Methine dyes, manufacturing methods thereof, and silver halide photographic materials containing same dyes
View Patent ↗Methine dye compounds represented by formula (1) and highly sensitive silver halide photographic materials containing these compounds: Dye1-(L 1 -(Dye2) m1 ) m2 (CI 1 ) y1 (1) wherein L 1 represents a linkage group represented by formula (2), m1 represents an integer of 1 to 5, m2 represents an integer of 1 to 5, Dye1 represents a first chromophore, Dye 2 represents a second chromophore, CI 1 represents an ion for neutralization of electric charge, and y1 represents a number of the ions required for neutralization of electric charges; -G 1 -A 1 -Y 1 -G 2 -Y 2 -A 2 -G 3 - (2) wherein A 1 and A 2 each individually represent a carbonyl group or a sulfonyl group, Y 1 and Y 2 each individually represent —O—, —S— or —NR 1 —, R 1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or a heterocyclic group, and G 1 , G 2 and G 3 each individually represent a divalent linkage group.
1. A compound represented by formula (1):
Dye1-(L 1 -(Dye2) m1 ) m2 (CI 1 ) y1 (1)
wherein L 1 represents a linkage group represented by formula (2), m1 represents an integer of 1 to 5, m2 represents an integer of 1 to 5, Dye1 represents a first chromophore, Dye 2 represents a second chromophore, CI 1 represents an ion for neutralization of electric charge, and y1 represents a number of the ions required for neutralization of electric charges;
-G 1 -A 1 -Y 1 -G 2 -Y 2 -A 2 -G 3 - (2)
wherein A 1 and A 2 each individually represent a carbonyl group or a sulfonyl group, Y 1 and Y 2 each individually represent —O—, —S— or —NR 1 —, R 1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or a heterocyclic group, and G 1 , G 2 and G 3 each individually represent a divalent linkage group, and
wherein both Dye1 and Dye2 are cyanine or merocyanine chromophores which each have at least one benzoxazole nucleus.
2. A method of manufacturing a compound of formula (1) as defined in claim 1 by causing a reaction between a compound represented by formula (3) and a compound represented by formula (4):
Dye3-G 4 -A 3 -Y 4 -G 5 -Y 4 -H (CI 2 ) y2 (3)
wherein Dye 3 represents a chromophore, Y 4 represents —NH—, —NH 2 + —, —S— or —O—, A 3 represents a carbonyl group or a sulfonyl group, Y 3 represents —O—, —S— or —NR 1 —, R 1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or a heterocyclic group, G 4 and G 5 each individually represent a divalent linkage group, CI 2 represents an ion for neutralization of electric charge, and y2 represents a number of the ions required for neutralization of electric charges
Dye4-G 6 -A 4 -Y 5 (CI 3 ) y3 (4)
wherein Dye4 represents a chromophore, A 4 represents a carbonyl group or a sulfonyl group, G 6 represents a divalent linkage group, Y 5 represents a hydroxyl group, a halogen atom, an alkoxy group, an aryloxy group, an acyloxy group, an alkyl- or arylsulfonyloxy group, an alkyl- or aryloxycarbonyloxy group, an imidyloxycarbonyloxy group or a heterocyclic group, CI 3 represents an ion for neutralization of electric charge, and y3 represents a number of the ions required for neutralization of electric charges.
3. The compound as claimed in claim 1 , wherein both Dye1 and Dye2 are cyanine chromophores.
4. The compound as claimed in claim 1 , wherein Dye1 is a cyanine chromophore and Dye2 is a merocyanine chromophore.