US 8,507,689 B2 · Organic salt compound, and optical recording material and optical recording medium using the organic salt compound

Abstract

Compounds of the class of organic salts based on monomethine cyanine cation and azomethine complex cation are useful to promote light sensitivity and light resistance in laser writable and readable recording material. The compounds of Formula (I) and (IV) are exemplified in Formula (I) with X being oxygen, sulfur, or selenium; R1 and R2 are each C1-C20 alkyl, C7-C30 arylalkyl; R3 to R6 are each hydrogen, C1-C20 alkyl, etc.; R4 and R5 may be taken together to form a 6-membered ring; Y1 and Y2 are each C1-C20 alkyl; R7 to R10 are each hydrogen, C1-C20 alkyl, etc.; and adjacent two of R7 to R10 may be taken together to form a 5- or 6-membered ring. In Formula (IV) M′ is Fe, Co, Ni, Cr or Mn; and R11 to R26 are each hydrogen, nitro, —NRR′ (R and R′ are each C1-C4 alkyl).

An organic salt compound consisting of a monomethine cyanine cation represented by formula (I) and an azomethine complex anion represented by formula (IV):

wherein X represents an oxygen atom, sulfur atom, a selenium atom, or —NY3—;
R4 and R2 each independently represent a group represented by formula (II) shown below, a group represented by formula (II') shown below, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, and R1 and R2 may be taken together to form a 3- to 6-membered alicyclic group;
R3, R4, R5, and R6 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, and R4 and R5 may be taken together to form a 6-membered ring;
Y1, Y2, and Y3 each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, or a group represented by formula (III) shown below;
R7, R8, R9, and R10 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a halogen atom, a nitro group, or a cyano group, and adjacent two of R7, R8, R9, and R10 may be taken together to form a 5- or 6-membered ring;
and
a methylene moiety of the alkyl groups and the arylalkyl groups may be interrupted by —O—, —S—, —CO—, —COO—, —OCO—, —SO2—, —NH—, —CONH—, —NHCO—, —N═CH—, or —CH═CH—;
wherein, in formula (II), the bond between G and T is a double bond, a conjugated double bond, or a triple bond;
G represents a carbon atom;
T represents a carbon atom, an oxygen atom, or a nitrogen atom;
w represents a number from 0 to 4;
x, y, and z each represent, 0 or 1, provided that, when T is oxygen, y=z=0, and, when T is nitrogen, y+z=0 or 1;
R01, R02, R03, and R04 each independently represent a hydrogen atom, a hydroxyl group, a nitro group, a cyano group, a halogen atom, or an optionally substituted alkyl group having 1 to 4 carbon atoms of which a methylene moiety may be interrupted by —O— or —CO—;
and R01 and R04 may be taken together to form a cycloalkene ring or a heterocyclic ring;
and
in formula (II′), the bond between G′ and T′ is a double bond or a conjugated double bond;
G′ represents a carbon atom;
T′ represents a carbon atom or a nitrogen atom;
w′ represents a number of 0 to 4;
R01′ represented a hydrogen atom, a hydroxyl group, a nitro group, a cyano group, a halogen atom, an optionally substituted alkyl group having 1 to 4 carbon atoms of which a methylene moiety may be interrupted by —O— or —CO—;
and the ring containing G′ and T′ is a 5-membered ring optionally containing a hetero atom, a 6-membered ring optionally containing a hetero atom, a quinoline ring, an isoquinoline ring, or an anthraquinone ring, each optionally substituted with a halogen atom, a hydroxyl group, a nitro group, a cyano group, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms;
wherein Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, and Ri each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms of which a methylene moiety may be interrupted by —O— or —CO—;
Q represents a direct bond or an optionally substituted alkylene group having 1 to 8 carbon atoms of which a methylene moiety may be interrupted by —O—, —S—, —CO—, —COO—, —OCO—, —SO2—, —NH—, —CONH—, —NHCO—, —N═CH—, or —CH═CH—;
and M represents Fe, Co, Ni, Ti, Cu, Zn, Zr, Cr, Mo, Os, Mn, Ru, Sn, Pd, Rh, Pt, or Ir;
wherein M′ represents Fe, Co, Ni, Cu, Cr, Mo, Os, Mn, Ru, Sn, Pd, Rh, Pt, Al, or Ir;
R11, R12, R13, R R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, and R26 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a nitro group, a cyano group, or —NRR';
R and R′ each represent an alkyl group having 1 to 4 carbon atoms;
and any adjacent two of R11 through R26 may be taken together to form a 5- or 6-membered ring.

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Organic salt compound, and optical recording material and optical recording medium using the organic salt compound

Life of this patent

Organic salt compound, and optical recording material and optical recording medium using the organic salt compound

Life of this patent

Abstract

Claims3