JPH11189728A - Pyrazolopyrimidine coloring matter, thermographic recording material and thermographic recording - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new coloring matter having good hue and durability to light, heat and moisture and useful in thermographic recording materials. SOLUTION: This coloring matter is that of formula I [XB is N(RB6 ) or S; QB is an atom group necessary for formation of a coloring matter having visible and/or infrared absorption; LB is N or methine; (n) is 0-2; RB1 to RB6 are each H or a substituent] e.g. a coloring matter of formula II. The coloring matter of formula I is obtained by the following procedure: 3-Amino-5-methylpyrazole, a ketone containing a cyano group and p-toluenesulfonic acid are dissolved in methanol and refluxed under agitating and heating. The resultant solution is left to cooling to room temperature then the solvent is distilled off at reduced pressure. Methanol is added to the residue therefrom and the resultant mixture is heated to dissolve the residue and is agitated under cooling by ice. The resultant compound, 4-diethylamino-o-toluidine and sodium acetate are suspended in acetonitrile, and silver oxide is added thereto under agitation and the mixture is agitated at room temperature. The insoluble matter therein is filtrated off and the solvent is distilled off at reduced pressure. Ethyl acetate is added to the residue thereafter and the insoluble matter is filtered off. The solvent is concentrated and hexane is added and the mixture is agitated and cooled by ice.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a pyrazolopyrimidine dye, a thermal transfer recording material containing the dye, and a thermal transfer recording method. More specifically, color tone, pyrazolopyrimidine dye excellent in storage stability, using the dye,
The present invention relates to a thermal transfer recording material and a thermal transfer recording method capable of obtaining an image with high density and excellent durability.

[0002]

2. Description of the Related Art Pigments known as dyes and pigments are:
It is widely used in various applications such as fiber dyeing materials, resin and paint coloring materials, image forming materials in photographs, printing, copying machines, printers, and light absorbing materials for color filters.
In recent years, various image forming dyes for color hard copy using ink jet, electrophotography, silver halide photography, thermal transfer, etc. have been proposed, and with the development of electronic imaging, dyes for solid-state imaging tubes, filters for color liquid crystal televisions, and semiconductors. The demand for dyes for optical recording media using lasers is increasing, and the fields of use of dyes are expanding.

It is desired that the above-mentioned dyes have the following properties in common. That is, having a favorable hue in color reproduction, having an optimal spectral absorption characteristic, being excellent in fastness such as light resistance, heat resistance, moisture resistance, chemical resistance, and having a large molar extinction coefficient. No.

Conventionally, as a method for obtaining a color hard copy, a color image recording technique using ink jet, electrophotography, thermal transfer, a silver halide photosensitive material, etc. has been studied.

[0005] Among them, the thermal transfer material has advantages such as easy operation and maintenance, downsizing of the apparatus and cost reduction, and low running cost.

[0006]

In the thermal transfer recording of the thermal transfer system, the dye used in the thermal transfer material is important. A thermal transfer material and an image forming method using a heat-diffusable dye capable of being chelated (hereinafter referred to as a chelate dye) for the purpose of improving the storage stability of the obtained image, particularly, the fixability and light resistance have been proposed. For example, JP-A Nos. 59-78893, 59-109349, 60
No. 2398 and the like.

Although an image formed using the chelate dye disclosed in the above patent is excellent in light fastness and fixability, it does not sufficiently satisfy the sensitivity of the heat-sensitive transfer material and the storability of the material itself. And further improvement was desired. Further, since the obtained image contains irregular absorption, it is inferior in color reproduction, and further improvement has been desired.

The present invention has been made in order to improve the above-mentioned circumstances. That is, an object of the present invention is to provide a pyrazolopyrimidine dye having a good hue and having excellent light, heat and moisture durability. Is to provide.

Another object is to provide a thermal transfer recording material for obtaining an image having excellent image storability such as fixability and light resistance, and a thermal transfer recording method using this recording material.

It is still another object of the present invention to provide a heat-sensitive transfer recording material having good preservability of an ink sheet and capable of high-sensitivity recording, and a heat-sensitive transfer recording method using the recording material.

[0011]

The above object of the present invention is attained by the following constitutions.

1. A pyrazolopyrimidine dye represented by the following general formula (BI).

[0013]

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[0014] X _B in the formula N (R _B6) or a sulfur atom, Q _B represents an atomic group necessary to form a dye having an absorption in the visible and / or Infrared, L _B is nitrogen Represents an atom or a methine group, n represents 0, 1 or 2;
R _B1 , R _B2 , R _B3 , R _B4 , R _B5 and R _B6 represent a hydrogen atom or a substituent, R _B2 and R _B3 may combine with each other to form a ring, and R _B3 and R _B6 are R _B4 and R _B5 may be bonded to each other to form a ring.

2. A pyrazolopyrimidine dye represented by the following general formula (B-II).

[0016]

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In the formula, X _B represents N (R _B6 ) or a sulfur atom, Q _B represents a group of atoms necessary for forming a dye having absorption in the visible and / or infrared region, and n is 0, 1 or 2, R _B1 , R _B2 , R _B3 , R _B4 , R _B5 and R _B6 represent a hydrogen atom or a substituent, and R _B2 and R _B3 may combine with each other to form a ring; R _B3 and R _B6 may be bonded to each other to form a ring, and R _B4 and R _B5 may be bonded to each other to form a ring.

3. A pyrazolopyrimidine dye represented by the following general formula (B-III).

[0019]

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In the formula, X _B represents N (R _B6 ) or a sulfur atom, Q _B represents an atomic group necessary for forming a dye having absorption in the visible and / or infrared region, and R _B1 , R _{B B2} , R _B3
And R _B6 represent a hydrogen atom or a substituent, and R _B2 and R _B3
May combine with each other to form a ring, and R _B3 and R _B6 may combine with each other to form a ring.

4. A support containing at least one of the pyrazolopyrimidine dyes represented by the general formula (BI), the general formula (B-II) or the general formula (B-III). Thermal transfer recording material.

5. Dye-donating layer containing, on a support, at least one dye of the pyrazolopyrimidine dyes represented by formula (B-I), formula (B-II) or formula (B-III) A heat-sensitive transfer recording method comprising superimposing an image-receiving material on a dye-providing material having the following formula, and heating the dye-providing material in accordance with image information to form an image.

6. Dye-donating layer containing, on a support, at least one dye of the pyrazolopyrimidine dyes represented by formula (B-I), formula (B-II) or formula (B-III) An image receiving material having a dye image receiving layer containing a metal ion-containing compound on a support, and heating the dye providing material in accordance with image information to form an image. Thermal transfer recording method.

Hereinafter, the present invention will be described in more detail.

The above general formulas (BI) to (B-II)
Pyrazolopyrimidine dye represented by I) (hereinafter, simply pyrazolopyrimidine dyes of the present invention, in also referred dye), X _B is N (R _B6) or a sulfur atom.

Q _B is not limited as long as it is an atomic group necessary for forming a dye having absorption in the visible and / or infrared region, and preferably includes an aromatic ring group or a heterocyclic group. Benzene ring group, naphthalene ring group, pyridine ring group, pyrimidine ring group, pyrazine ring group, triazine ring group,
Pyrazole ring group, imidazole ring group, pyrrole ring group, thiazole ring group, thiadiazole ring group, furan ring group, thiophene ring group, oxazole ring group, quinoline ring group, indole ring group, benzothiazole ring group, benzimidazole ring group, Pyrazoloimidazole ring group, pyrazolotriazole ring group, pyrazolopyrimidine-7-imine ring group, pyrazolopyrimidine-7-thione ring group, barbituric acid ring group,
Thiobarbituric acid ring group, rhodanine ring group, hydantoin ring group, thiohydantoin ring group, 2-pyrazolin-5-
On-ring group, 2-isoxazolin-5-one ring group, indane-1,3-dione ring group, cyclohexane-1,3-
Dione ring group, 1,3-dioxane-4,6-dione ring group, pyrazoline-3,5-dione ring group, pentane-2,
4-dione ring group, isoquinolin-4-one ring group, chroman-2,4-dione ring group, quinolinium ring group, pyridinium ring group, isoquinolinium ring group, 3H-indolium ring group, benzindolinium ring group, Oxazolium ring group, thiazolium ring group, selenazolinium ring group, imidazolium ring group, benzoxazolinium ring group, benzothiazolium ring group, benzoselenazolinium ring group, benzimidazolium ring group, naphthooxazorim Ring group, naphthothiazolim ring group, naphthoselenazolim ring group, thiazolinium ring group, dihydronaphthothiazolium ring group, pyrylium ring group, and imidazopyrazinium ring group.

The above general formulas (BI) and (B-II)
Alternatively, when the dye represented by formula (B-III) is supplied to a thermal transfer recording material, Q _B is preferably, for example, a benzene ring group, a naphthalene ring group, a pyridine ring group, a pyrimidine ring group, a pyrazine ring group, a triazine ring. Group, pyrazole ring group, imidazole ring group, pyrrole ring group, thiazole ring group, thiadiazole ring group, furan ring group, thiophene ring group, oxazole ring group, quinoline ring group, indole ring group, benzthiazole ring group, benzimidazole ring Group,
Pyrazoloimidazole ring group, pyrazolotriazole ring group, pyrazolopyrimidine-7-imine ring group, pyrazolopyrimidine-7-thione ring group, barbituric acid ring group, thiobarbituric acid ring group, rhodanine ring group, hydantoin Ring group, thiohydantoin ring group, 2-pyrazolin-5-one ring group, 2-isoxazolin-5-one ring group, indane-1,3-dione ring group, cyclohexane-1,3-dione ring group, 1 , 3-Dioxane-4,6-dione ring group, pyrazoline-3,5-dione ring group, pentane-2,4-dione ring group, isoquinolin-4-one ring group, chroman-
2,4-dione ring groups and the like.

The above aromatic ring or hetero ring may further have a condensed ring, and these aromatic ring or hetero ring may have a substituent atom or a substituent, for example, a halogen atom ( An alkyl group (eg, methyl, ethyl, butyl, pentyl, 2-methoxyethyl, trifluoromethyl, 2-ethylhexyl, etc.), an aryl group (eg, phenyl, p-tolyl, naphthyl, etc.), Acyl groups (eg, acetyl, propionyl,
Benzoyl, etc.), an alkoxy group (eg, methoxy, ethoxy, butoxy, etc.), an aryloxy group (eg, phenoxy group, etc.), an alkoxycarbonyl group (eg, methoxycarbonyl, i-propoxycarbonyl, etc.), an acyloxy group (eg, acetyloxy, ethylcarbonyl Carboxy, carbamoyl group (eg, methylcarbamoyl,
Ethylcarbamoyl, butylcarbamoyl, phenylcarbamoyl, etc.), sulfamoyl group (eg, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl, etc.), alkylthio group (eg, methylthio, ethylthio, octylthio, etc.), arylthio group (eg, Phenylthio, p-tolylthio, etc.), amino group (eg, amino, methylamino, diethylamino, methoxyethylamino, etc.), acylamino group (eg, acetylamino, chloroacetylamino, propionylamino, benzoylamino, trifluoroacetylamino, etc.), alkyl Ureido groups (eg, methyl ureide, ethyl ureide, methoxyethyl ureide, dimethyl ureide, etc.), aryl ureide groups (eg, phenyl ureide, etc.), Le sulfonamido group (e.g., methanesulfonamido, ethanesulfonamide, butane sulfonamide, trifluoromethyl sulfonamide,
2,2,2-trifluoroethylsulfonamide, etc.),
Arylsulfonamide group (eg, phenylsulfonamide, tolylsulfonamide, etc.), alkylaminosulfonylamino group (eg, methylaminosulfonylamino, ethylaminosulfonylamino, etc.), arylaminosulfonylamino group (eg, phenylaminosulfonylamino, etc.), hydroxy Group, cyano group, nitro group, carboxyl group, sulfonic group, heterocyclic group (for example, pyridyl, pyrazolyl, imidazolyl, furyl, thienyl, etc.)
Is mentioned. These substituents may further have a substituent.

L _B represents a nitrogen atom or a methine group, and the methine group may have a substituent or a substituent, for example, a halogen atom (eg, a fluorine atom, a chlorine atom, etc.);
An alkyl group (eg, methyl, ethyl, butyl, pentyl, 2-methoxyethyl, trifluoromethyl, 2-ethylhexyl, etc.), an aryl group (eg, phenyl, p-
Tolyl, naphthyl, etc.), acyl group (eg, acetyl, propionyl, benzoyl, etc.), alkoxy group (eg, methoxy, ethoxy, butoxy, etc.), aryloxy group (eg, phenoxy group, etc.), alkoxycarbonyl group (eg, methoxycarbonyl, i- Propoxycarbonyl, acyloxy group (eg, acetyloxy, ethylcarbonyloxy, etc.), carbamoyl group (eg, methylcarbamoyl, ethylcarbamoyl, butylcarbamoyl, phenylcarbamoyl, etc.), sulfamoyl group (eg, sulfamoyl, methylsulfamoyl, dimethylsulfa) Moyl, phenylsulfamoyl, etc.), an alkylthio group (eg, methylthio, ethylthio, octylthio, etc.), an arylthio group (eg, phenylthio, p
-Tolylthio, etc.), an amino group (eg, amino, methylamino, diethylamino, methoxyethylamino, etc.), an acylamino group (eg, acetylamino, chloroacetylamino, propionylamino, benzoylamino, trifluoroacetylamino, etc.), an alkylureido group ( For example, methyl ureide, ethyl ureide, methoxyethyl ureide, dimethyl ureide and the like, aryl ureide group (for example, phenyl ureide), alkyl sulfonamide group (for example, methane sulfonamide, ethane sulfonamide, butane sulfonamide, trifluoromethyl sulfonamide, 2,2,2-trifluoroethylsulfonamide, etc.), arylsulfonamide group (eg, phenylsulfonamide, tolylsulfonamide, etc.), alkylaminosulfonyl Amino group (e.g., methylaminosulfonyl, ethylamino sulfonylamino etc.), arylamino sulfonylamino group (e.g., phenylamino sulfonylamino etc.), hydroxy group, a carboxyl group, a sulfonic acid group, and a cyano group. These substituents may further have a substituent. n represents 0, 1 or 2, and is preferably 0 or 1.

R _B1 , R _B2 , R _B3 , R _B4 , R _B5 and R _B6
Represents a hydrogen atom, a halogen atom or a substituent. Specifically, for example, a halogen atom (eg, a fluorine atom, a chlorine atom, etc.), an alkyl group (eg, methyl, ethyl, butyl, pentyl, 2-methoxyethyl, trifluoromethyl,
-Ethylhexyl, etc.), an aryl group (e.g., phenyl,
p-tolyl, naphthyl, etc.), acyl group (eg, acetyl, propionyl, benzoyl, etc.), alkoxy group (eg, methoxy, ethoxy, butoxy, etc.), alkoxycarbonyl group (eg, methoxycarbonyl, i-propoxycarbonyl, etc.), acyloxy group ( For example, acetyloxy, ethylcarbonyloxy, etc.), carbamoyl group (eg, methylcarbamoyl, ethylcarbamoyl, butylcarbamoyl, phenylcarbamoyl, etc.), sulfamoyl group (eg, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl, etc.) An alkylthio group (eg, methylthio, ethylthio, octylthio, etc.), an arylthio group (eg, phenylthio, p-tolylthio, etc.), an amino group (eg, amino, methylamino, die Amino, methoxyethylamino, etc.), acylamino groups (eg, acetylamino, chloroacetylamino, propionylamino, benzoylamino, trifluoroacetylamino, etc.), alkylureido groups (eg, methylureide, ethylureide, methoxyethylureide, dimethylureide, etc.) ), Arylureido groups (eg, phenylureido), alkylsulfonamide groups (eg, methanesulfonamide, ethanesulfonamide, butanesulfonamide, trifluoromethylsulfonamide, 2,2,2-trifluoroethylsulfonamide, etc.), Arylsulfonamide group (eg, phenylsulfonamide, tolylsulfonamide, etc.), alkylaminosulfonylamino group (eg, methylaminosulfonylamino, ethylamino Ruphonylamino, etc.), arylaminosulfonylamino group (eg, phenylaminosulfonylamino), hydroxy group, cyano group, nitro group, carboxyl group, sulfonic acid group, heterocyclic group (eg, pyridyl, pyrazolyl, imidazolyl, furyl, thienyl, etc.) And the like. R _B2 and R
_B3 may combine with each other to form a ring, R _B3 and R _B6 may combine with each other to form a ring, and R _B4 and R _B5 may combine with each other to form a ring.

The following formulas (BI) and (BI)
Specific examples of the dye represented by I) or the general formula (B-III) are shown below, but the present invention is not limited thereto.

[0032]

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[0033]

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[0034]

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[0035]

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[0036]

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[0037]

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[0038]

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[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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The case where the dye of the present invention is used in a thermal transfer recording material will be described.

The dye-providing material used in the thermal transfer recording of the present invention is a pyrazolopyrimidine of the present invention represented by the formula (BI), (B-II) or (B-III) on a support. It has a dye donating layer having a dye.

The dyes of the present invention may be used alone or in combination of two or more. Further, other dyes such as azo dyes and anthraquinone dyes may be added as long as the effects of the present invention are not impaired. The content of the dye according to the present invention in the dye-providing layer is preferred supports 1 m ² per 0.05 to 10 g. The dye-donating layer is prepared by dissolving the dye of the present invention together with a binder in a solvent, or by dispersing the dye of the present invention in the form of fine particles in a solvent to prepare an ink liquid for forming a dye-donating layer. It can be formed by adding non-sublimable fine particles, a dispersant, an antistatic agent, an antifoaming agent, an antioxidant, a viscosity modifier and the like, applying the ink liquid on a support, and appropriately drying the ink liquid. . The thickness of the dye-donor layer is 0.1 to
10 μm 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. Examples of the organic solvent include alcohols (eg, ethanol, propanol), cellosolves (eg, methylcellosolve), aromatics (eg, toluene, xylene), esters (eg, acetate), ketones (eg, acetone, methylethylketone). And ethers (eg, tetrahydrofuran, dioxane) and the like.

The support has good dimensional stability,
Any material that can withstand the heating of the thermal head during recording may be used, but thin paper such as condenser paper or glassine paper, or a heat-resistant plastic film such as polyethylene terephthalate, polyamide, or polycarbonate is preferably used. The thickness of the support is preferably 2 to 30 μm, and the support is provided with an undercoat layer made of a polymer selected for the purpose of improving adhesiveness with a binder, transferring a dye to the support, and preventing dyeing. It is preferred to have. Further, a slipping layer may be provided on the back surface of the support (the side opposite to the dye-donating layer) for the purpose of preventing the head from sticking to the support.

The dye-donor material of the present invention is used on a dye-donor layer or on a support on which a dye-donor layer is applied, for the purpose of using an image-receiving material described later, which is not particularly provided with an image-receiving layer, such as plain paper. May have a heat-fusible layer containing a heat-fusible compound as described in JP-A-59-106997. As the heat-fusible compound, a colorless or white compound that melts at a temperature of 65 to 150 ° C. is preferably used, and examples thereof include waxes such as carnauba wax, beeswax, and candeline wax.
Note that these heat-meltable layers 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 a heat-sensitive transfer recording material capable of full-color image recording, a cyan dye-donating layer containing a cyan dye, a magenta dye-donating layer containing a magenta dye, and a yellow dye are used. It is preferred that a total of three layers of the contained yellow dye-donor layer are sequentially and repeatedly coated on the same surface on the support. If necessary, a total of 4 dye-donor layers containing a black image-forming substance may be used.
The layers may be sequentially and repeatedly applied on the same surface.

In the thermal transfer recording method of the present invention, the above general formula (BI), (B-II) or (B-III)
Superimposing an image-receiving material on a dye-donor material having a dye-donor layer containing at least one of the dyes represented by the formula, heating the dye-donor material according to image information, and transferring the dye to form an image. Features.

Further, the dye according to the present invention and a metal ion-containing compound can be used in combination. The dye represented by the general formula (BI), (B-II) or (B-III) is a pyrazolopyrimidine ring (the following general formula (BI)
Chelate formed between the nitrogen atom or sulfur atom represented by the nitrogen atom and X _B of 1-position on the V)) is considered to be possible.

[0055]

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That is, the general formula (B-
A dye image-receiving layer containing a metal ion-containing compound is provided on a support on a dye-donating material having a dye-donating layer containing at least one of the dyes represented by I), (B-II) or (B-III). The dye-receiving material is heated according to image information, and the image is formed by a metal chelate dye formed by a reaction between the dye and the metal ion-containing compound (hereinafter referred to as a metal source). This is a thermal transfer recording method. Further, the metal source may be present in the image receiving material, or may be present in the heat-meltable layer provided on the dye-providing material.

Examples of the metal source include inorganic or organic salts and metal complexes of metal ions. Among them, salts and complexes of organic acids are preferable. Metals include I to VI of the periodic table
Examples include monovalent and polyvalent metals belonging to Group II. Among them, Al, Co, Cr, Cu, Fe, Mg, Mn, Mo,
Ni, Sn, Ti and Zn are preferred, especially Ni, C
u, Cr, Co and Zn are preferred. Specific examples of the metal source include Ni ²⁺ , Cu ²⁺ , Cr ²⁺ , Co ²⁺ and Z 2.
Examples include n ²⁺ and an aliphatic salt such as acetic acid or stearic acid, or a salt of an aromatic carboxylic acid such as benzoic acid or salicylic acid.

Further, a complex represented by the following general formula (9) can be particularly preferably used.

[0059] Formula _{(9) {Me (Q 1} ) q 1 (Q 2) q 2 (Q 3) q 3} p + (V -) p where in the above formulas, Me is a metal ion, preferably N
i2 ⁺ , Cu2 ⁺ , Cr2 ⁺ , Co2 ⁺ , and Zn2 ⁺ .

Q ₁ , Q ₂ and Q ₃ each represent a coordination compound capable of coordinating with a metal ion represented by Me, 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).

V ⁻ represents an organic anion group, and specific examples include a tetraphenylboron anion and an alkylbenzenesulfonic acid anion. q ₁ is 1, 2
Or q represents an integer of 3, q ₂ represents 1, 2 or 0, and q ₃ represents 1 or 0, and these represent whether the complex represented by the general formula is tetradentate or hexadentate. Or the number of ligands of Q ₁ , Q ₂ , Q ₃ .

P represents 0, 1 or 2. When p is 0, the coordination compound represented by Q is an anionic compound, and the anionic compound represented by Q and the metal cation represented by Me are electrically neutralized. Means that. As the anionic compound, the following general formula (10)
The compound represented by is preferred.

[0063]

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R ₁₁ and R ₁₃ each represent an alkyl group or an aryl group which may be the same or different, and R ₁₂ represents an alkyl group, an alkoxy group, a halogen atom, an alkoxycarbonyl group, or a hydrogen atom. The addition amount of the metal source is usually 0.5 to 2 with respect to the image-receiving material or the heat-fusible layer.
Preferably ^{0g / m 2, 1~15g / m} 2 is more preferable.

The image receiving material of the present invention is generally made of paper, a plastic film, or a paper-plastic film composite as a support, on which a polyester resin, polyvinyl chloride resin, vinyl chloride and other monomers are formed as an image receiving layer. One or two or more polymer layers of a copolymer resin (for example, vinyl acetate or the like), polyvinyl butyral, polyvinyl pyrrolidone, polycarbonate or the like are formed. In the image receiving material, a protective layer may be provided on the image receiving layer for the purpose of preventing fusion, and an intermediate layer may be provided between the support and the image receiving layer for the purpose of adhesion, heat insulation, or cushioning. Further, the support itself may be used as an image receiving material.

In the thermal transfer recording method, heating by a thermal head is generally used, but heating by electric current or heating using a laser may be used. The application of heat by a thermal head etc.
It may be carried out from the back side of the dye-providing material or from the back side of the image-receiving material without any particular limitation. However, the back side of the dye-providing material is preferable in consideration of the transfer speed of the dye and the image density. Further, before the transfer of the dye, during the transfer, or after the transfer, further heating can be performed to promote the transfer of the dye, the reaction with the metal source, and the fixing of the transferred dye.

Next, an example of the thermal transfer recording method of the present invention will be described with reference to FIGS. 1 (a) and 1 (b).

In the thermal transfer recording material of FIG.
The image receiving material 3 comprises an image receiving layer 2 containing a metal ion-containing compound provided on a support 1, and a dye donating material 6 comprises a dye donating layer 5 containing the dye of the present invention on a support 4. It is provided and configured. The image receiving material 3 and the dye donating material 6 may each be provided with 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 superimposed, and heat is applied from the back side of the dye-providing material 6 to a heating resistor 8 carried on a thermal head 7 in accordance with image information. This is achieved by exfoliating both materials. At this time, a metal complex dye image formed by the reaction between the dye in the dye donating layer 5 and the metal ion-containing compound in the image receiving layer 2 is formed.

In the heat-sensitive transfer recording material of FIG. 1B, a heat-meltable layer 9 containing a metal ion-containing compound is laminated on the dye-providing material 6 of the heat-sensitive transfer recording material of FIG. The thermal transfer recording material 10 and the image receiving material 3 having no image receiving layer, such as the above-mentioned plain paper, are superimposed on each other, as shown in FIG.
The thermal head 7 is used in the same manner as in the thermal transfer recording method (a), and then the two materials are peeled off to form an image. In this method, when heat is applied by the thermal head 7, the metal complex dye is reacted between the dye-donating layer 5 and the heat-meltable layer 9 on the thermal transfer recording material 10 by reacting the dye with the metal ion-containing compound. Is generated, and then an image is formed on the image receiving material 3.

[0070]

Next, the present invention will be described in more detail by way of examples, but embodiments of the present invention are not limited thereto.

Example 1 Synthesis of Exemplified Dye (B-2)

[0072]

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In a 1000 ml eggplant type flask, 30 g of 3-amino-5-methylpyrazole (compound (1)), 56.8 g of compound (2) and 3 g of p-toluenesulfonic acid were dissolved in 400 ml of methanol and stirred for 4 hours. Heated to reflux. After allowing to cool to room temperature, the solvent was distilled off under reduced pressure. After 100 ml of methanol was added to the residue and dissolved by heating, the mixture was stirred under ice-cooling, and the resulting crystals were collected by filtration. From NMR, compound (3)
Was identified. Yield 40.8 g (57% yield).

Compound (3) (15 g), Compound (4)
8 g and sodium acetate 42.4 g were mixed with acetonitrile 30
0 ml, and with vigorous stirring, add silver oxide 1
8.0 g was added little by little, and the mixture was stirred at room temperature for 1 hour. After filtering off the insoluble matter and distilling off the solvent under reduced pressure, 100 ml of ethyl acetate was added to the residue, and the insoluble matter was filtered off. After the solvent was concentrated to about 1/3, hexane was added, and the mixture was stirred under ice cooling, and the resulting dark blue crystals were collected by filtration. Yield 7.3 g (Yield 28
%). 1H-NMR, mass spectrum, and elemental analysis confirmed that the product was the desired product. 1H-NMR spectrum (60MH
z, MeOH-d1) δ 1.20-1.30 (t 6
H), δ 1.50-1.70 (t, s 12H), δ
2.50-2.70 (s 3H), δ 2.90-3.5
0 (s, m 5H), δ 3.50-3.80 (m 4
H), δ 6.50-7.80 (m 3H), mass spectrum m / e 406 (M ⁺ ), elemental analysis (calculated) C:
70.90, H: 8.43, N: 20.67, (actual value) C: 71.20, H: 8.48, N: 20.32.
The UV-visible absorption spectrum of this dye in an acetone solution had a maximum absorption at 612 nm and sharp spectral characteristics with almost no side absorption in the visible light region.

Example 2 Synthesis of Exemplified Dye (B-5)

[0076]

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In a 1000 ml eggplant type flask, 15 g of 3-amino-5-methylpyrazole (compound (1)), 32.0 g of compound (5), and 1.5 g of p-toluenesulfonic acid
Was dissolved in 300 ml of methanol, and the mixture was heated and refluxed for 3 hours while stirring. After allowing to cool to room temperature, the solvent was distilled off under reduced pressure.
70 ml of methanol was added to the residue, and the mixture was dissolved by heating. It was identified as compound (6) by NMR. Yield 23.1 g (73% yield).

10 g of the compound (6) was added to 100 ml of toluene.
And 3 g of molecular sieve 3A and 3 g of titanium (IV) chloride were suspended therein. A solution of 5.2 g of compound (7) dissolved in 40 ml of toluene was added dropwise over 4 hours, and stirring was continued for 36 hours. Filter the solids,
After the solvent was distilled off under reduced pressure, 30 ml of ethyl acetate was added to the residue, and the insoluble matter was separated by filtration. After the solvent was concentrated to about 1/3, hexane was added, the mixture was stirred under ice-cooling, and the generated crystals were collected by filtration. The compound (8) was identified by NMR. Yield 6.6
g (49% yield).

6.6 g of the compound (8) was dissolved in 30 ml of acetic acid, and under ice-cooling, 1.65 g of sodium nitrite was added little by little as a powder. After stirring was continued for 1 hour as it was, the contents were added to 300 ml of ice water, and the resulting precipitate was collected by filtration. The compound (9) was identified by NMR. Yield 7.
2 g (99% yield).

Dissolve 7.2 g of compound (9) in 40 ml of tetrahydrofuran and add 5% palladium on carbon catalyst 5
After adding 0 mg, catalytic reduction was performed at normal pressure. The catalyst was filtered off using a filter aid, 1 g of p-toluenesulfonic acid was added to the solution, and the mixture was heated under reflux for 2 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure, ethyl acetate was added to the residue to dissolve it, hexane was added, the mixture was stirred under ice-cooling, and the resulting crystals were collected by filtration. It was identified as compound (10) by NMR. Yield 5.8 g (95% yield).

4.8 g of compound (4), compound (10)
5.8 g and sodium acetate 12 g were added to acetonitrile 10
0 ml and suspended under vigorous stirring.
3 g was added little by little, and the mixture was stirred at room temperature for 1 hour. After filtering off the insoluble matter and distilling off the solvent under reduced pressure, ethyl acetate was added to the residue.
00 ml was added, and the insoluble matter was separated by filtration. After evaporating the solvent under reduced pressure, 30 ml of acetonitrile was added, and the mixture was stirred under ice-cooling, and the resulting dark blue crystals were collected by filtration. Yield 1.65 g (Yield 1
7%). It was confirmed as the target substance by mass spectrum and elemental analysis. Mass spectrum m / e 433 (M ⁺ ), elemental analysis (calculated) C: 66.49, H: 7.21, N: 22.
61, (actual value) C: 66.11, H: 7.33, N:
22.82.

Embodiment 3

[0083]

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Synthesis of Exemplified Dye (B-7) Compound (11) synthesized by the same method as compound (3)
5.0 g, compound (12) 6.2 g, piperidine 2.1
g was suspended in 100 ml of toluene and heated under reflux for 5 hours. After filtering off the insoluble matter and distilling off the solvent under reduced pressure, 30 ml of acetonitrile was added to the residue, and the mixture was stirred under ice-cooling, and the resulting reddish purple crystals were collected by filtration. Yield 1.2 g (12% yield).
It was confirmed as the target substance by mass spectrum and elemental analysis. Mass spectrum m / e 397 (M ⁺ ), elemental analysis (calculated value)
C: 66.46, H: 7.86, N: 17.61, (actual value) C: 66.52, H: 7.74, N: 17.2
5.

Example 4 Synthesis of Exemplified Dye (B-11)

[0086]

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12.0 g of the compound (13) synthesized in the same manner as the compound (6) was dissolved in 60 ml of acetic acid, and 2.8 g of sodium nitrite was added little by little under ice-cooling. After continuing stirring for 1 hour, ice water 5
The contents were added to 00 ml, and the resulting precipitate was collected by filtration. NM
Based on R, it was identified as compound (14). Yield 12.8 g (97% yield).

12.5 g of the compound (14) was dissolved in 100 ml of tetrahydrofuran, and 0.1 g of a 5% palladium carbon catalyst was added thereto, followed by catalytic reduction at normal pressure. The catalyst was removed by filtration using a filter aid, 4.29 g of triethylamine was added to the solution, and trifluoroacetic anhydride (1
5) 8.9 g was added dropwise over 10 minutes. Then 1 at room temperature
After stirring for an hour, the solvent was distilled off under reduced pressure, toluene was added to the residue, and the organic layer was washed with saturated saline. Separate the organic layer,
Anhydrous sodium sulfate was added for dehydration. After the desiccant was filtered off, 10 g of anhydrous sodium sulfate was added again, and the mixture was heated to reflux while passing ammonia gas through it. After allowing to cool to room temperature, the solvent was distilled off under reduced pressure, acetonitrile was added to the residue, and the mixture was stirred under ice-cooling, and the resulting crystals were collected by filtration. It was identified as compound (16) by NMR. 7.5 g (yield 61)
%).

Compound (16) 7.5 g, Compound (12)
5.5 g and 2.2 g of piperidine were suspended in 100 ml of toluene and heated under reflux for 6 hours. After insoluble matter was filtered off and the solvent was distilled off under reduced pressure, methanol (20 ml) was added to the residue, and the mixture was stirred under ice-cooling, and the resulting blue-violet crystals were collected by filtration. Yield 3.
0 g (24% yield).

The product was identified as the target product by mass spectrum and elemental analysis. Mass spectrum m / e 512 (M ⁺ ), elemental analysis (calculated value) C: 56.24, H: 4.52, N: 2
1.86, (actual value) C: 56.13, H: 4.61,
N: 21.52.

Example 5 Synthesis of Exemplified Dye (B-16)

[0092]

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In a 100 ml eggplant flask, 2-methyl-
18 g of 5-methoxybenzthiazole (17) and 20 g of ethyl tosylate were added, and heated and stirred at 150 ° C. for 1 hour.
After standing to cool overnight and cooling, acetone was added for precipitation to obtain 36 g of compound (18) (95% yield).

36 g of the compound (18) and 18.6 g of diphenylformamidine (19) were put in a 200 ml eggplant-shaped flask, and heated and stirred at 130 ° C. for 10 minutes. Next, 60 ml of acetic anhydride was added, and the mixture was further heated and stirred for 10 minutes. After cooling, the reaction solution was added to isopropyl ether, and the resulting precipitate was collected by filtration to obtain 17.4 g of compound (20) (yield: 35%).

10.0 g of compound (21) synthesized in the same manner as compound (6) was dissolved in 60 ml of toluene.
3A3g of molecular sieve, titanium (IV) chloride
3 g were suspended. A solution of 7.3 g of compound (22) dissolved in 20 ml of toluene was added dropwise over 4 hours, and stirring was continued for 36 hours. After the solid was filtered off and the solvent was distilled off under reduced pressure, 30 ml of ethyl acetate was added to the residue, and the insolubles were filtered off. After the solvent was concentrated to about 1/3, hexane was added, the mixture was stirred under ice-cooling, and the generated crystals were collected by filtration. NMR
The compound (23) was identified. Yield 5.1 g (Yield 3
1%).

In a 100 ml eggplant flask, compound (2
0) 9.3 g, compound (23) 5.1 g, pyridine 20
and 1 ml of triethylamine, and the mixture was stirred while heating, and then 3 ml of acetic anhydride was added. After heating and stirring at 100 ° C. for 30 minutes, the reaction solution was added to 100 ml of 1N hydrochloric acid aqueous solution, and extracted with 80 ml of ethyl acetate. The ethyl acetate phase was washed with a 10% aqueous sodium bicarbonate solution, concentrated under reduced pressure, and the resulting precipitate was collected by filtration. The crystals were recrystallized from acetonitrile, and the resulting reddish purple crystals were collected by filtration. Yield 2.7 g (Yield 30)
%). It was confirmed as the target substance by mass spectrum and elemental analysis. Mass spectrum m / e 505 (M ⁺ ), elemental analysis (calculated value) C: 68.87, H: 7.77, N: 13.
85, (actual value) C: 68.60, H: 7.87, N:
13.84.

Example 6 Synthesis of Exemplified Dye (B-18)

[0098]

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Compound (21) 10.0 g was added to toluene 60
Then, 3 g of molecular sieve 3A and 3 g of titanium (IV) chloride were suspended therein. Compound (24) 6.
A solution of 2 g dissolved in 20 ml of toluene was added dropwise over 3 hours, and stirring was continued for 48 hours. The solid was filtered off and the solvent was distilled off under reduced pressure.
l was added and the insolubles were filtered off. After the solvent was concentrated to about 1/3, hexane was added, the mixture was stirred under ice-cooling, and the generated crystals were collected by filtration. The compound (25) was identified by NMR. Yield 5.0 g (33% yield).

The compound (2) was placed in a 100 ml eggplant flask.
6) 3.3 g, compound (25) 5.0 g, pyridine 10
and 1 ml of triethylamine, and the mixture was stirred while heating, and then 3 ml of acetic anhydride was added. After heating and stirring at 100 ° C. for 30 minutes, the reaction solution was added to 100 ml of 1N hydrochloric acid aqueous solution, and extracted with 80 ml of ethyl acetate. The ethyl acetate phase was washed with a 10% aqueous sodium bicarbonate solution, concentrated under reduced pressure, and the resulting precipitate was collected by filtration. The crystals were recrystallized from acetonitrile, and the resulting blue-violet crystals were collected by filtration. Yield 2.8 g (Yield 35
%). It was confirmed as the target substance by mass spectrum and elemental analysis. Mass spectrum m / e 423 (M ⁺ ), Elemental analysis (calculated) C: 76.56, H: 6.90, N: 16.
53, (actual value) C: 76.50, H: 6.95, N:
16.53.

Example 7 Synthesis of Illustrative Dye (B-21)

[0102]

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6.2 g of 8-aminoquinoline (27) was dissolved in 13 ml of concentrated hydrochloric acid, and sodium nitrite was added under ice cooling.
3 g were added in small portions. 11.5 g of compound (25) and 13 g of triethylamine were dissolved in 200 ml of methanol, and the above solution was added little by little under ice-cooling. The mixture was stirred for 1 hour under ice cooling, and the resulting precipitate was collected by filtration. Recrystallization from acetonitrile gave reddish purple crystals. Yield 5.7g
(Yield 31%). It was confirmed as the target substance by mass spectrum and elemental analysis. Mass spectrum m / e 421 (M ⁺ ), elemental analysis (calculated value) C: 71.24, H: 5.50, N:
23.26, (actual value) C: 70.95, H: 5.4
0, N: 23.10.

Example 8 Synthesis of Exemplified Dye (B-24)

[0105]

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5.0 g of compound (28) and 9.2 g of Lawson's reagent (29) synthesized by the same method as compound (6).
Was dissolved in 100 ml of toluene and heated under reflux for 8 hours.
After allowing to cool to room temperature and washing with a saturated aqueous sodium hydrogen carbonate solution, the residue was purified by silica gel column chromatography. Yield 4.6 g (82% yield). The compound (30) was identified by NMR.

4.6 g of compound (30), compound (31)
4.2 g and 12.0 g of potassium carbonate in acetonitrile 3
The mixture was suspended in 00 ml, and while vigorously stirring, 5.43 g of silver oxide was added thereto little by little, followed by stirring at room temperature for 1 hour. After filtering off the insoluble matter and distilling off the solvent under reduced pressure, 100 ml of ethyl acetate was added to the residue, and the mixture was washed with a saturated aqueous sodium chloride solution and the organic layer was extracted. After dehydration with anhydrous sodium sulfate, the desiccant was filtered off, and the solvent was concentrated to about 1/3.
Hexane was added, and the mixture was stirred under ice cooling, and the resulting dark blue crystals were collected by filtration. Recrystallized from methanol. Yield 2.2 g
(Yield 27%).

The product was identified as the target product by 1H-NMR, mass spectrum and elemental analysis. 1H-NMR spectrum (60
MHz, chloroform-d1) δ 1.20-1.30
(T 6H), δ 1.50-1.70 (t, d 9
H), δ 2.50-2.70 (s 3H), δ 3.00
-3.50 (s, m 6H), δ 3.50-3.80
(M 4H), δ 6.50-9.00 (d 2H), mass spectrum m / e 410 (M ⁺ ), elemental analysis (calculated) C: 64.36, H: 7.36, N: 20.47 ,
(Actual value) C: 64.72, H: 7.35, N: 20.
01. The ultraviolet-visible light absorption spectrum of this dye in an acetone solution had a maximum absorption at 625 nm, and had sharp spectral characteristics with almost no side absorption in the visible light portion.

Example 9-Evaluation of storage stability of dye-A forced deterioration test was performed on the exemplified dye (B-2) by the following method. For evaluation, this sample was prepared as an ink, and a support (YUPO FPG-150, manufactured by Oji Yuka Synthetic Synthetic Paper)
And the color was visually evaluated.

The sample stored at room temperature was coated in the same manner and the color was visually evaluated.

Heat resistance test: 1 g of a dye was placed in a Petri dish,
It was stored for one month in a thermostat (internal temperature 55 ° C., internal humidity 20%).

Moisture resistance test: 1 g of a dye was placed in a petri dish,
It was stored for one month in a thermostat (internal temperature 40 ° C., internal humidity 80%).

-Preparation of Ink- The following raw materials were mixed to obtain an ink in a uniform solution containing the dye according to the present invention.

The solubility of the dye was good, and the suitability for ink formation was also good.

Illustrative Dye (B-2) 0.7 g Polyvinyl acetoacetal resin (KY-24, manufactured by Denki Kagaku Kogyo) 1.1 g Methyl ethyl ketone 27 ml Toluene 1.5 ml The dyes shown in Table 1 were evaluated in the same manner as described above. Was.

[0116]

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[0117]

[Table 1]

As is clear from Table 1, the dyes of the present invention have excellent storage stability.

Example 10 -Preparation of ink- The ink was prepared in the same manner as in Example 9.

-Preparation of Dye Donor Material- The above-mentioned ink liquid was applied on a 4.5 μm-thick polyethylene terephthalate base using a wire bar so that the applied amount after drying was 2.3 g / m ² , followed by drying. A dye-donor material-1 was prepared by forming a heat-sensitive transfer layer on a polyethylene phthalate film. A nitrocellulose layer containing a silicon-modified urethane resin (SP-2105, manufactured by Dainichi Seika) is provided on the back surface of the polyethylene terephthalate base as a sticking preventing layer.

Dye-donating materials 2 to 13 using the dyes shown in Table 2 were prepared in the same manner as described above.

-Preparation of Image Receiving Material- A coating liquid having the following composition was dried on a support (polyethylene layer on one side containing white pigment (TiO ₂ ) and a bluing agent) on which polyethylene was laminated on both sides of paper. Is 7.
It was coated and dried so as to have a weight of 2 g, whereby an image receiving material-1 was prepared. Further, an image receiving material-2 having the same composition as the image receiving material-1 except that the metal source was removed from the image receiving material-1 was prepared.

Metal source (described below) 4.0 g Polyvinyl butyral resin (BX-1, manufactured by Sekisui Chemical Co., Ltd.) 6.0 g Polyester modified silicone 0.3 g-Thermal transfer recording method-The dye-donor material and the image-receiving material are overlapped. The thermal head was applied from the back side of the dye-providing material, and image recording was performed with a thermal printer to obtain images-1 to 12 having excellent gradation.

After recording, the maximum density of the image, the sensitivity of the recording material, and the image storability were evaluated as follows. Table 2 shows the results.

Evaluation of maximum density: X-Rite310TR
, The maximum reflection density of the image (usually, the portion where the application time was the maximum) was measured.

Evaluation of sensitivity: When the density of the image formed with Dye Donor Material-11 was 1.0, the applied energy was 1
Then, the relative applied energy of each material was determined.
The smaller the number, the higher the sensitivity.

Evaluation of light fastness: The obtained image was irradiated with light for 10 days using a xenon fade meter to evaluate the light fastness.

Table 2 shows the results of the dye residual ratio after light irradiation. The dye residual ratio is represented by D / D0 × 100, where D0 is the density before light irradiation and D is the density after light irradiation.

[0129]

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[0130]

[Table 2]

As shown in Table 2, it can be seen that the thermal transfer recording material using the dye of the present invention has a high maximum density, is excellent in sensitivity, and shows good light fastness. Further, it can be seen that a good image excellent in light resistance can be obtained by forming a chelate image on the image receiving material.

Example 11 Each of the dye-providing materials prepared in Example 10 was treated at 50 ° C. for 100 hours.
After leaving for a time, the storage stability was evaluated.

That is, the image-receiving material was rubbed against the dye-donor layer after storage, and contamination due to the transfer of the dye was visually observed.

As a result, the dye of the present invention showed almost no staining without migration of the dye, whereas the comparative dye was stained by the dye.

Example 12 Each image obtained in Example 10 was left at 50 ° C. for 100 hours, and the fixability of the image dye was evaluated.

That is, the blur of the image after storage was visually observed. As a result, with the dye according to the present invention, almost no image bleeding was observed, but with the comparative dye, image bleeding was observed and image blurring was observed. Further, in the image containing the metal source in the image receiving material, there was no bleeding of the image at all, and excellent fixability of the dye was exhibited.

[0137]

As demonstrated in the examples, the dyes according to the present invention have good hue, and are excellent in light, heat and moisture durability,
The heat-sensitive transfer recording material according to the present invention and the heat-sensitive transfer recording method using this recording material can provide an image having excellent image storability such as fixability and light fastness, and have good storability of the ink sheet and high sensitivity. Recording is possible and has an excellent effect.

[Brief description of the drawings]

FIGS. 1A and 1B are schematic cross-sectional views showing a thermal transfer recording material 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 heat generating resistor 9 heat fusible layer 10 thermal transfer recording material

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Atsushi Asatake 1 Konica Corporation, Sakuracho, Hino City, Tokyo In-house (72) Inventor Hiroshi Kita 1 Konica Corporation, Sakuracho 1 Hino-shi, Tokyo

Claims (6)

[Claims] 1. A pyrazolopyrimidine dye represented by the following general formula (BI). Embedded image [Wherein X _B is N (R _B6) or a sulfur atom, Q _B represents an atomic group necessary to form a dye having an absorption in the visible and / or Infrared, L _B is or a nitrogen atom Represents a methine group, n represents 0, 1 or 2, R _B1 , R _B2 ,
R _B3 , R _B4 , R _B5 and R _B6 represent a hydrogen atom or a substituent, R _B2 and R _B3 may be bonded to each other to form a ring, and R _B3 and R _B6 may be bonded to each other to form a ring. May be formed,
R _B4 and R _B5 may combine with each other to form a ring. ] 2. A pyrazolopyrimidine dye represented by the following general formula (B-II). Embedded image [Wherein X _B represents N (R _B6 ) or a sulfur atom, Q _B represents an atomic group necessary for forming a dye having absorption in the visible and / or infrared region, and n represents 0, 1 or 2 and R
_B1 , R _B2 , R _B3 , R _B4 , R _B5 and R _B6 represent a hydrogen atom or a substituent, R _B2 and R _B3 may combine with each other to form a ring, and R _B3 and R _B6 R _B4 and R _B5 may be bonded to each other to form a ring. ] 3. A pyrazolopyrimidine dye represented by the following general formula (B-III). Embedded image [Wherein X _B represents N (R _B6 ) or a sulfur atom, Q _B represents an atomic group necessary for forming a dye having absorption in the visible and / or infrared region, and R _B1 , R _B2 , R _B3 and R _B6 represent a hydrogen atom or a substituent, and R _B2 and R _B3 may be bonded to each other to form a ring, or R _B3 and R _B6 may be bonded to each other to form a ring. ] 4. At least one dye of the pyrazolopyrimidine dye represented by the general formula (BI), the general formula (B-II) or the general formula (B-III) is provided on a support. A heat-sensitive transfer recording material characterized by containing. 5. A pyrazolopyrimidine dye represented by the general formula (BI), the general formula (B-II) or the general formula (B-III) on a support, A heat-sensitive transfer recording method comprising superimposing an image-receiving material on a dye-providing material having a dye-providing layer, and heating the dye-providing material in accordance with image information to form an image. 6. A pyrazolopyrimidine dye represented by the general formula (BI), the general formula (B-II) or the general formula (B-III), which is provided on a support. Superimposing an image receiving material having a dye image receiving layer containing a metal ion-containing compound on a support on a dye donating material having a dye donating layer, and heating the dye donating material according to image information to form an image. A thermal transfer recording method comprising: