JPH02195346A - Silver halide color photographic sensitive material containing novel cyan coupler - Google Patents

Abstract

PURPOSE:To obtain good color development property and sufficient color development density by incorporating a specified coupler in a red sensitive silver halide emulsion layer. CONSTITUTION:The red sensitive silver halide emulsion layer contains at least one of the couplers represented by formulae I and II in which R1 is an electron attracting group having a Hammett's sigmap value of 0.1-1.5; R2 is a substituent; R3 is alkyl or aryl; R4 is H, alkyl, or the like; R5 is a group substitutable on the benzene ring; n is an integer of 0-4, and when n is >=2, plural R5 may be same or different; and Y is H or a group releasable during development processing, thus permitting good color reproducibility and sufficient maximum density to be obtained, and change of hue against heat and temperature to be prevented.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a silver halide color photographic light-sensitive material, and more specifically, it contains an active site-substituted cyan dye-forming coupler with excellent color forming properties. This invention relates to silver halide color photographic materials.

[Background of the Invention] After a silver halide photographic material is exposed to light, it is subjected to a color development process, whereby an oxidized aromatic primary amine color developing agent and a dye-forming coupler react to form a dye.
A color image is formed.

Generally, this photographic method uses a subtractive color reproduction method to form yellow, magenta and cyan color images.

Phenols or naphthols have been widely used as cyan image forming couplers.

However, cyan images obtained from conventionally used phenols and naphthols have serious problems in color reproduction. The reason is that the absorption is not sharp on the shortwave side, and there is unnecessary absorption, that is, incorrect absorption, in the green region as well. As a result, in the case of negatives, it is necessary to correct the lack of absorption by masking, and in the case of paper, there is no means for correction, and the current situation is that the color reproducibility is considerably deteriorated.

Furthermore, dye images obtained from conventionally used phenols and naphthols have some problems in their storage stability. For example, U.S. Patent No. 2.3
87,531 and 20423.730, the dye images obtained from the 2-acylaminopheno, Lucien couplers generally have poor heat fastness;
U.S. Pat. No. 2,389,929 and U.S. Pat.
Dye images obtained from the 2.5-diacylaminophenol cyan coupler described in No. 772.182 generally have poor light fastness, and dye images obtained from the 1-hydroxy-2-natutamido cyan coupler generally have poor light fastness. and heat fastness.

Also, US Pat.
2,5-diacylaminophenol cyan coupler described in Publication No. 8 etc. and U.S. Patent No. 3.880.8.
Regarding the 2,5-diacylaminophenol cyan coupler described in No. 81, which has a hydroxyl group in the ballast part, in order to preserve the dye image for a long time, the fastness to light and heat and the occurrence of yellow stain must be considered. However, a satisfactory level has not yet been achieved.

Therefore, in order to solve these problems, Japanese Patent Laid-Open Nos. 83-199!152 and 63-25064
Pyrazoloazole type cyan couplers have been devised as described in Publication No. 9 and Publication No. 63-250Ei50.

However, all of these couplers are substituted with electron-withdrawing groups or hydrogen-bonding groups in order to satisfy the absorption wavelength of the coloring dye that is formed, so their coupling activity is greatly reduced, and conventional The biggest problem was that the color development was extremely poor compared to the phenol and naphthol type cyan couplers.

As a result of various studies regarding the above-mentioned problems, the present inventors succeeded in discovering a pyrazoloazole type cyan coupler having good coloring properties, and completed the present invention.

[Objective of the Invention] Therefore, the first object of the present invention is to provide a silver halide which exhibits good coloring properties and provides sufficient coloring density by containing an active site-substituted cyan dye-forming coupler having high reactivity. Our objective is to provide color photographic materials.

A second object of the present invention is to use a new cyan coupler that improves the drawbacks of the conventionally used cyan dye-forming couplers, that is, it has sharp absorption and absorbs in the blue and green regions. It is an object of the present invention to provide a silver halide color photographic material that gives a clear cyan image with low so-called excellent spectral absorption characteristics.

A third object of the present invention is to provide a silver halide color photographic light-sensitive material containing a novel cyan coupler capable of forming a cyan image that does not change in hue due to heat or temperature.

[Structure of the Invention] The object of the present invention is to provide a silver halide color photographic material having at least one silver halide emulsion layer on a support, in which the red-sensitive silver halide emulsion layer has the following structure. −
This was achieved using a silver 10-genide color photographic light-sensitive material characterized by containing at least one coupler selected from the couplers represented by formulas [1] and [01].

- Numerical formula [11 General formula [11] where RI represents an electron-withdrawing group with a Hammett's σ value of 0.1 to 1.5, R2 represents a substituent, R3 represents an alkyl group or an aryl group, R4 represents a hydrogen atom, an alkyl group, an aryl group, a sulfonyl group, a sulfinyl group, a carbonyl group, a sulfamoyl group, or a carbamoyl group, R5 represents a substituent that can be substituted on the benzene ring, and n represents an integer of 0 to 4. , when n is 2 or more, a plurality of R5s may be the same or different.

Further, Y represents a hydrogen atom or a group that can be separated during development. ] [Specific structure of the invention] In the coupler represented by the general formula (IF and [I[]) according to the present invention, the electron-withdrawing group represented by R1 includes a halogen atom, nitro, cyano, acyloxy, halogenated alkyl, Aryl halide, alkoxy halide,
Examples include multiple groups such as sulfonyl, carboxyl, sulfonyloxy, sulfinyl, sulfamoyl, phosphonyl, pyrrole, tetrazolyl, acyl, carbamoyl, and oxycarbonyl.

For example, the halogen atoms include atoms such as fluorine, chlorine, and bromine.

Examples of the acyloxy group include groups such as acetyloxy, 2-chloroacetyloxy, and benzoyloxy.

As the halogenated alkyl group, trifluoromethyl,
Examples include groups such as 2-chloroethyl.

Examples of the halogenated aryl group include groups such as pentafluorophenyl and pentachlorophenyl.

Examples of the sulfonyl group include groups such as methylsulfonyl, trifluoromethylsulfonyl, benzenesulfonyl, and p-)luenesulfonyl.

Examples of the sulfonyloxy group include groups such as methylsulfonyloxy, trifluoromethylsulfonyloxy, and benzenesulfonyloxy.

Examples of sulfinyl groups include methylsulfinyl, octylsulfinyl, 3-phenoxybutylsulfinyl,
Examples include groups such as m-pentadecylphenylsulfinyl.

Examples of the sulfamoyl group include N,N-dipropylsulfamoyl, N-phenyl-N-methylsulfamoyl,
Examples include groups such as N,N-diethylsulfamoyl and N-ethyl-N-dodecylsulfamoyl.

Examples of the phosphonyl group include groups such as ethoxyphosphonyl, butoxyphosphonyl, and phenoxyphosphonyl.

Examples of the tetrazolyl group include groups such as 1-tetrazolyl and 5-chloro-1-tetrazolyl.

Examples of the halogenated alkoxy group include trifluoromethoxy group.

Examples of the acyl group include an acetyl group, a dodecanoyl group, a benzoyl group, and a p-chlorobenzoyl group.

Examples of the carbamoyl group include N,N-dibutylcarbamoyl group and N-ethyl-N-dodecylcarbamoyl group.

Examples of the oxycarbonyl group include an alkoxycarbonyl group such as an ethoxycarbonyl group, an aryloxycarbonyl group such as a phenoxycarbonyl group, and the like.

In addition to the above electron-withdrawing groups, fluorinated alkylamide groups,
Examples include trifluoropropynyl group, carboxyethynyl group, dicyanoethynyl group, trifluoromethanesulfenyl group, thiocyanate group, and isothiocyanate group.

The above group may further have a substituent such as a diffusion-resistant group or an electron-withdrawing group.

There are no particular limitations on the substituents represented by R2 and R5. Typically, alkyl, aryl, anilino, acylamino, sulfonamide, alkylthio, arylthio,
Six groups include alkenyl, cycloalkyl, etc.
In addition, halogen atoms, cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl,
Acyl, carbamoyl, sulfamoyl, cyano, alkoxy, aryloxy, heterocyclicoxy, siloxy, acyloxy, carbamoyloxy, amino, alkylamino, imide, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, Also included are aryloxycarbonyl, 6 groups of heterocyclic thio, as well as spiro compound residues and bridged hydrocarbon compound residues.

The alkyl group represented by R2 and R5 has 1 carbon number
-32 is preferable, and it may be linear or branched.

The aryl group represented by R2 and R is preferably a phenyl group.

Examples of the acylamino group represented by R2 and R5 include an alkylcarbonylamino group and an arylcarbonylamino group.

Examples of the sulfonamide group represented by R7 and R5 include an alkylsulfonylamino group and an arylsulfonylamino group.

Examples of the alkyl component and aryl component in the alkylthio group and arylthio group represented by R2 and R5 include the alkyl group and aryl group represented by R2 and R5 above.

The alkenyl group represented by R2 and R5 has 2 to 32 carbon atoms, and the cycloalkyl group has 3 carbon atoms.
-12, especially those of 5-7 are preferred, and the alkenyl group may be linear or branched.

As the cycloalkenyl group represented by R2 and R3,
Those having 3 to 12 carbon atoms, particularly 5 to 7 carbon atoms, are preferred.

Sulfonyl groups represented by R2 and R2 include alkylsulfonyl groups, arylsulfonyl groups, etc.; sulfinyl groups include alkylsulfinyl groups, arylsulfinyl groups, etc.; phosphonyl groups include alkylphosphonyl groups, alkoxyphosphonyl groups, aryloxyphosphonyl groups, etc. Nyl group, arylphosphonyl group, etc.; Acyl group includes alkylcarbonyl group, arylcarbonyl group, etc.; carbamoyl group includes alkylcarbamoyl group, arylcarbamoyl group, etc.; sulfamoyl group includes alkylsulfamoyl group,
Niacyloxy groups such as arylsulfamoyl groups include alkylcarbonyloxy groups, arylcarbonyloxy groups, etc.; carbamoyloxy groups include alkylcarbamoyloxy groups, arylcarbamoyloxy groups, etc.; ureido groups include alkylureido groups, arylureido groups, etc. ; As the sulfamoylamino group, an alkylsulfamoylamino group, an arylsulfamoylamino group, etc.; as a heterocyclic group, a 5- to 7-membered one is preferable, and specifically, a 2-furyl group, a 2-thienyl group , 2-pyrimidinyl group, 2-benzothiazolyl group, etc.; as the heterocyclic oxy group, those having a 5- to 7-membered heterocycle are preferable, such as 3,
4,5.6-tetrahydrobilanyl-2-oxy group, 1
-Phenyltetrazole-5-oxy group, etc.; The heterocyclic thio group is preferably a 5- to 7-membered heterocyclic thio group, such as 2-pyridylthio group, 2-benzothiazolylthio group, 2.4-diphenoxy-1 , 3,5-triazole-6 monothio group, etc.; siloxy groups include trimethylsiloxy group, triethylsiloxy group, dimethylbutylsiloxy group, etc.; imide groups include succinimide group, 3-heptadecylsuccinimide group, phthalimide group group, glutarimide group, etc.; as a spiro compound residue, spiro[3,3]hebutane-
1-yl, etc.; As a bridged hydrocarbon compound residue, bicyclo[2°2.1
1 hebutan-1-yl, tricyclo[3°3.1.1'
- Tecodecan-1-yl, 7,7-dimethyl-bicycloC2,2,1]hebutan-1-yl, and the like.

Furthermore, the substituent R2 may be a hydrogen-bonding group such as the following.

Ra Bone Rb Ra 嘗Rb Ra Rb Ra Rb Ra Goose Rb Ra Livestock Rb [Ra and Rb represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic residue, etc.

Re and Rd represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic residue, a sulfonyl group, a sulfinyl group, a carbonyl group, and the like. g represents 0 or 1, and m represents 1 or 2. ] R3 represents an alkyl group (eg, methyl group, ethyl group, propyl group, butyl group, amyl group, octyl group, dodecyl group, etc.) or an aryl group.

The alkyl group represented by R1 may have a substituent as shown below.

That is, halogen atoms (e.g. atoms such as fluorine, chlorine, bromine, etc.), hydroxyl groups, nitro groups, cyano groups, alkyl groups (e.g. methyl groups, ethyl groups, propyl groups, 1so-
Propyl group, butyl group, tso-butyl group, 5ee-butyl group, tert-butyl group, pentyl group, so-pentyl group, 5ea-pentyl group, tert-pentyl group, hexyl group, heptyl group, octyl group 1. nonyl group,
decyl group, dodecyl group, 1so-dodecyl group, cetyl group, etc.), cyanoalkyl group (e.g. cyanomethyl group, etc.),
Fluorinated alkyl groups (e.g. trifluoromethyl group, octafluorobutyl group, etc.), aryl groups (e.g. phenyl group, naphthyl group, etc.), alkoxy groups (e.g. methoxy group, ethoxy group, β-ethoxy-ethoxy group, propyloxy group) , 1so-propyloxy group, butoxy group, 1s
o-butoxy group, 5ee-butoxy group, tert-butoxy group, pentyloxy group, 1so-pentyloxy group, tert-pentyloxy group, dodecyloxy group, etc.)
Aryloxy groups (e.g., phenoxy group, tolyloxy group, etc.), carboxyl group, alkyloxycarbonyl group (e.g., ethoxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (e.g., phenoxycarbonyl group, etc.), alkylacyloxy group (e.g. acetyloxy group, cyclohexylcarbonyloxy group, etc.), arylacyloxy group (e.g. penzoyloxy group, etc.), alkylamino group (e.g. ethylamino group, dimethylamino group, jetanolamino group, dodecylamino group, hexadecylamino group) ), arylamino groups (e.g., anilino group, naphthylamino group, etc.), alkylcarbamoyl groups (e.g., ethylcarbamoyl group, carboxyethylcarbamoyl group, dodecylcarbamoyl group, etc.), arylcarbamoyl groups (e.g., phenylcarbamoyl group, etc.), acylamino groups (e.g., methanamide group, dodecanamide group, hexadecanamide group, penzamide group, etc.), acyl group (e.g., benzoyl group, pentafluorobenzoyl group, ethylcarbonyl group, propylcarbonyl group, etc.), alkylthio group (e.g., methylthio group, propylthio group, octylthio group, dodecylthio group, etc.), alkylsulfonyl group (e.g. methylsulfonyl group, ethylsulfonyl group, octylsulfonyl group, decylsulfonyl group, dodecylsulfonyl group, etc.), alkylsulfamoyl group (e.g. ethylsulfamoyl group, pentylsulfonyl group, etc.), famoyl group, dodecylsulfamoyl group,
N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, etc.), alkylsulfonamide group (e.g. methylsulfonamide group, ethylsulfonamide group, dodecylsulfonamide group, p-dodecylphenylsulfonamide group, etc.) , an arylsulfonyl group (for example, an engineered nylsulfonyl group, etc.), and the like.

The aryl group represented by R3 is a phenyl group or a naphthyl group, and the phenyl group and naphthyl group may have a substituent as shown below.

That is, acylamino groups (e.g. methanamide group, ethanamide group, propaneamide group, butanamide group, hexaneamide group, octaneamide group, dodecanamide group, penzamide group, etc.), alkylsulfonamide groups (e.g. methanesulfonamide group, ethanesulfonamide group) group, propanesulfonamide group, hexanesulfonamide group,
Octanesulfonamide group, dodecanesulfonamide group (ml), arylsulfonamide group (e.g. benzenesulfonamide group, naphthalenesulfonamide group, etc.),
Carbamoyl groups (e.g. methylcarbamoyl group, ethylcarbamoyl group, propylcarbamoyl group, dodecylcarbamoyl group, phenylcarbamoyl group, etc.), sulfamoyl groups (e.g. N-methylsulfamoyl group, N-ethylsulfamoyl group, N-butylsulfamoyl group) famoyl group,
N-octylsulfamoyl group, N,N-dimethylsulfamoyl group, phenylsulfamoyl group, etc.), alkylureido groups (e.g. methylureido group, ethylureido group, etc.), arylureido groups (N e.g. phenylureido group) , naphthylureido group, etc.), alkyl group (e.g. methyl group, ethyl group, propyl group, octyl group, dodecyl group, etc.), alkoxy group (e.g. methoxy group, ethoxy group, propyloxy group, butyloxy group, octyloxy group, dodecyl group) (oxy group, etc.), amino group (e.g. methylamino group, ethylamino group, propylamino group, butylamino group, octylamino group, dodecylamino group, dimethylamino group, diethylamino group, anilino group, etc.), alkoxycarbonyl group (e.g. methoxy carbonyl group, ethoxycarbonyl group, butoxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.)
, or an aryloxycarbonyl group (for example, a phenoxycarbonyl group).

Substituent R4 represents a hydrogen atom, an alkyl group, an aryl group, a sulfonyl group, a sulfinyl group, a carbonyl group, a sulfamoyl group, and a carbamoyl group, and preferably a sulfonyl group, a sulfinyl group, and a carbonyl group.

In general formulas [11 and [II], Y is a hydrogen atom or a group that can be separated during development processing, for example, one that is separated from the compound of the present invention after the compound reacts with the oxidized developing agent. However, for example, the substituent represented by Y is
Groups that can be separated under alkaline conditions, such as those described in JP-A-61-228444, and JP-A-56-1
Examples include substituents that are coupled off by reaction with an oxidized developing agent, as described in Japanese Patent No. 81734.

Preferably Y is a hydrogen atom.

The cyan couplers represented by the general formulas [11 and [II] are more preferably represented by the following general formulas [1'] and [■'].

General Formula [I'] Specific compounds of the present invention are listed below, but these are representative compounds of the present invention, and the present invention is not limited thereto.

In the following margin general formulas [ ] In general formulas [I'] and [■'], R15R2, R
3, R4, Rs and n are the general formulas [11 and [
Rt, R2, Ri, R4, R5 and n in [II].

These cyan couplers of the present invention are J, Che■, Soc
, .

Perkin 1.2047 (1977), J.H.
eterocycle, Ches.

11, 423 (1974), Ber, 32.797
(1899), Chew.

Ber, 95.211B1.2881 (1982
), U.S. Patent No. 3.705.898, U.S. Patent No. 3
．． Specification No. 725,087, Japanese Patent Publication No. 4B-43947, Japanese Patent Publication No. 80-220348, Japanese Patent Publication No. 8G-43
No. 659, No. 82-123158, B3-
It can be easily synthesized by referring to JP-A No. 250649, JP-A No. 63-250650, JP-A No. 63-284753, and the like.

Typical synthesis examples are shown below.

Synthesis Example (Synthesis of Compound 43) 1.6 g of Intermediate 1 (compound described in JP-A-83-250650) was mixed with 1.2 g of mercaptopropionic acid.

2.1 g of anhydrous sodium carbonate and 80 ml of acetone were added, and the mixture was heated under reflux for 4 hours. After distilling off the solvent of the reaction solution, ethyl acetate room ml and IN hydrochloric acid aqueous solution 100 ml were added to separate the layers, and the organic layer was further washed with 1 OO ml of water three times, dried over magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. I left. The obtained solid was purified by silica gel column chromatography and recrystallized with a mixed solvent of chloroform-acetonitrile to obtain Compound 4B 5.
4. I got it.

(It was confirmed to be Compound 43 by 'HNMR, IR and mass spectrum.) When the color photographic light-sensitive material of the present invention is used as a full-color light-sensitive material, in addition to the cyan coupler of the present invention, a yellow coupler, a magenta coupler, etc. is used. The yellow coupler and magenta coupler are not particularly limited (known ones can be used).

As the yellow coupler, for example, acylacetanilide couplers can be used, including benzoylacetanilide and pivaloylacetanilide compounds.

As the magenta coupler, for example, 5-pyrazolone couplers, pyrazolopenzimidazole couplers, pyrazolotriazole couplers, and open-chain acylacetonitrile couplers can be used.

The silver halide color photographic material of the present invention may contain a water-soluble dye in the hydrophilic colloid layer as a filter dye or for various purposes such as preventing irradiation.

The halogen work color photographic light-sensitive material of the present invention may contain various other photographic additives. For example, antifoggants, development accelerators, development retarders, bleach accelerators, stabilizers, ultraviolet absorbers, color stain inhibitors, fluorescent whitening agents, color image fading inhibitors, antistatic agents, hardeners, interfaces. Activators, plasticizers, wetting agents, etc. can be used. (Refer to Research Disclosure No. 17843.) Furthermore, by coupling with competing couplers and oxidized forms of developing agents, development accelerators, bleach accelerators, developing agents, silver halide solvents, toning agents, hardeners, fogging agents, etc. Compounds that release photographically useful fragments such as agents, antifoggants, chemical sensitizers, spectral sensitizers, and desensitizers can be used.

The support for the silver halide color photographic light-sensitive material of the present invention is
Examples include baryta paper, polyethylene-coated paper, polypropylene synthetic paper, glass plates, polyester films such as cellulose acetate, cellulose nitrate, and polyethylene terephthalate, polyamide films, polycarbonate films, and polystyrene films. In the case of transparent supports, reflective layers are used. May be used together.

These supports are appropriately selected depending on the intended use of the photosensitive material.

Various coating methods such as dipping coating, air doctor coating, curtain coating, and hopper coating can be used to coat the emulsion layer and other constituent layers used in the present invention. It is also possible to simultaneously apply two or more layers as described in U.S. Patent No. 2,781,791 and U.S. Pat.

In the present invention, the coating position of each emulsion layer can be arbitrarily determined. It is preferable to do so.

In the photosensitive material of the present invention, it is optional to provide an intermediate layer with an appropriate thickness depending on the purpose, and a filter layer,
Various layers such as an anti-curl layer, a protective layer, and an antihalation layer can be used in appropriate combinations as constituent layers. Hydrophilic colloids can be used as binders in these constituent layers, and gelatin is preferably used. In addition, the various photographic additives mentioned in the explanation of the emulsion layer can be contained in the layer.

There are no particular limitations on the method of processing photographic materials using the silver halide emulsion of the present invention, and any commonly known processing method can be applied. For example, typical methods include a method in which bleach-fixing is performed after color development, followed by further washing and/or stabilization treatment if necessary; bleaching and fixing are performed separately after color development; Although the silver halide color photographic light-sensitive material of the present invention may be processed using any method including water washing and/or stabilization processing, the silver halide color photographic light-sensitive material of the present invention can be processed in the steps of color development, bleach-fixing, and water washing (or stabilization). Suitable for rapid processing.

[Examples] Specific examples of the present invention will be described below, but the embodiments of the present invention are not limited thereto.

Example-1 Here, the present invention was applied to color paper.

That is, on a paper support laminated on both sides with polyethylene, the following layers were sequentially coated from the support side to prepare silver halide color photographic materials N11-NIL18.

Layer 1...t, 2g/n gelatin, 0.32g
blue-sensitive silver chlorobromide emulsion (silver chloride content 99, .3 mol%), 0.80 g/- of yellow coupler dissolved in 0.50 g/g of dioctyl phthalate ( A layer containing Y-1).

Layer 2...0.70g/rrr gelatin, 30
i+g/rr? anti-irradiation dye (AI
-1), an intermediate layer consisting of (Al-2) of 2 hg/g.

Layer 3: 1.25g/go gelatin, 0.25
green-sensitive silver chlorobromide emulsion (silver chloride content 99.5 mol%), 0.30 g/rr? Q dissolved in dioctyl phthalate of 'F4g/rrr of magenta coupler C
A layer containing M-1).

Layer 4...1.20g/rr? middle layer consisting of gelatin.

Layer 5...1.20g 10f gelatin, 0.3
0g/rr? red-sensitive silver chlorobromide emulsion (silver chloride content: 99%)
．． 7 mol %) and 0.9 mmol/M of the cyan coupler shown in Table 1 dissolved in 0.45 g/nf of dioctyl phthalate.

Layer 6...1.00 g/rd gelatin and 0.20 g/n-? A layer containing 0.30 g/rrr of ultraviolet absorber (UV-1) dissolved in dioctyl phthalate.

Layer 7: Layer containing 0.50 g/rrr of gelatin.

C-1 C-2 t, It Cl I-1 I-2 In addition, as a hardening agent, sodium 2,4-dichloro-6-hydroxy-s-triazine was added in layers 2.4 and 7. Each was added in an amount of 0.017 g per 1 g of gelatin.

The obtained sample was passed through a photosensitive needle KS-7 type (manufactured by Konica Corporation).
After wedge exposure using a 3D emulsion layer and processing according to the following color development processing steps, the highest density of the red-sensitive emulsion layer (
D m a was measured.

[Processing process]

UV-1 0■ C5tixtLIJ Temperature color development 34.7±0.3℃ Bleach-fixing 34.7±0.5℃ Stabilization 30-34℃ Drying 60-80℃ Color developer> Pure water triethanolamine N,N-diethylhydroxyl potassium chloride 4 hours 45 seconds 50 seconds 90 seconds 60 seconds N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 5 g Sodium tetrapolyphosphate 2 g potassium carbonate
30g potassium sulfite
0.2g optical brightener (4,4'-
Diaminostilbendisulfonic acid derivative> Add tg pure water to bring the total amount to 1 g, and adjust the pH to 10.2.

Bleach-fix solution> Ethylenediaminetetraacetic acid iron (m) Ammonium dihydrate 6Qg Ethylenediaminetetraacetic acid 3g Ammonium thiosulfate (70% solution) LOOmj Ammonium sulfite (40% solution) Adjust to pH 5.7 with 27.5ml potassium carbonate or glacial acetic acid Then add water to bring the total amount to 1 g.

Stabilizing liquid> 5-chloro-2-methyl-4-isothiazolin-3-one Igl-hydroxyethylidene-1゜1-diphosphonic acid Add 2g of water to make 1g, and add p)1 with sulfuric acid or potassium hydroxide. 7
．． Adjust to 0.

Further, the color reproducibility of the samples Nα1 to Magneto 18 was evaluated by the following method.

First, color negative film (Konica Color GX-100
: manufactured by Konica Corporation) and camera (Konica FT-I MO
TOR: manufactured by Konica Corporation) was used to photograph a color checker manufactured by Macbeth. Subsequently, a color negative development process (CNK-1 manufactured by Konica Corporation) was performed, and the obtained negative image was printed on a Konica color printer CL-P 2000 (
The above samples Nα1 to Ma181 were
;: Printed in a size of 82m5 x 117mm,
Practical prints were obtained in the same manner as above. Printer conditions during printing were set for each sample so that gray on the color checker turned gray on the print.

The color reproducibility and blackness of the obtained practical prints were visually evaluated. The results are summarized in Table-1.

Margin Table-1 Below: Color Reproducibility (Hue, Saturation) Color Reproducibility (Hue, Saturation) Color Reproducibility (Hue, Saturation) Poorly Good Very Good As is clear from Table-1, the present invention Sample Nα1 containing the cyan coupler CC-1 has good color development and a high maximum density, but the color reproducibility is extremely insufficient. On the other hand, cyan coupler C outside the present invention
Sample 2, which contains C-2, greatly improves color reproducibility, but has a low maximum density, resulting in poor blackness.

On the other hand, sample magnets 3 to Nα18 containing the cyan coupler of the present invention all have good color development, high maximum density, and good color reproducibility and blackness.

[Effects of the Invention] The silver halide color photographic light-sensitive material of the present invention has good color reproducibility, a sufficient maximum density, and no change in hue due to heat or temperature.

Claims (1)

[Scope of Claims] In a silver halide color photographic light-sensitive material having at least one silver halide emulsion layer on a support, the red-sensitive silver halide emulsion layer has the following general formulas [I] and [II].
] A silver halide color photographic material containing at least one coupler selected from the couplers shown below. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ General formula [II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R_1 is Hammett's σ_p value of 0.1 to 1.5
represents an electron-withdrawing group, R_2 represents a substituent, R_3 represents an alkyl group or an aryl group, and R_4 represents a hydrogen atom, an alkyl group, an aryl group, a sulfonyl group, a sulfinyl group, a carbonyl group, a sulfamoyl group, or a carbamoyl group. R_5 represents a substituent that can be substituted on the benzene ring, n represents an integer of 0 to 4, and when n is 2 or more, a plurality of R_5 may be the same or different. Further, Y represents a hydrogen atom or a group that can be separated during development. ]