Dye-forming coupler, silver halide photographic light-sensitive material and azomethine dye compound

A dye-forming coupler represented by formula (II):

• 98
• wherein R1 represents a substituent;
• R2 represents a substituent;
• l represents an integer of 0 to 4;
• when l is 2 or more, R2s may be the same or different, or R2s may bond with each other to form a ring;
• R3 represents a substituent;
• R4 represents a substituent;
• m represents an integer of 0 to 4;
• when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring;
• and Y represents a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent;
• with the proviso that the following compound (I-A) is excluded from the dye-forming coupler represented by formula (II).
• 99

A dye-forming coupler represented by formula (1-2):

• 100
• wherein Q1represents a group represented by —C(—R11)═C(—R12)—Z—;
• Z represents —SO2— or —CO—;
• R11 and R12 bond with each other to form, together with the —C═C— moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent;
• R1 represents a substituent;
• R3 represents a substituent;
• R4 represents a substituent;
• m represents an integer of 0 to 4;
• when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring;
• and X1 represents a group that has thereon a dissociation group whose pKa is 1 to 12, and that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent.

A silver halide photographic light-sensitive material, which comprises at least one dye-forming coupler selected from the group consisting of a dye-forming coupler represented by formula (I), a dye-forming coupler represented by formula (II), and a dye-forming coupler represented by formula (I-2):

• 101
• wherein Q represents a group represented by —C(—R11)═C(—R12)—SO2—;
• R11 and R12 bond with each other to form, together with the —C═C— moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent;
• R1 represents a substituent;
• R3 represents a substituent;
• R4 represents a substituent;
• m represents an integer of 0 to 4;
• when m is 2 or more, R4s may be the same or different, or R4s may bond each other to form a ring;
• and X represents a hydrogen atom, or a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent;
• 102
• wherein R1 represents a substituent;
• R2 represents a substituent;
• 1 represents an integer of 0 to 4;
• when 1 is 2 or more, R2s may be the same or different, or R2s may bond with each other to form a ring;
• R3 represents a substituent;
• R4 represents a substituent;
• m represents an integer of 0 to 4;
• when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring;
• and Y represents a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent;
• 103
• wherein Q1represents a group represented by —C(—R11)═C(—R12)—Z—;
• Z represents —SO2— or —CO—;
• R11 and R12 bond with each other to form, together with the —C═C— moiety, a 5-to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent;
• R1 represents a substituent;
• R3 represents a substituent;
• R4 represents a substituent;
• m represents an integer of 0 to 4;
• when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring;
• and X1 represents a group that has thereon a dissociation group whose pKa is 1 to 12, and that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent;
• with the proviso that the following compound (I-A) is excluded from the dye-forming coupler represented by formula (I) or (II).
• 104

An azomethine dye compound represented by formula (D):

• 105
• wherein, in formula (D), Q represents a group represented by —C(—R11)═C(—R12)—SO2—;
• R11 and R12 bond with each other to form, together with the —C═C— moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent;
• R1 represents a substituent;
• R3 represents a substituent;
• R4 represents a substituent;
• m represents an integer of 0 to 4;
• when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring;
• R5 and R6 each independently represent a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring;
• R7 represents a substituent;
• n represents an integer of 0 to 4;
• when n is 2 or more, R7s may be the same or different, or R7s may bond with each other to form a fused ring;
• or when n is 1 or more, R7 may bond with R5 or R6 to form a fused ring;
• with the proviso that at least one group selected from the group consisting of R1, R3, R4, the substituent represented by R11, the substituent represented by R12, and at least one substituent on the ring that is formed by a combination of R11 and R12, is a group having 10 or more carbon atoms in total.

An azomethine dye compound represented by formula (IV), wherein an angle that is defined by a dihedral angle C*1 N*2 C*3 C*4 and that is the most stabilized stereochemical structure in terms of energy, which is measured by quantum chemistry calculations, is within the range between −28° and 28°:

• 106
• wherein, in formula (IV), *1, *2, *3 and *4 each express a number labeled on the atom and define the angle represented by the dihedral angle C*1 N*2 C*3 C*4;
• R3 and R4 each independently represent a substituent;
• m represents an integer of 0 to 4;
• when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring;
• R5 and R6 each independently represent a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring;
• R8 represents an aryl group or a heterocyclic group,
• with the proviso that at least one group selected from the group consisting of R3, R4, and at least one substituent on the aryl ring or heterocycle represented by R8, is a group having 10 or more carbon atoms in total;
• and that the calculation based on quantum chemistry, which is used to measure the dihedral angle C*1 N*2 C*3 C*4 is carried out using the basis function of 6-31 G* or more according to a widely used B3LYP method (density-functional method).

A silver halide photographic light-sensitive material comprising a coupler capable of forming a dye upon a coupling reaction with an oxidized product of an aromatic primary amine,

• wherein at least one of said dye formed by coupling reaction is one selected from the group consisting of an azomethine dye compound represented by formula (D) and an azomethine dye compound represented by formula (IV):
• 108
• wherein, in formula (D), Q represents a group represented by —C(—R11)═C(—R12)—SO2—;
• R11 and R12 bond with each other to form, together with the —C═C— moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent;
• R1 represents a substituent;
• R3 represents a substituent;
• R4 represents a substituent;
• m represents an integer of 0 to 4;
• when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring;
• R5 and R6 each independently represent a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring;
• R7 represents a substituent;
• n represents an integer of 0 to 4;
• when n is 2 or more, R7s may be the same or different, or R7s may bond with each other to form a fused ring;
• or when n is 1 or more, R7 may bond with R5 or R6 to form a fused ring;
• with the proviso that at least one group selected from the group consisting of R1, R3, R4, the substituent represented by R11, the substituent represented by R12, and at least one substituent on the ring that is formed by a combination of R11 and R12, is a group having 10 or more carbon atoms in total;
• and
• 109
• wherein, in formula-(IV), an angle that is defined by a dihedral angle C*1 N*2 C*3 C*4 and that is the most stabilized stereochemical structure in terms of energy, which is measured by quantum chemistry calculations, is within the range between −280 and 28°;
• and *1, *2, *3 and *4 each express a number labeled on the atom and define the angle represented by the dihedral angle C*1 N*2 C*3 C*4;
• R3 and R4 each independently represent a substituent;
• m represents an integer of 0 to 4;
• when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring;
• R5 and R6 each independently represent a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring;
• R8 represents an aryl group or a heterocyclic group, with the proviso that at least one group selected from the group consisting of R3, R4, and at least one substituent on the aryl ring or heterocycle represented by R8, is a group having 10 or more carbon atoms in total;
• and that the calculation based on quantum chemistry, which is used to measure the dihedral angle C*1 N*2 C*3 C*4 is carried out using the basis function of 6-31 G* or more according to a widely used B3LYP method (density-functional method).