JP2002182347A - 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 developing property, ensuring sufficiently high developed color density, having sharply limited absorption and little absorption in blue and green regions, that is, superior spectral absorption characteristics and giving a clear cyan image and to provide a silver halide color photographic sensitive material capable of further forming a cyan image having light stability and not causing early yellow stain. SOLUTION: The silver halide color photographic sensitive materials contains a coupler of formula (1).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a silver halide color photographic light-sensitive material. About.

[0002]

BACKGROUND OF THE INVENTION As cyan image forming couplers used in silver halide color photographic light-sensitive materials, phenols or naphthols have been widely used.
However, cyan images obtained from conventionally used phenols and naphthols have a large problem in color reproduction such that the sharpness of absorption on the short wavelength side is poor and unnecessary absorption, that is, irregular absorption is also present in the green region. . This allows
In the negative, irregular absorption must be corrected by masking or the like, and in the case of paper, there is no correction means, and the color reproducibility is considerably deteriorated at present.

[0003] The dye images obtained from conventionally used phenols and naphthols still have some problems in the storage stability. For example, dye images obtained from the 2-acylaminophenol cyan couplers described in U.S. Pat. Nos. 2,367,531 and 2,423,730 generally have poor heat fastness, and are described in U.S. Pat. No. 2,369,929. The dye image obtained from the 2,5-diacylaminophenol cyan coupler described in No. 2,772,162 generally has poor light fastness, and the dye image obtained from the 1-hydroxy-2-naphthamide cyan coupler is Generally, both light and heat fastness are insufficient. U.S. Pat. No. 4,122,369;
2,5-diacylaminophenol cyan couplers described in 155538 and 57-157246 and 2,5-diacylamino having a hydroxyl group in a ballast portion described in U.S. Pat. No. 3,880,661. The phenol cyan coupler has not yet reached a satisfactory level in terms of fastness to light and heat and generation of yellow stain for long-term preservation of the dye image.

For the purpose of solving these problems, Japanese Patent Application Laid-Open Nos. 64-554 and 63-250649,
JP-A-63-250650 proposes a pyrazoloazole-type cyan coupler. Further, pyrazoloazole type cyan couplers having improved color development and color reproducibility simultaneously are disclosed in JP-A-8-171185 and JP-A-8-31380.
No. 8-339060, etc., although some improvements are seen in terms of color development and color reproducibility,
In the fast-moving photographic industry, the level was not yet satisfactory, and furthermore it was not satisfactory in terms of light fastness, especially in the early yellow stain.

[0005]

DISCLOSURE OF THE INVENTION The present invention has been made in view of the above circumstances, and a first object of the present invention is to provide a good color developing property, a sufficient color forming density, and a sharp absorption. Another object of the present invention is to provide a silver halide color photographic light-sensitive material which provides a clear cyan image excellent in so-called spectral absorption characteristics with little absorption in blue and green regions. It is a second object of the present invention to provide a silver halide color photographic light-sensitive material capable of forming a cyan image which does not generate light stability, particularly, no initial yellow stain.

[0006]

The inventors of the present invention have made various studies and found that good stability to light, in particular, no initial yellow stain is generated, and further excellent color reproducibility,
In addition, the present inventors have succeeded in finding a pyrazoloazole-type cyan coupler having good coloring properties, and have completed the present invention.

The above object of the present invention is achieved by the following constitution. 1. A silver halide color photographic material comprising a coupler represented by the formula (1).

[0008] 2. A silver halide color photographic material comprising a coupler represented by the formula (2).

3. A silver halide color photographic material comprising a coupler represented by the formula (3).

[0010] 4. A silver halide color photographic light-sensitive material comprising a coupler represented by the formula (4).

5. A silver halide color photographic light-sensitive material comprising a coupler represented by the formula (5).

6. A silver halide color photographic material comprising a coupler represented by the formula (6).

Hereinafter, the present invention will be described in detail. Coupler represented by formulas (1) to (6) of the present invention (hereinafter also referred to as coupler of the present invention or cyan coupler of the present invention)
Will be described in detail.

In the general formula (1), R ₁ represents an acylamino group, a sulfonamide group, a ureido group, a sulfonyl group, a carbamoyl group, a sulfamoyl group, an imide group,
Represents an oxycarbonylamino group and an oxycarbonyl group.

The acylamino group represented by R ₁ includes:
Palmitoylamino, stearoylamino, 2- (2,
Each group such as 4-di-t-pentylphenoxy) butanoylamino is exemplified.

Examples of the sulfonamide group represented by R ₁ include dodecylsulfonylamino and 4-dodecyloxybenzenesulfonylamino.

The ureido group represented by R ₁ includes dodecylaminocarbonylamino, di (2-ethylhexyl) aminocarbonylamino, 4- (2,4-di-t-
Pentylphenoxy) butylaminocarbonylamino and the like.

Examples of the sulfonyl group represented by R ₁ include dodecylsulfonyl, 4-dodecyloxybenzenesulfonyl, isohexadecylsulfonyl and the like.

As the carbamoyl group represented by R ₁ ,
2-ethylhexylaminocarbonyl, 4- (2,4-
Examples of such groups include di-t-pentylphenoxy) butylaminocarbonyl and tertiarybutylaminocarbonyl.

Examples of the sulfamoyl group represented by R ₁ include 2-ethylhexylaminosulfonyl, 4- (2,
Examples of such groups include 4-di-t-pentylphenoxy) butylaminosulfonyl and tertiarybutylaminosulfonyl.

Examples of the imide group represented by R ₁ include 3-octadecyl succinimide and 3-octadecenyl succinimide.

Examples of the oxycarbonylamino group represented by R ₁ include dodecyloxycarbonylamino, hexadecyloxycarbonylamino and the like.

Examples of the oxycarbonyl group represented by R ₁ include dodecyloxycarbonyl and hexadecyloxycarbonyl.

R ₁ may further have a substituent, and the substituent is not particularly limited.
Aryl, anilino, acylamino, sulfonamide,
Examples of each group include alkylthio, arylthio, alkenyl, and cycloalkyl.In addition, halogen atoms and cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, alkoxy, aryloxy, Heterocyclic oxy, siloxy, acyloxy, sulfonyloxy, carbamoyloxy, amino, alkylamino, imide, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, heterocyclic thio, thioureido, Examples include groups such as carboxy, hydroxy, mercapto, nitro, and sulfo, as well as spiro compound residues and bridged hydrocarbon compound residues.

R ₁ is preferably an acylamino group, a sulfonamide group, a ureido group and an oxycarbonyl group, and more preferably an acylamino group and a sulfonamide group.

R ₂ represents an alkyl group, an aryl group or a heterocyclic group. The alkyl group preferably has 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, a tertiary butyl group, and a cyclohexyl group.

Examples of the aryl group include a substituted or unsubstituted phenyl group.

The heterocyclic group is preferably a 5- to 7-membered heterocyclic group, specifically, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl, 1-pyrrolyl, 1-tetrazolyl. A lysine lyl group and the like can be mentioned.

R ₂ may further have a substituent, and the substituent is not particularly limited.
Aryl, anilino, acylamino, sulfonamide,
Examples of each group include alkylthio, arylthio, alkenyl, and cycloalkyl.In addition, halogen atoms and cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, alkoxy, aryloxy, Heterocyclic oxy, siloxy, acyloxy, sulfonyloxy, carbamoyloxy, amino, alkylamino, imide, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, heterocyclic thio, thioureido, Examples include groups such as carboxy, hydroxy, mercapto, nitro, and sulfo, as well as spiro compound residues and bridged hydrocarbon compound residues.

In the general formula (1), R ₂ is preferably an alkyl group or an aryl group, more preferably an aryl group.

[0031] In the general formula (1) n1 represents an integer of from 1 to 4, when n1 is 2 or more, R ₁ may be different even in the same.

In the general formula (1), X ₁ represents a halogen atom, an alkyloxy group, an aryloxy group or a heterocyclic oxy group.

Examples of the halogen atom represented by X ₁ include a chlorine atom and a bromine atom.

Examples of the alkyloxy group represented by X ₁ include methoxy, ethoxy and the like.

Examples of the aryloxy group represented by X ₁ include phenoxy, p-methylphenoxy and the like.

The heterocyclic oxy group represented by X ₁ includes
Examples of each group include 2-pyridyloxy and 3-pyridyloxy.

In the general formula (1), X ₁ is preferably a halogen atom, an alkyloxy group or an aryloxy group, more preferably a chlorine atom or an aryloxy group.

In the general formula (2), R ₃ and R ₄
Represents a substituent, and the substituent is not particularly limited,
Typically, alkyl, aryl, anilino, acylamino, sulfonamide, alkylthio, arylthio,
Each group such as alkenyl and cycloalkyl is exemplified,
In addition to this, a halogen atom and cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl,
Acyl, carbamoyl, sulfamoyl, cyano, alkoxy, aryloxy, heterocyclic oxy, siloxy, acyloxy, sulfonyloxy, carbamoyloxy,
Amino, alkylamino, imide, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, heterocyclic thio, thioureido, carboxy, hydroxy, mercapto, nitro, sulfo and other groups, And spiro compound residues, bridged hydrocarbon compound residues, and the like.

In the general formula (2), n2 represents an integer from 0 to 4, and when n2 is 2 or more, R ₃ may be the same or different.

In the general formula (2), X ₂ represents a halogen atom, an alkyloxy group, an aryloxy group or a heterocyclic oxy group.

Examples of the halogen atom, alkyloxy group, aryloxy group and heterocyclic oxy group represented by X ₂ include the same groups as those of X _{1 in the} general formula (1).

In the general formula (3), R ₅ represents an alkyl group, an aryl group or a heterocyclic group.

The alkyl group represented by R ₅ preferably has 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. Isopropyl group as the branched alkyl group,
Examples include a tertiary butyl group and a cyclohexyl group. Examples of the aryl group include a substituted or unsubstituted phenyl group. The heterocyclic group is preferably a 5- to 7-membered heterocyclic group, specifically, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl, 1-pyrrolyl, 1-tetrazolidinelyl. And the like. R ₅ may further have a substituent, and the substituent is not particularly limited, and examples thereof include the substituents for R ₁ .

In the general formula (3), R ₆ is a hydrogen atom,
Represents an alkyl group, an aryl group and a heterocyclic group.

The alkyl group represented by R ₆ is preferably one 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. Isopropyl group as the branched alkyl group,
Examples include a tertiary butyl group and a cyclohexyl group. Examples of the aryl group include a substituted or unsubstituted phenyl group. The heterocyclic group is preferably a 5- to 7-membered heterocyclic group, specifically, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl, 1-pyrrolyl, 1-tetrazolidinelyl. And the like. R ₆ may further have a substituent, and the substituent is not particularly limited, and examples thereof include the substituents for R ₁ .

R ₆ is preferably an alkyl group, more preferably a branched alkyl group. In the general formula (3), R ₇ represents an alkyl group, an aryl group and a heterocyclic group.

The alkyl group represented by R ₇ preferably has 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. Isopropyl group as the branched alkyl group,
Examples include a tertiary butyl group and a cyclohexyl group. Examples of the aryl group include a substituted or unsubstituted phenyl group. The heterocyclic group is preferably a 5- to 7-membered heterocyclic group, specifically, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl, 1-pyrrolyl, 1-tetrazolidinelyl. And the like. R ₇ may further have a substituent, and the substituent is not particularly limited, and a typical example thereof is the substituent of R ₁ .

R ₇ is preferably an alkyl group or an aryl group, and more preferably an aryl group.

In the general formula (3), X ₃ represents a halogen atom, an alkyloxy group, an aryloxy group or a heterocyclic oxy group.

Examples of the halogen atom, alkyloxy group, aryloxy group and heterocyclic oxy group represented by X ₃ include the same groups as X _{1 in the} general formula (1).

In the general formula (4), R ₈ represents an alkyl group, an aryl group or a heterocyclic group.

The alkyl group represented by R ₈ preferably has 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. Isopropyl group as the branched alkyl group,
Examples include a tertiary butyl group and a cyclohexyl group. Examples of the aryl group include a substituted or unsubstituted phenyl group. The heterocyclic group is preferably a 5- to 7-membered heterocyclic group, specifically, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl, 1-pyrrolyl, 1-tetrazolidinelyl. And the like. R ₈ may further have a substituent, and the substituent is not particularly limited, and examples thereof include the substituents for R ₁ .

In the general formula (4), J represents an alkylene group. As the alkylene group represented by J, for example,
Examples include a methylene group, an ethylene group, and a propylene group. J may further have a substituent, and examples thereof include an alkyl group, an aryl group, and a heterocyclic group.

In the general formula (4), R ₉ represents a substituent, and the substituent is not particularly limited, but typically, alkyl, aryl, anilino, acylamino, sulfonamide, alkylthio, arylthio, alkenyl, Examples of each group include cycloalkyl, and in addition, a halogen atom and cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, alkoxy, aryloxy, heterocyclic oxy, siloxy, Acyloxy, sulfonyloxy, carbamoyloxy, amino, alkylamino, imide, ureido, sulfamoylamino,
Each group such as alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, heterocyclic thio, thioureido, carboxy, hydroxy, mercapto, nitro, and sulfo, as well as spiro compound residues and bridged hydrocarbon compound residues Are also mentioned.

R ₉ is preferably an alkyl group, an aryl group, or a heterocyclic group, and examples thereof include the same groups as R ₂ in the general formula (1).

In the general formula (5), Y ₁ represents a halogen atom. As the halogen atom, a fluorine atom,
Examples include a chlorine atom, a bromine atom and an iodine atom.

In the general formula (5), Y ₁ is preferably a chlorine atom or a bromine atom, more preferably a chlorine atom.

In the general formula (5), R ₁₀ represents a hydrogen atom or a substituent. The substituent is not particularly limited,
Typically, alkyl, aryl, anilino, acylamino, sulfonamide, alkylthio, arylthio,
Each group such as alkenyl and cycloalkyl is exemplified,
In addition, cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, alkoxy, aryloxy, heterocycleoxy, siloxy, acyloxy, sulfonyloxy, carbamoyloxy, amino, alkylamino, imide , Ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, heterocyclic thio, thioureido, carboxy, hydroxy, mercapto, nitro, sulfo and other groups, and spiro compound residue, Bridged hydrocarbon compound residues are also included.

In the general formula (5), R ₁₀ is preferably a hydrogen atom, an acylamino group, a sulfonamide group, a carbamoyl group, an alkoxycarbonyl group or an aryloxycarbonyl group.

[0060] In the general formula (5), n3 is an integer of from 2 to 5, when the 5-n3 is 2 or more, R ₁₀ may be different even in the same.

In the general formula (5), R ₁₁ represents a substituent having a Hammett's substituent constant σp value of −0.3 or more and 1.0 or less. The Hammett's substituent constant [sigma] p value is described in "Chemical Area Special Issue No. 136, Structure-activity relationship of drugs [1]"
Based on the values described on page 103. The substituent having a Hammett's substituent constant σp value of from −0.3 to 1.0 is specifically alkyl, aryl, acylamino, sulfonamide, alkylthio, arylthio, alkenyl, cycloalkenyl, alkynyl, sulfonyl, sulfinyl , Phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, acyloxy, sulfonyloxy, carbamoyloxy, imide, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, heterocyclic thio, thioureido, carboxy, etc. And a halogen atom.

In the general formula (5), R ₁₁ is preferably a substituent having a Hammett's substituent constant σp value of -0.1 to 0.9, particularly preferably a chlorine atom, an acylamino group, a sulfonamide group. , A sulfonyl group, an alkoxycarbonyl group, and an aryloxycarbonyl group.

In the general formula (5), m1 represents an integer from 0 to 5, and when m1 is 2 or more, R ₁₁ may be the same or different.

In the general formula (5), X ₅ represents a halogen atom, an alkyloxy group, an aryloxy group or a heterocyclic oxy group.

The halogen atom represented by X ₅ includes a chlorine atom and a bromine atom.

Examples of the alkyloxy group represented by X ₅ include methoxy, ethoxy and the like.

Examples of the aryloxy group represented by X ₅ include phenoxy and p-methylphenoxy.

The heterocyclic oxy group represented by X ₅ includes
Examples of each group include 2-pyridyloxy and 3-pyridyloxy.

In the general formula (5), X ₅ is preferably a halogen atom, an alkyloxy group or an aryloxy group, more preferably a chlorine atom or an aryloxy group.

In the general formula (6), Y ₂ represents a halogen atom. As the halogen atom, a fluorine atom,
Examples include a chlorine atom, a bromine atom and an iodine atom.

In the general formula (6), Y ₂ is preferably a chlorine atom or a bromine atom, more preferably a chlorine atom.

In the general formula (6), R ₁₂ represents a hydrogen atom or a substituent. The substituent is not particularly limited,
Typically, alkyl, aryl, anilino, acylamino, sulfonamide, alkylthio, arylthio,
Each group such as alkenyl and cycloalkyl is exemplified,
In addition, cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, alkoxy, aryloxy, heterocycleoxy, siloxy, acyloxy, sulfonyloxy, carbamoyloxy, amino, alkylamino, imide , Ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, heterocyclic thio, thioureido, carboxy, hydroxy, mercapto, nitro, sulfo and other groups, and spiro compound residue, Bridged hydrocarbon compound residues are also included.

In the general formula (6), R ₁₂ is preferably a hydrogen atom, an acylamino group, a sulfonamide group, a carbamoyl group, an alkoxycarbonyl or an aryloxycarbonyl.

In the general formula (6), n4 represents an integer from 2 to 5, and when 5-n4 is 2 or more, R ₁₂ may be the same or different.

In the general formula (6), R ¹³ represents a substituent having a Hammett's substituent constant σp value of −0.3 or more and 1.0 or less. The Hammett's substituent constant [sigma] p value is described in "Chemical Area Special Issue No. 136, Structure-activity relationship of drugs [1]"
Based on the values described on page 103. The substituent having a Hammett's substituent constant σp value of from −0.3 to 1.0 is specifically alkyl, aryl, acylamino, sulfonamide, alkylthio, arylthio, alkenyl, cycloalkenyl, alkynyl, sulfonyl, sulfinyl , Phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, acyloxy, sulfonyloxy, carbamoyloxy, imide, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, heterocyclic thio, thioureido, carboxy, etc. And a halogen atom and the like.

In the general formula (6), R ₁₃ is preferably a substituent having a Hammett's substituent constant σp value of -0.1 to 0.9, particularly preferably a chlorine atom, an acylamino group or a sulfonamide group. , A sulfonyl group, an alkoxycarbonyl group, and an aryloxycarbonyl group.

In the general formula (6), m2 represents an integer from 0 to 5, and when m2 is 2 or more, R ₁₃ may be the same or different.

In the general formula (6), X ₆ represents a halogen atom, an alkyloxy group, an aryloxy group or a heterocyclic oxy group.

The halogen atom represented by X ₆ includes a chlorine atom and a bromine atom.

Examples of the alkyloxy group represented by X ₆ include methoxy, ethoxy and the like.

Examples of the aryloxy group represented by X ₆ include phenoxy and p-methylphenoxy.

As the heterocyclic oxy group represented by X ₆ ,
Examples of each group include 2-pyridyloxy and 3-pyridyloxy.

In the general formula (6), X ₆ is preferably a halogen atom, an alkyloxy group or an aryloxy group, more preferably a chlorine atom or an aryloxy group.

Hereinafter, typical specific examples of the couplers represented by formulas (1) to (6) of the present invention are shown, but the present invention is not limited thereto.

[0085]

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[0086]

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[0087]

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[0088]

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[0089]

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[0090]

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[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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Hereinafter, examples of the synthesis of the couplers represented by formulas (1) to (6) of the present invention will be described. (1) Synthesis of Exemplary Coupler (1) -3 Exemplary Coupler (1) -3 was synthesized according to Synthesis Scheme 1.

[0108]

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To 3.74 g (10 mmol) of 1a, 20 ml of toluene and 2.38 g (20 mmol) of thionyl chloride were added and reacted at about 90 ° C. for 4 hours. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 1b.

To 1b obtained above, tetrahydrofuran 40 was added.
ml and add 4.09 g (10 mmol) of 1
c, 2.37 g (30 mmol) of pyridine were added,
The reaction is carried out at room temperature for 2 hours and then at 50 ° C. for 1 hour.
After completion of the reaction, 4 ml of 28% aqueous ammonia is further added, and the mixture is reacted at about 50 ° C. for 4 hours.

After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was acidified by adding ethyl acetate and dilute hydrochloric acid, and the organic layer was extracted and washed three times with water. Thereafter, the solvent was recovered under reduced pressure, and the obtained residue was recrystallized from ethyl acetate-acetonitrile to obtain 6.0 of the intended exemplary coupler (1) -3.
0 g (83% yield) was obtained. The structure is ¹ H-NMR, IR,
Confirmed by Mass spectrum.

(2) Synthesis of Illustrative Coupler (2) -10 Illustrative coupler (2) -10 was synthesized according to Synthetic Scheme 2.

[0113]

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4.11 g (10 mmol) of 2a and 4.
45 g (10 mmol) of 2b was dissolved in 40 ml of tetrahydrofuran, and at room temperature, dicyclohexylcarbodiimide, 2.06 g (10 mmol) was added.
The reaction is carried out at 40 ° C. for 8 hours. After completion of the reaction, the insolubles were filtered off, the filtrate was concentrated, and ethyl acetate and water were added for extraction.
The solvent is collected under reduced pressure. Then, the obtained residue was recrystallized from ethanol to obtain 5.70 g (yield: 68%) of the objective exemplified coupler (2) -10. The structure is
^It was confirmed by ¹ H-NMR, IR and Mass spectra.

(3) Synthesis of Illustrative Coupler (3) -1 Illustrative coupler (3) -1 was synthesized according to Synthetic Scheme 3.

[0116]

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40 ml of tetrahydrofuran was added to 3.92 g (10 mmol) of 1b, and 3.06 g (1
(0 mmol) of 3a, 2.37 g (30 mmol) of pyridine and 2 hours at room temperature, then 1 hour at 50 ° C.
Let react for hours. After the reaction is completed, 4 ml of 28%
Ammonia water is added, and the reaction is performed at about 50 ° C. for 4 hours.

After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was acidified by adding ethyl acetate and dilute hydrochloric acid, and the organic layer was extracted and washed with water three more times. Thereafter, the solvent was recovered under reduced pressure, and the obtained residue was recrystallized from ethanol to obtain 5.39 g of the objective exemplified coupler (3) -1 (yield: 87).
%)Obtained. The structure was confirmed by ¹ H-NMR, IR and Mass spectra.

(4) Synthesis of Illustrative Coupler (4) -2 Illustrative coupler (4) -2 was synthesized according to Synthetic Scheme 4.

[0120]

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3.19 g (10 mmol) of 4a and
90 g (10 mmol) of 4b was dissolved in 40 ml of tetrahydrofuran, and at room temperature, dicyclohexylcarbodiimide, 2.06 g (10 mmol) was added.
The reaction is carried out at 40 ° C. for 8 hours. After completion of the reaction, the insolubles were filtered off, the filtrate was concentrated, and ethyl acetate and water were added for extraction.
The solvent is collected under reduced pressure. Thereafter, the obtained residue was recrystallized from isopropyl alcohol to obtain 4.83 g (yield: 70%) of the objective exemplified coupler (4) -2. The structure was confirmed by ¹ H-NMR, IR and Mass spectra.

(5) Synthesis of Illustrative Coupler (5) -7 Illustrative coupler (5) -7 was synthesized according to Synthetic Scheme 5.

[0123]

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To 6.21 g (10 mmol) of 5a, 20 ml of toluene and 3.58 g (30 mmol) of thionyl chloride were added and reacted at about 90 ° C. for 4 hours. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 5b.

To 5b obtained above, 40 ml of tetrahydrofuran was added, and 1.62 g (10 mmol) of 5c and 2.37 g (30 mmol) of pyridine were further added. The mixture was added at room temperature for 2 hours and then at 50 ° C. Incubate for 1 hour. After completion of the reaction, 4 ml of 28% aqueous ammonia is further added, and the mixture is reacted at about 50 ° C. for 4 hours.

After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was acidified by adding ethyl acetate and dilute hydrochloric acid, and the organic layer was extracted and washed three times with water. Thereafter, the solvent was recovered under reduced pressure, and the obtained residue was recrystallized from acetonitrile to obtain 4.45 g of the objective exemplified coupler (5) -7 (yield: 5).
8%). The structure was confirmed by 1H-NMR, IR and Mass spectra.

(6) Synthesis of Illustrative Coupler (6) -15 Illustrative coupler (6) -15 was synthesized according to Synthetic Scheme 6.

[0128]

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3.92 g (10 mmol) of 6a and 4.
43 g (10 mmol) of 6b was dissolved in 40 ml of tetrahydrofuran, and at room temperature, dicyclohexylcarbodiimide, 2.06 g (10 mmol) was added.
The reaction is carried out at 40 ° C. for 8 hours. After completion of the reaction, the insolubles were filtered off, the filtrate was concentrated, and ethyl acetate and water were added for extraction.
The solvent is collected under reduced pressure. Thereafter, the obtained residue is recrystallized from ethanol to obtain 4.34 g (yield: 52%) of the objective exemplified coupler (6) -15. The structure was confirmed by ¹ H-NMR, IR and Mass spectra.

Other couplers of the coupler of the present invention can be synthesized according to the above. The coupler of the present invention can be used in an amount of usually 1 × 10 ^-3 mol to 1 mol, preferably 1 × 10 ^-2 mol to 8 × 10 ^-1 mol, per mol of silver halide. Further, the coupler of the present invention can be used in combination with another type of cyan coupler. In the coupler of the present invention,
The methods and techniques used for conventional dye-forming couplers apply analogously. The coupler of the present invention is used for a color photographic light-sensitive material such as a negative film, a positive film and a color photographic paper.

The light-sensitive material using the coupler of the present invention such as the color photographic paper may be of a single color or a multicolor. In a multicolor light-sensitive material, the coupler of the present invention is usually contained in a red-sensitive silver halide emulsion layer. The multicolor light-sensitive material has a dye image-forming constituent unit having photosensitivity in each of 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.

A typical multicolor light-sensitive material is a cyan dye image-forming structural unit comprising a red-sensitive silver halide emulsion layer containing a cyan coupler (at least one of the cyan couplers is a coupler of the present invention), A magenta dye image forming structural unit composed of a green light-sensitive silver halide emulsion layer containing a magenta coupler and a yellow dye image forming structural unit composed of a blue light-sensitive silver halide emulsion layer containing a yellow coupler are supported on a support. Consisting of The light-sensitive material can have additional layers such as a filter layer, an intermediate layer, a protective layer, an undercoat layer or an undercoat layer.

For incorporating the coupler of the present invention into an emulsion, a conventionally known method may be used. For example, the boiling point of tricresyl phosphate, dibutyl phthalate, etc. is 175 ° C.
After dissolving the coupler of the present invention alone or in combination with each of the above high-boiling organic solvents or low-boiling solvents such as butyl acetate and butyl propionate alone or as necessary, a surfactant is added. After mixing with an aqueous solution containing gelatin and then emulsifying with a high-speed rotary mixer or a colloid mill, etc., the mixture is added to a silver halide emulsion to prepare a silver halide emulsion containing the coupler of the present invention used in the present invention. it can.

The silver halide composition preferably used for the light-sensitive material using the coupler of the present invention includes silver chloride, 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 contains at least 1 mol% of silver chloride. 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.

The silver halide emulsion is used in the photographic industry to prevent fogging during the production, storage, or photographic processing of a light-sensitive material, and / or to maintain stable photographic performance. Compounds known as can be added.

Various additives can be used in a silver halide color photographic light-sensitive material using the coupler of the present invention.
For example, Research Disclosure (Research
hDisclosure) 176, 22-31 (19
As described in "December 1978", various additives such as a color fogging inhibitor, a dye image stabilizer, an ultraviolet ray inhibitor, an antistatic agent, a matting agent, and a surfactant which are usually used for photosensitive materials are used. be able to.

The silver halide color photographic material using the coupler of the present invention can form an image by performing a color development process known in the art. After color development, bleaching and fixing are performed. The bleaching process may be performed simultaneously with the fixing process. After the fixing process, a water 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.

The silver halide color photographic light-sensitive material using the coupler of the present invention contains a color developing agent as a color developing agent itself or as a precursor thereof in a hydrophilic colloid layer, and is processed by an alkaline activating bath. You can also.

[0139]

Next, the present invention will be described in detail with reference to examples, but the embodiments of the present invention are not limited to these examples.

Example 1 On a paper support laminated on both sides with polyethylene, the following layers were sequentially applied from the support side to prepare a red-sensitive color photographic material sample 1. The amount of the compound added is shown per 1 m ² unless otherwise specified (silver halide is a silver equivalent value).

First layer: emulsion layer 1.3 g of gelatin, red-sensitive silver chlorobromide emulsion (silver chloride 99.
A red-sensitive emulsion layer comprising 9.1 × 10 ^-4 mol of the comparative coupler a dissolved in 0.21 mol of dioctyl phthalate and 0.25 mol of dioctyl phthalate.

[0142]

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Second layer: protective layer A protective layer containing 0.50 g of gelatin. In addition, sodium salt of 2,4-dichloro-6-hydroxy-s-triazine was added as a hardening agent in an amount of 0.017 g per 1 g of gelatin.

Next, Comparative Coupler a of Comparative Sample 1 is shown in Table 1 (addition amount is 5% of Comparative Coupler a).
0 mol%), and a red-sensitive silver chlorobromide emulsion was used in Sample 1.
Comparative Samples 2 to 6 and Samples 7 to 18 of the present invention were prepared in exactly the same manner as Sample 1 except that the amount was changed to 80 mol%.

Each of the samples 1 to 18 obtained above was exposed to wedges in accordance with a conventional method, and then subjected to a developing process in the following developing process.

(Development Processing Step) 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 ° C. for 60 seconds The composition of the processing solution used in each processing step is as follows.

(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 27 g Water is added to make a total volume of 1 liter, and the pH is adjusted to 10.10.

(Bleaching and 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'-diaminostilbene sulfonic 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.

For the samples 1 to 18 processed above,
The maximum concentration (Dmax) was measured using a densitometer (KD-7, manufactured by Konica Corporation), and the treated samples were irradiated with a Xe fade meter (90,000 lux) and allowed to stand for 24 hours. The yellow stain concentration was measured.

[0151]

[Table 1]

[0152]

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[0153]

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As is clear from Table 1, the sample using the coupler of the present invention was used in an amount of 50 mol% of the coupler and 80 mol% of the silver halide as compared with the sample 1 using the comparative coupler a. It shows that Dmax is equal to or more than that, and that the initial yellow stain under light irradiation is equally excellent.

Further, a sample using the coupler of the present invention is:
It shows an excellent Dmax as compared with Samples 2 to 6 using Comparative Couplers b to f, and has an excellent initial yellow stain under light irradiation as compared with Samples 3 to 6 using Comparative Couplers c to f. You can see that there is.

Example 2 On a paper support, polyethylene was laminated on one side and polyethylene containing 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 Sample 19 of a multilayer silver halide color photographic light-sensitive material. The coating solution was prepared as follows.

Coating solution for the first layer 26.7 g of yellow coupler (Y-1), 10.0 g of dye image stabilizer (ST-1), dye image stabilizer (ST-1)
-2) To 6.67 g, 0.67 g of additive (HQ-1), antiirradiation dye (AI-3), and 6.67 g of high-boiling organic solvent (DNP), add and dissolve 60 ml of ethyl acetate. Using an ultrasonic homogenizer, the mixture was emulsified and dispersed in 220 ml of a 10% aqueous gelatin solution containing 7 ml of 20% surfactant (SU-1) 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.

[0159]

[Table 2]

[0160]

[Table 3]

[0161]

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[0162]

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[0163]

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[0164]

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[0165]

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[0166]

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[0167]

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(Method for Preparing Blue-Sensitive Silver Halide Emulsion) 4
The following (solution A) and (solution B) were pAg = 6.5 and pH = 3 in 1000 ml of a 2% gelatin aqueous solution kept at 0 ° C.
The solution was added simultaneously over 30 minutes while controlling to 0, and the following (Solution C) and (Solution D) were further pAg = 7.3 and pH = 5.
5 and simultaneously added over 180 minutes. The pH was controlled using an aqueous solution of sulfuric acid or sodium hydroxide. For control of pAg, a control liquid having the following composition was used. The composition of the control liquid is a mixed halide salt aqueous solution composed of sodium chloride and potassium sulfide. The ratio of chloride ion to bromide ion is 99.8: 0.2. When mixing the liquids, the molar ratio was 0.1 mol / l, and when mixing the liquids C and D, the molar ratio was 1 mol / l.

(Solution A) Sodium chloride 3.42 g Potassium bromide 0.03 g Water was added to 200 ml (Solution B) Silver nitrate 10 g Water was added to make 200 ml.

(Solution C) Sodium chloride 102.7 g Potassium bromide 1.0 g Water was added to 600 ml (Solution D) 300 g of silver nitrate was added and water was added to 600 ml After completion of the addition, 5% aqueous solution of Demol N manufactured by Kao Atlas Co., Ltd. and sulfuric acid After desalting with a 2.0% aqueous solution of magnesium, the mixture was mixed with an aqueous solution of gelatin to give an average particle size of 0.85
Thus, a monodispersed cubic emulsion EMP-1 having a size of μm, a coefficient of variation 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 compounds 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 method of green-sensitive silver halide emulsion) (solution A) and (B
Liquid) and the addition time of (Liquid C) and (Liquid D) were changed in the same manner as in EMP-1, except that the average particle diameter was 0.43 μm, the coefficient of variation was 0.08, and the silver chloride content was 99. .
A 5 mol% monodisperse cubic emulsion EMP-2 was obtained.

The EMP-2 was chemically ripened at 55 ° C. for 120 minutes using the following compounds 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 (Method for Preparing Red-Sensitive Silver Halide Emulsion) (Solution A) and (B)
Solution E), the average particle size was 0.50 μm, the coefficient of variation was 0.08, and the silver chloride content was 99 in the same manner as in EMP-1 except that the addition time of Solution C and the addition times of Solution C and Solution D were changed. .
A 5 mol% monodispersed cubic emulsion EMP-3 was obtained.

This EMP-3 was chemically ripened at 60 ° C. for 90 minutes using the following compounds 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

[0177]

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Next, in Sample 19 (comparative sample), the cyan couplers C-1 (comparative coupler a) and C-
2 (comparative coupler) is a coupler shown in Table 4 (addition amount is 50 mol% of the total number of moles of comparative couplers C-1 and C-2).
Amount), and the amount of the red-sensitive silver chlorobromide emulsion was changed to 80 mol%, and the samples 20, 20
1 (comparative sample) and samples 22 to 31 (sample of the present invention).

The obtained sample was exposed to wedges in the same manner as in Example 1 and then developed to obtain the maximum density (Dma) of the red-sensitive layer.
x) was measured.

The samples 19 to 31 were evaluated for color reproducibility and black background by the following methods.

First, a color checker manufactured by Macbeth was photographed using a color negative film (Konica Color Centuria 400: manufactured by Konica Corporation) and a camera (Konica FT-1 MOTOR: manufactured by Konica Corporation). continue,
Color negative development (CNK-4: manufactured by Konica Corporation)
And use the resulting negative image as a Konica Color Printer C
After exposing the samples 19 to 31 to a size of 82 mm × 117 mm using LP-P2000 (manufactured by Konica Corporation),
Development processing was performed in the same manner as in Example 1 to obtain a practical print. The printer conditions at the time of printing (exposure) were set for each sample so that the gray on the color checker became gray on the print.

The obtained practical prints were visually evaluated for color reproducibility and black background in the following five grades.

Color Reproducibility 1: 0 to 5 humans out of 20 judged good color reproducibility 2: 6 to 9 humans out of 20 judged good color reproducibility 3: When 10 to 13 humans out of 20 determined that color reproducibility was good. 4: When 20 to 14 humans determined that color reproducibility was good. When 18 to 20 people determine that the color reproducibility is good. Black background 1: When 0 to 5 people determine that the black background is good, out of 20 people 2: 6 to 9 out of 20 people When humans determine that the black background is good 3: Out of 20 people, 10 to 13 humans determine that the black background is good 4: Out of 20, 20 to 17 humans determine that the black background is good In the case of 5:20 out of 18 persons, 18 to 20 persons judged that the black background was good. The results are shown in Table 4.

[0184]

[Table 4]

As is clear from Table 4, comparative coupler C
Sample 19 (comparative sample) using -1 (same as Comparative Coupler a) and C-2 (Comparative Coupler) is extremely insufficient in color reproducibility. Further, the comparative couplers c and e were used at 50 mol% of the total number of moles of the comparative couplers C-1 and C-2.
In Samples 20 and 21 (comparative samples) using silver halide in an amount of 80 mol%, the color reproducibility of blue was significantly improved, but the color reproducibility of cyan and green was not significantly improved. The black density is not sufficient because the maximum density is low.

On the other hand, Samples 22 to 31 of the present invention containing the cyan coupler of the present invention (the amount of coupler used was 50 mol% of the total number of moles of comparative couplers C-1 and C-2).
And the amount of silver halide used is 80 mol%), the color reproducibility is good and the black background is excellent. Especially sample 2
Nos. 2, 23, 26, and 27 have good color reproducibility for all of cyan, blue, and green, and have good color development, high maximum density, and excellent black background.

[0187]

According to the present invention, a clear (color reproducibility) excellent in so-called spectral absorption characteristics, which is excellent in color developability, provides a sufficient color density, has sharp sharp absorption, and has little absorption in blue and green regions. Silver halide color photographic light-sensitive material which gives a cyan image. Further, it is possible to provide a silver halide color photographic light-sensitive material capable of forming a cyan image which does not generate light stability, particularly, no initial yellow stain.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Chen ▲ ヅ ▼ Style 1 Sakuracho, Hino-shi, Tokyo Konica Stock Company In-house F-term (reference) 2H016 BE03 BF06 BG02

Claims (6)

[Claims] 1. A silver halide color photographic light-sensitive material comprising a coupler represented by the following general formula (1). Embedded image (Wherein, R ₁ represents an acylamino group, a sulfonamide group, a ureido group, a sulfonyl group, a carbamoyl group, a sulfamoyl group, an imide group, an oxycarbonylamino group or an oxycarbonyl group, and R ₂ represents an alkyl group, an aryl group, A ring group, n1 represents an integer from 1 to 4, and when n1 is 2 or more, R ₁ may be the same or different, and X ₁ is a halogen atom, an alkyloxy group, an aryloxy group Or a heterocyclic oxy group.) 2. A silver halide color photographic light-sensitive material comprising a coupler represented by the following general formula (2). Embedded image (Wherein R ₃ and R ₄ represent a substituent, and n2 is 0 to 4)
It represents an integer of, when n2 is 2 or more, R ₃ may be different even in the same. X ₂ represents a halogen atom, an alkyloxy group, an aryloxy group or a heterocyclic oxy group. ) 3. A silver halide color photographic light-sensitive material comprising a coupler represented by the following general formula (3). Embedded image (Wherein, R ₅ represents an alkyl group, an aryl group or a heterocyclic group, R ₆ represents a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, and R ₇ represents an alkyl group, an aryl group or a heterocyclic group. X ₃ represents a halogen atom, an alkyloxy group, an aryloxy group or a heterocyclic oxy group.) 4. A silver halide color photographic light-sensitive material comprising a coupler represented by the following general formula (4). Embedded image (Wherein, R ₈ represents an alkyl group, an aryl group or a heterocyclic group, J represents an alkylene group, R ₉ represents a substituent, and X ₄ represents a halogen atom, an alkyloxy group, an aryloxy group or a heterocyclic group. Represents an oxy group.) 5. A silver halide color photographic material comprising a coupler represented by the following general formula (5). Embedded image (Wherein, Y ₁ represents a halogen atom, R ₁₀ represents a hydrogen atom or a substituent, n3 represents an integer of 2 to 5,
When 5-n3 is 2 or more, R ₁₀ may be the same or different. R ₁₁ has a Hammett's substituent constant σp value of −
Represents a substituent of 0.3 or more and 1.0 or less, and m1 is 0 to 5
And when m1 is 2 or more, R ₁₁ may be the same or different. X ₅ represents a halogen atom, an alkyloxy group, an aryloxy group or a heterocyclic oxy group. ) 6. A silver halide color photographic light-sensitive material comprising a coupler represented by the following general formula (6). Embedded image (Wherein, Y ₂ represents a halogen atom, R ₁₂ represents a hydrogen atom or a substituent, n4 represents an integer of 2 to 5,
When 5-n4 is 2 or more, R ₁₂ may be the same or different. R ₁₃ has a Hammett's substituent constant σp value of −
Represents a substituent of 0.3 or more and 1.0 or less, and m2 is 0 to 5
And when m2 is 2 or more, R ₁₃ may be the same or different. X ₆ represents a halogen atom, an alkyloxy group, an aryloxy group or a heterocyclic oxy group. )