WO2018198920A1 - Compound and ink using same - Google Patents

Abstract

Provided is a novel compound which has excellent lightfastness, good dissolution stability and solubility in organic solvents and resins, and is suitable for use in yellow dyes, inks and the like. The compound is represented by general formula (1). (In general formula (1), A⁺ represents a structure such as that shown in general formula (2), X is an alkyl group in which at least some of the hydrogen atoms may be substituted with fluorine atoms, Y is a divalent hydrocarbon group, and Z is a photoreactive group.) (In general formula (2), R₁ to R₁₁ each independently represent a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a nitro group, a dialkyl amino group, an alkoxy alkyl group, or a substituted or unsubstituted aryl group.)

Description

Compound and ink using the same

The present invention relates to a novel compound, and in particular, a novel compound having a clear yellow hue, excellent light resistance, good solubility in organic solvents and resins, and dissolution stability, and a dye containing the same , Ink and coloring composition.

An ionic compound called a cationic dye or the like is composed of an organic cation having a positive charge delocalized over a conjugated bond, and usually an inorganic anion, and various paints, water-based inks, oil-based inks, inkjet inks, Used in a wide range of applications such as color filters.
For example, Patent Document 1 discloses that an ionic styrylquinoline-based compound having a hexafluoroantimonate anion is used as a sensitizing dye in an image production method such as a photoresist.
Patent Document 2 discloses a wide range of dyes including styrylquinoline compounds having an anion selected from the group of cyanoboric acid, fluoroalkylphosphoric acid, fluoroalkylboric acid or imidized compounds.

However, these styrylquinoline compounds have insufficient solubility and stability in solvents for use as dyes and inks.
Patent Document 3 discloses a diketopyridine compound which is a leuco dye used for pressure-sensitive and heat-sensitive recording materials. These compounds give a yellow color when contacted with silica gel or a phenol compound, but are not a colored substance used alone as a pigment like the compounds of the present application. These diketopyridine compounds have low solubility in organic solvents and resins.
Patent Document 4 discloses that a sulfonylimide-type counter anion having a photoreactive group is applied to a triarylmethane compound. The purpose is to improve the durability by introducing a polymerizable group, but the solubility in organic solvents and resins is insufficient, and the durability is not sufficiently improved.

Japanese National Patent Publication No. 9-512351 Special table 2007-503477 JP 58-83673 A JP 2012-72205 A

An object of the present invention is to provide a novel compound that exhibits a clear yellowish hue, is excellent in light resistance, and has good solubility in organic solvents and resins.

（一般式（１）中、Ａ^＋は下記一般式（２）、または一般式（３）を表し、Ｘは水素原子の少なくとも一部がフッ素原子に置換されていてもよいアルキル基を表し、Ｙは二価の炭化水素基を表し、Ｚは光反応性基である。）

(一般式（２）中、Ｒ_１～Ｒ_１１は各々独立に、水素原子、ハロゲン原子、アルキル基、水酸基、アルコキシ基、ニトロ基、ジアルキルアミノ基、アルコキシアルキル基、または置換もしくは未置換のアリール基を表す。)

(一般式（３）中、Ｒ_１２～Ｒ_２４は各々独立に、水素原子、ハロゲン原子、アルキル基、水酸基、アルコキシ基、ニトロ基、ジアルキルアミノ基、アルコキシアルキル基、または置換もしくは未置換のアリール基を表す。）)
（ii）一般式(１)におけるＹがアリーレン基であり、Ｚがビニル基、アリル基、(メタ)アクリル基、及び(メタ)アクリロイル基から選ばれる基であり、Ｘがパーフルオロアルキル基である(ｉ)に記載の化合物、
（iii）（ｉ）または（ii）に記載の化合物を含有する染料、
（iv）（ｉ）～（iii）いずれかに記載の化合物を含有するインキ、
（ｖ）（ｉ)～(iv)いずれかに記載の系化合物と樹脂を含有する着色組成物
である。 As a result of intensive studies, the present inventors have found that a compound having a specific structure has very high light resistance and solubility in an organic solvent or a resin, and completed the present invention.
That is, the present invention
(I) a compound represented by the following general formula (1),

(In General Formula (1), A ⁺ represents the following General Formula (2) or General Formula (3), X represents an alkyl group in which at least a part of hydrogen atoms may be substituted with fluorine atoms, Y represents a divalent hydrocarbon group, and Z is a photoreactive group.)

(In the general formula (2), R ₁ to R ₁₁ are each independently a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a nitro group, a dialkylamino group, an alkoxyalkyl group, or a substituted or unsubstituted aryl group. Represents a group.)

(In the general formula (3), R ₁₂ to R ₂₄ are each independently a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a nitro group, a dialkylamino group, an alkoxyalkyl group, or a substituted or unsubstituted aryl group. Represents a group.))
(Ii) Y in the general formula (1) is an arylene group, Z is a group selected from a vinyl group, an allyl group, a (meth) acryl group, and a (meth) acryloyl group, and X is a perfluoroalkyl group. A compound according to (i),
(Iii) a dye containing the compound according to (i) or (ii),
(Iv) an ink containing the compound according to any one of (i) to (iii),
(V) A colored composition comprising the system compound according to any one of (i) to (iv) and a resin.

According to the present invention, it is possible to provide a compound that is excellent in durability, has good solubility in organic solvents and resins, and is suitable for dyes and inks.

FIG. 4 is an absorption spectrum diagram of the compound produced in Example 4 in methanol. FIG. 6 is an absorption spectrum diagram of the compound produced in Example 5 in methanol. FIG. 6 is an absorption spectrum diagram of the compound produced in Example 6 in methanol. FIG. 6 is an absorption spectrum diagram of the compound produced in Example 7 in methanol. FIG. 6 is an absorption spectrum diagram of the compound produced in Example 8 in methanol. FIG. 6 is an absorption spectrum diagram of the compound produced in Example 9 in methanol. FIG. 6 is an absorption spectrum diagram of the compound produced in Example 10 in methanol. 2 is an absorption spectrum diagram of the compound produced in Example 11 in methanol. FIG. FIG. 6 is an absorption spectrum diagram of the compound produced in Example 15 in methanol. FIG. 4 is an absorption spectrum diagram of the compound produced in Example 16 in methanol. 2 is an absorption spectrum diagram of the compound produced in Comparative Example 1 in methanol. FIG. 4 is an absorption spectrum diagram of the compound produced in Comparative Example 2 in methanol. FIG.

（一般式（１）中、Ａ^＋は下記一般式（２）、または一般式（３）を表し、Ｘは水素原子の少なくとも一部がフッ素原子に置換されていてもよいアルキル基を表し、Ｙは二価の炭化水素基を表し、Ｚは光反応性基である。） Hereinafter, the present invention will be described in detail.
[Compound of the present invention]
The compound of the present invention is represented by the following general formula (1).

(In General Formula (1), A ⁺ represents the following General Formula (2) or General Formula (3), X represents an alkyl group in which at least a part of hydrogen atoms may be substituted with fluorine atoms, Y represents a divalent hydrocarbon group, and Z is a photoreactive group.)

(一般式（２）中、Ｒ_１～Ｒ_１１は各々独立に、水素原子、ハロゲン原子、アルキル基、水酸基、アルコキシ基、ニトロ基、ジアルキルアミノ基、アルコキシアルキル基、または置換もしくは未置換のアリール基を表す。)

(In the general formula (2), R ₁ to R ₁₁ are each independently a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a nitro group, a dialkylamino group, an alkoxyalkyl group, or a substituted or unsubstituted aryl group. Represents a group.)

(In the general formula (3), R ₁₂ to R ₂₄ are each independently a hydrogen atom, halogen atom, alkyl group, hydroxyl group, alkoxy group, nitro group, dialkylamino group, alkoxyalkyl group, or substituted or unsubstituted aryl. Represents a group.))

In the general formula (1), X in the counter anion is preferably a fluorinated alkyl group having 1 to 3 carbon atoms in which part or all of the hydrogen atoms are substituted with fluorine atoms, and in particular, all hydrogen atoms A perfluoroalkyl group in which is substituted with a fluorine atom is particularly preferred from the viewpoint of increasing the acidity of imidic acid and improving the stability of the dye.
Specifically, for example, trifluoromethyl group, difluoromethyl group, fluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, 2-fluoroethyl group, 3,3,3-trifluoro A propyl group, a 3-fluoropropyl group, etc. can be mentioned.

The divalent hydrocarbon group represented by Y is not particularly limited, but for example, a straight chain or branched alkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a 7 to 20 carbon atoms. An arylalkylene group etc. are mentioned.
Specifically, the alkylene group includes a methylene group, an ethylene group, an n-propylene group, an isopropylene group, various butylene groups and the like, and the arylene group includes a phenylene group and a naphthylene group. Examples of the arylalkylene group include an arylmethylene group, an arylethylene group, and an arylpropylene group. Among these, an arylalkylene group having 7 to 10 carbon atoms is preferable from the viewpoint of availability of raw materials and production, and an arylmethylene group, an arylethylene group, and an arylpropylene group are particularly preferable. The arylalkylene group includes an ortho form, a meta form and a para form, but is preferably a para form from the viewpoint of no steric hindrance.

In addition, examples of the photoreactive group represented by Z include those in which the reaction proceeds through a polymerization reaction such as photo radical polymerization, photo cation polymerization, or photo anion polymerization.
Examples of the radical photopolymerization reactive group include a functional group having an ethylenically unsaturated bond (preferably an ethylenic double bond). Specifically, a vinyl group, an allyl group, a (meth) acryl group, (Meth) acryloyl group, vinyl cycloalkyl group, etc. are mentioned. Among these, a vinyl group, an allyl group, a (meth) acryl group, and a (meth) acryloyl group are preferable.
Moreover, as a photocationic polymerization reactive group, cyclic ether groups, such as an epoxy group and an oxetanyl group, a thioether group, and a vinyl ether group are mentioned, for example.
In the general formula (2), R ₁ to R ₁₁ are preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic group having 1 to 20 carbon atoms. An alkoxy group, a nitro group, a linear, branched or cyclic dialkylamino group having 2 to 20 carbon atoms, a linear, branched or cyclic alkoxyalkyl group having 2 to 20 carbon atoms, or a substitution or substitution having 4 to 20 carbon atoms An unsubstituted aryl group.

In the present specification, the aryl group represents, for example, a carbocyclic aromatic group such as a phenyl group or a naphthyl group, or a heterocyclic aromatic group such as a furyl group, a thienyl group, or a pyridyl group. In addition, the substituent of the aryl group includes a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, or a carbon number of 4 to The aryl group which may be substituted by 20 said halogen atoms, an alkyl group, and an alkoxy group etc. are mentioned. In addition, in the aryl group, these substituents may be mono-substituted or poly-substituted.

Specific examples of R ₁ to R ₁₁ include, for example, a hydrogen atom; for example, a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom;
For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, cyclohexylmethyl group, n- Octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3 , 5,5-trimethylhexyl group, n-decyl group, n-undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group Group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-eicosyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, A linear, branched or cyclic alkyl group such as 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group;

For example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, cyclopentyloxy group, n-hexyloxy group 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n -Undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyl Linear, branched or cyclic alkoxy groups such as oxy group and n-eicosyloxy group
Dialkylamino groups such as nitro group, dimethylamino group, dibutylamino group, dibutylamino group, dioctylamino group;

For example, methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-pentyloxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, n-heptyloxymethyl group, n-octyl Oxymethyl group, n-decyloxymethyl group, n-dodecyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-n-propoxyethyl group, 2-isopropoxyethyl group, 2-n-butoxy Ethyl group, 2-n-pentyloxyethyl group, 2-n-hexyloxyethyl group, 2- (2′-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group Group, 2- (2′-ethylhexyloxy) ethyl group, 2-n-decyloxyethyl group, 2-n-dodecyloxyethyl 2-n-tetradecyloxyethyl group, 2-cyclohexyloxyethyl group, 2-methoxypropyl group, 3-methoxypropyl group, 3-methoxy-2-propyl group, 3-ethoxypropyl group, 3-ethoxy-2 -Propyl group, 3-n-propoxypropyl group, 3-isopropoxypropyl group, 3-n-butoxypropyl group, 3-n-butoxy-2-propyl group, 3-n-pentyloxypropyl group, 3-n -Hexyloxypropyl group, 3- (2'-ethylbutoxy) propyl group, 3-n-octyloxypropyl group, 3- (2'-ethylhexyloxy) propyl group, 3-n-decyloxypropyl group, 3- n-dodecyloxypropyl group, 3-n-tetradecyloxypropyl group, 3-cyclohexyloxypropyl group, 4-methoxybutyl Group, 4-ethoxybutyl group, 4-n-propoxybutyl group, 4-isopropoxybutyl group, 4-n-butoxybutyl group, 4-n-hexyloxybutyl group, 4-n-octyloxybutyl group, 4-n-decyloxybutyl group, 4-n-dodecyloxybutyl group, 5-methoxypentyl group, 5-ethoxypentyl group, 5-n-propoxypentyl group, 5-n-pentyloxypentyl group, 6-methoxy Hexyl group, 6-ethoxyhexyl group, 6-isopropoxyhexyl group, 6-n-butoxyhexyl group, 6-n-hexyloxyhexyl group, 6-n-decyloxyhexyl group, 4-methoxycyclohexyl group, 7- Methoxyheptyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group, 8-methoxyoctyl group, 8-ethoxythiol group Cutyl group, 9-methoxynonyl group, 9-ethoxynonyl group, 10-methoxydecyl group, 10-ethoxydecyl group, 10-n-butoxydecyl group, 11-methoxyundecyl group, 11-ethoxyundecyl group, 12 A linear, branched or cyclic alkoxyalkyl group such as methoxydodecyl group, 12-ethoxydodecyl group, 12-isopropoxide decyl group, 14-methoxytetradecyl group, tetrahydrofurfuryl group;

For example, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2-n-propylphenyl group, 3-n-propylphenyl group 4-n-propylphenyl group, 4-isopropylphenyl group, 3-n-butylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-tert-butylphenyl group, 2-n-pentyl Phenyl group, 3-n-pentylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 3-n-hexylphenyl group, 4-n-hexylphenyl group, 4-cyclohexylphenyl group, 3-n-heptylphenyl group, 4-n-heptylphenyl group, 2-n-octylphenyl group 3-n-octylphenyl group, 4-n-octylphenyl group, 3-n-nonylphenyl group, 4-n-nonylphenyl group, 3-n-decylphenyl group, 4-n-decylphenyl group, 4- n-undecylphenyl group, 3-n-dodecylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2, 5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 3,4,5-trimethylphenyl group, 2,3,5,6-tetramethyl Phenyl group, 5-indanyl group, 1,2,3,4-tetrahydro-5-naphthyl group, 1,2,3,4-tetrahydro-6-naphthyl group,

2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-ethoxyphenyl group, 4-ethoxyphenyl group, 4-n-propoxyphenyl group, 4-isopropoxyphenyl group, 2-n-butoxy Phenyl group, 3-n-butoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 4-n-pentyloxyphenyl group, 2-n-hexyloxyphenyl group, 3-n-hexyloxy Phenyl group, 4-n-hexyloxyphenyl group, 4-cyclohexyloxyphenyl group, 4-n-heptyloxyphenyl group, 3-n-octyloxyphenyl group, 4-n-octyloxyphenyl group, 4-n- Nonyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n-undecyloxyphenyl group, -N-dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group, 2,3-dimethoxyphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 2-methoxy-4-methylphenyl group, 2-methoxy-5-methylphenyl group, 2-methyl-4-methoxyphenyl group, 3-methyl -4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group,

2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 3-trifluoromethylphenyl group, 4-triphenyl Fluoromethylphenyl group, 3-trifluoromethyloxyphenyl group, 4-trifluoromethyloxyphenyl group, 2,4-difluorophenyl group, 2,4-dichlorophenyl group, 3,4-difluorophenyl group, 3,4- Dichlorophenyl group, 3,5-difluorophenyl group, 3,5-dichlorophenyl group, 3,4,5-trifluorophenyl group, 2-methyl-4-chlorophenyl group, 2-chloro-4-methylphenyl group, 3- Chloro-4-methylphenyl group, 2-chloro-4-methoxyphenyl group, 3-methoxy -4-fluorophenyl group, 3-methoxy-4-chlorophenyl group, 3-fluoro-4-methoxyphenyl group, 2,3,4,5,6-pentafluorophenyl group, 4-phenylphenyl group, 3-phenyl Phenyl group, 4- (4′-methylphenyl) phenyl group, 4- (4′-methoxyphenyl) phenyl group, 1-naphthyl group,

2-naphthyl group, 4-methyl-1-naphthyl group, 4-ethoxy-1-naphthyl group, 6-n-butyl-2-naphthyl group, 6-methoxy-2-naphthyl group, 7-ethoxy-2-naphthyl group Group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 2-tetracenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-di-n-propyl-2- Fluorenyl group, 2-furyl group, 5-n-butyl-2-furyl group, 5-n-hexyl-2-furyl group, 5-n-octyl-2-furyl group, 2-thienyl group, 5-n- Propyl-2-thienyl group, 5-n-butyl-2-thienyl group, 5-n-hexyl-2-thienyl group, 5-n-octyl-2-thienyl group, 5-n-decyl-2-thienyl group 5-n-tridecyl- -Thienyl group, 5-phenyl-2-thienyl group, 5- (2'-thienyl) -2-thienyl group, 5- (5'-n-butyl-2'-thienyl) -2-thienyl group, 5- (5′-n-hexyl-2′-thienyl) -2-thienyl group, 5- (5′-n-decyl-2′-thienyl) -2-thienyl group, 3-thienyl group, 2-pyridyl group, Examples thereof include substituted or unsubstituted aryl groups such as a 3-pyridyl group and a 4-pyridyl group.

Next, in the general formula (3), R ₁₂ to R ₂₄ may be the same as the substituents R ₁₂ to R _{24 in the} general formula (2), and preferred ranges and specific examples thereof are also the same as those in the general formula. The same as in equation (2).
Examples of the compound represented by the general formula (1) of the present invention are shown in the following exemplified compounds 1 to 16.

The compound represented by the general formula (1) will be described below by dividing it into a cation part and an anion part. Examples of the cation moiety include structures represented by the following exemplified cation moieties 1 to 14.

Examples of the anion moiety include the structures shown by the following exemplified anion moieties 1 to 3.

[Method for producing compound of the present invention]
The compound represented by the general formula (1) of the present invention is produced by first producing the cation moiety from the corresponding raw material compound, and then ion-exchanging with the salt compound represented by the general formula (4). can do.

（一般式（４）中、Ｘは水素原子の少なくとも一部がフッ素原子に置換されていてもよいアルキル基を表し、Ｙは二価の炭化水素基を表し、Ｚは光反応性基である。Ｅは水素原子、ナトリウム、カリウム、またはトリアルキルアミンを示す。）
前記カチオン部を対応する原料化合物より製造するには、対応する原料化合物を、メタノール、エタノール、プロピルアルコールなどのアルコールと１～２倍等量の硫酸、塩酸等の酸とともに室温で処理し、硫酸塩、塩酸塩として得る。また、次いで加熱することによりアルコールに相当するカルボン酸エステル塩として得ることが出来る。カルボン酸エステル塩は単離せずに、反応液をそのまま次工程のためのカチオン部として使用できる。またカルボン酸エステル塩を製造後、そのアルコール溶液を水に排出して析出物を単離してカチオン部として用いてもよい。

(In general formula (4), X represents an alkyl group in which at least a part of hydrogen atoms may be substituted with fluorine atoms, Y represents a divalent hydrocarbon group, and Z represents a photoreactive group. E represents a hydrogen atom, sodium, potassium, or trialkylamine.)
In order to produce the cation moiety from a corresponding raw material compound, the corresponding raw material compound is treated at room temperature with an alcohol such as methanol, ethanol or propyl alcohol and an acid such as 1 to 2 times the equivalent amount of sulfuric acid or hydrochloric acid. Obtained as a salt or hydrochloride. Moreover, it can obtain as carboxylic acid ester salt corresponding to alcohol by heating next. Without isolating the carboxylic acid ester salt, the reaction solution can be used as it is as a cation moiety for the next step. Further, after the carboxylic acid ester salt is produced, the alcohol solution may be discharged into water and the precipitate may be isolated and used as a cation part.

Examples of the raw material compound include compounds represented by the following exemplified raw material compounds 1 to 14.

The step of performing ion exchange between the cation portion and the salt compound represented by the general formula (4) is performed by adding the salt compound represented by the general formula (4) to the cation portion generated in the step and stirring. .
The amount of the salt compound represented by the general formula (4) is about 1 to 3 equivalents with respect to the phthalide compound. As the reaction solvent, alcohol solvents such as methanol, ethanol and 2-propanol are preferable, halogen solvents such as chloroform, dichloromethane and dichloroethylene; aromatic solvents such as benzene, toluene and xylene; acetone, methyl ethyl ketone, methyl isobutyl ketone and the like Ketone solvents; ether solvents such as diethyl ether, dibutyl ether, 1,4-dioxane, and tetrahydrofuran; ester solvents such as ethyl acetate and butyl acetate may be used in combination. You may add the salt compound represented by General formula (4) to the reaction liquid which manufactured the said cation part.
The reaction temperature is preferably 0 ° C to 40 ° C. After the reaction, it is discharged into water and the precipitate can be removed by filtration.

[dye]
The compound represented by the general formula (1) of the present invention is suitable as a yellow dye in various applications such as water-based inks, oil-based inks, inkjet inks, color filter inks, various paints, and resin colorants. When used as a dye, it is also preferable to use a dye having another structure in combination for the purpose of toning and the like.

[ink]
The ink of the present invention contains the compound represented by the general formula (1) of the present invention, but simultaneously contains various solvents.
As various solvents, ethylene glycol monoalkyl ether acetates such as ethyl acetate, isopropyl acetate, cellosolve acetate, butyl cellosolve acetate; diethylene glycol monoalkyl ether acetates such as diethylene glycol monomethyl ether acetate, carbitol acetate, butyl carbitol acetate; propylene glycol Monoalkyl ether acetates; acetate esters such as dipropylene glycol monoalkyl ether acetates; ethylene glycol dialkyl ethers; diethylene glycol dialkyl ethers such as methyl carbitol, ethyl carbitol, and butyl carbitol; triethylene glycol dialkyl ethers Propylene glycol dialkyl ether Diether propylene glycol dialkyl ethers; ethers such as 1,4-dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; alcohols such as methanol, ethanol and butanol; benzene, toluene, xylene, Hydrocarbons such as octane and decane; Petroleum solvents such as petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha, and solvent naphtha; Lactic acid esters such as methyl lactate, ethyl lactate, and butyl lactate; Dimethylformamide, N-methylpyrrolidone, etc. Is mentioned. In particular, alkylene glycol monoalkyl ether acetates and acetate esters are preferred.
The ink of the present invention preferably further contains various resins.
Various resins will be specifically described in the section of the colored composition described later.

[Coloring composition]
The colored composition of the present invention contains at least the compound represented by the general formula (1) of the present invention and a resin.
As the resin, a thermoplastic resin, a thermosetting resin, a photosensitive resin, or the like is used. Examples of the precursor of the resin include a monomer or an oligomer that is cured by ultraviolet irradiation to generate a resin. These can be used alone or in admixture of two or more.
Examples of the thermoplastic resin include acrylic resin, polystyrene resin, polyester resin, polyurethane resin, polyamide resin, polyimide resin, chlorinated polyethylene, chlorinated polypropylene, and polyvinyl chloride.
Examples of the thermosetting resin include an epoxy resin, a melamine resin, a urea resin, and a phenol resin.
As the acrylic resin, for example, two or more monomers selected from (meth) acrylic acid, (meth) acrylic acid ester monomers, (meth) acrylic acid hydroxyalkyl monomers, and the like are used, and preferably about 3 to 5 types are used. A resin polymerized to a molecular weight of about 5,000 to 100,000 can be used. In the present specification, the term “(meth) acrylic acid” is used as a general term for acrylic acid and methacrylic acid.

Examples of the (meth) acrylic acid ester monomer include methyl (meth) acrylate, ethyl (meth) acrylate, (meth) acrylic acid-n-butyl, (meth) acrylic acid-tert-butyl, and (meth) acrylic. Acid-n-propyl and the like can be used.
Examples of the hydroxyalkyl monomer (meth) acrylate include (meth) acrylic acid, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. Such as hydroxyalkyl (meth) acrylates, ε-caprolactone condensate of the above hydroxyalkyl (meth) acrylates, polyethylene glycol mono (meth) acrylate, propylene glycol mono (meth) acrylate, (meth) acrylic acid There are -2-hydroxy-3-phenoxypropyl, pentaerythritol tri (meth) acrylate, and dipentaerythritol penta (meth) acrylate.

As the photopolymerizable monomer, a monofunctional monomer, a bifunctional monomer, a trifunctional monomer, or a polyfunctional monomer can be used. As the monofunctional monomer, nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol, etc. can be used. As the bifunctional monomer, tripropylene glycol diacrylate, Di (meth) acrylic acid tetraethylene glycol, di (meth) acrylic acid polyethylene glycol, etc. can be used. Tri (meth) acrylic acid trimethylolpropane, tri (meth) acrylic acid pentaerythritol , Tris (2-hydroxyethyl) isocyanate and the like can be used.

As a photoinitiator, there is no restriction | limiting in particular, A well-known thing can be used, It is preferable to use a triazine type compound, an imidazole type compound, or a benzophenone type compound.
Triazine compounds include 2- (p-methoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4′-methoxy-1′-naphthyl) -4,6-bis (trichloro Methyl) -s-triazine, piperonyl-s-triazine and the like can be used. Examples of imidazole compounds include 2,2′-bis- (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis- (2- And chlorophenyl) -4,4 ′, 5,5′-tetra (3,4-methylenedioxyphenyl) -1,1′-bi-1H-imidazole. As the benzophenone-based compound, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, and the like can be used. These various photopolymerization initiators may be used alone or in combination.
The colored composition of the present invention may further contain various solvents. Further, various solvents may be contained in the process of producing the colored composition, and the solvent may be removed in the final form.
Examples of the various solvents include the solvents shown in the above [Ink] section, but in addition, depending on the monomer composition of the acrylic resin used, the type of the photopolymerizable monomer, the type of the photopolymerization initiator, and the like. It can be selected as appropriate. As such a solvent, one or more kinds selected from toluene, xylene, ethyl cellosolve, ethyl cellosolve acetate, ethanol, ethyl acetate, propylene glycol monomethyl ether acetate, diglyme, cyclohexanone and the like are used.

Hereinafter, the present invention will be described more specifically with reference to examples and comparative examples, but the present invention is not limited to these examples.

Example 1: Preparation of (p-vinylphenyl) trifluoromethanesulfonylimidic acid triethylamine salt

3.00 g of trifluoromethanesulfonamide was dissolved in 30 mL of methylene chloride, and the internal temperature was cooled to 5 ° C. or lower. 5.10 g of triethylamine was added dropwise so that the internal temperature did not exceed 10 ° C., and 4.07 g of p-vinylphenylsulfonyl chloride was added at 10 ° C. or less after the completion of the addition. After stirring at 5 ° C. or lower for 1 hour, the mixture was further stirred at room temperature for 5 hours, and 100 mL of water was added to the reaction solution and stirred. The organic layer was separated, washed with water, dehydrated with magnesium sulfate, and concentrated under reduced pressure using an evaporator to obtain 8.07 g of a viscous material.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 102 (+), 314 (-)
Elemental analysis value: CHN actual measurement value (42.93%, 5.42%, 6.94%);
Theoretical value (43.26%, 5.57%, 6.73%)

Example 2: Preparation of (p-Acroyloxyphenyl) trifluoromethanesulfonylimidic acid triethylamine salt

9.0 g was obtained in the same manner as in Example 1 except that 4.96 g of p-acryloyloxyphenyl) sulfonyl chloride was used instead of 4.07 g of p-vinylphenylsulfonyl chloride of Example 1. .
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 102 (+), 358 (-)
Elemental analysis values: CHN measured values (41.65%, 5.01%, 6.11%);
Theoretical value (41.73%, 5.03%, 6.08%)

Example 3: Preparation of (p-acryloyloxybutoxyphenyl) trifluoromethanesulfonylimidic acid triethylamine salt

10.2 g was obtained in the same manner as in Example 1 except that 6.41 g of p-acryloyloxybutoxyphenylsulfonyl chloride was used instead of 4.07 g of p-vinylphenylsulfonyl chloride of Example 1.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 102 (+), 430 (-)
Elemental analysis value: CHN actual measurement value (45.00%, 5.85%, 5.11%);
Theoretical value (45.10%, 5.87%, 5.26%)

Example 4: Production of Exemplified Compound 1

Example raw material compound 1 was dissolved in 3.3 g of methanol and 50 mL of methanol, and 0.97 g of concentrated hydrochloric acid was added. 3.93 g of (p-vinylphenyl) trifluoromethanesulfonylimidic acid triethylamine salt prepared in Example 1 was added with stirring, and the mixture was further stirred at room temperature for 1 hour. The reaction solution was added to 200 mL of water, and the precipitate was collected by filtration and washed with water. Drying under reduced pressure gave 5.2 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 348 (+), 314 (-)
Elemental analysis values: CHN measured values (58.00%, 5.10%, 4.11%);
Theoretical value (57.9%, 5.02%, 4.23%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 424 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Example 5: Production of Exemplified Compound 2

The same procedure as in Example 4 was conducted, except that 2.6 g of exemplified raw material compound 2 was used instead of 3.3 g of exemplified raw material compound 1 used in Example 4, to obtain 5.1 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 278 (+), 314 (-)
Elemental analysis values: CHN measured values (54.25%, 3.90%, 4.55%);
Theoretical value (54.72%, 3.91%, 4.73%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 385 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Example 6: Production of Exemplified Compound 3

2 g of exemplified raw material compound 3 and 50 mL of methanol were dissolved, and 0.97 g of concentrated hydrochloric acid was added. 4.3 g of (p-acryloyloxyphenyl) trifluoromethanesulfonylimidic acid triethylamine salt prepared in Example 2 was added, and the mixture was further stirred at room temperature for 1 hour. The reaction solution was added to 200 mL of water, and the precipitate was collected by filtration and washed with water. Drying under reduced pressure gave 5.1 g of a yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 341 (+), 358 (-)
Elemental analysis values: CHN measured values (47.95%, 3.05%, 4.20%);
Theoretical value (48.08%, 3.17%, 4.00%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 394 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Example 7: Production of Exemplified Compound 4

Exemplified raw material compound 4 was dissolved in 2.8 g and 50 mL of methanol, and 0.97 g of concentrated hydrochloric acid was added. 5.38 g of (p-acryloyloxybutoxyphenyl) trifluoromethanesulfonylimidic acid triethylamine salt prepared in Example 3 was added, and the mixture was further stirred at room temperature for 1 hour. The reaction solution was added to 200 mL of water, and the precipitate was collected by filtration and washed with water. Drying under reduced pressure gave 5.2 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 296 (+), 430 (-)
Elemental analysis value: CHN measured value (52.65%, 4.25%, 3.65%);
Theoretical value (52.85%, 4.16%, 3.85%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 414 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Example 8: Production of Exemplified Compound 5

It processed like Example 4 except having used 2.6 g of exemplary raw material compound 5 instead of 3.3 g of exemplary raw material compound 1 used in Example 4, and obtained 4.0 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 276 (+), 314 (-)
Elemental analysis values: CHN measured values (56.90%, 4.17%, 4.59%);
Theoretical value (56.94%, 4.27%, 4.74%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 405 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Example 9: Production of Exemplified Compound 6

It processed like Example 4 except having used 2.7g of exemplary raw material compound 6 instead of 3.3g of exemplary raw material compound 1 used in Example 4, and obtained 4.3g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 292 (+), 314 (-)
Elemental analysis values: CHN measured values (55.22%, 4.19%, 4.69%);
Theoretical value (55.44%, 4.15%, 4.62%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 405 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Example 10: Production of Exemplified Compound 7

It processed like Example 4 except having used 4.6 g of exemplary raw material compound 7 instead of 3.3 g of exemplary raw material compound 1 used in Example 4, and obtained 5.3 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 488 (+), 314 (-)
Elemental analysis values: CHN measured values (62.70%, 6.69%, 3.69%);
Theoretical value (62.82%, 6.65%, 3.49%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 423 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Example 11: Production of Exemplified Compound 9

It processed like Example 4 except having used 4.0 g of exemplary raw material compound 9 instead of 3.3 g of exemplary raw material compound 1 used in Example 4, and obtained 6.5 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 430 (+), 314 (-)
Elemental analysis values: CHN measured values (58.20%, 5.19%, 7.38%);
Theoretical value (58.05%, 5.28%, 7.52%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 371 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Example 12: Production of Exemplified Compound 10

It processed like Example 4 except having used 5.1 g of exemplary raw material compound 10 instead of 3.3 g of exemplary raw material compound 1 used in Example 4, and obtained 7.2 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 542 (+), 314 (-)
Elemental analysis values: CHN measured values (60.99%, 6.55%, 6.48%);
Theoretical value (61.66, 6.47%, 6.54%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 371 nm.

Example 13: Production of Exemplified Compound 11

The same procedure as in Example 6 was conducted, except that 4.0 g of exemplified raw material compound 9 was used instead of 3.2 g of exemplified raw material compound 3 used in Example 6, to obtain 5.2 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 430 (+), 358 (-)
Elemental analysis values: CHN measured values (56.05%, 4.75%, 7.00%);
Theoretical value (56.33, 4.98%, 7.10%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 371 nm.

Example 14: Production of Exemplified Compound 12

It processed like Example 7 except having used 4.0 g of exemplary raw material compound 9 instead of 2.8 g of exemplary raw material compound 4 used in Example 7, and obtained 6.4 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 430 (+), 430 (-)
Elemental analysis values: CHN measured values (57.15%, 5.30%, 6.60%);
Theoretical value (57.20, 5.50%, 6.51%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 371 nm.

Example 15: Production of Exemplified Compound 13

It processed like Example 4 except having used 4.3 g of exemplary raw material compounds 11 instead of 3.3 g of exemplary raw material compound 1 used in Example 4, and obtained 5.0 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 458 (+), 314 (-)
Elemental analysis values: CHN measured values (59.10%, 5.55%, 7.30%);
Theoretical value (59.05%, 5.61%, 7.25%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 378 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Example 16: Production of Exemplified Compound 16

It processed like Example 4 except having used 7.2 g of exemplary raw material compound 14 instead of 3.3 g of exemplary raw material compound 1 used in Example 4, and obtained 7.0 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 767 (+), 314 (-)
Elemental analysis values: CHN measured values (66.24%, 8.25%, 5.06%);
Theoretical value (66.63%, 8.11%, 5.18%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 371 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Comparative Example 1: Production of the compound of Example 1 of JP2012-72205A

The raw material compound 1 used in Example 4 was treated in the same manner as in Example 4 except that 4.5 g of Basic Blue 7 (CI-42595 Tokyo Chemical Industry Co., Ltd.) was used instead of 3.3 g. 6.7 g of a blue powder was obtained.
From the following analysis results, it was confirmed that the compound was the target structural compound.
MS (ESI) (m / z): 478 (+), 314 (-)
Elemental analysis values: CHN measured values (63.55%, 5.92%, 7.01%);
Theoretical value (63.62%, 5.97%, 7.07%)
The absorption spectrum of the obtained compound in methanol solution was measured in the same manner as in Example 4, and λmax was 594 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

Comparative Example 2: Production of styrylquinoline-based compound disclosed in JP-A-9-512351

Instead of 3.3 g of Exemplified Raw Material Compound 1 used in Example 4, 4.6 g of Illustrative Raw Material Compound 7 and hexafluoro (p-vinylphenyl) trifluoromethanesulfonylimidic acid triethylamine salt instead of 3.93 g The same treatment as in Example 4 was carried out except that 2.7 g of sodium antimonate was used to obtain 5.3 g of yellow powder.
From the following analysis results, it was confirmed to be the target compound.
MS (ESI) (m / z): 488 (+), 235 (-)
Elemental analysis values: CHN measured values (54.55%, 6.69%, 1.89%);
Theoretical value (54.71%, 6.40%, 1.93%)
The absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). λmax was 422 nm. The results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.

(Evaluation) Solubility test The solubility test of each compound manufactured by the said Example and the comparative example was implemented as follows.
Solubility test for solvent: PGMEA = propylene glycol monomethyl ether acetate, resin solubility test: MMA = methyl methacrylate was used, and the amount of each compound dissolved in 100 parts by mass was measured at room temperature. Solubility was evaluated. The results are shown in Table 1.
A: 40 parts by mass or more dissolved. ○: Dissolved in a range of 20 parts by mass or more and less than 40 parts by mass. Δ: Dissolved in the range of 10 parts by mass or more and less than 20 parts by mass. X: Dissolution of less than 10 parts by mass. Here, “dissolution” refers to a state in which a solid cannot be seen by visual inspection.
Further, the dissolution stability test was performed by the following method.
The solution prepared by the above solubility test was allowed to stand at room temperature for 3 days, and the presence or absence of precipitation was visually confirmed.

Example 17: Production of Ink 1 7.0 g of Example Compound 1 prepared in Example 4, 6.3 g of polymethacrylic acid (weight average molecular weight 10,000) as an acrylic resin, and a combination of hydroxyethyl acrylate and methacrylic acid 6.3 g of polymer (weight average molecular weight 30,000), 3 g of 2-hydroxy-3-phenoxypropyl acrylate, 2- (p-methoxystyryl) -4,6-bis (trichloromethyl) -s-triazine Was mixed with 0.8 g and 77 g of PGMEA (propylene glycol monomethyl ether acetate), and stirred with a rotary stirrer (rotation speed: 1,000 rpm, time: 10 minutes) to produce an ink.

Examples 18 to 29: Production of inks 2 to 13 Ink 2 was prepared in the same manner as in Example 17 except that the compounds produced in Examples 5 to 16 were used instead of the exemplified compound 1 in Example 17. ~ 13 were produced.

Comparative Examples 3 and 4: Preparation of Comparative Inks 1 and 2 Comparative Inks were carried out in the same manner as in Example 17 except that the compounds prepared in Comparative Examples 1 and 2 were used instead of Exemplified Compound 1 in Example 17. 1 and 2 were produced.

Examples 30 to 42: Production of coloring compositions 1 to 13 On a glass substrate, the inks 1 to 13 produced in Examples 17 to 29 were spin-coated (3000 rpm, 10 sec), dried, and dried at 70 ° C. for 20 minutes. Pre-baked and exposed (50 mJ / cm ² ). After thoroughly washing with water, it was dried and baked at 230 ° C. for 1 hour to produce colored compositions 1 to 13.

Comparative Examples 5 and 6: Production of Comparative Colored Compositions 1 and 2 On a glass substrate, the comparative inks 1 and 2 produced in Comparative Examples 3 and 4 were spin-coated (3000 rpm, 10 sec), dried, and dried at 70 ° C. Pre-baked for 20 minutes and exposed (50 mJ / cm ² ). After sufficiently washing with water, it was dried and baked at 230 ° C. for 1 hour to produce comparative colored compositions 1 and 2.

(Evaluation) Light Resistance Test of Colored Composition For the colored compositions 1 to 13 and comparative colored compositions 1 and 2 prepared in Examples 30 to 42 and Comparative Examples 5 and 6, a 90000 xenon lamp was used. After irradiating with lux for 20 hours, the chromaticity change in the pattern image before and after irradiation, that is, ΔEab value was measured using a chromaticity meter MCPD-1000 (manufactured by Otsuka Electronics Co., Ltd.). The obtained color difference ΔEab value was evaluated based on the following criteria as an index indicating the degree of light resistance. The smaller the ΔEab value, the better the light resistance. The results are shown in Table 2.
○: ΔEab value is less than 5 Δ: ΔEab value is 5 or more and less than 10 ×: ΔEab value is 10 or more

As shown in each of the above evaluations, the compound of the present invention was excellent in solubility and dissolution stability in solvents and resins, and the colored composition containing the compound was excellent in light resistance.

The compound of the present invention has excellent light resistance, good solubility in organic solvents and resins and good dissolution stability, and is suitable for uses such as dyes, inks, and resin colorants.

Claims (5)

A compound represented by the following general formula (1).

(In General Formula (1), A ⁺ represents the following General Formula (2) or General Formula (3), X represents an alkyl group in which at least a part of hydrogen atoms may be substituted with fluorine atoms, Y represents a divalent hydrocarbon group, and Z is a photoreactive group.)

(In the general formula (2), R ₁ to R ₁₁ are each independently a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a nitro group, a dialkylamino group, an alkoxyalkyl group, or a substituted or unsubstituted aryl group. Represents a group.)

(In the general formula (3), R ₁₂ to R ₂₄ are each independently a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a nitro group, a dialkylamino group, an alkoxyalkyl group, or a substituted or unsubstituted aryl group. Represents a group.)) Y in the general formula (1) is an arylene group, Z is a group selected from a vinyl group, an allyl group, a (meth) acryl group, and a (meth) acryloyl group, and X is a perfluoroalkyl group. Item 1. The compound according to Item 1. A dye containing the compound according to claim 1 or 2. An ink containing the compound according to any one of claims 1 to 3. A colored composition comprising the system compound according to any one of claims 1 to 4 and a resin.

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