contain 2 or more types of compound (I). The compound (I) can be used as the colorant (A) together with a dye or pigment (colorant A1) other than the compound (I) as necessary.

The coloring composition of the present invention contains the compound (1), and at least one of the resin (B) and the solvent (E) so as to contain both the compound (1) and the resin (B) and the solvent (E). better.

<Solvent (E)>

Examples of the solvent (E) include ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvent containing -O- in the molecule and not containing -COO-), ether ester solvents ( Solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule, without -COO-), alcohol solvent (containing OH in the molecule, without -O-, -CO- and -COO- solvents), aromatic hydrocarbon solvents, amide solvents and dimethyl sulfoxide, etc.

As the ester solvent, methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, Butyl Propionate, Isopropyl Butyrate, Ethyl Butyrate, Butyrate, Methyl Pyruvate, Ethyl Pyruvate, Propyl Pyruvate, Methyl Acetate, Ethyl Acetate, Acetate Ring Hexanol esters and γ-butyrolactone, etc.

烷、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇甲基乙基醚、二乙二醇二丙基醚、二乙二醇二丁基醚、苯甲醚、苯乙醚及甲基苯甲醚等。 The ether solvent includes ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol Alcohol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-Methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-diol

Alkane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, benzyl ether, phenethyl ether and methyl anisole, etc.

The ether ester solvent includes methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate Ester, Ethyl 3-methoxypropionate, Methyl 3-ethoxypropionate, Ethyl 3-ethoxypropionate, Methyl 2-methoxypropionate, Ethyl 2-methoxypropionate ester, 2-methoxypropionate propyl, 2-ethoxypropionate methyl ester, 2-ethoxypropionate ethyl ester, 2-methoxy-2-methyl propionate methyl ester, 2-ethyl propionate Ethyl oxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, Propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol Methyl ether acetate, etc.

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

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

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

As an amide solvent, N,N- dimethylformamide, N,N- dimethylacetamide, N-methylpyrrolidone, etc. are mentioned.

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

The content of the solvent (E) is preferably from 40 to 99% by mass, more preferably from 50 to 95% by mass, with respect to the total amount of the coloring composition.

In the coloring composition of the present invention, the compound (I) is preferably dispersed in the solvent (E).

Compound (I) can be treated with rosin, surface treatment with derivatives of introducing acidic groups or basic groups, etc., grafting treatment of the surface of compound (I) with polymer compounds, etc., as required. Micronization treatment by sulfuric acid micronization method, etc., cleaning treatment by organic solvent for removing impurities, water, etc., removal treatment by ion exchange method of ionic impurities, etc. The particle size of the compound (I) is preferably approximately uniform. The compound (I) can be uniformly dispersed in the dispersion liquid by carrying out the dispersion treatment by making the compound (I) contain a dispersant.

The dispersing agent includes surfactants and the like, and may be any of cationic, anionic, nonionic, and amphoteric surfactants. Specifically, surfactants, such as polyester type, polyamine type, and acrylic type, etc. are mentioned. These dispersants may be used alone or in combination of two or more. When the dispersant is represented by a trade name, KP (Shin-Etsu Chemical Co., Ltd.), Floren (Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (Zeneca Co., Ltd.), EFKA (registered) Trademark) (BASF Co., Ltd.), Ajisper (registered trademark) (Ajinomoto Precision Technology Co., Ltd.), Disperbyk (registered trademark) (BYK Chemie Co., Ltd.), BYK (registered trademark) (BYK Chemie ( stock) system) etc.

When a dispersant is used, the usage amount of the dispersant (solid content) is preferably 300 parts by mass or less, more preferably 5 parts by mass or more and 100 parts by mass or less, relative to 100 parts by mass of the compound (I). When the usage-amount of a dispersing agent is the said range, there exists a tendency for the coloring composition of a more uniform dispersion state to be obtained.

The content rate of the compound (I) in the coloring composition is usually 0.1 to 60% by mass, preferably 0.5 to 50% by mass, and more preferably 1 to 40% by mass in the total amount of the coloring composition.

In the coloring composition, the content of the compound (I) is usually 1 mass % or more and 90 mass % or less, preferably 1 mass % or more and 80 mass % or less, more preferably 2 mass % or more with respect to the total amount of the solid content. 75% by mass or less.

<Resin (B)>

The resin (B) is preferably an alkali-soluble resin, more preferably a polymer having a structural unit derived from a monomer (a) (hereinafter also referred to as "(a)") selected from the group consisting of: At least one of the group consisting of saturated carboxylic acid and unsaturated carboxylic acid anhydride.

The resin (B) is more preferably a copolymer having a structural unit derived from a monomer (b) (hereinafter also referred to as "(b)"), which has a carbon number of 2, and other structural units A cyclic ether structure to 4 with an ethylenically unsaturated bond.

Other structural units include: derived from monomer (c) which can be copolymerized with monomer (a) (however, different from monomer (a) and monomer (b); hereinafter also referred to as "(c) ") structural units, structural units with ethylenically unsaturated bonds, etc.

(a) Examples include: acrylic acid, methacrylic acid, crotonic acid, and unsaturated monocarboxylic acids such as ortho, meta, and p-vinyl benzoic acid; maleic acid, fumaric acid, citraconic acid, and mesaconic acid , Iconic acid, 3-ethylene phthalic acid, 4-ethylene phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid , dimethyltetrahydrophthalic acid and unsaturated dicarboxylic acids such as 1,4-cyclohexene dicarboxylic 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, 5-carboxymethylbicyclo[2.2.1]hept-2-ene and 5-carboxyethyl Bicyclic unsaturated compounds containing carboxyl groups such as bicyclo[2.2.1]hept-2-ene; carboxylic acid anhydrides such as anhydrides of the above-mentioned unsaturated dicarboxylic acids other than fumaric acid and mesaconic acid; succinic acid mono[2-( Unsaturated mono[(methyl) carboxylic acids of divalent or higher polycarboxylic acids such as meth)acryloyloxyethyl]ester and mono[2-(meth)acryloyloxyethyl]phthalate ) Acryloyloxyalkyl] esters; such as unsaturated acrylates of α-(hydroxymethyl)acrylic acid containing hydroxyl and carboxyl groups in the same molecule.

Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferable from the viewpoint of copolymerization reactivity and the viewpoint of the solubility of the obtained resin to an aqueous alkali solution.

(b) refers to 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 oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated Bonded polymeric compounds. The (b) system is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

(b) Examples of monomers (b1) having an oxirane group and an ethylenically unsaturated bond (hereinafter also referred to as "(b1)"), and having an oxetanyl group and an ethylenically unsaturated bond include, for example. The monomer (b2) (hereinafter also referred to as "(b2)") and the monomer (b3) (hereinafter also referred to as "(b3)") having a tetrahydrofuran group and an ethylenically unsaturated bond, etc.

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

The (b1-1) is preferably a monomer having an glycidyl group and an ethylenically unsaturated bond. Specifically, (b1-1) includes glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, and β-ethyl epoxy (meth)acrylate. Propyl ester, glycidyl vinyl ether, vinyl benzyl glycidyl ether, α-methyl vinyl benzyl glycidyl ether, 2,3-bis(glycidoxymethyl) base) styrene, 2,4-bis(glycidoxymethyl)styrene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene oxymethyl)styrene, 2,3,4-para(glycidoxymethyl)styrene, 2,3,5-para(glycidoxymethyl)styrene, 2 , 3,6-para(glycidoxymethyl)styrene, 3,4,5-para(glycidoxymethyl)styrene and 2,4,6-para(glycidyloxymethyl)styrene oxymethyl) styrene, etc.

(b1-2) Examples include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (For example, Cyclomer (registered trademark) M100; manufactured by Daicel Corporation), the compound represented by the formula (BI), the compound represented by the formula (BII), and the like.

[In formula (BI) and formula (BII), 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 each independently represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S- or *-R ^c -NH-.

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

* indicates a bond with O. ]

The compound represented by the formula (BI) includes a compound represented by any one of the formula (BI-1) to the formula (BI-15), and the like, preferably the formula (BI-1) and the formula (BI-3) , compounds represented by formula (BI-5), formula (BI-7), formula (BI-9) and formula (BI-11) to formula (BI-15), more preferably, formula (BI-1) , compounds represented by formula (BI-7), formula (BI-9) and formula (BI-15).

The compound represented by the formula (BII) includes a compound represented by any one of the formula (BII-1) to the formula (BII-15), and the like, preferably the formula (BI1-1) and the formula (BI1-3) , compounds represented by formula (BII-5), formula (BII-7), formula (BII-9) and formula (BII-11) to formula (BII-15), more preferably, formula (BII-1) , compounds represented by formula (BII-7), formula (BII-9) and formula (BII-15).

The compound represented by formula (BI) and the compound represented by formula (BII) may be used independently, respectively, or the compound represented by formula (BI) and the compound represented by formula (BII) may be used together. When these compounds are used together, the content ratio of the compound represented by the formula (BI) and the compound represented by the formula (BII) is preferably 5:95 to 95:5 on a molar basis, more preferably 10:90 to 90:10, more preferably 20:80 to 80:20.

(c) For example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, second butyl methyl (meth)acrylate, third (meth)acrylate Butyl, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate , (meth)acrylate tricyclo[5.2.1.0 ^2,6 ] decane-8-yl ester, (meth)acrylate tricyclo[5.2.1.0 ^2,6 ] decan-9-yl ester, (methyl) acrylate ) Tricyclo[5.2.1.0 2,6 ]decen-8-yl acrylate, (meth)acrylate tricyclo[5.2.1.0 ^2,6 ] ^decen -9-yl ester, (meth)acrylate bicyclo Amyloxyethyl ester, Isobornyl (meth)acrylate, Adamantyl (meth)acrylate, Allyl (meth)acrylate, Propargyl (meth)acrylate, Benzene (meth)acrylate (meth)acrylates such as naphthyl (meth)acrylate and benzyl (meth)acrylate; 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate, etc. Hydroxy-containing (meth)acrylates; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itonate; 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-bis(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-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6 - Bicyclic unsaturated such as bis(tertiary butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene Compounds; N-Phenylmaleimide, N-Cyclohexylmaleimide, N-Benzylmaleimide, N-Succinimidyl-3-cis Butenediimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidino-3-maleimidopropionate and N-(9-acridinyl ) Dicarbonyl imide derivatives such as maleimide; vinyl-containing aromatic compounds such as styrene, α-methylstyrene, vinyltoluene and p-methoxystyrene; (methyl) Vinyl-containing nitriles such as acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl-containing amides such as (meth)acrylamide; esters such as vinyl acetate; Dienes such as pentadiene and 2,3-dimethyl-1,3-butadiene, etc.

Among these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, (meth)acrylate tricyclo[5.2.1.0 ^2,6 ]decan-8-yl ester, (Meth)acrylate tricyclo[5.2.1.0 ^2,6 ]decan-9-yl ester, (meth)acrylate tricyclo[5.2.1.0 ^2,6 ]decen-8-yl ester, (methyl) Tricyclo[5.2.1.0 ^2,6 ]decen-9-yl acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylcis-butyl Alkenediimide, bicyclo[2.2.1]hept-2-ene and benzyl (meth)acrylate are preferred.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth)acryloyl group. A resin having such a structural unit can be added to a polymer having a structural unit derived from (a) or (b) by adding a group reactive with the group (a) or (b) and ethylene. derived from monomers with unsaturated bonds.

Such a structural unit includes a structural unit in which glycidyl (meth)acrylate is added to a (meth)acrylic acid unit, and a (meth)acrylic acid 2 added to a maleic anhydride unit. - The structural unit of a hydroxyethyl ester, the structural unit etc. which added (meth)acrylic acid to a (meth)acrylic-acid glycidyl ester unit. In addition, when these structural units have a hydroxyl group, the structural unit which becomes a carboxylic acid anhydride can also be mentioned as a structural unit which has an ethylenically unsaturated bond.

A polymer having a structural unit derived from (a) can be produced, for example, by polymerizing a monomer constituting a structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator, solvent, etc. are not particularly limited, and those commonly used in the technical field can be used. Examples of the polymerization initiator include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or organic peroxides substances (benzyl peroxide, etc.), and the solvent should just be one that can dissolve each monomer.

In addition, the obtained polymer may use the solution after the reaction as it is, may use the concentrated or diluted solution, and may use what was made into a solid (powder) by methods, such as reprecipitation, and taken out.

A catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride and a cyclic ether (eg, ginseng (dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (eg, hydroquinone, etc.), etc., can also be used as required.

Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphosphonic anhydride, 4-vinylphosphonic anhydride, 3,4,5,6-tetrahydro Phosphophthalic anhydride, 1,2,3,6-tetrahydrophosphorophthalic anhydride, dimethyltetrahydrophosphorophthalic anhydride and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene Anhydride etc.

Specifically, resin (B) includes 3,4-epoxycyclohexylmethyl (meth)acrylic acid/(meth)acrylic acid copolymer, 3,4-epoxy (meth)acrylic acid Cyclohexyl[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/(meth)acrylate/(meth)acrylic acid copolymer, Glycidyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylate base) acrylic acid/N-cyclohexylmaleimide copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/ N-Cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate /(meth)acrylic acid/vinyltoluene copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/(meth)acrylic acid 2-Ethylhexyl ester copolymer, (meth)acrylate 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylate tricyclo[5.2.1.0 ^2,6 ] Decenyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)propenyloxymethyloxetane/(methyl) base) acrylic acid/styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer and Japanese Patent Laid-Open No. 9-106071, Japanese Patent Laid-Open No. 2004 -Resin and the like described in the respective gazettes of Gazette No. 29518 and Japanese Patent Laid-Open No. 2004-361455.

Among them, resin (B) is preferably a copolymer containing a structural unit derived from (a) and a structural unit derived from (b).

The resin (B) may be a combination of two or more kinds, and in this case, the resin (B) contains at least 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate selected from the group consisting of /(Meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/N-cyclohexylmaleic acid Imine/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyl Toluene copolymer, 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate The above is better.

The weight average molecular weight (Mw) in terms of refined polystyrene of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, still more preferably 5,000 to 30,000. The degree of dispersion [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.

The acid value (solid content conversion value) of the resin (B) is preferably 10 to 300 mg-KOH/g, more preferably 20 to 250 mg-KOH/g, still more preferably 30 to 200 mg-KOH/g. 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 determined by, for example, titration using an aqueous potassium hydroxide solution.

In the coloring composition, the content of the resin (B) is preferably 3 to 99% by mass, more preferably 5 to 99% by mass, and still more preferably 7 to 95% by mass relative to the total amount of the solid content.

The coloring composition of the present invention may contain a coloring agent (hereinafter, also referred to as a coloring agent (A1)) other than the compound (I). In the coloring agent (A1), one type or two or more types of colorants may be contained. The colorant (A1) preferably contains a yellow colorant, an orange colorant, or a red colorant.

<Colorant (A1)>

The colorant (A1) may be a dye or a pigment. As a dye, a known dye can be used, and examples thereof include those described in Color Index (published by The Society of Dyers and Colourists) and dyeing notes (color dyeing company). In addition, azo dyes, anthraquinone dyes, triphenylmethane dyes, dibenzopyran dyes, cyanine dyes, and the like are exemplified by chemical structures. These dyes may be used alone or in combination of two or more.

Specifically, dyes with the following color index (C.I.) numbers can be mentioned. 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. Active 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 52, 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, 12 8, 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.

As the pigment, known pigments can be used, and examples thereof include pigments classified as pigments in the color index (published by The Society of Dyers and Colourists). These pigments may be used alone or in combination of two or more.

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, 185, 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, 179, 180, 192 , 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273 and other red pigments; C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60 and other blues Color pigments; C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other purple pigments; C.I. Pigment Green 7, 36, 58, 59 and other green pigments.

The yellow colorant can also be selected from: the above-mentioned 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 and other yellow dyes; 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, 185 , 194, 214 and other yellow pigments.

Yellow colorants are preferably yellow dyes or yellow pigments, preferably yellow pigments, quinoneone yellow pigments, metallic yellow pigments, and isoindoline yellow pigments are more preferably C.I. Pigment Yellow 129, 138, 139 , 150, 185 are preferred.

Orange colorants can also be selected from the above: 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. Active Orange 16; C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107 and other orange dyes; C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments.

The orange colorant is preferably orange dye or orange pigment, preferably orange pigment, pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 is even better.

The red colorant may also be selected from the above: 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 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289 Iso red dyes; C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264 , 265, 266, 268, 269, 273 and other red pigments; among them.

Red colorants are preferably red dyes and red pigments, and include azo dyes, anthraquinone dyes, triphenylmethane dyes, dibenzopyran dyes, perylene dyes, azo pigments, diketopyrrolopyrrole pigments, Anthraquinone pigments, dibenzopyran pigments and perylene pigments are more preferred, and C.I. Acid Red 52, C.I. Pigment Red 144, 177, 179, 242, 254 and 269 are even more preferred.

In addition, as a yellow colorant, an orange colorant, or a red colorant, the dibenzopyran compound etc. which are described in Unexamined-Japanese-Patent No. 2013-235257 can also be used.

When the coloring composition of the present invention contains a coloring agent (A1), a coloring agent (A1)-containing liquid containing a coloring agent (A1) and a solvent (E) may be prepared in advance, and then a coloring composition may be prepared using the coloring agent (A1)-containing liquid. thing. When the colorant (A1) is not dissolved in the solvent (E), the colorant (A1)-containing liquid can be prepared by dispersing the colorant (A1) in the solvent (E) and mixing. The colorant (A1) containing liquid may contain a part or all of the solvent (E) contained in the coloring composition.

The coloring composition of the present invention is preferably produced by mixing the compound represented by the formula (I), the solvent (E), and the coloring agent (A1)-containing liquid containing the coloring agent (A1) and the solvent (E). The above-mentioned production method preferably mixes the compound represented by the formula (I) and the solvent (E) with a bead mill to prepare a coloring composition, and mixes the obtained coloring composition, a colorant containing the colorant (A1) and the solvent (E). A method of mixing a colorant (A1) containing liquid.

The coloring agent (A1) preferably contains at least one coloring agent selected from a yellow coloring agent, an orange coloring agent, and a red coloring agent.

The colorant (A1) can be treated with rosin, surface treatment using colorant derivatives introduced with acidic groups or basic groups, etc., and grafting treatment of the surface of the colorant (A1) with polymer compounds, etc. , Micronization treatment by sulfuric acid micronization method, etc., washing treatment by organic solvent or water for removing impurities, removal treatment by ion exchange method of ionic impurities, etc. The particle size of the colorant (A1) is preferably approximately uniform. The colorant (A1) is uniformly dispersed in the colorant (A1)-containing liquid by making the colorant (A1) contain a dispersant and performing dispersion treatment. The colorant (A1) may be dispersed separately, or may be mixed and dispersed.

The dispersing agent includes surfactants and the like, and may be any of cationic, anionic, nonionic, and amphoteric surfactants. Specifically, surfactants, such as polyester type, polyamine type, and acrylic type, etc. are mentioned. These dispersants may be used alone or in combination of two or more. Dispersants, when expressed by trade names, include KP (Shin-Etsu Chemical Co., Ltd.), Floren (Kyoeisha Chemical Co., Ltd.), Solspers (registered trademark) (Zeneca Co., Ltd.), EFKA ( Registered trademark) (BASF Co., Ltd.), Ajisper (registered trademark) (Ajinomoto Precision Technology Co., Ltd.), Disperbyk (registered trademark) (BYK Chemie Co., Ltd.), BYK (registered trademark) (BYK Chemie (stock) system), etc.

When a dispersant is used for preparing the colorant (A1)-containing liquid, the amount of the dispersant (solid part) used is preferably 300 parts by mass or less, more preferably 5 parts by mass relative to 100 parts by mass of the colorant (A1). More than 100 parts by mass or less. When the usage-amount of this dispersing agent is the said range, there exists a tendency for the coloring agent (A1) containing liquid of a more uniform dispersion state to be obtained.

The content rate of the colorant (A1) in the colorant (A1)-containing liquid is usually 0.1 to 60% by mass, preferably 0.5 to 50% by mass, more preferably 0.5 to 50% by mass in the total amount of the colorant (A1)-containing liquid 1 to 40% by mass.

In the colorant (A1)-containing liquid, the content of the colorant (A1) is usually 1 mass % or more and 90 mass % or less, preferably 1 mass % or more and 80 mass % or less, more preferably with respect to the total solid content. It is 2 mass % or more and 75 mass % or less.

The coloring composition of the present invention contains a resin (B), and a coloring composition is prepared using the coloring agent (A1)-containing liquid after preparing a coloring agent (A1)-containing liquid containing a coloring agent (A1) and a solvent (E) in advance The liquid containing the colorant (A1) may preliminarily contain a part or all of the resin (B) contained in the coloring composition, preferably a part thereof. Since the resin (B) is contained in advance, the dispersion stability of the liquid containing the colorant (A1) can be further improved.

The content of the resin (B) in the colorant (A1)-containing liquid is, for example, 1 to 500 parts by mass, preferably 5 to 200 parts by mass, and more preferably 10 to 100 parts by mass relative to 100 parts by mass of the colorant (A1). parts by mass.

In the coloring composition, the content rate of the coloring agent (A) in the total amount of the compound (I) and the coloring agent (A1) is usually 1 mass % or more and 90 mass % or less, preferably 1 mass % with respect to the total amount of the solid content. % or more and 80 mass % or less, more preferably 2 mass % or more and 75 mass % or less.

In the total amount of the colorant (A), the content of the compound (I) is usually 0.001 mass % or more, preferably 0.003 mass % or more, more preferably 0.005 mass % or more, usually 100 mass % or less, preferably 99.999 mass % or less, more preferably 99.997 mass % or less.

When the colorant (A1) is contained, the content of the colorant (A1) is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, and still more preferably 1 part by mass or more with respect to 100 parts by mass of the compound (I). , preferably 10,000 parts by mass or less, more preferably 5,000 parts by mass or less.

The colored curable composition of the present invention contains at least one of the compound (I), the resin (B), and the solvent (E), and the polymerizable compound (C).

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized by the active radical and/or acid generated by the polymerization initiator (D), such as a compound having a polymerizable ethylenically unsaturated bond, etc., with (methyl) Acrylate compounds are preferred.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, and 2-ethylhexyl carbitol acrylate. , 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc., as well as the above-mentioned monomers (a), monomers (b) and monomers (c).

Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, and neopentyl alcohol di(meth)acrylate. Acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate, etc.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. As such a polymerizable compound, for example, trimethylolpropane tri(meth)acrylate, neotaerythritol tri(meth)acrylate, neopentaerythritol tetra(meth)acrylate, dipivalethritol Alcohol Penta(meth)acrylate, Dipiveaerythritol Hexa(meth)acrylate, Trinetaerythritol Octa(meth)acrylate, Tripivalerythritol Hepta(meth)acrylate, Sixin Pentaerythritol ten (meth)acrylate, tetraneopentaerythritol nona (meth)acrylate, trimeric isocyanate (2-(meth)acryloyloxyethyl) ester, ethylene glycol modified Neotaerythritol Tetra(meth)acrylate, Ethylene Glycol-modified Dipivalerythritol Hex(meth)acrylate, Propylene Glycol-modified Neotaerythritol Tetra(meth)acrylate, Propylene Glycol Modified Di Neopentaerythritol hexa(meth)acrylate, caprolactone-modified neotaerythritol tetra(meth)acrylate, caprolactone-modified dipipentaerythritol hexa(meth)acrylate, etc., preferably Dipionaerythritol penta(meth)acrylate and dipeotaerythritol hexa(meth)acrylate are mentioned.

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

In the colorable curable composition, the content of the polymerizable compound (C) is preferably 1 to 65 mass %, more preferably 3 to 60 mass %, and still more preferably 5 to 55 mass % with respect to the total amount of the solid content. %.

The colored curable composition of the present invention may contain a polymerization initiator (D).

<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.

化合物及醯基氧化膦化合物等。 Examples of the polymerization initiator (D) include O-acyl oxime compounds, alkylphenone compounds, biimidazole compounds, tris

Compounds and acyl phosphine oxide compounds, etc.

Examples of O-benzyl oxime compounds include N-benzyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzyloxy-1 base-1-(4-phenylthiophenyl)octan-1-one-2-imine, N-benzyloxy-1-(4-phenylthiophenyl)-3- Cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclopentylpropan-1-one-2-imine, N-Acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetyloxy-1-[9-ethyl- 6-(2-Methylbenzyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2- Methyl-4-(3,3-dimethyl-2,4-dioxolanemethyloxy)benzyl)-9H-carbazol-3-yl]ethane-1-idene Amine, N-Acetyloxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-idene Amine and N-benzyloxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1 - Keto-2-imine, etc. Furthermore, as the O-acyl oxime compound, commercially available products such as Irgacure OXE01 and OXE02 (all of which are made by BASF Corporation) and N-1919 (made by ADEKA Corporation) can also be used. Wherein, the O-acyl oxime compound is selected from N-benzyloxy-1-(4-phenylthiophenyl) butane-1-one-2-imine, N-benzyl Acyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-benzyloxy-1-(4-phenylsulfanylphenyl) One of the group consisting of -3-cyclopentylpropan-1-keto-2-imine is preferably, N-benzyloxy-1-(4-phenylthiophenyl)octane Alkan-1-one-2-imine is more preferred.

Examples of the alkylphenone compound include: 2-methyl-2-morpholino-1-(4-methylthiophenyl)propan-1-one, 2-dimethylamino-1-(4 -Morpholinylphenyl)-2-benzylbutan-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4- (4-morpholinyl)phenyl]butan-1-one and the like. As the alkyl phenone compound, commercially available products such as Irgacure 369, 907, and 379 (all of them are manufactured by BASF Corporation) can also be used.

Examples of the phenalkyl ketone compound include: 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy) Phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl) propan-1-one, α, Alpha-diethoxyacetophenone and benzyl dimethyl ketal.

Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl) Phenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2'-bis( 2-Chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(alkane) oxyphenyl)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 Publication No. 62-174204, etc. ) and an imidazole compound in which the phenyl group at the 4,4', 5,5'-position is substituted with an alkoxycarbonyl group (for example, see Japanese Patent Laid-Open No. 7-10913, etc.) and the like.

化合物可舉出：2,4-雙(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-三

、2,4-雙(三氯甲基)-6-(4-甲氧基萘基)-1,3,5-三

、2,4-雙(三氯甲基)-6-胡椒基-1,3,5-三

、2,4-雙(三氯甲基)-6-(4-甲氧基苯乙烯基)-1,3,5-三

、2,4-雙(三氯甲基)-6-[2-(5-甲基呋喃-2-基)乙烯基]-1,3,5-三

、2,4-雙(三氯甲基)-6-[2-(呋喃-2-基)乙烯基]-1,3,5-三

、2,4-雙(三氯甲基)-6-[2-(4-二乙基胺基-2-甲基苯基)乙烯基]-1,3,5-三

及2,4-雙(三氯甲基)-6-[2-(3,4-二甲氧基苯基)乙烯基]-1,3,5-三

等。 three

Compounds include: 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-tris

, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-tris

, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-tri

, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-tri

, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-tri

, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-tri

, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-tri

and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-tri

Wait.

As an acyl phosphine oxide compound, 2, 4, 6- trimethylbenzyl diphenyl phosphine oxide etc. are mentioned.

In addition, the polymerization initiator (D) includes benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate , 4-phenylbenzophenone, 4-benzyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)di Benzophenone compounds such as benzophenone and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2 - Chloracridone, benzophenone, methyl phenylglyoxylate and titanocene compounds, etc.

These compounds are preferably used in combination with a polymerization initiator (D1) (especially amines) described later.

化合物、醯基氧化膦化合物、O-醯基肟化合物及聯咪唑化合物所構成群組中的至少一種之聚合起始劑，更佳為含有O-醯基肟化合物的聚合起始劑。 The polymerization initiator (D) preferably contains a compound selected from the group consisting of phenalkyl ketone compounds, tris

The polymerization initiator of at least one of the group consisting of the compound, the acylphosphine oxide compound, the O-acyl oxime compound and the biimidazole compound is more preferably a polymerization initiator containing an O-acyl oxime compound.

The content of the polymerization initiator (D) is preferably from 0.001 to 40 mass %, more preferably from 0.01 to 30 mass %, in the total amount of the solid content in the colored curable composition.

The colorable curable composition of the present invention may contain a polymerization initiator (D1).

<Polymerization Initiating Auxiliary (D1)>

The polymerization initiation adjuvant (D1) is a compound used for accelerating the polymerization of the polymerizable compound whose polymerization is initiated by the polymerization initiator, or a sensitizer. When a polymerization initiator (D1) is contained, it can usually be used in combination with a polymerization initiator (D).

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

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, and 4-dimethylamine Isoamyl benzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4' -Bis(dimethylamino)benzophenone (commonly known as Michler's Ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis (Ethylmethylamino) benzophenone etc., Preferably, 4,4'-bis (diethylamino) benzophenone is mentioned. In addition, commercial products, such as EAB-F (made by Hodogaya Chemical Industry Co., Ltd.), can also be used as the amine compound.

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

The thioxanthone compound includes 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichlorothioxanthone, and 1-chlorothioxanthone -4-Propoxythioxanthone, etc.

Carboxylic acid compounds include: phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxy phenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid , N-naphthylglycine and naphthyloxyacetic acid, etc.

When these polymerization initiators (D1) are used, the content rate in the total amount of the solid content in the colored curable composition is preferably 0.001 to 30 mass %, more preferably 0.01 to 20 mass %.

The coloring composition of this invention may contain a leveling agent (F) and an antioxidant.

<Leveler (F)>

The leveling agent (F) includes a polysiloxane-based surfactant, a fluorine-based surfactant, and a polysiloxane-based surfactant having a fluorine atom. These surfactants may have a polymerizable group in the side chain.

The polysiloxane-based surfactant includes a surfactant having a siloxane bond in the molecule, and the like. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (all are trade names, Toray Dow Corning (stock) ); KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.); TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (Momentive Performance Materials company), etc.

As a fluorine-type surfactant, the surfactant etc. which have a fluorocarbon chain in a molecule|numerator are mentioned. Specifically, Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Co., Ltd.); Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS-718-K (manufactured by DIC Corporation); EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.); Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemicals, Inc.), etc.

The polysiloxane-based surfactant having a fluorine atom includes a surfactant having a siloxane bond and a fluorocarbon chain in the molecule, and the like. Specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, and Megafac F443 (manufactured by DIC Corporation), etc. are mentioned.

When the leveling agent (F) is contained, the content rate relative to the total amount of the coloring composition is usually 0.005 mass % or more and 1 mass % or less, preferably 0.001 mass % or more and 0.5 mass % or less, more preferably 0.001 mass % It is 0.2 mass % or more, More preferably, it is 0.002 mass % or more and 0.1 mass % or less, Especially preferably, it is 0.005 mass % or more and 0.1 mass % or less. When the content of the leveling agent (F) is within the aforementioned range, the flatness of the color filter can be made favorable.

<Antioxidant>

From the viewpoint of improving the heat resistance and light resistance of the colorant, antioxidants are preferably used alone or in combination of two or more. The antioxidant is not particularly limited as long as it is an antioxidant generally used industrially, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant, and the like can be used.

-2,4,6(1H,3H,5H)-三酮，BASF(股)製)、Irganox 3790(Irganox 3790：1,3,5-參((4-第三丁基-3-羥基-2,6-二甲苯基)甲基)-1,3,5-三

-2,4,6(1H,3H,5H)-三酮，BASF(股)製)、Irganox 1035(Irganox 1035：硫代二乙烯基雙[3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯]，BASF(股)製)、Irganox 1135(Irganox 1135：苯丙烷酸，3,5-雙(1,1-二甲基乙基)-4-羥基，C7-C9側鏈烷酯，BASF(股)製)、Irganox 1520L(Irganox 1520L：4,6-雙(辛基硫甲基)-鄰甲酚，BASF(股)製)、Irganox 3125(Irganox 3125，BASF(股)製)、Irganox 565(Irganox 565：2,4-雙(正-辛基硫基)-6-(4-羥基3’,5’-二-第三丁基苯胺基)-1,3,5-三

，BASF(股)製)、ADK STAB AO-80(ADK STAB AO-80：3,9-雙(2-(3-(3-第三丁基-4-羥基-5-甲基苯基)丙醯氧基)-1,1-二甲基乙基)-2,4,8,10-四氧雜螺(5,5)十一烷，ADEKA(株)製)、Sumilizer BHT(住友化學(股)製)、Sumilizer GA-80(住友化學(股)製)、Sumilizer GS(住友化學(股)製)、Cyanox 1790(scitec(股)製)及維生素E(Eisai(股)製)等。 Examples of the aforementioned phenolic antioxidant include Irganox 1010 (Irganox 1010: neopentaerythritol tetra[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], BASF (stock) manufactured by BASF), Irganox 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, manufactured by BASF (stock)), Irganox 1330 (Irganox 1330 : 3,3',3",5,5',5"-hexa-tert-butyl-a,a',a"-(mesitylene-2,4,6-triyl)tri-paramethyl Phenol, manufactured by BASF (stock), Irganox 3114 (Irganox 3114: 1,3,5-Sham(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-tris

-2,4,6(1H,3H,5H)-trione, manufactured by BASF (stock), Irganox 3790 (Irganox 3790: 1,3,5-sam((4-tert-butyl-3-hydroxy- 2,6-xylyl)methyl)-1,3,5-tris

-2,4,6(1H,3H,5H)-trione, manufactured by BASF (stock), Irganox 1035 (Irganox 1035: thiodivinylbis[3-(3,5-di-tertbutyl) -4-hydroxyphenyl)propionate], BASF (stock), Irganox 1135 (Irganox 1135: phenylpropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxyl, C7-C9 side chain alkyl ester, manufactured by BASF (stock), Irganox 1520L (Irganox 1520L: 4,6-bis(octylthiomethyl)-o-cresol, manufactured by BASF (stock)), Irganox 3125 (Irganox 3125 , BASF (stock)), Irganox 565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy 3',5'-di-tert-butylanilino)- 1,3,5-Three

, BASF (stock) system), ADK STAB AO-80 (ADK STAB AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl) Propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro(5,5)undecane, manufactured by ADEKA Co., Ltd.), Sumilizer BHT (Sumitomo Chemical) (Co., Ltd.), Sumilizer GA-80 (Sumitomo Chemical Co., Ltd.), Sumilizer GS (Sumitomo Chemical Co., Ltd.), Cyanox 1790 (Scitec Co., Ltd.), and vitamin E (Eisai Co., Ltd.), etc. .

Examples of the aforementioned phosphorus-based antioxidants include Irgafos168 (Irgafos168: Ref. (2,4-di-tert-butylphenyl)phosphite, manufactured by BASF Corporation), Irgafos12 (Irgafos12: Ref. [2-[[2 ,4,8,10-Tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphine-6-yl]oxy]ethyl]amine, BASF (stock), Irgafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl phosphorous acid, manufactured by BASF (stock)), ADK STAB 329K (ADEKA), ADK STAB PEP36 (ADEKA), ADK STAB PEP-8 (ADEKA), Sandstab P-EPQ (Clariant), Weston 618 (GE) (manufactured by GE), Weston 619G (manufactured by GE), Ultranox 626 (manufactured by GE), and Sumilizer GP (Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propane] Oxy]-2,4,8,10-tetra-tert-butylbenzo[d,f][1.3.2]dioxaphosphine) (manufactured by Sumitomo Chemical Co., Ltd.) and the like.

Examples of the aforementioned sulfur-based antioxidant include dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, bismyristate, and distearate, and tetra[methylene(3-dodecane) [beta]-alkylthiol propionate compounds of polyhydric alcohols such as thio) propionate] methane, and the like.

<Other ingredients>

The coloring composition of the present invention may also contain additives known in the technical field, such as fillers, other polymer compounds, adhesion promoters, light stabilizers, and chain transfer agents, as required.

The adhesion promoters include, for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinylsins(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane Silane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxy ring Hexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-sulfur Alcohol propyltrimethoxysilane, 3-thiopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyl Dimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxy Silane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-amine propylpropyl triethoxysilane, etc.

<Color filter>

A color filter can be formed from the coloring composition or the coloring curable composition of the present invention. As a method of forming a colored pattern, a photolithography method, an ink jet method, a printing method, etc. are mentioned, and a photolithography method is preferable. The photolithography method is a method of applying the coloring curable composition to a substrate, drying it to form a coloring curable composition layer, exposing the coloring curable composition layer through a mask, and developing the coloring curable composition layer. In the photolithography method, the colored curable composition preferably contains a polymerization initiator (D). In the photolithography method, a colored coating film belonging to the cured product of the colored curable composition layer described above can be formed by not using a mask and/or developing during exposure. The colored pattern or colored coating film thus formed can be used as the color filter of the present invention.

The film thickness of the produced color filter is not particularly limited, and can be appropriately adjusted according to the purpose or use, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, more preferably 0.5 to 6 μm.

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

The formation of each color pixel by photolithography can be carried out using known or commonly used apparatus or conditions. For example, it can be produced as follows.

First, a colored curable composition is applied on a substrate, and volatile components such as a solvent are removed and dried by heat drying (prebaking) and/or drying under reduced pressure to obtain a smooth colored curable composition layer.

The coating method includes a spin coating method, a slit coating method, a slit and spin coating method, and the like.

Next, the colored curable composition layer is exposed through a photomask for forming the intended colored pattern. In order to uniformly irradiate the entire exposure surface with parallel light, or to align the correct position of the mask and the substrate on which the colored curable composition layer is formed, exposure apparatuses such as a mask alignment exposure machine and a stepper are used. better.

A colored pattern is formed on the substrate by contacting the exposed colored curable composition layer with a developing solution and developing the image. By developing, the unexposed part of the colored curable composition layer is dissolved in the developing solution and removed.

The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium oxide.

The development method may be any of a liquid coating method, a dipping method, and a spray method. Furthermore, the substrate can be inclined at any angle during development.

The developed substrate is preferably washed with water.

Moreover, it is preferable to perform post-baking on the obtained coloring pattern.

The aforementioned color filters can be used as color filters used in display devices (eg, liquid crystal display devices, organic EL display devices, electronic paper, etc.) and solid-state imaging elements, and are particularly useful as color filters used in liquid crystal display devices. .

[Example]

Hereinafter, the present invention will be described in more detail by way of examples. However, the present invention is not limited to the scope of the following examples. Of course, the present invention can be implemented by adding appropriate changes within the scope suitable for the gist of the foregoing and later. Included in the technical scope of the present invention.

Unless otherwise specified, "%" and "parts" in the examples represent mass % and mass parts.

In the following synthesis example, the structure of the compound was confirmed by mass spectrometry (LC; 1200 type by Agilent, MASS; LC/MSD6130 type by Agilent).

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

Device: HLC-8120GPC (made by TOSOH)

Separation column: TSK-GELG2000HXL

Separation column temperature: 40℃

Solvent: Tetrahydrofuran

Flow rate: 1.0mL/min

Solid content concentration of analysis sample: 0.001 to 0.01 mass %

Injection volume: 50 μL

Detector: RI

Standard material for calibration: TSK standard polystyrene (TSK STANDARD POLYSTYRENE) F-40, F-4, F-288, A-2500, A-500 (manufactured by TOSOH Co., Ltd.)

The ratio (Mw/Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the obtained polystyrene conversion was made into the degree of dispersion.

Example 1

Under a nitrogen atmosphere, 24.0 parts of m-aminoanisole, 99.7 parts of 4-iodo-m-xylene, 117 parts of potassium carbonate, 27.3 parts of copper powder, 4.64 parts of 18-crown-6 (18-crown-6) and 511 parts of o-dichlorobenzene were mixed, and the mixture was stirred at 175° C. for 19 hours. Then, 35.1 parts of potassium carbonate, 8.19 parts of copper powder, 1.39 parts of 18-crown-6, and 22.0 parts of o-dichlorobenzene were added, and the mixture was stirred at 175° C. for 17 hours. The above mixture was left to cool to room temperature, and then filtered. To the filtrate was added 450 parts of ethyl acetate, and washed three times with 450 parts of 2N hydrochloric acid and three times with 470 parts of an 18 wt % aqueous sodium chloride solution. The resulting ethyl acetate solution was dried over magnesium sulfate and filtered. After the filtrate was distilled off with a rotary evaporator, the obtained residue was purified with a separation column chromatography to obtain 64.1 parts of the compound represented by the formula (pt2-2).

<Identification of the compound represented by the formula (pt2-2)>

(Mass Analysis) Ionization Mode=ESI+: m/z=[M+H] ⁺ 332 Correct Mass: 331

31.7 parts of the compound represented by formula (pt2-2) and 190 parts of dehydrated dichloromethane were mixed at 0°C in a nitrogen atmosphere. Next, 199 parts of a 17% by weight boron tribromide dichloromethane solution was added, followed by stirring for 1 hour. Then, it was stirred at room temperature for 12 hours. After adding this mixture to 1,100 parts of ice water, 740 parts of chloroform was added, and the chloroform layer was extracted. The obtained chloroform solution was washed with 470 parts of an 18% by weight aqueous sodium chloride solution, dried over magnesium sulfate, and filtered. After the filtrate was distilled off with a rotary evaporator, the obtained residue was purified with a separation column chromatography to obtain 30.0 parts of the compound represented by the formula (pt3-2).

<Identification of the compound represented by the formula (pt3-2)>

(Mass Analysis) Ionization Mode=ESI+: m/z=[M+H] ⁺ 318 Correct Mass: 317

7.46 parts of the compound represented by formula (pt3-2) and 14.4 parts of N,N-dimethylformamide were mixed at 5 to 10° C. under a nitrogen atmosphere. While maintaining the temperature of this mixture at 5 to 10°C, 7.21 parts of phosphoric acid chloride was added. Then, the mixture was stirred at 10°C or lower for 1 hour, at room temperature for 1 hour, and at 80°C for 1 hour. After the reaction mixture was left to cool to room temperature, 100 parts of ice water was added, and the mixture was neutralized with a 48% aqueous sodium hydroxide solution. To this mixture was added 180 parts of ethyl acetate, followed by diatomaceous earth and stirring. The mixture was filtered and the ethyl acetate layer was extracted. The ethyl acetate layer was dried over magnesium sulfate and filtered. After the solvent was distilled off from the filtrate with a rotary evaporator, the obtained residue was purified with a separation column chromatography to obtain 6.26 parts of the compound represented by the formula (pt4-2).

<Identification of the compound represented by the formula (pt4-2)>

(Mass Analysis) Ionization Mode=ESI+: m/z=[M+H] ⁺ 346 Correct Mass: 345

10.1 parts of the compound represented by the formula (pt4-2), 6.36 parts of the compound represented by the formula (pt1) synthesized by the method described in J.Org.Chem. 2002, 67, 5767, 0.600 parts of piperidine and 112 parts of toluene were mixed , and stirred at 105 °C for 24 hours. After the mixture was allowed to cool to room temperature, the solvent was distilled off with a rotary evaporator, and the obtained residue was purified with a separation column chromatography to obtain 0.867 parts of the compound represented by the formula (II-2).

<Identification of the compound represented by the formula (II-2)>

(Mass Analysis) Ionization Mode=ESI+: m/z=[M+H] ⁺ 503 Correct Mass: 502

20.1 parts of the compound represented by formula (II-2) and 1030 parts of toluene were mixed and stirred at 87°C. To this mixture was added 9.85 parts of methyl trifluoromethanesulfonate. The mixture was stirred at 87°C for 3 hours. The mixture was stirred at 10°C. After the solvent was distilled off from this mixture with a rotary evaporator, the obtained residue was purified with a separation column chromatography to obtain 2.29 parts of the compound represented by the formula (I-73).

<Identification of the compound represented by the formula (I-73)>

(Mass Analysis) Ionization mode=ESI+: m/z=517[M-CF ₃ SO ₃ ] ⁺ correct mass: 666

5.00 parts of the compound represented by formula (I-73) and 1,500 parts of methanol were mixed. To this mixture was added a mixture of 7.99 parts of phosphotungstic acid hydrate (manufactured by Japan Sigma Aldrich Co., Ltd.) and 79.9 parts of methanol. The mixture was filtered, and the obtained residue was washed with 500 parts of methanol. The residue was dried under reduced pressure at 60°C to obtain 9.30 parts of the compound represented by the formula (I-74).

<Identification of the compound represented by the formula (I-74)>

(mass analysis) ionization mode = ESI+: m/z=517[(MO ₄₀ PW ₁₂ )/3] ⁺ correct mass: 4430

Example 2

In Example 1, the same procedure as in Example 1 was carried out except that the compound represented by formula (pt2-2) was replaced by the compound represented by formula (pt2-3) synthesized by the method described in US Patent Publication US 2007/0073086 A1. operation to obtain the compound represented by the formula (pt3-3), the compound represented by the formula (pt4-3), the compound represented by the formula (II-3), and the compound represented by the formula (I-23).

<Identification of the compound represented by the formula (pt3-3)>

(Mass Analysis) Ionization Mode=ESI+: m/z=[M+H] ⁺ 228 Correct Mass: 227

<Identification of the compound represented by the formula (pt4-3)>

(Mass Analysis) Ionization Mode=ESI+: m/z=[M+H] ⁺ 256 Correct Mass: 255

<Identification of the compound represented by the formula (II-3)>

(Mass Analysis) Ionization Mode=ESI+: m/z=[M+H] ⁺ 413 Correct Mass: 412

<Identification of the compound represented by the formula (I-23)>

(Mass Analysis) Ionization Mode=ESI+: m/z=427 [M-CF ₃ SO ₃ ] ⁺ correct mass: 592

5.00 parts of the compound represented by formula (I-23) and 1,500 parts of methanol were mixed. To this mixture was added a mixture of 9.24 parts of phosphotungstic acid hydrate (manufactured by Nippon Sigma Aldrich Co., Ltd.) and 92.4 parts of methanol. The mixture was filtered, and the obtained residue was washed with 500 parts of methanol. The residue was dried under reduced pressure at 60°C to obtain 9.70 parts of the compound represented by the formula (I-33).

<Identification of the compound represented by the formula (I-33)>

(Mass Analysis) Ionization mode=ESI+: m/z=427[MO ₄₀ PW ₁₂ /3] ⁺ correct mass: 4160

Synthesis Example 1

14.4 parts of coumarin 6 (manufactured by Tokyo Chemical Industry Co., Ltd.) and 737 parts of toluene were mixed and stirred at 87°C. To this mixture was added 10.1 parts of methyl trifluoromethanesulfonate. The mixture was stirred at 87°C for 3 hours. The mixture was stirred at 10°C. This mixture was filtered, and the obtained residue was washed 6 times with 433 parts of toluene. The residue was dried under reduced pressure at 60°C to obtain 20.8 parts of the compound represented by the formula (X-1).

<Identification of the compound represented by the formula (X-1)>

(Mass Analysis) Ionization Mode=ESI+: m/z=365 [M-CF ₃ SO ₃ ] ⁺ correct mass: 514

[Evaluation of heat resistance]

Differential scanning calorimetry of the compounds obtained in Example 1, Example 2, and Synthesis Example 1 was performed using a simultaneous differential thermogravimetric measuring apparatus (TG/DTA6200 manufactured by SII Nanotechnology). The amount of sample used in one measurement was 5 mg. The measurement temperature was initially started from 45°C, the temperature was increased at a rate of 5°C per minute, and the temperature was measured to 550°C. The temperature T ₅ (under nitrogen) at which the weight reduction rate in a nitrogen atmosphere becomes 5% was obtained. The results are shown in Table 8.

As can be seen from the results in Table 8, the compound of the present invention has high heat resistance.

Synthesis Example 2

An appropriate amount of nitrogen was poured into a flask equipped with a reflux cooler, a dropping funnel, and a stirrer to replace it with a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C while stirring. Next, 38 parts of acrylic acid, 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate, and 3,4-epoxy tricyclo[5.2.1.0 ^2,6 acrylate A mixed solution of 289 parts of a mixture of ] decane-9-yl ester and 125 parts of propylene glycol monomethyl ether acetate was dropped over 5 hours. On the other hand, a mixed solution in which 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) was dissolved in 235 parts of propylene glycol monomethyl ether acetate was dropped over 6 hours. After the dropping was completed, the solution was kept at the same temperature for 4 hours, and then cooled to room temperature to obtain a solution of the copolymer (resin B1) with a solid content of 35.0%. The weight-average molecular weight (Mw) of the obtained resin B1 was 880, the degree of dispersion was 2.1, and the acid value of the solution was 28 mg-KOH/g.

Synthesis Example 3

An appropriate amount of nitrogen was poured into a flask equipped with a reflux cooler, a dropping funnel, and a stirrer to replace it with a nitrogen atmosphere, 257 parts of ethyl lactate was added, and the mixture was heated to 75°C while stirring. Next, 81 parts of methacrylic acid, 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate, and 3,4-epoxy tricyclo[5.2.1.0 ² acrylate ^,6 ] The mixed solution of 369 parts of decane-9-yl esters and 25 parts of ethyl lactate was dripped over 5 hours. On the other hand, a mixed solution in which 11 parts of 2,2-azobis(2,4-dimethylvaleronitrile) was dissolved in 162 parts of ethyl lactate was dropped over 5 hours. After completion of the dropping, after maintaining at the same temperature for 5 hours, 95 parts of ethyl lactate was added and cooled to room temperature to obtain a solution of the copolymer (resin B2) with a solid content of 47.7%. The weight average molecular weight (Mw) of the obtained resin B2 was 8,100, the degree of dispersion was 1.9, and the acid value of the solution was 53 mg-KOH/g.

Synthesis Example 4

An appropriate amount of nitrogen was poured into a flask equipped with a reflux cooler, a dropping funnel, and a stirrer instead of a nitrogen atmosphere, 371 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 85°C while stirring. Next, 54 parts of acrylic acid, 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate, and 3,4-epoxy tricyclo[5.2.1.0 ^2,6 acrylate ] A mixed solution of 225 parts of a mixture of decane-9-yl esters, 81 parts of vinyltoluene (isomer mixture), and 80 parts of propylene glycol monomethyl ether acetate was dropped over 4 hours. On the other hand, a mixed solution in which 30 parts of 2,2-azobis(2,4-dimethylvaleronitrile) was dissolved in 160 parts of propylene glycol monomethyl ether acetate was dropped over 5 hours. After the drop of the initiator solution was completed, the solution was kept at the same temperature for 4 hours, and then cooled to room temperature to obtain a solution of the copolymer (resin B3) with a solid content of 37.5%.

The weight-average molecular weight (Mw) of the obtained resin B3 was 10,600, the degree of dispersion was 2.01, and the acid value of the solution was 43 mg-KOH/g.

Synthesis Example 5

An appropriate amount of nitrogen was poured into a flask equipped with a reflux cooler, a dropping funnel, and a stirrer to replace it with a nitrogen atmosphere, 54 parts of ethyl lactate and 141 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 85°C while stirring. Next, 35 parts of acrylic acid, 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate, and 3,4-epoxy tricyclo[5.2.1.0 ^2,6 acrylate ] A mixed solution of 23 parts of decane-9-yl ester mixture, 161 parts of cyclohexylmaleimide, 12 parts of 2-hydroxyethyl methyl acrylate and 493 parts of propylene glycol monomethyl ether acetate 5 hours to drop. On the other hand, a mixed solution in which 3 parts of 2,2-azobis(2,4-dimethylvaleronitrile) was dissolved in 78 parts of propylene glycol monomethyl ether acetate was dropped over 6 hours. After the dropping was completed, the solution was kept at the same temperature for 4 hours, and then cooled to room temperature to obtain a solution of the copolymer (resin B4) with a solid content of 24.4%. The weight average molecular weight (Mw) of the obtained resin B4 was 8,400, the degree of dispersion was 2.1, and the acid value of the solution was 26 mg-KOH/g.

[Film thickness measurement]

The film thickness was measured by DEKTAK3; Nippon Vacuum Technology Co., Ltd.

[Preparation of resin composition for sublimation test (SJS)]

The following components were mixed to obtain a resin composition (SJS) for a sublimation test. Resin: methacrylic acid/benzyl methacrylate (molar ratio: 30/70) copolymer (manufactured by Taoka Chemical Industry Co., Ltd., weight average molecular weight (Mw) 10,700, acid value 70 mg-KOH/g) 33.8% 40 parts of propylene glycol monomethyl ether acetate solution; polymerizable compound: dipivaloerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 5.8 parts; polymerization initiator: N-benzene Methoxy-1-(4-phenylthiophenyl)octan-1-one-2-amine (Irgacure (registered trademark) OXE01; manufactured by BASF, Japan) 0.58 part; Leveling agent: polyether modified Quality polysiloxane oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.) 0.010 parts; solvent: 47 parts of propylene glycol monomethyl ether; solvent: 6.8 parts of propylene glycol monomethyl ether acetate

[Formation of resin coating film (SJSM) for sublimation test]

The resin composition for sublimation test (SJS) obtained above was applied to a 2-inch-square glass substrate (EagleXG; manufactured by Corning) by a spin coating method, and the volatile components were volatilized at 100° C. for 3 minutes. . After cooling, an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.) was used to irradiate with an exposure amount of 150 mJ/cm ² (365 nm standard) in an atmospheric environment. It heated in an oven at 220 degreeC for 2 hours, and formed the resin coating film (SJSM) (film thickness 2.2 micrometers) for a sublimation test.

Example 3

Colorant (A): 18 parts of the compound represented by formula (I-73); Resin (B): 470 parts of resin B1 solution; Solvent (E): 6.2 parts of propylene glycol monomethyl ether acetate; Solvent (E): 510 parts of N-methyl-2-pyrrolidone; and 0.063 part of surfactant: polyether-modified polysiloxane oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) were mixed to obtain Coloring Composition 1.

Example 4

Colorant (A): 18 parts of the compound represented by formula (I-23); Resin (B): 470 parts of resin B1 solution; Solvent (E): 6.2 parts of propylene glycol monomethyl ether acetate; Solvent (E): 510 parts of N-methyl-2-pyrrolidone; and 0.063 part of surfactant: polyether-modified polysiloxane oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) were mixed to obtain Colored Composition 2.

Example 5

Colorant (A): 36 parts of the compound represented by formula (I-74); Resin (B): 410 parts of resin B1 solution; Solvent (E): 6.2 parts of propylene glycol monomethyl ether acetate; Solvent (E): 540 parts of N-methyl-2-pyrrolidone; and 0.063 part of surfactant: polyether-modified polysiloxane oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) were mixed to obtain Colored Composition 3.

Example 6

Colorant (A): 36 parts of the compound represented by formula (I-33); Resin (B): 410 parts of resin B1 solution; Solvent (E): 6.2 parts of propylene glycol monomethyl ether acetate; Solvent (E): 540 parts of N-methyl-2-pyrrolidone; and 0.063 part of surfactant: polyether-modified polysiloxane oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) were mixed to obtain Colored Composition 4.

Example 7

Colorant (A): compound represented by formula (I-74): 10 parts; resin (B): 97 parts of resin B2 solution; solvent (E): 180 parts of N-methyl-2-pyrrolidone; solvent (E): 26 parts of 4-hydroxy-4-methyl-2-pentanone; solvent (E): 2.0 parts of propylene glycol monomethyl ether acetate; and surfactant: polyether modified polysiloxane oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.) 0.020 part was mixed to obtain Colored Composition 5.

Example 8

In Example 7, except having replaced the compound represented by formula (I-74) with the compound represented by formula (I-33), the same operation as Example 7 was performed, and the coloring composition 6 was obtained.

Example 9

Colorant (A): 10 parts of the compound represented by formula (I-74), 10 parts of dispersant (BYK-LPN21324; manufactured by Japan BYK Chemical Co., Ltd.), resin (B): 11 parts of resin B1 solution, and solvent (E): Mix 160 parts of propylene glycol monomethyl ether acetate, and disperse 100 parts of the coloring composition of the compound represented by formula (I-74) using a bead mill; Resin (B): 55 parts of resin B1 solution; Solvent (E): 3.6 parts of propylene glycol monomethyl ether acetate; and 0.010 part of surfactant: polyether-modified polysiloxane oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) were mixed to obtain Coloring Composition 7.

Example 10

Colorant (A): 10 parts of the compound represented by formula (I-33), 10 parts of dispersant (BYK--LPN21324; Japan BYK Chemical Co., Ltd.), resin (B): 11 parts of resin B3 solution, and Solvent (E): Mix 170 parts of propylene glycol monomethyl ether acetate, and disperse 100 parts of the coloring composition with the compound represented by formula (I-33) using a bead mill; Resin (B): 20 parts of resin B1 solution; Solvent (E): 3.6 parts of propylene glycol monomethyl ether acetate; and surfactant: 0.010 part of polyether-modified polysiloxane oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) were mixed to obtain Coloring Composition 8 .

Comparative Example 1

Colorant (A): 6 11 parts of coumarin; resin (B): 350 parts of resin B2 solution; solvent (E): 6.2 parts of propylene glycol monomethyl ether acetate; solvent (E): N,N-di 630 parts of methylformamide; and 0.063 part of surfactant: polyether-modified polysiloxane oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) were mixed to obtain Coloring Composition 9.

[Sublimation evaluation]

Example 11

After applying the coloring composition 1 on a 2-inch square glass substrate (EagleXG; manufactured by Corning) by a spin coating method, a coloring composition layer was formed at 100° C. for 3 minutes. The film thickness was measured using DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd. This colored coating film and the resin coating film (SJSM) for a sublimation test obtained above were opposed to each other with an interval of 70 μm, and post-baking was performed at 220° C. for 40 minutes. The color difference (ΔEab*) before and after heating of the resin coating film for a sublimation test (SJSM) was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS (OLYMPUS)). As long as the color difference (ΔEab*) is 5.0 or more, it means that the colorant has sublimation properties. The results are shown in Table 9. In Table 9, ○ indicates that the colorant does not have sublimation, and × indicates that the colorant has sublimation.

Example 12

Except having replaced the coloring composition 1 obtained in Example 3 with the coloring composition 2, the same operation as Example 11 was performed, and the sublimation evaluation was performed. The results are shown in Table 9.

Example 13

Except having replaced the coloring composition 1 obtained in Example 3 with the coloring composition 3, the same operation as Example 11 was performed, and the sublimation evaluation was performed. The results are shown in Table 9.

Example 14

Except having replaced the coloring composition 1 obtained in Example 3 with the coloring composition 4, the same operation as Example 11 was performed, and the sublimation evaluation was performed. The results are shown in Table 9.

Example 15

Except having replaced the coloring composition 1 obtained in Example 3 with the coloring composition 5, it carried out the same operation as Example 11, and evaluated the sublimation property. The results are shown in Table 9.

Example 16

Except having replaced the coloring composition 1 obtained in Example 3 with the coloring composition 6, the same operation as Example 11 was performed, and the sublimation evaluation was performed. The results are shown in Table 9.

Example 17

Except having replaced the coloring composition 1 obtained in Example 3 with the coloring composition 7, the same operation as Example 11 was performed, and the sublimation evaluation was performed. The results are shown in Table 9.

Example 18

Except having replaced the coloring composition 1 obtained in Example 3 with the coloring composition 8, it carried out the same operation as Example 11, and evaluated the sublimation property. The results are shown in Table 9.

Comparative Example 2

Except having replaced the coloring composition 1 obtained in Example 3 with the coloring composition 9, the same operation as Example 11 was performed, and the sublimation evaluation was performed. The results are shown in Table 9.

From the above-mentioned results, it is understood that the coloring composition containing the compound of the present invention reduces the sublimation of the colorant.

Example 19

Colorant (A): 100 parts of the compound represented by formula (I-74), dispersant (BYK-LPN21324; manufactured by Japan BYK Chemical Co., Ltd.) 130 parts, resin (B): 170 parts of resin B4 solution, and a solvent (E): Mix 610 parts of propylene glycol monomethyl ether acetate, and disperse 380 parts of the coloring composition of the compound represented by formula (I-74) using a bead mill; Colorant (A): CI Pigment Yellow 138 (pigment ) 18 parts, 7.6 parts of dispersant, 7.6 parts of resin, and solvent (E): 120 parts of propylene glycol monomethyl ether succinate are mixed, and the full amount of the pigment dispersion liquid with the pigment dispersed by the bead mill will be used; colorant (A): 4.2 parts of a compound represented by the following formula (produced by the method described in Japanese Patent Laid-Open No. 2013-235257);

Resin (B): 21 parts of resin B3 solution; polymerizable compound (C): polymerizable compound (A9550; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) 25 parts; polymerization initiator (D): compound represented by the following formula (made by Changzhou Qiangli Electronic New Materials Co., Ltd.) 6.6 copies;

Solvent (E): 170 parts of 4-hydroxy-4-methyl-2-pentanone; Solvent (E): 250 parts of propylene glycol monomethyl ether acetate; and surfactant: polyether modified polysiloxane oil ( Toray Silicone SH8400; Toray Dow Corning Co., Ltd.) 0.075 part was mixed to obtain Colored Curable Composition 1.

[Production of coloring pattern]

After applying the colored curable composition 1 on a 2-inch square glass substrate (EagleXG; manufactured by Corning) by a spin coating method, it was prebaked at 100° C. for 3 minutes to form a colored curable composition layer. After cooling, the interval between the substrate on which the coloring curable composition layer was formed and the mask made of quartz glass was set to 200 μm, and an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.) was used to expose the film to 80 mJ/cm ² in the atmosphere. exposure (365nm reference) exposure. In addition, a mask in which a 100 μm line-and-space pattern was formed was used. After exposure, the colored curable composition layer was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25° C. for 70 seconds, developed and washed with water. By post-baking this colored coating film at 230° C. for 30 minutes, a colored pattern was obtained.

[Sublimation evaluation]

After applying the colored curable composition 1 on a 2-inch square glass substrate (EagleXG; manufactured by Corning) by a spin coating method, it was prebaked at 100° C. for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the coloring curable composition layer was formed was exposed to an exposure amount of 80 mJ/cm ² (365 nm reference) in the atmosphere using an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.). After exposure, the colored curable composition layer was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25° C. for 70 seconds to develop and rinse with water.

The film thickness was measured using DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.

This colored coating film and the resin coating film (SJSM) for a shininess test obtained above were opposed to each other at a distance of 70 μm, and post-baking was performed at 220° C. for 40 minutes.

The color difference (ΔEab*) before and after heating of the resin coating film for a sublimation test (SJSM) was measured with a colorimeter (OSP-SP-200; manufactured by OLYMPUS). As long as the color difference (ΔEab*) is 5.0 or more, it means that the colorant has sublimation properties. The results are shown in Table 10. In Table 10, ○ indicates that the colorant does not have sublimation, and × indicates that the colorant has sublimation.

Example 20

Colorant (A): 100 parts of the compound represented by formula (I-74), 130 parts of dispersant (BYK-LPN21324; Japan BYK Chemical Co., Ltd.), resin (B): 170 parts of resin B4 solution, and a solvent (E): Mix 610 parts of propylene glycol monomethyl ether acetate, and disperse 340 parts of the coloring composition in which the compound represented by (I-74) is dispersed by a bead mill; Colorant (A): CI Pigment Yellow 138 (pigment) 18 parts, 7.6 parts of dispersant, 7.6 parts of resin, and solvent (E): 120 parts of propylene glycol monomethyl ether acetate are mixed, and the full amount of the pigment dispersion liquid with the pigment dispersed by the bead mill is used; colorant (A): the following 7.8 parts of the compound represented by the formula (produced by the method described in Japanese Patent Laid-Open No. 2013-235257);

Resin (B): 27 parts of resin B3 solution; polymerizable compound (C): polymerizable compound (A9550; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) 26 parts; polymerization initiator (D): compound represented by the following formula (made by Changzhou Qiangli Electronic New Materials Co., Ltd.) 6.8 copies;

Solvent (E): 170 parts of 4-hydroxy-4-methyl-2-pentanone; Solvent (E): 270 parts of propylene glycol monomethyl ether acetate; and surfactant: polyether modified polysiloxane oil ( Toray Silicone SH8400; Toray Dow Corning Co., Ltd.) 0.075 part was mixed to obtain a colored curable composition 2.

The same operations as in Example 19 were carried out, except that the colored curable composition 1 was replaced with the colored curable composition 2, and the preparation of the colored pattern and the evaluation of the sublimation were carried out. The sublimation evaluation results are shown in Table 10.

Example 21

Colorant (A): 100 parts of the compound represented by formula (I-74), 130 parts of dispersant (BYK-LPN21324; Japan BYK Chemical Co., Ltd.), resin (B): 170 parts of resin B4 solution, and a solvent (E): Mix 610 parts of propylene glycol monomethyl ether acetate, and disperse 290 parts of the coloring composition of the compound represented by the formula (I-74) using a bead mill; Colorant (A): CI Pigment Yellow 138 (pigment ) 23 parts, 9.6 parts of dispersant, 9.6 parts of resin, and solvent (E): 150 parts of propylene glycol monomethyl ether acetate are mixed, and the full amount of the pigment dispersion liquid with the pigment dispersed by the bead mill will be used; colorant (A): 5.1 parts of a compound represented by the following formula (produced by the method described in Japanese Patent Laid-Open No. 2013-235257);

Resin (B): 31 parts of resin B3 solution; polymerizable compound (C): polymerizable compound (A9550; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) 27 parts; polymerization initiator (D): compound represented by the following formula (made by Changzhou Qiangli Electronic New Materials Co., Ltd.) 7.2 copies;

Solvent (E): 170 parts of 4-hydroxy-4-methyl-2-pentanone; Solvent (E): 280 parts of propylene glycol monomethyl ether acetate; and surfactant: polyether modified polysiloxane oil ( Toray Silicone SH8400; Toray Dow Corning Co., Ltd.) 0.075 part was mixed to obtain a colored curable composition 3.

Except having replaced the colored curable composition 1 with the colored curable composition 3, it carried out the same operation as Example 19, and performed the preparation of a colored pattern and the evaluation of sublimation. The sublimation evaluation results are shown in Table 10.

Example 22

Colorant (A): 100 parts of the compound represented by formula (I-74), 130 parts of dispersant (BYK-LPN21324; Japan BYK Chemical Co., Ltd.), resin (B): 170 parts of resin B4 solution, and solvent (E): Mix 610 parts of propylene glycol monomethyl ether acetate, and disperse 270 parts of the coloring composition of the compound represented by the formula (I-74) using a bead mill; Colorant (A): CI Pigment Yellow 138 (pigment ) 23 parts, 9.6 parts of dispersant, 9.6 parts of resin, and solvent (E): 150 parts of propylene glycol monomethyl ether acetate are mixed, and the full amount of the pigment dispersion liquid with the pigment dispersed by the bead mill is used; colorant (A): 7.4 parts of a compound represented by the following formula (manufactured by the method described in Japanese Patent Laid-Open No. 2013-235257);

Resin (B): 35 parts of resin B3 solution; polymerizable compound (C): polymerizable compound (A9550; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) 27 parts; polymerization initiator (D): compound represented by the following formula (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) 7.3 copies;

Solvent (E): 170 parts of 4-hydroxy-4-methyl-2-pentanone; Solvent (E): 290 parts of propylene glycol monomethyl ether acetate; and surfactant: polyether modified polysiloxane oil ( Toray Silicone SH8400; Toray Dow Corning Co., Ltd.) 0.075 part was mixed to obtain a colored curable composition 4.

The same operations as in Example 19 were carried out, except that the colored curable composition 1 was replaced by the colored curable composition 4, and the preparation of the colored pattern and the evaluation of the sublimation were carried out. The sublimation evaluation results are shown in Table 10.

Example 23

Except having replaced the compound represented by formula (I-74) with the compound represented by formula (I-33), it carried out similarly to Example 19, obtained the coloring curable composition 5, and performed the preparation of a coloring pattern and sublimation evaluation. The sublimation evaluation results are shown in Table 10.

Example 24

Except having replaced the compound represented by formula (I-74) with the compound represented by formula (I-33), it carried out similarly to Example 22, obtained the coloring curable composition 6, and performed the preparation of a coloring pattern and sublimation evaluation. The sublimation evaluation results are shown in Table 10.

Example 25

Except having replaced the compound represented by formula (I-74) with the compound represented by formula (I-73), it carried out similarly to Example 19, obtained the colored curable composition 7, and performed the preparation of a colored pattern and the evaluation of sublimation. The sublimation evaluation results are shown in Table 10.

Example 26

Except having replaced the compound represented by formula (I-74) with the compound represented by formula (I-73), it carried out similarly to Example 22, obtained the coloring curable composition 8, and performed the preparation of a coloring pattern and sublimation evaluation. The sublimation evaluation results are shown in Table 10.

Example 27

A colored curable composition 9 was obtained in the same manner as in Example 19 except that the compound represented by the formula (I-74) was replaced by the compound represented by the formula (I-23), and the preparation of the colored pattern and the evaluation of the sublimation were carried out. The sublimation evaluation results are shown in Table 10.

Example 28

Except having replaced the compound represented by formula (I-74) with the compound represented by formula (I-23), it carried out similarly to Example 22, obtained the coloring curable composition 10, and performed the preparation of a coloring pattern and sublimation evaluation. The sublimation evaluation results are shown in Table 10.

Comparative Example 3

A colored curable composition 11 was obtained in the same manner as in Example 19 except that the compound represented by the formula (I-74) was replaced by coumarin 6, and the preparation of a colored pattern and the evaluation of sublimation were performed. The sublimation evaluation results are shown in Table 10.

Comparative Example 4

A colored curable composition 12 was obtained in the same manner as in Example 22 except that the compound represented by the formula (I-74) was replaced by coumarin 6, and the preparation of a colored pattern and the evaluation of sublimation were performed. The sublimation evaluation results are shown in Table 10.

From the above-mentioned results, it is understood that the colorable curable composition containing the compound of the present invention reduces the sublimation of the colorant.

[Possibility of industrial application]

The compound of the present invention can improve heat resistance and reduce the sublimation properties of colorants, and can be suitably used for display devices such as color filters and liquid crystal display devices.

Claims (11)

A compound represented by formula (I),

In formula (I), R ^N1 and R ^N2 independently represent a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent; Ar ¹ represents an aromatic hydrocarbon group with 6 to 40 carbon atoms that may have a substituent; R ¹ to R ⁸ independently represents a hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N ( R ¹⁰² ) ₂ , -CON(R ¹⁰² ) ₂ , -N(R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N(R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON(R ¹⁰² ) ₂ , halogen Atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, or a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent; R ¹⁰¹ represents a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent; R ¹⁰² Represents a hydrogen atom, a hydrocarbon group with a carbon number of 1 to 40 that may have a substituent; M represents a hydrogen atom or an alkali metal atom; when there are multiple R ¹⁰¹ , R ¹⁰² and M, these may be the same or different; A ^g- represents g-valent anion; g represents an integer from 1 to 14. The compound according to claim 1, wherein A ^g- is an anion or fluorine-containing anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements . The compound according to claim 1 or 2, wherein A ^g- contains at least one element selected from the group consisting of tungsten and phosphorus and oxygen as essential elements of an anion or a fluorine-containing anion. The compound according to claim 1 or 2, wherein A ^g- is an anion containing at least one element selected from the group consisting of tungsten and phosphorus and oxygen as essential elements. A coloring composition comprising the compound described in any one of the first to fourth items in the scope of application and a solvent. The coloring composition as described in item 5 of the scope of the application further contains a resin. The coloring composition as described in item 5 or 6 of the claimed scope further contains a yellow colorant, an orange colorant or a red colorant. A coloring curable composition comprising the coloring composition described in any one of items 5 to 7 of the patent application scope, and a polymerizable compound. The coloring curable composition as described in item 8 of the patent application scope further contains a polymerization initiator. A color filter is formed by the coloring composition described in any one of claims 5 to 7 of the patent application scope or the coloring curable composition described in the claim 8 or 9 of the patent application scope. A liquid crystal display device comprising the color filter described in item 10 of the patent application scope.