JP2001334755A - Heat-sensitive transfer recording material, method of heat-sensitive transfer recording, ink for ink-jet recording, color toner, and color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a heat-sensitive transfer recording material for obtaining an image excellent in sensitivity, fixing property, image keeping property and a heat-sensitive transfer recording method using the recording material, also an ink for ink jet recording having proper spectral absorption property and image fastness dependent on respective usage, a color toner, and a color filter. SOLUTION: The heat-sensitive transfer recording material, which contains the pigment shown in the general formula (1), is used. In the formula, R1 and R2 show alkyl radical without a substitution or it is substituted respectively, R3 shows substitution radical, n shows the integer of 0-4. When n is more than 2, more than one R3 may be the same or may be different. R4 shows cycloalkyl radical, the alkyl radical of secondary or tertial, and aryl radical or heterocyclic compound radical, R5 shows hydrogen atom or substitution radical. R6 and R7 show substitution radical respectively. On the other hand, they combine it with each other, and the group of nonmetallic atoms that is necessary to form a ring is shown.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a thermal transfer recording material, a thermal transfer recording method, an ink for inkjet recording,
More specifically, the present invention relates to a thermal transfer recording material, a thermal transfer recording method, an ink jet recording ink, a color toner and a color filter using a specific dye.

[0002]

2. Description of the Related Art Hitherto, as a method for obtaining a color hard copy, color image recording by ink jet, electrophotography, thermal transfer, silver halide photosensitive material, etc. has been studied. Among these, the thermal transfer recording has advantages such as easy operation and maintenance, downsizing of the apparatus and cost reduction, and further low running cost.

In the thermal transfer recording, a dye used in a thermal transfer recording material (hereinafter, also referred to as a thermal transfer material) is important. For the purpose of improving the stability of the obtained image, particularly fixing and light fastness, a heat-sensitive transfer material and an image forming method using a chelatable heat-diffusing dye (hereinafter referred to as a post-chelating dye) have been proposed. For example, Japanese Unexamined Patent Publication No.
No. 78893, No. 59-109349, No. 60-2
398, etc. The image formed using the post-chelating dye disclosed in the above patent is excellent in light fastness and fixability, but is not sufficiently satisfactory in terms of the sensitivity of the thermal transfer material and the storability of the material itself. Also, since the hue difference between the post-chelating dye and the chelating dye is large,
If the chelate reaction at the time of image formation is insufficient, absorption of the chelate dye remains after unreacted or irregular absorption of the formed chelate dye itself. There was a need for further improvements in terms of reproduction.

[0004] In particular, JP-A-3-143684, 3-1
No. 43686, No. 11-78258, Japanese Patent Application No. 11-6
No. 0123 describes a thermal transfer recording material using a dye having a pyrazolopyrimidin-7one nucleus. Although these dyes have improved the above-mentioned problems to some extent, they have not yet reached a satisfactory level, and in particular, have high storage stability under high temperature and high humidity (heat and humidity resistance) and storage stability under light irradiation. (Light resistance) was insufficient, and further improvement was desired.

When the above-mentioned metal chelate dyes are used in ink-jet inks, various recording methods (1:
(A method of ejecting droplets by pressure by electro-mechanical conversion of a piezo element, 2: a method of ejecting droplets by generating bubbles by electro-thermal conversion, 3: a method of sucking and ejecting droplets by electrostatic force, etc.) , High color density and good color tone, excellent image fastness such as light resistance, heat resistance and water resistance, fast fixing to the recording medium, no bleeding after recording, ink It is required to have excellent storage stability, no problem in safety such as toxicity and application, and low cost. From such a viewpoint, various inkjet recording inks have been proposed,
Though studied, ink-jet recording inks that satisfy many of the requirements at the same time are extremely limited.
In color image recording using yellow, magenta, cyan, and black, for example, C.I. I. A conventionally known C.I. described in the index. I. Although dyes and pigments having a number have been widely studied, they have problems in terms of fastness such as light resistance and spectral absorption characteristics relating to color reproducibility such as lack of sharpness of color tone.

Further, consider the case where the above dye is used in a color toner. Color copier using electrophotography,
In a color laser printer, a toner in which a colorant is dispersed in resin particles or a toner in which a colorant is adhered to resin particle surfaces is generally used. In the method of attaching a coloring material to the resin surface, since only the surface is colored, it is difficult to obtain a sufficient coloring effect. In addition, the charging performance changes due to detachment from the surface of the coloring material,
There is another problem that the surface of the fixing roller is contaminated. Therefore, a toner in which a coloring material is dispersed inside particles is widely used. The performance required for such a color toner includes color reproducibility, Over Head Project
or (hereinafter abbreviated as OHP), image transparency and light fastness. JP-A-62-157051 and JP-A-62-25705 disclose a toner in which a pigment is dispersed in particles as a colorant.
No. 5956 and JP-A-6-118715, these toners are excellent in light fastness, but are insoluble and easily aggregated, causing a problem of a decrease in transparency and a change in hue of transmitted color. . On the other hand, a toner using a dye as a coloring material is disclosed in JP-A-3-276161 and JP-A-2-207.
274 and 2-207273,
Conversely, these toners have high transparency and do not change hue, but have a problem in light fastness.

[0007] Further, since a color filter is required to have high transparency, a method called a dyeing method of coloring with a dye has been performed. For example, a photosensitive material to be dyed is applied to a substrate such as glass, followed by pattern exposure of one filter color, and the unexposed portion is washed away in a developing step, and the remaining pattern portion is dyed by the filter color. The color filter can be manufactured by sequentially repeating the operation of dyeing with all the filter colors. This method has a high transmittance due to the use of a dye and has excellent optical characteristics of a color filter, but has a limit in light resistance and heat resistance, and a color material having excellent various resistances and high transparency is desired. I was Therefore, instead of dyes, organic pigments having excellent light resistance and heat resistance have come to be used. However, it has been difficult to obtain optical properties like dyes with a color filter using pigments.

It is desired that the dyes that can be used for the respective applications have the following properties in common. That is, having a favorable hue in terms of color reproducibility, having optimal spectral absorption characteristics, good image fastness such as light resistance, heat resistance, moisture resistance, chemical resistance, and a large molar absorption coefficient. And the like.

[0009]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a thermal transfer recording material for obtaining an image having excellent sensitivity, fixability and image storability, and a thermal transfer recording method using the recording material. It is in. It is another object of the present invention to provide an ink jet recording ink, a color toner, and a color filter having appropriate spectral absorption characteristics and image fastness according to each application.

[0010]

Means for Solving the Problems As a result of earnest studies, the present inventors have found that the object of the present invention can be achieved by using a novel dye having a pyrazolopyrimidin-7-one nucleus. .

That is, the above object of the present invention is achieved by the following constitution. 1. A thermal transfer recording material comprising a dye represented by the formula (I).

2. 2. The thermal transfer recording material according to 1, wherein both R ⁶ and R ⁷ in the general formula (I) are alkyl groups.

3. R ⁴ in the general formula (I) is i-
3. The heat-sensitive transfer recording material according to 1 or 2, which is a propyl group or a tert-butyl group.

4. Superimposing an image-receiving material on a dye-donor material having a dye-donor layer containing the dye represented by formula (I) on a support, and heating the dye-donor material according to image information to form an image; A thermal transfer recording method comprising:

[0015] 5. A dye-donor material having a dye-donor layer containing the dye represented by the general formula (I) on a support,
An image receiving material having a dye image receiving layer containing a metal ion-containing compound is superimposed on a support, and the dye donor material is heated according to image information, and a metal chelate dye image is formed by the reaction between the dye and the metal ion-containing compound. A thermal transfer recording method characterized by forming.

6. An ink jet recording ink comprising a metal chelate dye formed by a reaction between the dye represented by the general formula (I) and a metal ion-containing compound.

[7] A color toner comprising a metal chelate dye formed by a reaction between the dye represented by the general formula (I) and a metal ion-containing compound.

[8] A color filter comprising a metal chelate dye formed by a reaction between the dye represented by the general formula (I) and a metal ion-containing compound.

Hereinafter, the present invention will be described in detail. The novel dye represented by formula (I) will be described.

In the general formula (I), R ¹ and R ²
Represent each a substituted or unsubstituted alkyl group, R ¹
And R ² may be the same or different. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and an i-propyl group. As a group capable of substituting these alkyl groups (that is, a substituent to the alkyl group represented by R ¹ and R ² ), a linear or branched alkyl group (for example, a methyl group, an ethyl group, an i-propyl group) ,
t-butyl group, dodecyl group, 1-hexylnonyl group, etc.), cycloalkyl group (for example, cyclopropyl group,
Cyclohexyl group, bicyclo [2.2.1] heptyl group, adamantyl group, etc.), alkenyl group (eg, 2-propylene group, oleyl group, etc.), aryl group (eg, phenyl group, ortho-tolyl group, ortho-anisyl) Group, 1-naphthyl group, 9-anthranyl group, etc.),
A heterocyclic group (eg, a 2-tetrahydrofuryl group, a 2-thiophenyl group, a 4-imidazolyl group, a 2-pyridyl group, etc.), a halogen atom (eg, a fluorine atom, a chlorine atom,
Bromine atom, etc., cyano group, nitro group, hydroxy group, carbonyl group (for example, alkylcarbonyl group such as acetyl group, trifluoroacetyl group, pivaloyl group, benzoyl group, pentafluorobenzoyl group, 3,5-di-t-
An arylcarbonyl group such as a butyl-4-hydroxybenzoyl group, an oxycarbonyl group (e.g., an alkoxycarbonyl group such as a methoxycarbonyl group, a cyclohexyloxycarbonyl group, a dodecyloxycarbonyl group,
An aryloxycarbonyl group such as a phenoxycarbonyl group, a 2,4-di-t-amylphenoxycarbonyl group, a 1-naphthyloxycarbonyl group, and a 2-pyridyloxycarbonyl group and a 1-phenylpyrazolyl-5-oxycarbonyl group; An alkylcarbamoyl group such as a heterocyclic oxycarbonyl group, a carbamoyl group (for example, dimethylcarbamoyl group, 4- (2,4-di-t-amylphenoxy) butylaminocarbonyl group), a phenylcarbamoyl group, a 1-naphthylcarbamoyl group, and the like; Arylcarbamoyl group, etc.), alkoxy group (for example, methoxy group, 2-ethoxyethoxy group, etc.), aryloxy group (for example, phenoxy group, 2,4-di-t-amylphenoxy group, 4- (4-hydroxyphenylsulfonyl) ) Phenoxy group, etc.) Ring oxy group (e.g., 4-pyridyloxy group, 2-hexa tetrahydropyranyl group, etc.), carbonyl group (e.g. acetyl group,
Trifluoroacetyloxy group, alkylcarbonyloxy group such as pivaloyloxy group, benzoyloxy group,
An aryloxy group such as a pentafluorobenzoyloxy group, a urethane group (eg, an alkyl urethane group such as an N, N-dimethyl urethane group, an N-phenyl urethane group,
Aryl urethane groups such as N- (p-cyanophenyl) urethane group, etc.), sulfonyloxy groups (eg, alkylsulfonyloxy groups such as methanesulfonyloxy group, trifluoromethanesulfonyloxy group, dodecanesulfonyloxy group, etc.), benzenesulfonyloxy group, arylsulfonyloxy group such as p-toluenesulfonyloxy group and the like; amino groups (eg alkylamino group such as dimethylamino group, cyclohexylamino group and dodecylamino group), anilino group and aryl such as pt-octylanilino group An amino group, a sulfonylamino group (eg, a methanesulfonylamino group, an heptafluoropropanesulfonylamino group, an alkylsulfonylamino group such as a hexadecylsulfonylamino group, a p-toluenesulfonylamino group, a pentafluoro group) Arylsulfonylamino group such as benzenesulfonylamino, etc.), sulfamoylamino group (eg, alkylsulfamoylamino group such as N, N-dimethylsulfamoylamino group, and arylsulfone such as N-phenylsulfamoylamino group). An alkylcarbonylamino group such as a famoylamino group), an acylamino group (eg, an acetylamino group, a myristoylamino group),
An arylureido group such as an arylcarbonylamino group such as a benzoylamino group, an alkylureido group such as an N, N-dimethylaminoureido group, an N-phenylureido group, and an N- (p-cyanophenyl) ureide group; Group), a sulfonyl group (eg, an alkylsulfonyl group such as a methanesulfonyl group and a trifluoromethanesulfonyl group, and an arylsulfonyl group such as a p-toluenesulfonyl group), a sulfamoyl group (eg, a dimethylsulfamoyl group, 4- (2 , 4-di-t-amylphenoxy) alkylsulfamoyl group such as butylaminosulfonyl group, arylsulfamoyl group such as phenylsulfamoyl group, and alkylthio group (eg, methylthio group, t-octylthio group, etc.) An arylthio group (eg, phenylthio) Group), and heterocyclic thio group (e.g., 1-phenyl-tetrazolyl-5-thio, 5-methyl-1,3,4-oxadiazolyl-2-thio group).

As the substituent for the alkyl group represented by R ¹ and R ² , an alkyl group and a cycloalkyl group are preferable among the above substituents. It is also preferred that R ¹ and R ^{2 form} a non-aromatic cyclic structure (for example, a pyrrolidine ring, a piperidine ring, a morpholine ring, etc.).

The substituent represented by R ³ includes R ¹ and R ²
And a group having the same meaning as the substituent for the alkyl group represented by formula (1), among which an alkyl group, a cycloalkyl group, an alkoxy group, and an acylamino group are preferable. n represents an integer of 0 to 4, and when n is 2 or more, a plurality of R ³ may be the same or different.

R ⁴ represents a cycloalkyl group, a secondary or tertiary alkyl group, an aryl group or a heterocyclic group. Examples of the cycloalkyl group include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group and a cycloheptyl group. And the secondary or tertiary alkyl group includes, for example, isopropyl group, sec-butyl group, te
rt-butyl group, 3-heptyl group and the like. Examples of the aryl group include a phenyl group and a naphthyl group, and examples of the heterocyclic group include a pyridyl group, a pyrazolyl group, a thienyl group, a thiazolyl group, a triazolyl group,
Examples include a pyrazyl group, a pyrrolidinyl group, a piperidyl group, a sulfolanyl group, a 1,3-dioxanyl group, and a morpholyl group. R ⁴ is preferably a phenyl group or a pyrazolyl group. The group represented by R ⁴ may be unsubstituted or substituted. Examples of the group capable of substituting R ⁴ include the same groups as those described above as the groups capable of substituting R ¹ and R ^2. Is mentioned. Particularly preferred substituents for R ⁴ are cyclohexyl, isopropyl, tert-butyl, p-tolyl, o-tolyl, o-chlorophenyl, o-anisyl, p-anisyl, mesityl, thienyl. , A piperidyl group, and most preferably an isopropyl group, a tert-butyl group and an o-chlorophenyl group.

R ⁵ represents a hydrogen atom or a substituent. Specific examples of the substituent include the substituents described above as the groups capable of substituting R ¹ and R ² , and preferably a hydrogen atom, Alkyl group (eg, methyl group, ethyl group, i-propyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, cyclooctyl group, etc.), aryl group (eg, phenyl group, o-tolyl group, mesityl group, -Naphthyl group etc.). When the compound of the general formula (I) is used for the thermal transfer recording material, R ⁵ is particularly preferably a hydrogen atom, a methyl group or an ethyl group.

Examples of the substituents represented by R ⁶ and R ⁷ include the substituents described above as the groups capable of substituting R ¹ and R ² , and among the substituents, an alkyl group and a cyclo group are preferred. It is preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, or an amino group. In addition, R ⁶
And R ⁷ may combine with each other to form a ring, and the ring formed in such a case includes a benzene ring, a naphthalene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a thiophene ring, a thiazole ring, and a furan ring. Non-aromatic rings such as an aromatic ring, a cyclopentene ring, a cyclohexene ring and a cycloheptene ring can be exemplified, and these may be further substituted by the substituents mentioned above as the groups capable of substituting R ¹ and R ^2. .

The following are specific examples of the dye represented by formula (I) of the present invention, but the present invention is not limited thereto.

[0027]

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[0028]

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[0029]

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[0030]

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[0031]

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[0032]

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[0033]

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The dye represented by formula (I) of the present invention can be synthesized by the method described in Japanese Patent Application No. 11-60123. For example, in the case of Exemplified Compound 7, it can be synthesized according to the following scheme.

(Synthesis of Exemplified Compound 7)

[0036]

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5.2 g of aminopyrazole (1) and 10.9 g of ketoester (2) were dissolved in 30 ml of xylene and heated for 2.5 hours while distilling off the solvent. It is thought that the obtained oily product mainly contained the dye precursor (3), and this was used in the next step without purification. 100 m of ethyl acetate was added to the oily product containing (3).
and a solution prepared by dissolving 7.2 g of the aniline derivative (4) in 100 ml of water and 15 g of sodium persulfate in 150 ml of water. The solution was added alternately in small portions. After vigorous stirring at room temperature for 2 hours, ethyl acetate and dilute hydrochloric acid were added to separate the organic layer. The organic layer was washed with dilute hydrochloric acid, water and saturated saline, concentrated, and then subjected to silica gel column chromatography (developing solvent was , Ethyl acetate / n-hexane = 1: 3)
And purified by recrystallization from ethyl acetate.
4.9 g of a green crystal having a metallic luster (total yield of two steps: 27%) was obtained. The structure was confirmed by NMR spectrum and mass spectrum. Further, λmax in the acetone solution of Exemplified Compound 7 was 584 nm.

The other exemplified compounds can be synthesized in the same manner. The thermal transfer recording material of the present invention has a thermal transfer layer having the dye of the present invention on a support. The heat-sensitive transfer layer is prepared by dissolving a dye together with a binder in a solvent, or by dispersing the dye in a fine particle form in a solvent to prepare an ink liquid for forming a heat-sensitive transfer layer, applying the ink on a support, and drying it appropriately. Can be formed. The thickness of the heat-sensitive transfer layer is 0.1 to 10 μm in dry film thickness.
Is preferred.

The binder is preferably a solvent-soluble polymer such as acrylic resin, methacrylic resin, polystyrene, polycarbonate, polysulfone, polyethersulfone, polyvinyl butyral, polyvinyl butyral, polyvinyl acetal, nitrocellulose and ethyl cellulose. These binders may be used not only by dissolving one kind or two or more kinds in an organic solvent, but also in the form of a latex dispersion. The amount of the binder used is preferably 0.1 to ²⁰ g per 1 m ² of the support.

As the organic solvent, alcohols (ethanol, propanol, etc.), cellosolves (methyl cellosolve, ethyl cellosolve, etc.), aromatics (toluene, xylene, etc.), esters (ethyl acetate, etc.), ketones (acetone, etc.) , Methyl ethyl ketone, etc.), ethers (tetrahydrofuran, dioxane, etc.) and the like.

The support may be any as long as it has good dimensional stability and withstands heating of a thermal head or the like during recording.
Thin paper such as condenser paper and glassine paper, and heat-resistant plastic films such as polyethylene terephthalate, polyamide and polycarbonate are preferably used. The thickness of the support is preferably 2 to 30 μm.

The support preferably has an undercoat layer made of a polymer selected for the purpose of improving the adhesion to the binder and preventing the transfer and dyeing of the dye to the support. Further, on the back surface of the support (the side opposite to the thermal transfer layer),
It may have a slipping layer for the purpose of preventing the head from sticking to the support.

The heat-sensitive transfer recording material of the present invention may be used as an image-receiving material described later, which is not provided with an image-receiving layer, such as plain paper, as described in JP-A-59-259, as a heat-sensitive transfer layer or as a separate layer.
You may have the heat-fusible layer containing a heat-fusible compound as described in -106997. As the heat-fusible compound, a colorless or white compound that melts at a temperature of 65 to 150 ° C. is preferable. For example, carnauba wax,
Waxes such as beeswax and candeline wax are used.

The heat-fusible layer may contain a polymer such as polyvinylpyrrolidone, polyvinylbutyral, polyester, and vinyl acetate.

To apply the heat-sensitive transfer recording material of the present invention to full-color image recording, a yellow heat-sensitive transfer layer containing a heat-diffusible yellow dye capable of forming a yellow image and a heat-diffusible magenta dye capable of forming a magenta image are contained. It is preferred that a total of three layers, a magenta thermal transfer layer and a cyan thermal transfer layer containing a heat-diffusable cyan dye capable of forming a cyan image, are sequentially and repeatedly coated on the same surface on the support. If necessary, a total of four heat-sensitive transfer layers containing a black image-forming substance may be successively and repeatedly applied on the same surface.

In the thermal transfer recording method of the present invention, an image receiving material is superimposed on a dye donating material having a dye donating layer containing at least one kind of the dye represented by formula (I) on a support. The dye-providing material is heated according to the image information, and the dye is transferred to form an image.

Further, it is preferable to use the dye of the present invention in combination with a metal ion-containing compound. That is, an image receiving material having a dye-donating material having a dye-donating layer containing at least one of the dyes represented by the formula (I) on a support and a dye-image receiving layer containing a metal ion-containing compound on a support. The materials are stacked, and the dye-providing material is heated according to the image information, and a metal chelate dye image is formed by the reaction between the dye and the metal ion-containing compound. The metal ion-containing compound may be present in the image receiving material or may be present in the heat-meltable layer of the dye-providing material.

Examples of the metal ion-containing compound include inorganic or organic salts and metal complexes of metal ions, and among them, organic acid salts and complexes are preferable.

Examples of the metal include monovalent and polyvalent metals belonging to Groups V to VIII of the periodic table.
1, Co, Cr, Cu, Fe, Mg, Mn, Mo, N
i, Sn, Ti and Zn are preferred, and especially Ni, Cu,
Cr, Co and Zn are preferred.

Specific examples of the metal ion-containing compound include:
Salts of Ni ²⁺ , Cu ²⁺ , Cr ²⁺ , Co ²⁺ and Zn ²⁺ with aliphatic acids such as acetic acid and stearic acid, or salts with aromatic carboxylic acids such as benzoic acid and salicylic acid. No.
Further, a complex represented by the following general formula (II) can be particularly preferably used.

[0051] Formula _{(II) [M (Q 1} ) a (Q 2) b (Q 3) c] p + (Y -) in _{the p-type,} M is a metal ion, preferably Ni ^2+, Cu ^2+, C
r ²⁺ , Co ²⁺ , and Zn ²⁺ .

Q ₁ , Q ₂ and Q ₃ each represent a coordination compound capable of coordinating with the metal ion represented by M, and may be the same or different. These coordination compounds can be selected, for example, from the coordination compounds described in Chelate Science (5) (Nankodo).

[0053] Y ^- is represents an organic anion group, and specific examples thereof include tetraphenyl boron anion and alkylbenzene sulfonate anion.

A represents 1, 2 or 3, b represents 1, 2 or 0, and c represents 1 or 0, which are represented by the general formula (I
It is determined by whether the complex represented by I) is tetradentate or hexadentate, or is determined by the number of ligands of Q ₁ , Q ₂ and Q ₃ .

P represents 0, 1 or 2. p = 0 is
Q _1, coordination compounds represented by Q _2, Q ₃ is an anionic compound, Q _1, Q _2, and a metal cation represented by anionic compounds represented by Q ₃ and M are electrically It means that it is in a neutralized state.

As the anionic compound, the following general formula (II)
Compounds represented by I) are preferred. General formula (III) O ^-- C (R ⁵ ) = C (R ⁷ ) -C (= O) (R ⁶ ) wherein R ⁵ and R ⁶ may be the same or different alkyl R ⁷ represents an alkyl group, an alkoxy group, an alkoxycarbonyl group, a halogen atom or a hydrogen atom.

The amount of the metal ion-containing compound to be added is usually
Preferably 0.5 to 20 g / m ² to an image-receiving material or the thermally fusible layer, 1 to 15 g / m ² is more preferable.

The image-receiving material for forming an image with the metal complex dye is generally made of paper, a plastic film, or a paper-plastic film composite as a support, and a polyester resin, polyvinyl chloride resin, vinyl chloride as an image receiving layer thereon. And a polymer layer made of one or more of a copolymer resin of styrene and another monomer (such as vinyl acetate), polyvinyl butyral, polyvinyl pyrrolidone, polycarbonate and the like.

The image receiving material may contain an antioxidant, a release agent, and the like in the image receiving layer, if necessary, and a protective layer may be provided on the image receiving layer. An intermediate layer may be provided between the image receiving layers for the purpose of adhesion, heat insulation, or a cushion effect. Further, on the back surface of the support (on the side opposite to the image receiving layer), an antistatic layer and a back layer containing inorganic or organic non-sublimable fine particles for the purpose of preventing blocking may be provided.
Further, an image receiving layer may be provided on both surfaces of the support. The support itself may be used as the image receiving material.

Heating by a thermal head is generally used in the thermal transfer recording method, but heating by electric current or heating using a laser may be used. The application of heat by a thermal head or the like may be performed from the back side of the dye-providing material or the thermal transfer material, or may be performed without particular limitation on the back side of the image-receiving material, provided that the transfer speed of the dye and the image density are taken into consideration. , From the back side of the dye-providing material. Also, before, during or after the transfer of the dye, further heating to promote dye transfer,
It is possible to promote the reaction with the metal ion-containing compound and the fixing of the transfer dye.

Next, an example of the thermal transfer recording method of the present invention will be described with reference to FIGS. In the thermal transfer recording material of FIG. 1, the image receiving material 3 has a structure in which an image receiving layer 2 containing a metal ion-containing compound is provided on a support 1, and a dye donating material 6 is provided on a support 4 according to the present invention. This is a configuration in which a dye-donating layer 5 containing such a dye is provided. The image receiving material 3 and the dye-providing material 6 may each have an intermediate layer between the support and the support.

As a thermal transfer recording method, the image receiving material 3 and the dye-providing material 6 are overlapped, and heat is applied from the back side of the dye-providing material 6 to the heating resistor 8 carried on the thermal head 7 in accordance with image information. Then, both materials are peeled off. At this time, a metal complex dye image is formed by a reaction between the dye in the dye donating layer 5 and the metal ion-containing compound in the image receiving layer 2.

In the thermal transfer recording material of FIG. 2, the dye-providing material 6 (4 + 5) of the thermal transfer recording material of FIG.
A heat-sensitive transfer recording material 10 comprising a heat-meltable layer 9 containing a metal ion-containing compound laminated thereon and an image-receiving material 3 having no image-receiving layer, such as the above-mentioned plain paper, are superposed on each other, and the heat-sensitive transfer shown in FIG. The thermal head 7 is used in the same manner as in the recording method, and thereafter, the two materials are peeled off to form an image. In the case of this method, when heat is applied by the thermal head 7, the metal complex dye image is formed between the dye-donating layer 5 and the heat-fusible layer 9 on the thermal transfer recording material 10 by the reaction between the dye and the metal ion-containing compound. Is generated, and then the image is received on the image receiving material 3.

The ink-jet recording ink containing a dye represented by the general formula (I) of the present invention (hereinafter also referred to as an ink-jet recording liquid) is a water-based ink-jet recording liquid.
The present invention can be applied to various inkjet recording liquids such as an oil-based inkjet recording liquid and a solid (phase change) inkjet recording liquid.

The aqueous ink jet recording liquid generally uses water and a water-soluble organic solvent as solvents in addition to the compound of the present invention. Examples of the water-soluble organic solvent include alcohols (eg, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, secondary butanol, tertiary butanol, pentanol, hexanol, cyclohexanol, benzyl alcohol, etc.), and polyhydric alcohols (Eg, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol,
Dipropylene glycol, polypropylene glycol,
Butylene glycol, hexanediol, pentanediol, glycerin, hexanetriol, thiodiglycol, etc.), ethers of polyhydric alcohols (for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether,
Diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, triethylene glycol monomethyl ether,
Triethylene glycol monoethyl ether, ethylene glycol monophenyl ether, propylene glycol monophenyl ether, etc.), amines (for example, ethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, morpholine, N-ethyl) Morpholine,
Ethylenediamine, diethylenediamine, triethylenetetramine, tetraethylenepentamine, polyethyleneimine, pentamethyldiethylenetriamine, tetramethylpropylenediamine, etc., amides (eg, formamide, N, N-dimethylformamide, N, N-dimethylacetamide) And heterocycles (for example, 2-pyrrolidone, N-methyl-2-pyrrolidone, cyclohexylpyrrolidone, 2-oxazolidone, 1,3-dimethyl-
2-imidazolidinone, etc.), sulfoxides (for example,
Dimethyl sulfoxide), sulfones (eg, sulfolane), urea, acetonitrile, acetone, and the like.

In the aqueous ink jet recording liquid as described above, the dye can be used as it is if it is soluble in the solvent system. On the other hand, when the compound is an insoluble solid as it is, the compound of the present invention is dispersed in various dispersers (for example, ball mill, sand mill, attritor, roll mill, agitator mill, Henschel mixer, colloid mill, ultrasonic homogenizer, pearl mill, jet mill, (Eg, ongmill), or after dissolving the dye in a soluble organic solvent, and dispersing it in a solvent system for the aqueous inkjet recording liquid together with a polymer dispersant and a surfactant. Further, when the liquid or semi-molten substance is insoluble as it is, it is dissolved as it is or in a soluble organic solvent, and dispersed in a solvent system for the aqueous inkjet recording liquid together with a polymer dispersant and a surfactant. Can be done. For a specific method for preparing such an aqueous ink jet recording liquid, see, for example, JP-A-5-148436 and JP-A-5-295512.
Nos. 7-97541, 7-82515, 7-
118584 and the like.

The oil-based ink jet recording liquid uses an organic solvent as a solvent in addition to the dye of the present invention. Examples of the solvent of the oil-based inkjet recording liquid include alcohols (for example, pentanol, heptanol, octanol, phenylethyl alcohol, and the like) in addition to those exemplified as the water-soluble organic solvent in the aqueous inkjet recording liquid.
Phenylpropyl alcohol, furfuryl alcohol,
Anil alcohol, etc.), esters (ethylene glycol diacetate, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, propylene glycol diacetate, ethyl acetate, amyl acetate, benzyl acetate, phenylethyl acetate, phenoxyethyl acetate, phenylethyl acetate, Benzyl propionate, ethyl benzoate, butyl benzoate, butyl laurate, isopropyl myristate, triethyl phosphate, tributyl phosphate, diethyl phthalate, dibutyl phthalate, diethyl malonate, dipropyl malonate, diethyl malonate, succinate Diethyl acetate, dibutyl succinate, diethyl glutarate, diethyl adipate, dipropyl adipate, dibutyl adipate, dibutyl adipate (2 Methoxyethyl), diethyl sebacate, diethyl maleate, dibutyl maleate,
Dioctyl maleate, diethyl fumarate, dioctyl fumarate, -3-hexenyl cinnamate, etc., ethers (eg, butyl phenyl ether, benzyl ethyl ether, hexyl ether, etc.), ketones (eg, benzyl methyl ketone, benzyl) Acetone, diacetone alcohol, cyclohexanone, etc.), hydrocarbons (eg, petroleum ether, petroleum benzyl, tetralin, decalin, tertiary amylbenzene, dimethylnaphthalene, etc.), amides (eg, N, N-diethyldodecaneamide) And the like.

In the oil-based ink jet recording liquid as described above, the dye can be used by dissolving it as it is.
In addition, a resinous dispersant or a binder may be used in combination for dispersion or dissolution.

For a specific method for preparing such an oil-based ink jet recording liquid, the methods described in JP-A-3-231975, JP-T-5-508883 and the like can be referred to.

The solid (phase change) ink jet recording liquid is
In addition to the compound of the present invention, a phase change solvent that is solid at room temperature and is in a molten liquid state when the ink is heated and jetted is used as a solvent. Examples of such phase change solvents include natural waxes (for example, beeswax, carnauba wax, rice wax, wood wax, jojoba oil, whale wax, candelilla wax, lanolin, montan wax, ozokerite,
Ceresin, paraffin wax, microcrystalline wax, petrolactam, etc.), polyethylene wax derivative, chlorinated hydrocarbon, organic acid (for example, palmitic acid, stearic acid, behenic acid, tiglic acid, 2-acetonaphthone behenic acid, 12-) Hydroxystearic acid, dihydroxystearic acid, etc.), organic acid esters (eg, esters of the above-mentioned organic acids with alcohols such as glycerin, diethylene glycol, ethylene glycol, etc.), and alcohols (eg, dodecanol, tetradecanol, hexadecanol). Eicosanol, docosanol, tetracosanol, hexacosanol, octacosanol, dodecenol, myricyl alcohol, tetracenol, hexadecenol, eicosenol, docosenol, pineneglyco Le, hinokiol, butynediol, nonanediol, iso phthalyl alcohols, Meshiserin, tele-after Lil alcohol, hexanediol, decanediol, dodecanediol, tetradecane diol, hexadecane diol, DoCoMo Sanji ol,
Tetracosanediol, tvneol, phenylglycerin, eicosanediol, octanediol, phenylpropylene glycol, bisphenol A, para-alpha cumylphenol, etc., ketones (for example, benzoylacetone, diacetbenzene, benzophenone, tricosanone, heptacosanone, Heptria Contanone, Hentria Contanone, Heptria Contanone,
Stearone, lauron, etc.), amides (e.g., oleamide, laurylamide, stearamide, ricinoleamide, palmitamide, tetrahydrofuranamide, erucamide, myristic amide, 12-hydroxystearic amide, N -Stearyl erucamide, N-oleyl stearamide, N, N'-ethylenebislauric amide, N,
N'-ethylenebisstearic acid amide, N, N'-ethylenebisoleic acid amide, N, N'-methylenebisstearic acid amide, N, N'-ethylenebisbehenic acid amide, N, N'-xylylenebis Stearamide, N, N'-butylenebisstearic amide,
N'-dioleyl adipamide, N, N'-distearyl adipamide, N, N'-dioleyl sebacamide, N, N'-cystearyl sebacamide, N, N'-distearyl terephthalate Acid amide, N,
N'-distearyl isophthalic amide, phenacetin, toluamide, acetamide, oleic acid dimer / ethylenediamine / stearic acid (1: 2: 2 molar ratio)
Reaction products of dimer acids, diamines and fatty acids such as tetraamides), sulfonamides (eg, paratoluenesulfonamide, ethylbenzenesulfonamide, butylbenzenesulfonamide, etc.), and silicones (eg, silicone SH6018 (Toray Silicone) ), Silicone KR215, 216, 220 (Shin-Etsu Silicone)
), Coumarones (for example, Escron G-90 (Nippon Steel Chemical), etc.), cholesterol fatty acid esters (for example, cholesterol stearate, cholesterol palmitate, cholesterol myristate, cholesterol behenate, cholesterol laurate, cholesterol melissinate) Saccharose stearate, saccharose palmitate, saccharose behenate, saccharose laurate, saccharose melissinate, lactose stearate, lactose palmitate, lactose myristate, lactose behenate, lactose laurate, lactose melinate. etc)
And the like.

Solid ink jet recording liquid (solid ink)
Is preferably 60 ° C. or more, more preferably 80 to 150 ° C. in the solid-liquid phase change.

In the solid ink-jet recording liquid as described above, the dye of the present invention can be used by dissolving the dye of the present invention as it is in a solvent in a heated and molten state, or dispersed or dissolved in combination with a resinous dispersant or a binder. Can also be used.

For a specific method for preparing such a solid ink jet recording liquid, the methods described in JP-A-5-186723 and JP-A-7-70490 can be referred to.

The water-based, oil-based, and solid ink-jet recording liquids described above have a viscosity of 40 cp during flight.
s or less, and more preferably 30 cps or less.

The ink jet recording liquid of the present invention
2.0 × 10 as the surface tension during the sho ^-2Nm^-1More preferred
3.0-8.0 × 10^-2Nm^-1Is that
Is more preferable.

The dye of the present invention is used preferably in the range of 0.1 to 25% by mass, more preferably in the range of 0.5 to 10% by mass, based on the total amount of the ink jet recording liquid.

In the ink jet recording liquid of the present invention, a viscosity adjusting agent, a surface tension adjusting agent and the like can be used in accordance with the purpose of improving ejection stability, compatibility with a print head or ink cartridge, storage stability, image storability and other various properties. Formulations, resistivity adjusters, film-forming agents, dispersants, surfactants, ultraviolet absorbers, antioxidants, anti-fading agents, fungicides, rust inhibitors and the like can also be added.

The ink jet recording liquid of the present invention is not particularly limited with respect to the recording method used, but can be preferably used as an ink for an on-demand type ink jet printer. On-demand type systems include electro-mechanical conversion systems (eg, single cavity type, double cavity type, bender type, piston type, shared mode type, shared wall type, etc.),
Specific examples include an electric-heat conversion method (for example, a thermal ink jet type, a bubble jet type, etc.), an electrostatic suction method (for example, an electric field control type, a slit jet type, etc.), a discharge method (for example, a spark jet type, etc.). Examples can be given.

When the compound of the present invention is used as a colorant for a color toner, any binder generally used can be used as a binder resin for preparing the toner. For example, a styrene resin, an acrylic resin, a styrene / acrylic resin, a polyester resin, and the like can be given.

In the present invention, an inorganic fine powder or an organic fine particle may be externally added to the toner for the purpose of improving the fluidity and controlling the charge. Silica fine particles and titania fine particles whose surfaces are treated with an alkyl group-containing coupling agent or the like are preferably used. These preferably have a number average primary particle diameter of 10 to 500 nm, and more preferably 0.1 to 20% by mass of the toner.

As the release agent, any of the conventionally used release agents can be used. Specific examples include low molecular weight polypropylene, low molecular weight polyethylene, olefins such as ethylene-propylene copolymer, microcrystalline wax, carnauba wax, sasol wax, paraffin wax and the like. It is preferable that these additives are added in the toner in an amount of 1 to 5% by mass.

The charge control agent may be added as required, 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, any of an uncoated carrier composed of only magnetic material particles such as iron and ferrite, and a resin-coated carrier having magnetic material particle surfaces coated with resin or the like may be used. The average particle size of the carrier is preferably 30 to 150 μm in 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 an image by repeatedly forming a color image on a photoreceptor and then transferring the same, The image formed on the intermediate transfer member or the like is sequentially transferred to the intermediate transfer member or the like, a color image is formed on the intermediate transfer member or the like, and then transferred to an image forming member such as paper to form a color image.

In dispersing the compound of the present invention into a transparent resin when the compound of the present invention is used for a color filter, various dispersing means such as a two-roll mill, a three-roll mill, a sand mill and a kneader can be used.

In the present invention, as a resin varnish for dispersing a compound to form a coloring composition, a varnish used in a conventionally known coloring composition for a color filter is used. As the dispersion medium, a solvent or an aqueous medium suitable for the resin varnish is used. If necessary, conventionally known additives such as a dispersing aid, a leveling agent, and a cohesive agent are added and used.

As the resin varnish, a photosensitive resin varnish and a non-photosensitive resin varnish are used. As the photosensitive resin varnish, for example, a UV curable ink, a photosensitive resin varnish used for electron beam curable ink and the like, as a non-photosensitive resin varnish, for example, letterpress ink, planographic ink, intaglio gravure ink, Any of varnish used for printing ink such as stencil screen ink, varnish used for electrodeposition coating, varnish used for developer of electronic printing and electrostatic printing, varnish used for thermal transfer ribbon and the like can be used.

Examples of the photosensitive resin varnish include photosensitive cyclized rubber resins, photosensitive phenol resins, photosensitive polymethacrylate resins, photosensitive polyamide resins, photosensitive polyimide resins, and unsaturated polyester resins. Resin,
Varnishes such as polyester acrylate-based resins, polyepoxy acrylate-based resins, polyurethane acrylate-based resins, polyether acrylate-based resins, and polyol acrylate-based resins, and further include varnishes to which a monomer is added as a reactive diluent. The photosensitive coloring composition of the present invention can be obtained by adding a photopolymerization initiator such as benzoin ether and benzophenone to the compound of the present invention and the above-mentioned varnish, followed by briquetting by a conventionally known method. Further, a thermopolymerizable colored composition can be obtained by using a thermopolymerization initiator instead of the above photopolymerization initiator.
When a color filter pattern is formed using the above-described photosensitive coloring composition, the photosensitive coloring composition is spin-coated on a transparent substrate, and is entirely coated using a low-speed rotation coater, a roll coater, a knife coater, or the like. Alternatively, full-scale printing or partial printing slightly larger than the pattern is performed by various printing methods, and after predrying, a photomask is brought into close contact, and exposure is performed using an ultra-high pressure mercury lamp to print the pattern. Next, development and washing are performed, and post-baking is performed as needed, whereby a color filter pattern can be formed.

Examples of the non-photosensitive resin varnish include cellulose acetate resins, nitrocellulose resins,
Styrene (co) polymer, polyvinyl butyral resin, amino alkyd resin, polyester resin, amino resin modified polyester resin, polyurethane resin, acrylic polyol urethane resin, soluble polyamide resin, soluble polyimide resin, Soluble polyamideimide resin, soluble polyesterimide resin, casein, hydroxyethylcellulose, water-soluble salt of styrene-maleic ester copolymer, water-soluble salt of (meth) acrylic ester (co) polymer, water-soluble Amino alkyd resin, water-soluble amino polyester resin,
Water-soluble polyamide resins and the like can be mentioned, and they are used alone or in combination.

When a color filter pattern is formed by using the above-mentioned non-photosensitive coloring composition, the above-mentioned various types of the above-mentioned non-photosensitive coloring composition, for example, a printing ink for a color filter are formed on a transparent substrate. A method of printing a colored pattern directly on a substrate by a printing method, a method of forming a colored pattern on a substrate by electrodeposition coating using an aqueous electrodeposition coating composition for a color filter, an electronic printing method or an electrostatic printing method, Alternatively, a method in which a colored pattern is once formed on a transferable base material by the above method or the like and then transferred to a substrate for a color filter may be used. Next, baking is performed as necessary, polishing is performed for smoothing the surface, and top coating is performed for protecting the surface according to a conventional method. Also, a black matrix is formed according to a standard method,
Obtain RGB color filters.

[0091]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the present invention is limited thereto.

Example 1 (Preparation of ink) The following raw materials were mixed to obtain an ink of a uniform solution containing the dye represented by the general formula (I) of the present invention. The solubility of the dye was good, and the suitability for ink formation was also good.

Exemplary compound 1 of the dye represented by formula (I) of the present invention 1 0.72 g polyvinyl acetoacetal resin (KY-24: manufactured by Denki Kagaku Kogyo) 1.08 g methyl ethyl ketone 26.4 ml toluene 1.6 ml (sensitivity) Preparation of thermal transfer recording material) The above ink was applied to a thickness of 4.5.
μg of polyethylene terephthalate (PET) base with 2.3 g / m
^The resultant was coated and dried to obtain a thermal transfer recording material 1 having a thermal transfer layer provided on a PET film.
Note that a nitrocellulose layer containing a silicon-modified urethane resin (SP-2105: manufactured by Dainichi Seika) is provided on the back surface of the PET base as a sticking preventing layer.

The heat-sensitive transfer recording materials 2 to 1 were prepared in the same manner except that the dyes of the heat-sensitive transfer recording material 1 were changed to the dyes shown in Table 1.
2 was produced.

(Preparation of Image Receiving Material) A coating solution having the following composition was dried on a support (a polyethylene layer on one side containing a white pigment (titanium dioxide) and a bluing agent) on which polyethylene was laminated on both sides of paper. Was applied and dried so that the coating amount was 7.2 g, whereby an image receiving material 1 was produced.

Metal ion-containing compound (MS-1) 4.0 g Polyvinyl butyral resin (BX-1: manufactured by Sekisui Chemical Co., Ltd.) 6.0 g Polyester modified silicone 0.3 g

[0097]

Embedded image

Further, an image receiving material 2 containing no metal ion-containing compound was prepared in the same manner as in the above image receiving material 1 except that MS-1 was omitted.

(Thermal Transfer Recording) The thermal transfer recording material and the image receiving material are superimposed, and an image is recorded by a thermal printer with a thermal head applied from the back of the thermal transfer recording material. 24 was obtained.

The maximum density of the obtained image, the sensitivity of the heat-sensitive transfer recording material, and the light resistance were evaluated as follows.

<< Maximum Density >> Densitometer X-rite310T
R (manufactured by X-rite) was used to measure the maximum reflection density of the image (usually the portion where the application time was the maximum).

<< Sensitivity >> The relative applied energy of each thermal transfer recording material when the applied energy when the density of the image 21 formed by the thermal transfer recording material 11 and the image receiving material 1 becomes 1.0 is set to 1. I asked. The smaller the number, the higher the sensitivity.

<< Lightfastness >> The lightfastness is shown by a dye remaining ratio after irradiating the obtained image with a xenon fade meter for 14 days. In addition, the residual ratio of the dye was represented by (D / D ₀ ) × 100, where D _{0 is} the density before light irradiation and D is the density after light irradiation.
(%).

Table 1 also shows the results.

[0105]

[Table 1]

[0106]

Embedded image

As shown in Table 1, the thermal transfer recording material using the dye of the present invention has high sensitivity, and can provide an image with high density and good image storability (light fastness). Further, by adopting the above-described preferred embodiment of the thermal transfer recording material of the present invention, it is possible to produce a more robust image recording.

Example 2 (Preparation of ink for ink jet recording) Exemplified compound 7 of the dye represented by the general formula (I) of the present invention and the metal ion-containing compound MS-1 of Example 1 were each used as an acetone solution. A concentrate of a solution in which Exemplified Compound 7 and MS-1 were mixed at a molar ratio of 1: 5 was prepared to obtain a chelate dye. This is designated as chelating dye 7K.

Using the chelating dye 7K (cyan dye) according to a standard method, an ink composition I having the following composition:
-1 was prepared. Further, an ink composition I-2 having the same composition as the ink composition I-1, except that the copper phthalocyanine compound C having the following structure was used in place of the chelate dye 7K as the cyan dye in the same mass% as in the case of the chelate dye 7K. Prepared.

(Composition of Ink Composition I-1) Cyan Dye: Chelate Dye 7K 1.4% by mass Diethylene glycol 19% by mass Triethylene glycol monobutyl ether 9% by mass Surfactant Surfynol 465 (manufactured by Air Products and Chemicals Inc.) 0.6% by mass Deionized water 70% by mass

[0111]

Embedded image

Using the prepared ink compositions I-1 and I-2, an ink jet printer MJ-5000C (manufactured by Seiko Epson Corporation, electro-mechanical conversion system), an ink jet special paper, a super fine exclusive paper MJS
A sample recorded on P1 (manufactured by Seiko Epson Corporation) was prepared, and its color tone was visually evaluated. As a result, an ink composition I-1 containing a metal chelate dye represented by formula (I) of the present invention was obtained. The sample obtained by using the ink composition I-2 exhibited a vivid cyan color, whereas the sample obtained by using the ink composition I-2 was slightly poor in saturation and the color tone was close to blue. Super Fine paper MJSP as a recording medium
Similar results were obtained when a special gloss film MJSP4 (manufactured by Seiko Epson Corporation) was used instead of 1. As described above, by using the ink for inkjet recording using the dye represented by the general formula (I) of the present invention as a metal chelate dye, a recorded image excellent in color tone can be obtained.

Example 3 (Preparation of color toner) In the same manner as in Example 2, a chelate as a chelate dye was prepared from the exemplary compound 7 of the dye represented by formula (I) of the present invention and the metal ion-containing compound MS-1. Dye 7K was prepared. 100 parts of polyester resin,
As a coloring agent, 2 parts of the above chelate dye 7K (cyan chelate dye) and 3 parts of polypropylene were mixed, kneaded, pulverized and classified to obtain a powder having an average particle size of 8.5 μm. Further, 100 parts of this powder and 1.0 part of silica fine particles (particle diameter: 12 nm, degree of hydrophobicity: 60) were mixed with a Henschel mixer to obtain a color toner 1.

Instead of 7K2 parts of the above chelate dye as a coloring agent, a comparative C pigment: C.I. I. PIGMENT B
LUE 1 (3 parts), Comparative C dye: C.I. I. SOLVE
3 parts of NTBLUE 38, or C.I. I. SOLVE
Color toner 1 except for using 3 copies of NT BLUE 70
In the same manner as in the above, color toners 2 to 4 were produced.

(Preparation of carrier) 40 g of copolymer fine particles of styrene / methyl methacrylate = 6/4, specific gravity of 5.
0, the saturation magnetization when applying an external magnetic field of 7900 A / m with a mass average diameter of 45 μm is 3.14 × 10 ⁻⁵ Wb · m /.
kg of 1960 g of Cu-Zn ferrite particles were put into a high-speed stirring type mixer and mixed at a product temperature of 30 ° C. for 15 minutes.
The temperature of the product was set at 105 ° C., and a mechanical impact force was repeatedly applied for 30 minutes, followed by cooling to prepare a carrier.

(Preparation of developer) The above carrier 418.5
g and 31.5 g of each color toner were mixed for 20 minutes by using a V-type mixer to prepare a developer for a real test.

<< Evaluation Method >> Konica 9028 was used as an image forming apparatus by using each of the prepared developers.
Using Konica Corporation, a reflection image (image on paper) and a transmission image (OHP image) were prepared on paper and OHP, respectively, and evaluated by the following methods. The toner adhesion amount was evaluated in the range of 0.7 ± 0.05 (mg / cm ² ).

Saturation: Macbeth Color-Ey
Using e7000, the saturation of the image on the prepared paper was measured and compared.

Light resistance: “Xenon Long Life Weather Meter” manufactured by Suga Test Instruments Co., Ltd. (Xenon Arc Lamp, 7
0000 lux, 44.0 ° C.) for 7 days, and then Macbeth Color-E.
The color difference from the image before the test was measured using the ye 7000,
Compared.

Transparency: Regarding the transparency of an OHP image,
The visible spectral transmittance of the image was measured using a “330-type self-recording spectrophotometer” manufactured by Hitachi, Ltd. with the OHP sheet not carrying the toner as a reference, and yellow 570 n
m, magenta 650 nm, and the spectral transmittance at 500 nm of cyan were determined and used as a measure of the transparency of the OHP image.

Hue change: Macbeth Color-
The hue difference between the prepared paper and the OHP image was measured using Eye 7000 and compared.

Table 2 shows the results.

[0123]

[Table 2]

As is clear from Table 2, the use of the color toner prepared by using the compound of the present invention shows faithful color reproduction and high OHP quality without processing a colorant in advance. Is suitable for use as a full-color toner. Further, since the light resistance is good, it is possible to provide an image which can be stored for a long time.

Example 4 (Preparation of color filter) Exemplified compound 7 and metal ion-containing compound MS-1 were prepared in the same manner as in Examples 2 and 3.
More chelating dye 7K was prepared as a chelating dye.
In order to obtain an RGB color filter, a red (R) mosaic pattern, a green (G) mosaic pattern and a blue (B) mosaic pattern were formed on a glass plate by the following method. Using the components shown below, red (R), green (G) and blue (B) photosensitive coating agents for color filters were prepared. The photosensitive polyimide resin varnish used was a photosensitive polyimide resin varnish containing a photosensitizer.

(Components of Photosensitive Coating Agent for Color Filter) R-1: Chelating Dye 7K 10 parts Photosensitive polyimide resin varnish 50 parts N-methyl-2-pyrrolidone 40 parts G-1: Coloring material G-1 10 parts Photosensitive polyimide resin varnish 50 parts N-methyl-2-pyrrolidone 40 parts B-1: Coloring material B-1 10 parts Photosensitive polyimide resin varnish 50 parts N-methyl-2-pyrrolidone 40 parts

[0127]

Embedded image

The glass plate treated with the silane coupling agent was set on a spin coater, and the above R-1 red color filter photosensitive coating agent was first added to the spin coater.
Spin coating was performed at 5 rpm for 5 seconds and then at 2000 rpm for 5 seconds. Next, prebaking was performed at 80 ° C. for 15 minutes, a photomask having a mosaic pattern was brought into close contact, and exposure was performed using a super-high pressure mercury lamp at a light amount of 900 mJ / cm ² .

Next, development and washing were performed with a dedicated developer and a dedicated rinse to form a red mosaic pattern on the glass plate. Subsequently, the green mosaic pattern and the blue mosaic pattern are converted to the green and B of G-1.
-1 is applied and baked according to the above method using a blue color filter photosensitive coating agent,
Next, a black matrix is formed according to a conventional method.
A GB color filter was obtained.

The color filter obtained as described above has excellent spectral curve characteristics, is excellent in fastness such as light resistance and heat resistance, and is also excellent in light transmittance. It had excellent properties as a color filter for use.

Similar results were obtained when a chelate dye prepared in the same manner as above using the exemplary compound 11 of the dye represented by formula (I) of the present invention instead of the above combination was used.

[0132]

According to the thermal transfer recording material and the thermal transfer recording method using the recording material according to the present invention, an image having excellent image storability such as fixability and light resistance can be obtained. Good storage stability, high sensitivity recording is possible, and an image with little secondary absorption and favorable hue for color reproduction can be obtained. Further, by using a chelate dye prepared from the dye represented by the general formula (I) and the metal ion-containing compound of the present invention, an ink jet recording ink having an excellent color tone can be obtained. A color toner that shows faithful color reproduction and high OHP quality and has excellent characteristics as a full-color toner as well as high image storability can be obtained. Furthermore, using the chelate dye, excellent spectral curve characteristics and high robustness can be obtained. A color filter having excellent properties and excellent light transmittance can be produced.

[Brief description of the drawings]

FIG. 1 is a schematic view showing one example of a thermal transfer recording method of the present invention.

FIG. 2 is a schematic view showing another example of the thermal transfer recording method of the present invention.

[Explanation of symbols]

 REFERENCE SIGNS LIST 1 support 2 image receiving layer 3 image receiving material 4 support 5 dye donating layer 6 dye donating material 7 thermal head 8 heating resistor 9 heat fusible layer 10 thermal transfer recording material

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (Reference) G02B 5/20 101 B41M 5/26 101K G03G 9/09 G03G 9/08 361 (72) Inventor Norio Miura Hino-shi, Tokyo No. 1 Sakuracho Konica Stock Company In-house F-term (reference) 2H005 AA21 CA22 2H048 BA02 BA11 BA15 BA16 BA17 BA48 BB02 BB14 BB42 2H086 BA55 2H111 AA27 BA03 BA39 BA74 CA03 CA33 4J039 BC41 BE02 BE12 CA06 CA07 EA36 EA41 EA43 GA24

Claims (8)

[Claims] 1. A heat-sensitive transfer recording material comprising a dye represented by the following general formula (I). Embedded image [Wherein, R ¹ and R ² each represent a substituted or unsubstituted alkyl group, and R ³ represents a substituent. n represents an integer of 0 to 4, when n is 2 or more, plural R ³ may be the same or different. R ⁴ represents a cycloalkyl group, secondary or tertiary alkyl group, an aryl group or a heterocyclic group,, R ⁵
Represents a hydrogen atom or a substituent, and R ⁶ and R ⁷ each represent a substituent or a group of non-metallic atoms necessary for bonding to each other to form a ring. ] 2. R ⁶ and R ⁷ in the general formula (I)
Is an alkyl group.
The thermal transfer recording material as described in the above. 3. The thermal transfer recording material according to claim 1, wherein R ⁴ in the general formula (I) is an i-propyl group or a tert-butyl group. 4. An image receiving material is superimposed on a dye donating material having a dye donating layer containing the dye represented by formula (I) on a support, and the dye donating material is heated in accordance with image information. A thermal transfer recording method comprising forming an image. 5. An image receiving material having a dye donating layer containing a dye represented by the general formula (I) on a support and a dye receiving layer containing a metal ion-containing compound on a support. Wherein the dye-donor material is heated in accordance with image information, and a metal chelate dye image is formed by a reaction between the dye and the metal ion-containing compound. 6. An ink jet recording ink comprising a metal chelate dye formed by a reaction between the dye represented by the general formula (I) and a metal ion-containing compound. 7. A color toner comprising a metal chelate dye formed by a reaction between the dye represented by the general formula (I) and a metal ion-containing compound. 8. A color filter comprising a metal chelate dye formed by reacting the dye represented by the general formula (I) with a metal ion-containing compound.