US 2007/0184232 A1Published application

Optical recording materials having high storage density

OwnerRyuichi Takahashi, Kazuhiko Kunimoto +2inventors

InventorsRyuichi Takahashi, Kazuhiko Kunimoto, Peter Sutter, Urs Lehmann

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Abstract

The invention relates to an optical recording medium comprising a substrate, a reflecting layer and a recording layer comprising a compound of formula (I) or a tautomer thereof, wherein G1, G2 and G3 are each independently of the other A1, A2 and A3 are each independently of the other N(R14),O, S or Se and A4 is C(C1-C5aIkyl)2, C(C4-C5alkylene), N(R14), O, S, Se, N═C(R15) or CH═C(R16); M1 is an at least trivalent metal of groups 3 to 15 most preferred Co(III) or Cr(III); Q1, Q2 and Q3 are each independently of the other C(R17), N or P. Recording and playback are effected especially at a wavelength of from 350 to 500 nm, for example using a blue laser.

Claims19

Dependent claims

An optical recording medium comprising a substrate, a recording layer and optionally one or more reflecting layers, wherein the recording layer comprises a compound of formula

or a tautomer thereof, wherein
G1, G2 and G3 are each independently of the other
A1, A2 and A3 are each independently of the other N(R14), O, S or Se and A4 is C(C1-C5alkyl)2, C(C4-C5alkylene), N(R14), O, S, Se, N═C(R15) or CH═C(R16);
M1 is an at least trivalent metal of groups 3 to 15 [formerly groups IIIA to VB];
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 and R16 are each independently of the others hydrogen, R18, or C6-C12aryl, C4-C12heteroaryl, C7-C12aralkyl or C5-C12heteroaralkyl each unsubstituted or substituted by one or more, where applicable identical or different, radicals R18;
or
R1 and R2, R3 and R4, R5 and R6, R7 and R8, R7 and R15 and/or R7 and R16, together in pairs, are C3-C6alkylene or C3-C6alkenylene, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R19 and may be uninterrupted or interrupted by O, S or N(R14), or 1,4-buta-1,3-dienylene,
each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R,8 and in which 1 or 2 carbon atoms may have been replaced by nitrogen;
R11, R14 and R15 are each independently of the others C1-C24alkyl, C3-C24cycloalkyl, C2-C24alkenyl, C3-C24cycloalkenyl, C1-C4alkyl-[O-C1-C4alkylene]m or C1-C4alkyl-[NH-C1-C4alkylene]m, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R19;
or C6-C12aryl, C4-C12heteroaryl, C7-C12aralkyl or C5-C12heteroaralkyl, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R18;
R12, R13 and R18 are each independently of the others R20 or C1-C12alkyl, C3-C12cycloalkyl, C1-C12alkylthio, C3-C12cycloalkylthio, C1-C12alkoxy or C3-C12cycloalkoxy each unsubstituted or substituted by one or more, where applicable identical or different, radicals R19;
R17 is hydrogen, halogen, cyano, hydroxy, C1-C12alkoxy, C3-C12cycloalkoxy, C1-C12alkylthio, C3-C12cycloalkylthio, amino, nitro, formyl, C(R16)═CR21R22, C(R16)═NR23, N═CR23R24, NHR25, NR26R27, COO—R26, carboxy, carbamoyl, CONH—R26, CONR26R27, R28, N═N—R28 or R29;
R19 is halogen, hydroxy, O—R26, O—CO—R26, S—R26, NH2, NH—R26, NR26R27, NH3+, NH2R26+, NHR26R27+. NR25R26R27+, NR26—CO—R25, NR26COOR25, cyano, formyl, COO—R26, carboxy, carbamoyl, CONH—R26, CONR26R27, ureido, NH—CO—NHR25, NR26—CO—NHR25, phosphato, PR25R26, POR25OR26, P(═O)OR25OR26, OPR25R26, OPR25OR26, OP(═O)OR25OR26, OPO3R26, OP(═O)OR25OR26, SO2R26, sulfato, sulfo, R28, N═N—R28, or C1-C12alkoxy or C1-C12cycloalkoxy each unsubstituted or mono- or poly-substituted by halogen;
R20 is halogen, nitro, cyano, thiocyanato, hydroxy, O—R23, O—CO—R23, S—R23, CHO, COR24, CHOR23OR30, CR24OR23OR30, R31, N═N—R31, N═CR23R24, N═CR21R22, C(R32)═NR23, C(R32)═NR21, C(R32)═CR21R22, NH2, NH—R23, NR23R24, NH3+, NH2R23+, NHR23R24+, NR23R24R30+, CONH2, CONHR23, CONR23R24, SO2R23, SO2NH2, SO2NHR23, SO2NR23R24, COOH, COOR23, OCOOR23, NHCOR23, NR23COR30, NHCOOR23, NR23COOR30, ureido, NR23—CO—NHR30, B(OH)2, B(OH)(OR23), B(OR23)OR30, phosphato, PR23R30, POR23OR30, P(═O)OR23OR30, OPR23R30, OPR23OR30, OP(═O)R23OR30, OP(═O)OR23OR30, OPO3R23, sulfato or sulfo;
R21, and R22 are each independently of the other NR26R27, CN, CONH2, CONHR23, CONR23R24 or COOR24;
R23, R24 and R30 are each independently of the others R31, or C1-C12alkyl, C3-C12cycloalkyl, C2-C12alkenyl or C3-C12cycloalkenyl each unsubstituted or substituted by one or more, where applicable identical or different, halogen, hydroxy, C1-C2alkoxy or C3-C12cycloalkoxy radicals;
or R16 and R23 together, R17 and R23 together and/or R23 and R30 together are C2-C12alkylene, C3-C12cycloalkylene, C2-C12alkenylene or C3-C12cycloalkenylene, each of which is unsubstituted or substituted by one or more, where applicable identical or different, halogen, hydroxy, C1-C12alkoxy or C3-C12cycloalkoxy radicals;
or
R23 and R24 together with the common nitrogen are pyrrolidine, piperidine, piperazine or morpholine, each of which is unsubstituted or mono- to tetra-substituted by C1-C4alkyl;
or carbazole, phenoxazine or phenothiazine, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R33;
R25, R26 and R27 are each independently of the others C1-C12alkyl, C3-C12cycloalkyl, C2-C12alkenyl, C3-C12cycloalkenyl, C6-C12aryl, C4-C12heteroaryl, C7-C12aralkyl or C5-C12heteroaralkyl;
or
R26 and R27 together with the common nitrogen are pyrrolidine, piperidine, piperazine or morpholine, each of which is unsubstituted or mono- to tetra-substituted by C1-C4alkyl;
R28 is C6-C12aryl, C4-C12heteroaryl, C7-C12aralkyl or C5-C12heteroaralkyl, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R20 or R29;
R29 is C1-C12alkyl, C3-C12cycloalkyl, C2-C12alkenyl or C3-C12cycloalkenyl each unsubstituted or substituted by one or more, where applicable identical or different, halogen, hydroxy, C1-C12alkoxy or C3-C12cycloalkoxy radicals;
R31 is C6-C12aryl, C4-C12heteroaryl, C7-C12aralkyl or C5-C12heteroaralkyl, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R33;
R32 is hydrogen, cyano, hydroxy, C1-C12alkoxy, C3-C12cycloalkoxy, C1-C12alkylthio, C3-C12cycloalkylthio, amino, NHR25, NR26R27, R28, halogen, nitro, formyl, N═N—R28, COO—R26, carboxy, carbamoyl, CONH—R26, CONR26R27, N═CR23R24, or C1-C12alkyl, C3-C2cycloalkyl, C2-C12alkenyl or C3-C12cycloalkenyl each unsubstituted or substituted by one or more, where applicable identical or different, halogen, hydroxy, C1-C12alkoxy or C3-C12cycloalkoxy radicals;
R33 is nitro, SO2NHR26, SO2NR26R27, or C1-C12alkyl, C3-C12cycloalkyl, C1-C12alkylthio, C3-C12cycloalkylthio, C1-C12alkoxy or C3-C12cycloalkoxy each unsubstituted or substituted by one or more, where applicable identical or different, radicals R19;
and
m is a number from 1 to 10.

27 more elements

Dependencies are inferred from the claim text.

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Abstract

An optical recording medium comprising a substrate, a recording layer and optionally one or more reflecting layers, wherein the recording layer comprises a compound of formula

or a tautomer thereof, wherein
G1, G2 and G3 are each independently of the other
A1, A2 and A3 are each independently of the other N(R14), O, S or Se and A4 is C(C1-C5alkyl)2, C(C4-C5alkylene), N(R14), O, S, Se, N═C(R15) or CH═C(R16);
M1 is an at least trivalent metal of groups 3 to 15 [formerly groups IIIA to VB];
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 and R16 are each independently of the others hydrogen, R18, or C6-C12aryl, C4-C12heteroaryl, C7-C12aralkyl or C5-C12heteroaralkyl each unsubstituted or substituted by one or more, where applicable identical or different, radicals R18;
or
R1 and R2, R3 and R4, R5 and R6, R7 and R8, R7 and R15 and/or R7 and R16, together in pairs, are C3-C6alkylene or C3-C6alkenylene, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R19 and may be uninterrupted or interrupted by O, S or N(R14), or 1,4-buta-1,3-dienylene,
each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R,8 and in which 1 or 2 carbon atoms may have been replaced by nitrogen;
R11, R14 and R15 are each independently of the others C1-C24alkyl, C3-C24cycloalkyl, C2-C24alkenyl, C3-C24cycloalkenyl, C1-C4alkyl-[O-C1-C4alkylene]m or C1-C4alkyl-[NH-C1-C4alkylene]m, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R19;
or C6-C12aryl, C4-C12heteroaryl, C7-C12aralkyl or C5-C12heteroaralkyl, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R18;
R12, R13 and R18 are each independently of the others R20 or C1-C12alkyl, C3-C12cycloalkyl, C1-C12alkylthio, C3-C12cycloalkylthio, C1-C12alkoxy or C3-C12cycloalkoxy each unsubstituted or substituted by one or more, where applicable identical or different, radicals R19;
R17 is hydrogen, halogen, cyano, hydroxy, C1-C12alkoxy, C3-C12cycloalkoxy, C1-C12alkylthio, C3-C12cycloalkylthio, amino, nitro, formyl, C(R16)═CR21R22, C(R16)═NR23, N═CR23R24, NHR25, NR26R27, COO—R26, carboxy, carbamoyl, CONH—R26, CONR26R27, R28, N═N—R28 or R29;
R19 is halogen, hydroxy, O—R26, O—CO—R26, S—R26, NH2, NH—R26, NR26R27, NH3+, NH2R26+, NHR26R27+. NR25R26R27+, NR26—CO—R25, NR26COOR25, cyano, formyl, COO—R26, carboxy, carbamoyl, CONH—R26, CONR26R27, ureido, NH—CO—NHR25, NR26—CO—NHR25, phosphato, PR25R26, POR25OR26, P(═O)OR25OR26, OPR25R26, OPR25OR26, OP(═O)OR25OR26, OPO3R26, OP(═O)OR25OR26, SO2R26, sulfato, sulfo, R28, N═N—R28, or C1-C12alkoxy or C1-C12cycloalkoxy each unsubstituted or mono- or poly-substituted by halogen;
R20 is halogen, nitro, cyano, thiocyanato, hydroxy, O—R23, O—CO—R23, S—R23, CHO, COR24, CHOR23OR30, CR24OR23OR30, R31, N═N—R31, N═CR23R24, N═CR21R22, C(R32)═NR23, C(R32)═NR21, C(R32)═CR21R22, NH2, NH—R23, NR23R24, NH3+, NH2R23+, NHR23R24+, NR23R24R30+, CONH2, CONHR23, CONR23R24, SO2R23, SO2NH2, SO2NHR23, SO2NR23R24, COOH, COOR23, OCOOR23, NHCOR23, NR23COR30, NHCOOR23, NR23COOR30, ureido, NR23—CO—NHR30, B(OH)2, B(OH)(OR23), B(OR23)OR30, phosphato, PR23R30, POR23OR30, P(═O)OR23OR30, OPR23R30, OPR23OR30, OP(═O)R23OR30, OP(═O)OR23OR30, OPO3R23, sulfato or sulfo;
R21, and R22 are each independently of the other NR26R27, CN, CONH2, CONHR23, CONR23R24 or COOR24;
R23, R24 and R30 are each independently of the others R31, or C1-C12alkyl, C3-C12cycloalkyl, C2-C12alkenyl or C3-C12cycloalkenyl each unsubstituted or substituted by one or more, where applicable identical or different, halogen, hydroxy, C1-C2alkoxy or C3-C12cycloalkoxy radicals;
or R16 and R23 together, R17 and R23 together and/or R23 and R30 together are C2-C12alkylene, C3-C12cycloalkylene, C2-C12alkenylene or C3-C12cycloalkenylene, each of which is unsubstituted or substituted by one or more, where applicable identical or different, halogen, hydroxy, C1-C12alkoxy or C3-C12cycloalkoxy radicals;
or
R23 and R24 together with the common nitrogen are pyrrolidine, piperidine, piperazine or morpholine, each of which is unsubstituted or mono- to tetra-substituted by C1-C4alkyl;
or carbazole, phenoxazine or phenothiazine, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R33;
R25, R26 and R27 are each independently of the others C1-C12alkyl, C3-C12cycloalkyl, C2-C12alkenyl, C3-C12cycloalkenyl, C6-C12aryl, C4-C12heteroaryl, C7-C12aralkyl or C5-C12heteroaralkyl;
or
R26 and R27 together with the common nitrogen are pyrrolidine, piperidine, piperazine or morpholine, each of which is unsubstituted or mono- to tetra-substituted by C1-C4alkyl;
R28 is C6-C12aryl, C4-C12heteroaryl, C7-C12aralkyl or C5-C12heteroaralkyl, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R20 or R29;
R29 is C1-C12alkyl, C3-C12cycloalkyl, C2-C12alkenyl or C3-C12cycloalkenyl each unsubstituted or substituted by one or more, where applicable identical or different, halogen, hydroxy, C1-C12alkoxy or C3-C12cycloalkoxy radicals;
R31 is C6-C12aryl, C4-C12heteroaryl, C7-C12aralkyl or C5-C12heteroaralkyl, each of which is unsubstituted or substituted by one or more, where applicable identical or different, radicals R33;
R32 is hydrogen, cyano, hydroxy, C1-C12alkoxy, C3-C12cycloalkoxy, C1-C12alkylthio, C3-C12cycloalkylthio, amino, NHR25, NR26R27, R28, halogen, nitro, formyl, N═N—R28, COO—R26, carboxy, carbamoyl, CONH—R26, CONR26R27, N═CR23R24, or C1-C12alkyl, C3-C2cycloalkyl, C2-C12alkenyl or C3-C12cycloalkenyl each unsubstituted or substituted by one or more, where applicable identical or different, halogen, hydroxy, C1-C12alkoxy or C3-C12cycloalkoxy radicals;
R33 is nitro, SO2NHR26, SO2NR26R27, or C1-C12alkyl, C3-C12cycloalkyl, C1-C12alkylthio, C3-C12cycloalkylthio, C1-C12alkoxy or C3-C12cycloalkoxy each unsubstituted or substituted by one or more, where applicable identical or different, radicals R19;
and
m is a number from 1 to 10.

27 more elements