TWI778975B - Coloring composition - Google Patents

Abstract

The present invention relates to a coloring composition comprising a compound represented by formula (I) and a resin.

(In the formula (I), R^N1 and R^N2 are each independently represents an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent. R^N3 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R¹ to R⁸ are each independently represents a hydrogen atom, -CO-R¹⁰², -COO-R¹⁰¹, -OCO-R¹⁰², -O-R¹⁰², -SO₂-R¹⁰¹, -SO₂N(R¹⁰²)₂, -CON (R¹⁰²)₂, -N(R¹⁰²)₂, -NHCO-R¹⁰², a halogen atom, a cyano group, a 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

Coloring composition

The present invention relates to a compound and a coloring composition useful as a colorant.

Dyes are used, for example, in the fields of fiber materials, liquid crystal display devices, inkjet, etc. to express colors by reflected light or transmitted light. As such a dye, coumarin 6 represented by the following formula is known (JP-A-2006-154740).

The present invention includes the following inventions.

[1] A coloring composition comprising a compound represented by formula (I) and a resin.

[In the formula (I), R ^N1 and R ^N2 independently represent an aliphatic hydrocarbon group with a carbon number of 1 to 40 that may have a substituent, and R ^N3 represents a hydrocarbon group with a carbon number of 1 to 40 that may have a substituent or an aliphatic hydrocarbon group that may have a substituent For heterocyclic groups with substituents, R ¹ to R ⁸ independently represent hydrogen atoms, -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, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent , R ¹⁰¹ represents a hydrocarbon group with a carbon number of 1 to 40 that may have a substituent or a heterocyclic group 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, or a hydrocarbon group that may have a substituent The heterocyclic group of the group, M represents a hydrogen atom or an alkali metal atom, and when there are multiple R ¹⁰¹ , R ¹⁰² and M, they may be the same or different. A ^g- represents an anion with a valence of g, and g represents an integer from 1 to 14].

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

[3] The coloring composition according to [1] or [2], wherein ^Ag- is an anion containing at least one element selected from the group consisting of tungsten and phosphorus and oxygen as essential elements, or fluoride-containing anions.

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

[5] The coloring composition according to any one of [1] to [4], wherein R ^N1 and R ^N2 are independently an alkyl group having 1 to 10 carbon atoms which may have a substituent.

[6] The coloring composition according to any one of [1] to [5], which further contains a solvent.

[7] The colored composition according to any one of [1] to [6], which further contains a yellow colorant, an orange colorant or a red colorant.

[8] A colored curable composition comprising the colored composition according to any one of [1] to [7], and a polymerizable compound.

[9] The colored curable composition as described in [8], further comprising a polymerization initiator.

[10] A color filter formed of the colored composition described in any one of [1] to [7] or the colored curable composition described in [8] or [9].

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

[12] A compound represented by the formula (I-B).

[In the formula (IB), R ^N1 and R ^N2 independently represent an aliphatic hydrocarbon group with a carbon number of 1 to 40 that may have a substituent, and R ^N3 represents a hydrocarbon group with a carbon number of 1 to 40 that may have a substituent or an aliphatic hydrocarbon group that may have a substituent For heterocyclic groups with substituents, R ¹ to R ⁸ independently represent hydrogen atoms, -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, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent , R ¹⁰¹ represents a hydrocarbon group with a carbon number of 1 to 40 that may have a substituent or a heterocyclic group 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, or a hydrocarbon group that may have a substituent The heterocyclic group of the group, M represents a hydrogen atom or an alkali metal atom, and when there are multiple R ¹⁰¹ , R ¹⁰² and M, these may be the same or different, and B ^h- represents a group selected from tungsten, molybdenum, silicon , and at least one element of the group consisting of phosphorus, and an anion of h valence containing oxygen as an essential element, h represents an integer of 1 to 14].

[13] The compound according to [12], wherein B ^h- is an anion containing at least one element selected from the group consisting of tungsten and phosphorus, and oxygen as essential elements.

[14] The compound according to [12] or [13], wherein R ^N1 and R ^N2 independently represent an optionally substituted alkyl group having 1 to 10 carbon atoms.

The coloring composition of the present invention contains a compound represented by formula (I) (hereinafter referred to as compound (I)) and a resin (hereinafter referred to as resin (B)).

Compound (I) includes its tautomers, salts thereof.

Compound (I) can be used as a colorant.

The coloring composition of the present invention may contain 1 type or 2 or more types of compounds (I).

The coloring composition of the present invention may contain a solvent (hereinafter, sometimes referred to as a solvent (E)).

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

The coloring composition of the present invention may contain a coloring agent other than compound (I) (hereinafter referred to as coloring agent (A1). In addition, compound (I) and coloring agent (A1) are collectively referred to as "coloring agent (A1) below." agent (A)".

The coloring agent (A1) may contain 1 type or 2 or more types of coloring agents.

The coloring agent (A1) preferably contains a yellow coloring agent, an orange coloring agent or a red coloring agent.

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

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

The colored curable composition of the present invention may contain a polymerization initiation aid (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).

[In formula (I), R ^N1 and R ^N2 independently represent an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have substituents.

R ^N3 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ¹ to R ⁸ 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, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

R ¹⁰¹ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ¹⁰² 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.

The M system represents a hydrogen atom or an alkali metal atom.

When there are plural R ¹⁰¹ , R ¹⁰² and M, these may be the same or different.

The A ^g- series represents an anion of g valency.

g represents an integer from 1 to 14].

The carbon number of the aliphatic hydrocarbon group represented by R ^N1 and R ^N2 is 1-40, preferably 1-30, more preferably 1-20, more preferably 1-15, particularly preferably 1-10.

The aliphatic hydrocarbon groups represented by R ^N1 and R ^N2 may be saturated or unsaturated, chain or alicyclic.

The saturated or unsaturated chain aliphatic hydrocarbon groups represented by R ^N1 and R ^N2 include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, deca One base, dodecyl, heptadecyl, octadecyl, and eicosyl and other linear alkyl groups; isopropyl, isobutyl, second butyl, third butyl, (2-ethyl ) butyl, isopentyl, neopentyl, third pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) Pentyl, isohexyl, (5-methyl)hexyl, (2-ethyl)hexyl and (3-ethyl)heptyl and other branched chain alkyl groups; vinyl, 1-propenyl, 2-propene (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl)) vinyl, Alkenyl groups such as (1,2-dimethyl)propenyl and 2-pentenyl, etc. The carbon number of the saturated or unsaturated chain hydrocarbon group is preferably 1-30, more preferably 1-20, more preferably 1-15, particularly preferably 1-10, and even more preferably 1-8. More preferably, it is 1-5. Among them, a linear or branched alkyl group having 1 to 10 carbons, preferably 1 to 8 carbons is particularly preferred, and methyl or ethyl is particularly preferred.

Saturated or unsaturated alicyclic hydrocarbon groups represented by R ^N1 and R ^N2 include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methyl Cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-di Methylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-di Methylcyclohexyl, 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-octyl Cycloalkyl groups such as cyclohexyl and 4-cyclohexylcyclohexyl; cyclohexenyl (such as cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl and other cycloalkenyl groups; nor Camphenyl, adamantyl, bicyclo[2.2.2]octane, etc. The carbon number of the saturated or unsaturated alicyclic hydrocarbon group is preferably from 3 to 30, preferably from 3 to 20, more preferably from 4 to 20, further preferably from 4 to 15, and even more preferably from 5 to 15, Optimal is 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl are particularly preferred.

The aliphatic hydrocarbon group represented by R ^N1 and R ^N2 may be a combination of the above-mentioned aliphatic hydrocarbon group and an aromatic hydrocarbon group having 1 to 40 carbon atoms (for example, at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group, and an aromatic hydrocarbon group). A group of hydrocarbon groups) combined base.

Such aromatic hydrocarbon groups include phenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, phenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl Propylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 2,4,6-trimethylphenyl (mesityl), 4 -Ethylphenyl, 4-butylphenyl, 4-pentylphenyl, 2,6-bis(2-propyl)phenyl, 4-cyclohexylphenyl, 2,4,6-trimethyl Phenyl, 4-octylphenyl, 4-vinylphenyl, 1-naphthyl, 2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8 - Aromatic hydrocarbon groups such as tetrahydro-2-naphthyl, fenyl, phenanthrenyl, anthracenyl, pyrenyl, etc. The carbon number of the aforementioned aromatic hydrocarbon group is preferably 6-30, more preferably 6-20, more preferably 6-15.

In terms of the group formed by combining the above-mentioned aliphatic hydrocarbon group and an aromatic hydrocarbon group having 1 to 40 carbon atoms (for example, at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group, and an aromatic hydrocarbon group), there are listed Aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenethyl; aralkenyl groups such as phenylvinyl; aralkynyl groups such as phenylethynyl; biphenyl, terphenyl, etc. Phenyl with one or more phenyl groups bonded; cyclohexylmethylphenyl, benzylphenyl, (dimethyl(phenyl)methyl)phenyl, etc. The group represented by R ^N1 and R ^N2 is a combination of the above-mentioned hydrocarbon groups (such as chain hydrocarbon groups and alicyclic hydrocarbon groups), such as cyclopropylmethyl, cyclopropylethyl , cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, 2-methylcyclohexylmethyl, cyclohexylethyl, adamantylmethyl, etc. An alkyl group having one or more alicyclic hydrocarbon groups.

The carbon number of the aforementioned hydrocarbons is preferably from 4 to 30, preferably from 6 to 30, more preferably from 6 to 20, still more preferably from 4 to 20, more preferably from 4 to 15, especially preferably from 6 to 15 .

The carbon number of the hydrocarbon group represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² is 1 to 40, preferably 1 to 30, more preferably 1 to 20, more preferably 1 to 15, especially preferably 1 to 10.

The hydrocarbon groups with 1 to 40 carbons represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² can be aliphatic hydrocarbon groups and aromatic hydrocarbon groups, and the aliphatic hydrocarbon groups can be saturated or unsaturated, and can be chain or alicyclic.

Saturated or unsaturated chain hydrocarbon groups represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl , nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl and other linear alkyl groups; isopropyl, isobutyl, second butyl, third Butyl, (2-ethyl)butyl, isopentyl, neopentyl, third pentyl, (1-methyl)pentyl, (2-methyl)pentyl, (1-ethyl)pentyl Base, (3-ethyl)pentyl, isohexyl, (5-methyl)hexyl, (2-ethyl)hexyl and (3-ethyl)heptyl and other branched chain alkyl groups; vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2 Alkenyl groups such as -propenyl))vinyl, (1,2-dimethyl)propenyl, and 2-pentenyl, etc. The carbon number of the aforementioned saturated or unsaturated chain hydrocarbon group is preferably 1-30, preferably 1-20, more preferably 1-15, particularly preferably 1-10, and even more preferably 1-8. Among them, a linear or branched alkyl group with 1 to 10 carbons, preferably 1 to 8 carbons is particularly preferred, and methyl or ethyl is particularly preferred.

The saturated or unsaturated alicyclic hydrocarbon groups represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclo Hexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethyl Cyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl Cyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl Cyclohexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4- Cycloalkyl such as pentylcyclohexyl, 4-octylcyclohexyl, 4-cyclohexylcyclohexyl; cyclohexenyl (such as cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclohexyl Cycloalkenyl such as octenyl; norbornyl, adamantyl, bicyclo[2.2.2]octane, etc. The carbon number of the aforementioned saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, preferably 3 to 20, more preferably 4 to 20, further preferably 4 to 15, and even more preferably 5 to 15 , preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl are particularly preferred.

The aromatic hydrocarbon groups represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² include phenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-dimethylphenyl, 2 ,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4 -Vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl , 2,4,6-trimethylphenyl, 4-ethylphenyl, 4-butylphenyl, 4-pentylphenyl, 2,6-bis(2-propyl)phenyl, 4-cyclohexyl Phenyl, 2,4,6-trimethylphenyl, 4-octylphenyl, 4-vinylphenyl, 1-naphthyl, 2-naphthyl, 5,6,7,8-tetrahydro- Aromatic hydrocarbon groups such as 1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, fenyl, phenanthrenyl, anthracenyl, pyrenyl, etc. The carbon number of the aforementioned aromatic hydrocarbon group is preferably 6-30, more preferably 6-20, more preferably 6-15.

The hydrocarbon group represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may be a combination of the above-mentioned hydrocarbon groups (such as aromatic hydrocarbon groups, at least one of chain hydrocarbon groups and alicyclic hydrocarbon groups) The bases include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenethyl; aralkenyl groups such as phenylvinyl; aralkynyl groups such as phenylethynyl; biphenyl , terphenyl, and other phenyl groups bonded to one or more phenyl groups; cyclohexylmethylphenyl, benzylphenyl, (dimethyl(phenyl)methyl)phenyl, etc.

The group represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may be, for example, cyclopropyl Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, Cyclobutylethyl, Cyclopentylmethyl, Cyclopentylethyl, Cyclohexylmethyl, 2-Methylcyclohexylmethyl, Cyclohexylethyl An alkyl group to which one or more alicyclic hydrocarbon groups are bonded, such as , adamantylmethyl, etc.

The carbon number of the aforementioned hydrocarbons is preferably 4-30, more preferably 6-30, further preferably 6-20, still more preferably 4-20, more preferably 4-15, particularly preferably 6-15.

The aliphatic hydrocarbon groups represented by R ^N1 and R ^N2 , and the hydrocarbon groups represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may have substituents. The substituent may be monovalent or divalent. The two linkages of the divalent substituent are preferably bonded to the same carbon atom to form a double bond.

The monovalent substituents include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, second butoxy, third butoxy, pentyloxy yl, hexyloxy, (2-ethyl)hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) Hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenoxy, o-tolyloxy, 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, 3,5-dicyanophenoxy, 4-methoxyphenoxy, 2-methoxyphenoxy group, 3-methoxyphenoxy group, 4-ethoxyphenoxy group, 2-ethoxyphenoxy group, 3-ethoxyphenoxy group, etc., and groups represented by the following formula etc. on one side Bonded with a hydrocarbon group with a carbon number of 1 to 20 (preferably a carbon number of 1 to 10) or a derivative thereof (such as 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 (preferably octyl sulfamoyl) and other derivatized groups) oxygen group;

Methylthio, ethylthio, propylthio, butylthio, tertiary butylthio, pentylthio, hexylthio, (2-ethyl)hexylthio, heptylthio, octylthio, nonylthio 1 to 20 carbons (preferably 1 to 10) Hydrocarbyl sulfur group; epoxy group, oxetanyl group, tetrahydrofuryl group, tetrahydropyranyl group; formyl group; acetyl group, propionyl group, butyryl group, 2,2-dimethylpropane Acyl, Pentyl, Hexyl, (2-Ethyl)hexyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Helicyl , benzoyl, etc., and groups represented by the following formulas are bonded with hydrocarbon groups with carbon numbers of 1 to 20 (preferably with carbon numbers of 1 to 11) or derivatives thereof (such as carboxyl, sulfonic acid groups , nitro, hydroxyl, halogen (preferably chlorine atom), carbon number 1 to 10 alkyl sulfamoyl group (preferably octyl sulfamoyl group), etc. When the carbonyl group is set as an alkanoyl group, the carbon number is preferably 2 to 12);

Methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, tertiary butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl)hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxy Carbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, eicosyloxycarbonyl, phenoxycarbonyl, o-tolyloxycarbonyl, etc., and groups represented by the following formulas are bonded with carbon A hydrocarbon group with a number of 1 to 20 (preferably a carbon number of 1 to 10) or a derivative thereof (such as a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a carbon number of 1 to 10 Oxycarbonyl group derived from alkylsulfamoyl (preferably octylsulfamoyl) group);

Amino group; N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group Amino, N-isopropylamino, N,N-diisopropylamino, N-butylamino, N,N-dibutylamino, N-isobutylamino, N, N-diisobutylamine, N-second butylamine, N,N-disecond butylamine, N-tertiary butylamine, N,N-ditertiary 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-di(2-ethyl)hexylamino, N-heptylamino, N,N- Diheptylamino, N-octylamino, N,N-dioctylamino, N-nonylamino, N,N-dinonylamino, N-phenylamino, N,N -Diphenylamino, N,N-ethylmethylamino, N,N-propylmethylamino, N,N-isopropylmethylamino, N,N-butylmethylamino, N-decylamino, N,N-decylmethylamino, N-undecylamino, N,N-undecylmethylamino, N-dodecylamino, N,N- Dodecylmethylamino, N-eicosylamino, N,N-eicosylmethylamino, N,N-tert-butylmethylamino, N,N-phenylmethylamino, etc. , and the group represented by the following formula is replaced by 1 or 2 hydrocarbon groups with 1 to 20 carbons (preferably 1 to 10 carbons) or its derivation groups (such as carboxyl, sulfonic acid, nitro, hydroxyl , a halogen (preferably a chlorine atom), an alkylsulfamoyl group with 1 to 10 carbons (preferably an octylsulfamoyl group), etc.) substituted amino groups;

Sulfamoyl; N-methylsulfamoyl, N,N-dimethylsulfamoyl, N-ethylsulfamoyl, N,N-diethylsulfamoyl, N-propyl Aminosulfonyl, N,N-dipropylsulfamoyl, N-isopropylsulfamoyl, N,N-diisopropylsulfamoyl, N-butylsulfamoyl, N,N-dibutyl sulfamoyl, N-isobutyl sulfamoyl, N,N-diisobutyl sulfamoyl, N-second butyl sulfamoyl, N,N- Di-2-butyl sulfamoyl, N-tert-butyl sulfamoyl, N,N-di-tert-butyl sulfamoyl, N-pentyl sulfamoyl, N,N-dipentyl Aminosulfamoyl, N-(1-ethylpropyl)sulfamoyl, N,N-bis(1-ethylpropyl)sulfamoyl, N-hexylsulfamoyl, N,N -Dihexylsulfamoyl, N-(2-ethyl)hexylsulfamoyl, N,N-di(2-ethyl)hexylsulfamoyl, N-heptylsulfamoyl, N, N-diheptylsulfamoyl, N-octylsulfamoyl, N,N-dioctylsulfamoyl, N,N-octylmethylsulfamoyl, N-nonylsulfamoyl Acyl, N,N-dinonylsulfamoyl, N-phenylsulfamoyl, N,N-diphenylsulfamoyl, N,N-ethylmethylsulfamoyl, N ,N-Propylmethylsulfamoyl, N,N-isopropylmethylsulfamoyl, N,N-butylmethylsulfamoyl, N-decylmethylsulfamoyl, N,N- Decylmethylsulfamoyl, N-undecylsulfamoyl, N,N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N,N-dodecyl Methylsulfamoyl, N-eicosylsulfamoyl, N,N-eicosylmethylsulfamoyl, N,N-tert-butylmethylsulfamoyl, N,N-phenyl Methylsulfamoyl group, etc., and groups represented by the following formula, etc., are replaced by 1 or 2 hydrocarbon groups with 1 to 20 carbons (preferably 1 to 10 carbons) or their derivatives (such as carboxyl, sulfonic Acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkyl sulfamoyl group with 1 to 10 carbons (preferably octyl sulfamoyl group), etc.) Sulfamoyl;

Formylamine; Acetylamine, Propionylamine, Butyrylamine, 2,2-Dimethylpropionylamine, Pentylamine, Caproylamine, (2- Ethyl) caproylamine, heptylamine, octylamine, nonacylamine, decylamine, undecylamine, dodecylamine, eicosylamine Amino groups, benzoylamine groups, etc., and groups represented by the following formulas are bonded to hydrocarbon groups with 1 to 20 carbons (preferably 1 to 12 carbons) or derivatives thereof (such as carboxyl, A sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group with 1 to 10 carbons (preferably an octylsulfamoyl group), etc.) Amino group substituted with carbonyl group (when the carbonylamino group is set as an alkylamino group, the carbon number is preferably 1 to 12);

Hydroxyl; 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, potassium); Sulfonic acid group, -SO ₃ M ² ( ^M2 is an alkali metal, preferably lithium, sodium, potassium); nitro; cyano; formyloxy; acetyloxy, propionyloxy, butyryloxy, 2,2-dimethyl Propyloxy, pentyloxy, hexyloxy, (2-ethyl)hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy group, dodecyloxy group, eicosyloxy group, benzoyloxy group, etc., and groups represented by the following formulas, etc. are bonded with carbon number 1 to 20 (preferably carbon number 1 to 10) Hydrocarbyl or its derivation group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), carbon number 1 to 10 alkyl sulfamoyl group (preferably octyl sulfamoyl group) The carbonyloxy group of the derived group) (the carbonyloxy group is an alkyloxy group, the carbon number is preferably 1 to 10);

Methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl)hexylsulfonyl, heptylsulfonyl octylsulfonyl, nonylsulfonyl, decylsulfonyl, undecylsulfonyl, dodecylsulfonyl, eicosylsulfonyl, phenylsulfonyl, p-tolyl A sulfonyl group, etc., and a group represented by the following formula are bonded to a hydrocarbon group with a carbon number of 1 to 20 (preferably a carbon number of 1 to 10) or a derivative thereof (such as a carboxyl group, a sulfonic acid group, a nitro group, A sulfonyl group derived from a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group with 1 to 10 carbons (preferably an octylsulfamoyl group), etc.;

Aminoformyl; N-methylaminoformyl, N,N-dimethylaminoformyl, N-ethylaminoformyl, N,N-diethylaminoformyl base, N-propylaminoformyl, N,N-dipropylaminoformyl, N-isopropylaminoformyl, N,N-diisopropylaminoformyl, N-butylaminoformyl, N,N-dibutylaminoformyl, N-isobutylaminoformyl, N,N-diisobutylaminoformyl, N- Second butylaminoformyl, N, N-disecond butylaminoformyl, N-tert-butylaminoformyl, N, N-di-tert-butylaminoformyl N-pentylaminoformyl, N,N-dipentylaminoformyl, N-(1-ethylpropyl)aminoformyl, N,N-di(1-ethyl propyl)aminoformyl, N-hexylaminoformyl, N,N-dihexylaminoformyl, N-(2-ethyl)hexylaminoformyl, N,N- Di(2-ethyl)hexylaminoformyl, N-heptylaminoformyl, N,N-diheptylaminoformyl, N-octylaminoformyl, N,N -Dioctylaminoformyl, N-nonylaminoformyl, N,N-octylmethylaminoformyl, N,N-octylbutylaminoformyl, N, N-Dinonylaminoformyl, N-Phenylaminoformyl, N,N-Diphenylaminoformyl, N,N-Ethylmethylaminoformyl, N, N-propylmethylaminoformyl, N,N-isopropylmethylaminoformyl, N,N-butylmethylaminoformyl, N-decylaminoformyl, N ,N-decylmethylaminoformyl, N-undecylaminoformyl, N,N-undecylmethylaminoformyl, N-dodecylaminoformyl, N,N-dodecylmethylaminoformyl, N-eicosylaminoformyl, N,N-eicosylmethylaminoformyl, N,N-tert-butylmethylamine A base formyl group, N,N-phenylmethylamino formyl group, etc., and a group represented by the following formula are replaced by 1 or 2 carbon number 1 to 20 (preferably carbon number 1 to 10) Hydrocarbyl or its derivation group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), carbon number 1 to 10 alkyl sulfamoyl group (preferably octyl sulfamoyl group) The amino formyl group substituted by the derivatization of the base) and the like;

Trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluoropentyl, perfluorohexyl, perfluoroheptyl, perfluorooctyl, perfluorononyl, Perfluorodecyl, perfluoroundecyl, perfluorododecyl, perfluoroeicosyl, perfluorocyclohexyl, perfluorophenyl and other hydrocarbon groups with 1 to 20 carbon atoms in which all hydrogen atoms are replaced by fluorine atoms; Perfluoroethylmethyl, perfluoropropylmethyl, perfluoroisopropylmethyl, perfluorobutylmethyl, perfluoropentylmethyl, perfluorohexylmethyl, perfluoroheptylmethyl, perfluorooctyl ylmethyl, perfluorononylmethyl, perfluorodecylmethyl, perfluoroundecylmethyl, perfluorododecylmethyl, perfluoroeicosylmethyl, etc. are replaced by all hydrogen atoms through fluorine atoms Substituted straight chain or branched chain alkyl with 1 to 20 carbons; 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl and 2,4, Hydrocarbon groups with 1 to 20 carbons (preferably 1 to 10 carbons) in which a part of hydrogen atoms are substituted by fluorine atoms, such as 6-trifluorophenyl; -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. have been combined with carbon number 1 to 20 (preferably carbon thiocarbonyl group bonded to an alkyl group with a carbon number of 2 to 10), and a thiocarbonyl group bonded to an aryl group with a carbon number of 6 to 20, such as -CO-SC ₆ H ₅ ; *-COCO-R represented by the following formula (where , R is a hydrogen atom, a hydrocarbon group with a carbon number of 1 to 20 (for example, one of the above-mentioned hydrocarbon groups with a carbon number of 1 to 20), or a derivatized group (such as a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, A halogen (preferably a chlorine atom), a group derivatized from an alkylsulfamoyl group (preferably an octylsulfamoyl group) having 1 to 10 carbon atoms)));

*-NRCONR ₂ represented by the following formula (in the formula, R is a hydrogen atom, a hydrocarbon group with 1 to 20 carbons (for example, one of the above-mentioned hydrocarbon groups with 1 to 20 carbons), or a derivative thereof (for example, by Carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group with 1 to 10 carbons (preferably octylsulfamoyl 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);

*-OCONR ₂ represented by the following formula (in the formula, R is a hydrogen atom, a hydrocarbon group with 1 to 20 carbons (for example, one of the above-mentioned hydrocarbon groups with 1 to 20 carbons), or a derivative thereof (for example, by Carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group with 1 to 10 carbons (preferably octylsulfamoyl 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);

*-NRCOOR represented by the following formula (in the formula, R is a hydrogen atom, a hydrocarbon group with 1 to 20 carbons (for example, one of the above-mentioned hydrocarbon groups with 1 to 20 carbons), or a derivative thereof (such as a carboxyl group , sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group with 1 to 10 carbons (preferably octylsulfamoyl group), etc.) , the R can be the same or different from each other, and can also be bonded to each other to form a ring);

*-OP(O)(OCH ₃ ) ₂ etc. *-OP(O)(OR) ₂ (wherein, R is a hydrogen atom, a hydrocarbon group with 1 to 20 carbons (for example, among the hydrocarbon groups listed above, the carbon number 1 to 20), or its derivatized group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group with carbon number 1 to 10 (preferably octylsulfamoyl) and other derivatized groups), the R can be the same or different, 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 1 to 20 Hydrocarbyl (for example, among the above-mentioned hydrocarbon groups satisfying the carbon number of 1 to 20), or its derivatized group (such as carboxyl, sulfonic acid group, nitro, hydroxyl, halogen (preferably chlorine atom), carbon number 1 10 to 10 alkyl sulfamoyl (preferably octyl sulfamoyl) and other derivatized groups), the R may be the same or different from each other, and may be bonded to each other to form a ring), etc. .

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

The substituent of the hydrocarbon group having 1 to 40 carbon atoms preferably includes a substituent of Group s1. The derivatization group disclosed below is based on a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group with a carbon number of 1 to 10 (preferably an octylsulfamate group) Derivatized bases such as acyl groups) are preferred.

[group s1]

Oxygen group bonded with a hydrocarbon group with 1 to 20 carbons or its derivatives on one side; carbonyl bonded with a hydrocarbon group with 1 to 20 carbons or its derivatives; bonded with a hydrocarbon group with 1 to 20 carbons Oxycarbonyl or its derivatized group; amino group; amine group substituted by 1 or 2 hydrocarbon groups with 1 to 20 carbons or its derivatized groups; sulfamoyl group; A sulfamoyl group substituted with a hydrocarbon group of 20 or a derivative thereof; a carbonylamino group bonded to a hydrocarbon group of 1 to 20 carbons or a derivative thereof; a hydroxyl group; a 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; cyano; carbonyloxy bonded to a hydrocarbon group with 1 to 20 carbons or a derivative thereof; sulfonyl bonded to a hydrocarbon group with 1 to 20 carbons or a derivative thereof; carbamoyl Aminoformyl group substituted by 1 or 2 hydrocarbon groups with 1 to 20 carbons or derivatives thereof; hydrocarbon groups with 1 to 20 carbons replaced by all hydrogen atoms by fluorine atoms; all hydrogen atoms A hydrocarbon group with 1 to 20 carbons substituted by a linear or branched chain alkyl group with 1 to 20 carbons substituted by fluorine atoms; a hydrocarbon group with 1 to 20 carbons substituted by fluorine for a part of the hydrogen atoms; side oxygen group .

The substituent of the hydrocarbon group having 1 to 40 carbon atoms preferably includes a substituent of the group s2.

[group s2]

Oxygen group bonded with a hydrocarbon group with 1 to 10 carbons or its derivatives on one side; carbonyl bonded with a hydrocarbon group with 1 to 10 carbons or its derivatives; bonded with a hydrocarbon group with 1 to 10 carbons Oxycarbonyl or its derivatized group; amino group; amino group substituted by 1 or 2 hydrocarbon groups with 1 to 10 carbons; sulfamoyl group; substituted by 1 or 2 hydrocarbon groups with 1 to 10 carbons or A sulfamoyl group substituted with a derivatizing group; a carbonylamino group bonded to a hydrocarbon group with 1 to 10 carbons or a derivatizing group thereof; hydroxyl; a fluorine atom, a chlorine atom, a bromine atom; -CO ₂ M (preferably a carboxyl group ) (M represents a hydrogen atom or an alkali metal atom, preferably represents a hydrogen atom); -SO ₃ M (preferably a sulfonic acid group) (M represents a hydrogen atom or an alkali metal atom, preferably represents a hydrogen atom) ; nitro; cyano; carbonyloxy bonded to a hydrocarbon group with 1 to 10 carbons or a derivative thereof; sulfonyl bonded to a hydrocarbon group with 1 to 10 carbons or a derivative thereof; aminomethyl Acyl group; aminoformyl group substituted by 1 or 2 hydrocarbon groups with 1 to 10 carbons or derivatives thereof; hydrocarbon groups with 1 to 10 carbons replaced by fluorine atoms; all hydrogen Hydrocarbon groups with 1 to 10 carbons substituted by linear or branched chain alkyl groups with 1 to 10 carbon atoms replaced by fluorine atoms; hydrocarbon groups with 1 to 10 carbon atoms replaced by fluorine atoms; side oxygen base.

The hydrocarbon groups having 1 to 40 carbon atoms having substituents represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² include hydrocarbon groups having 1 to 40 carbon atoms having monovalent or divalent substituents, Preferable examples include: a saturated or unsaturated chain hydrocarbon group having a monovalent or divalent substituent having 1 to 30 carbon atoms, a saturated hydrocarbon group having a monovalent or divalent substituent having a carbon number of 3 to 30 Or an unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group with 6 to 30 carbon atoms having a monovalent or divalent substituent, or a combination of hydrocarbon groups with a monovalent or divalent substituent The group having 1 to 30 carbon atoms is more preferably a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, and a saturated or unsaturated chain hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1. or an unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group having 6 to 20 carbon atoms in the substituent of group s1, or a combination of hydrocarbon groups, and a group having 1 to 20 carbon atoms in the substituent of group s1, Particularly preferred examples include: a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbons in a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbons in a substituent of group s2 . An aromatic hydrocarbon group having 6 to 15 carbon atoms in the substituent of group s2 or a combination of hydrocarbon groups, and a group having 1 to 15 carbon atoms in the substituent of group s2.

The heterocyclic group represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may be monocyclic or polycyclic, and is 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 3-30, more preferably 3-22, more preferably 3-20, more preferably 3-18, more preferably 3-15, particularly preferably 3-14.

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、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

、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、

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、啡

等縮合三環系雜環等。 Heterocycles containing a nitrogen atom include: aziridine, azetidine, pyrrolidine, piperidine, piperidine

Monocyclic saturated heterocyclic rings; 2,5-dimethylpyrrole and other pyrroles, 2-methylpyrazole, 3-methylpyrazole and other pyrazoles, imidazoles, 1,2,3-triazoles, 1,2 , 5-membered unsaturated heterocyclic rings such as 4-triazole; pyridine, palladium

, 6-methylpyrimidine and other pyrimidines, pyrimidines

, 1,3,5-three

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

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

phylloline, 3-methylquinone

quinoline

phylloline, quinazoline,

Cinnoline, Tie

,

Pyridine, purine, pteridine, benzopyrazole, benzopiperidine and other condensed bicyclic heterocycles; carbazole, acridine, phenanthrene

Condensation tricyclic heterocyclic rings etc.

烷、1,4-二

烷、1-環戊基二氧雜戊環等單環系飽和雜環；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、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-吡喃、4H-吡喃等6員環系不飽和雜環；1-苯并呋喃、4-甲基苯并吡喃等苯并吡喃、苯并二

呃(benzodioxole)、

唍(chroman)、異

烷等縮合二環系雜環；二苯并哌喃(xanthene)、二苯并呋喃等縮合三環系雜環等。 Heterocyclic rings containing oxygen atoms include: oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-bis

Alkane, 1,4-bis

Monocyclic saturated heterocycles such as alkane and 1-cyclopentyldioxolane; bicyclic rings such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane It is a saturated heterocyclic ring; α-hydantoin, β-propiolactone, γ-butyrolactone, γ-valerolactone, δ-valerolactone and other lactone heterocyclic rings; 2,3-dimethylfuran, 5-membered unsaturated heterocycles such as 2,5-dimethylfuran and furan; 6-membered unsaturated heterocycles such as 2H-pyran and 4H-pyran; 1-benzofuran, 4-methylbenzene Benzopyran such as pyran, benzodi

Er (benzodioxole),

唍 (chroman), different

Alkanes and other condensed bicyclic heterocycles; dibenzopyran (xanthene), dibenzofuran and other condensed tricyclic heterocycles, etc.

Heterocyclic rings containing a sulfur atom include: 5-membered saturated heterocyclic rings such as dithiolane; thiane, 1,3-dithiane, 2-methyl 6-membered saturated heterocyclic rings such as 1,3-dithiacyclohexane; 3-methylthiophene, 2-carboxythiophene and other thiophenes, 4H-thiopyran, benzothiopyran and other benzothiopyrans, etc. 5 Unsaturated heterocycles with member rings; condensed bicyclic heterocycles such as benzothiophene, etc.; condensed tricyclic heterocycles such as thianthracene and 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

(phenoxazine)等縮合三環系雜環等。 Heterocycles containing nitrogen and oxygen atoms include: morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 2-methyl-2-piperidone Monocyclic saturated heterocycle; 4-methyl

Azole etc.

Azole, 2-methyliso

Azole, 3-Methyliso

Azole isoiso

Monocyclic unsaturated heterocyclic rings such as azoles; benzo

azoles, benziso

Azole, benzo

, Benzodi

Condensed bicyclic heterocycles such as alkanes and benzimidazolins;

(phenoxazine) and other condensed tricyclic heterocycles, etc.

等縮合三環系雜環等。 Heterocycles containing nitrogen atoms and sulfur atoms include monocyclic heterocycles such as thiazoles such as 3-methylthiazole and 2,4-dimethylthiazole; condensed bicyclic heterocycles such as benzothiazole;

Condensation tricyclic heterocyclic rings etc.

The above-mentioned heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, for example, tetrahydrofurylmethyl group and the like are mentioned.

Furthermore, the aforementioned heterocycle may be represented by the following formulae.

The aforementioned heterocyclic group may also be a heterocyclic group formed by bonding two or more 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. The ring structure having two or more rings includes, for example, a structure of the following formula.

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

The heterocyclic group represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may have a substituent. Examples of such substituents include those that may have the same substituents that the aliphatic hydrocarbon groups represented by R ^N1 and R ^N2 and the hydrocarbon groups represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² may have. Also, when the aforementioned heterocyclic ring system contains a nitrogen atom as its constituent element, the nitrogen atom may be bonded to the aforementioned hydrocarbon group as a substituent.

Preferable examples of this substituent include preferred substituents that may be present with aliphatic hydrocarbon groups represented by R ^N1 and R ^N2 , and hydrocarbon groups represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ , and R ¹⁰² who are the same.

The heterocyclic group having a substituent represented by R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ and R ¹⁰² includes a heterocyclic group having a monovalent or divalent substituent, preferably a heterocyclic group having a group s1 The heterocyclic group having a substituent of the group s2 is more preferably a heterocyclic group having a substituent of the group s2.

The substituents (first substituents) that the hydrocarbon group or heterocyclic group may have may be one or more, and the two or more substituents are independent from each other and may be the same or different. Furthermore, another substituent (second substituent) may be bonded to the hydrocarbon group contained in the aforementioned first substituent. The second substituent can be selected from the same groups as the first substituent.

^In the following, -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 , -SO ₃ M, -CO ₂ M.

Examples of -CO-R ¹⁰² include formyl; acetyl, propionyl, butyryl, 2,2-dimethylacryl, pentyl, hexyl, (2-ethyl) Hexyl, heptyl, octyl, nonyl, decanyl, undecyl, dodecyl, hexacyl, benzoyl, etc., and the groups represented by the above formulas are A hydrocarbon group with 1 to 40 carbons (preferably 1 to 20 carbons) or a derivative thereof (such as 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 A carbonyl group derived from an alkylsulfamoyl group (preferably an octylsulfamoyl group), etc.), preferably a carbonyl group bonded to a hydrocarbon group with a carbon number of 1 to 10 (the carbonyl group is set as In the case of an acyl group, the carbon number is 2 to 41), etc. Preferably, a carbonyl group bonded to a hydrocarbon group with a carbon number of 1 to 11 (more preferably a carbon number of 1 to 10) or a derivative thereof (when the carbonyl group is an alkyl group, the carbon number is preferred) 2 to 12) etc.

Examples of -COO-R ¹⁰¹ include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tertiary butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl)hexyloxycarbonyl , heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenoxycarbonyl, eicosyloxycarbonyl, etc., and the groups represented by the above formula, etc. The oxycarbonyl group bonded with a hydrocarbon group having 1 to 40 carbons (preferably 1 to 20 carbons), preferably a hydrocarbon group bonded with 1 to 10 carbons or a derivative thereof (such as carboxyl, sulfo Oxygen of acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group with 1 to 10 carbons (preferably octylsulfamoyl group), etc.) Carbonyl etc.

Preferable examples include an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded.

Examples of -OCO-R ¹⁰² include formyloxy; acetyloxy, propionyloxy, butyryloxy, 2,2-dimethylacryloxy, pentyloxy, hexyloxy Oxygen, (2-Ethyl)hexyloxy, Heptyloxy, Octyloxy, Nonyloxy, Decyloxy, Undecyloxy, Dodecyloxy, Eicosyloxy Oxygen group, benzoyloxyl group, etc., and the group represented by the above formula, etc., are bonded to the carbonyl group of the hydrocarbon group with 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms). Examples include hydrocarbon groups with carbon numbers from 1 to 10 or derivatives thereof (such as carboxyl, sulfonic acid, nitro, hydroxyl, halogen (preferably chlorine), alkylsulfamoyl (preferably (octylsulfamoyl) and other derivatized groups) carbonyloxy group (when the carbonyloxy group is an acyloxy group, the number of carbon atoms is 2 to 41), etc., preferably bonded with 1 carbon number A carbonyloxy group of a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof (when the carbonyloxy group is an acyloxy group, the carbon number is preferably 2 to 12 carbon atoms), etc.

As -COCO-R ¹⁰² , methyl oxalyl, ethyl oxalyl, propyl oxalyl, butyl oxalyl, pentyl oxalyl, hexyl oxalyl, (2-ethyl oxalyl) Base) hexyl oxalyl, heptyl oxalyl, octyl oxalyl, nonyl oxalyl, decyl oxalyl, undecyl oxalyl, dodecyl oxalyl, eicosyl oxalyl oxalyl group, cyclopentyl oxalyl group, cyclohexyl oxalyl group, phenyl oxalyl group, p-tolyl oxalyl group, etc., and the groups represented by the above formulas have a carbon number of 1 to 40 (preferably carbon number 1 to 20) hydrocarbon group or its derivation group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group with carbon number 1 to 10 (preferably Octylsulfamoyl) and other derivatives such as oxalyl, etc.

As -OR ¹⁰² , hydroxyl can be mentioned; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, second butoxy, third butoxy, pentyloxy Oxy, 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-dicyanobenzene Oxygen, 2,3-dicyanophenoxy, 2,4-dicyanophenoxy, 2,5-dicyanophenoxy, 2,6-dicyanophenoxy, 3,4 -Dicyanophenoxy, 3,5-dicyanophenoxy, 4-methoxyphenoxy, 2-methoxyphenoxy, 3-methoxyphenoxy, 4-ethoxy phenoxy, 2-ethoxyphenoxy, 3-ethoxyphenoxy, etc., and the groups represented by the above formulas are bonded with 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) Hydrocarbyl or its derivation group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), carbon number 1 to 10 alkyl sulfamoyl group (preferably octyl sulfamoyl group) The oxy group of the group) derivatized by (group) etc., Preferably, the oxy group etc. which bonded the hydrocarbon group of 1-10 carbons are mentioned.

Preferable examples include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded.

Examples of -SO ₂ -R ¹⁰¹ include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2- Ethyl) Hexylsulfonyl, Heptylsulfonyl, Octylsulfonyl, Nonylsulfonyl, Decylsulfonyl, Undecylsulfonyl, Dodecylsulfonyl, Eicosylsulfonyl Acyl group, phenylsulfonyl group, p-tolylsulfonyl group, etc., and the groups represented by the above formulas are bonded with hydrocarbon groups with 1 to 40 carbons (preferably 1 to 20 carbons) or derivatives thereof ( For example, it is derivatized by carboxyl, sulfonic acid, nitro, hydroxyl, halogen (preferably chlorine atom), alkyl sulfamoyl group with 1 to 10 carbons (preferably octyl sulfamoyl group), etc. A sulfonyl group, etc., preferably a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded.

Examples of -SO ₂ N(R ¹⁰² ) ₂ include sulfamoyl; N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-iso Propyl sulfamoyl, N-butyl sulfamoyl, N-isobutyl sulfamoyl, N-second butyl sulfamoyl, N- tertiary butyl sulfamoyl, N- Amylsulfamoyl, N-(1-ethylpropyl)sulfamoyl, N-hexylsulfamoyl, N-(2-ethyl)hexylsulfamoyl, N-heptylsulfamoyl Acyl group, N-octyl sulfamoyl group, N-nonyl sulfamoyl group, N-decyl sulfamoyl group, N-undecyl sulfamoyl group, N-dodecyl sulfamoyl group, N-eicosylsulfamoyl group, N-phenylsulfamoyl group, etc., and the group represented by the above formula, etc. are derived by a hydrocarbon group with 1 to 40 carbons (preferably 1 to 20 carbons) or derivatives thereof Cyl group (for example by carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), carbon number 1 to 10 alkyl sulfamoyl group (preferably octyl sulfamoyl group) etc. Chemical base) substituted sulfamoyl group, etc.; N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group , N,N-propylmethylsulfamoyl, N,N-dipropylsulfamoyl, N,N-isopropylmethylsulfamoyl, N,N-diisopropylsulfamoyl Acyl group, N,N-tert-butylmethylsulfamoyl group, N,N-diisobutylsulfamoyl group, N,N-disecond-butylsulfamoyl group, N,N-di-tertiary Butylsulfamoyl, N,N-butylmethylsulfamoyl, N,N-dibutylsulfamoyl, N,N-dipentylsulfamoyl, N,N-di(1- Ethylpropyl)sulfamoyl, N,N-dihexylsulfamoyl, N,N-di(2-ethyl)hexylsulfamoyl, N,N-diheptylsulfamoyl, N,N-octylmethylsulfamoyl, N,N-dioctylsulfamoyl, N,N-dinonylsulfamoyl, N,N-decylmethylsulfamoyl, N,N-undecylmethylsulfamoyl, N,N-dodecylmethylsulfamoyl, N,N-eicosylmethylsulfamoyl, N,N-phenylmethyl Aminosulfonyl group, N,N-diphenylsulfamoyl group, etc., and the group represented by the above formula are derivatized by two hydrocarbon groups with 1 to 40 carbons (preferably 1 to 20 carbons) group (for example, derivatized by carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group with 1 to 10 carbons (preferably octylsulfamoyl group), etc. A sulfamoyl group substituted with a sulfamoyl group etc., preferably a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbons or derivatives thereof.

Examples of -CON(R ¹⁰² ) ₂ include carbamoyl; N-methyl carbamoyl, N-ethyl carbamoyl, N-propyl carbamoyl, N -Isopropylaminoformyl, N-butylaminoformyl, N-isobutylaminoformyl, N-second butylaminoformyl, N-tert-butylamine Aminoformyl, N-pentylaminoformyl, N-(1-ethylpropyl)aminoformyl, N-hexylaminoformyl, N-(2-ethyl)hexylamine Aminoformyl, N-heptylaminoformyl, N-octylaminoformyl, N-nonylaminoformyl, N-decylaminoformyl, N-undecyl Aminoformyl group, N-dodecylaminoformyl group, N-eicosylaminoformyl group, N-phenylaminoformyl group, etc., and the groups represented by the above formulas are replaced by 1 carbon A hydrocarbon group with a number of 1 to 40 (preferably a carbon number of 1 to 20) or a derivative thereof (such as a carboxyl group, a sulfonic acid group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a carbon number of 1 to 10 Alkylaminosulfonyl (preferably octylaminosulfonyl) and other derivatives) substituted aminoformyl, etc.; N,N-dimethylaminoformyl, N,N -Ethylmethylaminoformyl, N,N-Diethylaminoformyl, N,N-Propylmethylaminoformyl, N,N-Dipropylaminoformyl , N,N-isopropylmethylaminoformyl, N,N-diisopropylaminoformyl, N,N-tert-butylmethylaminoformyl, N,N-diiso Butylaminoformyl, N,N-disecond-butylaminoformyl, N,N-di-tert-butylaminoformyl, N,N-butylmethylaminoformyl, N,N-dibutylaminoformyl, N,N-butyloctylaminoformyl, N,N-dipentylaminoformyl, N,N-di(1-ethyl Propyl)aminoformyl, N,N-dihexylaminoformyl, N,N-di(2-ethyl)hexylaminoformyl, N,N-diheptylaminoformyl N,N-octylaminoformyl, N,N-dioctylaminoformyl, N,N-dinonylaminoformyl, N,N-decylaminoformyl Aminoformyl, N,N-undecylmethylaminoformyl, N,N-dodecylmethylaminoformyl, N,N-eicosylmethylaminoformyl , N,N-phenylmethylaminoformyl, N,N-diphenylaminoformyl, etc., and the group represented by the above formula is replaced by 2 carbon numbers of 1 to 40 (preferably carbon number 1 to 20) hydrocarbon group or its derivation group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group with carbon number 1 to 10 (preferably octylsulfamoyl) and other derivatives) substituted carbamoyl, etc., preferably amines substituted by one or two hydrocarbon groups with 1 to 10 carbons or derivatives thereof methacryl, etc.

Examples of -N(R ¹⁰² ) ₂ include amino groups; N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamine Base, N-isobutylamino group, N-second butylamino group, N-tertiary butylamino group, N-pentylamino group, N-hexylamino group, N-(2-ethyl)hexyl Amino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-two Decylamino group, N-phenylamino group, etc., and the groups represented by the above formulas are replaced by a hydrocarbon group with 1 to 40 carbons (preferably 1 to 20 carbons) or a derivative thereof (for example, by carboxyl, Sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkyl sulfamoyl group with 1 to 10 carbons (preferably octyl sulfamoyl group) and other derivatized groups) Amino groups, etc.; N,N-dimethylamino, N,N-ethylmethylamino, N,N-diethylamino, N,N-propylmethylamino, N,N -Dipropylamino, N,N-isopropylmethylamino, N,N-diisopropylamino, N,N-tert-butylmethylamino, N,N-diisobutylamine group, N,N-disecond butylamino group, N,N-ditertiary butylamino group, N,N-butylmethylamino group, N,N-dibutylamino group, N,N-dibutylamino group Amylamino, N,N-di(1-ethylpropyl)amino, N,N-dihexylamino, N,N-di(2-ethyl)hexylamino, N,N-di Heptylamino, N,N-dioctylamino, N,N-dinonylamino, N,N-decylmethylamino, N,N-undecylmethylamino, N, N-dodecylmethylamino group, N,N-eicosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc., and groups represented by the above formula etc. by two hydrocarbon groups with 1 to 40 carbons (preferably 1 to 20 carbons) or their derivatives (such as carboxyl, sulfonic acid, nitro, hydroxyl, halogen (preferably chlorine), carbon 1 to 10 alkyl sulfamoyl group (preferably octyl sulfamoyl group) and other derivatives) substituted amino groups, etc.; preferably 1 or 2 carbon number 1 Hydrocarbyl to 10 or amino groups substituted by derivatized groups, etc.

Examples of -NHCO-R ¹⁰² include formylamine; acetylamino, propionylamine, butyrylamine, 2,2-dimethylacrylamine, pentylamine Base, Caproylamine, (2-Ethyl)caproylamine, Heptylamino, Octylamino, Nonylamine, Decacylamino, Undecylamino, Decacylamino Diacylamino group, eicosylamino group, benzoylamino group, etc., and groups represented by the above formulas are bonded to hydrocarbon groups with 1 to 40 carbons (preferably 1 to 20 carbons) or Its derivatization group (such as carboxyl group, sulfonic acid group, nitro group, hydroxyl group, halogen (preferably chlorine atom), carbon number 1 to 10 alkyl sulfamoyl group (preferably octyl sulfamoyl group) Derivatized groups such as) carbonylamino group (when the carbonylamino group is an amido group, the carbon number is 1 to 40), etc., preferably a hydrocarbon group with 1 to 10 carbon atoms bonded A carbonylamino group or a derivative thereof (when the carbonylamino group is an alkylamino group, the number of carbon atoms is preferably 1 to 10), etc.

Examples of -NHCON(R ¹⁰² ) ₂ include the groups mentioned above and the like.

Examples of -NHCOOR ¹⁰² include the groups mentioned above and the like.

Examples of -OCON(R ¹⁰² ) ₂ include the above-mentioned groups and the like.

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

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 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 (first substituent) may be One or two or more substituents are independent of each other and may be the same or different.

In addition, another substituent (second substituent) may be bonded to the hydrocarbon group contained in the first substituent described above. The second substituent can be selected from the same groups as the first substituent.

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

R ^N1 and R ^N2 are aliphatic hydrocarbon groups, aralkyl groups, (cycloalkyl) alkyl groups, aliphatic hydrocarbon groups substituted by hydroxyl groups, and oxy groups substituted by hydrocarbon groups with 1 to 20 carbon atoms bonded to one side Aliphatic hydrocarbon group is preferably straight chain or branched chain alkyl, straight chain or branched chain alkenyl, cycloalkyl, aralkyl, (cycloalkyl) alkyl, straight chain substituted by hydroxyl A chain or branched chain alkyl group, and a straight chain or branched chain alkyl group substituted with an alkoxy group are preferred.

R ^N1 and R ^N2 may be the same or different.

R ^N3 is preferably an aliphatic hydrocarbon group, preferably a straight-chain or branched-chain alkyl group, and more preferably a straight-chain alkyl group.

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

Ag- in the compound represented by the formula (I) represents an anion having a ^g valency. g represents an integer of 1 to 14, preferably represents an integer of 1 to 10, more preferably represents an integer of 1 to 8, more preferably represents an integer of 1 to 6, particularly preferably represents an integer of 1 to 4.

Well-known anions are mentioned as ^Ag- . Specific examples of ^Ag- include halide ions such as fluoride ions, chloride ions, bromide ions, and iodide ions; OH ^- ; CN ^- ; NO ₃ ^- ; NO ₂ ^- ; ClO ^- ; ClO ₂ ^{- ;} _ClO3 ^{- ;} _ClO4 ^- ; MnO ₄ ^- ; _{CH 3} CO ₂ ^{- ,} C ₆ H ₅ CO ₂ ^- _; 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- _; ^- ; Cr ₂ O ₇ ^2- ; (COO) ₂ ^2- ; ^HPO ₄ ^2- ; [Zn(OH) ₄ ] ^2- ; [Zn(CN _{) 4} ] ^2- _; ^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 ^- an alkoxyl ion with a carbon number of 1 to 20, C ₆ H ₅ O ^- an aryloxyl ion with a carbon number of 6 to 20; fluorine-containing anions; will be selected from tungsten, molybdenum, silicon and phosphorus At least one element constituting the group, an anion containing oxygen as an essential element, and the like.

In terms of heat resistance improvement and sublimation reduction, ^Ag- is an anion containing fluorine-containing anions, or at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements Preferably, at least one element selected from the group consisting of tungsten and phosphorus, and an anion containing oxygen as an essential element, or an anion containing fluorine is preferably selected from the group consisting of tungsten and phosphorus An anion containing at least one element and oxygen as an essential element is more preferable.

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

[In formula (III), W ³ and W ⁴ represent independently a fluorine atom or a fluorinated alkyl group with 1 to 4 carbons, or W ³ and W ⁴ together represent a fluorinated alkyl group with 1 to 4 carbons two bases],

[In formula (IV), W ⁵ to W ⁷ are each independently representing a fluorine atom or a fluorinated alkyl group with 1 to 4 carbons],

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

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

In formulas (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 , etc.

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

The anion represented by formula (III) (hereinafter referred to as "anion (III)") includes anions represented by formula (III-1) to formula (III-6) respectively (hereinafter referred to as "anion (III)"). In the case of "anion (III-1)" to "anion (III-6)").

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

The anion represented by formula (V) (hereinafter referred to as "anion (V)") may include anions represented by formula (V-1) to formula (V-4) (hereinafter referred to as "Anion (V-1)" to "Anion (V-4)").

The anion represented by formula (VI) (hereinafter referred to as "anion (VI)") may include anions represented by formula (VI-1) to formula (VI-4) (hereinafter referred to as "Anion (VI-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, with CF ₃ CO ₂ ^- , anion (III-1), anion (III-2), anion (III-6), anion (IV-1), anion (V-1), anion (VI-1) , anion (VI-2) and anion (VI-3) are preferred, and CF ₃ CO ₂ ^- , anion (III-2), anion (IV-1) and anion (VI-1) are preferred.

Examples of the anion include anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements. The anion of heteropolymeric acid or homopolymeric acid containing tungsten as an essential element is preferable, and the anion of phosphotungstic acid, silicotungstic acid, and tungsten homopolymeric acid is more preferable. Such anions contribute to improvement of heat resistance when used, for example, in a coloring compound represented by formula (I) having a fluorine-containing anion (preferably anion (VI-1)) and performing anion exchange.

This kind of anion of heteropoly acid or isopoly acid containing tungsten as an essential element, such as Keggin type (Keggin type) phosphotungstic acid ion α-[PW ₁₂ O ₄₀ ] ^{3 -} , Dawson type (Dawson type) phosphotungstic acid ion α-[P ₂ W ₁₈ O ₆₂ ] ^6- , β-[P ₂ W ₁₈ O ₆₂ ] ^6- , Cojin type silicotungstic acid ion 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-[SiW1 ₁ O ₃₉ ] ^8- , β-[SiW ₁₁ O ₃₉ ] ^8- , [W ₆ O ₁₉ ] ² -, [W ₁₀ O ₃₂ ] ^4- , WO ₄ ^2- Wait. Among them, the Kojin-type phosphotungstic acid ion α-[PW ₁₂ O ₄₀ ] ^3- is preferred.

Compound (I) is preferably a compound represented by formula (I-B) (hereinafter, sometimes referred to as compound (I-B)). When the compound (I) is the compound (I-B), it has excellent heat resistance.

[In formula (IB), R ^N1 , R ^N2 , R ^N3 , R ¹ to R ⁸ , R ¹⁰¹ , R ¹⁰² and M represent the same meanings as above.

B ^h- represents an h-valent anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements.

h represents an integer from 1 to 14]

In formula (IB), examples of B ^h- include the same anions having a g-valence of tungsten, molybdenum, or the like already mentioned as A ^g- in formula (I).

In formula (IB), preferred B ^h- can be mentioned as ^Ag- in formula (I) and at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus , and g-valent anions containing oxygen as an essential element are preferably the same.

Examples of the compound (I) include the compounds shown in Tables 1 to 10 or alkali metal salts thereof.

Also, in Tables 1 to 10, "Me" means a methyl group, "Et" means an ethyl group, "Bu" means a butyl group, "TBu" means a tertiary butyl group, "Hex" means a hexyl group, "Oct" means octyl, "2EH" means 2-ethylhexyl, "CHM" means cyclohexylmethyl, "CH" means cyclohexyl, "PH" means phenyl, "BZ" means benzene Methyl, "NPR" means propyl, "IPR" means isopropyl, "IBu" means isobutyl, "EOE" means -CH ₂ CH ₂ OCH ₂ CH ₃ , "ALL" means ene Propyl, "HYE" means 2-hydroxyethyl, "COM" means -CO-CH ₃ , "COE" means -COO-CH ₂ CH ₃ , "OCM" means -OCO-CH ₃ , "OME" stands for -O-CH ₃ , "SOT" stands for tosyl, "SNH" stands for -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""NOT" means -N((CH ₂ ) _{7 CH 3 ) 2 , " NCO} " means -NHCO((CH ₂ ) ₄ CH ₃ ), "F" means fluorine atom , "Cl" means chlorine atom, "Br" means bromine atom, "CN" means cyano group, "NO2" means nitro group, "SUA" means -SO ₃ H, "CBA" means -CO ₂ H, "CHO" means -CHO, "OCH" means -OCOH, "OH" means -OH, "SFM" means -SO ₂ NH ₂ , "CBM" means -CONH ₂ , "NH2" means -NH ₂ , "NCH" means -NHCOH, "III-1" to "III-6" means anion (III-1) to anion (III-6), "IV-1" means anion ( IV-1), "V-1" to "V-4" means anion (V-1) to anion (V-4), "VI-1" to "VI-4" means anion (VI-1 ) to the anion (VI-4).

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

From the viewpoint of easy synthesis, compounds (I-1) to compounds (I-312) are preferred, compounds (I-1) to compounds (I-156) are preferred, compounds (I-1 ) to compound (I-24) are more preferable, and compound (I-13) to compound (I-24) are especially preferable.

Among them, compound (I) of the present invention is particularly preferably compound (I-14).

Compound (I) of the present invention can be obtained by making a compound represented by formula (II) (hereinafter referred to as compound (II)), and a compound represented by formula (II-1) (hereinafter referred to as compound ( The case of II-1)) can be obtained by reacting, and can also be obtained by pairing a compound containing at least one element selected from the group consisting of tungsten, silicon, and phosphorus, and oxygen as an essential element. The compound is further reacted to obtain.

[In formula (II) and formula (II-1), R ¹ to R ⁸ , R ^N1 , R ^N2 , R ^N3 and g represent the same meanings as above, and A' represents that g electrons are donated to the above-mentioned A ^g- By]

The compound represented by formula (II-1) includes an alkylating agent. Examples of the alkylating agent include: preferably a halogenated alkyl group having 1 to 10 carbon atoms, more preferably a halogenated alkyl group having 1 to 3 carbon atoms (methane chloride, methyl bromide, or methyl iodide, etc.) ; preferably carbon number 2 to 10, more preferably carbon number 2 to 6, and more preferably carbon number 2 to 4 dialkyl carbonate (dimethyl carbonate or diethyl carbonate, etc.); preferably Dialkyl sulfuric acid (dimethyl sulfuric acid or diethyl sulfuric acid, etc.) with 1 to 10 carbons, more preferably 1 to 6 carbons, and more preferably 1 to 4 carbons; preferably 2 to 2 carbons 10. Alkanesulfonate alkyl esters (methyl methanesulfonate, ethyl ethanesulfonate, ethyl methanesulfonate, methyl ethanesulfonate, more preferably carbon number 2 to 6, more preferably carbon number 2 to 4) , methyl triflate, ethyl triflate, etc.).

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

The amount of the alkylating agent to be used is preferably not less than 1 mol and not more than 20 mol, more preferably not less than 1 mol and not more than 10 mol, relative to 1 mol of compound (II).

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

In terms of yield, the reaction is preferably carried out in an organic solvent. Examples of organic solvents include aromatic hydrocarbon solvents such as toluene and xylene; aliphatic hydrocarbon solvents such as hexane; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, methylene chloride, and chloroform; methanol, ethanol, and isopropanol nitrobenzene and other nitro hydrocarbon solvents; acetone, methyl isobutyl ketone and other ketone solvents; ethyl acetate and other ester solvents; diethyl ether and tetrahydrofuran and other ether solvents; acetonitrile and other nitrile solvents; N, Amide solvents such as N-dimethylformamide, N,N-dimethylacetamide, 1-methyl-2-pyrrolidone, etc., preferably aromatic hydrocarbon solvents, toluene and xylene better. The usage-amount of an organic solvent is 1 mass part or more and 300 mass parts or less with respect to 1 mass part of compound (II), Preferably it is 1 mass part or more and 100 mass parts or less.

The method for obtaining the compound from the reaction mixture is not particularly limited, and various well-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. Purification can also be carried out by a method of further using a solvent to perform recrystallization or using silica gel column chromatography if necessary. The obtained compound is, for example, a compound represented by formula (I).

Next, a method of exchanging the anion of the compound represented by the formula (I) can also be used. As this method, adding at least one element selected from the group consisting of tungsten, silicon, and phosphorus, and oxygen A method, etc., of a compound or the like contained as an essential element.

A compound containing at least one element selected from the group consisting of tungsten, silicon, and phosphorus, and oxygen as an essential element (in this specification, hereinafter also referred to as an anion exchanger) can be obtained by a well-known and commonly used method. to manufacture, but commercially available products can also be used as they are. Such compounds include, for example, corresponding heterotropic polymeric acid salts, homotropic polymeric acid salts, or silicates, phosphates, etc., and can also be phosphotungstic acid, silicotungstic acid, phosphomolybdic acid, and silicomolybdic acid.

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

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

In terms of yield, the reaction is preferably carried out in water, an organic solvent or a mixture thereof. Examples of organic solvents include aromatic hydrocarbon solvents such as toluene and xylene; aliphatic hydrocarbon solvents such as hexane; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, methylene chloride, and chloroform; methanol, ethanol, and isopropanol nitrobenzene and other nitro hydrocarbon solvents; acetone, methyl isobutyl ketone and other ketone solvents; ethyl acetate and other ester solvents; diethyl ether and tetrahydrofuran and other ether solvents; acetonitrile and other nitrile solvents; N, Amide solvents such as N-dimethylformamide, N,N-dimethylacetamide, 1-methyl-2-pyrrolidone, etc. The solvents in which the aforementioned reaction can be carried out include water, alcohol solvents, ketone solvents, ether solvents, nitrile solvents, amide solvents, or mixtures thereof, preferably water, alcohol solvents, ketone solvents, nitrile solvents, and amide solvents. An amine solvent or a mixture thereof, more preferably water, an alcohol solvent or a mixture thereof, particularly preferably water, methanol or a mixture thereof.

The amount of the organic solvent used is preferably from 1 part by mass to 1000 parts by mass, more preferably from 10 parts by mass to 500 parts by mass, relative to 1 part by mass of the compound represented by formula (I).

According to this method, when the anion of the compound represented by the formula (I) is exchanged, it can become a compound suitable for improving the heat resistance and reducing the sublimation property.

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

[In formula (VII) and formula (VIII), R ¹ to R ³ , R ⁵ to R ⁸ , R ^N1 and R ^N2 represent the same meaning as above, and R ⁹ represents an alkyl group with 1 to 20 carbons]

The alkyl group with 1 to 20 carbons represented by ^R9 can include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, second butyl, third butyl, etc., preferably Examples thereof include alkyl groups having 1 to 6 carbon atoms.

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

Compound (VIII) is usually used in an amount of 1 to 10 mol, preferably 1 to 4 mol, relative to 1 mol of compound (II).

The reaction between compound (VII) and compound (VIII) is usually carried out in the presence of a solvent, and examples of the solvent include nitrile solvents such as acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, etc. Alcohol solvents such as alcohol and 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 hydrocarbons such as methylene chloride and chloroform The solvent, and amide solvents such as N,N-dimethylformaldehyde and N-methylpyrrolidone, are preferably nitrile solvents, alcohol solvents, and aromatic hydrocarbon solvents, and preferably include acetonitrile, methanol, and toluene. The amount used is usually 1 to 100 parts by mass relative to 1 part by mass 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, the compound (II) can be taken out, for example, by mixing the obtained reaction mixture with a solvent in which the compound (II) is not easily soluble, and filtering. If necessary, the method of recrystallization using a solvent or the purification using silica gel column chromatography may also be used.

Compound (VII) can be obtained by making a compound represented by formula (IX) (hereinafter referred to as compound (IX)) and a compound represented by formula (X) (hereinafter referred to as compound (X)) React in a solvent to manufacture.

[In formula (IX) and formula (X), R ⁵ to R ⁹ represent the same meaning as above, and R ¹⁰ represents an alkyl group with 1 to 4 carbons]

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

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

As a solvent, alcohol solvents, such as methanol, are mentioned, and the usage-amount is 1-200 mass parts normally with respect to 1 mass part of 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, the compound (VII) can be taken out by filtration, for example, after mixing the reaction mixture with water or methanol if necessary. In addition, after the reaction is completed, for example, the reaction mixture can be mixed with water if necessary, and the compound (VII) can be extracted by using a water-insoluble organic solvent such as ethyl acetate and concentrating the obtained organic layer. take out. If necessary, it may further be purified by recrystallization using a solvent or by silica gel column chromatography.

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

The coloring composition of the present invention may contain two or more compounds (I). The compound (I) can be used as a coloring agent (A) together with dyes or pigments (coloring agent A1) other than a compound (I) as needed.

The coloring composition of the present invention contains at least one of the aforementioned compound (1), resin (B) and solvent (E), or contains both of the aforementioned compound (1), resin (B) and solvent (E). good.

<Resin (B)>

The resin (B) is preferably an alkali-soluble resin having at least one monomer (a) (hereinafter referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides. case) polymers of structural units are preferred.

The resin (B) is composed of a structural unit derived from a monomer (b) (hereinafter referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, and Copolymers of other structural units are preferred.

As other structural units, monomers (c) derived from monomers (a) copolymerizable (but different from monomers (a) and monomers (b). Hereinafter referred to as "(c) )" in the case of), a structural unit having an ethylenically unsaturated bond, etc.

Examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, ortho-, meta-, and p-vinylbenzoic acid; maleic acid, fumaric acid, Citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3 , unsaturated dicarboxylic acids such as 6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid and 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 Bicyclic unsaturated compounds containing carboxyl groups, such as 2-ene and 5-carboxyethylbicyclo[2.2.1]hept-2-ene; anhydrides of the above-mentioned unsaturated dicarboxylic acids, excluding fumaric acid and mesaconic acid, etc. Carboxylic acid anhydrides; polycarboxylic acids with more than two valences, such as succinic acid mono[2-(meth)acryloxyethyl] and phthalic acid mono[2-(meth)acryloxyethyl], etc. Saturated mono[(meth)acryloxyalkyl] esters; unsaturated acrylates such as α-(hydroxymethyl)acrylic acid containing hydroxyl and carboxyl groups in the same molecule, etc.

Among these, acrylic acid, methacrylic acid, and maleic anhydride are preferable in terms of copolymerization reactivity and solubility of the resulting resin in 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 ethylenically unsaturated bonded polymeric compounds. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloxy group.

Examples of (b) include monomers (b1) having an oxirane group and an ethylenically unsaturated bond (hereinafter referred to as "(b1)"), monomers having an oxetane group and Monomer (b2) having an ethylenically unsaturated bond (hereinafter referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter referred to as "(b3) ” situation) and so on.

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

(b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond. Examples of (b1-1) specifically include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethyl (meth)acrylate Glycidyl ester, glycidyl vinyl ether, vinylbenzyl glycidyl ether, α-methylvinylbenzyl glycidyl ether, 2,3-bis(glycidoxypropoxy Methyl)styrene, 2,4-bis(glycidoxymethyl)styrene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxypropoxy methyl) styrene, 2,3,4-paraffin (glycidoxymethyl) styrene, 2,3,5-paraffin (glycidoxymethyl) styrene, 2,3,6 -Phenol(glycidoxymethyl)styrene, 3,4,5-paraffin(glycidoxymethyl)styrene and 2,4,6-paraffin(glycidoxymethyl)benzene vinyl etc.

Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, CELLOXIDE (registered trademark) 2000; manufactured by Daicel Co., Ltd. ), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, CYCLOMER (registered trademark) A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth)acrylate Esters (eg, CYCLOMER (registered trademark) M100; manufactured by Daicel Co., Ltd.), compounds represented by formula (BI), compounds represented by formula (BII), and the like.

[In the formulas (BI) and (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 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.

* represents the connection key with O].

The compound represented by formula (BI) can include compounds represented by any one of formula (BI-1) to formula (BI-15), preferably formula (BI-1), formula (BI- 3), the compound 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 formula (BII) may include compounds represented by any one of formula (BII-1) to formula (BII-15), preferably formula (BII-1), formula (BII-3 ), formula (BII-5), formula (BII-7), formula (BII-9) and formula (BII-11) to the compound represented by 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 the formula (BI) and the compound represented by the formula (BII) may be used alone, or the compound represented by the formula (BI) and the compound represented by the formula (BII) may be used in combination. When these are used together, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5 on a molar basis, preferably 10:90 to 90: 10, preferably 20:80 to 80:20.

Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, second-butyl (meth)acrylate, (meth)acrylic acid Tertiary butyl ester, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate Tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, Tricyclo[5.2.1.0 ^2,6 ]decane-9-yl (meth)acrylate, (meth)acrylate base) tricyclo[5.2.1.0 ^2,6 ]decen-8-yl acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-9-yl (meth)acrylate, di(meth)acrylate Cyclopentyloxyethyl ester, Isocamphoryl (meth)acrylate, Adamantyl (meth)acrylate, Allyl (meth)acrylate, Propargyl (meth)acrylate, Benzene (meth)acrylate (meth)acrylic acid esters such as naphthyl (meth)acrylate and benzyl (meth)acrylate; 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate containing hydroxyl groups (meth)acrylic esters; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate; bicyclo[2.2.1]hept-2-ene , 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5- Hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept- 2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo [2.2.1] Hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1] Hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy- 5-Ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1 ]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(third Butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; N-phenylbutadiene Diene imide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzine Ester, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-cis-butyl Dicarbonyl amides such as olefinic imide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridyl)maleimide Imine derivatives; vinyl-containing aromatic compounds such as styrene, α-methylstyrene, vinyltoluene and p-methoxystyrene; vinyl-containing nitriles such as (meth)acrylonitrile; vinyl chloride and Halogenated hydrocarbons such as vinylidene chloride; vinyl-containing amides such as (meth)acrylamide; esters such as vinyl acetate; 1,3-butadiene, isoprene and 2,3-dimethyl- Dienes such as 1,3-butadiene, etc.

Among these, in terms of copolymerization reactivity and heat resistance, styrene, vinyl toluene, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, Tricyclo[5.2.1.0 ^2,6 ]decane-9-yl (meth)acrylate, Tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate, (methyl) Tricyclo[5.2.1.0 ^2,6 ]decen-9-yl acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide Preferred are alkene imide, bicyclo[2.2.1]hept-2-ene, and benzyl (meth)acrylate.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth)acryloyl group. The resin having such a structural unit can be added to a monomer having an ethylenically unsaturated bond in a group derived from (a), ( The polymer of the structural unit of b) is obtained.

Examples of such structural units include: a structural unit in which glycidyl (meth)acrylate is added to a (meth)acrylic acid unit; 2-hydroxyethyl (meth)acrylate is added to cis-butyl Structural units formed by alkene anhydride units, and structural units formed by adding (meth)acrylic acid to glycidyl (meth)acrylate units, etc. Moreover, when these structural units have a hydroxyl group, the structural unit which further added carboxylic anhydride can also be mentioned as a structural unit which has an ethylenically unsaturated bond.

The polymer having the structural unit derived from (a) can be produced, for example, by polymerizing monomers constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator, solvent, and the like are not particularly limited, and those commonly used in this field can be used. For example, examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.), The organic peroxide (benzoyl peroxide, etc.) may be used as a solvent as long as it dissolves each monomer.

In addition, the obtained polymer may be used as it is after the reaction, may be used as a concentrated or diluted solution, or may be taken out as a solid (powder) by reprecipitation or the like.

Reaction catalysts (for example, ginseng(dimethylaminomethyl)phenol, etc.), polymerization inhibitors (for example, hydroquinone, etc.) and the like of carboxylic acids, carboxylic acid anhydrides, and cyclic ethers can also be used as needed.

Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6- Tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride and 5,6-dicarboxybicyclo[2.2.1]hept-2 -Alkenic anhydride, etc.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxy (meth)acrylate Tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, (meth)acrylic acid copolymer, base) glycidyl acrylate/styrene/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/ N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylcis Butenediimide/2-Hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylate /vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/tricyclo[5.2.1.0 ^2,6 ]decenyl (meth)acrylate/(methyl) Acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloxymethyloxetane/(meth)acrylic acid/styrene copolymer, Benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer, Japanese Patent Application Laid-Open No. 9-106071, Japanese Patent Application Laid-Open No. 2004-29518 and Japanese Patent Application Laid-Open No. 2004 - Resins, etc., described in the publications of Publication No. 361455.

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

Resin (B) can also combine two or more types. At this time, resin (B) is based on at least containing (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester/( Meth)acrylic acid 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, And one or more of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer is good.

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

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, 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, for example, by 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, more preferably 7 to 95% by mass, based on the total amount of solid content.

<Solvent (E)>

Examples of the solvent (E) include ester solvents (solvents containing -COO- and no -O- in the molecule), ether solvents (solvents containing -O- and no -COO- in the molecule), ether solvents Ester solvents (solvents that contain -COO- and -O- in the molecule), ketone solvents (solvents that contain -CO- and do not contain -COO- in the molecule), alcohol solvents (solvents that contain OH in the molecule and do not contain - O-, -CO- and -COO- solvents), aromatic hydrocarbon solvents, amide solvents and dimethyl sulfide, etc.

Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isopentyl formate ester, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetyl acetate, ethyl acetyl acetate, Cyclohexanol acetate and γ-butyrolactone, etc.

烷、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇甲基乙基醚、二乙二醇二丙醚、二乙二醇二丁醚、苯甲醚、苯乙醚及甲基苯甲醚等。 Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol 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-two

alkanes, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole and methyl anisole etc.

Examples of ether ester solvents include methyl methoxy acetate, ethyl methoxy acetate, butyl methoxy acetate, methyl ethoxy acetate, ethyl ethoxy acetate, 3-methoxy Methyl propionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxy Ethyl propionate, Propyl 2-methoxypropionate, Methyl 2-ethoxypropionate, Ethyl 2-ethoxypropionate, Methyl 2-methoxy-2-methylpropionate, 2-Ethoxy-2-methyl propionate ethyl ester, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether ethyl Ester, 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 ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2 -Pentanone, cyclopentanone, cyclohexanone, isophorone, etc.

Examples of alcohol solvents 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.

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

These solvents may use 2 or more types together.

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

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

Compound (I) may be subjected to rosin treatment, surface treatment using a derivative having an acidic group or a basic group, etc., grafting treatment on the surface of Compound (I) using a polymer compound, etc. Micronization treatment by sulfuric acid micronization method, etc., cleaning treatment using organic solvent, water, etc. to remove impurities, removal treatment by ion exchange method using ionic impurities, etc. The particle size of the compound (I) is preferably approximately uniform. The compound (I) is dispersed by adding a dispersant, and the compound (I) can be uniformly dispersed in the dispersion liquid.

Examples of the dispersant include surfactants and the like, and any of cationic, anionic, nonionic, and amphoteric surfactants may be used. Specifically, surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants are exemplified. These dispersants may be used alone or in combination of two or more. As a dispersant, when expressed by a trade name, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), SOLSPERSE (registered trademark) (manufactured by ZENECA Co., Ltd.), EFKA (registered trademark) (BASF Co., Ltd.), AJISPER (registered trademark) (Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (BYK-Chemie Co., Ltd.), BYK (registered trademark) ( BYK-Chemie (stock) system), etc.

When using a dispersant, the usage-amount of a dispersant (solid content) is 300 mass parts or less with respect to 100 mass parts of compound (I), Preferably it is 5 mass parts or more and 100 mass parts or less. When the usage-amount of a dispersing agent is the said range, it exists in the tendency for the coloring composition in a relatively uniform dispersion state to be obtained.

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

In the coloring composition, the content of the compound (I) is usually 1% by mass to 90% by mass, preferably 1% by mass to 80% by mass, with respect to the total amount of solids in the coloring composition, preferably Preferably, it is not less than 2% by mass and not more than 75% by mass.

The coloring composition of the present invention may contain coloring agents other than the compound (I) (hereinafter, sometimes referred to as coloring agent (A1)). The coloring agent (A1) may contain 1 type or 2 or more types of coloring agents. The coloring agent (A1) preferably contains a yellow coloring agent, an orange coloring agent or a red coloring agent.

<Coloring agent (A1)>

The coloring agent (A1) may be a dye or a pigment. As the dye, well-known dyes can be used, and dyes described in Color Index (published by The Society of Dyers and Colourists) and Dyeing Notes (Yorsensha) are exemplified. In terms of chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, dibenzopyran dyes, phthalocyanine dyes, and the like can be mentioned. These dyes can be used individually or in combination of 2 or more types.

Specifically, dyes with the following color index (C.I.) numbers are exemplified. 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. Reactive Yellow 2, 76, 116; , 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109 , 129, 132, 136, 138, 141; C.I. Disperse Yellow 51, 54, 76; C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99; C.I. Acid Orange 6, 7, 8, 10,12,26,50,51,52,56,62,63,64,74,75,94,95,107,108,149,162,169,173; C.I. Reactive Orange 16; C.I. Direct Orange 26 , 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; C.I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; C.I. Acid Red 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, 128, 132, 136, 139; C.I. Acid Blue 25, 27, 40, 45, 78, 80, 112; C.I. Direct Blue 40; C.I. Disperse Blue 1, 14, 56, 60; C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33; C.I. acid green 3, 5, 9, 25, 27, 28, 41; C.I. basic green 1; C.I. vat green 1, etc.

As the pigment, well-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 can be used individually or in combination of 2 or more types.

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. 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 cyan 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 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 yellow colorant may be selected from among the following: C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162 mentioned above ; 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. Reaction Sexual 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; and 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.

The yellow coloring agent is preferably yellow dye and yellow pigment, preferably yellow pigment, more preferably quinophthalone yellow pigment, metal-containing yellow pigment and isoindoline yellow pigment, and C.I. pigment Yellow 129, 138, 139, 150, 185 are especially good.

The orange colorant may be selected from among the following: C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99 mentioned above; C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; C.I. Reactive Orange 16; C.I. Direct Orange 26, 34, 39, 41, 46 , 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107 and other orange dyes; and C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments.

Orange colorant, orange dye and orange pigment are preferred, orange pigment is preferred, C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65 , 71, 73 are better.

The red colorant may be selected from among the following: 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 and other red dyes; and 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.

The red coloring agent is preferably red dyes and red pigments, such as azo dyes, anthraquinone dyes, triphenylmethane dyes, dibenzopyran dyes, perylene dyes, azo pigments, diketopyrrolopyrrole pigments, Anthraquinone pigments, dibenzopyran pigments, and perylene pigments are preferred, and C.I. Acid Red 52, C.I. Pigment Red 144, 177, 179, 242, 254, and 269 are more preferred.

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

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

The coloring composition of the present invention is produced by mixing a compound represented by formula (I), a resin, a solvent (E), a coloring agent (A1) containing liquid containing a coloring agent (A1) and a solvent (E) better. The aforementioned production method is to prepare a colored composition by mixing a compound represented by formula (I), a resin, and a solvent (E) using a bead mill, etc., and mix the obtained colored composition with a colorant (A1) and The method of mixing the coloring agent (A1) containing solution of the solvent (E) is preferable.

The colorant (A1) may also be subjected to rosin treatment, surface treatment using a colorant derivative having an acidic or basic group introduced therein, or grafting treatment on the surface of the colorant (A1) using a polymer compound, etc. , Micronization treatment using sulfuric acid micronization method, etc., cleaning treatment using organic solvents, water, etc. to remove impurities, removal treatment using ion exchange method, etc. for ionic impurities, etc. The particle size of the coloring agent (A1) is preferably roughly uniform. The colorant (A1) can be dispersed by containing a dispersant, and the colorant (A1) is in a state of being uniformly dispersed in the colorant (A1)-containing liquid. The coloring agent (A1) may be dispersed individually, or may be mixed and dispersed in plural.

Examples of the dispersant include surfactants and the like, and may be any of cationic, anionic, nonionic, and amphoteric surfactants. Specifically, surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants are exemplified. These dispersants can be used individually or in combination of 2 or more types. As dispersants, when expressed by trade name, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), SOLSPERSE (registered trademark) (manufactured by ZENECA Co., Ltd.), EFKA (registered trademark) (BASF Co., Ltd.), AJISPER (registered trademark) (Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (BYK-Chemie Co., Ltd.), BYK (registered trademark) ( BYK-Chemie (stock) system), etc.

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

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

In the liquid containing the coloring agent (A1), the content of the coloring agent (A1) is usually 1% by mass to 90% by mass, preferably 1% by mass to 80% by mass, based on the total amount of solid content. Preferably it is 2 mass % or more and 75 mass % or less.

When preparing the coloring agent (A1)-containing liquid containing the coloring agent (A1) and the solvent (E) in advance, and then using the coloring agent (A1)-containing liquid to prepare the coloring composition of the present invention, the coloring agent (A1)-containing liquid may be A part or all of the resin (B) contained in a coloring composition is contained beforehand, Preferably it is a part. By containing the resin (B) in advance, the dispersion stability of the colorant (A1)-containing liquid 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, more preferably 10 to 100 parts by mass relative to 100 parts by mass of the colorant (A1). .

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

The content of the compound (I) in the total amount of the colorant (A) is usually at least 0.001% by mass, preferably at least 0.003% by mass, more preferably at least 0.005% by mass, and the upper limit is 100% by mass or less, preferably 99.999% by mass. It is preferably at most mass %, more preferably at most 99.997 mass %.

When the colorant (A1) is contained, the content of the colorant (A1) is preferably at least 0.1 part by mass, more preferably at least 0.5 part by mass, and more preferably at least 1 part by mass, relative to 100 parts by mass of the compound (I). Better, preferably less than 10,000 parts by mass, more preferably less than 5,000 parts by mass.

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

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized by active radicals and/or acids generated from the polymerization initiator (D), such as a polymerizable compound having an ethylenically unsaturated bond, etc., preferably (meth)acrylate compounds.

Polymerizable compounds having one ethylenically unsaturated bond, for example, nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate , 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc., and the above-mentioned monomer (a), monomer (b) and monomer (c).

Polymerizable compounds having two ethylenically unsaturated bonds, for example, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, base) acrylate, triethylene glycol di(meth)acrylate, bis(acryloxyethyl) ether of bisphenol A and 3-methylpentanediol di(meth)acrylate, etc.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds. Such polymerizable compounds include, for example, trimethylolpropane tri(meth)acrylate, neopentylthritol tri(meth)acrylate, neopentylthritol tetra(meth)acrylate, dipentyl Tetrol Penta(meth)acrylate, Di-Neopentylthritol Hexa(Meth)acrylate, Tri-Neopentylthritol Octa(Meth)acrylate, Tri-Neopentylthritol Hepta(Meth)acrylate, Four Neopentylthritol deca(meth)acrylate, tetraneopentylthritol nona(meth)acrylate, ginseng(2-(meth)acryloxyethyl)isocyanurate, ethylene glycol Modified Neopentylthritol Tetra(Meth)acrylate, Ethylene Glycol Modified Di-Neopentylthritol Hexa(Meth)acrylate, Propylene Glycol Modified Neopentylthritol Tetra(Meth)acrylate, Propylene Glycol Modified Dineopentaerythritol hexa(meth)acrylate, caprolactone-modified neopentylthritol tetra(meth)acrylate and caprolactone-modified dipenteoerythritol hexa(meth)acrylate, etc., compared with Preferable examples include diperythritol penta(meth)acrylate and dipenteoerythritol hexa(meth)acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably not less than 150 and not more than 2,900, more preferably not less than 250 and not more than 1,500.

In the colored curable composition, the content of the polymerizable compound (C) is preferably 1 to 65% by mass, more preferably 3 to 60% by mass, and 5 to 55% by mass relative to the total amount of solid content. % is better.

The curable colored composition of the present invention may also 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 well-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, three

Compounds and acyl phosphine oxide compounds, etc.

Examples of O-acyl oxime compounds include N-benzoyloxy-1-(4-phenylthiophenyl)butan-1-one-2-imine, N-benzoyloxy Base-1-(4-phenylthiophenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentyl Propan-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetyl Oxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2- Methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4- (3,3-Dimethyl-2,4-dioxolylmethoxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyl Oxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine and N-benzyl Acyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine Wait. Moreover, as an O-acyl oxime compound, commercial items, such as IRGACURE OXE01 and OXE02 (above, manufactured by BASF Co., Ltd.), and N-1919 (made by ADEKA Co., Ltd.) can also be used. Among them, the O-acyl oxime compound is selected from N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy 1-(4-phenylthiophenyl)octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentyl Preferably at least one of the group consisting of propan-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2- Imines are preferred.

As the alkylphenone compound, 2-methyl-2-morpholinyl-1-(4-methylthiophenyl)propan-1-one, 2-dimethylamino-1-( 4-morpholinophenyl)-2-benzylbutan-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4- (4-morpholinyl)phenyl]butan-1-one, etc. As the alkylphenone compound, commercial items such as IRGACURE 369, 907, and 379 (the above, manufactured by BASF Corporation) can also be used.

As the alkyl phenone compound, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethyl Oligomers of oxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one , α,α-diethoxyacetophenone and benzyl dimethyl ketal.

Examples of bisimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbisimidazole, 2,2'-bis(2,3 -dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to JP-A-6-75372, JP-A-6-75373, etc.), 2,2' -Bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'- Tetrakis(alkoxyphenyl)bisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)bisimidazole, 2,2 '-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Application Laid-Open No. 62 -174204, etc.) and imidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted by carboalkoxy (for example, refer to JP-A-7-10913, etc.), etc.

化合物者，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]-13,5-三

、2,4-雙(三氯甲基)-6-[2-(4-二乙胺基-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。 as three

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

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

, 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]-13,5-tri

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

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

Wait.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like.

And as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether can be enumerated; Phenyl ketone, methyl o-benzoyl benzoate, 4-phenyl diphenyl ketone, 4-benzoyl-4'-methyl diphenyl sulfide, 3,3',4,4' - Diphenyl ketone compounds such as tetrakis(tert-butylperoxycarbonyl) diphenyl ketone and 2,4,6-trimethyl diphenyl ketone; 9,10-phenanthrenequinone, 2-ethylanthraquinone and Quinone compounds such as camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl phenylglyoxylate and titanocene compounds, etc.

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

化合物、醯基氧化膦化合物、O-醯基肟化合物及雙咪唑化合物所組成群組的至少一種之聚合起始劑，較佳是含有O-醯基肟化合物之聚合起始劑。 The polymerization initiator (D) preferably contains a compound selected from the group consisting of alkyl phenone compounds, three

The polymerization initiator is at least one kind of compound, an acyl phosphine oxide compound, an O-acyl oxime compound, and a bisimidazole compound, preferably a polymerization initiator containing an O-acyl oxime compound.

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

The colored curable composition of the present invention may also contain a polymerization initiation aid (D1).

<Polymerization Initiation Auxiliary (D1)>

The polymerization initiation aid (D1) is a compound or a sensitizer used to accelerate the polymerization of the polymerizable compound whose polymerization is initiated by the polymerization initiator. When a polymerization start aid (D1) is contained, it is usually used in combination with a polymerization start agent (D).

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

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoate Isoamyl aminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4, 4'-bis(dimethylamino)diphenyl ketone (commonly known as Michelle's ketone), 4,4'-bis(diethylamino)diphenyl ketone and 4,4'-bis(ethyl methylamino) diphenyl ketone, etc., preferably 4,4'-bis(diethylamino) diphenyl ketone. Moreover, as an amine compound, a commercial item, such as EAB-F (made by Hodogaya Chemical Industry Co., Ltd.), can also be used.

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

Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, Xanthone and 1-chloro-4-propoxythioxanthone, etc.

Examples of carboxylic acid compounds include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, and Glycolic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine And naphthyloxyacetic acid, etc.

When these polymerization initiation aids (D1) are used, the content of the polymerization initiation aid (D1) in the total amount of solids in the colored curable composition is preferably 0.001 to 30% by mass, more preferably 0.01 to 20% by mass.

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

<Leveling agent (F)>

The leveling agent (F) includes silicone-based surfactants, fluorine-based surfactants, silicone-based surfactants having fluorine atoms, and the like. These may have a polymeric group in a side chain.

Examples of the silicone-based surfactant include those 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 (manufactured by TORAY DOW CORNING Co., Ltd.), KP321 , KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan contract company), etc.

Examples of the fluorine-based surfactant include those having a fluorocarbon chain in the molecule, and the like. 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 Co., Ltd.), EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352 (manufactured by Mitsubishi Material Electron Chemicals Co., Ltd.), SURFLON (registered trademark) S381, SURFLON S382, SURFLON SC101, SURFLON SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by DAIKIN FINECHEMICAL Research Institute Co., Ltd.), etc.

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, MEGAFAC F443 (manufactured by DIC Co., Ltd.) etc. are mentioned.

When the leveling agent (F) is contained, its content is usually 0.0005% by mass to 1% by mass, preferably 0.001% by mass to 0.5% by mass, more preferably 0.001% by mass, based on the total amount of the coloring composition. It is more than mass % and 0.2 mass %, More preferably, it is 0.002 mass % or more and 0.1 mass % or less, Most preferably, it is 0.005 mass % or more and 0.1 mass % or less. When the content rate of a leveling agent (F) exists in the said range, the flatness of a color filter can be made favorable.

<Antioxidant>

From the viewpoint of improving the heat resistance and light resistance of the colorant, it is preferable to use the antioxidant alone or in combination of two or more. The antioxidant is not particularly limited as long as it is an antioxidant commonly used industrially, and phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, and the like can be used.

-2,4,6(1H,3H,5H)-三酮、BASF(股)製)、IRGANOX3790(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)、IRGANOX1035(Irganox 1035：硫二伸乙基雙[3-(3,5-二-第三丁基-4-羥苯基)丙酸酯]、BASF(股)製)、IRGANOX1135(Irganox 1135：苯丙酸、3,5-雙(1,1-二甲基乙基)-4-羥基、C7-C9側鏈烷酯、BASF(股)製)、IRGANOX1520L(Irganox 1520L：4,6-雙(辛硫基甲基)-鄰甲酚、BASF(股)製)、IRGANOX3125(Irganox 3125、BASF(股)製)、IRGANOX565(Irganox 565：2,4-雙(正辛硫基)-6-(4-羥 基3’、5’-二-第三丁基苯胺基)-1,3,5-三

、BASF(股)製)、Adekastab AO-80(Adekastab 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(股)製)、Sumilizer BHT(Sumilizer BHT、住友化學(股)製)、Sumilizer GA-80(Sumilizer GA-80、住友化學(股)製)、Sumilizer GS(Sumilizer GS、住友化學(股)製)、Cyanox1790(Cyanox 1790、CYTEC(股)製)及VITAMIN E(EISAI(股)製)等。 Examples of the aforementioned phenolic antioxidants include IRGANOX 1010 (Irganox 1010: Neopentylthritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], BASF ( Co., Ltd.), IRGANOX1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, BASF Co., Ltd.), IRGANOX1330 (Irganox 1330: 3,3',3",5,5',5"-hexa-tert-butyl-a,a',a"-(mesitylene-2,4,6-triyl)tri-p-cresol , BASF Co., Ltd.), IRGANOX3114 (Irganox 3114: 1,3,5-ginseng (3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-tri

-2,4,6(1H,3H,5H)-trione, manufactured by BASF Co., Ltd.), IRGANOX3790 (Irganox 3790: 1,3,5-ginseng ((4-tert-butyl-3-hydroxy-2 ,6-xylyl)methyl)-1,3,5-tri

-2,4,6(1H,3H,5H)-trione, manufactured by BASF Co., Ltd.), IRGANOX1035 (Irganox 1035: thiobisethylenebis[3-(3,5-di-tert-butyl- 4-Hydroxyphenyl)propionate], manufactured by BASF Co., Ltd.), IRGANOX 1135 (Irganox 1135: phenylpropionic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxyl, C7- C9 side chain alkyl ester, manufactured by BASF Co., Ltd.), IRGANOX1520L (Irganox 1520L: 4,6-bis(octylthiomethyl)-o-cresol, manufactured by BASF Co., Ltd.), IRGANOX3125 (Irganox 3125, BASF Co., Ltd. )), IRGANOX565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxyl 3', 5'-di-tert-butylanilino)-1,3,5-tri

, BASF Co., Ltd.), Adekastab AO-80 (Adekastab AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyl Oxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro(5,5)undecane, manufactured by ADEKA Co., Ltd.), Sumilizer BHT (Sumilizer BHT, Sumitomo Chemical Co., Ltd.), Sumilizer GA-80 (Sumilizer GA-80, Sumitomo Chemical Co., Ltd.), Sumilizer GS (Sumilizer GS, Sumitomo Chemical Co., Ltd.), Cyanox1790 (Cyanox 1790, CYTEC Co., Ltd.) And VITAMIN E (EISAI (stock) system), etc.

Examples of the phosphorus-based antioxidant include IRGAFOS 168 (Irgafos 168: ginseng (2,4-di-tert-butylphenyl) phosphite, manufactured by BASF Co., Ltd.), IRGAFOS 12 (Irgafos 12: Reference [2-[[2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphin-6-yl]oxy]ethyl] Amine, manufactured by BASF Co., Ltd.), IRGAFOS 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl) ethyl phosphorous acid, BASF Co., Ltd. )), Adekastab 329K (manufactured by ADEKA), Adekastab PEP36 (manufactured by ADEKA), Adekastab PEP-8 (manufactured by ADEKA), Sandstab P-EPQ (manufactured by CLARIANT), Weston 618 (manufactured by Weston 618, produced by GE), Weston 619G (Weston 619G, produced by GE), Ultranox 626 (Ultranox 626, produced by GE) and Sumilizer GP (Sumilizer GP: 6-[3-(3-tertiary butyl-4- Hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenzo[d,f][1.3.2]dioxaphosphopane) (Sumitomo Chemical Co., Ltd.), etc.

Examples of the aforementioned sulfur-based antioxidants include dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl, and distearyl ester, and tetrakis[methylene(3- β-alkylmercaptopropionate compounds of polyalcohols such as dodecylthio)propionate]methane, and the like.

<other ingredients>

The coloring composition of the present invention may optionally contain fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents, and other well-known additives in this technical field.

Examples of adhesion promoters include vinyltrimethoxysilane, vinyltriethoxysilane, vinylginseng (2-methoxyethoxy)silane, 3-glycidoxypropyl Trimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclo Hexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercapto Propyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethylsilane Oxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-amine Propyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane, etc.

<Color filter>

A color filter can be formed from the colored composition or colored curable composition of the present invention. The method for forming a colored pattern includes lithography, inkjet method, printing method, etc., preferably lithography. Lithography is a method in which the aforementioned colored curable composition is coated on a substrate and dried to form a colored curable composition layer, and the colored curable composition layer is exposed and developed through a photomask . In the lithography method, the colored curable composition preferably contains a polymerization initiator (D). In the lithography method, a colored coating film of a cured product of the above-mentioned colored curable composition layer can be formed by not using a photomask and/or without developing during exposure. The colored pattern and colored coating film formed in this way can be used as the color filter of this invention.

The film thickness of the manufactured color filter is not particularly limited, and can be appropriately adjusted according to the purpose, application, etc., 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, silicon, or a substrate on which a thin film of aluminum, silver, or silver/copper/palladium alloy is formed can be used. On these substrates, additional color filter layers, resin layers, transistors, circuits, etc. can also be formed.

The formation of pixels of various colors by lithography can be carried out under well-known or conventional devices and conditions. For example, it can manufacture as follows.

First, the colored curable composition is coated on the substrate, and the volatile components such as solvents are removed and dried by heat drying (pre-baking) and/or reduced pressure drying to obtain a smooth colored curable composition Floor.

Examples of the coating method include a spin coat method, a slit coat method, a slit and spin coat method, and the like.

Next, the colored curable composition layer is exposed through a photomask for forming the desired colored pattern. A mask aligner and a stepper are used to uniformly irradiate the entire exposure surface with parallel light and to align the mask and the substrate on which the colored curable composition layer is formed. It is better to wait for the exposure device.

A colored pattern can be formed on a substrate by contacting the exposed colored curable composition layer with a developer and developing it. By development, the unexposed portion of the colored curable composition layer can be dissolved in a developing solution and removed.

As the developer, for example, an aqueous solution of a basic compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is preferable.

The image development method may be any one of a dipping method, a dipping method, a spraying method, and the like. In addition, the substrate can be tilted at any angle during development.

The developed substrate is preferably washed with water.

Furthermore, it is preferable to post-bak the obtained colored pattern.

The aforementioned color filter is useful as a color filter used in display devices (such as liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging elements, and is especially useful as a color filter used in liquid crystal display devices. color filter.

[Example]

Hereinafter, examples are given to illustrate the present invention more specifically, but the present invention is of course not limited by the following examples, and it goes without saying that it can be implemented with appropriate changes within the range that can be adapted to the purpose described above/later. Any of these are included in the technical scope of the present invention.

"%" and "parts" in the examples mean % by mass and parts by mass unless otherwise specified.

In the following synthesis examples, the structures of the compounds were confirmed by NMR (JMM-ECA-500; manufactured by JEOL Ltd.) or mass analysis (LC; Model 1200 manufactured by Agilent, MASS; Model LC/MSD6130 manufactured by Agilent)

The measurement of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the polystyrene conversion of resin was performed on the following conditions using the GPC method.

Device: HLC-8120GPC (manufactured by TOSOH Co., Ltd.)

Column: TSK-GELG2000HXL

Column temperature: 40°C

Solvent: THF

Flow rate: 1.0mL/min

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

Injection volume: 50μL

Detector: RI

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

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

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 triflate. 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 (I-2).

<Identification of Compound Represented by Formula (I-2)>

(mass analysis) ionization mode = ESI+: m/z = 365 [M-CF ₃ SO ₃ ] ⁺

Exact Mass: 514

5.00 parts of the compound represented by formula (I-2) and 1500 parts of methanol were mixed. A mixture of 10.4 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Japan Co., Ltd.) and 104 parts of methanol was added to this mixture. This mixture was filtered, and the obtained residue was wash|cleaned using 500 parts of methanol. The residue was dried under reduced pressure at 60° C. to obtain 12.4 parts of the compound represented by the formula (I-14).

<Identification of Compound Represented by Formula (I-14)>

(mass analysis) ionization mode = ESI+: m/z = 365 [(M-PW ₁₂ O ₄₀ )/3] ⁺

Exact Mass: 3974

[Heat resistance evaluation]

The differential scanning calorimetry of the compound obtained in Example 1 was performed using a differential thermogravimetric simultaneous measurement device (TG/DTA6200 manufactured by SII Nano Technology). The sample amount used for one measurement was 5 mg. The measurement temperature starts from 45°C, increases the temperature at a rate of 5°C per minute, and measures to 550°C. The temperature T ₅ (under nitrogen) at which the weight loss rate becomes 5% was determined in a nitrogen atmosphere. The results are shown in Table 11.

From the results in Table 11, it can be seen that the compound system of the present invention has high heat resistance.

Synthesis Example 1

In a flask equipped with a reflux cooler, a dropping funnel, and a stirrer, an appropriate amount of nitrogen gas was flowed to replace the nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was added, and it was heated to 80° C. while stirring. Secondly, 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 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 obtained by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was dropped over 6 hours. After completion|finish of dripping, after maintaining at the same temperature for 4 hours, it cooled to room temperature and obtained the copolymer (resin B1) solution of 35.0% of solid content. The weight average molecular weight (Mw) of the obtained resin B1 was 8800, the degree of dispersion was 2.1, and the acid value of the solution was 28 mg-KOH/g.

Synthesis example 2

In a flask equipped with a reflux cooler, a dropping funnel, and a stirrer, an appropriate amount of nitrogen gas was flowed to replace the atmosphere with nitrogen gas, 257 parts of ethyl lactate was added, and the mixture was heated to 75° C. while stirring. Secondly, 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 ,6} ] A mixed solution of 369 parts of a mixture of decane-9-yl ester and 25 parts of ethyl lactate was dropped over 5 hours. On the other hand, a mixed solution obtained by dissolving 11 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 162 parts of ethyl lactate was dropped over 5 hours. After completion|finish of dripping, after maintaining at the same temperature for 5 hours, 95 parts of ethyl lactates were added, and it cooled to room temperature, and obtained the copolymer (resin B2) solution of 47.7% of solid content. The weight average molecular weight (Mw) of the obtained resin B2 was 8100, the degree of dispersion was 1.9, and the acid value of the solution was 53 mg-KOH/g.

Synthesis example 3

In a flask equipped with a reflux cooler, a dropping funnel, and a stirrer, an appropriate amount of nitrogen gas was flowed to replace the nitrogen atmosphere, and 371 parts of propylene glycol monomethyl ether acetate was added, and heated to 85° C. while stirring. Secondly, 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 A mixed solution of 225 parts of a mixture of ]decane-9-yl ester, 81 parts of vinyl toluene (isomer mixture), and 80 parts of propylene glycol monomethyl ether acetate was dropped over 4 hours. On the other hand, a solution obtained by dissolving 30 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) in 160 parts of propylene glycol monomethyl ether acetate was dropped over 5 hours. . After completion|finish of dripping of an initiator solution, after maintaining at the same temperature for 4 hours, it cooled to room temperature and obtained the copolymer (resin B3) solution of 37.5% of solid content. The weight average molecular weight (Mw) of the obtained resin B3 was 10600, the degree of dispersion was 2.01, and the acid value of the solution was 43 mg-KOH/g.

Synthesis Example 4

In a flask equipped with a reflux cooler, a dropping funnel, and a stirrer, flow an appropriate amount of nitrogen gas and replace it with a nitrogen atmosphere, add 54 parts of ethyl lactate and 141 parts of propylene glycol monomethyl ether acetate, and heat to 85°C while stirring until. Secondly, 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 ] The mixed solution of 23 parts of the mixture of decane-9-yl ester, 161 parts of cyclohexylmaleimide, 12 parts of 2-hydroxyethyl methacrylate, and 493 parts of propylene glycol monomethyl ether acetate costs 5 Hours drip. On the other hand, a solution obtained by dissolving 3 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 78 parts of propylene glycol monomethyl ether acetate was dropped over 6 hours. After completion|finish of dripping, after maintaining at the same temperature for 4 hours, it cooled to room temperature and obtained the copolymer (resin B4) solution of 24.4% of solid content. The weight average molecular weight (Mw) of the obtained resin B4 was 8400, 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 using DEKTAK3 (manufactured by Nippon Vacuum Technology Co., Ltd.).

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

Resin: methacrylic acid/benzyl methacrylate (molar ratio: 30/70) copolymer (manufactured by Tagoka Chemical Industry Co., Ltd., weight average molecular weight

(Mw) 10700, acid value 70-mgKOH/g) 40 parts of 33.8% propylene glycol monomethyl ether acetate solution; stock)) 5.8 parts; polymerization initiator: N-benzoyloxy-1-(4-phenylthiophenyl) octane-1-one-2-imine (IRGACURE (registered trademark) OXE01; BASF Japan company) 0.58 parts; leveling agent: polyether modified silicone oil (Toray Silicone SH8400; TORAY.DOW CORNING (stock)) 0.010 parts; solvent: propylene glycol monomethyl ether 47 parts; solvent: propylene glycol monomethyl 6.8 parts of ether acetates were mixed to obtain a resin composition (SJS) for a sublimation test.

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

The above-obtained resin composition for sublimation test (SJS) was coated on a 2-inch square glass substrate (EAGLE XG; manufactured by Corning Co., Ltd.) by a spin coating method, and allowed to dry at 100° C. for 3 minutes. Volatile components evaporate. After cooling, using an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.), light was irradiated with an exposure amount of 150 mJ/cm ² (365 nm reference) in an air environment. It heated at 220 degreeC in oven for 2 hours, and formed the resin coating film (SJSM) (film thickness 2.2 micrometers) for sublimation test.

Example 2

Colorant (A): 14 parts of compounds represented by formula (I-2); Resin (B): 480 parts of resin B1 solution; Solvent (E): 6.2 parts of propylene glycol monomethyl ether acetate; Solvent (E): Coloring composition 1 was obtained by mixing 500 parts of N-methyl-2-pyrrolidone and 0.063 parts of surfactant: polyether-modified silicone oil (Toray Silicone SH8400; manufactured by TORAY.DOW CORNING Co., Ltd.).

Example 3

Colorant (A): 36 parts of compounds represented by formula (I-14); Resin (B): 410 parts of resin B1 solution; Solvent (E): 6.2 parts of propylene glycol monomethyl ether acetate; Solvent (E): Coloring composition 2 was obtained by mixing 540 parts of N-methyl-2-pyrrolidone and 0.063 parts of surfactant: polyether-modified silicone oil (Toray Silicone SH8400; manufactured by TORAY.DOW CORNING Co., Ltd.).

Example 4

Coloring agent (A): 10 parts of compounds represented by formula (I-14); 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 silicone oil (Toray Silicone SH8400 ; TORAY-DOW CORNING Co., Ltd.) 0.020 parts were mixed to obtain coloring composition 3.

Example 5

Colorant (A): 10 parts of compound represented by formula (I-14), 10 parts of dispersant (BYK-LPN21324; manufactured by BYK-Chemie.Japan Co., Ltd.), resin (B): 11 parts of resin B1 solution , and solvent (E): 100 parts of the coloring composition obtained by mixing 160 parts of propylene glycol monomethyl ether acetate and dispersing the compound represented by formula (I-14) using a bead mill; resin (B): resin 55 parts of B1 solution; solvent (E): 3.6 parts of propylene glycol monomethyl ether acetate; and surfactant: polyether modified silicone oil (Toray Silicone SH8400; TORAY.DOW CORNING (stock)) 0.010 parts mixed and Coloring composition 4 was obtained.

Comparative example 1

Colorant (A): 611 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-dimethyl Coloring composition 5 was obtained by mixing 630 parts of methamide; and 0.063 parts of surfactant: polyether-modified silicone oil (Toray Silicone SH8400; manufactured by TORAY-DOW CORNING Co., Ltd.).

[Sublimation Evaluation] Example 6

Coloring composition 1 was coated on a 2-inch square glass substrate (EAGLE XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a coloring composition layer. 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 made to face each other with the space|interval of 70 micrometers open, and they post-baked at 220 degreeC for 40 minutes. The color difference (ΔEab*) before and after heating of the resin coating film (SJSM) for a sublimation test was measured using the colorimeter (OSP-SP-200; OLYMPUS company make). When the color difference (ΔEab*) is 5.0 or more, it means that the colorant has sublimation properties. The results are shown in Table 12. In Table 12, ◯ indicates that the colorant does not have sublimation property, and the × system indicates that the colorant has sublimation property.

Example 7

Except having changed the coloring composition 1 into the coloring composition 2, it carried out similarly to Example 6, and performed sublimation evaluation. The results are shown in Table 12.

Example 8

Except having changed the coloring composition 1 into the coloring composition 3, it carried out similarly to Example 6, and performed sublimation evaluation. The results are shown in Table 12.

Example 9

Except having changed the coloring composition 1 into the coloring composition 4, it carried out similarly to Example 6, and performed sublimation evaluation. The results are shown in Table 12.

Comparative example 2

Except having changed the coloring composition 1 into the coloring composition 5, it carried out similarly to Example 6, and performed sublimation evaluation. The results are shown in Table 12.

From the above results, it is known that the coloring composition containing the compound of the present invention can reduce the sublimation of the coloring agent.

Example 10

Colorant (A): 100 parts of compound represented by formula (I-14), 130 parts of dispersant (BYK-LPN21324; manufactured by BYK-Chemie. Japan Co., Ltd.), resin (B): 170 parts of resin B4 solution , and solvent (E): 380 parts of the coloring composition obtained by mixing 610 parts of propylene glycol monomethyl ether acetate and dispersing the compound represented by formula (I-14) using a bead mill; : 18 parts of CI Pigment Yellow 138 (pigment), 7.6 parts of dispersant, 7.6 parts of resin, and solvent (E): 120 parts of propylene glycol monomethyl ether acetate mixed and dispersed with a bead mill to disperse the pigment. Coloring agent (A): 4.2 parts of a compound represented by the following formula (manufactured using the method described in Japanese Patent Laid-Open No. 2013-235257);

Resin (B): 21 parts of resin B3 solution; polymerizable compound (C): 25 parts of polymerizable compound (A9550; manufactured by Shin-Nakamura Chemical Co., Ltd.); polymerization initiator (D): compound represented by the following formula (manufactured 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 silicone oil (Toray Colored curable composition 1 was obtained by mixing 0.075 parts of Silicone SH8400; manufactured by TORAY-DOW CORNING Co., Ltd.

[Manufacture of coloring pattern]

The colored curable composition 1 was coated on a 2-inch square glass substrate (EAGLE XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a colored curable composition layer. After cooling, set the distance between the substrate with the colored curable composition layer and the quartz glass photomask at 200 μm, and use an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.) at 80 mJ/cm Exposure was performed at an exposure amount (365nm reference) of ² . In addition, as a photomask, the thing in which the line-and-space pattern of 100 micrometers was formed was used. The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25°C for 70 seconds to develop, and washed with water. A colored pattern was obtained by post-baking the colored coating film at 230° C. for 30 minutes.

[Sublimation Evaluation]

The colored curable composition 1 was coated on a 2-inch square glass substrate (EAGLE XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed was exposed using an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.) at an exposure dose of 80 mJ/cm ² (based on 365 nm) in an air environment. The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25°C for 70 seconds to develop, and washed 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 sublimation test obtained above were made to face each other with the space|interval of 70 micrometers open, and they post-baked at 220 degreeC for 40 minutes.

The color difference (ΔEab*) before and after heating of the resin coating film (SJSM) for a sublimation test was measured using the colorimeter (OSP-SP-200; OLYMPUS company make). When the color difference (ΔEab*) is 5.0 or more, it means that the colorant has sublimation properties. The results are shown in Table 13. In Table 13, ◯ means that the colorant does not have sublimation property, and × means that the colorant has sublimation property.

Example 11

Colorant (A): 100 parts of compound represented by formula (I-14), 130 parts of dispersant (BYK-LPN21324; manufactured by BYK-Chemie. Japan Co., Ltd.), resin (B): 170 parts of resin B4 solution , and solvent (E): 340 parts of the coloring composition obtained by mixing 610 parts of propylene glycol monomethyl ether acetate and dispersing the compound represented by formula (I-14) using a bead mill; : 18 parts of CI Pigment Yellow 138 (pigment), 7.6 parts of dispersant, 7.6 parts of resin, and solvent (E): 120 parts of propylene glycol monomethyl ether acetate mixed and dispersed with a bead mill to disperse the pigment. Colorant (A): 7.8 parts of the compound represented by the following formula (made by the method described in Japanese Patent Laid-Open No. 2013-235257);

Resin (B): 27 parts of resin B3 solution; polymerizable compound (C): 26 parts of polymerizable compound (A9550; manufactured by Shin-Nakamura Chemical Co., Ltd.); polymerization initiator (D): compound represented by the following formula (manufactured 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 silicone oil (Toray Silicone SH8400; manufactured by TORAY-DOW CORNING Co., Ltd.) was mixed in 0.075 parts to obtain Colored Curable Composition 2.

Except having changed the colored curable composition 1 into the colored curable composition 2, it carried out similarly to Example 10, and performed manufacture of the colored pattern and sublimation property evaluation. Table 13 shows the sublimation evaluation results.

Example 12

Colorant (A): 100 parts of compound represented by formula (I-14), 130 parts of dispersant (BYK-LPN21324; manufactured by BYK-Chemie. Japan Co., Ltd.), resin (B): 170 parts of resin B4 solution , and solvent (E): 290 parts of the coloring composition obtained by mixing 610 parts of propylene glycol monomethyl ether acetate and dispersing the compound represented by formula (I-14) using a bead mill; : 23 parts of CI Pigment Yellow 138 (pigment), 9.6 parts of dispersant, 9.6 parts of resin, and solvent (E): 150 parts of propylene glycol monomethyl ether acetate mixed and dispersed with a bead mill to disperse the pigment. Coloring agent (A): 5.1 parts of the compound represented by the following formula (made by the method described in Japanese Patent Laid-Open No. 2013-235257);

Resin (B): 31 parts of resin B3 solution; polymerizable compound (C): 27 parts of polymerizable compound (A9550; manufactured by Shin-Nakamura Chemical Co., Ltd.); polymerization initiator (D): compound represented by the following formula (manufactured 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 silicone oil (Toray Silicone SH8400; manufactured by TORAY-DOW CORNING Co., Ltd.) was mixed in 0.075 parts to obtain colored curable composition 3.

Except having changed the colored curable composition 1 into the colored curable composition 3, it carried out similarly to Example 10, and performed manufacture of the colored pattern and sublimation property evaluation. Table 13 shows the sublimation evaluation results.

Example 13

Colorant (A): 100 parts of compound represented by formula (I-14), 130 parts of dispersant (BYK-LPN21324; manufactured by BYK-Chemie. Japan Co., Ltd.), resin (B): 170 parts of resin B4 solution , and solvent (E): 270 parts of the coloring composition obtained by mixing 610 parts of propylene glycol monomethyl ether acetate and dispersing the compound represented by formula (I-14) using a bead mill; : 23 parts of CI Pigment Yellow 138 (pigment), 9.6 parts of dispersant, 9.6 parts of resin, and solvent (E): 150 parts of propylene glycol monomethyl ether acetate mixed and dispersed with a bead mill to disperse the pigment. Colorant (A): 7.4 parts of the compound represented by the following formula (made using the method described in Japanese Patent Laid-Open No. 2013-235257);

Resin (B): 35 parts of resin B3 solution; polymerizable compound (C): 27 parts of polymerizable compound (A9550; manufactured by Shin-Nakamura Chemical Co., Ltd.); 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 silicone oil (Toray Silicone SH8400; manufactured by TORAY-DOW CORNING Co., Ltd.) was mixed in 0.075 parts to obtain Colored Curable Composition 4.

Except changing the coloring curable composition 1 into the coloring curable composition 4, it carried out similarly to Example 10, and performed manufacture of the coloring pattern and sublimation property evaluation. Table 13 shows the sublimation evaluation results.

Example 14

Except changing the compound represented by the formula (I-14) to the compound represented by the formula (I-2), it was carried out in the same manner as in Example 10 to obtain a colored curable composition 5, and to produce a colored pattern and evaluate its sublimation property. . Table 13 shows the sublimation evaluation results.

Example 15

Except changing the compound represented by the formula (I-14) to the compound represented by the formula (I-2), it was carried out in the same manner as in Example 13 to obtain a colored curable composition 6, and to produce a colored pattern and evaluate its sublimation property. . Table 13 shows the sublimation evaluation results.

Comparative example 3

Except having changed the compound represented by formula (I-14) into coumarin 6, it carried out similarly to Example 10, and obtained the coloring curable composition 7, and performed manufacture of the coloring pattern, and sublimation property evaluation. Table 13 shows the sublimation evaluation results.

Comparative example 4

Except changing the compound represented by formula (I-14) into coumarin 6, it carried out similarly to Example 13, and obtained the coloring curable composition 8, and performed manufacture of the coloring pattern, and sublimation evaluation. Table 13 shows the sublimation evaluation results.

From the above results, it was found that the colored curable composition containing the compound of the present invention reduces the sublimation of the colorant.

[Possibility of industrial use]

The coloring composition and coloring curable composition of the present invention can reduce the sublimation property of the colorant, and are suitable for use in display devices such as color filters and liquid crystal display devices.

Claims (10)

A coloring composition containing a compound represented by formula (I) and a resin,

In the formula (I), R ^N1 and R ^N2 independently represent an aliphatic hydrocarbon group with 1 to 40 carbon atoms that may have a substituent, and R ^N3 represents a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent or may have In the heterocyclic group of the substituent, R ¹ to R ³ , R ⁵ to R ⁸ 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 , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, optionally substituted hydrocarbon group having 1 to 40 carbon atoms or optionally substituted The heterocyclic group of the group, R ⁴ 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. A halogen atom, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent, or a heterocyclic group that may have a substituent, and R ¹⁰¹ represents a carbon that may have a substituent A hydrocarbon group with a number of 1 to 40 or a heterocyclic group that may have a substituent, ^R102 represents a hydrogen atom, a hydrocarbon group with a carbon number of 1 to 40 that may have a substituent, or a heterocyclic group that may have a substituent, and M represents a hydrogen atom Or an alkali metal atom. When R ¹⁰¹ , R ¹⁰² and M exist in plural, they may be the same or different. A ^g- represents the anion of a heteropolymeric or homotropic polymeric acid containing tungsten as an essential element, g represents an integer of 1-14. The coloring composition as described in claim 1 of the patent application, wherein R ^N1 and R ^N2 are independently an alkyl group having 1 to 10 carbon atoms which may have substituents. The coloring composition as described in item 1 or 2 of the scope of application further contains a solvent. The coloring composition as described in claim 1 or 2 of the patent application further contains a yellow coloring agent, an orange coloring agent or a red coloring agent. A colored curable composition, which contains the colored composition described in any one of items 1 to 4 of the scope of application, and a polymerizable compound. The colored curable composition described in claim 5 of the patent application further contains a polymerization initiator. A color filter formed of the colored composition described in any one of claims 1 to 4 or the colored curable composition described in claims 5 or 6. A liquid crystal display device comprising the color filter described in item 7 of the patent application. A compound represented by formula (IB),

In the formula (IB), R ^N1 and R ^N2 independently represent an aliphatic hydrocarbon group with a carbon number of 1 to 40 that may have a substituent, and R ^N3 represents a hydrocarbon group with a carbon number of 1 to 40 that may have a substituent or may have In the heterocyclic group of the substituent, R ¹ to R ³ , R ⁵ to R ⁸ 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 , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, optionally substituted hydrocarbon group having 1 to 40 carbon atoms or optionally substituted The heterocyclic group of the group, R ⁴ 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. A halogen atom, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent, or a heterocyclic group that may have a substituent, and R ¹⁰¹ represents a carbon that may have a substituent A hydrocarbon group with a number of 1 to 40 or a heterocyclic group that may have a substituent, ^R102 represents a hydrogen atom, a hydrocarbon group with a carbon number of 1 to 40 that may have a substituent, or a heterocyclic group that may have a substituent, and M represents a hydrogen atom Or an alkali metal atom. When R ¹⁰¹ , R ¹⁰² and M exist in plural, they may be the same or different. B ^h- represents the anion of a heteropolymeric or homotropic polymeric acid containing tungsten as an essential element, h represents an integer of 1 to 14. The compound described in claim 9 of the patent application, wherein R ^N1 and R ^N2 are independently an alkyl group having 1 to 10 carbon atoms which may have substituents.