JP3240547B2 - Silver halide color photographic materials - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a silver halide color photographic light-sensitive material, and more particularly to a silver halide color photographic material having high sensitivity, high color development, excellent color reproducibility, and low dependence of the spectral absorption wavelength of the color dye on the concentration. The present invention relates to a color photographic light-sensitive material.

[0002]

2. Description of the Related Art At present, a color reduction method is used for a silver halide color photographic light-sensitive material (hereinafter also simply referred to as a light-sensitive material), and a combination of three dyes derived from a yellow coupler, a magenta coupler and a cyan coupler. Thus, a color image is formed.

As magenta couplers used in conventional silver halide color photographic light-sensitive materials, pyrazolone, pyrazolinobenzimidazole or indanone type couplers are known, and among them, various 5-pyrazolone derivatives are widely used. ing.

Examples of the substituent at the 3-position of the 5-pyrazolone ring of the 5-pyrazolone derivative include an alkyl group, an aryl group, an alkoxy group described in US Pat. No. 2,439,098, and US Pat. No. 2,369,489. 2nd, 60th
No. 0,788, acylamino group,
Ureido groups described in 3,558,319 are used. However, the above couplers have low coupling activity with the oxidation product of the developing agent, so that a high-density magenta dye image cannot be obtained, and the secondary absorption in the blue light region of the magenta dye image obtained by color development is large. In addition, there are disadvantages such as poor cutting of the long wavelength side of the main absorption.

Also, US Pat. No. 2,311,081 and US Pat.
No. 3,677,764, No. 3,684,514, British Patent No. 956,261, No. 1,173,513
The 3-anilino-5-pyrazolone-based coupler has advantages such as high coupling activity and high color development, and small unnecessary absorption in a red light region.
The anilino-5-pyrazolone coupler has a relatively short main absorption and deteriorates print reproducibility when used in a color negative silver halide photographic material.

Various studies have been made for the purpose of improving the disadvantage that the main absorption is a short wave, and a 1-pentahalogenophenyl-3-anilino-5-pyrazolone-based coupler has been proposed in JP-A-52-80027. I have. The coloring dye derived from the coupler has a spectral absorption maximum wavelength which is preferable as a magenta coupler for color negative, and is superior to the conventional coupler in this point. However, these couplers have the drawback that the coloring properties are still insufficient, and that the spectral absorption maximum wavelength of the coloring dye has a concentration dependency.

[0007]

SUMMARY OF THE INVENTION A first object of the present invention is to provide a silver halide color photograph having high sensitivity, high color development, excellent color reproducibility, and a small dependence of the colorant on the concentration of the spectral absorption maximum wavelength. Provided is a photosensitive material.

A second object of the present invention is to provide a silver halide color photographic light-sensitive material which is thin and has excellent sharpness.

[0009]

The above object of the present invention is achieved by the following constitution.

(1) A silver halide color photographic light-sensitive material having a photographic component layer comprising a blue-sensitive silver halide emulsion layer, a green-sensitive silver halide emulsion layer and a red-sensitive silver halide emulsion layer on a support, A silver halide color photographic light-sensitive material characterized in that at least one of the silver halide emulsion layers contains at least one kind of coupler represented by the following general formula [I].

[0011]

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In the formula, R ₁ represents a hydrogen atom or a group which is eliminated by reacting with an oxidized form of a developing agent, and R ₂ represents a chlorine atom or an alkoxy group. R ₃ represents a substituent, and n represents 1 to 5
Represents an integer. R ₄ , R ₅ , R ₆ , R ₇ and R ₈ represent a halogen atom.

(2) The silver halide color photographic material as described in (1), wherein in the general formula [I], R ₁ is an arylthio group.

(3) The silver halide color photographic material as described in (2), wherein at least one R ₃ in the general formula [I] is substituted ortho to NHCO.

(4) In the general formula [I], R ₄ ,
The silver halide color photographic material as described in (2), wherein R ₅ , R ₆ , R ₇ and R ₈ are all chlorine atoms.

(5) The silver halide color photographic material as described in (2), wherein R ₁ in the general formula [I] is a group represented by the following general formula [II].

[0017]

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In the formula, R ₂₁ represents a substituent.

Hereinafter, the present invention will be described specifically.

The coupler of the present invention represented by the general formula [I] (hereinafter also referred to as a magenta coupler represented by the general formula [I]) will be described.

In the general formula [I], R ₁ is a hydrogen atom or a group which is eliminated by reacting with an oxidized form of the developing agent. An example of the group which is eliminated by reacting with the oxidized form of the developing agent is phenylthio. And a carboxypropylthio group, an octylthio group and the like, and a phenylthio group is preferred from the viewpoint of color development. The phenylthio group preferably has an acylamino group at the ortho position of the sulfur atom from the viewpoint of color development.

R ₂ represents a chlorine atom or an alkoxy group. Examples of the alkoxy group include a methoxy group, an ethoxy group, an isopropyloxy group, a t-butyloxy group, a hexyloxy group and a methoxyethyloxy group.

R ₃ represents a substituent, irrespective of its type,
Examples of R ₃ include an alkyl group such as a methyl group, an isopropyl group and a trifluoromethyl group, an alkoxy group such as a methoxy group and an ethoxy group, an aryloxy group such as a phenoxy group and a tolyloxy group, a fluorine atom and a chlorine atom. And a halogen atom such as a bromine atom, an alkylamino group such as a nitro group, an amino group and a dimethylamino group.

It is preferable to substitute at least one R ₃ at the ortho position of NHCO in order to reduce the concentration dependence of the spectral absorption maximum wavelength of the coloring dye. n represents an arbitrary integer of 1 to 5. R ₄ , R ₅ , R ₆ , R ₇ and R ₈ represent a halogen atom, such as a fluorine atom, a chlorine atom, and a bromine atom. R ₄ , R ₅ , R ₆ , R _7, and R ₈ are preferably chlorine atoms in that the spectral absorption maximum wavelength of the coloring dye becomes a desired wavelength and the raw materials can be obtained at relatively low cost.

R ₂₁ represents a substituent. Examples of the substituent include an alkyl group such as a methyl group, an ethyl group and a methoxyethyl group, an aryl group such as a phenyl group and a 4-methoxyphenyl group, and a 2-pyridyl group and the like. A heterocyclic group may be mentioned, and a branched alkyl group or an alkyl group having a substituent is preferable from the viewpoint of good solubility and good color development. The most preferred example is 1-
(2,4-di-tert-amylphenoxy) propyl group.

Next, typical specific examples of the magenta coupler represented by the general formula [I] of the present invention will be shown, 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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Next, specific synthesis examples of the magenta coupler represented by the general formula [I] of the present invention will be described. General synthesis methods, for example, US Pat. Nos. 2,369,489 and 2,376,380
No. 2,472,581, No. 2,600,788, No. 2,933,39
No. 1, No. 3,615,506, UK Patent No. 956,261, No. 1,1
The compound can be synthesized by referring to the synthesis methods described in JP-A-34,329, JP-B-45-20636, JP-A-2-39148 and the like.

Specific examples of the synthesis of the magenta coupler represented by the general formula [I] are shown below.

Synthesis Example 1 Synthesis of Exemplified Compound 3

[0036]

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To 19.10 g of 2,6-dichlorobenzoic acid is added 60 ml of thionyl chloride, and the mixture is heated at 60 to 65 ° C. for 1.5 hours. Thionyl chloride is distilled off under reduced pressure to obtain a pale yellow oil (Compound 2).

To 35.47 g of Compound 1, 150 ml of ethyl acetate and water
75 ml and 12.30 g of anhydrous sodium acetate are added, and the whole amount of compound 2 is added while stirring at room temperature. After stirring for 4 hours, the precipitate is collected by filtration, washed successively with 100 ml of water, 50 ml of methanol and 50 ml of ethyl acetate, and dried. Compound 3 pale brown powder
32.7 g (67%) are obtained.

The structure of Compound 3 was confirmed by NMR spectrum and mass spectrum. The mp was 300 ° C or higher.

[0040]

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225 ml of DMF and 27.22 g of compound 4 were added to 37.47 g of compound 3, and 4.63 g of bromine was added at 45 to 80 ° C. in 45 ml of DMF.
Add the solution dissolved in l. Heat at 80-90 ° C for 3.3 hours,
After cooling, add ethyl acetate and wash with water. The solvent is distilled off, and recrystallization from a mixed solvent of toluene and hexane gives crude light brown crystals. This was recrystallized from a mixed solvent of ethyl acetate-acetonitrile to give milky white crystals of Exemplified Compound 3.
37.70 g are obtained.

The structure of Exemplified Compound 3 is represented by mass spectrum, N
Confirmed by MR spectrum. mp 205 ° C.

The physical properties of the exemplified compounds synthesized in the same manner as described above are shown below.

[0044] The magenta coupler represented by the general formula (I) of the present invention is
Usually 1 × 10 ^-3 mol to 8 × 10 ^-1 mo per mol of silver halide
l, preferably in the range of 1 × 10 ^-2 mol to 8 × 10 ^-1 mol.

The magenta coupler of the present invention represented by the general formula [I] can be used in combination with another type of magenta coupler.

In order to incorporate the magenta coupler represented by the general formula [I] of the present invention, a conventional method, for example, using a known high-boiling solvent such as dibutyl phthalate or tricresyl phosphate with butyl acetate or ethyl acetate can be used. After dissolving the magenta coupler represented by the general formula [I] alone or in combination in a mixture of low-boiling solvents or a solvent having only a low-boiling solvent, such as a solution of gelatin with a surfactant, After mixing and then emulsifying and dispersing using a high-speed rotary mixer, a colloid mill or an ultrasonic dispersing machine, a method of directly adding to the emulsion can be adopted. Alternatively, the emulsified dispersion may be set, then cut into pieces, washed with water, and then added to the emulsion.

The magenta coupler of the present invention represented by the general formula [I] may be separately dispersed in a high-boiling solvent and the above-mentioned dispersion method and added to a silver halide emulsion.
A method in which both compounds are simultaneously dissolved, dispersed and added to the emulsion is preferred.

The amount of the high boiling point solvent to be added is preferably 0.01 to 10 g, more preferably 0.1 to 3.0 g, based on 1 g of the magenta coupler represented by the general formula [I] of the present invention. Instead of using a high boiling point solvent, it may be dissolved in only a low boiling point solvent, dispersed, and added to the emulsion.

As the silver halide emulsion used in the light-sensitive material of the present invention, any conventional 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.

An antifoggant, a stabilizer and the like can be added to the silver halide emulsion. It is advantageous to use gelatin as a binder for the emulsion.

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

Further, a development accelerator, a bleaching accelerator, a developer, a silver halide solvent, a toning agent, and a coupling reaction with a colored coupler, a competing coupler, and an oxidized form of a developing agent having a color correcting effect. Compounds that release photographically useful fragments such as hardeners, foggants, antifoggants, chemical sensitizers, spectral sensitizers and desensitizers can be used.

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, generally known color photographic processing can be performed after exposure.

[0055]

EXAMPLES The present invention will now be described with reference to specific examples, but the embodiments of the present invention are not limited thereto.

Example 1 In the following, the amount of addition in the silver halide photographic light-sensitive material indicates the number of grams per 1 m ² unless otherwise specified. In addition,
Silver halide and colloidal silver were shown in terms of silver, and sensitizing dyes were shown in moles per mole of silver.

One side (front side) of the triacetylcellulose film support is subjected to a subbing process, and then the support is sandwiched between the triacetylcellulose film support and a surface opposite to the subscribed surface (back surface).
Then, a layer of the following composition was sequentially applied from the support side to prepare a support which was subjected to an undercoating process. The amount of addition is shown per 1 m ² .

Back first layer Alumina sol AS-100 (aluminum oxide) (manufactured by Nissan Chemical Industries, Ltd.) 0.1 g Diacetyl cellulose 0.2 g Back second layer Diacetyl cellulose 100 mg Stearic acid 10 mg Silica fine particles (average particle size 0.2 μm) 50
Each layer having the following composition was sequentially formed on the surface of a triacetylcellulose film support having been subjected to subbing processing from the support side to prepare a multilayer color photographic light-sensitive material 1.

First layer: Antihalation layer (HC) Black colloidal silver 0.1
5 UV absorber (UV-1) 0.20 Compound (CC-1) 0.02 High boiling solvent (Oil-1) 0.20 High boiling solvent (Oil-2) 0.20 Gelatin 1.6 Second layer; Intermediate layer (IL-1) Gelatin 1.3 Third layer; low-sensitivity red-sensitive emulsion layer (RL) Silver iodobromide emulsion (average grain size: 0.3 μm) (average iodine content: 2.0 mol%) 0.4 Silver iodobromide emulsion (average grain size: 0.4 μm) ( Average iodine content 8.0 mol%) 0.3 sensitizing dye (S-1) 3.2 × 10 ^-4 sensitizing dye (S-2) 3.2 × 10 ^-4 sensitizing dye (S-3) 0.2 × 10 ^-4 cyan coupler (C-1) 0.50 Cyan coupler (C-2) 0.13 Colored cyan coupler (CC-1) 0.07 DIR compound (D-1) 0.006 DIR compound (D-2) 0.01 High boiling solvent (Oil-1) 0.55 Gelatin 1.0 Fourth layer: high-sensitivity red-sensitive emulsion layer (R-H) silver iodobromide emulsion (average grain size 0.7 μm) (average iodine content 7.5 mol%) 0.9 sensitization Containing (S-1) 1.7 × 10 -4 Sensitizing dye (S-2) 1.6 × 10 -4 Sensitizing dye (S-3) 0.1 × 10 -4 Cyan coupler (C-2) 0.23 Colored cyan coupler (CC -1) 0.03 DIR compound (D-2) 0.02 High boiling solvent (Oil-1) 0.25 Gelatin 1.0 Fifth layer; Intermediate layer (IL-2) Gelatin 0.8 Sixth layer; Low sensitivity green-sensitive emulsion layer (GL ) Silver iodobromide emulsion (average particle size 0.4 μm) (average iodine content 8.0 mol%) 0.6 Silver iodobromide (average particle size 0.3 μm) (average iodine content 2.0 mol%) 0.2 sensitizing dye (S- 4) 6.7 × 10 ^-4 sensitizing dye (S-5) 0.8 × 10 ^-4 magenta coupler (Ma) 0.35 Colored magenta coupler (CM-1) 0.05 DIR compound (D-3) 0.02 Additive 1 0.10 High Boiling point solvent (Oil-2) 0.7 Gelatin 1.0 7th layer; High-sensitivity green-sensitive emulsion layer (GH) Silver iodobromide emulsion (average particle size 0.7 μm) (containing average iodine 7.5 mol%) 0.9 Sensitizing dye (S-6) 1.1 × 10
^-4 sensitizing dye (S-7) 2.0 × 10 ^-4 sensitizing dye (S-8) 0.3 × 10 ^-4 magenta coupler (Ma) 0.20 Colored magenta coupler (CM-1) 0.02 DIR compound (D- 3) 0.004 High boiling solvent (Oil-2) 0.35 Additive 1 0.07 Gelatin 1.0 8th layer; Yellow filter layer (YC) Yellow colloidal silver 0.1 Additive (SC-1) 0.12 High boiling solvent (Oil-2) 0.15 Gelatin 1.0 Ninth layer; low-sensitivity blue-sensitive emulsion layer (BL) Silver iodobromide emulsion (average grain size: 0.3 μm) (average iodine content: 2.0 mol%) 0.25 Silver iodobromide emulsion (average grain size: 0.4 μm) (Average iodine content: 8.0 mol%) 0.25 Sensitizing dye (S-9) 5.8 × 10 ^-4 Yellow coupler (Y-1) 0.6 Yellow coupler (Y-2) 0.32 DIR compound (D-1) 0.003 DIR compound ( D-2) 0.006 High boiling point solvent (Oil-2) 0.18 Gelatin 1.3 10th layer; Highly sensitive blue-sensitive milk Agent layer (BH) Silver iodobromide emulsion (average particle size 0.8 μm) (average iodine content 8.5 mol%) 0.5 Sensitizing dye (S-10) 3 × 10
^-4 sensitizing dye (S-11) 1.2 × 10
^-4 yellow coupler (Y-1) 0.18 yellow coupler (Y-2) 0.10 high boiling point solvent (Oil-2) 0.05 gelatin 1.0 11th layer; 1st protective layer (PRO-1) silver iodobromide emulsion (average grain 0.08μm diameter) 0.3 UV absorber (UV-1) 0.07 UV absorber (UV-2) 0.10 High boiling solvent (Oil-1) 0.07 High boiling solvent (Oil-3) 0.07 Gelatin 0.8 12th layer; Second protection Layer (PRO-2) Compound A 0.04 Compound B 0.004 Polymethyl methacrylate (average particle size 3 μm) 0.02 Methyl methacrylate: ethyl methacrylate: methacrylic acid = 3: 3: 4 (weight ratio) copolymer (average particle 0.13 gelatin 0.5 The sample 1 described above further comprises a dispersion aid Su-1, a coating aid Su-2, a hardener H-1, a stabilizer ST-1, a preservative DI-1, and a fog. Inhibitors AF-1 and AF-2, Dye A
Contains I-1 and AI-2.

[0060]

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[0061]

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[0062]

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[0063]

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[0064]

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[0065]

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[0066]

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[0067]

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Next, Samples 2 to 9 were prepared by changing the magenta couplers to be added to the sixth and seventh silver halide emulsion layers in Sample 1 as shown in Table 2 below.

The amount of the magenta coupler added to Samples 2 to 9 was equimolar to the amount of the magenta coupler used in Sample 1.

[0070]

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Each of the samples 1 to 9 prepared as described above was exposed to green light through a step wedge for sensitometry and processed under the following conditions.

Processing Step

[0073]

[Table 1]

The following color developing solutions, bleaching solutions, fixing solutions, stabilizing solutions and replenishers were used.

Color developer Water 800 ml Potassium carbonate 30 g Sodium bicarbonate 2.5 g Potassium sulfite 3.0 g Sodium bromide 1.3 g Potassium iodide 1.2 g Hydroxylamine sulfate 2.5 g Sodium chloride 0.6 g 4-Amino-3-methyl-N- Ethyl-N- (β-hydroxyethyl) aniline sulfate 4.5 g Diethylenetriaminepentaacetic acid 3.0 g Potassium hydroxide 1.2 g Add water to make up to 1 liter, and adjust the pH to 10.0.6 using potassium hydroxide or 20% sulfuric acid.

Color developing replenisher Water 800 ml Potassium carbonate 35 g Sodium bicarbonate 3 g Potassium sulfite 5 g Sodium bromide 0.4 g Hydroxylamine sulfate 3.1 g 4-Amino-3-methyl-N-ethyl-N- (β-hydroxyethyl) Aniline sulfate 6.3 g Potassium hydroxide 2 g Diethylenetriaminepentaacetic acid 3.0 g Add water to make 1 liter, and adjust the pH to 10.18 with potassium hydroxide or 20% sulfuric acid.

Bleaching solution Water 700 ml Ferric ammonium ammonium 1,3-diaminopropanetetraacetate 125 g Ethylenediaminetetraacetic acid 2 g Sodium nitrate 40 g Ammonium bromide 150 g Glacial acetic acid 40 g Add water to make 1 liter, and use ammonia water or glacial acetic acid. Adjust to pH 4.4.

Replenisher for bleaching Water 700 ml Ferric ammonium ammonium 1,3-diaminopropanetetraacetate 175 g Ethylenediaminetetraacetic acid 2 g Sodium nitrate 50 g Ammonium bromide 200 g Glacial acetic acid 56 g Adjusted to pH 4.0 using aqueous ammonia or glacial acetic acid To 1 liter.

Fixing solution Water 800 ml Ammonium thiocyanate 120 g Ammonium thiosulfate 150 g Sodium sulfite 15 g Ethylenediaminetetraacetic acid 2 g After adjusting the pH to 6.2 using glacial acetic acid or aqueous ammonia, add water to make 1 liter.

Fixing replenisher Water 800 ml Ammonium thiocyanate 150 g Ammonium thiosulfate 180 g Sodium sulfite 20 g Ethylenediaminetetraacetic acid 2 g After adjusting the pH to 6.5 using glacial acetic acid or aqueous ammonia, add water to make 1 liter.

Stabilizing solution and stabilizing replenisher water 900 ml pC ₈ H ₁₇ -C ₆ H ₄ -O- (CH ₂ CH ₂ O) ₁₀ H 2.0 g dimethylolurea 0.5 g hexamethylenetetramine 0.2 g 1,2-benz Isothiazolin-3-one 0.1 g Siloxane (UCC L-77) 0.1 g Ammonia water 0.5 ml Add water to make 1 liter, and adjust the pH to 8.5 using ammonia water or 50% sulfuric acid.

After the treatment, the sensitometric characteristics of green light measurement were measured for each of the above samples.

The sensitivity is obtained from the reciprocal of the exposure amount necessary to give a density of fog + 0.3, and is shown in Table 2 as a relative sensitivity with the sensitivity of Sample 1 being 100.

The spectral absorption maximum wavelength is the absorption maximum wavelength at a concentration of about 1.0.

The difference between the spectral absorption maximum wavelength at the maximum concentration and the spectral absorption maximum wavelength at the concentration of about 1.0 was obtained from the following equation, and was defined as Δλmax.

Δλmax = λmax _(Dmax) −λmax _{(D1.0) The} results are shown in Table 2.

[0087]

[Table 2]

As is clear from Table 2, Samples 1 and 2 using the comparative coupler had low sensitivity, low maximum density,
The spectral absorption maximum wavelength is short, and the movement of the spectral absorption maximum wavelength due to a change in concentration is large. On the other hand, it can be seen that Samples 3 to 9 using the coupler of the present invention have high sensitivity, a large maximum density, a preferable spectral absorption maximum wavelength, and a small change in the spectral absorption maximum wavelength due to a change in density. Further, as can be seen from Table 2, the maximum density of the magenta coupler of the present invention was large, so that the amount used could be reduced and the film could be made thinner, thereby improving the sharpness.

[0089]

According to the present invention, firstly, there is provided a silver halide color photographic light-sensitive material having high sensitivity, high color development, excellent color reproducibility, and low concentration dependence of the spectral absorption maximum wavelength of the coloring dye. Second, it was possible to provide a silver halide color photographic light-sensitive material having a reduced thickness and excellent sharpness.

──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int.Cl. ⁷ , DB name) G03C 7/384

Claims (5)

(57) [Claims] 1. A silver halide color photographic light-sensitive material having a photographic component layer comprising a blue-sensitive silver halide emulsion layer, a green-sensitive silver halide emulsion layer and a red-sensitive silver halide emulsion layer on a support. A silver halide color photographic light-sensitive material, characterized in that at least one of the silver halide emulsion layers contains at least one coupler represented by the following general formula [I]. Embedded image [In the formula, R ₁ represents a hydrogen atom or a group which is eliminated by reacting with an oxidized form of a developing agent, and R ₂ represents a chlorine atom or an alkoxy group. R ₃ represents a substituent, and n represents an integer of 1 to 5. R ₄ , R ₅ , R ₆ , R ₇ and R ₈ represent a halogen atom. ] 2. The silver halide color photographic light-sensitive material according to claim _1, wherein R ₁ in the general formula [I] is an arylthio group. 3. The method according to claim 1, wherein at least one of
_{3. A} silver halide color photographic light-sensitive material according to claim 2, wherein two R3s are substituted ortho to NHCO. 4. The method according to claim 1, wherein R ₄ , R ₅ , R
_6, a silver halide color photographic material of claim 2, wherein the R ₇ and R ₈ are both chlorine atoms. 5. The silver halide color photographic material according to claim 2, wherein R ₁ in the general formula [I] is a group represented by the following general formula [II]. Embedded image [Wherein, R ₂₁ represents a substituent. ]