JPS63256952A - Silver halide photographic sensitive material having good spectral absorption characteristics of formed color matter - Google Patents

Abstract

PURPOSE:To improve the color reproducibility of the titled material by incorpo rating at least one of a specified yellow coupler and at least one of a specified compd. in at least one layer of a silver halide emulsion layer. CONSTITUTION:At least one of the yellow coupler shown by formula I and at least one of the compd. shown by formula II are incorporated in at least one layer of the silver halide emulsion layer. In formulas I and II, R1 is halogen atom. or alkoxy group, R2 is hydrogen atom. or a group capable of substituting to a benzene ring, R3 is a monovalent org. residual group, Z1 is a group capable of releasing by a reaction with the oxidant of a color developing main agent, R<1>-R<3> are each an aliphatic or an aromatic group, (l)-(n) are each 0 or 1. Thus, the titled material having the improved color reproducibility is obtd.

Description

Detailed Description of the Invention [Industrial Field of Application] The present invention is directed to silver halide, which has good spectral absorption characteristics of the dye formed, excellent color reproducibility, excellent image storage stability, and high maximum density. It relates to photographic materials.

[Background of the Invention] In silver halide photographic materials used for direct viewing, such as color photographic paper, a combination of yellow coupler, magenta coupler and cyan coupler is usually used as a coloring agent to form a dye image. used. For these couplers, the color reproducibility in the resulting dye image,
Basic performances such as color development and image storage stability are required, but in recent years there has been an increasing demand from users for improved color reproducibility in order to faithfully reproduce the original colors of objects.

For example, in the case of a yellow coupler, unnecessary absorption on the long wavelength side of 500 nm or more is not sharply reduced to zero for the coloring dye formed, so it has the disadvantage that color reproduction in yellow and green hues is insufficient. was.

On the other hand, with the progress of silver halide photographic light-sensitive materials, there has been a demand for improved color development in recent years, and for this purpose, for yellow couplers, careful consideration has been made in the design of coupler molecules. It has been proposed to improve color development by introducing hydrophilic groups such as alkoxycarbonyl groups, sulfonyl groups, N-substituted or unsubstituted alkylsulfonamide groups, and arylsulfonamide groups into components.

However, when such a hydrophilic group is introduced into the ballast component of a yellow coupler, color development is generally improved, but unnecessary absorption of the long wavelength side of the color development dye further increases, and color reproducibility tends to deteriorate. . Therefore, the reality is that a silver halide photographic material that is excellent in both color development and color reproducibility has not yet been found.

[Object of the Invention] The first object of the present invention is to provide a silver halide photographic material with improved color reproducibility that forms a yellow dye image of excellent hue in which absorption on the long wavelength side sharply decreases to zero. It is about providing.

A second object of the present invention is to provide a silver halide photographic material with excellent preservability of yellow dye images.

A third object of the present invention is to provide a silver halide photographic material that has high color density and can provide a sufficient maximum density.

"Structure of the Invention: The above objects of the present invention are 1. In a silver halide photographic light-sensitive material having at least one silver halide emulsion layer on a support, at least one of the silver halide emulsion layers,
This is achieved by a silver halide photographic material containing at least one yellow coupler represented by the following general formula [Y-II] and at least one compound represented by the following general formula [II].

General formula [Y-II In the formula, R1 represents a halogen atom or an alkoxy group, and R
2 represents a hydrogen atom or a group that can be substituted on the benzene ring, and R
3 represents a monovalent organic residue, and Zl represents a group capable of reacting with an oxidized color developing agent and leaving it.

General formula [■coR+-(0), v-P-(0)rR2 (0), -R3 In the formula, R+, R2 and R3 each represent an aliphatic group or an aromatic group, and l, m and n are O or 1 respectively
represents. However, l, m and n are never 1 at the same time.

[Specific Structure of the Invention] In the above general formula [Y-II, R1 represents a halogen atom or an alkoxy group. The alkoxy group represented by R1 includes those having a substituent, such as a halogen atom, an aryl group, an alkoxy group, an aryloxy group, an alkylsulfonyl group, an acylamino group, an alkoxycarbonyl group, and an aryloxy group. Examples include carbonyl group, acyloxy group, acyl group, and hydroxy group.

R1 is preferably a chlorine atom or an alkoxy group.

In the general formula [1-II, R2 represents a hydrogen atom or a group capable of substituting on the benzene ring. Groups that can be substituted on the benzene ring represented by R2 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, an arylsulfonamide group, Examples include sulfamoyl group and imide group.

R2 is preferably a hydrogen atom.

In the general formula [Y-I], the monovalent organic residue represented by R3 includes the well-known valances 1 to 1 in yellow couplers.
groups, such as acylamino groups, alkoxycarbonyl groups,
Aryloxycarbonyl group, alkylsulfamoyl group, arylsulfamoyl group, alkylsulfonamide group, arylsulfonamide group, alkylureido group, arylureido group, succinimide group, alkoxy group, aryloxy group, alkylcarbamoyl group, aryl Examples include a carbamoyl group, an alkylsulfamoylamino group, an arylsulfamoylamino group, an alkyl group, an alkenyl group, an acyl group, and an acyloxy group.

In the general formula [1-I], Zl represents a group that can react with the oxidized product of the color developing agent and leave, for example, a group represented by the following general formula [Y-II] or [Y-I]. be.

-OR+ [Y II] General formula [1-
IF], R4 represents an aryl group or a heterocyclic group including those having substituents.

-NpaZ 2 CY -'II ]ゝ, -
- In the general formula [Y-I[[], Z2 does not represent a nonmetallic atomic group necessary to form a 5- to 6-membered ring in cooperation with the nitrogen atom. The atomic groups necessary to form the nonmetallic atomic group include, for example, methylene, methine, substituted methine, 7C
=0, -N) (-1-N=, -0-1-S-1-8O2
- etc.

The yellow coupler represented by the general formula [Y-I] is R
They may be bonded at 1, R2, R3 or 71 moieties to form a bis or higher multimer.

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

General formula [Y-IV] General formula [Y-Vl In general formula [Y-IV], X is an alkylene group,
Arylene group, alkylenearylene group, arylenealkylene group, or -A-V1 B- (A and B each represent an alkylene group, arylene group, alkylenearylene group, or arylenealkylene group, and vl represents a divalent linking group.) , and Y represents an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group. Z3 represents a group that can be separated upon coupling with the oxidized form of the developing agent.

In the general formula [Y-IV], examples of the alkylene group represented by Those substituted with alkyl groups, 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, such as 2-phenyl-ethylene group, 3-naphthyl-propylene group, etc.

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

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

The alkylene group, arylene group, alkylenearylene group, or arylenealkylene group represented by A and B are the same as the alkylene group, arylene group, alkylenearylene group, and arylenealkylene group represented by X in the general formula [Y-IV]. As a divalent linking group represented by vl, -〇-1-S-1-CO-1
Examples include groups such as -COO-1-OCO-1-NGO-1-5O2-. 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 - EV ], examples of the alkyl group represented by Y include ethyl group, butyl group, hexyl group, octyl group, dodecyl group, hexadecyl group, octadecyl group, etc. It may be straight chain or branched. Examples of the cycloalkyl group include a cyclohexyl group. 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. These alkyl groups, cycloalkyl groups, aryl groups, and heterocyclic groups represented by Y include those having further substituents.

Substituents are not particularly limited, but include carboxyl groups, ester groups, acyl groups, alkylsulfonyl groups, arylsulfonyl groups, hydroxy groups, or the above R
Groups similar to the group represented by 2 can be mentioned.

In the general formula [Y-IV], Z3 is a coupling-off group, but preferably in the general formula [Y-IV], Z3 is a coupling-off group.
Vl] to [Y-XI].

In the general formula [Y-Vl], RG 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 R2 above, and p is 1 to Represents an integer of 5. When p is 2 or more, R6 may be the same or different.

[Y-■] [Y-■] [Y-IX] General formula [Y-Vl], [Y-■] and [Y-Iχ]
, R7 and R8 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, an amine group, an acylamino group, an alkylsulfonyl group, an arylsulfonyl group,
Alkylsulfinyl group, arylsulfinyl group, alkylsulfonamide group, arylsulfonamide group,
Represents a carboxylic acid group, and these groups may be the same or different. Furthermore, R7 and R8 may form a ring.

[Y-X], [Y-XI] general formula [Y-
X] and [Y-XI, Z4 and Z5 represent heteroatoms, and Rs, R, to, and R++ represent the same groups as R7 and R8 above.

R12 represents an alkyl group, an aryl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group.

゛・Z≦′ In the general formula [Y-XI], W represents a hetero atom (for example, -Nl-1-1-N-1-〇-1-8-, etc.), a sulfonyl group, a carbonyl group, or a child. , Z6 is -W-
Represents a group of nonmetallic atoms necessary to form a 5- to 6-membered ring in cooperation with N-〇〇-.

Rj3, Rh, and R15 represent the general formula [Y-vl]
, [Y-Vl] OJ=hi [Y-IX] k Niokel R
7 and represents a group similar to R8. Further, R13, RHL and R15 may form a ring together with a part of Z6.

The yellow coupler represented by the general formula [''1-IV] may be bonded through Z3 or a ballast group to form a bis or higher polymorph.

In the general formula [Y-Vl, R5 represents an alkyl group.

The alkyl group represented by R5 may be linear or branched,
Examples include methyl group, ethyl group, isopropyl group, butyl group, t-amyl group, and dodecyl group. Also, R5
The alkyl group represented by may further have a substituent,
Examples of the substituent for R5 include the same groups as the substituent for R1 in the general formula [Y-I].

In the general formula [Y-Vl, R3 is the general formula [Y-■
Represents the same group as R3 in .

In the general formula [Y-Vl, Z3 is the general formula [Y-T
V], and is preferably a group represented by the general formula [Y-vI] to [Y-X■].

The yellow coupler represented by the general formula [Y-Vl is R3,
They may be bonded at R5 or 73 to form a bis or higher polymorph.

Next, typical specific examples of the yellow coupler represented by the general formula ['l-I] used in the present invention (hereinafter referred to as the yellow coupler of the present invention) are shown, but the present invention is not limited by these. isn't it.

Y-81 Furthermore, the yellow coupler of the present invention is disclosed in JP-A-55-70
Pages 4 to 8 of specification No. 841, and patent application No. 61-2
It also includes the exemplified compounds described on pages 20 to 26 of Specification No. 69216.

The yellow coupler of the present invention is, for example, disclosed in Japanese Patent Application Laid-Open No. 51-155.
No. 538, No. 61-6652, No. 55-70841, No. 47-24321, No. 48-66834, Japanese Patent Publication No. 19031/1983, and Japanese Patent Application No. 2692/1983
It can be easily synthesized according to the methods described in each publication of No. 6 and the like.

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 0 per mole of silver halide.
．． It is used in an amount of 0.2 to 1 mol, preferably 0.05 to 0.75 mol.

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

Examples of aliphatic groups represented by R1, R2 and R3 include alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, and cycloalkenyl groups having 1 to 32 carbon atoms. The alkyl group, alkenyl group and alkynyl group may be linear or branched. Moreover, these aliphatic groups also include those having substituents.

Examples of the aromatic group represented by Rj, R2 and R3 include an aryl group (eg, phenyl group, etc.), an aromatic heterocyclic group (eg, pyridyl group, furyl group, etc.). Moreover, these aromatic groups also include those having substituents.

Rj, R2 and R3 are preferably each an alkyl group or an aryl group, R1, R2 and R3 may each be the same or different, R,+.

The total number of carbon atoms in R2 and R3 is preferably 6 to 5.
It is 0.

Substituents for the aliphatic or aromatic groups represented by R4, R2 and R3 are not particularly limited, but are preferably alkoxy groups, aryloxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, aryloxycarbonyl groups, Examples include carbamoyl group, sulfamoyl group, acylamino group, and amino group.

1, m and n each represent 0 or 1, but 1, m
and n are never 1 at the same time. That is, R1
, R2 and R3 and at least one phosphorus atom is directly bonded to the aliphatic group or aromatic group.

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

I-314 1-81c) Heat C2Hs ■-141-15 1'-161-17 1,181-19 ■-20 (n-cgH+3okP=0 ■ i C1Hy C2Hs l-22 I-23 1-28I -29 ■ -30 ■ C2Hs I -311-32 I-351-36 ', 53 ■-38 ■-39 ■-40 (n C<HsO) (C2HsO) P=0n-Cl2
H2S ■-43 ■-44 ■-45 ■-47 ■-48 to H2 H2CH2C0OC+oH21(n) ■-49 ■-50 ■-53 c, H+, (n) ■-54 CH2COOCH2CHC-H3(n)2H5 ( n CgH17+T-P 0CsH1t(n)■
-56 (n-C4H, +T-P-OC, H-(n) ■-58 (n-C1H, h-P QC, □H25(n) ■-5
9 ■-61 ■-62 (C2H33-r-P=○ (n-C,H
,+r-P=0(i-C4H,h-P=O(n-C5H
, → 了p=.

(n C-H+3h-P=O(n C5H17+r
P=0■-70 (n-C,H,CHCH2+5-P=0■2H5 ■-71 (n-C,,H2,+r P =O(i-C,oH2,
+r P =0(n C+2H2s+rP=O(n
C+4Hzs+rP=01-76
I-77J-801-81 ■-84 ■-85 (CzHsterP-C+2H2s(n) ■-87 Convex ■-90 ■-92 I-941-95 The compound of the present invention is disclosed in JP-A-56-19049. Book 4
Also includes compounds described on pages 5 to 5.

Although some of the compounds of the present invention are commercially available, for example, JP-A-56-19049: British Patent No. 6941
No. 772 specification: Journal of the American
Chemical Society, 1957, Volume 79.

Page 6524 [J, Am, Chem, Soc,
, 79°6524 (1957)]: Journal of Organic Chemistry, 1960
Year, Volume 25, Page 1000 [J, 0r(1, Che
M, 25.1000 (1960) J; Organic Synthesis, 4951, Volume 31.

Page 33 [Org, 5ynth, , 31, . 3
3 (1951)] and the like.

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

Some of the compounds of the present invention are described in JP-A-56-19049. However, since 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, The above-mentioned documents do not suggest anything about improving color reproducibility.

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 by 1q from the yellow coupler of the present invention to the shorter wavelength side, and reduces the absorption at longer wavelengths of 500 nm or more. As a result, the color reproducibility is greatly improved, the image storage stability of the yellow dye is improved, and the color development of the silver halide photographic light-sensitive material using the yellow coupler is improved, and the color development property is sufficiently high. It has been discovered that the highest concentration can be obtained, and such an effect has been 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 silver halide emulsion layer, and are particularly preferably contained in a blue-sensitive silver halide emulsion layer.

Hydrophobic compounds such as the yellow coupler of the present invention and the compound of the present invention can be added to silver halide photographic materials using various methods such as a solid dispersion method, a latex dispersion method, and an oil-in-water emulsion dispersion method. can. For example, in the oil-in-water emulsion dispersion method, a hydrophobic additive such as a yellow coupler is usually added to a high-boiling organic solvent with a boiling point of about 150°C or higher, and if necessary, a low-boiling point and/or water-soluble organic solvent is used in combination. After it is dissolved and emulsified and dispersed in a hydrophilic binder such as an aqueous gelatin solution using a surfactant, it may be 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, etc., but especially when applied to color photographic paper to be directly used for g-shogetsu. The effects of the invention are effectively exhibited.

The silver halide photographic material of the present invention, including this color photographic paper, may be one for monochrome use or one for multicolor use. In the case of multicolor silver halide photographic light-sensitive materials, in order to reuse subtractive colors, it is usually used as a photographic coupler.
It has a structure in which a silver halide emulsion layer containing yellow, magenta, and cyan couplers and a non-photosensitive layer are laminated on a support in an appropriate number and order of layers. The order may be changed as appropriate depending on the important performance and purpose of use.

Examples of magenta dye image-forming couplers that can be used in the present invention include 5-pyrazolones, pyrazoloazoles, pyrazolinobenzimidazoles, indacylons,
Cyanoacetyl 4-equivalent or 2-equivalent magenta dye image-forming couplers are mentioned, for example, U.S. Pat. 3.127.269
No. 3,311,476, No. 3.152.89
No. 6, No. 3,419,391@, No. 3.519.4
No. 29, No. 3,558,318, No. 3,684,
No. 514, No. 3,705.896, No. 3,888
, No. 680, No. 3.907.571, No. 3.92
No. 8.044, No. 3,930,861, No. 3.9
No. 30.816, No. 3.933.500, JP-A No. 4
No. 9-29639, No. 49-111631, No. 49-
No. 129538, No. 51-112341, No. 52-5
No. 8922, No. 55-62454, No. 55-1180
No. 34, No. 56-38643, No. 56-135841
No. 46-60479, No. 52-34937, No. 55-29421, No. 55-35696, British Patent No. 1,247,493, Belgian Patent No. 792
．． No. 525 and West German Patent No. 2.156.111.

Cyan couplers that can be used in the present invention include:
Phenol compounds, naphthol compounds, etc. can be used. A specific example is U.S. Patent No. 2.3.
No. 69.929, No. 2,434,272, No. 2.
No. 474.293, No. 2,521,908, No. 2
, 895.826, 3.034.892, 3,311,476, 3,458,315, 3,476.563, 3,583.971 ,
No. 3,591,383, No. 3,767.411, No. 4,004,929, West German Patent No. 1a (OLS
) 2,414.830, 2,454,329, JP-A No. 48-59838, JP-A No. 51-26034, JP-A No. 51-26034,
No. 48-5055, No. 51-146828, No. 52
Examples thereof include those described in No. -69624 and No. 52-90932.

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) includes silver bromide, silver iodobromide, silver iodochloride, etc. Any of those used in conventional silver halide emulsions can be used, such as silver chloride, silver chlorobromide, and silver chloride.

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

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

The silver halide photographic material of the present invention includes a color antifoggant, a hardening agent, a plasticizer, a polymer latex, an ultraviolet absorber, a formalin scavenger 1 mordant, a development accelerator,
Development retardants, optical brighteners, matting agents, lubricants, antistatic agents, surfactants, and the like can be optionally used.

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

[Specific Effects of the Invention] In the silver halide photographic 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, and as a result, Color reproducibility can be significantly improved. Furthermore, the image storage stability of the yellow dye can be improved, and the coloring property is also high and a sufficient maximum density can be obtained.

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

Example-1 (Preparation of silver halide emulsion) By neutral method and simultaneous mixing method, six types shown in Table-1 Table-1 *1 2 mg added per mole of silver halide *2 5X10 per mole of silver halide -5 mol addition amount 3 0.9 mmol added per 1 mol of silver halide *4 0.7 mmol added per 1 mol of silver halide *5 0.2 mmol added per 1 mol of silver halide Each silver halide emulsion is After chemical sensitization, add 5TB as an emulsion stabilizer (not shown below)
-1 was added in an amount of 5.times.10@-3 moles per mole of silver halide.

S O2N H (C2Hs ) y [5D-3] (Preparation of silver halide color photographic light-sensitive material sample) Next, the following layers 1 to 7 were sequentially coated on a paper support whose both sides were coated with polyethylene (simultaneous coating). Silver halide color photographic materials 1 to 33 were prepared. (In the following examples, the amount added is shown as the amount per 112 of the photosensitive material.) Layer 1: Gelatin (1,2o) and 0.29(
] (in terms of silver, the same applies hereinafter) blue-sensitive silver halide emulsion (EIIl-1), 1.0 mmol of the yellow coupler shown in Table 2, 0.3 g of light stabilizer 5T-1, and 0.3 g of light stabilizer 5T-1.
015 g of 2,5-dioctylhydroquinone (HQ-
A layer containing 0.3 g of a compound of the present invention or a comparative compound shown in Table 2 in which 1) is dissolved.

Layer 2...Gelatin (0,h) and 0.041;
A layer containing 0.2 g of DOP (dioctyl phthalate) in which 1 of HQ-1 was dissolved.

Layer 3...Gelatin (1,4(+) and 0.2g
Green-sensitive silver halide emulsion (Em-2> and o, 5gg
of magenta coupler (M-1), 0.25 g of light stabilizer 5T-2 and oig of HQ-1 dissolved in
Filter dye Al-1 below with a DOP of 30 and 6m(I)
A layer containing.

Layer 4... Gelatin (1,20) and the following 0.6
g of ultraviolet absorber UV-1 and 0.05 (1 (7) H
A layer containing 0.39 DNP dissolved in Q-1.

Layer 5...Gelatin (1,4(1) and 0.20(
1 red-sensitive silver halide emulsion (Em-3> and 0.5
Cyan coupler (C-1) of 4(l), 0.01(l of 1
-IQ-1 and 0.3g) S Ding-1wom resolution 0.3
! ] (7) A layer containing DOP.

Layer 6...Gelatin (1,1(1) and 0.2(l)
A layer containing 0,20 DOP in which UV-1 of 100% was dissolved and 51H of the following filter dye F31AI-2.

Layer 7...Gelatin (1,0(1) and O,o5
g of 2゜4-dichloro-6-hydroxytriazine (ST-1) UV-1 l-1 The obtained sample was subjected to wedge exposure using a sensitometer KS-7 model (manufactured by Konishiroku Photo Industry Co., Ltd.). After processing according to the following color development process, the maximum density (DmaX) of the blue-sensitive emulsion layer was measured using an optical densitometer (Model PDA-65, manufactured by Konishi Roku Photo Industry Co., Ltd.).

Further, the maximum absorption wavelength λmax when the density of the yellow dye image was 1.0, and the density and DG at a wavelength of 500 nm at that time were measured.

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

Further, the specific sensitivity was expressed as a relative value with the sensitivity of sample N001 being 100.

The results are shown in Table-2.

[Processing process] Temperature Time Development color development 34.7±0.3℃ 45 seconds Bleach fixing 34.7±0.5℃ 50 seconds stabilization 3
0~34℃ 90 seconds Reprint Drying 60~
80°C 60 seconds [Color developer] Pure water 800ml Triethanolamine 8g N, N-diethylhydroxyamine 5g Potassium chloride
2g N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-amine aniline sulfate 5g sodium tetrapolyphosphate 2g potassium carbonate
300 potassium sulfite
0.2g Fluorescent brightener (4,4'-diaminostilbendisulfonic acid derivative) 1g Add pure water to bring the total amount to 11, and adjust to 1) H10.2.

[Bleach-fix solution] Ethylenediaminetetraacetic acid ferric ammonium dihydrate 600 Ethylenediaminetetraacetic acid 3g Ammonium Naosulfate (10% solution) 1oo-Ammonium sulfite (40% solution) 27.5d Adjust to pH 5.7 with potassium carbonate or glacial acetic acid Add water and answer all questions! shall be.

[Stabilizing solution 1 5-chloro-2-methyl-4-isothiazolin-3-one 1g 1-hydroxyethylidene-1,1-diphosphonic acid 2g Add water to make 11, and add 1) H with sulfuric acid or potassium hydroxide. 7.
Adjust to 0.

As is clear from Table 2, samples No. 3 to 7 using the yellow coupler of the present invention and the compound of the present invention. N
o, 10 to 14 and No. 17 to 21 are comparative samples No. 0, which do not contain the compound of the present invention, corresponding to the respective sample groups.
21-2. No. 8-9 and No.

Compared to 15-16, both the maximum density and sensitivity were high (and the color development was excellent. Also, the maximum absorption wavelength was shifted slightly to the short wavelength side and DG was reduced, so it had excellent color reproducibility and light resistance. An improvement was also seen.

Among these, in particular, the general formulas [Y -IV ] and [
Sample No. 10 to No. 1 using a more preferable yellow coupler of the present invention represented by Y-V] and a compound of the present invention
, 14 and No. 17 to No. 21 have a large increase in maximum concentration and sensitivity, and a large decrease in DG compared to the comparative samples that do not contain the compound of the present invention, and are also found to have excellent improvement effects. Understood.

Furthermore, samples No. 22 to 336 using the yellow coupler of the present invention and the compound of the present invention were found to be silver halide photographic materials excellent in color development, color reproducibility, and light resistance.

Example'-2 The blue-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-sensitive silver halide emulsion of Layer 3 was added to Em- in Table 1.
5, the red-sensitive silver halide emulsion of layer 5 was added to Em of Table 1.
Silver halide color photographic light-sensitive materials No. 0.34 to 66 were prepared in the same manner as in Example 1 except that the yellow couplers shown in Table 3 and the compounds of the present invention or comparative compounds were used in layer 1 in place of each of the compounds No. 6 and No. 6. was created.

The obtained sample was passed through a photosensitive needle KS-7 type (manufactured by Konishiroku Photo Industry).
After wedge exposure using the following color development process, the same measurements as in Example 1 were carried out.

The results are shown in Table-3.

[Processing process] Time Temperature Repellent color development 3 minutes 30 seconds 33°C Bleach fixing 1 minute 30 seconds 33°C Water washing 3 minutes 33°C [Color developer] N-ethyl-N-β-methanesulfonamidoethyl-3- Methyl-4-amine aniline sulfate 4,9g Hydroxylamine sulfate 2,0g Potassium carbonate
25.0 (sodium monobromide
0.6g anhydrous sodium sulfite
2.0g benzyl alcohol
131g polyethylene glycol (average degree of polymerization 400) 3.01e
Add water to make 11, add sodium hydroxide to p+-+10
．． Adjust to 0.

[Bleach-fix solution] Ethylenediaminetetraacetic acid sodium salt 6.0g Ammonium thiosulfate 100g Sodium bisulfite 10979 Sodium bisulfite
3 g of water was added to adjust the temperature to 11°C, and the pH was adjusted to 7.0 with ammonia water.As is clear from the results in Table 3, the maximum absorption wavelength of the sample of the present invention was also found in this example, compared to samples other than the sample of the present invention. It was found that the silver halide photographic material shifted to the short wavelength side, resulting in a small DG, excellent color reproducibility, high maximum density and sensitivity, and improved light resistance.

By the way, in this example, a developer containing pencil alcohol as a color development accelerator, which is commonly used in the past, was used as a color developer.

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

Claims (1)

[Scope of Claims] In a silver halide photographic material having at least one silver halide emulsion layer on a support, at least one of the silver halide emulsion layers has the following general formula [Y-I]
A silver halide photographic light-sensitive material comprising at least one yellow coupler represented by the following formula [I] and at least one compound represented by the following general formula [I]. General formula [Y-I] ▲ Numerical formulas, chemical formulas, tables, etc. represents an organic residue, and Z_1 represents a group capable of reacting with and leaving an oxidized form of a color developing agent. ] General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R^1, R^2 and R^3 each represent an aliphatic group or an aromatic group, and l, m and n are each 0 Or represents 1. However, l, m and n are never 1 at the same time. ]