JP4474172B2 - Dye, ink, ink jet recording method, ink sheet, color toner and color filter - Google Patents

Description

  The present invention relates to a novel dye, ink, ink jet recording method, ink sheet, color toner, and color filter.

  In recent years, a material for forming a color image has been mainly used as an image recording material, and specifically, an ink jet recording material, a thermal transfer recording material, an electrophotographic recording material, a transfer halogen. Silver halide photosensitive materials, printing inks, recording pens and the like are actively used. In addition, color filters are used to record and reproduce color images in image sensors such as CCDs in photographic equipment and LCDs and PDPs in displays. These color image recording materials and color filters use so-called additive color mixing and subtractive color mixing three primary colors (dyes and pigments) to display or record full color images. In fact, there is no fast-acting dye that has absorption characteristics that can realize the above-mentioned conditions and can withstand various use conditions and environmental conditions, and improvement is strongly desired.

  The dyes used in each of the above applications must have the following properties in common. That is, it has favorable absorption characteristics in terms of color reproducibility, fastness under the environmental conditions used, for example, light resistance, heat resistance, moisture resistance, resistance to oxidizing gases such as ozone, and other chemical fastness such as sulfurous acid gas The property is good. In particular, there is a strong demand for pigments that have a good yellow hue and are robust against light, wet heat, and active gases in the environment, especially oxidizing gases such as ozone.

A typical example of the yellow dye skeleton used in ink jet recording inks is azo. As typical azo dyes, JP-A No. 2001-279145 describes a dye having an aminopyrazole skeleton, and JP-A No. 2003-277661 describes a dye having an aminopyrazole skeleton having a triazine and a pyrimidine ring. However, there is a demand for a dye that is robust against light and the active gas in the environment (NO _x , oxidizing gas such as ozone, and SO _x ).
JP 2001-279145 A JP 2003-277661 A

  An object of the present invention is to solve the conventional problems and achieve the following objects. That is, the present invention provides 1) a novel dye having absorption characteristics with excellent color reproducibility as a dye of the three primary colors and sufficient fastness to light, heat, humidity and active gases in the environment. 2) Ink for printing such as inkjet, ink sheet for thermal recording materials, color toner for electrophotography, LCD and PDP displays, CCD, etc. that give colored images and coloring materials with excellent hue and fastness Various color compositions such as color filters used in image pickup devices of 3), 3) In particular, the use of the dye has a good hue, and it is fast against light, wet heat, and active gases in the environment, particularly ozone gas. Ink jet recording ink and ink jet recording method capable of forming highly reliable images are provided. 4) Useful organic compounds or the like for industrial, agricultural, medical, academic purposes, etc. And to provide a novel dye derivative having a specific structure that can be intermediate.

（式中、Ａｒ ⁴ はベンゾチアゾール環またはチアジアゾール環を示し、Ａｒ ⁵ はチアジアゾール環を示し、Ｒ ¹ は水素原子、アルキル基、アリール基またはアルコキシ基を示す。)
Ｂ．前記Ａに記載の色素を少なくとも一種含有するインク。
Ｃ．前記Ｂに記載のインクを用いて画像形成するインクジェット記録方法。
Ｄ．前記Ａに記載の色素を少なくとも一種含むインクシート。
Ｅ．前記Ａに記載の色素を少なくとも一種含むカラートナー。
Ｆ．前記Ａに記載の色素を少なくとも一種含むカラーフィルター。
なお、本発明は、上記Ａ〜Ｆに関するものであるが、本明細書中には参考のために下記（１）〜（１０）等のその他の事項についても記載した。
（１） 下記一般式（Ａ）で表される色素。 The inventors of the present invention have studied in detail a pyrazolylazo dye derivative aiming at a dye having a good hue and high fastness to light, ozone and wet heat. The inventors have found that the above problems can be solved by the compound represented by the general formula (A 32 ), and have completed the present invention. Means for solving the problems are as following to F.
A. The pigment | dye represented by the following general formula (A32).

(In the formula, Ar ⁴ represents a benzothiazole ring or thiadiazole ring, Ar ⁵ represents a thiadiazole ring, and R ¹ represents a hydrogen atom, an alkyl group, an aryl group, or an alkoxy group.)
B. An ink containing at least one pigment according to A.
C. An inkjet recording method for forming an image using the ink according to B.
D. An ink sheet comprising at least one pigment according to A.
E. A color toner comprising at least one dye described in A.
F. A color filter comprising at least one pigment according to A.
In addition, although this invention is related to said AF, other matters, such as following (1)-(10), were described in this specification for reference.
(1) A dye represented by the following general formula (A).

(In the formula, Z represents an atomic group necessary for forming a 5- or 6-membered heterocycle including N—CR ² ═C (N═N—Ar ² ). Ar ¹ represents a group other than triazine or pyrimidine. A heterocyclic group, Ar ² represents an aryl group or a heterocyclic group, R ² represents OR ³ or NR ⁴ R ⁵ , and R ³ , R ⁴ and R ⁵ represent a hydrogen atom or a monovalent group.)
(2) The pigment | dye by which the said general formula (A) is represented by the following general formula (A1) or the following general formula (A2).

(In the formula, Ar ¹ represents a heterocyclic ring other than triazine or pyrimidine, Ar ² represents an aryl group or a heterocyclic group, R ^A1 and R ^A2 each represents a hydrogen atom or a monovalent group, and R ² represents OR ³ or NR ⁴ R ⁵ , and R ³ , R ⁴ and R ⁵ represent a hydrogen atom or a monovalent group.)
(3) The pigment | dye by which the said general formula (A) is represented with the following general formula (A3).

(In the formula, Ar ¹ represents a heterocyclic ring other than triazine or pyrimidine, Ar ² represents an aryl group or a heterocyclic group, R ¹ represents a hydrogen atom or a monovalent group, and R ² represents OR ³ or NR ^4. R ⁵ represents R ³ , R ⁴ and R ⁵ represent a hydrogen atom or a monovalent group.)
(4) The pigment | dye by which the said general formula (A3) is represented with the following general formula (A31).

(In the formula, Ar ¹ represents a heterocyclic ring other than triazine or pyrimidine, Ar ³ represents a heterocyclic group, and R ¹ represents a hydrogen atom or a monovalent group.)
(5) A dye in which the general formula (A31) is represented by the following general formula (A32).

(In the formula, Ar ⁴ represents a benzothiazole ring or a thiadiazole ring, Ar ⁵ represents a thiadiazole ring, and R ¹ represents a hydrogen atom or a monovalent group.)
(6) An ink containing at least one pigment according to any one of (1) to (5).
(7) An ink jet recording method for forming an image using the ink according to (6).

(8) An ink sheet containing at least one pigment according to any one of (1) to (5).
(9) A color toner comprising at least one dye according to any one of (1) to (5).
(10) A color filter comprising at least one pigment according to any one of (1) to (5).

  The coloring matter of the present invention has a novel coloring matter having absorption characteristics excellent in color reproducibility as a coloring matter of the three primary colors and sufficient fastness to light, heat, humidity and active gases in the environment. In addition, this dye gives colored images and coloring materials with excellent hue and fastness. Ink for printing such as inkjet, ink sheet in thermal recording material, color toner for electrophotography, LCD and PDP displays and CCD It is suitable for various colored compositions such as color filters used in imaging devices such as dyeing liquids and dyeing solutions for dyeing various fibers. In particular, the present invention provides an ink for ink jet recording and an ink jet recording method which can form an image having a good hue by use of the dye and having high fastness to light and an active gas in the environment, particularly ozone gas. Can do.

Hereinafter, the present invention will be described in detail.
[Azo dye]
The azo dye in the present invention is an azo dye represented by the general formula (A). In the general formula (A), the 5-membered or 6-membered heterocycle formed containing Z may be further condensed. Specifically, pyridone is preferable as the six-membered ring skeleton of A1, barbituric acid is preferable as the six-membered ring skeleton of A2, and pyrazole is preferable as the A3 skeleton.
Specific examples of the monovalent group of R ^A1 and R ^A2 in formula (A1) include the same substituents as the aryl group described later, and are preferably an alkyl group, a carbamoyl group, an alkoxycarbonyl group, or a cyano group. .
Hereinafter, the general formulas (A), (A1), (A2), (A3), (A31), and (A32) will be described in detail.
R ² in formulas (A), (A1), (A2), and (A3) represents OR ³ or NR ⁴ R ⁵ , and monovalent groups of R ³ , R ^4, and R ⁵ are aryls described later. It is the same as the substituent of the group.
The heterocyclic group represented by Ar ¹ in the formulas (A), (A1), (A2), (A3), and (A31) is preferably a 5-membered or 6-membered ring, which is further condensed You may do it. Further, it may be an aromatic heterocycle or a non-aromatic heterocycle. For example, pyridine, pyrazine, pyridazine, quinoline, isoquinoline, quinazoline, cinnoline, phthalazine, quinoxaline, pyrrole, indole, furan, benzofuran, thiophene, benzothiophene, pyrazole, imidazole, benzimidazole, triazole, oxazole, benzoxazole, thiazole, benzo Examples include thiazole, isothiazole, benzisothiazole, thiadiazole, isoxazole, benzisoxazole, pyrrolidine, piperidine, piperazine, imidazolidine and thiazoline. Among them, an aromatic heterocyclic group is preferable, and preferable examples thereof are exemplified in the same manner as described above. Can be mentioned. Most preferred are benzothiazole and thiadiazole. They may have a substituent, and examples of the substituent are the same as those of the aryl group described later.

The heterocyclic group represented by Ar ² in formulas (A), (A1), (A2), and (A3) is the same as the heterocyclic group for Ar ¹ . The aryl group represented by Ar ² includes a substituted or unsubstituted aryl group. As the substituted or unsubstituted aryl group, an aryl group having 6 to 30 carbon atoms is preferable. Examples of substituents include halogen atoms, alkyl groups, cycloalkyl groups, aralkyl groups, alkenyl groups, alkynyl groups, aryl groups, heterocyclic groups, cyano groups, hydroxyl groups, nitro groups, carboxyl groups (even in salt form). Good), alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy, amino group (including alkylamino group and arylamino group), acylamino Group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group , Sulfo group (may be in the form of a salt), alkyl and arylsulfinyl group, alkyl and arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphine group Examples include a ruoxy group, a phosphinylamino group, and a silyl group.

This will be described in more detail. The halogen atom represents a chlorine atom, a bromine atom or an iodine atom, and the alkyl group includes a substituted or unsubstituted alkyl group. The substituted or unsubstituted alkyl group is preferably an alkyl group having 1 to 30 carbon atoms. Examples of the substituent include the same substituents as the aryl group. Of these, a hydroxyl group, an alkoxy group, a cyano group, and a halogen atom, a sulfo group (which may be a salt form) and a carboxyl group (which may be a salt form) are preferable. Examples of the alkyl group include methyl, ethyl, butyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl, hydroxyethyl, cyanoethyl and 4-sulfobutyl.
The cycloalkyl group includes a substituted or unsubstituted cycloalkyl group. The substituted or unsubstituted cycloalkyl group is preferably a cycloalkyl group having 5 to 30 carbon atoms. Examples of the substituent include the same substituents as the aryl group. Examples of the cycloalkyl group include cyclohexyl, cyclopentyl, and 4-n-dodecylcyclohexyl.

Aralkyl groups include substituted or unsubstituted aralkyl groups. As the substituted or unsubstituted aralkyl group, an aralkyl group having 7 to 30 carbon atoms is preferable. Examples of the substituent include the same substituents as the aryl group. Examples of the aralkyl include benzyl and 2-phenethyl.
An alkenyl group represents a linear, branched, or cyclic substituted or unsubstituted alkenyl group. Preferable examples include substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms, such as vinyl, allyl, prenyl, geranyl, oleyl, 2-cyclopenten-1-yl, 2-cyclohexen-1-yl and the like.

The alkynyl group is a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, and examples thereof include ethynyl and propargyl.
The aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as phenyl, p-tolyl, naphthyl, m-chlorophenyl, o-hexadecanoylaminophenyl.
The heterocyclic group is a monovalent group in which one hydrogen atom is removed from a 5- or 6-membered substituted or unsubstituted aromatic or non-aromatic heterocyclic compound, and more preferably, it has 3 to 30 carbon atoms. It is a 5- or 6-membered aromatic heterocyclic group. For example, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl, morpholino.

  The alkoxy group includes a substituted or unsubstituted alkoxy group. The substituted or unsubstituted alkoxy group is preferably an alkoxy group having 1 to 30 carbon atoms. Examples of the substituent include the same substituents as the aryl group. Examples of the alkoxy group include methoxy, ethoxy, isopropoxy, n-octyloxy, methoxyethoxy, hydroxyethoxy and 3-carboxypropoxy.

The aryloxy group is a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms such as phenoxy, 2-methylphenoxy, 4-t-butylphenoxy, 3-nitrophenoxy, 2-tetradecanoylaminophenoxy. .
The silyloxy group is a silyloxy group having 3 to 20 carbon atoms, for example, trimethylsilyloxy, t-butyldimethylsilyloxy.
The heterocyclic oxy group is a substituted or unsubstituted heterocyclic oxy group having 2 to 30 carbon atoms such as 1-phenyltetrazol-5-oxy and 2-tetrahydropyranyloxy.
The acyloxy group is a formyloxy group, a substituted or unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyloxy group having 6 to 30 carbon atoms, such as formyloxy, acetyloxy, pivaloyloxy, stearoyl Oxy, benzoyloxy and p-methoxyphenylcarbonyloxy.
The carbamoyloxy group is a substituted or unsubstituted carbamoyloxy group having 1 to 30 carbon atoms, such as N, N-dimethylcarbamoyloxy, N, N-diethylcarbamoyloxy, morpholinocarbonyloxy, N, N-di-n-. Octylaminocarbonyloxy, Nn-octylcarbamoyloxy.
The alkoxycarbonyloxy group is a substituted or unsubstituted alkoxycarbonyloxy group having 2 to 30 carbon atoms, such as methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxycarbonyloxy, n-octylcarbonyloxy.
The aryloxycarbonyloxy group is a substituted or unsubstituted aryloxycarbonyloxy group having 7 to 30 carbon atoms, for example, phenoxycarbonyloxy, p-methoxyphenoxycarbonyloxy, pn-hexadecyloxyphenoxycarbonyloxy.

The amino group is a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, such as amino, methylamino, dimethylamino, anilino, N-methyl- Anilino, diphenylamino, hydroxyethylamino, carboxyethylamino, sulfoethylamino, 3,5-dicarboxyanilino.
The acylamino group is a formylamino group, a substituted or unsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylcarbonylamino group having 6 to 30 carbon atoms, such as formylamino, acetylamino, pivaloylamino, Lauroylamino, benzoylamino, 3,4,5-tri-n-octyloxyphenylcarbonylamino.
The aminocarbonylamino group is a substituted or unsubstituted aminocarbonylamino having 1 to 30 carbon atoms, such as carbamoylamino, N, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino.
The alkoxycarbonylamino group is a substituted or unsubstituted alkoxycarbonylamino group having 2 to 30 carbon atoms, such as methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino. It is.
The aryloxycarbonylamino group is a substituted or unsubstituted aryloxycarbonylamino group having 7 to 30 carbon atoms, for example, phenoxycarbonylamino, p-chlorophenoxycarbonylamino, mn-octyloxyphenoxycarbonylamino.
The sulfamoylamino group is a substituted or unsubstituted sulfamoylamino group having 0 to 30 carbon atoms, such as sulfamoylamino, N, N-dimethylaminosulfonylamino, Nn-octylaminosulfonylamino. .
Alkyl and arylsulfonylamino groups are substituted or unsubstituted alkylsulfonylamino having 1 to 30 carbon atoms, substituted or unsubstituted arylsulfonylamino having 6 to 30 carbon atoms, such as methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino 2,3,5-trichlorophenylsulfonylamino, p-methylphenylsulfonylamino.

The alkylthio group is a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, for example, methylthio, ethylthio, n-hexadecylthio.
The arylthio group is a substituted or unsubstituted arylthio having 6 to 30 carbon atoms, such as phenylthio, p-chlorophenylthio, m-methoxyphenylthio.
The heterocyclic thio group is a substituted or unsubstituted heterocyclic thio group having 2 to 30 carbon atoms, such as 2-benzothiazolylthio, 1-phenyltetrazol-5-ylthio.

The sulfamoyl group is a substituted or unsubstituted sulfamoyl group having 0 to 30 carbon atoms, such as N-ethylsulfamoyl, N- (3-dodecyloxypropyl) sulfamoyl, N, N-dimethylsulfamoyl, N-acetylsulfamoyl. Famoyl, N-benzoylsulfamoyl, N- (N′-phenylcarbamoyl) sulfamoyl).
Alkyl and arylsulfinyl groups are substituted or unsubstituted alkylsulfinyl groups having 1 to 30 carbon atoms, substituted or unsubstituted arylsulfinyl groups having 6 to 30 carbon atoms, such as methylsulfinyl, ethylsulfinyl, phenylsulfinyl, p-methylphenyl Sulfinyl.
The alkyl and arylsulfonyl groups are substituted or unsubstituted alkylsulfonyl groups having 1 to 30 carbon atoms, substituted or unsubstituted arylsulfonyl groups having 6 to 30 carbon atoms such as methylsulfonyl, ethylsulfonyl, phenylsulfonyl, p-methylphenyl. Sulfonyl.

  The acyl group is a formyl group, a substituted or unsubstituted alkylcarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 7 to 30 carbon atoms, and a substituted or unsubstituted carbon atom having 4 to 30 carbon atoms. A heterocyclic carbonyl group bonded to a carbonyl group, for example, acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, pn-octyloxyphenylcarbonyl, 2-pyridylcarbonyl, 2-furylcarbonyl.

The aryloxycarbonyl group is a substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms, for example, phenoxycarbonyl, o-chlorophenoxycarbonyl, m-nitrophenoxycarbonyl, pt-butylphenoxycarbonyl.
The alkoxycarbonyl group is a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, for example, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl.
The carbamoyl group is a substituted or unsubstituted carbamoyl having 1 to 30 carbon atoms such as carbamoyl, N-methylcarbamoyl, N, N-dimethylcarbamoyl, N, N-di-n-octylcarbamoyl, N- (methylsulfonyl). Carbamoyl.

The phosphino group is a substituted or unsubstituted phosphino group having 2 to 30 carbon atoms, such as dimethylphosphino, diphenylphosphino, methylphenoxyphosphino.
The phosphinyl group is a substituted or unsubstituted phosphinyl group having 2 to 30 carbon atoms, for example, phosphinyl, dioctyloxyphosphinyl, diethoxyphosphinyl.
The phosphinyloxy group is a substituted or unsubstituted phosphinyloxy group having 2 to 30 carbon atoms, for example, diphenoxyphosphinyloxy, dioctyloxyphosphinyloxy.
The phosphinylamino group is a substituted or unsubstituted phosphinylamino group having 2 to 30 carbon atoms, such as dimethoxyphosphinylamino, dimethylaminophosphinylamino.
The silyl group is a substituted or unsubstituted silyl group having 3 to 30 carbon atoms such as trimethylsilyl, t-butyldimethylsilyl, and phenyldimethylsilyl.

  Among the substituents of the aryl group, those having a hydrogen atom may be removed and further substituted with the above group. Examples of such functional groups include an alkylcarbonylaminosulfonyl group, an arylcarbonylaminosulfonyl group, an alkylsulfonylaminocarbonyl group, and an arylsulfonylaminocarbonyl group. Examples thereof include methylsulfonylaminocarbonyl, p-methylphenylsulfonylaminocarbonyl, acetylaminosulfonyl, and benzoylaminosulfonyl groups.

The monovalent group represented by R ¹ , R ³ , R ⁴ and R ⁵ in the general formula (A3) is the same as the above-described substituent of the aryl group. R ¹ is preferably an alkyl group, an aryl group or an alkoxy group, more preferably t-butyl, phenyl, ethoxy or methyl. R ³ , R ⁴ and R ⁵ are preferably a hydrogen atom and an alkyl group.

The general formula (A3) is more preferably the general formula (A31). Ar ¹ and R ¹ in the general formula (A31) is the general formula Ar ¹ and R ¹ of (A3) are each the same. Ar ^{3 in} formula (A31) is a heterocyclic group, and is the same as the heterocyclic group of Ar ² .

The general formula (A3) is more preferably the general formula (A32). Ar ⁴ is a benzothiazole ring or thiadiazole ring, and Ar ⁵ is a thiadiazole ring.
The dye of the present invention may form a bisazo dye via a linking group. The linking group is a divalent linking group, an alkylene group (eg, methylene, ethylene, propylene, butylene, pentylene), an alkenylene group (eg, ethenylene, propenylene), an alkynylene group (eg, ethynylene, propynylene), Arylene groups (eg, phenylene, naphthylene), divalent heterocyclic groups (eg, 6-chloro-1,3,5-triazine-2,4-diyl group, pyrimidine-2,4-diyl group, quinoxaline-2,3-diyl group, pyridazine-3, 6-diyl), - O -, - CO -, - NR- (R is a hydrogen atom, an alkyl group or an aryl group), - S -, - SO 2 -, - SO- or preferably a combination thereof .
The alkylene group, alkenylene group, alkynylene group, arylene group, divalent heterocyclic group, R alkyl group or aryl group may have a substituent. Examples of the substituent are the same as those of the aryl group. The alkyl group and aryl group of R are as defined above.
More preferably, an alkylene group having 10 or less carbon atoms, an alkenylene group having 10 or less carbon atoms, an alkynylene group having 10 or less carbon atoms, an arylene group having 6 to 10 carbon atoms, -S-, -SO-, -SO _2- Or it is more preferable that they are a combination thereof.
The total number of carbon atoms in the divalent linking group is preferably 0 to 50, more preferably 0 to 30, and most preferably 0 to 10.

In the present invention, when the compounds represented by the general formulas (A), (A1), (A2), (A3), (A31) and (A32) require hydrophilicity, two or more in the molecule It is preferable to have 2 to 10 hydrophilic groups, more preferably 2 to 10 hydrophilic groups, and particularly preferably 3 to 6 hydrophilic groups. However, when water is not used as a medium, it does not have to have a hydrophilic group.
Any hydrophilic group may be used as long as it is an ionic dissociation group. Specific examples include a sulfo group, a carboxyl group (including salts thereof), a hydroxyl group (may be a salt), a phosphono group (may be a salt), and an ammonium group. A sulfo group, a carboxyl group, and a hydroxyl group (including salts thereof) are preferable.
The dyes represented by the general formulas (A), (A1), (A2), (A3), (A31) and (A32) have a maximum of 380 to 490 nm in H ₂ O from the viewpoint of color reproducibility. It preferably has an absorption wavelength (λmax), more preferably has a λmax of 400 to 480 nm, and particularly preferably has a λmax of 420 to 460 nm.

  Specific examples of the dyes represented by the general formulas (A), (A1), (A2), and (A3) are shown below, but the dyes used in the present invention are not limited to the following examples. .

As a representative example of the dye of the present invention, a synthesis method of dye 2 will be described. Other dyes can be synthesized similarly.
Applications of the dye of the present invention include image recording materials for forming images, particularly color images. Specifically, the recording materials include inkjet recording materials described in detail below, thermal recording materials, and pressure sensitive materials. There are recording materials, recording materials using electrophotographic methods, transfer type silver halide photosensitive materials, printing inks, recording pens, etc., preferably ink jet recording materials, thermal recording materials, recording materials using electrophotography, An ink jet recording material is preferable.
It can also be applied to solid-state imaging devices such as CCDs, color filters for recording and reproducing color images used in displays such as LCDs and PDPs, and dyeing solutions for dyeing various fibers.
The coloring matter of the present invention is used after adjusting physical properties such as solubility, dispersibility, and heat mobility suitable for the application with a substituent. Further, the coloring matter of the present invention can be used in a dissolved state, an emulsified dispersed state, or a solid dispersed state depending on the system used.

[ink]
The ink of the present invention means an ink containing at least one kind of the coloring matter of the present invention. The ink of the present invention can contain a medium, but when a solvent is used as the medium, it is particularly suitable as an ink for inkjet recording. The ink of the present invention can be produced by using a lipophilic medium or an aqueous medium as a medium and dissolving and / or dispersing the dye of the present invention in the medium. Preferably, an aqueous medium is used. The ink of the present invention includes an ink composition excluding a medium. If necessary, other additives are contained within a range that does not impair the effects of the present invention. Other additives include, for example, anti-drying agents (wetting agents), anti-fading agents, emulsion stabilizers, penetration enhancers, ultraviolet absorbers, preservatives, anti-fungal agents, pH adjusters, surface tension adjusters, Known additives (described in JP-A No. 2003-306623) such as a foaming agent, a viscosity modifier, a dispersant, a dispersion stabilizer, a rust inhibitor, and a chelating agent can be used. These various additives are directly added to the ink liquid in the case of water-soluble ink. When the oil-soluble dye is used in the form of a dispersion, it is generally added to the dispersion after the preparation of the dye dispersion, but it may be added to the oil phase or the aqueous phase at the time of preparation.

  When the dye [← compound] of the present invention is dispersed in an aqueous medium, it is oil-soluble with the dye as described in JP-A-11-286637, Japanese Patent Application Nos. 2000-78491, 2000-80259 and 2000-62370. Colored fine particles containing polymer are dispersed in an aqueous medium or dissolved in a high boiling point organic solvent as in Japanese Patent Application Nos. 2000-78454, 2000-78491, 2000-203856, 2000-203857 It is preferable to disperse the dye of the present invention in an aqueous medium. The specific method for dispersing the dye of the present invention in an aqueous medium, the oil-soluble polymer to be used, the high-boiling organic solvent, the additive, and the amount used thereof are preferably those described in the aforementioned patent. it can. Alternatively, the azo dye may be dispersed in a fine particle state as a solid. At the time of dispersion, a dispersant or a surfactant can be used. Dispersing devices include simple stirrer, impeller stirring method, in-line stirring method, mill method (for example, colloid mill, ball mill, sand mill, attritor, roll mill, agitator mill, etc.), ultrasonic method, high-pressure emulsification dispersion method (high-pressure homogenizer) Specific examples of commercially available devices include gorin homogenizers, microfluidizers, DeBEE2000, and the like. In addition to the above-mentioned patents, the method for preparing the ink for ink jet recording is described in JP-A Nos. 5-148436, 5-295212, 7-97541, 7-82515, and 7-118584. Details are described in Japanese Laid-Open Patent Publication No. 11-286637 and Japanese Patent Application No. 2000-87539, and can also be used for preparing the ink for ink jet recording of the present invention.

  As the aqueous medium, a mixture containing water as a main component and optionally adding a water-miscible organic solvent can be used. As examples of the water-miscible organic solvent, those described in JP-A No. 2003-306623 can be used. In addition, the said water miscible organic solvent may use 2 or more types together.

  The pigment [← compound] of the present invention is preferably contained in an amount of 0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, in 100 parts by weight of the inkjet recording ink of the present invention. It is more preferable to contain 0.5-9 parts by mass. Further, in the inkjet ink of the present invention, other pigments may be used in combination with the pigment [← compound] of the present invention. When two or more kinds of dyes are used in combination, the total content of the dyes is preferably within the above range.

  The ink of the present invention can be used not only for monochromatic image formation but also for full color image formation. In order to form a full color image, a magenta color ink, a cyan color ink, and a yellow color ink can be used, and a black color ink may be further used to adjust the color tone.

  Furthermore, the ink for inkjet recording in the present invention can simultaneously use another yellow dye in addition to the coloring matter in the present invention. As the applicable yellow dye, applicable magenta dye, and applicable cyan dye, any dye can be used, but each dye described in paragraph Nos. 0090 to 0092 of JP-A No. 2003-306623 can be used. Applicable black materials include disazo, trisazo, tetraazo dyes, and carbon black dispersions.

[Inkjet recording method]
In the ink jet recording method of the present invention, energy is supplied to the ink for ink jet recording, and a known image receiving material, that is, plain paper, resin-coated paper, such as JP-A-8-169172, JP-A-8-27693, JP-A-2-276670, JP-A-7-276789, JP-A-9-323475, JP-A-62-238783, JP-A-10-153989, JP-A-10-217473, JP-A-10-235995 10-337947, 10-217597, 10-337947, etc. Form images on inkjet paper, film, electrophotographic co-paper, fabric, glass, metal, ceramics, etc. To do. In addition, the description of Paragraph Nos. 0093 to 0105 of JP-A No. 2003-306623 can be applied as the ink jet recording method of the present invention.

  When forming an image, a polymer latex compound may be used in combination for the purpose of imparting glossiness or water resistance or improving weather resistance. The timing of applying the latex compound to the image receiving material may be before, after, or simultaneously with the application of the colorant. Therefore, even if the addition place is in the image receiving paper, It may be in ink or may be used as a liquid material of polymer latex alone. Specifically, the methods described in Japanese Patent Application Nos. 2000-363090, 2000-315231, 2000-354380, 2000-343944, 2000-268952, 2000-299465, 2000-299465, 2000-297365 are preferably used. it can.

[Color toner]
The content of the pigment of the present invention in 100 parts by weight of the color toner of the present invention is not particularly limited, but it is preferably 0.1 parts by weight or more, more preferably 1 to 20 parts by weight, and 2 to 10 parts by weight. Most preferably it contains.
As the binder resin for a color toner into which the coloring matter of the present invention is introduced, all commonly used binders can be used. Examples thereof include styrene resin, acrylic resin, styrene / acrylic resin, and polyester resin.
Inorganic fine powders and organic fine particles may be externally added to the toner for the purpose of improving fluidity and controlling charging. Silica fine particles and titania fine particles whose surface is treated with an alkyl group-containing coupling agent or the like are preferably used. These have a number average primary particle diameter of preferably 10 to 500 nm, and more preferably 0.1 to 20% by mass in the toner.

  As the release agent, all conventionally used release agents can be used. Specific examples include olefins such as low molecular weight polypropylene, low molecular weight polyethylene, and ethylene-propylene copolymer, microcrystalline wax, carnauba wax, sazole wax, and paraffin wax. These addition amounts are preferably 1 to 5% by mass in the toner.

  The charge control agent may be added as necessary, but is preferably colorless from the viewpoint of color development. Examples thereof include those having a quaternary ammonium salt structure and those having a calixarene structure.

  As the carrier, either an uncoated carrier composed only of magnetic material particles such as iron and ferrite, or a resin-coated carrier whose magnetic material particle surface is coated with a resin or the like may be used. The average particle size of the carrier is preferably 30 to 150 μm in terms of volume average particle size.

  The image forming method to which the toner of the present invention is applied is not particularly limited. For example, a method of forming a color image after repeatedly forming a color image on a photoconductor to form an image, or a method of forming an image on a photoconductor. For example, the image may be transferred to an intermediate transfer member and the like, and a color image may be formed on the intermediate transfer member and then transferred to an image forming member such as paper to form a color image.

[Thermal recording (transfer) material]
The heat-sensitive recording material is composed of an ink sheet in which the dye of the present invention is coated on a support together with a binder, and an image receiving sheet that fixes the dye transferred in response to the thermal energy applied from the thermal head according to the image recording signal. Is done. The ink sheet is prepared by dissolving the compound of the present invention in a solvent together with a binder, or by dispersing in fine particles in a solvent, coating the ink on a support, and drying appropriately. Can be formed. The amount of ink applied on the support is not particularly limited, but is preferably 30 to 1000 mg / m ² . As the preferred binder resin, ink solvent, support, and image receiving sheet, those described in JP-A-7-137466 can be preferably used.

  In order to apply the heat-sensitive recording material to a heat-sensitive recording material capable of full-color image recording, a cyan ink sheet containing a heat-diffusible cyan dye capable of forming a cyan image, and heat diffusion capable of forming a magenta image. It is preferable to form a magenta ink sheet containing a reactive magenta dye and a yellow ink sheet containing a heat diffusible yellow dye capable of forming a yellow image by sequentially coating the support. In addition, an ink sheet containing a black image forming substance may be further formed as necessary.

[Color filter]
As a color filter forming method, a pattern is first formed with a photoresist and then dyed, or disclosed in JP-A-4-163552, JP-A-4-128703, and JP-A-4-175753. Thus, there is a method of forming a pattern with a photoresist to which a dye is added. Any of these methods may be used as a method used when introducing the dye of the present invention into a color filter. Preferred methods are described in JP-A-4-175753 and JP-A-6-35182. The positive resist composition comprising a thermosetting resin, a quinonediazide compound, a cross-linking agent, a dye and a solvent, and after coating on a substrate, exposing through a mask and developing the exposed portion. Then, a positive resist pattern is formed, the positive resist pattern is exposed on the entire surface, and then the exposed positive resist pattern is cured, and a color filter forming method can be mentioned. In addition, a black matrix is formed according to a conventional method, and an RGB primary color system or Y, M, C complementary color system color filter can be obtained. In the case of a color filter, although there is no restriction | limiting of the usage-amount of pigment | dye, 0.1-50 mass% is preferable.

  Regarding the thermosetting resin, quinonediazide compound, crosslinking agent, and solvent used in this case, and those used, those described in the above-mentioned patent documents can be preferably used.

[Example]
EXAMPLES Hereinafter, although an Example demonstrates this invention, this invention is not limited to this.

  A synthesis example of the dye 3-2 will be described.

1. 3.2 ml of pyridine was added to 20 ml of (a) 5.36 g, (b) 3.62 g and N, N-dimethylacetamide, and the mixture was stirred at room temperature for 2 hours. H ₂ O and HCl were added and the precipitated crystals were separated by filtration to obtain 7.7 g of (c).
2. (C) 4.5 g of hydrazine was added to 7.5 g and 35 ml of H ₂ O, and the mixture was stirred at 70 ° C. for 1 hour. After acidification, filtration was performed to obtain 3.8 g of (d).
3. (D) 0.73 g of (e) and 1 ml of AcOH were added to 2.4 g and 20 ml of MeOH, and the mixture was refluxed for 10 hours. After concentration, filtration was performed to obtain 2.4 g of (f).
4). (G) 1 g and 10 ml of phosphoric acid were cooled, 0.4 g of NaNO ₂ was added, and the mixture was stirred for 1 hour. (F) The diazo solution prepared previously was added to a solution of 2.4 g and MeOH 50 ml and stirred for 1 hour. The crystals were separated and subjected to column chromatography using Sephadex to obtain 1.8 g of dye 3-2.
λmax 436.3 nm (H ₂ O), ε: 2.63 × 10 ⁴ (dm ³ .cm / mol)
Other dyes can be synthesized in the same manner. The synthesized dyes are shown in Table 1.

After adding ultrapure water (resistance value of 18 MΩ or more) to the following components to make 1 liter, the mixture was stirred for 1 hour while heating at 30 to 40 ° C. Thereafter, it was filtered under reduced pressure with a microfilter having an average pore diameter of 0.25 μm to prepare a yellow ink liquid Y-101. The viscosity of the ink liquid was 4.1 mPa · S, and the surface tension was 31 mN / m.
[Yellow ink Y-101 prescription]
(Solid content)
Yellow dye 3-2 of the present invention 40 g / l
Proxel (made by Zeneca) 1.5g / l
Urea 20g / l
(Liquid component)
Triethylene glycol monobutyl ether (DGB) 100g / l
Glycerin (GR) 115g / l
Triethylene glycol (TEG) 100g / l
2-pyrrolidone 35g / l
Triethanolamine (TEA) 8g / l
Surfynol STG (SW) 10g / l
Ink liquid Y-102 was produced in the same manner as ink liquid Y-101, except that the coloring matter was changed as shown in Table 2 below.
At this time, an ink liquid 101 was prepared using the comparative dye a in Table 2 as a comparative ink liquid.
When the dye was changed, the dye was used so that the amount of the dye added was equimolar with respect to the ink liquid Y-101.
The following evaluations were performed on the inkjet inks of the above Examples (Ink Liquids Y101 and 102) and Comparative Example (Ink Liquid 101). The results are shown in Table 2.
In Table 2, “color tone”, “light resistance”, “ozone resistance (gas) resistance” and “heat fastness” are determined by loading each inkjet ink into a yellow ink cartridge of an inkjet printer PM920C manufactured by EPSON. Then, a yellow single-color image pattern and a gray image pattern whose density changed stepwise were printed. The image-receiving sheet was printed on Epson inkjet printer photographic paper <glossy>, and the image quality and image fastness were evaluated.
(Evaluation experiment)
<Color tone>
The color tone was visually evaluated in three stages: A (best), B (good), and C (poor).
<Light resistance>
After measuring the image density Ci immediately after printing with a reflection densitometer (X-rite 310TR), the image was irradiated with xenon light (85,000 lux) for 7 days using an Atlas weather meter, and the image density again. Cf was measured and the dye residual ratio Cf / Ci × 100 was determined and evaluated. The afterimage rate of the dye is evaluated at three points of reflection density of 1, 1.5, and 2. A is the case where the dye remaining rate is 70% or more at any concentration, and B is the case where the reflection rate is less than 70%. When the concentration was less than 70%, C was designated.
<Ozone resistance (gas) resistance>
The photo glossy paper on which the image has been formed is left in a box where the ozone gas concentration is set to 5 ppm for 10 days, and the image density before and after being left under ozone gas is measured using a reflection densitometer (X-rite 310TR) The residual rate was evaluated. The reflection density was measured at three points of 1, 1.5 and 2.0. The ozone gas concentration in the box was set using an ozone gas monitor (model: OZG-EM-01) manufactured by APPLICS.
Evaluation was made in three stages, with A being a dye residual ratio of 80% or more at any concentration, A being 1 or 2 points being less than 80% B, and C being less than 70% at all concentrations.
<Thermal fastness>
The density before and after storing the sample for 10 days at 80 ° C. and 70% RH was measured with a reflection densitometer (X-rite 310TR), and the dye residual ratio was determined and evaluated. The afterimage rate of the dye is evaluated at three points of reflection density of 1, 1.5, and 2. A is the case where the dye residual rate is 90% or more at any concentration, and B is the case where the reflection rate is less than 90%. The concentration of less than 90% was defined as C.
The obtained results are shown in Table 2.

  As is clear from the results in Table 2, it can be seen that the system using the ink of the present invention is excellent in all performance.

  An image of the same ink prepared in Example 2 was printed on the inkjet paper photo glossy paper “Image Aya” manufactured by Fuji Photo Film with the same machine of Example 2, and the same evaluation as in Example 1 was performed. Similar results to 2 were obtained.

(Preparation of ink liquid D)
2.5 g of the dye 3-10 of the present invention, 7.04 g of sodium dioctylsulfosuccinate, 4.22 g of the following high boiling point organic solvent (s-2), 5.63 g of the following high boiling point organic solvent (s-11), and ethyl acetate Dissolve in 50 ml at 70 ° C. 500 ml of deionized water was added to this solution while stirring with a magnetic stirrer to prepare an oil-in-water type coarse particle dispersion. Next, this coarse particle dispersion was micronized by passing it through a microfluidizer (MICROFLUIDEX INC) five times at a pressure of 600 bar. Further, the resulting emulsion was desolvated with a rotary evaporator until the odor of ethyl acetate disappeared. Ink D was prepared by adding 140 g of diethylene glycol, 50 g of glycerol, 7 g of SURFYNOL 465 (Air Products & Chemicals) and 900 ml of deionized water to the fine emulsion of the hydrophobic dye thus obtained. This ink had a pH of 8.5, a viscosity of 4.1 mPa · S, and a surface tension of 33 mN / m.

(Preparation of ink liquid 103)
Ink liquid 103 was prepared in the same manner as ink liquid D, except that the dye of the present invention in ink liquid D was changed to an equimolar amount of the comparative dye shown in Table 3 below. The pH, viscosity, and surface tension of the ink liquid were the same as those of the ink liquid D.

(Image recording and evaluation)
The following evaluation was performed on the ink liquid D and the comparative ink liquid 103. The results are shown in Table 3 below.
In Table 3, the contents of “color tone”, “light resistance”, “ozone gas resistance” and “heat resistance” are the same as those described in the first embodiment.

  As is apparent from Table 3, the inkjet ink of the present invention was excellent in color tone and excellent in light resistance, ozone resistance and heat resistance.

  The same ink produced in Example 4 was printed on Fuji Photo Film inkjet paper photo glossy paper “Image” with the same machine of Example 4, and the same evaluation as in Example 4 was performed. Similar results to 4 were obtained.

  3 parts by mass of the dye 3-7 of the present invention, 100 parts by mass of a resin for a toner [styrene-acrylic acid ester copolymer; trade name Hymer TB-1000F (manufactured by Sanyo Kasei)] by a ball mill and heated to 150 ° C. After cooling, the mixture was cooled, coarsely pulverized with a hammer mill, and then finely pulverized with an air jet type pulverizer. Further, classification was performed to select 1 to 20 micron, and a toner was obtained. To 10 parts of this toner, 900 parts by mass of carrier iron powder (trade name: EFV250 / 400; manufactured by Nippon Iron Powder) was uniformly mixed to obtain a developer. Similarly, a sample was prepared in the same manner except that 3 parts by mass of the colorant shown in Table 4 was used. Using these developers, copying was performed with a dry plain paper electrophotographic copying machine [trade name NP-5000; manufactured by Canon Inc.].

  In the evaluation test, a reflection image (an image on paper) and a transmission image (an OHP image) were produced on the paper and the OHP, respectively, by the above-described image forming method using the developer using the color toner of the present invention. Carried out. The toner adhesion amount was evaluated in the range of 0.7 ± 0.05 (mg / cm 2).

  The obtained image was evaluated for hue and light fastness. The hue was visually evaluated in three stages: best, good and poor. The evaluation results are shown in Table 4 below. In Table 4 below, o indicates that the hue is the best; Δ indicates that the hue is good, and x indicates that the hue is poor. Regarding the light fastness, after measuring the image density Ci immediately after recording, the image was irradiated with xenon light (85,000 lux) for 5 days using a weather meter (Atlas C.165), and the image was again displayed. The density Cf was measured, and the dye residual ratio ({(Ci-Cf) / Ci} × 100%) was calculated from the difference in image density before and after the xenon light irradiation and evaluated. The image density was measured using a reflection densitometer (X-Rite 310TR). The evaluation results are shown in Table 3 below. In Table 4 below, the case where the dye residual ratio is 90% or more is indicated by ◯, the case where it is 90-80% is indicated by Δ, and the case where it is less than 80% is indicated by ×.

  The transparency of the OHP image was evaluated by the following method. The visible spectral transmittance of an image is measured by using a “330 type self-recording spectrophotometer” manufactured by Hitachi, Ltd. with reference to an OHP sheet on which toner is not supported, and the spectral transmittance at 650 nm is obtained to measure the transparency of the OHP image. It was. Spectral transmittance of 80% or more was evaluated as ◯, 70-80% as Δ, and 70% or less as X. The results are shown in Table 4.

  As is apparent from Table 4, since the faithful color reproduction and high OHP quality are exhibited by using the color toner of the present invention, the color toner of the present invention is suitable for use as a full color toner. Furthermore, since the light resistance is good, an image that can be stored for a long time can be provided.

<Preparation of thermal transfer dye donating material>
A 6 μm thick polyethylene terephthalate film (manufactured by Teijin) with a heat-resistant slip treatment on the back side is used as a support, and the coating composition for the thermal transfer dye donating layer having the following composition is dried on the surface of the film by wire bar coating. The thermal transfer dye-donating material (5-1) was prepared by coating so that the thickness at that time was 1.5 μm.
Thermal transfer dye-donating layer coating composition:
Dye 3-7 10 mmol polyvinyl butyral resin (Denkabutyral 5000-A manufactured by Electrochemicals) 3 g
Toluene 40cc
Methyl ethyl ketone 40cc
Polyisocyanate (Takenate D110N, Takeda Pharmaceutical) 0.2cc
Next, a thermal transfer dye-donating material of the present invention and a comparative thermal transfer dye-donating material (5-2) were prepared in the same manner as described above except that the dye 3-7 was changed to the comparative dye described in Table 5.

(Preparation of thermal transfer image-receiving material) A synthetic paper (YUPO-FPG-150 manufactured by Oji Oil Chemical Co., Ltd.) having a thickness of 150 μm is used as a support, and the following composition is applied to the surface so that the thickness when dried is 8 μm by wire bar coating. This was applied to produce a thermal transfer image receiving material. Drying was performed for 30 minutes in an oven at a temperature of 100 ° C. after provisional drying with a dryer.
Image-receiving layer coating composition:
Polyester resin (Toyobo's Byron-280) 22g
Polyisocyanate (Dainippon Ink Chemical KP-90) 4g
Amino-modified silicone oil (Shin-Etsu Silicone KF-857) 0.5g
Methyl ethyl ketone 85cc
Toluene 85cc
Cyclohexanone 15cc

  The thermal transfer dye-donating materials (5-1) and (5-2) obtained as described above and the thermal transfer image-receiving material are superposed so that the thermal transfer dye-donating layer and the image-receiving layer are in contact with each other, and the thermal transfer dye-donating material is obtained. Using a thermal head from the support side, printing is performed under the conditions of thermal head output of 0.25 W / dot, pulse width of 0.15 to 15 milliseconds, dot density of 6 dots / mm, and yellow on the image receiving layer of the image receiving material. Colored dyes were dyed imagewise. Table 4 shows the maximum color density of the obtained image. With the thermal transfer dye donating material (5-1) of the present invention, a clear image recording without transfer unevenness was obtained. Next, each recorded thermal transfer image-receiving material obtained as described above was irradiated with Xe light (17000 lux) for 5 days to examine the light stability of the color image. The status A reflection density after irradiation of the portion showing the status A reflection density 1.0 was measured, and the stability was evaluated by the residual ratio (percentage) with respect to the reflection density 1.0 before irradiation. The results are shown in Table 5.

  As described above, the coloring matter of the present invention was excellent in light fastness as compared with the comparative dye. The hue was also fresh

Regarding the method for producing a color filter, a silicon wafer is spin-coated with a positive resist composition containing a thermosetting resin, a quinonediazide compound, a crosslinking agent, a dye and a solvent, and the solvent is evaporated by heating, and then exposed through a mask. The quinonediazide compound was decomposed. If necessary, a mosaic pattern was obtained by developing after heating. The exposure was performed with an i-line exposure stepper HITACHI LD-5010-i (NA = 0.40) manufactured by Hitachi, Ltd. The developer used was SOPD or SOPD-B manufactured by Sumitomo Chemical Co., Ltd.
<Preparation of positive resist composition>
Cresol novolak resin (polystyrene equivalent weight average molecular weight 4300) 3.4 parts by mass obtained from a mixture of m-cresol / p-cresol / formaldehyde (reaction molar ratio = 5/5 / 7.5), the following formula

O-Naphthoquinonediazide-5-sulfonic acid ester (average of two hydroxyl groups esterified) 1.8 parts by mass, hexamethoxymethylolated melamine 0.8 parts by mass, ethyl lactate 20 A positive resist composition was obtained by mixing 1 part by mass of the dye of the present invention shown in Table 6 with part by mass.
<Preparation of color filter>
The obtained positive resist composition was spin-coated on a silicon wafer, and then the solvent was evaporated. After exposure, the silicon wafer was heated at 100 ° C., and then the exposed portion was removed by alkali development to obtain a positive colored pattern having a resolution of 0.8 μm. This was exposed to light and heated at 150 ° C. for 15 minutes to obtain a yellow complementary color filter.
<Comparative example>
Instead of the yellow dye of the present invention used in the above examples, 1 part by mass of Oreosol Yellow 2G manufactured by Sumitomo Chemical Co., Ltd. was mixed to obtain a positive resist composition. After this positive resist composition was spin coated on a silicon wafer, the solvent was evaporated. After the silicon wafer was exposed, it was alkali-developed to obtain a positive colored pattern having a resolution of 1 μm. After the entire surface was exposed, it was heated at 150 ° C. for 10 minutes to obtain a yellow color filter.
<Evaluation>
The transmission spectrum of the obtained yellow color filter was measured, and the short-wave side and long-wave side cuts of the spectrum important for color reproduction were relatively evaluated. ○ indicates good, Δ indicates an acceptable level, and × indicates an unacceptable level. Further, using a weather meter (Atlas C.I65), xenon light (85000 lx) was irradiated for 7 days, and the image density before and after the xenon irradiation was measured and evaluated as a dye residual ratio.

  Compared with the comparative example, it can be seen that the dye of the present invention has sharp cuts on the short-wave side and long-wave side of the spectrum and is excellent in color reproducibility. It was also found that the light fastness was superior to the comparative compound.

Claims (6)

The pigment | dye represented by the following general formula (A32).

(In the formula, Ar ⁴ represents a benzothiazole ring or thiadiazole ring, Ar ⁵ represents a thiadiazole ring, and R ¹ represents a hydrogen atom , an alkyl group, an aryl group, or an alkoxy group .) An ink containing at least one pigment according to claim 1 . An ink jet recording method for forming an image using the ink according to claim 2 . An ink sheet comprising at least one pigment according to claim 1 . A color toner comprising at least one pigment according to claim 1 . A color filter comprising at least one pigment according to claim 1 .