JPS60203943A - Silver halide color photosensitive material - Google Patents

Abstract

PURPOSE:To enhance coupling speed, and to obtain superior graininess and sharpness by incorporating a specified coupler. CONSTITUTION:A silver halide emulsion layer contains the coupler which couples with the oxidation product of a developing agent and cleaves a bond joining the coupler residue Coup with N at the 2-position of a 5-pyrazolone type releasable group. The coupler is represented by the formula in which Coup is a residue free from H at the active site of the coupler capable of coupling the oxidation product of the color developing agent; L is -OCH2- or -O(CO)-, and it combines with Coup through O; n is 0 or 1; Y is H or a <11C org. residue; and X is H, alkoxy, alkylthio, aryloxy, arylthio, arylazo, N-contg. heterocyclic group combining through N, heterocyclic oxy, such thio, such azo, acyloxy, or sulfonamide. After the first coupling for forming a dye image is executed by using such a coupler, the releasable group released on the coupling reaction causes the second coupling reaction, and the dye produced at that time flows out into a developing soln. When a large amt. of said oxidation product of the developing agent is produced, an excess of the oxidation product due to the second coupling reaction. Since such a coupler has high speed in the first and second coupling reaction, superior graininess is obtained. Each individual dye cloud does not grow to a certain degree, and occurrence of mottles is suppressed. As a result, sharpness can be enhanced.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to (a) a silver halide color photographic light-sensitive material containing a photographic coupler capable of improving graininess and sharpness.

(Prior art) By color-developing a silver halide color photographic material, an oxidized aromatic-grade amine color developing agent and a coupler react to form indophenol, indoaniline,
Indamine, azomethine.

It is known that phenoxazine, phenazine and similar dyes can be produced to form one color images. In this method, a subtractive color method is usually used for color reproduction, and the color images of yellow, magenta, 2, and cyan, which are in the residual color relationship with the silver halide emulsion selectively exposed to W, edge, and red, are used. A one-house cutter is used. To form a yellow image, acrylacetanilide or dibenzoylmethane couplers are used, and to form a magenta color image, pyrazolone, pyrazolobenzimidazole, cyanoacetophenone or indazolone are used. Phenolic couplers, such as phenols and naphthols, are commonly used to form cyan images.

In recent years, silver halide photographic materials, especially color photographic materials, have been required to have even higher image quality due to the increasing sensitivity of 1507boo and the trend toward smaller formats such as 110f or 1t1, which is represented by the size of a disk camera. .

Regarding image quality, it is particularly important to improve sharpness and graininess.

Traditionally, couplers have been used not only to form dye images but also to release photographically useful groups.
There are many things to do. Compounds that release photographically useful groups are used for purposes such as improving color reproducibility, improving graininess, improving sharpness, or increasing sensitivity.

For example, U.S. Pat. No. 3,227. '! ! ；ψ No., same 3゜/
1! , θI! 1.2 and Journal of t
heAmerican Chemical 5ocie
ty Vol. 72 (7250), page 7533, couplers that release development inhibitors or color patches from the coupling position are described. Also, the US special liver No. 3, 70s, t
Roi discloses a coupler that is capable of releasing the whitening inhibitor "ItIII" from the coupling site after reaction between the developer and the coupler.

Couplers are known in which photographic couplers undergo oxidative camping with aromatic primary amines to release another photographic coupler as a coupling-off group. For example, as a coupler that releases a pyrazolone coupler, it is suitable for coupling with a 2-equivalent yellow coupler! - A coupler with a pyrazolyloxy group bonded to the U.S. Patent Kinuhiro, /30. '
It is described in the I core. The enol oxygen atom of the j-pyrazolone magenta dye-forming coupler residue is blocked by the coupler residue, and a single coupler is obtained.
It was destroyed on 3.1/17.2. If the coupling position is bonded to the no position of the ≠-monoalkyl-3-vinzolin-j-one group and the 7 λ-equivalent coupler is used, West German Special Edition Published Publication @ 11 (lJ, Ls) No. 1,637. 11
7. U.S. Patent No. ≠, /30. ≠
, 27 melody is 01. Sth! , 637, I am looking at lf/7. Coupler ray that removes 7 groups of pyranylyloxane, coupling speed is low, graininess or brightness,
The improvement effect of It cannot be overlooked.

(Purpose of the invention) ;! The object of the invention is, firstly, to provide a coupler with a high coupling speed, excellent graininess and sharpness. We are committed to providing synaptic materials. Another object of the present invention is to provide a color photographic photosensitive material which has a uniform gradation distribution and a high degree of tolerance.

(Structure of the Invention) The above features of the present invention include at least seven non-rogenated mulberry extracts, which are expressed by the following general formula (1), and are represented by the following general formula (1), Silver halogenide color photograph containing a photographic coupler characterized in that the bond connecting the coupler residue Coup and the 2-position nitrogen atom of the 5-pyrazolone thread separation group is cleaved in the coupling instep with #Achieved through optical materials.

(In the formula, Coup represents a residue obtained by removing the water ≠ atom at the active site from a coupler capable of coupling with a color developing main co-oxidant, and L represents 10'C112- or -UC-, and these The group is an oxygen atom bonded to (1 Coup, n represents/or 0, Y
represents a hydrogen atom or an aliiso residue having a carbon number of /θ or less; castle group, heterocyclic oxy group,
(represented by a heterocyclic azo group, an acyloxy group, or a sulfonamide group) However, the photographic coupler represented by the general formula (1) can be tautomeric, and can be expressed by the following general formula (11). It has the same meaning as .

(In the formula, Coup, L, n, X and Y are general formula (1)
It is synonymous with instep. ) Coupler residue Co in general formula (1) or (b)
Up is used in silver halide color photographic materials. Examples include residues of yellow, magenta, cyan, or colorless couplers.

As examples of various element-forming coupler residues, yellow, magenta and cyan coupler residues are illustrated below in this order.

As an example of a yellow image forming coupler residue.

Pivaloylacetanilide type, benzoylacetanilide type, malon diester type, malondiamide type, dibenzoylmethane type, benzothiazolylacetamide type, malon ester monoamide type.

Benzothiazolylacetate type, benzoxacylylacetamide type, penzoypzolylacetate type, benzimidazolylacetamide type or benzimidazolylacetate type coupler residue, US patent 3-”
t/l' + IJ'L contained in '5, a coupler residue derived from a heterocyclic tt-substituted acetamide or a heterocyclic acetate, or U.S. Pat. No. 3,770, ≠≠6, British Patent/, ≠ .

No. 17/, West German patent (ULS), -21503,0ri2
issue, when released in Japanff! ; a coupler residue derived from the acylacetamides described in No. 0-/39,731f or Orijo-Tedis Closure No. 15737;
Examples include the heterobar type puller residue described in US Pat. No. 6,57≠.

The magenta colored single family-forming coupler residue is preferably of the j-oxy-pyrazoline type, pyrazolobenzimidazole type, pyrazolotriazole type, cyanoacetophenone type, pyrazoloimidazole type or the West German published patent application (( Jl, S) No. 3, 7.2/, P55, No. 6) is preferably an N-heterogeneous acylacetamide type coupler residue.

Cyan e1! As the Ii palpitation-forming coupler residue, a coupler residue supporting preferably a phenol nucleus or an α-naphthol nucleus is used at the 7' end.

Examples of coupler residues that do not have a negative cumulative effect include indanone-type and acetoneenone-type coupler residues; specifically, US Pat.

θ62,273 - Sand 1 time ≠, Q dodo, ≠ Ri No. 1, same! ,
1, 3.2.311Lj, 3. ? 5g, Tata No. 3,
lji3. ri Otsu l, Tatata Go, same it, o≠ Otsu, 57 Hirosuke, Shirutaha 4 3, 23, and those written in Tata Otsu Go, etc. with 2L are applicable.

In the 3n coupler expressed by equation (1), n =
/ is a coupler residue! - The 11-position y-atom of pyrazolones is understood to be bonded via a methyleneoxy group or a carbonyloxy group, and is also an active site?・
It is bound by purple atoms. These couplers are first cleaved between the coupler active site and the di atom by a coupling reaction with an oxidized developing agent, and a subsequent decomposition reaction gives the nitrogen anion at the 2-position of the pyrazolone frame. Conceivable. According to the general formula (1) of the present invention.

As L, a timing group referred to as a photographic group-releasing compound can also be used. Such timing bases include the US special IPF No. ψ1.2 tar, ?
As described in No. 62 and %Kokai No. 57-56137, intramolecular nucleophilic reaction (by g-conversion reaction), British Patent No. 20723A
3A, JP-A-57-/, iψ23≠ issue, j7-/♂I
Examples include those based on electron transfer via a conjugated system, such as No. r033.

These known timing groups are less effective in improving graininess and sharpness than L of the present invention.

The coupler of the present invention is highly color-forming, and the released turbinezolone-based leaving group can undergo a coupling reaction with one more molecule of saponified developing agent. That is, the release rate of the photographic coupler represented by the general formula (1) -ar ↓ release δ 扛' IC terpyrazolone system is the combination of more anions in the following formula! structure becomes possible, and it becomes possible to function as a 4-piece 1+1 coupler for one year. The dye produced by the coupling reaction between this pyrazole (or pyrazolone) derivative and the saponified developing agent is soluble in an alkaline aqueous solution, and is at least partially s, i*i IP! , it is caused by something flowing into the instep.

When using a coupler with high color development, the graininess of the resulting color image is often worsened, but when the coupler of the present invention is used for a period of time, High color development and outstanding graininess can be obtained.

The reason for this is thought to be that when the coupler of the present invention is used, a single dye cloud does not grow beyond a certain level, and the generation of 7 tors due to the 9 defects associated with highly chromogenic couplers is suppressed. After the first camping reaction L6 of fc which forms a bright color patch image, the released 7' leaving group undergoes a second coupling reaction, and the dye produced at this time is developed. It leaks into the liquid.

When a large amount of the developing main tetravalent product is generated, the excess oxidant is consumed by the second coupling reaction. It is believed that in the couplers of the present invention, both the first coupling reaction and the second coupling reaction are fast and slow, resulting in extrusion that provides excellent graininess.

The reason why the coupler of the present invention has excellent sharpness can also be explained by the above mechanism. That is, when the coupler of the present invention is used, a dye cloud with a size larger than an individual dye cloud j·1 is generated. This is considered to have made a positive contribution to improving sharpness. Further, the coupler released from the coupler of the present invention has diffusivity,
This is the nephew, image agent oxidized product fX: It has the effect of suppressing color development because it is consumed. This is a kind of present 'I&l' suppression.
ilJ release coupler (hereinafter referred to as [DiRJ coupler)]
You may think so.

It is understood that the Etsuji effect is the reason for Gunei no Hi's improvement.

By the way, VIU couplers have conventionally been generally used in scene negative photosensitive materials. At present, it has not been possible to obtain comparable optical performance with other light-sensitive materials. For example, when applied to color reversible materials, each color image treatment generally has a high development activity, and the problem arises that the development inhibitory layer is not sensitive to light. This 7L is the conventional JJIR
Is the coupler a type of inhibitor that absorbs silver halide? Because it was used. However, the Kashishi of the present invention had the grain improvement effect and sharpness improvement effect 2 which were useful even when used as a color anti-III photosensitive material. In other words, the coupler of the present invention releases dust during the color reversal process. The compound L acts as a scavenger for the color developing agent.
Consumes Zhou Raku Oxide. The remaining silver halide is eventually consumed by the 7H coupler produced by separation, and the total color development of KL is suppressed, indicating the effect of the Kaptsu coupler.

The group represented by Y in the general formula (1, ,) is preferably one listed below. Alkyl group.

Alkoxy group, acylamino group; carbaniyl group, alkoxycarbonyl group, cyano group, halogen atom, alkylthio group, monolyl group, carboxyl group, sulfonamido group, or *M! ;! il: (For example, 5 containing a nitrogen atom, a sulfur atom, and a sulfur atom as a henaro atom)
member ゛ or six-membered ring).

When these substituent groups contain an alkyl group moiety, it may be a straight or non-conducting group, a cyclic group or a chain group, a branched group, a saturated or an unsaturated group, and may be included in Y. The total carbon number is 10 or less, preferably 5 or less.

In the general formula (1), when X is an yaron-containing hetero (ni), preferably (2, pyrazolyl group, imidazolyl group, /, 2.'l-t') azolyl group, benzotriazolyl group or a tetrazolyl group.Furthermore, when X represents an alkanoyloxy group, an alkylthio group, an alkoxy group, or an alkylsulfonamide group, the alkyl group is preferably a group having a carbon number of 1 to /r, and the group is substituted or Non-contributory, chain or cyclic, straight chain or branched 1M
It's good to have a tag or fumewazuzai, and it's good to be able to do it. Also, when X represents an arylthio group, a phenylthio group is preferable.
+-.

゛Yo, it's a heterocyclic oxy group, a penarocyclic thio group.

When referring to a heteroazo group, the heterocyclic group is a 5-membered or e-membered ring, and the heteroatom can be selected from a so-chord atom, an oxygen atom, or a sulfur atom. When X represents a heterocyclic thio group, preferred examples include a dizolylthio group, a diazolylthio group, a thiadiazolylthio group, a diazolylthio group, a benzimidazolylthio group, or a tetrazolylthio group. When X represents a heterocyclic azo group, a pyridylazo group is preferred. When X represents an arylsulfonamide group, an aryloxy group or an arylazo group, the aryl group is preferably a phenyl group or a nantel group (two examples are given).

The preferred examples of X described above may further have a substituent. That is, when X represents a halogen-containing hetero=6; t-$, an alkoxy group, an acyloxy group, a sulfonamide fluoride, an alkylthio group, a 2-arylthio group, an arylazo group, a Peter block thio group, an aryloxy group, or an arylthio group. The substitutable position IK may span one or more of the following 1Ir1 radicals: alkyl groups (e.g. methyl group, t-i thyl group), alkoxy groups (e.g. methoxy group).

Acylamino group (e.g. acetamide odor, benzimide group), alkoxycarbonyl group' ()41 Evamethkin carbonyl 8:, phenoxycarbonyl group), alkylsulfonyl group (1+l+eha methanesulfonyl group)
, halogen atom (e.g. chlorine atom), thioureido group, carbamoyl group (e.g. N-ethercarbamoyl group)
, hydroxy 82 carboxy group.

Phenylsulfonyl group, phenyl group, ureido group (e.g. N-ethylureido group), hydrazinyl group (e.g. λ
-formylhydrazinyl group), acyl group (eg, acetyl group), and alkylthio group (menarteo, decylthio group, etc.).

The above-mentioned example of ”
).

Examples of the photographically useful groups contained in X in 2 in formula (1) include ``Kon 5 External Inhibition ~'', Gen Ichike Promotion 4j, Fogging Agent 1 Dye, Kikaraku, Coupler, Button Removal Promotion, To the halogenated seven baths 1. I can name things like the escape-from-belonging thing or the 1tjlJ rule for suppressing button-off! Sign.

A specific PLJG group can be selected depending on the purpose of it. Also, the timing is different depending on the purpose of each person.
J -Shi and Section V (action can be expressed.

The timing of the appearance of the copying piece can be determined by selecting the group represented by L and Y in the general formula (1). However, depending on the purpose, the photographic effect of f'UG can be adjusted as desired. Seventh, it can be done by adjusting the PLJG group, for example, by adjusting whether it is electron-withdrawing or donating, or by adjusting whether it is hydrophilic or hydrophilic. A giant monkey.

Preferred examples of PI and IG include the following.

General formula (P-i') General formula (P-2) (Gl) f General formula (P--?) General formula (P-F, )2 General formula (P-j) General formula (P-4) General formula (P-7) -bσ formula (i'-g) ((-b)
f General formula (P-y) Formula 11J, Gl is an elementary atom at 7, a halogen atom, an aryal camellia (e.g. a notel group, an enal monato), an acyl 1 mino J
Stop (9!leiJ benzamide group, hexaneamide group)
, alcoco (butoxy group, benzyloxy group), sulfonamide group (e.g. octane sulfonamide group, para-toluene sulfonamide group), aryl group (e.g. phenyl group, talolophenyl group), alkylname group (e.g. alkylamino groups (cyclohexyl-termino groups, etc.), anilino groups (anilino groups, ≠-nodoxycarbonyl='nilino groups, etc.), amino groups, alkoxycarbonyl groups (methoxycarbonyl groups), vinyl leather, plastic carbonyl group, etc.),
Acyloxy group (acetyl group, butanoyl group, benzoyl group), nitro group, cyan group, sulfonyl group (phthanesulfonyl group, benzenesulfonyl group, etc.), aryloxy group (phenoxy group, naphthyloxy group, etc.), hydroxy group .

Thioamide group (butanethioamide group, benzene theocarbonamide group, etc.), carbamoyl group (carbamoyl group, N-1 arylcarbamoyl group, etc.).

Sulfamoyl group (sulfamoyl group, N-arylsulfamoyl group), calphosol group, ureido thread (
(silido group, haetherureido group, etc.) or aryloxycarbonyl group (phenoxycarbonyl $,
4L-methoyacphenoxycarbonyl group, etc.), where U2 represents a hydrogen atom, an alkyl group (eg (gemeter group, ethyl group)), or an aryl group (eg, phenyl group, naphthyl group).

In the formula, Ga is a hydroxy group, a sulfonamide group (e.g. a haftanesulfonamide group, a benzenesulfonamide group)
% represents an amino group, alkylamino group (e.g. etelamino group, cyclohexylamino group), anilino group (e.g. anilino group, V-methyl 1-nilino group), or a certain water atom, and the λ position in general formula (P-5) 3 may be the same or different, but both cannot be hydrogen atoms.

In general formula (1'-6) b-yo (P-7), G4 represents an aryl group (eg, phenyl, naphthyl group).

In a et al., G5 is a hydrogen atom, a heterocyclic thio group (for example, a group represented by the general formula ()'-3) or (i'-p)),
Or it does not represent a nitrogen-containing heterocyclic group fused to a benzene ring (for example, a group represented by -1v formula (P-/) or (P-2)).

f represents l or 20 history number.

In the formula, vl is a nitrogen atom or 102 groups (G.

1 represents the same meaning as already explained and may be the same or different from other 01s present in the molecule.

In the formula, ■2 is an oxygen atom, a sulfur atom, or a - group (
02 represents ■ 2, which has the same meaning as explained in section 2. ).

In the general formula (P-ψ), when 2 and ■1 are 102 groups, the two 01 groups are connected to form a benzene fused ring (for example, v2 is -N), and the benzimidazolylthio group is When V2 is an oxygen atom, it becomes a benzoxadinorthio group).

General formula (P-/), (P-,2), (P-J).

(P-Hiroshi), (P-s), (P-Otsu), (P-7), (
, t'-,1') Oj and (P -9) Koi iG 1
, G2°G3. When G4 or G5 contains an alkyl group moiety, the alkyl group has a carbon number of /~2.2, preferably /
-10 may be substituted or unsubstituted, linear or branched, diluted or cyclic, saturated or unsaturated. Furthermore, G1, G2. G3゜When G4 or G5 contains an aryl group, the aryl group has 6 to 1 carbon atoms.
O is preferably an unsubstituted or unsubstituted phenyl group.

The general formulas (P-/), (P-, z), (i'-3) and (P-Hiro) are removed by development inhibition'+tjlJ. Compounds containing these groups and corresponding to general formula (1) are broadly defined as L)
There is something called LR coupler. The DIR coupler according to the present invention can more effectively control the range of action of the H411 inhibitor than the known VL coupler, and has sufficient stability. As a result, a color photographic image with good color photographic image quality due to the single-layer graininess effect and particularly good sharpness can be obtained.

General formula (, P-s) (P-6) Fu・Yobi (P-7)
is the one that reduces the sand reduction effect at the current location. This J
``Various results are known about the effects of L and other groups on regeneration properties.Developed herbal drug oxidized product?When reduced, it is called a competitive additive and is good for improving graininess or sharpness, and halogenated @ Increases sensitivity when reducing or acting as an auxiliary developer.

General formulas (P- and) and ()'-! P) is an example of a coupler. These compounds function as competitive couplers and are therefore particularly useful for grain improvement.

In the general formulas (P-s), (, P-, etc.) and (P-7), when G5 is a development inhibitor such as a heterocyclic thio group, a crushing effect is added, so 1) 1) t A function as a coupler can be added efficiently.

In the present invention, when X is a current accelerator, sensitivity can be improved in addition to the effects of improving graininess and sharpness. Examples of such X include alkylhydrazinyl. Contains a heterocyclic thio group.

Furthermore, the present invention is particularly effective in the following general formula (fil)'! This is when the coupler is represented by a taba (■). These couplers are preferred because of their high coupling speed.

Formula (Ill) 1(,1-C-CH-C-R2 0M In the formula, Y and X have the same meanings as in the general formula (1). R1, R2r, - and lt3 each represents an aliphatic group, an aromatic group, an alkoxy group, anilino group, or a heterocyclic group.Furthermore, R3 may be an acylamino group.R4 is a nitrogen atom, An acylamino group, an alkoxy group or an Ill costal group. n is 1
Represents an integer of ~l.

In the formula, ■ is also 1. R2, R3'tf, and buko are preferably represented when R4 is an aliphatic group, or preferably, the number of carbon atoms is 1 to 32, and tt = p
It may be N or unsubstituted, linear or cyclic, linear or branched, saturated or unsaturated.

A preferred substituent for the alkyl group is an alkoxy group.

Aryloxy group, amino group, acylamino group.

These halogen atoms and the like may themselves have substituents. Specific examples of aliphatic classes on the south coast include the following: isopropyl group, inbutyl group, tert
-butyl group, inamyl group.

tert-amyl group, /, I-dimethylbutyl group.

Dodecyl group, hexadecyl group, octadecyl group, cyclohexyl group, 2-methoxyisopropyl a:.

! -Phenoxyisopropyl group 1.2- p -te
Examples include r t-bunalphenoxyisopropyl group, α-aminoinpropyl group, α-diethylaminopropyl group, and the like.

1, ■ 2 or R3 is an aromatic group (especially phenyl group)
Aromatic groups may be unsubstituted if desired. Aromatic groups such as phenyl groups include alkyl groups having 32 or less carbon atoms, alkenyl groups, alkoxy groups, alkoxycarbonyl groups, alkoxycarbonylamino groups, +j-th rib amide groups, aryalsulfamoyl groups, alkylsulfonamido groups, and alkyl groups. The pupil may be imitated by a ureido group, an alkyl-substituted succinimide group, etc. In this case, the alkyl group may have an aromatic 4tw group such as phenylene interposed in the chain. The phenyl group may also be directly substituted with an aryloxy group, an aryloxycarbonyl group, an arylcarbamoyl group, an arylamido group, an arylsulfamoyl group, an arylsulfonamide group, an arylureido group, etc.
Each of the 1 aryls 41i of the Shira substituents may be further supplemented with one or more alkyl groups having a total number of carbon atoms of 1 to λ.

1 (11,
The amine group, hydroxy group, carboxy group, sulfo group, nitro group, cyano group, and thiocyano group, including L, may be substituted with halogen or an atom.

Also R1. R2'! Alternatively, R3 may represent a substituent (1) in which a phenyl group is fused with another ring, such as a naphthyl group, a quinolyl group, an inquinolyl group, a chromanyl group, a chromanyl group, or a tetrahydronaphthyl group. These substituents may themselves have a substituent or substituent group.

1, 2. When R3 or 4 is an alkoxy group, the alkyl moiety is a carbon number from 32 to 32, preferably a chain or branched alkyl group, an alkenyl group, a cyclic alkyl group, or a cyclic alkyl group. It represents an alkenyl group, which may be substituted with a halogen atom, an aryl group, an alkoxy group, etc.

When R1, 几2 or RU3 are replaced by a heterocyclic group, each of the heterocyclic groups is bonded via one of the ring-forming carbon atoms. Such double rings include thiophene, furan, biran, pyrrole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, indolizine, imidazole, thiazole, oxazole, triazine, and thiadiazine.

An example is Oxazino. These may also have substituents on the ring.

When R1, R2 or R3 is an anilino group, the anilino group may be substituted. Examples of substituents include alkyl groups having 32 or less carbon atoms, argunyl groups, alkoxy groups, alkoxycarbonyl groups, alkoxycarbonylamino groups-13hUj)M amide groups, alkylsulfamoyl groups, alkylsulfonamide groups, and alkylureido groups. , alkyltit ij # tfuranimide group, etc. In this case, an aromatic group such as phenylene is interposed in the alkyl group chain, making it confusing. Anilino group also includes aryloxy group, N-arylcarb7yl group, and arylamido group.

It may be substituted with an arylsulfamoyl group, an arylsulfonamido group, an aryl ureido group, an aryl group, etc., and the aryl group of these substituents has a carbon number of -8-1 to 22. 1 or more alkyl groups
6'It's okay to be embarrassed. The anilino group further has an ash number/~3
．． (2) may be substituted with an amino group, a hydroxy group, a carboxy group, a sulfamoyl group, a sulfo group, or a carbamoyl group. The anilino group may be further substituted with a nitro group, a cyano group, or a halogen atom.

When R3 represents an acylamino group, it is an aliphatic acylamino group or an aromatic acylamino group. R3
When represents an aliphatic acylamino group, the aliphatic group has 1 to 32 carbon atoms, preferably / to 2 carbon atoms, is @-shaped or unsubstituted, --shaped or cyclic, straight-chained or branched, saturated or unsaturated, or not. However, the following are preferred examples of honorable groups: halogen atom, aryl group.

Examples include phenoxy group, alkoxy group, alkylthio group, arylthio group, acylamino group, carboxyl group, alkoxycarbonyl group, and hydroxyl group. Further, when 几3 represents an aromatic acylamino group, a substituted or unsubstituted benzamide group is a preferred example. Substituents include acylamino group, sulfonamide group, alkoxy group, sulfamoyl group, alkyl group, halogen atom,
It is selected from an imide group, an alkoxycarbonyl group, a carbamoyl group, an alkylthio group, and the like.

The coupler of the present invention is preferably used in combination with other ordinary couplers, and is l×/θ−2 mo1 with respect to the main coupler.
% ~ / 00 mo1% tL< is evening θITI
Used by Section 01.

Compounds of σfL used in the present invention include the following synthetic examples, but are limited to these.The compounds of the present invention are generally synthesized by the following synthetic routes. stand j
It can be pierced.

Narita, A is the coupler residue wH, W represents the chlorine or bromine atom bonded to the coupling position of A, and 'Xw and Y are the same laziness defined earlier.

Once protected with a hydroxyl group or a gamma syl group, which is the d group of pyrazole, the above-mentioned;

The above one-doped Matata reaction is carried out using an image-based bath medium (usually l'J, N
- dimethylformamide and 9 or 9 or 1 raw solvent (1 1 (for example, toluene, etc.)), the presence of a dam or no base, 0 to 0 (2 warm yoke) It will be held in

The arrows indicate specific methods for representative compounds of the present invention.

Synthesis Example (1) Synthesis of Exemplified Product 8 (1) 2-chloro-2-hibaloyl-xl-chloro-j'-(
Hiro-(2, Hiro-di-t-amylphenoxy)butanamide) acetanilide, 3092, and 3-methylpyrazolone, is'g6 tetrahydrotheophene/,/-dioxide/009 were mixed and stirred for 3 hours at toac. . After releasing the tuna in bliss, vinegared tuna was added with Ether/77 and washed with water. Solvent in oil reservoir depressurization? The residue was separated by column chromatography. /kf silica gel? Please,
The desired coupler 1.2.69Y was obtained by elution using a mixed solvent of amyl acetate and hexane in a ratio of 3/:3.

Synthesis Example (2) Synthesis of Exemplified Compound (5) 3-(J-[:u-(2,t/L-di-t-amylphenoxy)butyramide]benzamide)-ψ-bromo/-(2,F, , &-) ') chloronoenyl)-
5-pyrazolone, 3θ9 and 3-methyl-≠-(2-
phenyltetodizolylteo)-terpyrazolone, c3.
-9 was dissolved in 100 mQ of sulfolane and heated and stirred at gθ'C for 5 hours. After cooling to room temperature, ethyl acetate/74 was added and washed with water. The oil layer was taken, the solvent was distilled off under reduced pressure, and the residue was separated by column chromatography. /H using silica gel.

The desired coupler 1 was prepared by bathing with a mixed solvent of ethyl acetate, hexane and ethanol in l:l:O05.
I got 0.39.

Are there various types of halogenation costs in the silver halide emulsion layer according to the present invention? can be used. Examples are silver chloride, bromide, silver chlorobromide, silver iodobromide, or silver chloroiodobromide.

Silver iodobromide containing 2 molar and 20 moles of silver iodide, 10 to! Shiobikaden containing silver bromide in the θ mole ratio is preferred. There are no limitations on the crystal form, crystal structure, grain size, or grain size distribution of the silver halide grains. The silver halide crystal may be a normal crystal or a twin crystal, and may be a hexagonal crystal, a hexahedral crystal, or an l≠hedral crystal. Length - Teddy closure, 2-53≠
The grains may be tabular grains having a thickness of 00S microns or less, a diameter of at least 0, t microns, and an average aspect ratio of 100 microns or more, as described in 7.

Even if the crystal structure is uniform, the inside and outside have different compositions, making it an IVi-like structure? Even if you don't do it.

Further, silver halides having different compositions may be bonded together by epitaxial bonding, or may be composed of a mixture of grains of various crystal forms. Further, the latent image may be formed mainly on the surface of the particle or may be formed inside the particle.

The particle size of the halogenated rice cake may be fine particles of 0, t microns or less, or dog-sized particles with a projected area diameter of up to 3 microns, and may be a monodisperse emulsion with a narrow distribution, or a polydisperse emulsion with a wide distribution. But that's fine.

These silver halide grains can be produced by known methods commonly used in the industry.

As the color developing agent that can be used in the present invention, there are aromatic primary amines, which are represented by the following general formula (in the formula, R□□
2 and R□2 are hydrogen atoms, alkyl,! i! :, or represents a substituted alkyl group with hydroxyl, alkyl, alkoxyalkyl, alkoxyalkoxyalkyl, or alkylsulfonamidoalkyl, where the father is 1 and i2 is 5 to Z negative A saturated heterocycle may be formed (Rta represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen, n is the number of substituents 13, and represents 1 or λ). The i form is a mineral acid salt (1+l!) is a hydrochloride, a salt, a nitrochloride, and an M salt (for example, an acetate, a naphthalene-α-carboxylate, a methanesulfonate, p-) may be a luenesulfonic acid barrier.

A specific example of a color developer that can be used in the present invention is as follows.

≠-amino, N-diethylaniline, 3-methyl-
Hiro-amino-N, N-diethylaniline, Hiro-amino-he-ether-N-β-hydroxyethylaniline,
3-Methyl-Hiro-aminohether-IN-μm hydroxyethylaniline, 3-methyl-≠-amino-N-
Ether-to-β-methanesulfamide ether aniline,
Hiro-ami/-3-methoxyether-N-β-methoxyetheraniline, etc. In addition, L, 1', A,
~IIPbotographic Pro by 1ason
cessingChemistry” (The Foc
Published by Al Press, / 1966) 22t-2.22 pages, 1 ball of rice 1 special rice 2nd. /ri3,0Ij, T112N
! 1?2,3 Otsu≠ No., Tokukai Showa Ff-6V-? 33, Jet-/2.327, etc. may be used.

In addition, the Kafu development plate may contain a pH-reducing agent, a development inhibitor, an anti-fogging agent, and the like.

Also, if necessary, water softeners, preservatives, and solvents.

Development accelerators, dye-forming couplers, competitive couplers.

It may also include a fogging agent, an auxiliary ophthalmic agent, a viscosity imparting agent, a polycarboxylic acid chelating agent, an oxidation prevention agent, and the like. Specific examples of these additives can be found in Research Disclosure (this D-/76 (73)) as well as in U.S. Patent Nos.
No. 3,723, published in West Germany! .

It is described in No. 622t Tata θ, etc.

The photographic emulsion layer of the photographic light-sensitive material of the present invention may contain a color-forming coupler other than the coupler of the present invention, ie, an aromatic primary amine developer (eg, an aromatic primary amine developer in one-color processing).

Color development by oxidative coupling with noenylene diamine G4 body or aminophenol binding agent);
Can be used with anything other than photo couplers. These photos:;
C,)H couplers may also be available in polymeric form.

1.11 (1. As magenta coupler, j-pyrazolone coupler, birazolone benzimidazole coupler)
.

Cyanoacenal coumaron couplers, open-chain acylacetonitrile couplers, etc., yellow couplers include acylacetamide couplers (e.g. benzoylacetanilide, pivaloylacetanilide), etc.
As cyan couplers, various couplers represented by the Coup of the present invention are used, including naphthol couplers and phenol couplers. Is the coupler of Kosai et al. non-diffusible and has a taste water group called a ballast group in the molecule? However, -fl (can be used in combination with a coupler having an appropriate diffusivity. The coupler may be either equivalent or divalent to silver ions. Also, a colored coupler that waits for the effect of one color correction, or Couplers that release development inhibitors during development (so-called DIR couplers) may be used. Father, D.
In addition to IkC couplers, there are also colorless 1), IR
It may also include a coupling attachment.

The present invention can be applied to general silver halide color photosensitive materials such as color negative film, color page/g-, color positive film, color reversal film for slides, color reversal film for one-shot pictures, and color reversal film for 'RV. can. In particular, when it is used in color negative films, especially color reversal films, which require high sensitivity and high image quality, it has a remarkable effect on improving sharpness and graininess.

The present invention can be applied to a one-layer optical material using a black coupler and a three-color coupler. A detailed explanation of the one-way black color coupler system is given in US Pat. No. 3. t, 2.2
, No. 629, No. 3, 73≠, No. 73j, Dohiro, /26,
4tt No. 1, JP-A-5T 10T 2≠7 No. 7, same! 2−ψ
, No. 2725 and the same! -10r2'lt, there are two and three-color coupler mixing systems, i and esea
A detailed explanation can be found in rch Disclosure/7/2. When these methods are used for, for example, X-ray film, they have the following effects: a reduction in tiHt and an improvement in image quality.

The present invention provides at least two different spectroscopy 11 on a support.
It can also be applied to multilayer, multicolor photographic materials having 8 degrees. Multilayer natural color photographic materials usually include a light-sensitive emulsion layer, an edge-sensitive emulsion layer, and a light-sensitive emulsion layer on a support.

each has at least one agent layer. The order of these layers can be arbitrarily selected as required. Cyan type h in red-sensitive emulsion layer
K coupler? Usually, the edge-sensitive emulsion layer 1 contains a magenta-forming coupler and the blue-sensitive emulsion layer contains a yellow-forming coupler, respectively, but different combinations may be used depending on the case.

The coupler of the present invention has the same color sensitivity of 2 and the sensitivity of 7.
i: It can be added to any layer of a light-sensitive material having at least two emulsion layers to improve sensitivity and image quality. British Patent No. 23. O≠! The explanation given in the above issue may be helpful, but the coupler of the present invention may be added to emulsion layers other than the lowest sensitivity layer.

Useful for improving the sensitivity of negative color photosensitive materials. Even more electric.
In a light-sensitive material having at least three emulsion layers having the same color sensitivity and different sensitivities, when the coupler of the present invention is added to an emulsion layer other than the lowest sensitivity layer, it not only improves the sensitivity but also improves grain quality. It's advantageous. As to the reason for this, the description in Tokuko Sho≠Tar/Ririri No. 5 may be helpful.

Example 1゜α-(piparoyl)-α-(/
-benzyl-j-ethoxy-3-hydattynyl)-cochlorolotadedecyloxyproponylacetanilide (coupler A) is dissolved in a mixture of 100 cc of tricresyl phosphate and 100 cc of ethyl acetate, and 10 g of sodium dodecylbenzenesulfonate is dissolved. A blue-sensitive silver iodobromide emulsion of an emulsion obtained by stirring at high speed with an aqueous gelatin solution/kf/AI' (legal content 3 more
4) After addition and dispersion, it was applied to cellulose acetate paste and dried. This is designated as sample A. Emulsions of the compound and Hiku compound of the present invention were prepared as follows.

Yellow coupler (A) J'Og and coupler & (1) l
Dissolve lizardfish in tricresyl phosphate lOθa and 100 ct of ethyl acetate, and dissolve dodecylbenzenesulfone in soda IO'J and 10% gelatin water #t=/kg? high speed(
・Press to seal the emulsion. In exactly the same manner except that this emulsion was used instead of the emulsion for the yellow coupler,
Sample By was prepared. As shown in Table 1 below, samples C~
H is the coupler of the present invention having a molar ratio of 2j to coupler 8, or the ratio coupler ta+, (b
This is a sample prepared by using an emulsified dispersion obtained by mixing one type of (2).

(Compound described in U.S. Patent No. V,/30.'1.27)
(Compound 'Jf described in U.S. Pat. No. 3.227.j≠
/lJ) The sensitometry results obtained by performing neutral gray 14-tone light on the r samples of A to H above and performing color reversal treatment according to the following prescription are shown in Table 1.

Processing process Time Temperature channel development t' 3r 0CC, ±0.3)□(tl
Water washing λ′〃 Reversal 2′〃 Color development A/.

Adjustment λ′ Existing white 6′ Fixed arrival ≠′ Water wash ≠’ 3g 0c Ansei / ’161 drying 1st development Water 700 mQ.

Sodium Tetrapolyrin 29 Sodium 1 wave 20g Hydrothinone/Septinosulfonate 309 Sodium carbonate (/Water J, C) 302/ -Phenyl-G-Mewol-G-Hydroxymenal-3 Pyrazolidone 2g Potassium bromide Potassium thiocyanate 1.29 Potassium iodide (0,/'Iy bath'/(f, ) 2
Add mQ water 1000m Reverse water 700 mQ Nitrilo・1~・N-N-)limethylenephosphonic acid・6 Na salt 3g Stannous chloride (dihydrate) /9 P-aminophenol 0. /'ij Sodium hydroxide and 9 glacial acetic acid irma Add water / +700 m9 Color developing water 700 mQ Sodium detrapolyphosphate 29 Sodium sulfite 7 g Sodium triphosphate (dihydrate) 369 Potassium bromide /9 Potassium iodide ( O1/related solution) L? Oml Sodium hydroxide 1 39 Citranic acid /, jg Heteru N-(β-methanesulfonamide ether) -3-methyl-≠-aminoaniline sulfate /19 Add ethylenediamine water C 1 week water 700 mu, ! i! ! Shuba Sodium /, 2. Ethylenediaminetetra-acetic acid cough sodium (,2 water temperature) rg Thioglycerin O1≠glacial acetic acid 3mQ Water? In addition, 1000rnfl static white water ♂o o +np enalediaminetetraacetate sodium (, dihydrate) x, og ethylenediaminetetraacetate iron (11) ammonium (cohydrate) i, zo, o! l) Beautifying potassium ioo, og Add water and fix 7.0 Water 100 mu Ammonium tenth sulfate ♂0.09 Sodium binitrate s, og Sodium binitite 5.0g Add water /, 0 stable Water 1f00rrQ Formalin (37 direct weight%) j-, Om? Surfactant solution (trade name: Dorata, OmC'Iwel) Add water /, Ol As shown in the above results, samples B-F of the present invention were compared with -
It can be seen that the level of dog pain is lower than that of tL, G or 11, and the effect of softening the tone is particularly great.

The conventionally known foaming compound ta) + tb),
It is clear that the effect is great when compared with

Next example is 2゜ macenta sword puller;! l)/-(,2,φ,6-dolichlorophenyl)-3-(J-(,2,'7-jit
-Avalphenoxyacetamide)penzamide)-5-
Pyrazolone (coupler B > ioθg with 100 cc of tricresyl phosphate and ethyl acetate i 00 cxK
(Dissolved in H, added to a mixture of 70 g of sodium dodecylbenzenesulfonate and 1 portion of /θ gelatin water bath solution, and stirred at high speed, resulting in an emulsion/soup to make green-sensitive iodobromide mortar milk 411/!
2 (Yo J group @ Sui 3 mole section) was mixed and applied onto the Tama r spoof acid cellulose paste and dried.

this? Let it be sample (1).

An emulsion containing the coupler of the present invention shown in Table 2 or a comparative cabzie added instead of the macenta coupler was prepared in the same manner as above, sample (I), and sample (J).
)(K)(,L)(M)(N) were created. The structure of the comparison coupler is as follows.

Coupler + C1 compound (compound described in JP-A-5.2-2-31)) Example: Emulsion layer and auxiliary layer in the following order on a cellulose triacetate support provided with a 3° undercoating layer. was applied to obtain sample A'.

1st layer: low-sensitivity red-sensitivity emulsion layer cyan coupler 1-(hepkfluorobutyl 1 mido)--1--(λ'-(ko', l'-di-amitunoenoxy)funalamide)-7 Enol/θ0';j'
f tricresyl phosphate 100α and ethyl acetate 1
Dissolved in 00Ct, 70% gelatin aqueous ridge/# and surface active to 11, dodecylbenzenesulfone enemy soda lO!
1) and stirred at high speed to extract the red-sensitive, low-sensitivity, large bromide emulsion (soog) from the emulsion.
Average grain length of silver halide grains: 0.3μ, silver 709
, Centene 609 (containing iodine content: 3 moles), gelatin, water, stabilizers, coating aids, and mixed. Dry film thickness: 2
The ([existent] regular o, tg7m)th λ concave to become μ
Layer: middle window red-sensitive emulsion layer The emulsion lIC of the coupler used in the 7th layer is mixed with a red-sensitive medium-sensitive silver iodobromide emulsion/In<no-logenated excellent grains with an average grain size of 0.5μ, excellent 709-gelatin Zecten (60g containing JP iodine content: 3 moles), water, stabilizer, ω thinning, etc. were added and mixed, and coated to a dry film thickness of lμ. (@Amount O0≠
97In) 3rd J threat: Emulsion of the coupler used in the 7th layer of the high-sensitivity red-sensitive emulsion layer 1kLi high-sensitivity high-sensitivity iodobromide Q emulsion / # (''-Average grain size of silver halide grains 0.6μ , Trowel 7 (79, containing gelatin tOgY, moderate content 3mol/I/4) gelatin, water, stable part j, coating aid and coating to give a dry film thickness lμ. (Weight 0.( 19/m) 1st layer: Intermediate layer 2.3'-G5ec-octylhydroquinone 200
An emulsion obtained by injecting g into 20 oct of ethyl acetate and stirring at high speed an aqueous gelatin solution/ni 9 and sodium dodecylbenzenesulfonate 209? Further, mix io gelatin, water, and stabilizer.

A small amount was spread so that the dry film thickness was lμ.

5th layer: low-sensitivity glaucoma emulsion layer magenta coupler/-(,2,≠,6-drichlorophenyl)-3-(J-(,2,ψ-di-t-amylphenoxyacetamide)penzamide) -5-pyrazolone 2
The remaining %/layer of the emulsion was similar to that of the rc emulsion obtained in the same way. Content: 3 mol %), seranan, water, solubilizer, coating, cutting, mixing, and coating to give a dry film thickness of λμ (Kanpei o,,
797m2) Layer: Kp, l, C<emulsion of magenta coupler covered with green-sensitive emulsion layer ij layer/ /(!?
Green-sensitive middle-window silver iodobromide emulsion/kl (average grain size O6Jμ, QJ 709, gelatin togt; 7 containing iodine content 3 moles), gelatin, water, stabilizer, coating cutting and mixing dry film thickness 7th layer: Highly sensitive green-sensitive emulsion layer The emulsion of the magenta coupler used in the 5th layer was coated to give a green-sensitive emulsion. Chemical emulsion/kl (8709 with average particle size 0.7μ. Legal content 3 mol qb including gelatin togq)
, gelatin, water, stabilizer, and coating cutting were mixed and coated to a dry film thickness of lμ (coated silver amount θ, da 9/m2) R layer: emulsion used in the first intermediate layer/ Mix with 9fl gelatin, water,
The coating was applied by cutting to a dry film thickness of lμ.

Second layer: Yellow filter layer An emulsion containing yellow colloidal silver was coated to a dry film thickness of lμ.

io) Threat: Low-sensitivity emulsion layer yellow coupler α-(piparoyl)-α-(/-benzyl-terethoxy-3-hydantoinyl)-2-chloro-tardodecyloxycarbonylacetanilide is added to the cyan coupler in the first layer. Instead, use tricresyl phosphate FG/20cC acetate ethyl '7/20
The emulsion prepared by changing Ct/ld to a low-sensitivity iodine bromide emulsion/briquette (average grain size 0.5μ, '@709. gelatin tog, iodine content 3 moles), gelatin, water, stable Agent and coating Cutting and mixing Coated to a dry J# thickness of 2μ (Nenfu Ginriki io, 6 g/m2) 1st/
Layer: Medium-sensitivity blue-sensitivity emulsion layer 1kg of the emulsion of the yellow coupler used in the 1st O layer is mixed into a medium-sensitivity silver iodobromide emulsion/kfl (average grain size 0.
6μ silver 709 gelatin tog legal content 3 mole tI
)) Gelatin, water, stabilizer, coating, cutting and mixing. Coated to a dry film thickness of lμ.

(Amount of coated silver o, tt liquid/m) 12th layer: Yellow coupler emulsion used in the high-sensitivity blue-sensitive emulsion layer io layer/1611';
i"ff Highly sensitive iodobromide emulsion/I&<Average grain size 0.7μ Silver 709 Gelatin 60 minutes Iodine content 3
mol.), gelatin, water, stabilizer, and coating agent were mixed and coated to a dry film thickness of lμ. (Semi-i 1i my reaction amount
0, ≠ 97m 2) 3rd J Soji 12th dk
Instead of J-Korean coupler, use LIV absorption, Yochloro-2-(
2-Hydroxy-3,t-punalphenyl)benzotriazole/! ;g, 2-(,2-hydroxy-
30 g of 5-t-butylphenyl)-2H-benzotriazole, 33 g of 2-(,2-hydroxy-3-5ec-butyl-5-t-duterfe=,nz)-,2H-penztriazole, dodecyl j-(N , N-diethylamino)-2-benzenesulfonyl-λ, goupentagenoate ioog, tricresyl phosphate 200
ct: ethyl acetate, 200cc, sodium dodecylbenzenesulfonate, 209,10 gelatin dissolved in water gLλ
The emulsion obtained by stirring the broth at high speed/H'1104 gelatin, water, and coating cuttings were mixed and coated to a dry film thickness of λμ. (Total U'V absorption coating: 0.!; 9/m2) 1st/Horizontal layer: 1st - protective layer Fine grain emulsion that is not chemically sensitized (grain size 00ljμ
Iodide content: 1 mole) 7a-70 gelatin solution containing silver coated amount: 0.39/rr1 Dry film thickness/μ.

The obtained multilayer coated film is designated as sample A'.

Instead of the yellow coupler emulsion used in the 1st θ layer to the 12th layer, the emulsion used in Samples (B) to (H) used in Example 1 was used, and the original color was used in the 10th to 12th layers. Adjust the coating amount so that the evenness is good, and apply samples B' to il'? Created.

This sample N'~li'7 was exposed with a wedge for grain size measurement, and after the image processing shown in Example 1, it was passed through an anometry 2 of ≠♂μφ using a microdensitometer to determine the graininess. It was measured.

Determine the kLms (graininess) of 8L for each sample.
Table 3 shows the result.

Table 3 A' o, o2r B' θ, 0.2.2 C' 0.01r u' o, oko2 E' θ, θ/♂ ■11' θ, θ17 G' 0.02IIL H' θ, In the compounds of the present invention in θ Nog samples B' to F', a significant improvement in graininess is observed.

Example 4 A multilayer color photosensitive material sample was prepared on a 4° cellulose triacetate film support, each layer having the composition shown below.

1st) Anti-halation layer Gelatin layer containing black colloidal silver -2*: Middle 1) 1 layer! - Gelatin layer containing an emulsified dispersion of D-t-octylhydroquinone 3rd layer: Low red-sensitive emulsion layer Iodobromide emulsion (iodide button: 5 mol) ... Silver coating amount 1. Otsu';j7'm2 Sensitizing dye I・・・・・・・・・・・・ ≠ per 1 mol of button, ri xlo mol sensitizing dye] 1・・・・・・・・・・・・For 1 mole of silver/! r×10 molar coupler EX-ha・θ, θ for 11 mol Coupler EX-j...0.003 mol for silver/mol Cassidy EX-2...o for 1 mol, ooo
Otsu mole No. 11: Emulsion layer iodine silver emulsion (iodide d; / 0 mol %)...
・・・・Lacquer coating/city plan / , If')l 7m2 sensitization 1 to 7;I・・・・・・・・・3×lθ mol sensitizing dye (1・・・・・・・・・・・・/x10 mole coupler E, )(−/・・・0.00 for 91 mole
2 mole coupler EX-, 2...0.02 mole for g/nacelle Coupler EX-3...o, oott for 1 mole of silver
Mol No. 5/Zeng: Intermediate) 6th layer same as the 2nd layer; low green sensitivity emulsion layer iridescent milk? a (iodification; φmol)... old...
Trowel Painted Fine Bones / , , 2 g/m2 Sensitizing Dye m・・・・・・・・・JfXlo Sensitizing Dye for 1 mole of Sensitivity ■・・・・・・・・・Mt. λX for 1 mole of iron
10 mole coupler EX-Hiroshi...0.05 mole for 1 mole of silver Coupler EX-T...o, oog for 1 mole of silver
Mol coupler EX-ta... 0.00/! for 1 mole!
Moruya 71 葎; High sense, modest feeling milk cutting layer iodobromide armor emulsion (iodizing force: and mole)...
Silver coating amount 7.397m2 Sensitizing dye 1 ■・・・・・・・・・3×10 moles per 1 mole of silver Sensitizing dye ■・・・・・・River: per 1 mole of rice cake Te/0
．． 2x10 mole coupler EX-7...0.0/7 for ων1 mole
Molar coupler EX-6...0.003 moles per 1 mole of button Coupler gx-io...0.000 per mole of silver
3 mol rth layer: yellow filter single layer seranan in water solution with yellow colloid button and 2,5-di-t-
Emulsification of octylhydroquinone 1; Ceratin layer containing resin and alcohol 2nd layer; 18-sensitivity-D-sensitivity emulsion layer Natural silver emulsion (Iodide [Co., Ltd.]; 6 mole gate)
・Silver (I1iJii O, 79/m Coupler EX-,!'・・・・・・・・・・・・fJ
θ, +25 moles per mole coupler EA-2・・・・・・・・・・・・θ, 0/j moles per mole 107@: Highly sensitive blue-sensitive emulsion layer natural disaster・菰(Iodization repair: 6 moles) ・・・・・・Anchor coater 0, 1.9/m” Coupler EX-♂・・・・・・・・・・・・@1 mole 0.06 mol 1st/layer; 1st retention layer natural disaster @ (1 mol iodide, average grain size 0.07 μ) ・・・・・・・・・ Silver coating amount 0, 597m2
Gelatin layer 1.2 layer containing an emulsified dispersion of ultraviolet absorption (JV-/); λth protective layer polymethyl methacrylate particles (L11 s.l.

Apply a gelatin layer containing jμ).

In addition to the above composition, each layer contains a gelatin hardening agent 1-1-/
and surfactants were added. The sample prepared as described above was designated as sample 10/.

Preparation of Samples 102 to 107 Samples 102 to 107 were prepared in the same manner as Sample .theta.l, except that the coupler EX-2 in the low green-sensitive emulsion layer of Sample 10/ was changed as shown in the table.

When sample/θl~107 was wedge-exposed with white light and processed as described above, almost the same sensitivity and gradation were obtained. The sharpness (of the green-sensing layer) of these samples
>ii One song was evaluated using TF 4 shifts.

The structural formula of the 8G column used is as follows.

Coupler 1'rX i Coupler 1ru
Coupler EX-1 (E Coupler g, X-7 04H9 Coupler EX-f Coupler EX-Coupler zX-i.

α Coupler iX-/1 CH2 1(-/ CH2=CH-8o 2-C1(2-C(JNil-C
H2IJ V -/ Sensitizing dye l Sensitizing dye ■ Sensitizing dye for sensitizing dye ■ ■ Na5Oa(CH2)3(0(,l12CH2)2 The development process used here is as follows at 3!r0c. child.

1. Color reality... River/dan...
3 minutes 1 second 2 bleaching... River... 6 minutes 3 o seconds 3, water &... 4 mountains 1 group...
3 minutes/! Second 4, fixed, old, group...river■...minute 3
0 seconds 5 Water washing/river... Old... 3
Minutes 15 seconds 6, stable... Dan... Dan, River... 3 minutes/! The composition of the treatment liquid used in the Shoya process is as follows.

Color developer Sodium nitrilotriacetate /, 0g Sodium sulfite Hiro,og Sodium charcoal 30.09 Fukkatori /,≠9 Hydroxylamine Nt acid@co,≠9 ≠-(IN-ether-N-β-hydroxy Ethylamino)-λ-methylaniline nitric acid 1.11 ≠・5 minutes Add water / to the white 7 modified ammonium / lθ, θ9 Aqueous ammonia ('21S) 2! , Occ ethylenediamine-tetraacetic acid sodium ρ fire＾訃; /30.09 Ice last l≠, Oat cut water, □ fixed tetrapolyline order sodium ko, 0g1fi sodium sulfate Hiroshi, θ9 thiocorrosion ammonicum (70≠,)/7ta, θJikyokuiniodicate sodium ≠, gg sword (nbaguchiete, t) As is clear from the table above, what contains the compound of the present invention!
In the comparison of Oc/mm, the MTF value was significantly improved in the range of fishing frequency, and the effect of the present invention is clear.

Executor: Fuji Photo Film Co., Ltd. Procedural Amendment to the Commissioner of the Japan Patent Office 1, Indication of the case: Showa Tata Patent Application No. 2, Name of the invention: Silver halide color photographic light-sensitive material 3, Person making the amendment Relationship to the incident Patent applicant Location 210 Nakanuma, Minamiashigara City, Kanagawa Prefecture Name (52)
0) Fuji Photo Film Co., Ltd. "Guyu;;I Note 2, Subject of amendment: 1. Detailed explanation of the invention" column 5, Contents of amendment: "Detailed explanation of the invention" in the specification. The description in this section has been amended as follows.

1) Page 7, second line from the bottom [The above CouP is usually one coupler core residue of an oil-protected coupler, linked by an appropriate bridging group, and fc
, two coupler core residues, or many coupler core residues attached as side chains to the main chain of the polymer. Examples of polymer cubes 2- are described in U.S. Pat. No. 3.4tjt/, 1.
20 and tt, orO,, 2//. ” and then insert “below”.

2) Page 2j ≠ line and correct it.

Claims (1)

[Scope of Claims] At least one silver halide emulsion layer and the following general '
During the coupling with the oxidized form of the color developer, the coupler residue COIi p and the 5-pyrazolone series ? 11. A halogenated color photographic light-sensitive material comprising a photographic coupler characterized in that a bond connecting the nitrogen atom at the λ-position of the 11L deradical is interposed. General formula (1) (Narita, Coup represents the residue that tastes the hydrogen atom of the active site from the coupler that couples with the oxidized product of the color-forming carrier drug, and 1'' represents -(JCI (2- or -0 〇-, these groups are bonded to Coup1 f) with an oxygen atom, n represents/or Q, Y represents a hydrogen atom or an organic residue with a total carbon number of io or less, and X represents hydrogen atom, alkoxy group, alkylthio group, aryloxy group, arylthio group, arylazo group, nitrogen-containing N-terocyclic group bonded by a desired atom, heterocyclicoxy group, heterocyclic thio group, heterocyclic azo group, acyloxy group or represents a sulfonamide group)