IP Library Granted Patent US 7,291,449
Granted Patent B2
US 7,291,449 · App. 09/931,309 · Granted Nov 6, 2007

Silver halide photographic material and methine dye

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Quick Facts
Patent No.
US 7,291,449
App. No.
09/931,309
Granted
Nov 6, 2007
Kind
B2
Abstract

Disclosed is a silver halide photographic material which comprises at least one methine dye represented by the following formula (I): wherein Y represents a furan ring or a pyrrole ring, and Y may further be condensed with other 5- or 6-membered carbocyclic ring or heterocyclic ring, or may have a substituent; the bond between two carbon atoms in which Y is condensed may be a single bond or a double bond; Z represents an atomic group necessary to form a 5- or 6-membered nitrogen-containing heterocyclic ring, and Z may further be condensed with other 5- or 6-membered carbocyclic ring or heterocyclic ring; R represents a substituted or unsubstituted alkyl group, aryl group, or heterocyclic group; D represents a group necessary to form a methine dye; L 1 and L 2 each represents a methine group; p represents 0 or 1; M represents a counter ion; and m represents a number of 0 or higher necessary to neutralize the charge in the molecule.

Claims (19)

1. A silver halide photographic material which comprises a silver halide emulsion containing silver halide grains that are sensitized with at least one sensitizing methine dye represented by the following formula (I):

wherein Y represents a furan ring, and Y may further be condensed with other 5- or 6-membered carbocyclic ring or heterocyclic ring, or may have a substituent; the bond between two carbon atoms in which Y is condensed may be a single bond or a double bond; Z represents an oxazole ring, a thiazole ring, an imidazole ring, a 2-pyridine ring or a 4-pyridine ring, and Z may further be condensed with other 5- or 6-membered carbocyclic ring or heterocyclic ring; R represents a substituted or unsubstituted alkyl group, aryl group, or heterocyclic group; D represents a group necessary to form a sensitizing methine dye; L 1 and L 2 each represents a methine group; p represents 0 or 1; M represents a counter ion; and m represents a number of 0 or higher necessary to neutralize the charge in the molecule.

2. The silver halide photographic material as claimed in claim 1 , wherein the methine dye represented by formula (I) is represented by the following formula (XX):

wherein Y 51 represents a furan ring which may be condensed with other 5- or 6-membered carbocyclic or heterocyclic ring or may have a substituent, and two carbon atoms to which Y 51 is condensed may be bonded by a single bond or a double bond; X 51 represents an oxygen atom, a sulfur atom, or a nitrogen atom and X 52 each represents an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom or a nitrogen atom; Y 52 represents an atomic group necessary to form a benzene ring or a 5- or 6-membered unsaturated heterocyclic ring, which may further be condensed with other 5- or 6-membered carbocyclic or heterocyclic ring or may have a substituent, and two carbon atoms to which Y 52 is condensed may be bonded by a single bond or a double bond; R 51 and R 52 each represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; L 51 , L 52 and L 53 each represents a methine group; n 51 represents 0, 1, 2, 3 or 4; M 51 represents a counter ion; and m 51 represents a number of 0 or higher necessary to neutralize the charge in the molecule.

3. A silver halide photographic material which comprises a silver halide emulsion containing silver halide grains that are sensitized with at least one sensitizing methine dye represented by the following formula (I):

wherein Y represents an atomic group necessary to form a 5- or 6-membered unsaturated heterocyclic ring, and Y may further be condensed with other 5- or 6-membered carbocyclic ring or heterocyclic ring, or may have a substituent; the bond between two carbon atoms in which Y is condensed may be a single bond or a double bond; Z represents an atomic group necessary to form a 5- or 6-membered nitrogen-containing heterocyclic ring, and Z may further be condensed with other 5- or 6-membered carbocyclic ring or heterocyclic ring; R represents a substituted or unsubstituted alkyl group, aryl group, or heterocyclic group; D represents a group necessary to form a sensitizing methine dye; L 1 and L 2 each represents a methine group; p represents 0 or 1; M represents a counter ion; and m represents a number of 0 or higher necessary to neutralize the charge in the molecule; wherein the condensed ring containing Y and Z in the sensitizing methine dye represented by formula (I) is selected from the following Y-1 to Y-26, provided that Y-1 to Y-3 and Y-6 to Y-26 may further be condensed with other 5- or 6-membered carbocylic or heterocyclic ring, or may have a substituent:

in each structural formula, * represents a position to link to a methine chain.

4. A silver halide photographic material which comprises at least one methine dye represented by the following formula (XXXI) or (XXXII):

wherein L 61 , L 62 and L 63 each represents a methine group; V61 represents a halogen atom; X 61 represents an oxygen atom, a sulfur atom, or a nitrogen atom; X 62 represents an oxygen atom, a sulfur atom, a selenium atom, a nitrogen atom, or a carbon atom; Y 62 represents an atomic group necessary to form a benzene ring or a 5- or 6-membered unsaturated heterocyclic ring, which may be condensed with other 5- or 6-membered carbocyclic or heterocyclic ring or may have a substituent, and two carbon atoms to which Y 62 is condensed may be bonded by a single bond or a double bond; R 61 and R 62 each represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; n 61 represents 0 or 1; M 61 represents a counter ion; and m 61 represents a number of 0 or higher necessary to neutralize the charge in the molecule.

5. The silver halide photographic material as claimed in claim 4 , wherein the methine dye represented by formula (XXXI) or (XXXII) is represented by the following formula (XXXIa) or (XXXIIa):

wherein V 85 represents a halogen atom; X 81 and X 82 each represents an oxygen atom or a sulfur atom; R 81 and R 82 each represents an alkyl group substituted with an acid radical; V 81 , V 82 , V 83 and V 84 each represents a hydrogen atom or a substituent; M 81 represents a counter ion; and m 81 represents a number of 0 or higher necessary to neutralize the charge in the molecule.

6. The silver halide photographic material as claimed in claim 5 , wherein in the methine dye represented by formula (XXXIa) or (XXXIIa), at least either R 81 or R 82 represents an alkyl group substituted with a carboxyl group or an alkanesulfonylcarbamoyl group, and the other represents an alkyl group substituted with a sulfo group.

7. The silver halide photographic material as claimed in claim 4 , wherein the methine dye represented by formula (XXXI) or (XXXII) is represented by the following formula (XXXIb) or (XXXIIb):

wherein V 95 represents a halogen atom; X 91 and X 92 each represents an oxygen atom or a sulfur atom; R 91 and R 92 each represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; A 91 represents a methyl group, an ethyl group or a propyl group; V 91 , V 92 , V 93 and V 94 each represents a hydrogen atom or a substituent; M 91 represents a counter ion; and m 91 represents a number of 0 or higher necessary to neutralize the charge in the molecule.

8. A silver halide photographic material which comprises at least one sensitizing methine dye represented by the following formula (I):

wherein Y represents a pyrrole ring, and Y may further be condensed with other 5- or 6-membered carbocyclic ring or heterocyclic ring, or may have a substituent; the bond between two carbon atoms in which Y is condensed may be a single bond or a double bond; Z represents an oxazole ring, a thiazole ring, an imidazole ring, a 2-pyridine ring or a 4-pyridine ring, and Z may further be condensed with other 5- or 6-membered carbocyclic ring or heterocyclic ring; R represents a substituted or unsubstituted alkyl group, aryl group, or heterocyclic group; D represents a group necessary to form a sensitizing methine dye; L 1 and L 2 each represents a methine group; p represents 0 or 1; M represents a counter ion; and m represents a number of 0 or higher necessary to neutralize the charge in the molecule.

9. The silver halide photographic material as claimed in claim 8 , wherein Z represents an oxazole ring, a thiazole ring, an imidazole ring, a 2-pyridine ring or a 4-pyridine ring.

10. The silver halide photographic material as claimed in claim 8 , wherein the methine dye represented by formula (I) is represented by the following formula (XX):

wherein Y 51 represents a pyrrole ring which may be condensed with other 5- or 6-membered carbocyclic or heterocyclic ring or may have a substituent, and two carbon atoms to which Y 51 is condensed may be bonded by a single bond or a double bond; X 51 and X 52 each represents an oxygen atom, a sulfur atom, or a nitrogen atom; Y 52 represents an atomic group necessary to form a benzene ring or a 5- or 6-membered unsaturated heterocyclic ring, which may further be condensed with other 5- or 6-membered carbocyclic or heterocyclic ring or may have a substituent, and two carbon atoms to which Y 52 is condensed may be bonded by a single bond or a double bond; R 51 and R 52 each represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; L 51 L 52 and L 53 each represents a methine group; n 51 represents 0, 1, 2, 3 or 4; M 51 represents a counter ion; and m 51 represents a number of 0 or higher necessary to neutralize the charge in the molecule.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 15, 2007
From: FUJIFILM HOLDINGS CORPORATION (FORMERLY FUJI PHOTO FILM CO., LTD.)
To: FUJIFILM CORPORATION
Reel/Frame 018904/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 17, 2001
From: NAKAMURA, TETSUO; HIOKI, TAKANORI; OHZEKI, KATSUHISA; HANAKI, NAOYUKI
To: FUJI PHOTO FILM CO., LTD.
Reel/Frame 012099/0857 →