Dye-forming coupler, silver halide photographic light-sensitive material, and method for producing an azomethine dye
View Patent ↗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.
1. A method for producing an azomethine dye, comprising reacting a dye forming coupler compound 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, with an oxidized product of a developing agent.
2. The method of claim 1 , wherein the compound represented by formula (I) is a compound represented by the following formula (IA):
wherein E A and Z A each independently represent an aryl group or a heterocyclic group.
3. The method of claim 2 , wherein 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.
4. The method of claim 2 , wherein E A is an aryl or heterocyclic group, having substituents on both of positions adjacent to the carbon atom bonded to the oxazolidinedione ring.
5. The method of claim 2 , wherein E A is a heterocyclic group.
6. The method of claim 5 , wherein the compound represented by formula (IA) is a compound represented by the following formula (II):
wherein 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.
7. The method of claim 6 , wherein, in the compound represented by formula (II), Q is represented by the following formula (III):
wherein 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.
8. The method of claim 7 , wherein L Q is a carbonyl group.
9. The method of claim 2 , wherein Z A is a heterocyclic group.
10. The method of claim 2 , wherein Z A is an aryl group having a substituent on an ortho position thereof.
11. The method of claim 2 , wherein the compound represented by formula (IA) is a compound represented by the following formula (IV):
wherein 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 ('s) may bond together to form a ring.
12. The method of claim 2 , wherein the compound represented by formula (IA) is a compound represented by the following formula (V):
wherein 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 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.
13. The method of claim 2 , wherein a p-phenylenediamine compound is reacted together with the compound represented by formula (IA).
14. The method of claim 1 , wherein the compound represented by formula (I) is a compound represented by the following formula (IB):
wherein W represents a nitrogen-containing heterocyclic group, Z B represents a substituted aryl group, and X and Y each independently represent ═O, ═S, or ═N—R, in which R represents a substituent.
15. The method of claim 14 , wherein 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.
16. The method of claim 14 , wherein 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.
17. The method of claim 14 , wherein a p-phenylenediamine compound is reacted together with the compound represented by formula (IB).
18. The method of claim 1 , wherein a p-phenylenediamine compound is reacted together with the compound represented by formula (I).
19. A dye-forming coupler represented by the following formula (IA):
wherein E A represents a heterocyclic group and Z A represents an aryl group or a heterocyclic group.
20. A dye-forming coupler represented by the following formula (IB):
wherein W represents a nitrogen-containing heterocyclic group, Z B represents a substituted aryl group, and X and Y each independently represent ═O, ═S, or ═N—R, in which R represents a substituent.