JPH07281371A - Silver halide color photographic sensitive material - Google Patents

Abstract

PURPOSE:To provide the color photosensitive material superior in heat resistance and lightfastness of a color image and small in deterioration of density even by processing with a fatigued bleaching solution and reduced in secondary absorption in blue parts and improved in color development performance. CONSTITUTION:The photosensitive material contains a cyan coupler represented by formula I or II in which each of R1 and R2 is H or an aliphatic group or aromatic group or the like; X is H or a group to be released by coupling with the oxidation product of a color developing agent; R4 is -NR5(R6) or -OR7; each of R6 and R6 is H or an aliphatic group or the like; R7 is an aliphatic or aromatic or heterocyclic group; and X is H or a group to be released by coupling with the oxidation product of a color developing agent.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a cyan dye-forming coupler (cyan coupler), particularly, a --CONH- group is substituted at the 2-position, and the cyan coupler at the 2-position or the 5-position is used in a silver halide color photographic light-sensitive material. The present invention relates to a silver halide color photographic light-sensitive material having a diffusible ballast group and containing a 1-naphthol cyan coupler substituted at the 5-position with a thiocarbonylamino group or an oxazamide group.

[0002]

2. Description of the Related Art A silver halide color photographic light-sensitive material is exposed and then color-developed, whereby an oxide of a paraphenylenediamine color developing agent reacts with a coupler to form a dye, thereby forming a color image. It

Generally, in this photographic method, a color reproduction method by a subtractive color method is used to form yellow, magenta, and cyan color images.

Typical examples of cyan dye-forming couplers (cyan couplers) are phenols and naphthols. Among them, naphthols are capable of sufficiently long-wavelength and have high coupling reactivity, so that they are color negative films. Used for.

Conventionally, naphthols substituted with a carbamoyl group at the 2-position have been used as cyan couplers, but cyan dyes of this type are susceptible to reductive bleaching and, when treated with a fatigued bleaching solution, the color density is reduced. There was a problem. On the other hand, a technique for improving the above problems by newly introducing a substituent at the 5-position of 1-naphthols is described in JP-A-60-237448, 61-153640 and 63-208042. ing. The compounds described in the above-mentioned published patents show improvement in reduction fading of cyan dyes and reduction in concentration by fatigue bleaching solution treatment, but secondary absorption of blue part of the cyan dyes is not preferable in color reproduction, Improvement is desired. Further, further improvement in coupling reactivity is desired.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to improve the above problems of the prior art, and the first object is to
Another object of the present invention is to provide a silver halide color photographic light-sensitive material containing a 1-naphthol type cyan coupler which is excellent in fastness against heat and light of a color image. The second object is to provide a silver halide color photographic light-sensitive material containing a 1-naphthol type cyan coupler which causes less reduction in density even when processed in a fatigue bleaching solution. A third object is to provide a silver halide color photographic light-sensitive material containing a 1-naphthol type cyan coupler in which the secondary absorption in the blue part is reduced. Fourth
An object of the present invention is to provide a silver halide color photographic light-sensitive material containing a 1-naphthol type cyan coupler having an improved color forming property. A fifth object is to provide a silver halide color photographic light-sensitive material containing a 1-naphthol type cyan coupler which is easy to synthesize and inexpensive to produce.

[0007]

The object of the present invention is achieved by a silver halide color photographic light-sensitive material containing a cyan coupler represented by the following general formula (1) or (2). .

[0008]

[Chemical 3]

In the formula, R ₁ and R ₂ each represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group, and R ₃ represents an aliphatic group, an aromatic group, a heterocyclic group or an amino group. X represents a hydrogen atom or a leaving group when coupled with an oxide of a color developing agent.

[0010]

[Chemical 4]

In the formula, R ₁ and R ₂ each represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group, and R ₄ represents NR ₅ (R ₆ ), OR ₇
Represents R ₅ and R ₆ each represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group, and R ₇ represents an aliphatic group, an aromatic group or a heterocyclic group. X represents a hydrogen atom or a leaving group when coupled with an oxide of a color developing agent. In the general formula (1) or (2), R ₁ , R ₂ , R ₃
Further, when either R ₄ is a diffusion preventing group or when R ₁ is a hydrogen atom, a more remarkable effect is exhibited.

The cyan couplers represented by the general formulas (1) and (2) will be described in detail below.

R ₁ and R _{2 in the} general formulas (1) and (2)
Each represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group, and the aliphatic group represented by R ₁ and R ₂ represents a linear, branched or cyclic alkyl group, alkenyl group or alkynyl group. Further, it may have a substituent.

The aromatic group represented by R ₁ and R ₂ is
It represents a phenyl group which may have a substituent or a naphthyl group.

Specific examples of the aliphatic group represented by R ₁ and R ₂ include methyl group, ethyl group, n-propyl group, i-propyl group, n-octyl group, n-decyl group, n- Undecyl group,
n-dodecyl group, n-tridecyl group, n-pentadecyl group, n-
Hexadecyl group, n-octadecyl group, cyclohexyl group, trifluoromethyl group, dodecyloxypropyl group, 2,4-di-tert-amylphenoxypropyl group, 2,4-di
Examples thereof include -tert-amylphenoxybutyl group and p-tret-octylphenoxypropyl group.

Specific examples of the aromatic group represented by R ₁ and R ₂ include p-tetradecyloxyphenyl group, o-tetradecyloxyphenyl group, o-iso-hexadecyloxyphenyl group, p -Dodecylphenyl group, naphthyl group and the like.

Further, examples of the heterocyclic group represented by R ₁ and R ₂ include 2-pyridyl group, 4-pyridyl group, quinolyl group,
Examples include 2-furyl group.

Next, R _{3 in the} general formula (1) will be described. R ₃ represents an aliphatic group, an aromatic group, a heterocyclic group or an amino group. The aliphatic group represented by R ₃ is linear, branched,
Alternatively, it represents a cyclic alkyl group, alkenyl group, or alkynyl group, and may have a substituent. The aromatic group represented by R ₃ represents a phenyl group which may have a substituent or a naphthyl group. The amino group represented by R ₃ represents an amino group, an alkylamino group, a dialkylamino group, or an anilino group which may have a substituent.

Specific examples of the aliphatic represented by R ₃ include methyl group, ethyl group, n-propyl group, i-propyl group,
n-butyl group, t-butyl group, n-octyl group, n-nonyl group,
n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-pentadecyl group, n-hexadecyl group, n-octadecyl group, cyclohexyl group, trifluoromethyl group, dodecyloxypropyl group, methoxymethyl Group, phenoxymethyl group, 2,4-di-tert-amylphenoxypropyl group and the like.

Specific examples of the aromatic group represented by R ₃ include phenyl group, p-chlorophenyl group, m-methanesulfonamidophenyl group, p-butyloxyphenyl group and p-tetradecyloxyphenyl group. , Naphthyl group and the like.

Examples of the heterocyclic group represented by R ₃ include 3-pyridyl group and 2-furyl group.

Specific examples of the amino group represented by R ₃ include amino group, methylamino group, ethylamino group, butylamino group, cyclohexylamino group, N, N-dimethylamino group and benzylamino group. , Anilino group, p-chloroanilino group, p-methylanilino group and the like.

Next, R ₅ , R ₆ and R _{7 in the} general formula (2) will be described. The aliphatic group represented by R ₅ , R ₆ , and R ₇ represents a linear, branched, or cyclic alkyl group, alkenyl group, or alkynyl group, and may have a substituent. The aromatic group represented by R ₅ , R ₆ and R ₇ represents a phenyl group which may have a substituent or a naphthyl group.

Specific examples of the aliphatic group, aromatic group and heterocyclic group represented by R ₅ , R ₆ and R ₇ have been explained for R ₃ .
Specific examples of the aliphatic group, aromatic group and heterocyclic group can be given.

Next, X in the general formulas (1) and (2) will be described. X represents a hydrogen atom or a leaving group when coupled with an oxide of a color developing agent.

As the coupling-off group, a halogen atom (eg, fluorine atom, chlorine atom, bromine atom, iodine atom), aliphatic oxy group (eg, methoxy group, ethoxy group, octyloxy group, carboxymethyloxy group, methoxycarbonyl) Methyloxy group, pentyloxycarbonylmethyl group, 2-carboxymethylthioethoxy, 2-
Methoxyethylcarbamoylmethyloxy group, 2-phenoxyethoxy group, etc.), aromatic oxy group (for example, 4-methoxyphenoxy group, 4-chlorophenoxy group, 4-tert-butylphenoxy group, 4-tert-octylphenoxy group, 4 -(3-
(Carboxypropanoylamino) phenoxy group, etc.), heterocyclic oxy group (eg 4-pyridyloxy, 1-phenyl
-5-tetrazolyloxy group, etc.), aliphatic thio group (dodecylthio group, carboxyethylthio group, etc.), aromatic thio group (4-dodecylphenylthio group, etc.), heterocyclic thio group (1-phenyltetrazole- 5-ylthio group etc.) Acyloxy group (eg acetoxy group, benzoyloxy group etc.), Sulfonamide group (eg methanesulfonamide group, benzenesulfonamide group etc.) Aromatic azo group (eg phenylazo group, 4-methoxyazo etc.) Is mentioned.

Specific examples of the cyan couplers represented by the general formulas (1) and (2) of the present invention will be described below.

[0028]

[Chemical 5]

[0029]

[Chemical 6]

[0030]

[Chemical 7]

[0031]

[Chemical 8]

[0032]

[Chemical 9]

[0033]

[Chemical 10]

[0034]

[Chemical 11]

The synthesis examples of the cyan couplers represented by the general formulas (1) and (2) of the present invention will be described below.

Synthesis Example 1 (Synthesis of Exemplified Compound 1-1)

[0037]

[Chemical 12]

Compound 1 (24.5 g) was dispersed in xylene (300 ml), phosphorus pentasulfide (22.2 g) was added thereto, and the mixture was reacted at 70 ° C. for 3 hours. After adding 300 ml of ethyl acetate to the reaction solution, the organic layer was washed with water and dried, and then the solvent was distilled off to obtain a residue. The residue was purified by chromatography on silica gel and crystallized from acetonitrile to obtain 8 g of compound 2.

Next, compound 2, 5.2 g, compound 3, 6.1 g
Was dissolved in 30 ml of dimethylformamide, heated to 60 ° C, and then dicyclohexylcarbodiimide (DCC) was added thereto.
5.5 g of dimethylformamide solution was added dropwise. After heating for 3 hours, the mixture was cooled with ice, the precipitated solid was removed by filtration, the filtrate was poured into 200 ml of water, and the mixture was extracted with ethyl acetate.
The organic layer was washed with water and dried, and then the solvent was distilled off to obtain a residue. The residue was purified by column chromatography to obtain 6.2 g of Exemplified Compound 1-1.

Synthesis Example 2 (Synthesis of Exemplified Compound 1-15)

[0041]

[Chemical 13]

Compound 4, 10.2 g was added to dimethylacetamide
Disperse in 50 ml and add ethyl isothiocyanate 4.8
g was added dropwise. After the dropping, the mixture was reacted at 40 ° C for 2 hours. The reaction mixture was poured into 300 ml of water and extracted with ethyl acetate. The organic layer was washed with water and dried, and then the solvent was distilled off to obtain a residue. The residue was recrystallized from ethyl acetate / hexane to obtain 11.2 g of compound 5. Compound 5, 5.4 g was condensed with amine compound 3 in the same manner as in Synthesis Example 1 to give Exemplified Compound 1-1.
5, 6.2 g were obtained.

Synthesis Example 3 (Synthesis of Exemplified Compound 2-2)

[0044]

[Chemical 14]

Compound 4, 10.2 g was added to dimethylacetamide
It was dispersed in 50 ml and 6.8 g of oxalic acid chloride monoethyl ester was added dropwise thereto. After dropping, the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into 300 ml of water and extracted with ethyl acetate. The organic layer was washed with water and dried, and then the solvent was distilled off to obtain a residue. The residue was purified by chromatography to obtain Compound 6 (9.1 g). Compound 6 (5.0 g) was condensed with amine compound 3 in the same manner as in Synthesis Example 1 to obtain Exemplified Compound 2-2 (8.4 g).

The cyan coupler represented by formula (1) or (2) of the present invention is usually 0.002 to 1 mol, preferably 0.005 to 1 mol per mol of silver halide in the silver halide emulsion constituting the photosensitive layer. Contains 0.3 mol.

In the present invention, the cyan coupler represented by the general formula (1) or (2) is contained in at least one of the red-sensitive silver halide emulsion layers.

In order to incorporate the cyan coupler of the present invention into a silver halide emulsion layer, a conventionally known method such as a high boiling point solvent such as known dibutyl phthalate, tricresyl phosphate and butyl acetate, ethyl acetate and the like can be used. After dissolving the cyan coupler of the present invention in a mixed solution of low boiling point solvents such as those described above or in a solvent containing only low boiling point solvents, it is mixed with an aqueous gelatin solution containing a surfactant, and then a high speed rotary mixer or colloid mill or ultrasonic dispersion. After emulsifying and dispersing using a machine, a method of directly adding to the emulsion can be adopted. Further, after the above emulsified dispersion is set, it may be shredded, washed with water, and then added to the emulsion.

As the silver halide emulsion used in the light-sensitive material of the present invention, any ordinary silver halide emulsion can be used. The emulsion can be chemically sensitized by a conventional method, and can be optically sensitized to a desired wavelength region by using a sensitizing dye.

Antifoggants, stabilizers and the like can be added to the silver halide emulsion. It is advantageous to use gelatin as the binder of the emulsion.

The emulsion layer and other hydrophilic colloid layers may be hardened, and may contain a plasticizer and a dispersion (latex) of a water-insoluble or sparingly soluble synthetic polymer. A coupler is used in the emulsion layer of the color photographic light-sensitive material.

Further, by coupling with colored couplers, competing couplers and oxidized products of developing agents, which have the effect of color correction, development accelerators, bleaching accelerators, developers, silver halide solvents, toning agents, hardeners and hardeners Compounds that release photographically useful fragments such as film agents, antifoggants, antifoggants, chemical sensitizers, spectral sensitizers, and desensitizers can be used.

The light-sensitive material may be provided with auxiliary layers such as a filter layer, an antihalation layer and an anti-irradiation layer. In these layers and / or emulsion layers,
Dyes may be included which are bleached or bleached from the light-sensitive material during the development process. For the light-sensitive material, formalin scavenger, fluorescent whitening agent, matting agent, lubricant, image stabilizer, surfactant, color antifoggant, development accelerator,
Development retarders and bleaching accelerators can be added.

As the support, paper laminated with polyethylene or the like, polyethylene terephthalate film, baryta paper, cellulose triacetate or the like can be used.

In order to obtain a dye image using the light-sensitive material of the present invention, a commonly known color photographic process can be carried out after exposure.

[0056]

EXAMPLES Specific examples of the present invention will be described below, but the embodiments of the present invention are not limited to these.

In all the following examples, the addition amount in the silver halide photographic light-sensitive material is the number of grams per 1 m ² unless otherwise specified. Also, silver halide and colloidal silver are shown in terms of silver.

Example 1 A multi-layer color photographic light-sensitive material (Sample 1) was prepared by sequentially forming each layer having the composition shown below from the support side on a triacetyl cellulose film support.

First layer: antihalation layer (HC-1) Black colloidal silver 0.20 UV absorber (UV-1) 0.20 Colored coupler (CC-1) 0.05 Colored coupler (CM-1) 0.05 High boiling point solvent (Oil-) 1) 0.20 gelatin 1.5 second layer; intermediate layer (IL-1) UV absorber (UV-1) 0.01 high boiling solvent (Oil-1) 0.01 gelatin 1.5 third layer; low sensitivity red-sensitive emulsion layer (RL) iodine Silver bromide emulsion (Em-1) 0.8 Silver iodobromide emulsion (Em-2) 0.8 Sensitizing dye (SD-1) 2.5 × 10 ^-4 (mol / silver 1 mol) Sensitizing dye (SD-2) 2.5 × 10 ^-4 (mol / silver 1 mol) Sensitizing dye (SD-3) 0.5 × 10 ^-4 (mol / silver 1 mol) Cyan coupler (CA) 1.0 Colored cyan coupler (CC-1) 0.05 DIR compound (D-1) 0.002 High boiling point solvent (Oil-1) 0.5 Gelatin 1.5 Fourth layer; High-sensitivity red-sensitive emulsion Layer (RH) Silver iodobromide emulsion (Em-3) 2.0 Sensitizing dye (SD-1) 2.0 × 10 ⁻⁴ (mol / silver 1 mol) Sensitizing dye (SD-2) 2.0 × 10 ⁻⁴ (mol) / Silver 1 mol) Sensitizing dye (SD-3) 0.1 × 10 ^-4 (mol / silver 1 mol) Cyan coupler (CA) 0.25 Cyan coupler (CB) 0.05 Colored cyan coupler (CC-1) 0.015 DIR compound (D-1) 0.05 High boiling point solvent (Oil-1) 0.2 Gelatin 1.5 Fifth layer; Intermediate layer (IL-2) Gelatin 0.5 Sixth layer; Low sensitivity green sensitive emulsion layer (GL) Silver iodobromide emulsion (Em-1) 1.3 Sensitizing dye (SD-4) 5 × 10 ^-4 (mol / silver 1 mol) Sensitizing dye (SD-5) 1 × 10 ^-4 (mol / silver 1 mol) Magenta coupler (M -1) 0.25 Magenta coupler (M-2) 0.25 Colored magenta coupler (CM-1) 0.01 DIR compound (D-3) 0.02 DIR compound (D-4) 0 .020 High boiling point solvent (Oil-2) 0.3 Gelatin 1.0 7th layer; High-sensitivity green-sensitive emulsion layer (GH) Silver iodobromide emulsion (Em-3) 1.3 Sensitizing dye (SD-6) 1.5 × 10 ^-4 (Mol / silver 1 mol) Sensitizing dye (SD-7) 2.5 × 10 ⁻⁴ (mol / silver 1 mol) Sensitizing dye (SD-8) 0.5 × 10 ⁻⁴ (mol / silver 1 mol) Magenta coupler ( M-1) 0.05 Magenta coupler (M-2) 0.10 Colored magenta coupler (CM-2) 0.05 DIR compound (D-3) 0.01 High boiling point solvent (Oil-2) 0.2 Gelatin 1.0 Eighth layer; Yellow filter layer (YC) ) Yellow colloidal silver 0.1 Color stain inhibitor (SC-1) 0.1 High boiling point solvent (Oil-3) 0.1 Gelatin 0.8 9th layer; Low sensitivity blue sensitive emulsion layer (BL) Silver iodobromide emulsion (Em-1) 0.25 Silver iodobromide emulsion (Em-2) 0.25 Sensitizing dye (SD-10) 7 × 10 ^-4 (mol / silver 1 mol) Yellow cap (Y-1) 0.5 Yellow coupler (Y-2) 0.1 DIR compound (D-2) 0.01 High boiling solvent (Oil-2) 0.3 Gelatin 1.0 10th layer; High-sensitivity blue-sensitive emulsion layer (BH) Iodobromide Silver emulsion (Em-4) 0.4 Silver iodobromide emulsion (Em-1) 0.4 Sensitizing dye (SD-9) 1 × 10 ⁻⁴ (mol / silver 1 mol) Sensitizing dye (SD-10) 3 × 10 ^-4 (mol / silver 1 mol) Yellow coupler (Y-1) 0.30 Yellow coupler (Y-2) 0.05 High boiling point solvent (Oil-2) 0.15 Gelatin 1.1 11th layer; 1st protective layer (PRO-1) Fine particles Silver iodobromide emulsion (average grain size 0.08 μm, AgI content 2 mol%) 0.4 UV absorber (UV-1) 0.10 UV absorber (UV-2) 0.05 High boiling point solvent (Oil-1) 0.1 High boiling point solvent (Oil-3) 0.1 Formalin Scavenger (HS-1) 0.5 Formalin Scavenger (HS-2) 0.2 Gelatin 1.0 12th layer; 2nd protective layer (PRO-2) Surfactant (Su-1) 0.005 Alkali-soluble matting agent (average particle size 2 μm) 0.05 Polymethylmethacrylate (average particle size 3 μm) 0.05 Sliding agent (WAX- 1) 0.04 gelatin 0.6 In addition to the above composition, coating aid Su-2, dispersion aid Su-3, film hardeners H-1 and H-2, stabilizer ST-for each layer.
1, antifoggants AF-1 and AF-2 were added.

Em-1 Average grain size 0.46 μm Average silver iodide content: 7.0 mol%, monodisperse (width of distribution: 14%) surface low silver iodide (2 mol%) containing core / shell type emulsion Em-2 Average grain size 0.30 μm Average silver iodide content: 2.0 mol%, monodisperse (14% distribution) surface silver bromide-containing core / shell emulsion Em-3 Average grain size 0.81 μm Average Silver iodide content: 7.0 mol%, monodisperse (width of distribution: 14%) surface low silver iodide (1.
0 mol%)-containing core / shell type emulsion Em-4 average grain size 0.95 μm average silver iodide content: 8.0 mol%, monodisperse (width of distribution: 14%) surface low silver iodide (0.
5 mol%)-containing core / shell type emulsion The breadth of distribution is represented by the following formula.

Range of distribution = (standard deviation value / average particle size) × 100

[0062]

[Chemical 15]

[0063]

[Chemical 16]

[0064]

[Chemical 17]

[0065]

[Chemical 18]

[0066]

[Chemical 19]

[0067]

[Chemical 20]

[0068]

[Chemical 21]

[0069]

[Chemical formula 22]

Next, in the above sample 1, the third layer and the fourth layer
Cyan coupler C- added to the silver halide emulsion layer of the layer
Comparative coupler RC-, equimolar in place of A and CB
Samples 2 to 40 were prepared by adding 1, RC-2, RC-3 and the cyan coupler of the present invention as shown in Tables 1 and 2.

Each of the sample Nos. 1 to 40 produced in this way
Wedge exposure of 1/100 second with red light,
The following developing processes A and B were performed.

Processing step (38 ° C.) Color development 3 minutes 15 seconds Bleach 6 minutes 30 seconds Water washing 3 minutes 15 seconds Settling 6 minutes 30 seconds Water washing 3 minutes 15 seconds Stabilization 1 minute 30 seconds Drying Each processing step The composition of the treatment liquid used in is as follows. However, in the development treatment A, the treatment solution in the bleaching step is the bleaching solution A below, and in the development treatment B, the treatment solution in the bleaching step is the bleaching solution B below.

<Color developer> 4-amino-3-methyl-N-ethyl-N- (β-hydroxyethyl) aniline / sulfate 4.75 g anhydrous sodium sulfite 4.25 g hydroxylamine / 1/2 sulfate 2.0 g anhydrous Potassium carbonate 37.5 g Potassium bromide 1.3 g Nitrilotriacetic acid trisodium salt (monohydrate) 2.5 g Potassium hydroxide 1.0 g Water is added to make 1 liter. (PH = 10.2) <Bleach A> Ethylenediaminetetraacetic acid iron (III) ammonium salt 100g Ethylenediaminetetraacetic acid diammonium salt 10.0g Ammonium bromide 150.0g Glacial acetic acid 10ml Add water to make 1 liter and use ammonia water to adjust the pH. Adjust to = 6.0.

<Bleaching Solution B> The same composition as Bleaching Solution A except that 2.5 g of sodium hydrosulfite was added to Bleaching Solution A above per liter.

<Fixer> Ammonium thiosulfate 175.0 g Anhydrous sodium sulfite 8.5 g Sodium metasulfite 2.3 g Water is added to make 1 liter, and pH is adjusted to 6.0 using acetic acid.

<Stabilizer> Formalin (37% aqueous solution) 1.5 ml Conidax (manufactured by Konica Corporation) 7.5 ml Water is added to make 1 liter.

The obtained samples 1 to 40 were processed in accordance with the color development processing and development step, and the resulting dye image was irradiated with red light and blue light using an optical densitometer (PDA-65 type manufactured by Konica Corporation). The concentration was measured. The development process B is a model of a fatigue bleaching solution.

The sensitivity is the density measured with red light,
It means the reciprocal of the exposure amount required to give the minimum density +0.1, and it was expressed as a relative value with 100 when the sample 1 was subjected to the development treatment A.

The density change is a value obtained by multiplying the ratio of the maximum density of development processing A to the maximum density of development processing A by 100 with respect to the density measured with red light.

B absorption means that the concentration measured with red light is 1.
It is the density measured with blue light when it becomes 5, and is expressed as a relative value when Sample 1 is 100. (Use of Sample of Development Treatment A) Heat resistance is a rate of change in concentration after the sample treated by Development Treatment A is stored at 40 ° C. and 80% (relative humidity) for 6 days.
It was expressed as a relative value with sample 1 being 100.

The light resistance is a rate of change in density after irradiation of a sample processed by the development treatment A with a xenon fade meter of 70,000 lux for 3 days, and is represented by a relative value with sample 1 being 100.

[0082]

[Table 1]

[0083]

[Table 2]

As is clear from Tables 1 and 2, the samples containing the cyan coupler of the present invention have high sensitivity and little change in density when a fatigue bleaching solution is used.

Further, regarding the generated cyan image,
It can be seen that the absorption of the blue part, which is not preferable in color reproduction, is improved as compared with the samples 2 and 3 using the comparative coupler, and the color image fastness is also excellent.

[0086]

EFFECTS OF THE INVENTION According to the present invention, a color image is excellent in heat and light fastness, the density is less decreased even when treated in a fatigue bleaching solution, the secondary absorption in the blue part is reduced, and the color developability is improved.
A silver halide color photographic light-sensitive material containing a 1-naphthol cyan coupler was obtained. Further, a silver halide color photographic light-sensitive material containing a 1-naphthol type cyan coupler which is easy to synthesize and low in manufacturing cost was obtained.

Claims (4)

[Claims] 1. A silver halide color photographic light-sensitive material containing a cyan coupler represented by the following general formula (1). [Chemical 1] In the formula, R ₁ and R ₂ are each a hydrogen atom, an aliphatic group, an aromatic group,
It represents a heterocyclic group, and R ₃ represents an aliphatic group, an aromatic group, a heterocyclic group, or an amino group. X represents a hydrogen atom or a leaving group when coupled with an oxide of a color developing agent. 2. A silver halide color photographic light-sensitive material containing a cyan coupler represented by the following general formula (2). [Chemical 2] In the formula, R ₁ and R ₂ are each a hydrogen atom, an aliphatic group, an aromatic group,
Represents a heterocyclic group, R ₄ represents NR ₅ (R ₆ ), OR ₇ . R ₅ , R
₆ represents a hydrogen atom, an aliphatic group, an aromatic group, and a heterocyclic group, and R ₇ represents an aliphatic group, an aromatic group, and a heterocyclic group.
X represents a hydrogen atom or a leaving group when coupled with an oxide of a color developing agent. 3. The general formula (1) or (2), wherein any one of R ₁ , R ₂ , R _{3 and} R ₄ is a diffusion preventing group. Silver halide color photographic light-sensitive material. 4. In the general formula (1) or (2), R ₁ is a hydrogen atom.
2. A silver halide color photographic light-sensitive material as described in 2 or 3.