JP2001215667A - Silver halide color photographic sensitive material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a silver halide color photographic sensitive material having good color forming property, ensuring sufficient developed color density and giving a cyan image excellent in color reproducibility and a black ground and to provide a silver halide color photographic sensitive material capable of forming a cyan image which does not cause the change of its hue due to heat and moisture. SOLUTION: Each of the silver halide color photographic sensitive materials contains a cyan coupler of formula C-1, e.g. formula C-2 in a red-sensitive silver halide emulsion layer.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a silver halide color photographic material.

[0002]

2. Description of the Related Art Hitherto, a phenol derivative or a naphthol derivative has been widely used as a cyan image forming coupler used in a silver halide color photographic light-sensitive material (hereinafter, also simply referred to as a light-sensitive material). These, conventionally,
Cyan images obtained from phenol derivatives and naphthol derivatives used as cyan couplers have poor sharpness on the short wavelength side of absorption and have unnecessary absorption (called irregular absorption) in the green region. There was a big problem.

The above problems are dealt with by correcting irregular absorption by masking or the like in the negative, but there is no means for correction in the case of paper, and the color reproducibility is considerably deteriorated. Is the current situation.

Further, dye images obtained from phenol derivatives and naphthol derivatives conventionally used as cyan couplers still have some problems in storage stability. For example, US Pat. No. 2,367,53
Dye images obtained using the 2-acylaminophenol cyan couplers described in JP-A Nos. 1 and 2,423,730 usually have poor heat fastness and are disclosed in U.S. Pat.
9,929 and 2,772,162.
Dye images obtained using 5-diacylaminophenol cyan couplers generally have poor light fastness, and dye images obtained from 1-hydroxy-2-naphthamide cyan coupler generally have poor light and heat fastness. Was enough.

Also, 2,5-diacylaminophenol cyan couplers described in US Pat. No. 4,122,369, JP-A Nos. 57-155538 and 57-157246, and US Pat. No. 3,880 No. 2,661 having a hydroxyl group in the ballast portion described in US Pat.
Even for the 5-diacylaminophenol cyan coupler, a sufficiently satisfactory level has not yet been obtained in terms of fastness to light and heat during long-term storage of the dye image and generation of yellow stain.

For the purpose of solving the above-mentioned problems, Japanese Patent Application Laid-Open Nos. 64-554 and 63-250649 are disclosed.
Nos. 63-250650 and the like, pyrazoloazole-type cyan couplers have been proposed, but they have not yet reached a satisfactory level.

Further, pyrazoloazole type cyan couplers having improved color development and color reproducibility at the same time are disclosed in JP-A-8-17.
No. 1185, No. 8-313360, No. 8-33906
No. 0, etc., but in the fast-moving industry, further improvement in color development and color reproducibility has been desired.

[0008]

SUMMARY OF THE INVENTION Accordingly, a first object of the present invention is to provide a halogenated compound which exhibits a good color developing property, provides a sufficient color forming density, and gives a cyan image excellent in both color reproducibility and black background. An object of the present invention is to provide a silver color photographic light-sensitive material.

It is a second object of the present invention to provide a silver halide color photographic material which forms a cyan image which does not change its hue with respect to heat and temperature.

[0010]

The above objects of the present invention have been attained by the following items 1 to 5.

1. A silver halide color photographic light-sensitive material comprising a cyan coupler represented by the above general formula [C-1] in a red-sensitive silver halide emulsion layer.

2. A silver halide color photographic light-sensitive material comprising a cyan coupler represented by formula (C-2) in a red-sensitive silver halide emulsion layer.

3. A silver halide color photographic light-sensitive material comprising the cyan coupler represented by formula (C-3) in a red-sensitive silver halide emulsion layer.

4. A silver halide color photographic light-sensitive material comprising a cyan coupler represented by the above general formula [C-4] in a red-sensitive silver halide emulsion layer.

[0015] 5. A silver halide color photographic light-sensitive material comprising a cyan coupler represented by the above general formula [C-5] in a red-sensitive silver halide emulsion layer.

Hereinafter, the present invention will be described in more detail. First, the cyan coupler represented by the general formula [C-1] according to the present invention will be described.

In the general formula [C-1], the alkyl group represented by R ₁ is preferably an alkyl group having 1 to 32 carbon atoms, and may be linear or branched. Examples of the linear alkyl group include a methyl group, an ethyl group, a propyl group, an octyl group, and a dodecyl group. Examples of the branched alkyl group include an isopropyl group and tert-
Examples thereof include a butyl group and a 2-ethylexyl group.

The cycloalkyl group represented by R ₁ is preferably a cycloalkyl group having 3 to 12 carbon atoms and may have a branched structure. For example, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, -Methylcyclopropyl group, adamantyl group and the like.

Examples of the aryl group represented by R ₁ include a substituted or unsubstituted phenyl group.

The heterocyclic group represented by R ₁ is preferably a 5- to 7-membered heterocyclic group, for example, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl, 1-pyrrolyl. And a 1-tetrazolidinyl group.

The above-mentioned R ₁ may further have a substituent, and the substituent is not particularly limited. Examples thereof include an alkyl group, a cycloalkyl group, an aryl group, an anilino group,
Acylamino group, sulfonamide group, alkylthio group,
Examples of each group such as an arylthio group and an alkenyl group include a halogen atom and a cycloalkenyl group, an alkynyl group, a heterocyclic group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a phosphono group, Acyl group, carbamoyl group, sulfamoyl group, cyano group, alkoxy group, aryloxy group, heterocyclic oxy group, siloxy group, acyloxy group, alkylsulfonyloxy group, arylsulfonyloxy group, alkylcarbamoyloxy group, arylcarbamoyloxy group, Amino group, alkylamino group, imide group, ureido group, alkylsulfamoylamino group, arylsulfamoylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, alkoxycarbonyl Groups, aryloxycarbonyl groups, heterocyclic thio groups, thioureido groups, carboxyl groups, hydroxyl groups, mercapto groups, nitro groups, sulfo groups, and the like, as well as spiro compound residues, crosslinked hydrocarbon compound residues, and the like. .

In each of the above substituents which R ₁ may have, the alkyl group is preferably an alkyl group having 1 to 32 carbon atoms, and may be linear or branched. As the aryl group, a phenyl group is preferable. Examples of the acylamino group include an alkylcarbonylamino group and an arylcarbonylamino group. As the sulfonamide group,
Examples thereof include an alkylsulfonylamino group and an arylsulfonylamino group. Alkylthio group, the alkyl moiety in the arylthio group, the aryl component is an alkyl group represented by R _1, and an aryl group. The alkenyl group is preferably a group having 2 to 32 carbon atoms, and the cycloalkyl group is preferably a group having 3 to 12 carbon atoms, particularly 5 to 7 carbon atoms. The alkenyl group may be linear or branched. As the cycloalkenyl group, one having 3 to 12 carbon atoms, particularly 5 to 7 carbon atoms, is preferable. Examples of the phosphono group include an alkylphosphono group, an alkoxyphosphono group, an aryloxyphosphono group, and an arylphosphono group; examples of the acyl group include an alkylcarbonyl group and an arylcarbonyl group; examples of the carbamoyl group include an alkylcarbamoyl group and an arylcarbamoyl group. A sulfamoyl group such as an alkylsulfamoyl group or an arylsulfamoyl group; an acyloxy group such as an alkylcarbonyloxy group or an arylcarbonyloxy group; a ureido group such as an alkylureido group or an arylureido group; 5 as a heterocyclic group
7 to 7 members are preferred, specifically, 2-furyl group, 2
-Thienyl group, 2-pyrimidinyl group, 2-benzothiazolyl group, 1-pyrrolyl group, 1-tetrazolidinyl group and the like;
As the heterocyclic oxy group, those having a 5- to 7-membered heterocyclic ring are preferable. For example, 3,4,5,6-tetrahydropyranyl-2-oxy group, 1-phenyltetrazole-5
A heterocyclic thio group is preferably a 5- to 7-membered heterocyclic thio group, for example, a 2-pyridylthio group or a 2-pyridylthio group;
Benzothiazolylthio group, 2,4-diphenoxy-1,
3,5-triazole-6-thio group and the like; siloxy group as trimethylsiloxy group, triethylsiloxy group, dimethylbutylsiloxy group and the like; imide group as succinimide group, 3-heptadecylsuccinimide group and phthalimide group A spiro compound residue such as spiro [3.3] heptane-1-yl; and a crosslinked hydrocarbon compound residue such as bicyclo [2.2.1] heptane-1-yl or tricyclo [3]. .3.1.1] decane-
1-yl, 7,7-dimethyl-bicyclo [2.2.1]
Heptan-1-yl and the like.

The above-mentioned groups may further have a substituent such as a long-chain hydrocarbon group or a non-diffusible group such as a polymer residue.

In the general formula [C-1], R ₁ is preferably an alkyl group or an aryl group.

In the general formula [C-1], the tertiary alkyl group represented by R ₂ is preferably a tertiary alkyl group having 4 to 32 carbon atoms, such as a tert-butyl group and a tert-butyl group. Pentyl group, tert-hexyl group,
Examples thereof include a 1,1-dimethyldecyl group, a 1,1,3,3-tetramethylbutyl group, and a 1-methyl-2-butyl group.

The tertiary cycloalkyl group represented by R ₂ is preferably a tertiary cycloalkyl group having 4 to 12 carbon atoms, such as 1-methylcyclopropyl, 1-methylcyclopentyl, and 1-methylcyclohexyl. And a 1-adamantyl group.

R ₂ described above may further have a substituent, and examples of the substituent include the same substituents as the substituents R ₁ may have.

In the general formula [C-1], R ₂ is preferably a tertiary alkyl group, more preferably tertiary alkyl group.
t-butyl group.

In the general formula [C-1], examples of the alkylene group represented by L ₁ include a methylene group, an ethylene group, a trimethylene group, and a hexamethylene group.

Examples of the arylene group represented by L ₁ include a phenylene group and a naphthylene group.

[0031] L ₁ of the description may be further substituted, may be mentioned the same substituents as the substituent that may be possessed by R ₁ is a substituent, L ₁ is an arylene group At this time, a hydroxyl group is excluded as a substituent.

In the general formula [C-1], L ₁ is preferably an arylene group. In the general formula [C-1],
L ₂ is -NHCO -, - CONH -, - OCO- or represents an -SO ₂ NH-, among them preferably used is -NHCO-.

In the general formula [C-1], n1 represents 0 or 1, but 0 is preferred. In the general formula [C-1], examples of the halogen atom represented by X ₁ include a chlorine atom, a bromine atom, and a fluorine atom.

The group capable of leaving by reaction with the oxidized form of the color developing agent represented by X ₁ includes, for example, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an acyloxy group, a sulfonyloxy group, an alkoxycarbonyloxy group Group, aryloxycarbonyl group, alkyloxalyloxy group, alkoxyoxalyloxy group, alkylthio group, arylthio group, heterocyclic thio group, alkyloxythiocarbonylthio group, acylamino group, sulfonamide group, nitrogen-containing heterocyclic group bonded by N atom Each group includes a ring group, an alkyloxycarbonylamino group, an aryloxycarbonylamino group, a carboxyl group and the like.

Among them, X ₁ is preferably used as a hydrogen atom, a halogen atom, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthio group, an arylthio group, a heterocyclic thio group, or a nitrogen-containing complex bonded with an N atom. Ring group, more preferably a chlorine atom, an alkoxy group,
An aryloxy group, most preferably an alkoxy group or an aryloxy group.

The cyan coupler represented by formula (C-2) according to the present invention will be described.

In the general formula [C-2], R ₃ and R ₅
As the alkyl group represented by the general formula [C-1]
Represents a group having the same meaning as the alkyl group represented by R ₁ .

The cycloalkyl group represented by R ₃ and R ₅ has the same meaning as the cycloalkyl group represented by R ₁ in formula [C-1].

The aryl group represented by R ₃ and R ₅ is the same as the aryl group represented by R ₁ in formula [C-1].

R_ThreeAnd R_FiveAs a heterocyclic group represented by
Is R in the general formula [C-1]. ₁A heterocyclic group represented by
Represents the same group as

The above R ₃ and R ₅ may further have a substituent. As the substituent, R ₃ and R ₅ in the general formula [C-1] may be substituted.
Examples include the same groups as the substituents that ₁ may have.

As R ₃ and R ₅ , respectively, preferably used are an alkyl group and an aryl group.

The substituents represented by R _4a and R _4b are the same as the substituents that R ₁ may have in the general formula [C-1], and the substituents represented by R _4a include: Hydroxyl groups are removed.

R _4a is preferably a halogen atom,
An acylamino group, a sulfonamide group, an alkoxy group, an aryloxy group and an alkylamino group.

R _4b is preferably a halogen atom,
An acylamino group, a sulfonamide group, an alkoxy group, an aryloxy group and an alkylamino group.

L ₃ is —NHCO—, —NHSO ₂ —, —C
ONH -, - COO -, - OCO- or -SO ₂ NH
- represents a, among others, -NHCO- and -NHSO ₂
-Is preferred.

N2 represents an integer of 0 to 2, and n2 is preferably 0. The halogen atom represented by X ₂ is a group having the same meaning as the halogen atom represented by X ₁ in the general formula [C-1].

The group which can be eliminated by reacting with the oxidized form of the color developing agent represented by X ₂ includes the group which is eliminated by reacting with the oxidized form of the color developing agent represented by X ₁ in the general formula [C-1]. Represents a group having the same meaning as the obtained group.

X ₂ is preferably a hydrogen atom, a halogen atom, an alkoxy group, an aryloxy group,
A heterocyclic oxy group, an alkylthio group, an arylthio group, a heterocyclic thio group, a nitrogen-containing composite cyclic group bonded by an N atom,
More preferred are a chlorine atom, an alkoxy group and an aryloxy group, and particularly preferred are an alkoxy group and an aryloxy group.

The cyan coupler of the present invention represented by the general formula [C-3] will be described. The alkyl group represented by R ₆ is a group having the same meaning as the alkyl group represented by R ₁ in the general formula [C-1].

The cycloalkyl group represented by R ₆ has the same meaning as the cycloalkyl group represented by R ₁ in formula [C-1].

The aryl group represented by R ₆ has the same meaning as the aryl group represented by R ₁ in formula [C-1].

The above-mentioned R ₆ may further have a substituent, and the substituent may be R ₁ in the aforementioned general formula [C-1].
And the same groups as the substituents that may be possessed.

In formula [C-3], R ₆ is preferably an alkyl group or an aryl group.

The alkyl group represented by R ₇ , R ₈ , R ₉ and R ₁₀ has the same meaning as the alkyl group represented by R ₁ in formula [C-1].

As the cycloalkyl group represented by R ₇ , R ₈ , R ₉ and R ₁₀ , R ₁ in the general formula [C-1]
Represents a group having the same meaning as the cycloalkyl group represented by

The aryl group represented by R ₇ , R ₈ , R ₉ and R ₁₀ has the same meaning as the aryl group represented by R ₁ in formula [C-1].

The above R ₇ , R ₈ , R ₉ and R ₁₀ may further have a substituent.
-1], the same groups as the substituents that R ₁ may have.

R ₇ , R ₈ , R ₉ and R ₁₀ are preferably an alkyl group, more preferably a methyl group.

The substituent represented by R ₁₁ is not particularly restricted but includes, for example, an alkyl group, a cycloalkyl group, an aryl group, an anilino group, an acylamino group, a sulfonamide group,
Examples of the group include an alkylthio group, an arylthio group, and an alkenyl group.In addition, a cycloalkenyl group, an alkynyl group, a heterocyclic group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a phosphono group, Acyl group, carbamoyl group,
Sulfamoyl group, cyano group, alkoxy group, aryloxy group, heterocyclic oxy group, siloxy group, acyloxy group, alkylsulfonyloxy group, arylsulfonyloxy group, alkylcarbamoyloxy group, arylcarbamoyloxy group, amino group, alkylamino group An imide group, a ureido group, an alkylsulfamoylamino group, an arylsulfamoylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group,
Alkoxycarbonyl group, aryloxycarbonyl group, heterocyclic thio group, thioureido group, carboxyl group,
Examples include hydroxyl, mercapto, nitro, and sulfo groups, as well as spiro compound residues and crosslinked hydrocarbon compound residues.

In each of the above substituents which R ₁₁ may have, the alkyl group is preferably an alkyl group having 1 to 32 carbon atoms, and may be linear or branched. As the aryl group, a phenyl group is preferable. Examples of the acylamino group include an alkylcarbonylamino group and an arylcarbonylamino group. As the sulfonamide group,
Examples thereof include an alkylsulfonylamino group and an arylsulfonylamino group. Alkylthio group, the alkyl moiety in the arylthio group, the aryl component is an alkyl group represented by R _1, and an aryl group. The alkenyl group is preferably a group having 2 to 32 carbon atoms, and the cycloalkyl group is preferably a group having 3 to 12 carbon atoms, particularly 5 to 7 carbon atoms. The alkenyl group may be linear or branched. As the cycloalkenyl group, one having 3 to 12 carbon atoms, particularly 5 to 7 carbon atoms, is preferable. As the phosphono group, an alkylphosphono group,
An alkoxyphosphono group, an aryloxyphosphono group, an arylphosphono group, etc .; an alkylcarbonyl group, an arylcarbonyl group, etc. as an acyl group; an alkylcarbamoyl group, an arylcarbamoyl group, etc. as a carbamoyl group; Moyl group, arylsulfamoyl group and the like; acyloxy group as alkylcarbonyloxy group and arylcarbonyloxy group and the like; ureido group as alkylureido group,
An arylureido group or the like; a 5- to 7-membered heterocyclic group is preferable, and specific examples thereof include a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, a 2-benzothiazolyl group,
-Pyrrolyl group, 1-tetrazolidinyl group and the like; As the heterocyclic oxy group, those having a 5- to 7-membered heterocyclic ring are preferable, and for example, 3,4,5,6-tetrahydropyranyl-2
-Oxy group, 1-phenyltetrazol-5-oxy group, etc .; As the heterocyclic thio group, a 5- to 7-membered heterocyclic thio group is preferable, for example, a 2-pyridylthio group, a 2-benzothiazolylthio group, 4-diphenoxy-1,3,5-triazole-6-thio group and the like; a siloxy group such as a trimethylsiloxy group, a triethylsiloxy group and a dimethylbutylsiloxy group; a succinimide group as an imide group;
3-heptadecylsuccinimide group, phthalimide group,
Glutarimide group and the like; spiro compound residues such as spiro [3.3] heptane-1-yl; and crosslinked hydrocarbon compound residues as bicyclo [2.2.1] heptane-1-yl and tricyclo [3. 3.1.1] decan-1-yl,
7,7-dimethyl-bicyclo [2.2.1] heptane-
1-yl and the like.

The above groups may further have a substituent such as a long-chain hydrocarbon group or a non-diffusible group such as a polymer residue.

R ₁₁ is preferably an alkyl group or an aryl group, and more preferably an aryl group.

L ₄ is —O—, —NH— or —SO ₂ NH
Represents-, among which -O- and -NH- are preferably used.

The halogen atom represented by X ₃ is a group having the same meaning as the halogen atom represented by X ₁ in the formula [C-1]. Examples of the group capable of leaving by reaction with an oxidized form of the color developing agent represented by X ₃ include compounds represented by the aforementioned general formula [C
In -1] represents the reaction by which leaves group group having the same meaning with an oxidation product of a color developing agent represented by X _1.

X ₃ is a hydrogen atom, a halogen atom,
Preferred are an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthio group, an arylthio group, a heterocyclic thio group, a nitrogen-containing complex ring group bonded with an N atom, and more preferably a chlorine atom, an alkoxy group, an aryloxy group. And particularly preferred are an alkoxy group and an aryloxy group.

The cyan coupler represented by the general formula [C-4] according to the present invention will be described. The substituent represented by R ₁₂ is a group having the same meaning as the substituent which R ₁ in the above formula [C-1] may have.

As R ₁₂ , a halogen atom, an alkoxy group and an aryloxy group are preferred. n3 represents an integer of 0 to 4, and n3 is preferably 1. Further, R ₁₂ is preferably substituted ortho to the acylamino group to which the pyrazolotriazole skeleton is bonded.

The alkyl group represented by R ₁₃ and R ₁₄ has the same meaning as the alkyl group represented by R ₁ in formula [C-1].

The cycloalkyl group represented by R ₁₃ and R ₁₄ has the same meaning as the cycloalkyl group represented by R ₁ in formula [C-1].

The aryl group represented by R ₁₃ and R ₁₄ is the same as the aryl group represented by R ₁ in formula [C-1].

R ₁₃ and R ₁₄ described above may further have a substituent, and the substituent is represented by the above-mentioned general formula [C-1].
And the same groups as the substituents that R ₁ may have.

As the substituent represented by R ₁₅ , general formula [C-
3] represents a group having the same meaning as the substituent represented by R ₁₁ . R ₁₅
May further have a substituent, and examples of the substituent include the same groups as the substituents that R ₁ in the above general formula [C-1] may have.

R ₁₅ is preferably an alkyl group or an aryl group, and more preferably an aryl group.

The halogen atom represented by X ₄ is a group having the same meaning as the halogen atom represented by X ₁ in the general formula [C-1]. Examples of the group capable of leaving by reaction with an oxidized form of the color developing agent represented by X ₄ include compounds represented by the aforementioned general formula [C
In -1] represents the reaction by which leaves group group having the same meaning with an oxidation product of a color developing agent represented by X _1.

X ₄ is a hydrogen atom, a halogen atom,
An alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthio group, an arylthio group, a heterocyclic thio group, a nitrogen-containing complex ring group bonded with an N atom are preferable, and a chlorine atom, an alkoxy group, and an aryloxy group are more preferable. Yes, particularly preferred are an alkoxy group and an aryloxy group.

The cyan coupler of the present invention represented by the general formula [C-5] will be described. The alkyl group represented by R ₁₆ and R ₁₇ is the same as the alkyl group represented by R ₁ in formula [C-1].

The cycloalkyl group represented by R ₁₆ and R ₁₇ is the same as the cycloalkyl group represented by R ₁ in formula [C-1].

The aryl group represented by R ₁₆ and R ₁₇ is the same as the aryl group represented by R ₁ in formula [C-1].

The heterocyclic group represented by R ₁₆ and R ₁₇ is the same as the heterocyclic group represented by R ₁ in formula [C-1].

R ₁₆ and R ₁₇ described above may further have a substituent, and the substituent may be any of the above-mentioned formulas [C-1]
And the same groups as the substituents that R ₁ may have.

At least one of R ₁₆ and R ₁₇ is-
NHCOCH (R ₁₈ ) contains a group represented by SO ₂ R ₁₉ .

R₁₈, R₁₉As an alkyl group represented by
Is R in the general formula [C-1]. ₁Alkyl represented by
Represents a group having the same meaning as the group.

R₁₈, R₁₉As an aryl group represented by
Is R in the general formula [C-1]. ₁Aryl represented by
Represents a group having the same meaning as the group.

R₁₈As a cycloalkyl group represented by
Is R in the general formula [C-1]. ₁Is represented by cycloa
Represents a group having the same meaning as the alkyl group.

R ₁₈ and R ₁₉ may further have a substituent. Examples of the substituent include R _{1 and} R ₁ in the general formula [C-1].
And the same groups as the substituents that may be possessed.

As R ₁₈ , an alkyl group is preferably used. As R ₁₆ , an alkyl group and an aryl group are preferable.

As R ₁₇ , an aryl group is preferable. X
_{As the} halogen atom represented by ₅ , the general formula [C-
1] represents a group having the same meaning as the halogen atom represented by X ₁ . Examples of the group capable of leaving by reaction with an oxidized form of the color developing agent represented by X ₅ include a group capable of leaving by reaction with an oxidized form of the color developing agent represented by X ₁ in the general formula [C-1]. Represents the same group as

X ₅ is a hydrogen atom, a halogen atom,
Preferred are an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthio group, an arylthio group, a heterocyclic thio group, and a nitrogen-containing composite ring group bonded with an N atom, and more preferably a chlorine atom, an alkoxy group, and an aryloxy group. ,
Particularly preferred are an alkoxy group and an aryloxy group.

Hereinafter, the general formula [C-1] according to the present invention will be described.
Specific examples of the cyan coupler represented by any one of [C-5] to [C-5] are shown below, but the present invention is not limited thereto.

[0091]

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[0092]

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[0093]

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[0094]

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[0095]

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[0096]

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[0097]

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[0098]

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[0099]

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[0100]

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[0101]

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[0102]

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[0103]

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[0104]

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[0105]

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[0106]

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[0107]

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[0108]

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[0109]

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[0110]

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[0111]

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[0112]

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[0113]

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[0114]

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[0115]

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[0116]

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Next, the general formula [C-1] of the present invention
Representative examples of the synthesis of cyan couplers represented by formulas [1] to [C-5] are shown below.

<< Synthesis Examples >> (1) Synthesis of Exemplified Compound 1-1 Exemplified Compound 1-1 was synthesized according to Synthesis Example 1 below.

[0119]

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To 50 ml of ethyl acetate were added 3.79 g of compound A and 3.69 g of compound B, and a solution prepared by dissolving 3.46 g of potassium carbonate in 20 ml of water was slowly added thereto under ice-cooling. After the completion of the dropwise addition, the reaction was carried out at room temperature for 2 hours. Thereafter, the aqueous layer was removed and 29% aqueous ammonia was added for 2 hours.
The reaction mixture was further reacted for 3 hours.

After completion of the reaction, the ethyl acetate layer was washed successively with dilute aqueous hydrochloric acid, dilute aqueous sodium bicarbonate and brine, and the solvent was recovered under reduced pressure. The resulting residue was subjected to column chromatography (silica gel, developing solvent: acetic acid). Ethyl / n
-Hexane) and recrystallized from acetonitrile to obtain the desired Exemplified Compound 1-1.
6.37 g (95% yield, melting point: 106-108 ° C)
Obtained.

The structure was confirmed by ¹ H-NMR, IR and mass spectrum. (2) Synthesis of Exemplified Compound 2-15 It was synthesized according to Synthesis Example 2 below.

[0123]

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5.37 g in 50 ml of tetrahydrofuran
Compound C and 1.19 g of pyridine were added under ice-cooling,
To this was slowly added 3.53 g of compound D. After the completion of the dropwise addition, the reaction was carried out at room temperature for 3 hours. After completion of the reaction, 200 ml of ethyl acetate was added for extraction, and the ethyl acetate layer was successively washed with dilute aqueous hydrochloric acid, dilute aqueous sodium bicarbonate and brine, and the solvent was recovered under reduced pressure. The obtained residue was subjected to column chromatography (column chromatography). Purification by silica gel, developing solvent: ethyl acetate / n-hexane) and recrystallization from acetonitrile gave 6.15 g of the desired Exemplified Compound 2-15 (yield 72%, melting point: 132-1).
34 ° C).

The structure was confirmed by ¹ H-NMR, IR and mass spectrum. (3) Synthesis of Exemplified Compound 3-7 It was synthesized according to Synthesis Example 3 below.

[0126]

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4.33 g in 50 ml of tetrahydrofuran
Of compound F and 1.21 g of triethylamine were added,
Under ice cooling, 3.88 g of compound E was slowly added thereto. After the completion of the dropwise addition, the reaction was carried out at room temperature for 3 hours. After completion of the reaction, 200 ml of ethyl acetate was added for extraction, and the ethyl acetate layer was washed with diluted hydrochloric acid and brine in that order, and 2 ml of 29% aqueous ammonia was added to the obtained ethyl acetate layer, and the mixture was further reacted for 3 hours.

After the completion of the reaction, the ethyl acetate layer is washed successively with dilute hydrochloric acid, dilute aqueous sodium hydrogen carbonate and brine, the solvent is recovered under reduced pressure, and the obtained residue is recrystallized from a mixed solvent of acetonitrile and ethanol. As a result, 6.16 g (yield: 83%, melting point: 184 to 185 ° C.) of the target exemplified compound 3-7 was obtained.

The structure was confirmed by ¹ H-NMR, IR and mass spectrum. (4) Synthesis of Exemplified Compound 4-2 It was synthesized according to Synthesis Example 4 below.

[0130]

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4.95 g in 50 ml of tetrahydrofuran
Of compound H and pyridine (1.58 g) were added under ice-cooling.
To this was added 3.92 g of compound G slowly. After the completion of the dropwise addition, the reaction was carried out at room temperature for 3 hours. After completion of the reaction, 200 ml of ethyl acetate was added for extraction, and the ethyl acetate layer was washed with diluted hydrochloric acid and brine in that order, and 2 ml of 29% aqueous ammonia was added to the obtained ethyl acetate layer, and the mixture was further reacted for 3 hours.

After the completion of the reaction, the ethyl acetate layer was washed successively with dilute aqueous hydrochloric acid, dilute aqueous sodium bicarbonate and brine, the solvent was recovered under reduced pressure, and the resulting residue was recrystallized from ethanol to obtain the desired product. Exemplary compound 4-
5.65 g (yield 70%, melting point: 241-243)
° C).

(5) Synthesis of Exemplified Compound 5-12 The compound was synthesized according to Synthesis Example 5 below.

[0134]

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4.61 g in 50 ml of tetrahydrofuran
Of compound J and 1.19 g of pyridine were added, and the mixture was cooled with ice.
To this was slowly added 4.64 g of compound I. After the completion of the dropwise addition, the reaction was carried out at room temperature for 3 hours. After completion of the reaction, 200 ml of ethyl acetate was added for extraction, and the ethyl acetate layer was washed with diluted hydrochloric acid and brine in that order, and 2 ml of 29% aqueous ammonia was added to the obtained ethyl acetate layer, and the mixture was further reacted for 3 hours.

After completion of the reaction, the ethyl acetate layer was washed successively with a dilute hydrochloric acid solution, a dilute aqueous sodium hydrogen carbonate solution and a saline solution, the solvent was recovered under reduced pressure, and the obtained residue was recrystallized from ethanol to obtain the desired product. Exemplary compound 5-
6.85 g of Compound 12 (81% yield, melting point: 164-165)
° C).

The compounds of the general formulas [C-1] to [C
Other cyan couplers represented by -5] can also be synthesized according to the above.

The compounds represented by the general formulas [C-1] to [C
The content of the cyan coupler represented by -5] is usually preferably in the range of 1 × 10 ⁻³ to 1 mol per mol of silver halide, more preferably 1 × 10 ⁻² to 8 × 10 ⁻¹ mol. Range.

Further, the compound represented by the above general formula [C-1] according to the present invention
The couplers represented by the formulas (1) to (C-5) may be used in combination with other types of cyan couplers, and the methods and techniques used when using ordinary dye-forming couplers are similarly applied.

The general formulas [C-1] to [C]
The cyan coupler represented by -5] is used, for example, in negative and positive coupler films and color photographic materials such as color printing paper.

The light-sensitive material using the cyan couplers represented by the general formulas [C-1] to [C-5] according to the present invention, including this color photographic paper, can be used for a single color or a multicolor. For the silver halide color photographic light-sensitive material of the present invention, the general formulas [C-1] to [C-
The cyan coupler represented by 5) is contained in a red-sensitive silver halide emulsion layer.

The silver halide color photographic light-sensitive material of the present invention has a dye image forming structural unit having photosensitivity in each of the three primary color regions of the spectrum. Each structural unit can be composed of a single layer or multiple emulsion layers sensitive to certain regions of the spectrum. The constituent layers of the light-sensitive material, including the layers of the image forming constituent units, can be arranged in various orders as known in the art.

As a typical example of the silver halide color photographic light-sensitive material of the present invention, a cyan dye image-forming structural unit comprising at least one red-sensitive silver halide emulsion layer containing at least one cyan coupler ( At least one of the cyan couplers has the general formula [C
-1] to [C-5]. ), A magenta dye image-forming unit comprising at least one green-sensitive silver halide emulsion layer containing at least one magenta coupler, from at least one blue-sensitive silver halide emulsion layer containing at least one yellow coupler. The yellow dye image forming structural unit is supported on a support.

In the silver halide color photographic light-sensitive material of the present invention, additional layers such as a filter layer, an intermediate layer, a protective layer,
It may have an undercoat layer or an undercoat layer.

The general formulas [C-1] to [C]
In order to incorporate the cyan coupler represented by formula (5) into the emulsion, a conventionally known method can be applied. For example, tricresyl phosphate, a high boiling organic solvent having a boiling point of 175 ° C. or more such as dibutyl phthalate or butyl acetate,
A low-boiling point solvent such as butyl propionate alone or, if necessary, in a mixture thereof may contain the cyan couplers represented by the general formulas [C-1] to [C-5] according to the present invention alone or After mixing and dissolving, the mixture is mixed with a gelatin aqueous solution containing a surfactant, and then emulsified by a high-speed rotation mixer or a colloid mill or the like, and then added to silver halide to prepare a silver halide emulsion used in the present invention. can do.

The compounds represented by the above general formulas [C-1] to [C
-5] The silver halide composition preferably used for a photosensitive material using a cyan coupler represented by the following formula:
There is silver chlorobromide or silver chloroiodobromide. Further, a combination mixture such as a mixture of silver chloride and silver bromide may be used. That is, when a silver halide emulsion is used for color photographic paper, particularly fast developability is required. Therefore, the silver halide preferably contains a chlorine atom as a halogen composition, and at least 1 mol% of silver chloride is used. Particularly preferred is silver chloride, silver chlorobromide or silver chloroiodobromide.

The silver halide emulsion is chemically sensitized by a conventional method. Further, it can be optically sensitized to a desired wavelength range. Silver halide emulsions are known as antifoggants or stabilizers in the photographic industry for the purpose of preventing fogging during the production process of photosensitive materials, storage columns, or photographic processing, and / or stably maintaining photographic performance. Can be added.

The compounds represented by the above general formulas [C-1] to [C
Silver halide color photographic light-sensitive materials using a cyan coupler represented by formula (5)] include color fogging inhibitors, dye image stabilizers, ultraviolet light inhibitors, antistatic agents, matting agents which are usually used in light-sensitive materials. And various additives such as a surfactant.

Regarding these, for example, Research Disclosure (Research Disclosure)
e) The description in Vol. 176, pp. 22-31 (December 1978) can be referred to.

The compounds represented by the general formulas [C-1] to [C
The silver halide color photographic light-sensitive material containing a cyan coupler represented by -5] can form an image by performing a color development process known in the art. Also,
The silver halide color photographic light-sensitive material of the present invention can contain a color developing agent in the hydrophilic colloid layer as the color developing agent itself or as a precursor thereof, and can be processed by an alkaline activation bath.

The color photographic light-sensitive material of the present invention is subjected to bleaching and fixing after color development. The bleaching process may be performed simultaneously with the fixing process. After the fixing process, a washing process is usually performed. Further, a stabilization treatment may be performed as an alternative to the water washing treatment, or both may be used in combination.

[0152]

EXAMPLES The present invention will be described with reference to examples, but the present invention is not limited to these examples.

Example 1 The following emulsion layer and protective layer were sequentially coated on a paper support laminated on both sides with polyethylene from the support side to prepare a red-sensitive silver halide color photographic light-sensitive material sample 101. Unless otherwise specified, the amount of the compound added is the amount per 1 m ² (silver halide is converted to silver).

First layer: Emulsion layer (red-sensitive emulsion layer) Gelatin 1.3 g Red-sensitive silver chlorobromide emulsion (containing 99.5 mol% of silver chloride) 0.21 g Comparative coupler a 9.1 × 10 ^-4 mol Second layer: protective layer Gelatin 0.50 g 2,4-dichloro-6-hydroxy-s-triazine sodium salt 0.017 g per g of gelatin Next, in sample 101, comparative coupler a was used as a coupler shown in Table 1 (addition amount). Samples 102 to 113 were prepared in exactly the same manner as in Sample 101 except that the amount was reduced to 50 mol% of the comparative coupler a).

[0155]

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[0156]

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[0157]

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Each of the samples 101 to 113 obtained above was subjected to a wedge exposure according to a conventional method, and then subjected to development processing in the following processing steps.

<< Development Processing >> Processing Step Temperature Time Color Development 35.0 ± 0.3 ° C. 45 seconds Bleaching and Fixing 35.0 ± 0.5 ° C. 45 seconds Stabilization 30-34 ° C. 90 seconds Drying 60-80 60 ° C. << Color developing solution >> Pure water 800 ml Triethanolamine 10 g N, N-diethylhydroxylamine 5 g Potassium bromide 0.02 g Potassium chloride 2 g Potassium sulfite 0.3 g 1-hydroxyethylidene-1,1-diphosphonic acid 1. 0 g Ethylenediaminetetraacetic acid 1.0 g Catechol-3,5-disulfonic acid disodium salt 1.0 g Diethylene glycol 10 g N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 4.5 g Fluorescence Brightener (4,4'-diaminostilbene sulfonic acid derivative) 1.0 g Potassium carbonate The is added to make 1 liter 7g water, adjusted to pH = 10.10.

<< Bleaching-fixing solution >> Ammonium ferric ethylenediaminetetraacetate dihydrate 60 g Ethylenediaminetetraacetic acid 3 g Ammonium thiosulfate (70% aqueous solution) 100 ml Ammonium sulfite (40% aqueous solution) 27.5 ml Water was added to bring the total volume to 1 liter. PH is adjusted to 5.7 with potassium carbonate or glacial acetic acid.

<< Stabilizing Solution >> 5-chloro-2-methyl-4-isothiazolin-3-one 0.2 g 1,2-benzisothiazolin-3-one 0.3 g ethylene glycol 1.0 g 1-hydroxyethylidene-1 1,1-diphosphonic acid 2.0 g o-phenylphenol sodium 1.0 g ethylenediaminetetraacetic acid 1.0 g ammonium hydroxide (20% aqueous solution) 3.0 g fluorescent whitening agent (4,4'-diaminostilbenesulfonic acid derivative) 1 Add 0.5 g water to make the total volume 1 liter, and adjust the pH to 7.0 with sulfuric acid or potassium hydroxide.

<< Evaluation Method >> (Highest Density) Samples 101-113 Developed Above
The maximum concentration (Dmax) was measured using a densitometer (Model KD-7 manufactured by Konica Corporation).

(Heat Resistance, Humidity (Dye Residual Rate)) Further, the above-mentioned developed samples were subjected to high temperature and high humidity (85 ° C., 60% R).
H) The sample was allowed to stand in an atmosphere for 21 days, and the dye image was examined for heat resistance and moisture resistance. However, the heat resistance and moisture resistance of the dye image are represented by the residual ratio (%) of the dye after the heat resistance and humidity test with respect to the initial density of 1.0.

The results are shown in Table 1.

[0165]

[Table 1]

From the results shown in Table 1, Samples 104 to 113 using the cyan couplers represented by the general formulas [C-1] to [C-5] according to the present invention correspond to Sample 101 using the comparative coupler a. In comparison with the above, even if the used amount is 50 mol% (reduced to the equivalent amount of × (１ ／) mol), the Dm is equal to or more than that.
ax, and it is clear that the residual ratio of the dye is high, and that it is excellent in color developability, heat resistance and moisture resistance. On the other hand, samples 102 and 103 using comparative couplers b and c were 50 mol%
(Reduced to × (１ ／) mole equivalent), Dm
It can be seen that the value of ax is low and the coloring property is inferior.

Example 2 Polyethylene was laminated on one side of a paper support, and polyethylene having titanium oxide was laminated on the other side. On the support, each layer having the following constitution was replaced with a polyethylene layer containing titanium oxide. To prepare a sample 201 of a silver halide color photographic light-sensitive material. The coating solution was prepared as follows.

<< First Layer Coating Solution >> Yellow coupler (Y-
1) 26.7 g, dye image stabilizer (ST-1)
0g, dye image stabilizer (ST-2) 6.67g, additive (HQ-1) 0.67g, irradiation prevention dye (AI-3), high boiling point organic solvent (DNP) 6.67g and ethyl acetate 60 ml was added and dissolved, and this solution was emulsified and dispersed in 220 ml of a 10% aqueous gelatin solution containing 7 ml of 20% surfactant (SU-1) using an ultrasonic homogenizer to prepare a yellow coupler dispersion. This dispersion was mixed with a blue-sensitive silver halide emulsion (containing 8.68 g of silver) prepared under the following conditions to prepare a first layer coating solution.

Coating solutions for the second to seventh layers were prepared in the same manner as the coating solution for the first layer. (H-1) was added to the second and fourth layers as a hardener, and (H-2) was added to the seventh layer. Surfactants (SU-2) and (SU-3) were added as coating aids to adjust the surface tension. The amount added in the silver halide color photographic light-sensitive material indicates the number of grams per 1 m ² unless otherwise specified.

[0170]

[Table 2]

[0171]

[Table 3]

[0172]

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[0173]

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[0174]

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[0175]

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[0176]

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[0177]

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[0178]

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<< Preparation of Blue-Sensitive Silver Halide Emulsion >> 40 ° C.
The following (solution A) and (solution B) were added in 1000 ml of a 2% aqueous gelatin solution kept at a temperature of pAg = 6.5 and pH = 3.0.
Over 30 minutes while controlling at the same time.
Solution) and (D Solution) were simultaneously added over 180 minutes while controlling pAg = 7.3 and pH = 5.5. The pH was controlled using an aqueous solution of sulfuric acid or sodium hydroxide.
For control of pAg, a control solution having the following composition was used. The composition of the control solution is a mixed halide salt aqueous solution composed of sodium chloride and potassium sulfide, the ratio of chloride ions to bromide ions is 99.8: 0.2, and the concentration of the control solution is A
When mixing the liquid and the liquid B, 0.1 mol / liter, C
The liquid and the liquid D were mixed at 1 mol / liter.

(Solution A) 3.42 g of sodium chloride 0.03 g of potassium bromide Water was added to make up to 200 ml (Solution B) 10 g of silver nitrate was added to water to make up to 200 ml (Solution C) 102.7 g of sodium chloride odor 1.0 g of potassium chloride was added to make up to 600 ml with water (Solution D) 300 g of silver nitrate was added to make up to 600 ml with water. After desalting, the mixture was mixed with an aqueous gelatin solution to give an average particle size of 0.85.
A monodisperse cubic emulsion EMP-1 having a thickness of 9 μm, a coefficient of variation (σ / F) of 0.07 and a silver chloride content of 99.5 mol% was obtained.

The emulsion EMP-1 was chemically ripened at 50 ° C. for 90 minutes using the following compound to obtain a blue-sensitive silver halide emulsion (Em-B).

Sodium thiosulfate 0.8 mg / mol AgX Chloroauric acid 0.5 mg / mol AgX Stabilizer STAB-1 6 × 10 ⁻⁴ mol / mol AgX Sensitizing dye BS-1 4 × 10 ⁻⁴ mol / mol AgX Sensitizing dye BS-2 1 × 10 ^-4 mol / mol AgX << Preparation of green-sensitive silver halide emulsion >> (solution A) and (solution B)
The average particle diameter was 0.43 μm in the same manner as in EMP-1 except that the addition time of (C) and (C solution) and (D solution) were changed.
m, coefficient of variation (σ / F) = 0.08, silver chloride content 9
A 9.5 mol% monodispersed cubic emulsion EMP-2 was obtained.

The following compound was used for EMP-2 using the following compound.
Chemical ripening was performed at 5 ° C. for 120 minutes to obtain a green-sensitive silver halide emulsion (Em-G).

Sodium thiosulfate 1.5 mg / mol AgX Chloroauric acid 1.0 mg / mol AgX Stabilizer STAB-1 6 × 10 ⁻⁴ mol / mol AgX Sensitizing dye GS-1 4 × 10 ⁻⁴ mol / mol AgX << Preparation of Red-Sensitive Silver Halide Emulsion >> (Solution A) and (Solution B)
The average particle size was 0.50 μm in the same manner as in EMP-1 except that the addition time of (C) and (C solution) and (D solution) were changed.
m, coefficient of variation (σ / F) = 0.08, silver chloride content 9
A 9.5 mol% monodispersed cubic emulsion EMP-3 was obtained.

EMP-3 was synthesized by using the following compound.
Chemical ripening was performed at 0 ° C. for 90 minutes to obtain a red-sensitive silver halide emulsion (Em-R).

Sodium thiosulfate 1.8 mg / mol AgX chloroauric acid 2.0 mg / mol AgX Stabilizer STAB-1 6 × 10 ⁻⁴ mol / mol AgX Sensitizing dye RS-1 1 × 10 ⁻⁴ mol / mol AgX

[0187]

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The variation coefficient is represented by the following equation.

[0189]

(Equation 1)

In the formula, γi represents the particle diameter, and ni represents the particle diameter γ.
i represents the number of particles. Next, in Sample 201, the cyan couplers Ca and Cb in the fifth layer are represented by the couplers shown in Table 4 (the amount added is reduced to 50 mol% of the total number of moles of the comparative couplers Ca and Cb). Sample 201 except that
Samples 202 to 213 were produced in exactly the same manner as described above.

[0191]

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[0192]

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<< Evaluation Method >> (Measurement of Maximum Density (Dmax)) The obtained sample was exposed to wedges in the same manner as in Example 1, developed, and the maximum density (Dmax) of the red-sensitive layer was measured.

(Evaluation of Color Reproducibility and Black Background) The samples 201 to 213 were evaluated for color reproducibility and black background by the following methods.

First, a color negative film (Konica Color JX-400: manufactured by Konica Corporation) and a camera (Konica F
T-1 MOTOR: manufactured by Konica Corporation) was used to photograph a Macbeth color checker. Subsequently, a color negative development process (CNK-4: manufactured by Konica Corporation) was performed, and the obtained negative image and the Konica Color Printer CL-P were used.
The above sample 201 was prepared by using 2000 (made by Konica Corporation).
To 213 were printed in a size of 82 mm × 117 mm (developed after exposure) to obtain practical prints. Printer conditions at the time of printing were set for each sample so that the gray on the color checker became gray on the print.

With respect to the obtained practical prints, color reproducibility and black background were visually evaluated according to the following criteria.

(Color reproducibility) 5: Color reproducibility (hue and chroma) is clearly superior to the comparative sample 4: Color reproducibility (hue and chroma) is superior to the comparative sample 3: Color reproducibility (hue and saturation) is equivalent to the comparative sample 2: Color reproducibility (hue and saturation) is inferior to the comparative sample 1: Color reproducibility (hue and saturation) is comparative sample 5: Black background (hue and density) is clearly superior to the comparative sample 4: Black background (hue and density) is superior to the comparative sample 3 : Black background (hue and density) is equivalent to the comparative sample 2: Black background (hue and density) is inferior to the comparative sample 1: Black background (hue and density) is clearly inferior to the comparative sample Table 4 shows the results.

[0198]

[Table 4]

From Table 4, it can be seen that the sample of the present invention exhibited better color development, sufficient color density was obtained, absorption in the blue and green regions was reduced, and color reproducibility was higher than that of the comparative sample. It can be seen that the improvement is remarkable, and the hue change of the dye image due to heat and humidity is small.

More specifically, the comparative coupler C-
Sample 201 using a and Cb is extremely insufficient in color reproducibility. Samples 202 and 203 using comparative couplers d and e in an amount of 50 mol% of the total number of moles of comparative couplers Ca and Cb showed that although cyan color and cyan color were improved although color reproducibility of blue was significantly improved. The color reproducibility is not sufficiently improved, and the black density is not sufficient because the maximum density is low.

In contrast, the samples 204 to 213 of the present invention
(The amount used is reduced to 50 mol% of the total number of moles of the comparative couplers Ca and Cb.) The color reproducibility is good for all of cyan, blue and green, the color developability is good and the maximum density is high. It can be seen that it is also high and has excellent black background.

[0202]

According to the present invention, firstly, there is provided a silver halide color photographic light-sensitive material having a good color-forming property, a sufficient color-forming density, and a cyan image excellent in color reproducibility and black background. I was able to.

Second, a silver halide color photographic light-sensitive material capable of forming a cyan image having no change in hue with respect to heat and temperature can be provided.

 ──────────────────────────────────────────────────の Continuing on the front page (72) Inventor Chen ▲ 流 ▼ Style Konica Corporation, 1 Sakura-cho, Hino-shi, Tokyo In-house (72) Inventor Tomohiro Oshiyama 1st Konica Corporation, Sakura-cho, Hino-shi, Tokyo F-term (Reference) 2H016 BE01 BF06 BG00 BG02

Claims (5)

[Claims] 1. A silver halide color photographic material comprising a red-sensitive silver halide emulsion layer containing a cyan coupler represented by the following formula [C-1]. Embedded image [In the formula, R ₁ represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, and R ₂ represents a tertiary alkyl group or a tertiary cycloalkyl group. L ₁ represents an alkylene group or an arylene group. However, when L ₁ is an arylene group, a hydroxyl group is excluded as a substituent. L ₂ is -NHCO -, - CONH -, - OCO- or -SO
₂ represents NH—, and n1 represents 0 or 1. X ₁ represents a hydrogen atom, a halogen atom or a group which can be eliminated by reaction with an oxidized form of a color developing agent. ] 2. A silver halide color photographic material comprising a red-sensitive silver halide emulsion layer containing a cyan coupler represented by the following formula [C-2]. Embedded image [In the formula, R ₃ represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group. R _4a represents a substituent other than a hydroxyl group, R _4b represents a substituent, and R ₅ represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group. L ₃ is _{-NHCO -, - NHSO 2 -,} - CONH
-, - COO -, - OCO- or an -SO ₂ NH-, n2 represents an integer of 0 to 2. X ₂ represents a hydrogen atom, a halogen atom or a group which can be eliminated by reaction with an oxidized form of a color developing agent. ] 3. A shea represented by the following general formula [C-3].
Coupler in the red-sensitive silver halide emulsion layer
A silver halide color photographic light-sensitive material comprising: Embedded image[Wherein, R₆Represents an alkyl group, a cycloalkyl group or
Represents a reel group. R₇, R ₈, R₉And R_TenIs hydrogen field
Group, an alkyl group, a cycloalkyl group or an aryl group
Where at least three of these represent groups other than hydrogen atoms
Represent. R₁₁Represents a substituent;_FourIs -O-, -NH- or
Or -SO_TwoRepresents NH-. X_ThreeIs a hydrogen atom, a halogen atom
Can be desorbed by reaction with oxidized form of a developing agent or a color developing agent
Represents a group. ] 4. A silver halide color photographic material comprising a red-sensitive silver halide emulsion layer containing a cyan coupler represented by the following formula [C-4]. Embedded image [Wherein, R ₁₂ represents a substituent, and R ₁₃ and R ₁₄ represent a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group. R ₁₅ represents a substituent, and n3 represents an integer of 0 to 4. X ₄ represents a hydrogen atom, a halogen atom or a group which can be eliminated by reaction with an oxidized form of a color developing agent. ] 5. A silver halide color photographic light-sensitive material comprising a cyan coupler represented by the following formula [C-5] in a red-sensitive silver halide emulsion layer. Embedded image [Wherein, R ₁₆ and R ₁₇ represent an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, at least one of which contains a group represented by —NHCOCH (R ₁₈ ) SO ₂ R _19] I do. R ₁₈ represents an alkyl group, a cycloalkyl group or an aryl group, and R ₁₉ represents an alkyl group or an aryl group. X ₅ represents a hydrogen atom, a halogen atom or a group which can be eliminated by reaction with an oxidized form of a color developing agent. ]