JPH07119991B2 - Silver halide photographic light-sensitive material containing novel magenta coupler - Google Patents

Description

TECHNICAL FIELD The present invention relates to a silver halide photographic light-sensitive material containing a magenta coupler capable of forming a magenta dye image with high color development and excellent color reproduction. More specifically, it relates to a silver halide color photographic light-sensitive material containing a novel 1H-pyrazolo [1,5-b] [1,2,4] triazole magenta coupler.

BACKGROUND OF THE INVENTION Usually, in a silver halide color photographic light-sensitive material, exposed silver halide grains are reduced by an aromatic primary amine type color developing agent, and an oxidized product of the color developing agent produced at this time. And a coupler forming a yellow, magenta, and cyan dye to form a dye image.

In order to form the magenta dye, a coupler which has been conventionally put to practical use is a pyrazolone type coupler, but this has a secondary absorption at around 430 nm, which causes a color stain and is not preferable in color reproduction. .

For this reason, various attempts have been made to reduce this side absorption,
For example, British Patent No. 1,047,612 has a pyrazolobenzimidazole type coupler, US Pat. No. 3,770,447 has an indazolone type coupler, and US Pat. No. 3,725,067 has a 1H-pyrazolo [3,2-c] [1,2,4] triazole type. Couplers have been proposed. However, although these couplers are superior to pyrazolone type couplers in terms of side absorption, various conditions for practical use as a silver halide color photographic light-sensitive material, such as color developability, spectral absorption characteristics, and synthesis. It does not satisfy all of the easiness, solubility, etc., and is insufficient. On the other hand, recently, as a new magenta coupler, 1H-pyrazolo [1,5-b] [1,
2,4] triazole compounds have been proposed in JP-A-59-171956. The coupler described in this patent is 43
There is no secondary absorption around 0 nm, the spectral absorption characteristics are favorable, and the synthesis is relatively easy, but it is still insufficient in terms of color development, and further improvement has been desired.

[Object of the Invention] An object of the present invention is to provide a silver halide photographic light-sensitive material containing a novel magenta dye image-forming coupler which is excellent in color reproduction and color development.

[Constitution of the Invention] The above object of the present invention is to provide a silver halide photographic light-sensitive material having at least one silver halide emulsion layer on a support, wherein at least one of the silver halide emulsion layers comprises
1H- substituted at the 2-position with a group represented by the following general formula [I]
It was achieved by a silver halide photographic light-sensitive material containing at least one pyrazolo [1,5-b] [1,2,4] triazole-based magenta coupler.

General formula [I] In the formula, R ₁ , R ₂ and R ₃ each represent a substituent, and m represents an integer of 0 to 3. When m is 2 or more, R ₃ may be the same or different.

[Specific Structure of the Invention] Hereinafter, the present invention will be described more specifically.

The pyrazolotriazole-based magenta coupler substituted with a group represented by the general formula [I] (hereinafter referred to as the coupler of the present invention) is characterized by having a substituted phenyl group at the 2-position, and R ₁ and R ₂ And the substituent represented by R ₃ is not particularly limited, but is a halogen atom (eg, fluorine, chlorine, bromine atom), a straight chain, branched or cyclic alkyl group having 1 to 22 carbon atoms (eg, methyl, ethyl, isopropyl, t -Butyl, octadecyl, cyclohexyl group), aryl group (eg phenyl, naphthyl group), alkoxy group (eg methoxy, ethoxy, dodecyloxy group), aryloxy group (eg phenoxy, naphthoxy group), acyloxy group (eg acetoxy, benzoyl) Oxy group),
Alkylthio group (eg methylthio, dodecylthio group), arylthio group (eg phenylthio group), amino group (eg methylamino, diethylamino, anilino group), cyano group, nitro group, hydroxy group, carboxyl group, acylamino group, (eg acetamide, Benzamide group), sulfonamide group (eg methanesulfonamide, benzenesulfonamide group), ureido group (eg methylureido, phenylureido group), carbamoyl group (eg methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl group), sulfamoyl group (eg Dimethylsulfamoyl, dodecylflufamoyl, phenylsulfamoyl group), acyl group (eg acetyl, benzoyl group), sulfonyl group (eg methanesulfonyl, benzene) Ruhoniru group), an alkoxycarbonyl group (e.g. methoxycarbonyl, octadecyl group), a Hajime Tamaki (e.g. 2-furyl, 2-thionyl, may be mentioned 2-pyrimidinyl group).

These groups may further have a substituent, and examples of the substituent include the above-mentioned halogen atom, aryl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, amino group, acylamino group, sulfonamide group,
Examples thereof include ureido group, carbamoyl group, sulfamoyl group, sulfonyl group and the like.

R ₁ and R ₂ are preferably a halogen atom, an alkyl group or an alkoxy group, and most preferably an alkyl group.

R ₃ is preferably an alkyl group, an acylamino group, a sulfonamide group, a ureido group or an alkoxycarbonylamino group, and particularly preferably an alkyl group, an acylamino group or a sulfonamide group.

The group represented by the general formula [I] is preferably the following general formula [I
I], [III] and [IV].

General formula [II] General formula [III] General formula [IV] In the formula, R ₁ and R ₃ have the same meanings as those in the above general formula [I].

Of the present invention substituted with a group represented by the above general formula [I]
The 1H-pyrazolo [1,5-b] [1,2,4] triazole magenta coupler is preferably represented by the following general formula [V].

General formula [V] In the formula, Is represented by the above-mentioned general formula [I], and Z is a hydrogen atom or a group which is released when a dye is formed by coupling with an oxidized product of an aromatic primary amine color developing agent.

R ₄ is an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, −COR ₃ ′, −OCOR ₃ ′, −COOR ₃ ′, It represents a group represented by —SO ₂ R ₃ ′ or —OSO ₂ R ₃ ′. (here,
R ₃ ′ represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, and R ₃ ″ and R ₃ each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group.) In [V], the alkyl group represented by R ₄ , R ₃ ′, R ₃ ″ and R ₃ preferably has 1 to 20 carbon atoms.
Up to linear or branched alkyl groups such as methyl group, ethyl group, propyl group, i-propyl group, sec-
Examples thereof include a butyl group, an n-butyl group, a t-butyl group, an n-octyl group, a t-octyl group, a dodecyl group, and an octadecyl group. Examples of the cycloalkyl group include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, A cyclohexenyl group etc. are mentioned. These groups are further substituted (for example, halogen atom, nitro group, cyano group, alkoxy group, aryloxy group, amino group, acylamino group, carbamoyl group, sulfonamide group, sulfamoyl group, imide group, alkylthio group, arylthio group, It may have an aryl group, an alkoxycarbonyl group, or an acyl group, specifically, a chloromethyl group, a bromomethyl group,
Trichloromethyl group, β-nitroethyl group, δ-cyanobutyl group, methoxymethyl group, ethoxyethyl group, phenoxyethyl group, N-methylaminoethyl group, dimethylaminobutyl group, acetaminoethyl group, benzoylamino group, propyl group, Ethylcarbamoylethyl group, methanesulfonamidoethyl group, ethylthioethyl group, p
-Methoxyphenylthiomethyl group, phenylmethyl group,
those having a p-chlorophenylmethyl group, a naphthylethyl group, an ethoxycarbonylethyl group, an acetylethyl group, etc.) are also included.

Further, the aryl group preferably represents a phenyl group or a naphthyl group, and includes those having the substituent shown in the item of the alkyl group.

The heterocyclic group preferably represents a 5-membered or 6-membered ring having at least one of nitrogen atom, oxygen atom and sulfur atom, and may or may not have aromaticity. For example, pyridyl group, quinolyl group, pyrrolyl group, morpholyl group, furanyl group, tetrahydrofuranyl group, pyrazolyl group, triazolyl group,
Examples thereof include a tetrazolyl group, a thiazolyl group, an oxazolyl group, an imidazolyl group and a thiadiazolyl group. In addition, these also include those having the substituent shown in the section of the alkyl group.

When the heterocyclic group is a 1H-pyrazolo [1,5-b] [1,2,4] triazole compound, a bis type 1H-pyrazolo [1,5-b] [1,2,4] is used. It is a magenta coupler which forms triazole compounds but is of course included in the present invention.

Next, specific examples of R ₄ represented by the general formula [V] will be shown.

CH ₃ −, C ₂ H ₅ −, (n) C ₃ H ₇ −, (n) C ₈ H ₁₇ −, (n) C ₁₅ H ₃₁ −, (t) C ₄ H ₉ −, (t) C ₅ H ₁₁ −, (t) C ₈ H ₁₇ −, −C ₁₇ H ₃₅ , −CH ₂ CH ₂ CH ₂ OC ₁₂ H ₂₅ , −CH ₂ CH ₂ CONHC ₁₄ H ₂₉ , −OC ₁₂ H ₂₅ , -NHC ₁₄ H ₂₉ , -S-C ₁₆ H ₃₃ , -CONHC ₁₄ H ₂₉ , -NHSO ₂ C ₁₆ H ₃₃ , -SO ₂ NHC ₁₆ H ₃₃ , -COC ₁₁ H ₂₃ , -OCOC ₁₅ H ₃₁ , -COOC ₁₂ H ₂₅ , -SO ₂ C ₁₆ H ₃₃ , The group capable of splitting represented by Z is a halogen atom,
Alkoxy group, aryloxy group, acyloxy group, arylthio group, alkylthio group, (Z ₁ is a nitrogen atom together with a carbon atom, an oxygen atom, a nitrogen atom,
It represents a group of atoms required to form a 5- or 6-membered ring with an atom selected from sulfur atoms. ), An acylamino group,
Sulfonamide groups and the like, and further alkylene groups (in this case, 1H-pyrazolo [1,5-b] [1,2,4] triazole type magenta couplers having an alkylene group bonded to the bis group at the active site. Is also included.

Specific examples will be given below.

Halogen atom: chlorine, bromine, fluorine Alkoxy group: ethoxy group, benzyloxy group, methoxyethylcarbamoylmethoxy group, tetradecylcarbamoylmethoxy group, etc.Aryloxy group: phenoxy group, 4-methoxyphenoxy group, 4-nitrophenoxy group, etc. Acyloxy Group: acetoxy group, myristoyloxy group, benzoyloxy group, etc. Arylthio group: phenylthio group, 2-butoxy-5-
Octylphenylthio group, 2,5-dihexyloxyphenylthio group, etc.Alkylthio group: methylthio group, octylthio group, hexadecylthio group, benzylthio group, 2- (diethylamino) ethylthio group, ethoxycarbonylmethylthio group,
Ethoxyethylthio group, phenoxyethylthio group, etc. Etc.

In the magenta coupler represented by the general formula [V], when the coupler is used for positive image formation,
R ₄ is preferably an alkyl group, and more preferably the case where the following Condition 1 is satisfied.

Condition 1 Only one hydrogen atom is bonded to the carbon atom directly connected to the heterocycle, which is the mother nucleus of the coupler, or none is bonded at all.

Among the above, the most preferable one is represented by the following general formula [VI].

General formula [VI] In the formula, R ₅ , R ₆ and R ₇ are each a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group,
Cycloalkenyl group, alkynyl group, aryl group, heterocyclic group, acyl group, sulfonyl group, sulfinyl group, phosphonyl group, carbamoyl group, sulfamoyl group, cyano group, spiro compound residue, bridged hydrocarbon compound residue, alkoxy group , Aryloxy group, heterocyclic oxy group, siloxy group, acyloxy group, carbamoyloxy group, amino group, acylamino group, sulfonamide group, imide group, ureido group, sulfamoylamino group, alkoxycarbonylamino group, aryloxycarbonyl It represents an amino group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylthio group, an arylthio group or a heterocyclic thio group, and at least two of R ₅ , R ₆ and R ₇ are not hydrogen atoms.

Also, at least two of the above R ₅ , R ₆ and R ₇ , for example R ₅
And R ₆ may combine with each other to form a saturated or unsaturated ring (eg, cycloalkane, cycloalkene, heterocycle), and R ₇ bonds to the ring to form a bridged hydrocarbon compound residue. You may.

The groups represented by R _{5 to} R ₇ may have a substituent.

Among the general formula [VI], (i) when at least two of R _{5 to} R ₇ are alkyl groups, (ii) one of R _{5 to} R ₇ , for example, R ₇ is a hydrogen atom. And when the other two R ₅ and R ₆ combine to form a cycloalkyl with the root carbon atom.

Further, among (i), 2 of R _{5 to} R ₇ is preferable.
One is an alkyl group and the other one is a hydrogen atom or an alkyl group.

Here, the alkyl and the cycloalkyl may further have a substituent.

Further, in the magenta coupler represented by the general formula [V], when the coupler is used for forming a negative image, R _{4 in} the formula is preferably an alkyl group, more preferably the following Condition 2 is satisfied. This is the case.

Condition 2 At least two hydrogen atoms are bonded to the carbon atom directly connected to the heterocycle, which is the mother nucleus of the coupler.

Among the above, the most preferable one is represented by the following general formula [VI].

Formula [VI] R ₈ —CH ₂ — In the formula, R ₈ is a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl, a heterocyclic group, an acyl group, or a sulfonyl. Group, flufinyl group, phosphonyl group, carbamoyl group, sulfamoyl group, cyano group, spiro compound residue,
Bridged hydrocarbon compound residue, alkoxy group, aryloxy group, heterocyclic oxy group, siloxy group, acyloxy group, carbamoyloxy group, amino group, acylamino group, sulfonamide group, imide group, ureido group, sulfamoylamino Group, alkoxycarbonylamino group, aryloxycarbonylamino group, alkoxycarbonyl group, aryloxycarbonyl group, alkylthio group,
It represents an arylthio group or a heterocyclic thio group.

The group represented by R ₈ also includes those having a substituent.

R ₈ is preferably a hydrogen atom or an alkyl group.

Further, the magenta coupler of the present invention may be a polymer coupler. For example, R _{1 to} R ₄ in the general formula [V]
The magenta coupler of the present invention constitutes a polymer coupler when the substituent contained in contains a polymer chain.

When the magenta coupler of the present invention is a polymer coupler, the monomer unit for deriving the polymer coupler is preferably one in which R ₃ has an ethylenically unsaturated group in the general formula [V].

In the above, the polymer coupler having a repeating unit derived from a monomer having an ethylenically unsaturated group,
It may be a homopolymer consisting of one kind of the coupler residue of the present invention or a copolymer consisting of two or more kinds,
It may also be a copolymer with other copolymerizable comonomers.

Hereinafter, 1H-pyrazolo [1,5-b] used in the present invention
Specific examples of the [1,2,4] triazole-based magenta coupler are shown below, but the invention is not limited thereto.

Next, the synthesis method will be described. The compounds of the present invention are disclosed in
It can be synthesized according to the method described in 47-24321, 59-171956, 60-172982 and the like.

Synthesis of Exemplified Compound (3) The compound (II) could be quantitatively synthesized by a usual method from 3-nitro-2,4,6-trimethylbenzonitrile synthesized by the method described in Ann. Chem., Vol. 278, 213.

Dissolve (I) 9.7 g and (II) 27.3 g in 200 ml of methanol,
The mixture was stirred at room temperature for 2 hours. To this, a methanol solution of hydroxylamine (prepared by adding 19.3 g of 28% methanol solution of sodium methoxide to 7 g of hydroxylamine hydrochloride and filtering the precipitated salt) was added and stirred at room temperature for 1 hour. After methanol was distilled off under reduced pressure, water was added to the residue and the mixture was extracted with ethyl acetate. This was concentrated under reduced pressure to obtain a crude product of (III). This was dissolved in 200 ml of tetrahydrofuran, 12 ml of triethylamine was added, and the mixture was stirred. 16 g of p-toluenesulfonyl chloride was slowly added thereto, and the mixture was stirred for 30 minutes. The insoluble material was filtered off, and the mixture was heated under reflux for 5 hours. The solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. This was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate to obtain 9.1 g of (IV).

Next, 8.6 g of (IV) was dissolved in 170 ml of dimethylformamide, and 50 ml of water and 50 ml of ammonium water were added thereto. This solution was heated on a water bath, 26 g of sodium hydrosulfite was added thereto, and the mixture was stirred for 30 minutes.

The reaction mixture was concentrated under reduced pressure, water was added to the residue, the mixture was neutralized with hydrochloric acid, and then extracted with ethyl acetate. The solvent was distilled off, 20 ml of acetonitrile, 2.4 g of pyridine and 10.8 g of p-dodecyloxybenzenesulfonyl chloride were added to the residue, and the mixture was stirred at room temperature for 2 hours. The precipitated solid was filtered and washed with acetonitrile to obtain 8.0 g of (V).

Next, 5.8 g of (V) was dissolved in 50 ml of chloroform and cooled to 10 ° C. To this was added 1.3 g of N-chlorosuccinimide,
It was stirred for 30 minutes. Water was added, the chloroform layer was removed, washed with water, and then concentrated under reduced pressure. The acidity was recrystallized from acetonitrile to obtain 5.7 g of compound (3). The structure was confirmed by elemental analysis, NMR spectrum and mass spectrum. The results of elemental analysis are shown below.

C ₃₂ H ₄₄ N ₅ O ₃ SCl Theoretical value C: 62.57 H: 7.22 N: 11.40 S: 5.22 Cl: 5.77 (%) Experimental value C: 62.69 H: 7.16 N: 11.45 S: 5.40 Cl: 5.63 (%) Book When the magenta coupler of the invention is added to the silver halide emulsion layer, it is generally used in the range of 0.005 to 2 mol, preferably 0.03 to 0.5 mol, per mol of silver halide.

In order to incorporate the magenta coupler of the present invention into a silver halide photographic light-sensitive material, various methods such as a solid dispersion method, a latex dispersion method and an oil-in-water type emulsion dispersion method can be used. For example, in the oil-in-water emulsion dispersion method, the above compound is usually added to a high-boiling organic solvent having a boiling point of about 150 ° C or higher (eg, phthalic acid ester, phosphoric acid ester, etc.), if necessary, low boiling point, and / or water-soluble. It may be dissolved in an organic solvent in combination, emulsified and dispersed in a hydrophilic binder such as an aqueous gelatin solution with a surfactant, and then added to the desired hydrophilic colloid layer.

The silver halide photographic light-sensitive material of the present invention may be monochromatic or polychromatic. In the case of a multi-color silver halide photographic light-sensitive material, a silver halide emulsion layer and a non-cyclic layer usually containing magenta, yellow and cyan couplers as photographic couplers in order to perform color reduction method color reproduction. Has a structure in which it is laminated on the support in an appropriate number of layers and layer order, but the number of layers and layer order may be appropriately changed depending on the priority performance and the purpose of use.

The silver halide used in the silver halide photographic light-sensitive material of the present invention is used in ordinary silver halide emulsions such as silver bromide, silver iodobromide, silver iodochloride, silver chlorobromide, and silver chloride. Any one can be used.

The silver halide emulsion used in the present invention is a sulfur sensitizing method,
It is chemically sensitized by a selenium sensitization method, a reduction sensitization method, a noble metal sensitization method.

The silver halide emulsion used in the present invention can be optically sensitized to a desired wavelength region by using a dye known as a sensitizing dye in the photographic industry.

The silver halide photographic light-sensitive material of the present invention includes an image stabilizer,
Antifoggant, hardener, plasticizer, latex, surfactant, color antifoggant, ultraviolet absorber, matting agent, lubricant,
Additives such as antistatic agents can be optionally used.

The silver halide photographic light-sensitive material of the present invention can form a dye image by performing various color development processes.

[Specific effects of the invention] The silver halide photographic light-sensitive material of the present invention is excellent in color development of the magenta coupler, and the magenta dye formed has good spectral absorption characteristics, excellent color reproducibility, and high sensitivity. The gradation is excellent.

Specific Examples of the Invention Hereinafter, the present invention will be specifically described with reference to Examples, but the embodiments of the present invention are not limited thereto.

Example-1 0.15 mol of each of the magenta coupler and the comparative coupler of the present invention as shown in Table 1 was taken with respect to 1 mol of silver.
Dibutyl phthalate in an amount 1 times the weight of the coupler and ethyl acetate in an amount 3 times the weight of the coupler were added, and the mixture was heated to 60 ° C. and completely dissolved. This solution was mixed with 1200 ml of a 5% aqueous solution of alkanol B (alkylnaphthalene sulfonate, manufactured by DuPont) and 120 ml of a 5% gelatin solution, and the mixture was emulsified and dispersed by an ultrasonic disperser to obtain an emulsion. Thereafter, this dispersion was added to 4 kg of a green-sensitive silver chlorobromide emulsion (containing 80 mol% of silver bromide), and a 2% solution of 1,2-bis (vinylsulfonyl) ethane (water: methanol as a hardener). = 1: 1) Add 120 ml,
Samples 1 to 8 were prepared by coating and drying on a paper support laminated on both sides with polyethylene. (Coating silver amount 5mg / 100c
m ² ) The sample thus obtained was subjected to wedge exposure according to a conventional method and then subjected to the following development treatment.

[Development process] Temperature Time Color development 38 ° C 3 minutes 30 seconds Bleach fixing 33 ° C 1 minute 30 seconds Stabilization treatment / or water washing treatment 25-30 ° C 3 minutes Drying 75-80 ° C 2 minutes In each processing step The composition of the treatment liquid used is as follows.

[Color developer] Benzyl alcohol 15 ml Ethylene glycol 15 ml Potassium sulfite 2.0 g Potassium bromide 0.7 g Sodium chloride 0.2 g Potassium carbonate 30.0 g Hydroxylamine sulfate 3.0 g Polyphosphoric acid (TPPS) 2.5 g 3-Methyl-4-amino-N -Ethyl-N- (β-methanesulfonamidoethyl) -aniline sulfate 5.5 g Optical brightener (4,4'-diaminostilbenedisulfonic acid derivative) 1.0 g Potassium hydroxide 2.0 g Add water to make the total amount 1 , Adjust the pH to 10.20.

[Bleaching fixer] Ethylenediaminetetraacetic acid ferric ammonium dihydrate
60 g Ethylenediaminetetraacetic acid 3 g Ammonium thiosulfate (70% solution) 100 ml Ammonium sulfite (40% solution) 27.5 ml Adjust the pH to 7.1 with potassium carbonate or glacial acetic acid and add water to bring the total volume to 1.

[Stabilizing liquid] 5-chloro-2-methyl-4-isothiazolin-3-one 1.0g Ethylene glycol 10g 1-Hydroxyethylidene-1,1'-diphosphonic acid 2.5g Bismuth chloride 0.2g Magnesium chloride 0.1g Ammonium hydroxide (28% aqueous solution) 2.0g Sodium nitrilotriacetate 1.0g Add water to make the total amount 1 and adjust the pH to 7.0 with ammonium hydroxide or sulfuric acid.

From the results shown in Table 1, it was found that the sample using the magenta coupler of the present invention exhibits excellent characteristics in terms of sensitivity, gradation and maximum density.

The magenta dye images of these samples of the present invention had excellent hue and high saturation.

Example-2 A multilayer silver halide color photographic light-sensitive material having the layer structure shown in Table 2 was prepared.

DBP in the table represents dibutyl phthalate.

The antioxidant, the stain inhibitor and the ultraviolet absorber used here are the compounds shown below.

The yellow coupler and the cyan coupler used here are compounds having the following structures.

[Yellow coupler] [Cyan coupler] Table 3 shows the results of the same development treatment as in Example-1 after the multilayer silver halide color photographic light-sensitive material was subjected to wedge exposure with white light.

As can be seen from Table 3, in the multilayer silver halide color photographic light-sensitive material, Samples 12 to 15 of the present invention using the coupler having a primary alkyl group at the 6-position were compared with Comparative Samples 9 and 11, and Sample 16 of the present invention using a coupler having a tertiary alkyl group at the 6-position has a higher maximum density than Comparative Sample 10,
It can be seen that it is excellent in color development, and further exhibits excellent characteristics in sensitivity and gradation.

Example 3 As shown in Table 4, each of the magenta coupler of the present invention and the comparative coupler was taken in an amount of 0.1 mol per 1 mol of silver,
One part by weight of coupler, tricresyl phosphate, and 3 parts by weight ethyl acetate were added, and the mixture was heated to 60 ° C. to completely dissolve it. This solution was mixed with 1200 ml of a 5% gelatin aqueous solution containing 120 ml of a 5% aqueous solution of alkanol B (alkylnaphthalene sulfonate, manufactured by DuPont) and emulsified and dispersed by an ultrasonic disperser to obtain an emulsion. Then, this dispersion was added to 4 kg of green-sensitive silver iodobromide (containing 6 mol% of silver iodobromide), and a 2% solution of 1,2-bis (vinylsulfonyl) ethane (water: methanol) as a hardener. = 1: 1) Add 120 ml,
Samples 17-29 were prepared by coating and drying on a transparent polyester base which was subbed. (Amount of coated silver: 20 mg / 100 cm ² ) The sample thus obtained was subjected to wedge exposure according to a conventional method and then subjected to the following development processing. The results are shown in Table 4.

[Development process] 1. Color development 38 ℃ 3 minutes 15 seconds 2. Bleach 38 ℃ 6 minutes 30 seconds 3. Washing with water 38 ℃ 3 minutes 15 seconds 4. Fixing 38 ℃ 6 minutes 30 seconds 5. Washing with water 38 ℃ 3 minutes 15 seconds 6. Stability 38 ℃ 3 minutes 15 seconds The composition of treatment liquid used in each process is as follows.

[Color developer composition] Sodium nitrilotriacetate 1.0 g Sodium sulfite 4.0 g Sodium carbonate 30.0 g Potassium bromide 1.5 g Hydroxylamine sulfate 2.5 g 4- (N-ethyl-N- (3-hydroxyethylamino) -2- Methyl-aniline sulfate 4.5g Add water 1 pH 10.02 [Bleaching composition] Ammonium bromide 160.0 g Ammonia water (28%) 25.0 ml Ethylenediamine-tetraacetic acid sodium iron salt 130 g Glacial acetic acid 14 ml Add water 1 [ Fixer composition] Sodium terra polyphosphate 2.0 g Sodium sulfite 4.0 g Ammonium thiosulfate (70%) 160 ml Sodium bisulfite 5.0 g Add water 1 [Stable solution composition] Formalin 10.0 ml Add water 1 As is clear from the results in Table 4, Samples 20 to 29 prepared using the coupler of the present invention are all Comparative Samples 17 to 29.
It can be seen that the color development is superior to that of 19.

Claims (1)

[Claims] 1. A silver halide photographic light-sensitive material having at least one silver halide emulsion layer on a support, wherein at least one of the silver halide emulsion layers has the 2-position represented by the following general formula [I]. A silver halide photographic light-sensitive material containing at least one 1H-pyrazolo [1,5-b] [1,2,4] triazole-based magenta coupler substituted with a group. General formula [I] [Wherein R ₁ , R ₂ and R ₃ each represent a substituent, m
Represents an integer of 0 to 3. When m is 2 or more, R ₃ may be the same or different. ]