JPH0758388B2 - A silver halide photographic light-sensitive material in which the formed dye has good spectral absorption characteristics. - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial field of application] The present invention relates to a silver halide capable of obtaining a high maximum density with excellent spectral absorption characteristics of the dye formed, excellent color reproducibility, and excellent image storability. The present invention relates to a photographic light-sensitive material.

BACKGROUND OF THE INVENTION In a silver halide photographic light-sensitive material that is directly provided for viewing, such as color photographic paper, a combination of a yellow coupler, a magenta coupler and a cyan coupler is usually used as a color forming agent for forming a dye image. Used. For these couplers, the color reproducibility in the dye image obtained,
Basic properties such as color developability and image storability are required, and in recent years, in particular, there has been an increasing demand from users for improved color reproducibility in order to faithfully reproduce the original color of an object.

For example, in the case of a yellow coupler, the unnecessary absorption on the long wavelength side of 500 nm or more does not sharply decrease to zero with respect to the formed coloring dye, and thus has the drawback that the color reproduction in the yellow and green hues is insufficient. Was there.

On the other hand, with the progress of silver halide photographic light-sensitive materials, it has been required in recent years to improve the color developability. For this purpose, various studies have been attempted in designing the coupler molecule in the yellow coupler, for example, ballast. It has been proposed to introduce a hydrophilic group such as an alkoxycarbonyl group, a sulfonyl group, an N-substituted or unsubstituted alkylsulfonamide group or an arylsulfonamide group into a component to improve the color developability.

However, when such a hydrophilic group is introduced into the ballast component of the yellow coupler, the color developability is generally improved, but unnecessary absorption on the long wavelength side of the color forming dye is further increased, and the color reproducibility tends to be deteriorated. . Therefore, the reality is that no silver halide photographic light-sensitive material excellent in both color developability and color reproducibility has been found yet.

[Object of the Invention] A first object of the present invention is to provide a silver halide photographic light-sensitive material having improved color reproducibility for forming a yellow dye image having an excellent hue in which absorption on the long wavelength side is sharply reduced to zero. To provide.

A second object of the present invention is to provide a silver halide photographic light-sensitive material excellent in storability of a yellow dye image.

A third object of the present invention is to provide a silver halide photographic light-sensitive material having a high color density and a sufficient maximum density.

[Constitution of 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 has the following general formula [Y -I] and a silver halide photographic light-sensitive material containing at least one yellow coupler and at least one compound represented by the following general formula [I].

General formula [Y-I] In the formula, R ₁ represents a halogen atom or an alkoxy group, R ₂ represents a hydrogen atom or a group capable of substituting for a benzene ring, and R ₃ represents 1
Represents a valent organic residue, and Z ₁ represents a group capable of leaving by reacting with an oxidized product of a color developing agent.

General formula [I] [In the formula, R ¹ , R ² and R ³ each represent an aliphatic group or an aromatic group. [Specific Configuration of the Invention] In the general formula [Y-I], R ₁ represents a halogen atom or an alkoxy group. The alkoxy group represented by R ₁ also includes those having a substituent, and examples of such a substituent include a halogen atom, an aryl group, an alkoxy group, an aryloxy group, an alkylsulfonyl group, an acylamino group, an alkoxycarbonyl group and an aryl group. An oxycarbonyl group,
Examples thereof include an acyloxy group, an acyl group and a hydroxy group.

R ₁ is preferably a chlorine atom or an alkoxy group.

In the general formula [Y-I], R ₂ represents a hydrogen atom or a group capable of substituting on the benzene ring. Examples of the group capable of substituting the benzene ring represented by R ₂ include a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an acylamino group, a carbamoyl group, an alkylsulfonamide group, and an arylsulfonamide group. , Sulfamoyl group, imide group and the like.

R ₂ is preferably a hydrogen atom.

In the general formula [Y-I], the monovalent organic residue represented by R ₃ is a ballast group known in yellow couplers,
For example, an acylamino group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylsulfamoyl group,
Arylsulfamoyl group, alkylsulfonamide group, arylsulfonamide group, alkylureido group,
Examples include an arylureido group, a succinimide group, an alkoxy group, an aryloxy group, an alkylcarbamoyl group, an arylcarbamoyl group, an alkylsulfamoylamino group, an arylsulfamoylamino group, an alkyl group, an alkenyl group, an acyl group or an acyloxy group. To be

In the general formula [Y-I], Z ₁ represents a group capable of leaving by reacting with an oxidized product of a color developing agent. For example, a group represented by the following general formula [Y-II] or [Y-III]. Is.

—OR ₄ [Y-II] In the general formula [Y-II], R ₄ represents an aryl group or a heterocyclic group including those having a substituent.

In the general formula [Y-III], Z ₂ represents a group of nonmetallic atoms necessary for forming a 5- or 6-membered ring in cooperation with a nitrogen atom. Here, as the atomic group necessary for forming the non-metal atomic group, for example, methylene, methine, substituted methine, C =
O, -NH -, - N = , - O -, - S -, - SO 2 - , and the like.

The yellow coupler represented by the general formula [Y-I] is
The R ₁ , R ₂ , R ₃ or Z ₁ moieties may combine to form a bis or higher multimer.

Preferred yellow couplers of the present invention are represented by the following general formulas [Y-IV] and [YV].

General formula [Y-IV] General formula [YV] In the general formula [Y-IV], X is an alkylene group, an arylene group, an alkylenearylene group, an arylenealkylene group or -A-V ₁ -B- (A and B are an alkylene group, an arylene group, an alkylenearylene group or an arylene, respectively. Represents an alkylene group, V ₁ represents a divalent linking group), and Y represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group. Z ₃ represents a group capable of splitting off upon coupling with an oxidized product of a developing agent.

In the general formula [Y-IV], examples of the alkylene group represented by X include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group and the like, and a group having a substituent is also included. Substituted with a group such as methyl-methylene group, ethyl-ethylene group,
1-methyl-ethylene group, 1-methyl-2-ethyl-ethylene group, 2-decyl-ethylene group, 3-hexyl-propylene group, 1-benzyl-ethylene group, etc. and those substituted with an aryl group, for example, 2 -Phenyl-ethylene group, 3-naphthyl-propylene group and the like.

Examples of the arylene group include a phenylene group and a naphthylene group.

Examples of the alkylenearylene group include a methylenephenylene group and the like, and examples of the arylenealkylene group include a phenylenemethylene group and the like.

The alkylene group, arylene group, alkylenearylene group, or arylenealkylene group represented by A and B is the same as the alkylene group, arylene group, alkylenearylene group, and arylenealkylene group represented by X in the general formula [Y-IV]. And a divalent linking group represented by V ₁ is -O-, -S-, -CO-, -CO.
O-, -OCO-, A group such as —SO ₂ — is exemplified. Here, R and R'represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group, and R and R'may be the same or different.

X is preferably an alkylene group.

In the general formula [Y-IV], the alkyl group represented by Y is, for example, an ethyl group, a butyl group, a hexyl group,
Examples thereof include an octyl group, a dodecyl group, a hexadecyl group and an octadecyl group, and these alkyl groups may be linear or branched. Examples of the cycloalkyl group include a cyclohexyl group and the like. Examples of the aryl group include a phenyl group and a naphthyl group. Further, examples of the heterocyclic group include a pyridyl group and the like. The alkyl group, cycloalkyl group, aryl group and heterocyclic group represented by Y also include those further having a substituent.

The substituent is not particularly limited, but a carboxyl group, an ester group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy group or the above R ₂
A group similar to the group represented by can be mentioned.

In the general formula [Y-IV], Z ₃ is a coupling-off group, but preferably the following general formulas [Y-VI] to [Y-
XII].

In the general formula [Y-VI], R ₆ represents a carboxyl group, an ester group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy group or a substituent similar to the group represented by R ₂ , and p represents It represents an integer of 1 to 5. p is 2
In the above case, R ₆ may be the same or different.

In the general formulas [Y-VII], [Y-VIII] and [Y-IX], R ₇ and R ₈ are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, a heterocyclic group, a carboxylic acid ester. Group, amino group, acylamino group, alkylsulfonyl group, arylsulfonyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonamide group, arylsulfonamide group, carboxylic acid group, and these groups may be the same or different. May be. Further, R ₇ and R ₈ may form a ring.

In the general formula [Y-X] and _{[Y-XI], Z 4} , Z 5 represents a _{heteroatom, R 9, R 10, R} 11 represents the same group as the R ₇ and R _8.

R ₁₂ represents an alkyl group, an aryl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group.

In the general formula [Y-XII], W is a hetero atom (for example, -NH-, -N =, -O-, -S-, etc.), a sulfonyl group, a carbonyl group, or Represents a carbon atom, and Z ₆ is Represents a non-metal atomic group necessary for forming a 5- or 6-membered ring in cooperation with.

R ₁₃ , R ₁₄ and R ₁₅ are each represented by the general formula [Y-VII] or [Y-
VIII] and [Y-IX] represent the same groups as R ₇ and R ₈ . R ₁₃ , R ₁₄ and R ₁₅ may form a ring together with a part of Z ₆ .

The yellow coupler represented by the general formula [Y-IV] is Z ₃
Alternatively, they may be bonded with a ballast group to form a multimer of bis form or more.

In the general formula [YV], R ₅ represents an alkyl group. R ₅
The alkyl group represented by may be linear or branched and includes, for example, methyl group, ethyl group, isopropyl group, butyl group, t
-Amyl group, dodecyl group and the like. The alkyl group represented by R ₅ may further have a substituent, and examples of the substituent of R ₅ include the same groups as the substituents of R _{1 in} the general formula [YI]. You can

In the general formula [Y-V], R ₃ is the general formula [Y-I].
Represents a group similar to R _{3 in} .

In the general formula [Y-V], Z ₃ is the general formula [Y-IV].
Is a group similar to Z _{3 in,} and is preferably a group represented by the above general formula [Y-VI] to general formula [Y-XII].

The yellow coupler represented by the general formula [YV] is R ₃ , R ₅
Alternatively, they may combine with each other at Z ₃ to form a bis or higher multimer.

Next, typical specific examples of the yellow coupler represented by the general formula [Y-I] (hereinafter referred to as the yellow coupler of the present invention) used in the present invention are shown, but the present invention is not limited thereto. Absent.

Further, the yellow coupler of the present invention is disclosed in JP-A-55-70841.
The examples include the compounds described on pages 4 to 8 of the specification and pages 20 to 26 of Japanese Patent Application No. 61-269216.

The yellow coupler of the present invention is disclosed, for example, in JP-A-57-155538.
No. 61, No. 61-6652, No. 55-70841, No. 47-24321,
48-66834, Japanese Patent Publication No. 46-19031 and Japanese Patent Application No. 61-2692
It can be easily synthesized according to the method described in each publication of No. 16, etc.

The couplers of the present invention may be used alone or in combination of two or more.

The yellow coupler of the present invention has a content of 0.
It is used in an amount of 02 to 1 mol, preferably 0.05 to 0.75 mol.

Next, the compound represented by the above general formula [I] (hereinafter referred to as the compound of the present invention) will be described.

Examples of the aliphatic group represented by R ¹ , R ² and R ³ include an alkyl group having 1 to 32 carbon atoms, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group and the like. The alkyl group, alkenyl group and alkynyl group may be linear or branched. Further, these aliphatic groups also include those having a substituent.

Examples of the aromatic group represented by R ¹ , R ² and R ³ include an aryl group (eg, phenyl group) and an aromatic heterocyclic group (eg, pyridyl group, furyl group, etc.). Moreover, these aromatic groups also include those having a substituent.

R ¹ , R ² and R ³ are preferably each an alkyl group or an aryl group, R ¹ , R ² and R ³ may be the same or different, and R ¹ , R ² and R ³ are carbon atoms. The sum of the numbers is preferably 6-50.

The substituent of the aliphatic group or aromatic group represented by R ¹ , R ² and R ³ is not particularly limited, but is preferably an alkoxy group, an aryloxy group, an acyl group, an acyloxy group, an alkoxycarbonyl group, an aryloxy group. Carbonyl group,
Carbamoyl group, sulfamoyl group, acylamino group,
An amino group etc. are mentioned.

Typical examples of the compound of the present invention are shown below, but the present invention is not limited thereto.

I-1 I-2 (C ₂ H _{5 3} P = O (n-C ₄ H _{9 3} P = O I-3 I-4 (i-C ₄ H _{9 3} P = O (n-C ₅ H _{11 3} P = O I-5 I-6 (n-C ₆ H _{13 3} P = O (n-C ₈ H _{17 3} P = O I-9 I-10 (n-C ₁₀ H _{21 3} P = O (i-C ₁₀ H _{21 3} P = O I-11 I-12 (n-C ₁₂ H _{25 3} P = O (n-C ₁₄ H _{29 3} P = O I-13 (n-C ₁₇ H _{33 3} P = O The compounds of the present invention are disclosed in JP-A-56-19049, pp. 4-5.
It also includes the compounds described on the page.

Some of the compounds of the present invention are commercially available, for example, JP-A-56-19049; British Patent No. 694,772; Journal of the American Chemical Society, 1957, 79. Volume, p. 6524 [J. Am. Chem. So
c., 79 , 6524 (1957)]; Journal of Organic Chemistry, 1960, Volume 25, page 1000 [J.Org.C.
hem., 25 , 1000 (1960)]; Organic Synthesis, 1
951, Volume 31, Page 33 [Org.Synth., 31 , 33 (1951)]
And the like.

The amount of the compound of the present invention used is preferably 5 to 500 mol%, more preferably 10 to 300, relative to the yellow coupler of the present invention.
Mol%.

Some of the compounds of the present invention are described in JP-A-56-19049. However, the compound of the present invention shifts the maximum absorption wavelength of the yellow dye obtained from the yellow coupler represented by the general formula [Y-I] to the short wavelength side and sharply reduces the absorption on the long wavelength side to zero. There is no suggestion of improving the color reproducibility in the above literature.

That is, as a result of intensive research, the present inventors have found that the compound of the present invention shifts the maximum absorption wavelength of the yellow dye obtained from the yellow coupler of the present invention to the short-wave side.
Absorption on the long wavelength side of 0 nm or more is reduced, resulting in a significant improvement in color reproducibility, and improvement in image storability of the yellow dye, and further silver halide photographic light-sensitive material using the yellow coupler. It has been found that the coloring property of the material is improved and a sufficiently high maximum density is obtained, and such an effect is obtained for the first time by the present invention.

The yellow coupler of the present invention and the compound of the present invention are contained in at least one of the silver halide emulsion layers, and particularly preferably in the blue-sensitive silver halide emulsion layer.

The hydrophobic compound such as the yellow coupler of the present invention and the compound of the present invention can be added to the silver halide photographic light-sensitive material by various methods such as a solid dispersion method, a latex dispersion method and an oil-in-water emulsion dispersion method. it can. For example, the oil-in-water type emulsion dispersion method, a hydrophobic additive such as a yellow coupler is usually used in combination with a high-boiling point organic solvent having a boiling point of about 150 ° C. or higher, if necessary, a low-boiling point, and / or a water-soluble organic solvent. It may be dissolved, emulsified and dispersed in a hydrophilic binder such as an aqueous gelatin solution using a surfactant, and then added to the desired hydrophilic colloid layer.

The silver halide photographic light-sensitive material of the present invention can be applied to, for example, color negative and positive films, color photographic paper, and the like. In particular, the present invention is applied to a color photographic paper accompanied by direct viewing. The effect of is effectively exhibited.

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

Examples of the magenta dye image-forming coupler which can be used in the present invention include 5-pyrazolone type, pyrazoloazole type, pyrazolinopentimimidazole type, indazolone type and cyanoacetyl type 4 equivalent or 2 equivalent magenta dye image forming couplers. These are, for example, U.S. Patent Nos. 2,600,788, 3,061,432, and 3,062,65.
No. 3, No. 3,127,269, No. 3,311,476, No. 3,152,8
No. 96, No. 3,419,391, No. 3,519,429, No. 3,558,
No. 318, No. 3,684,514, No. 3,705,896, No. 3,88
No. 8,680, No. 3,907,571, No. 3,928,044, No. 3,9
30,861, No. 3,930,816, No. 3,933,500, JP Sho
49-29639, 49-111631, 49-129538, 51
-112341, 52-58922, 55-62454, 55-11
No. 8034, No. 56-38643, No. 56-135841, Japanese Patent Publication No. 46-6
0479, 52-34937, 55-29421, 55-35696
No., British Patent No. 1,247,493, Belgian Patent No. 792,525
And West German Patent 2,156,111.

The cyan coupler that can be used in the present invention,
Phenol compounds, naphthol compounds, etc. can be used. Specific examples thereof include U.S. Pat.
No. 929, No. 2,434,272, No. 2,474,293, No. 2,52
1,908, 2,895,826, 3,034,892, 3,3
No. 11,476, No. 3,458,315, No. 3,476,563, No. 3,
No. 583,971, No. 3,591,383, No. 3,767,411, No. 3
4,004,929, West German patent application (OLS) 2,414,830, 2,4
54,329, JP-A-48-59838, 51-26034, 48-
5055, 51-146828, 52-69624, 52-90932
The items described in No.

The silver halide emulsion used in the silver halide photographic light-sensitive material of the present invention (hereinafter referred to as the silver halide emulsion of the present invention).
As the silver halide, any of silver halides such as silver bromide, silver iodobromide, silver iodochloride, silver chlorobromide, and silver chloride used in ordinary silver halide emulsions can be used.

The silver halide emulsion of the present invention is chemically sensitized by a sulfur sensitizing method, a selenium sensitizing method, a reduction sensitizing method, a noble metal sensitizing method or the like.

The silver halide emulsion of 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 a color antifoggant, a hardener, a plasticizer, a polymer latex, an ultraviolet absorber, a formalin scavenger, a mordant, a development accelerator,
A development retarder, a fluorescent whitening agent, a matting agent, a lubricant, an antistatic agent, a surfactant and the like can be optionally used.

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

[Specific effects of the invention] In the silver halide photographic light-sensitive material of the present invention, by containing the yellow coupler of the present invention and the compound of the present invention, the spectral absorption characteristics of the yellow dye formed are improved. Color reproducibility can be significantly improved. Further, the image storability of the yellow dye can be improved, and the color development is high and a sufficient maximum density can be obtained.

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

Example-1 (Preparation of silver halide emulsion) Six types of silver halide emulsions shown in Table-1 were prepared by a neutral method and a simultaneous mixing method.

After the chemical sensitization, 5 × 10 ⁻³ mol of STB-1 shown below as an emulsion stabilizer was added to each silver halide emulsion per mol of silver halide.

(Preparation of silver halide color photographic light-sensitive material sample) Then, the following layers 1 to 7 were sequentially coated (simultaneous coating) on a paper support whose both surfaces were coated with polyethylene, and silver halide color photographic light-sensitive materials 1-33 Was produced. (In the following examples, the addition amount is shown per 1 m ² of the light-sensitive material.) Layer 1 ... Gelatin (1.2 g) and 0.29 g (in terms of silver, the same applies hereinafter) of a blue-sensitive silver halide emulsion. (Em-1) and 1.0 mmol of yellow coupler shown in Table-2, 0.3 g of light stabilizer
ST-1 and 0.015 g of 2,5-dioctylhydroquinone (H
A layer containing 0.3 g of the compound of the present invention or the comparative compound shown in Table 2 in which Q-1) is dissolved.

Layer 2 ... Gelatin (0.9 g) and 0.04 g of HQ-1 dissolved
A layer containing 0.2 g of DOP (dioctyl phthalate).

Layer 3: Gelatin (1.4 g), 0.2 g green light-sensitive silver halide emulsion (Em-2) and 0.50 g magenta coupler (M-
1), 0.25 g of light stabilizer ST-2 and 0.01 g of HQ-1 were dissolved. A layer containing 0.3 g DOP and 6 mg of the following filter dye AI-1.

Layer 4: Gelatin (1.2 g) and 0.6 g of the following UV absorber
A layer containing UV-1 and 0.3 g DNP dissolved in 0.05 g HQ-1.

Layer 5 ... Gelatin (1.4 g), 0.20 g of red-sensitive silver halide emulsion (Em-3), and 0.54 g of cyan coupler (C-
1), 0.3g with 0.01g HQ-1 and 0.3g ST-1 dissolved
The layer containing the DOP and.

Layer 6 ... Gelatin (1.1 g) and 0.2 g UV-1 dissolved.
A layer containing 2 g of DOP and 5 mg of the following filter dye AI-2.

Layer 7 ... Gelatin (1.0 g) and 0.05 g of 2,4-dichloro-
A layer containing sodium 6-hydroxytriazine.

The obtained sample is a sensitometer KS-7 type (made by Konishi Rokusha Kogyo Co., Ltd.)
After exposure to a wedge using the above, and after processing according to the following color development processing step, using an optical densitometer (PDA-65 type manufactured by Konishi Rokusha Kogyo Co., Ltd.), the maximum density (Dma
x) was measured.

Further, the maximum absorption wavelength λmax when the density of the yellow dye image is 1.0, and the density at the wavelength of 500 nm at that time,
D _G was measured.

Further, the obtained sample was subjected to a fading test for 10 days with a fade meter, and the light resistance was evaluated by determining the residual ratio (%) of the dye image at an initial density of 1.0.

The specific sensitivity is shown as a relative value with the sensitivity of Sample No. 1 being 100.

The results are shown in Table-2.

[Processing process] Temperature Time Color development 34.7 ± 0.3 ℃ 45 seconds Bleach fixing 34.7 ± 0.5 ℃ 50 seconds Stabilization 30 to 34 ℃ 90 seconds Dry 60 to 80 ℃ 60 seconds [Color developer] Pure water 800 ml Tri Ethanolamine 8 g N, N-diethylhydroxyamine 5 g Potassium chloride 2 g N-ethyl-N-β-methanesulfonamide ethyl-3
-Methyl-4-aminoaniline sulfate 5 g Sodium tetrapolyphosphate 2 g Potassium carbonate 30 g Potassium sulfite 0.2 g Optical brightener (4,4'-diaminostilbene disulfonic acid derivative) 1 g Set to 1 and adjust to pH 10.2.

[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 5.7 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 g 1-hydroxyethylidene-1,1-diphosphonic acid 2 g Water was added to 1 to adjust the pH with sulfuric acid or potassium hydroxide.
Adjust to 7.0.

As is clear from Table 2, sample Nos. 3, 7, 10, 14, 17 using the yellow coupler of the present invention and the compound of the present invention.
And 21 are comparative samples No. 1-2, No. 8-9 and No. 15-16 which do not contain the compound of the present invention corresponding to each sample group.
The maximum density and sensitivity were higher than those of, and the color development was excellent. In addition, the maximum absorption wavelength was shifted to the short-wave side and the D _G was decreased, resulting in excellent color reproducibility and improved light resistance.

Furthermore, Sample Nos. 4-6, 11-13, 18-using the yellow coupler of the present invention and the comparative compounds A-N other than the present invention
20, 22 to 24, 26 and 27 are slightly inferior in maximum density and sensitivity as compared with the sample of the present invention. Also, the maximum absorption wavelength is slightly shifted to the short wavelength side, and DG is decreased, so that the color reproducibility is slightly inferior.

Among them, especially, the above general formulas [Y-IV] and [Y-
V], more preferred yellow couplers of the present invention represented by the formula [V], and samples No. 10 to No. 14 and N using the compounds of the present invention.
It was found that o.17 to No. 21 were large in maximum concentration, increase in sensitivity, and decrease in D _G , and further excellent in improvement effect, as compared with the comparative sample containing no compound of the present invention. .

Further, it was found that Sample Nos. 25 and 28 to 33 using the yellow coupler of the present invention and the compound of the present invention are also silver halide photographic light-sensitive materials excellent in color developability, color reproducibility and light resistance. .

Example-2 The blue light-sensitive silver halide emulsion of Layer 1 of the silver halide color photographic light-sensitive material prepared in Example-1 was used as Em-4 in Table-1.
The green light-sensitive silver halide emulsion of Layer 3 was added to Em-5 of Table-1.
And the red-sensitive silver halide emulsion of Layer 5 was used as Em-6 in Table-1.
In place of the yellow couplers shown in Table 3 and the compound of the present invention or the comparative compound in Layer 1, silver halide color photographic materials No. 34 to 66 were prepared in the same manner as in Example 1. did.

The obtained sample was subjected to wedge exposure using a sensitometer KS-7 type (manufactured by Konishi Rokusha Kogyo Co., Ltd.) and then processed according to the following color development processing step, and then the same measurement as in Example-1 was performed.

The results are shown in Table-3.

[Treatment process] Time Temperature Color development 3 minutes 30 seconds 33 ° C Bleach fixing 1 minute 30 seconds 33 ° C Water wash 3 minutes 33 ° C [Color developer] N-ethyl-N-β-methanesulfonamidoethyl-3
-Methyl-4-aminoaniline sulfate 4.9 g Hydroxylamine sulfate 2.0 g Potassium carbonate 25.0 g Sodium bromide 0.6 g Anhydrous sodium sulfite 2.0 g Benzyl alcohol 13 ml Polyethylene glycol (average degree of polymerization 400) 3.0 ml Add water 1 And adjust the pH to 10.0 with sodium hydroxide.

[Bleach fixer] Ethylenediaminetetraacetic acid iron sodium salt 6.0 g Ammonium thiosulfate 100 g Sodium bisulfite 10 g Sodium metabisulfite 3 g Water is added to adjust the pH to 1 with ammonia water.

As is clear from the results of Table 3, in the present example, the sample of the present invention also has a maximum absorption wavelength shifted to the short wave side as compared with the sample other than the present invention, and as a result, D _G becomes smaller and color reproduction is reduced. It was found that the silver halide photographic light-sensitive material has excellent properties, high maximum density and sensitivity, and improved light resistance.

By the way, in this embodiment, as the color developing solution, a developing solution containing benzyl alcohol as a color developing accelerator which has been frequently used conventionally was used.

From the results of this example, it can be seen that the present invention has sufficient effects even in such a system.

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 is represented by the following general formula [Y-1]. At least one yellow coupler
And a compound represented by the following general formula [I], and a silver halide photographic light-sensitive material. General formula [Y-1] [Wherein R ₁ represents a halogen atom or an alkoxy group, R ₂ represents a hydrogen atom or a group capable of substituting for a benzene ring, and R ₃ represents 1
Represents a valent organic residue, and Z ₁ represents a group capable of leaving by reacting with an oxidized product of a color developing agent. ] General formula [I] [In the formula, R ¹ , R ² and R ³ each represent an aliphatic group or an aromatic group. ]