Dye-forming coupler, silver halide photographic light-sensitive material, and method for producing an azomethine dye

Abstract

A dye-forming coupler of the formula (I). A silver halide photographic light-sensitive material that contains at least one dye-forming coupler of the formula (I). A method for producing an azomethine dye, which method comprises using a compound of the formula (I): wherein E is an aryl, heterocyclic, or —C(═O)W group, in which W is a nitrogen-containing heterocyclic group, Z is an aryl or heterocyclic group, and X and Y each independently are ═O, ═S or ═N—R, in which R is a substituent, with the proviso that when E is an aryl or heterocyclic group, X and Y each are ═O, and that when E is a —C(═O)W group, Z is a substituted aryl group.

What we claim is:  
     
         1 . A dye-forming coupler represented by the following formula (I):  
       
         
           
           
               
               
           
         
         wherein E represents an aryl group or heterocyclic group, or a —C(═O)W group, in which W represents a nitrogen-containing heterocyclic group, Z represents an aryl group or a heterocyclic group, and X and Y each independently represent ═O, ═S, or ═N—R, in which R represents a substituent, with the proviso that when E represents an aryl group or a heterocyclic group, X and Y each represent ═O, and that when E represents a —C(═O)W group, Z represents a substituted aryl group.  
       
     
     
         2 . The dye-forming coupler as claimed in  claim 1 , wherein the dye-forming coupler represented by formula (I) is represented by the following formula (IA):  
       
         
           
           
               
               
           
         
         wherein, in formula (IA), E A  and Z A  each independently represent an aryl group or a heterocyclic group.  
       
     
     
         3 . The dye-forming coupler as claimed in  claim 1 , wherein the dye-forming coupler represented by formula (I) is represented by the following formula (IB):  
       
         
           
           
               
               
           
         
         wherein, in formula (IB), W represents a nitrogen-containing heterocyclic group, ZB represents a substituted aryl group, and X and Y each independently represent ═O, ═S, or ═N—R, in which R represents a substituent.  
       
     
     
         4 . A silver halide photographic light-sensitive material, containing at least one dye-forming coupler represented by the following formula (I):  
       
         
           
           
               
               
           
         
         wherein E represents an aryl group or heterocyclic group, or a —C(═O)W group, in which W represents a nitrogen-containing heterocyclic group, Z represents an aryl group or a heterocyclic group, and X and Y each independently represent ═O, ═S, or ═N—R, in which R represents a substituent, with the proviso that when E represents an aryl group or a heterocyclic group, X and Y each represent ═O, and that when E represents a —C(═O)W group, z represents a substituted aryl group.  
       
     
     
         5 . The silver halide photographic light-sensitive material as claimed in  claim 4 , wherein the dye-forming coupler represented by formula (I) is represented by the following formula (IA):  
       
         
           
           
               
               
           
         
         wherein, in formula (IA), E A  and Z A  each independently represent an aryl group or a heterocyclic group.  
       
     
     
         6 . The silver halide photographic light-sensitive material as claimed in  claim 5 , wherein, in the dye-forming coupler represented by formula (IA), E A  is an aryl or heterocyclic group, having a substituent on at least one position adjacent to the carbon atom bonded to the oxazolidinedione ring.  
     
     
         7 . The silver halide photographic light-sensitive material as claimed in  claim 5 , wherein, in the dye-forming coupler represented by formula (IA), E A  is an aryl or heterocyclic group, having substituents on both of positions adjacent to the carbon atom bonded to the oxazolidinedione ring.  
     
     
         8 . The silver halide photographic light-sensitive material as claimed in  claim 5 , wherein, in the dye-forming coupler represented by formula (IA), E A  is a heterocyclic group.  
     
     
         9 . The silver halide photographic light-sensitive material as claimed in  claim 8 , wherein the dye-forming coupler represented by formula (IA) is represented by the following formula (II):  
       
         
           
           
               
               
           
         
         wherein, in formula (II), Z A  represents an aryl group or a heterocyclic group, Q represents a group of atoms composed of carbon atoms and/or hetero atoms necessary to form, together with the N—C═N, a 5-, 6- or 7-membered ring, and R 1  represents a substituent.  
       
     
     
         10 . The silver halide photographic light-sensitive material as claimed in  claim 9 , wherein, in the dye-forming coupler represented by formula (II), Q is represented by the following formula (III):  
       
         
           
           
               
               
           
         
         wherein, in formula (III), L Q  represents a carbonyl or sulfonyl group, and R 2  and R 3 , which are the same or different, each represent a hydrogen atom or a substituent, or R 2  and R 3  may bond together to form a ring.  
       
     
     
         11 . The silver halide photographic light-sensitive material as claimed in  claim 10 , wherein when Q in the dye-forming coupler represented by formula (II) is represented by the formula (III), said L Q  is a carbonyl group.  
     
     
         12 . The silver halide photographic light-sensitive material as claimed in  claim 5 , wherein, in the dye-forming coupler represented by formula (IA), Z A  is a heterocyclic group.  
     
     
         13 . The silver halide photographic light-sensitive material as claimed in  claim 5 , wherein, in the dye-forming coupler represented by formula (IA), Z A  is an aryl group having a substituent on an ortho position thereof.  
     
     
         14 . The silver halide photographic light-sensitive material as claimed in  claim 5 , wherein the dye-forming coupler represented by formula (IA) is represented by the following formula (IV):  
       
         
           
           
               
               
           
         
         wherein, in formula (IV), E A  represents an aryl group or a heterocyclic group; R 4  represents a halogen atom, an alkoxy group, or an aryloxy group; R 5  represents a substituent; and n is an integer of 0, or 1 to 4; when n is an integer of 2 to 4, R 5 's each are the same or different; or the groups adjacent to each other among R 4  and R 5 (Is) may bond together to form a ring.  
       
     
     
         15 . The silver halide photographic light-sensitive material as claimed in  claim 5 , wherein the dye-forming coupler represented by formula (IA) is represented by the following formula (V):  
       
         
           
           
               
               
           
         
         wherein, in formula (V), Q is a group represented by the following formula (III), R 1  represents a substituent, R 4  represents a halogen atom, an alkoxy group, or an aryloxy group, R 5  represents a substituent, n is an integer of 0 or 1 to 4; when n is an integer of 2 to 4, R 5 's each may be the same or different, or the groups adjacent to each other among R 4  and R 5 ('s) may bond together to form a ring:  
         
           
             
             
                 
                 
             
           
         
         wherein, in formula (III), L Q  represents a carbonyl or sulfonyl group, R 2  and R 3 , which are the same or different, each represent a hydrogen atom or a substituent, or R 2  and R 3  may bond together to form a ring.  
       
     
     
         16 . The silver halide color photographic light-sensitive material as claimed in  claim 4 , wherein the dye-forming coupler represented by formula (I) is represented by the following formula (IB):  
       
         
           
           
               
               
           
         
         wherein, in formula (IB), W represents a nitrogen-containing heterocyclic group, ZB represents a substituted aryl group, and X and Y each independently represent ═O, ═S, or ═N—R, in which R represents a substituent.  
       
     
     
         17 . The silver halide color photographic light-sensitive material as claimed in  claim 16 , wherein, in the formula (IB), Z B  is a phenyl group substituted by a halogen atom or an alkoxy group on the 2-position thereof, and having a substituent on the 5-position thereof.  
     
     
         18 . The silver halide color photographic light-sensitive material as claimed in  claim 16 , wherein, in the formula (IB), Z B  is a phenyl group substituted by a halogen atom or an alkoxy group on the 2-position thereof, and having a substituent on the 5-position thereof; and X and Y each represent ═O.  
     
     
         19 . A method for producing an azomethine dye, comprising using a compound represented by the following formula (IA):  
       
         
           
           
               
               
           
         
         wherein E A  and Z A  each independently represent an aryl group or a heterocyclic group.  
       
     
     
         20 . The method as claimed in  claim 19 , wherein a p-phenylenediamine compound is used together with the compound represented by formula (IA).