JPS63167357A - Silver halide photographic sensitive material having good spectral absorption characteristics of formed dye - Google Patents

Abstract

PURPOSE:To form a Magenta dye picture image having superior hue and to improve the color reproducibility by incorporating each specified magenta coupler and a compound into at least one layer of silver halide emulsion. CONSTITUTION:One of the Magenta couplers expressed by the for mula [I] and one of the compound expressed by the formula [II] are incorporated into at least a layer of a silver halide emulsion. In the formula [I], Z is nonmetal atom group necessary for the formation of a N-contg. heterocyclic ring; X is a H atom or a group being releasable of the reaction with an oxidized body of a color developing agent; R is a H atom or a substituent. In the formula [II], each R<1> and R<2> is aliphatic group or -COR' (R' is aliphatic group); J is a divalent org. group r a simple joint bond; (l) is an integer 0-6. By this constitution, the spectral absorption characteristics of Magenta dye are improved, and the color reproducibility is improved remarkably, and the preservability for picture image for the Magenta dye is also improved. Thus, a photographic sensitive sensitive material having high color developing property and sufficient maximum density are obtd.

Description

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

[Background of the Invention] In color photographic papers intended for direct viewing, a combination of a yellow coupler, a magenta coupler, and a cyan coupler is usually used. Among these, pyrazoloazole couplers have recently been developed as magenta couplers.

Pyrazoloazole couplers are conventionally used 5
- Unlike pyrazolone magenta couplers, the coloring dye does not have nj absorption near 430no+, so it is basically advantageous for color reproducibility, but the maximum absorption wavelength of the coloring dye is 5 - They generally have longer wavelengths than pyrazolone-based magenta couplers, and have the disadvantage that absorption on the long wavelength side of 600 rv or more does not sharply decrease to zero.

Furthermore, magenta dyes obtained from pyrazoloazole-based magenta couplers are known to have inferior image storage properties, especially light resistance, compared to magenta dyes obtained from 5-pyrazolone-based magenta couplers, and this is a major problem when put to practical use. This has become a problem.

Additionally, pyrazoloazole magenta couplers are
It also has the disadvantage that color development is lower than that of 5-pyrazolone magenta couplers, and the maximum density of the obtained magenta dye image is low.

As stated above, the reality is that no silver halide photographic material has yet been found that has excellent properties in terms of color reproducibility, image storage stability, and color development of magenta dye images.

[Objective of the Invention 1] The first object of the present invention is to use a pyrazoloazole magenta coupler to form a magenta dye image with an excellent hue in which the absorption on the long wavelength side sharply decreases to zero, and to improve color reproducibility. An object of the present invention is to provide an improved silver halide photographic material.

A second object of the present invention is to provide a silver halide photographic material with excellent preservability of magenta 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 object of the present invention is to provide a silver halide photographic material having at least one silver halide emulsion layer on a support, in which at least one of the silver halide emulsion layers has the following general formula [M -I] and at least one compound represented by the following general formula [I].

In the general formula [MI], Z represents a nonmetallic atom group necessary to form a nitrogen-containing heterocycle, and the ring formed by 2 may have a substituent.

X represents a hydrogen atom or a group that can be separated by reaction with an oxidized product of a color developing agent.

Further, R represents a hydrogen atom or a substituent.

General formula [I] R' O+ CH2J CH20+-R2 In the formula, R1
and R2 are each an aliphatic group or 10OR' (
R' represents an aliphatic group. ), J represents a divalent group or a simple bond, and i represents an integer of O to 6.

[Specific Structure of the Invention] In the magenta coupler represented by the general formula [M-11] according to the present invention, 2 represents a nonmetallic atomic group necessary to form a nitrogen-containing heterocycle. , the ring formed by 2 may have a substituent.

X represents a hydrogen atom or a truncated group that is removed by reaction with an oxidized product of a color developing agent.

Moreover, R represents a hydrogen atom or a substituent.

The substituent represented by R is not particularly limited, but typical examples include alkyl, aryl, anilino, acylamino, sulfonamide, alkylthio, arylthio, alkenyl, and cycloalkyl, but in addition to these, halogen Atom and cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl, acyl, carbamoyl, sulfamoyl, cyan, alkoxy, aryloxy, heterocycleoxy, siloxy, acyloxy, carbamoyloxy, amine, alkylamino, imide, Also included are ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, and heterocyclic thio groups, as well as spiro compound residues, bridged hydrocarbon compound residues, and the like.

The alkyl group represented by R preferably has 1 to 32 carbon atoms, and may be linear or branched.

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

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

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

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

The alkenyl group represented by R preferably has 2 to 32 carbon atoms, and the cycloalkyl group preferably has 3 to 12 carbon atoms, particularly 5 to 7 carbon atoms, and the alkenyl group may be linear or branched.

The cycloalkenyl group represented by R has 3 to 3 carbon atoms.
12, especially those of 5 to 7 are preferred.

Sulfonyl groups represented by R include alkylsulfonyl groups, arylsulfonyl groups, etc.; sulfinyl groups include alkylsulfinyl groups, arylsulfinyl groups, etc.; phosphonyl groups include alkylphosphonyl groups, alkoxyphosphonyl groups, and aryloxyphosphonyl groups. , arylphosphonyl group, etc.; Acyl group includes alkylcarbonyl group, arylcarbonyl group, etc.; carbamoyl group, arylcarbamoyl group, etc.; sulfamoyl group includes alkylsulfamoyl group,
Niacyloxy groups such as arylsulfamoyl groups include alkylcarbonyloxy groups, arylcarbonyloxy groups, etc.; carbamoyloxy groups include alkylcarbamoyloxy, etc.; ureido groups include alkylureido groups, arylureido groups, etc.; sulfamoylamino groups Examples of the heterocyclic group include an alkylsulfamoylamino group and an arylsulfamoylamino group; 5- to 7-membered heterocyclic groups are preferable, and specific examples include a 2-furyl group, a 2-chenyl group, a 2-pyrimidinyl group, 2-benzothiazolyl group, etc.; as the heterocyclic oxy group, those having a 5- to 7-membered heterocycle are preferred, such as 3.
4.5.6-tetrahydrobilanyl-2-oxy group, 1
-Phenyltetrazole-5-oxy group, etc.; The heterocyclic thio group is preferably a 5- to 7-membered heterocyclic thio group, such as 2-pyridylthio group, 2-penzothiazolylthio group, 2.4-diphenoxy- 1.3.5-triazole-6 monothio group, etc.: Siloxy group includes trimethylsiloxy group, triethylsiloxy group, dimethylbutylsiloxy group, etc.; imide group includes succinimide group, 3-heptadecylsuccinimide group, Nispiro compound residues such as phthalimide group and glutarimide group include sp0[3.3]hebutane-
1-yl, etc.; As a bridged hydrocarbon compound residue, bicyclo[2.

2,1]hebutan-1-yl, tricyclo3.

3,1.133' ]]decan-1-yl7,7-dimethyl-bicyclo[2.2.1]hebutan-1-yl and the like.

Groups that can be separated by reaction with the oxidized product of the color developing agent represented by X include, for example, halogen atoms (chlorine atom, bromine atom, fluorine atom, etc.), alkoxy, aryloxy, heterocyclic oxy, acyloxy, sulfonyloxyaryloxy. carbonyloxy, alkoxyoxycypriloxy, alkylthio,
Arylthio, polycyclic thio, alkyloxythiocarbonylthio, acylamino, sulbonamide, nitrogen-containing heterocycle bonded by N atom, alkyloxycarbonylamino, aryloxycarbonylamino, carboxyl (R1' is the same as the above R, Z ' has the same meaning as 2 above, R21 and R3' are a hydrogen atom, an aryl group,
Represents an alkyl group or a heterocyclic group. ), preferably a halogen atom, particularly a chlorine atom.

Examples of the nitrogen-containing heterocycle formed by Z or Z' include a pyrazole ring, an imidazole ring, a triazole ring, and a terazole ring. Examples of the substituent that the ring may have include the above-mentioned R The following are mentioned.

More specifically, what is represented by the general formula [M-i] is represented by, for example, the following general formulas [M-IIJ to [M-Vl]
: Represented.

[M-Ill [M-I[[] [M-IV] [M-Vl [M-Vl] CM-Vl] In the general formulas [M-II] to [M-■], R1-R
8 and X have the same meanings as R and X above.

Also, preferred among the general formulas [M-I] are those represented by the following general formula [M-■].

General formula [M-■] Formula R+, X and Z+ Hata formula [M-I]
It has the same meaning as R, X and 2.

Among the magenta couplers represented by the general formulas [M-If] to [M-Vl], particularly preferred are magenta couplers represented by the general formula [M-Ill].

The most preferred substituents R and R1 on the heterocycle are those represented by the following general formula [M-IX1.

The general formula CM-IXI s Rto-C- R+ in the formula R9. RIO and Ro each have the same meaning as R above.

Moreover, the said Rs. The two words R9 in R+o and R+t
and Rto may be bonded to form a saturated or unsaturated ring (e.g., cycloalkane, cycloalkene, heterocycle), and R11 may be bonded to the group ring to form an organic hydrocarbon compound residue. good.

Among the general formula [M-Xl, (i) Rs~
When at least two of R++ are alkyl groups, (i
i) One of Rs to Rn, for example R++, is a hydrogen atom, and the other two, R9 and Rto, combine to form a cycloalkyl together with the root carbon atom.

Furthermore, preferred among (i) is the case where two of R9 to R++ are alkyl groups and the other one is a hydrogen atom or an alkyl group.

In addition, substituents that the ring formed by Z in general formula [M-I] and the ring formed by Zl in general formula [M-■] may have, and general formulas [M-If] to [
R2-R8 in M-Vl] is represented by the following general formula [M-Vl].
-X] is preferred.

General formula [M-X] -R' -8O2-R2 In the formula, R1 represents an alkylene group, and R2 represents an alkyl group, a cycloalkyl group, or an aryl group.

The alkylene group represented by R1 preferably has 2 or more carbon atoms in the straight chain portion, more preferably 3 to 6 carbon atoms, and it does not matter whether the alkylene group is straight chain or branched.

The cycloalkyl group represented by R2 is preferably a 5- to 6-membered one.

Below is a representative example of a compound related to this light.

CH.

C.H.

1" I 1 y l + 2ths (Ill) +2ths (Ill) In addition to the above representative examples of compounds according to the present invention, specific examples of compounds according to the present invention include Japanese Patent Application No. 61-9791.
Among the compounds described on pages 66 to 122 of the specification, N091-4, 6.8-17°19-24.2
6-43.45-5, 61-104, 106-12
1. 123-162. Compounds represented by 164 to 223 can be mentioned.

Magenta coupler (
Hereinafter, the magenta coupler of the present invention) was published in the Journal of the Chemical Society.
al of the Chen+1cal
5ociety), Perki
n) I (1977), 2041-2052,
U.S. Patent No. 3,725,067, JP 59-9943
No. 7, No. 58-42045@, No. 59-162548, No. 59-171956, No. 60-33552, Go-43659, No. 60-172982, and No. 6
Those skilled in the art can easily synthesize it by referring to No. 0-190779 and the like.

The magenta couplers of the present invention usually contain from 1.times.10' mole to 1 mole, preferably 1.times.10@-, per mole of silver halide.
It can be used in the range of 2 mol - 8X 10' mol.

The magenta coupler of the present invention can also be used in combination with other types of magenta couplers.

Next, the compound represented by the general formula [II] will be explained.

Examples of the aliphatic group represented by R1 and R2 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. Moreover, these aliphatic groups also include those having substituents.

Furthermore, in -COR', R' represents an aliphatic group, and examples thereof include the same aliphatic groups as those represented by R1 and R2 above.

Examples of the organic group of 2(15) represented by J include an alkylene group, a cycloalkylene group, a carbonyl group, and a carbonyloxy group, and these groups may have a substituent.

Among the compounds represented by the general formula [II], particularly preferred in the present invention are compounds represented by the following general formulas [I[] to [V].

General formula [I[] R30÷CH2CH2O←R4 Nine general formula [II[] R5Q+CH2+-0R6 General formula [IV] CH20R8 R' 0CI-12-C-CH20R9CH20R1〇 General formula [V] In the formula, R3 to R12 are each as described above It has the same meaning as R1 and R2 in general formula [II. m represents an integer of 0 to 6, and n represents an integer of 1 to 10.

Further, in the general formula [rV], any two selected from R7 to R+o may be bonded to each other to form a ring.

Moreover, in the present invention, Japanese Patent Application No. 61-101675,
Compounds described in Akira No. 101676 and No. 61-116342 can also be preferably used.

Next, typical examples of the compound represented by the general formula [E] (hereinafter referred to as the compound of the present invention) will be shown.

Below margin R30+CH2CH2O+-R4 Below margin R50+CH2←0R6 Below margin IV-11 1V-12 Below margin R110CH2min CH2oR12 Some of the compounds of the present invention are commercially available. It can be synthesized by the method described in No. 101675, No. 61-116342, etc.

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

Some of the compounds of the present invention are described in Japanese Patent Publication No. 56-1616. However, the compound of the present invention improves color reproducibility by shifting the maximum absorption wavelength of the magenta dye obtained from the pyrazoloazole magenta coupler to the shorter wavelength side and sharply reducing the absorption at the longer wavelength side to zero. There is nothing suggested about this in the above-mentioned documents.

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 magenta dye obtained from the magenta coupler of the present invention to the shorter wavelength side, and
To reduce absorption in the long wavelength side of 00 nm or more, as a result, to significantly improve color reproducibility, and to improve image storage stability of the magenta dye, and further, to provide a silver halide photographic photosensitive material using the magenta coupler. It has been discovered that the color development of the material can be improved and a sufficiently high maximum density can be obtained, and such an effect has been achieved for the first time by the present invention.

The magenta coupler of the present invention and the compound of the present invention are contained in at least one silver halide emulsion layer, and are preferably contained in a green-sensitive silver halide emulsion layer.

Hydrophobic compounds such as the magenta 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 magenta coupler is usually used in 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 solvent is used in combination. After dissolving and emulsifying and dispersing 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 the present invention particularly applies when applied to color photographic paper used for direct viewing. The effects of this will be effectively demonstrated.

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 materials, in order to perform subtractive color reproduction, a photographic coupler is usually used.
It has a structure in which a halogenated limited emulsion layer containing magenta, yellow, and cyan couplers and a non-light-sensitive layer are laminated on a support in an appropriate number and order of layers.
The number of layers and the order of layers may be changed as appropriate depending on the important performance and purpose of use.

As the yellow coupler, benzoylacetanilide-based compounds, pivaloylacetanilide-based compounds, etc. can be used. A specific example is U.S. Patent No. 2,875,05
No. 7, No. 3,265,506, No. 3.408.194
No. 3.551.155, No. 3,582,322, No. 3,725.072, No. 3,891,445,
West German Patent No. 1,547,868, West German Application Publication No. 2,21
No. 9,917, 2,261.361@, 2,414
．． No. 006, British Patent No. 1,425,020, Special Publication No. 5
No. 1-10783, JP-A-47-26133, JP-A No. 48
-73147, 51-102636, 50
-6341, 50-123342, 50-
No. 130442, No. 51-21827, No. 50-87
No. 650, No. 52-82424, No. 52-11521
This is what was written in No. 9, etc.

As the cyan coupler, phenolic compounds, naphthol compounds, etc. can be used.

Specific examples of sono are US Pat. No. 2,369,929 and No.
, No. 434.272, No. 2,474,293, No. 434.272, No. 2,474,293, No.
No. 2,521,908, No. 2.895,826, No. 2,895,826, No.
3.034.892, 3,311,476, 3.458.315, 3,476.563, 3
．． No. 583.971, No. 3.591, No. 383, No. 3
．． No. 767,411, No. 4,004.929, West German Patent Application (OL S) No. 2,414,830, No. 2
, No. 454,329, JP-A-48-59838, No. 5
No. 1-26034, No. 4B-5055, No. 51-14
No. 6828, No. 52-69624, No. 52-9093
This is what is described in No. 2, etc.

The silver halide emulsion used in the silver halide photographic material of the present invention (hereinafter referred to as the silver halide emulsion of the present invention).
Any of the halogen radicals used in ordinary silver halide emulsions, such as silver bromide, silver iodobromide, silver iodochloride, silver chlorobromide, and silver chloride, can be used as the raw halogen root.

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] The silver halide photographic material of the present invention contains the magenta coupler of the present invention and the compound of the present invention, thereby improving the spectral absorption characteristics of the magenta dye formed from the pyrazoloazole magenta coupler. As a result, color reproducibility can be significantly improved. Furthermore, the image storage stability of the magenta 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 emulsions) Three types of silver halide emulsions shown in Table 1 were prepared by a neutral method and a simultaneous mixing method.

Margin table below - 1 *1 Addition of 2ma per mole of silver halide *2 Addition of 5X10-5 mole per mole of silver halide 3 Addition of 0.9 mmol per mole of silver halide *4 0 per mole of silver halide Addition rate of .7 mmol 5 Addition of 0.2 mmol per mole of silver halide Each silver halide emulsion was treated with the following S T as an emulsion stabilizer after chemical sensitization.
, B-1 was added in an amount of 5.times.10@-3 moles per mole of silver halide.

5OsNH(Ct)Is).

[5D-3] The following margins (Preparation of silver halide color photographic light-sensitive material sample) Next, the following layers 1 to 7 were sequentially coated on a paper support coated with polyethylene on both sides i! I2 (simultaneous coating) to produce silver halide color photographic materials 1 to 43. (In the following examples, the m added is expressed as m per 112 of the photosensitive material.) Layer 1: Gelatin (1.2 g') and 0.291 g
1 (in terms of silver, the same applies hereinafter) of blue-sensitive silver halide emulsion (Ell-1), 0.75 g of yellow coupler (Y-1), 0.3 g of light stabilizer 5T-1 and 0.0
15CI of 2,5-dioctylhydroquinone (1''Q
A layer containing dinonyl phthalate (DNP) of 0, 31;I in which -1> is dissolved.

Layer... Gelatin (0.9a) and 0.04(
A layer containing 0.217 DOP (dioctyl phthalate) in which HQ-1 of J was dissolved.

Layer 3: Gelatin (1,40), 0.2 (J) green-sensitive silver halide emulsion (Em-2), and 0.9 mmol of the magenta coupler shown in Table 2, 0.2 g Table-2
The compound of the invention shown in 0.25 (l) of light stabilizer 5T-
Dissolve HQ-1 of 2 and o, olg
(7) DOP and 6+1 (l of the following filter dye Al-
A layer containing 1.

Layer 4: Gelatin (1.2 g) and the following 0.
6g of ultraviolet absorber UV-1 and 0.05g (7))
A layer containing 0.39 DNP dissolved in Q-1.

B5... Gelatin (1.4g) and 0.20f;
1 of red-sensitive silver halide emulsion (Ell-3), and 0.54 (] of cyan coupler (C-1) and 0.0I
0,3 in which HQ-1 of O and 0.3 g of 5T-1 were dissolved.
A layer containing g DOP.

Layer 6: Gelatin (1,1a) and 0.2g of DOP and 5111 (0.2g of UV-1 dissolved in it)
Layer containing the following filter dye Al-2 of J.

Layer 7: Gelatin (1,0g), 0. o
A layer containing 2°4-dichloro-6-hydroxytriazine sodium of sg.

Below is the margin (ST-1) l-2 NaU3S(J(zNHO0H (Y -1) jl t Below is the margin) The obtained sample was subjected to wedge exposure recovery using a photosensitive needle KS-7 type (manufactured by Konishiroku Photo Industry Co., Ltd.). After processing according to the following color development processing steps, the maximum density (□l1lax) of the green-sensitive emulsion layer was measured using an optical densitometer (Model PDA-65, manufactured by Konishi Roku Photo Industry Co., Ltd.).

Further, the maximum absorption wave λWaX when the density of the magenta dye image was 1.0, and the density, Da, and OR at 430 ni and 600 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 No. 1 as 100.

The results are shown in Table-2.

[Processing process] Temperature Time Development color development 34.7±0.3℃ 45 seconds bleaching @
34.7±0.5℃ Stabilized for 50 seconds
Dry at 30-34℃ for 90 seconds 60
~80℃ 60 seconds [Color developer] Pure water g o o 1
112 triethanolamine 8gN
, N-diethylhydroxyamine 5g Potassium chloride 2g N-ethyl-N-β-
Methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 5g Sodium tetrapolyphosphate 2g Potassium carbonate
30g potassium fanitate
0.2g Fluorescent brightener (4,4'-diaminostilbendisulfonic acid derivative) 1g Add pure water to bring the total amount to 12, and adjust to p) -110.2.

[Bleach-fix solution] Ferric ammonium ethylenediaminetetraacetate dihydrate 60 (1 ethylenediaminetetraacetic acid 3Q ammonium thio'@acid (70% solution) 1oo1
6 Ammonium sulfite (40% solution) 27.5.
, g Adjust to I) H5.7 with potassium carbonate or glacial acetic acid, and add water to bring the total volume to 12.

[Stabilizing liquid] 1 g of 5-chloro-2-methyl-4-isothiazolin-3-one 2 g of 1-hydroxyethylidene-1,1-diphosphonic acid was added to make 1 fl, and the pH was adjusted to 7.0 with sulfuric acid or potassium hydroxide. 0
Adjust to.

The following margin comparison magenta coupler (MM-1)> As is clear from the results in Table 2, the pyrazoloazole-based magenta coupler of the present invention is compared to the conventionally used 5-pyrazolone-based comparative coupler (MM-1). is the secondary absorption (DB) on the short wavelength side of the dye image obtained by color development.
) is extremely small, but the maximum absorption wavelength is slightly longer,
It also has the disadvantage that absorption (DR) on the long wavelength side is somewhat large. Furthermore, the color development and light resistance expressed by specific sensitivity and maximum density are also not sufficient. (Sample No. 2
~No, 8).

On the other hand, Samples 10 to 43, in which the pyrazoloazole magenta coupler of the present invention was combined with the compound of the present invention, all maintained the characteristic of the pyrazoloazole magenta coupler that the DB was small, while maintaining a sufficiently high peak value. concentration,
Sensitivity is obtained, and the maximum absorption wavelength is 544nI11~
547nffi, which is ideal, and the DR is small, indicating excellent color reproducibility and light resistance.

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 [M-I]
At least one magenta coupler represented by and at least one compound represented by the following general formula [I]
A silver halide photographic material comprising: General formula [M-I] ▲Mathematical formulas, chemical formulas, tables, etc. are available▼[M-I] [In the formula, Z represents a group of nonmetallic atoms necessary to form a nitrogen-containing heterocycle; The ring may have a substituent. X represents a hydrogen atom or a group that can be separated by reaction with an oxidized product of a color developing agent. Further, R represents a hydrogen atom or a substituent. ] General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc. are available▼[I] [In the formula, R^1 and R^2 are each an aliphatic group or -COR'(R' represents an aliphatic group.) represents J
represents a divalent organic group or a simple bond, and l is 0 to
Represents an integer of 6. ]