WO2002077984A1 - Optischer datenträger enthaltend in der informationsschicht einen xanthenfarbstoff als lichtabsorbierende verbindung - Google Patents

Optischer datenträger enthaltend in der informationsschicht einen xanthenfarbstoff als lichtabsorbierende verbindung Download PDF

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WO2002077984A1
WO2002077984A1 PCT/EP2002/003095 EP0203095W WO02077984A1 WO 2002077984 A1 WO2002077984 A1 WO 2002077984A1 EP 0203095 W EP0203095 W EP 0203095W WO 02077984 A1 WO02077984 A1 WO 02077984A1
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Prior art keywords
independently
hydrogen
methyl
another
alkyl
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PCT/EP2002/003095
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German (de)
English (en)
French (fr)
Inventor
Horst Berneth
Friedrich-Karl Bruder
Wilfried Haese
Rainer Hagen
Karin HASSENRÜCK
Serguei Kostromine
Peter Landenberger
Rafael Oser
Thomas Sommermann
Josef-Walter Stawitz
Thomas Bieringer
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Bayer AG
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Bayer AG
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Priority claimed from DE10115227A external-priority patent/DE10115227A1/de
Priority claimed from DE10117462A external-priority patent/DE10117462A1/de
Priority claimed from DE10136063A external-priority patent/DE10136063A1/de
Priority claimed from DE2001136064 external-priority patent/DE10136064A1/de
Priority claimed from DE2002102571 external-priority patent/DE10202571A1/de
Application filed by Bayer AG filed Critical Bayer AG
Priority to JP2002575938A priority Critical patent/JP2004523395A/ja
Priority to EP02724250A priority patent/EP1377974A1/de
Publication of WO2002077984A1 publication Critical patent/WO2002077984A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D221/00Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04Ortho- or peri-condensed ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D217/00Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/12Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78Ring systems having three or more relevant rings
    • C07D311/80Dibenzopyrans; Hydrogenated dibenzopyrans
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D455/00Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-condensed systems
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    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/06Cobalt compounds
    • C07F15/065Cobalt compounds without a metal-carbon linkage
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10The polymethine chain containing an even number of >CH- groups
    • C09B23/105The polymethine chain containing an even number of >CH- groups two >CH- groups
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0029Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/34Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
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    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00Azo dyes containing onium groups
    • C09B44/10Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
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    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/045Special non-pigmentary uses, e.g. catalyst, photosensitisers of phthalocyanine dyes or pigments
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    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/08Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/085Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex substituting the central metal atom
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    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/08Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/24Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
    • C09B47/26Amide radicals
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    • C09B69/00Dyes not provided for by a single group of this subclass
    • C09B69/02Dyestuff salts, e.g. salts of acid dyes with basic dyes
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02Organic tenebrescent materials
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/004Recording, reproducing or erasing methods; Read, write or erase circuits therefor
    • G11B7/0045Recording
    • G11B7/00455Recording involving reflectivity, absorption or colour changes
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/26Apparatus or processes specially adapted for the manufacture of record carriers
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/007Arrangement of the information on the record carrier, e.g. form of tracks, actual track shape, e.g. wobbled, or cross-section, e.g. v-shaped; Sequential information structures, e.g. sectoring or header formats within a track
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2533Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
    • G11B7/2534Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/254Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of protective topcoat layers
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/258Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers
    • G11B7/259Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers based on silver

Definitions

  • Optical data carrier containing a xanthene dye in the information layer as a light-absorbing compound
  • the invention relates to a write-once optical data carrier, which in the
  • Information layer as a light-absorbing compound contains a xanthene dye, and a process for their preparation.
  • the write-once optical data carriers using special light-absorbing substances or their mixtures are particularly suitable for use with high-density writable optical data storage devices that work with blue laser diodes, in particular GaN or SHG laser diodes (360 - 460 nm) and / or for use with DVD-R or CD-R discs that work with red (635 - 660 nm) or infrared (780 - 830 nm) laser diodes, as well as the application of the above-mentioned dyes to a polymer substrate, in particular polycarbonate
  • the next generation of optical data storage media - the DVD - is currently being launched on the market.
  • the storage density can be increased by using shorter-wave laser radiation (635 to 660 nm) and a higher numerical aperture NA.
  • the recordable format in this case is the DVD-R.
  • the patent literature describes dye-based writable optical data memories which are equally suitable for CD-R and DVD-R systems (JP-A 11 043 481 and JP-A 10 181 206).
  • JP-A 11 043 481 and JP-A 10 181 206 For a high reflectivity and a high modulation level of the readout signal, as well as for a sufficient sensitivity when writing, use is made of the fact that the IR wavelength 780 nm of the CD-R lies at the foot of the long-wave flank of the absorption peak of the dye.
  • the red wavelength 635 nm or 650 nm of the DVD-R lies at the foot of the short-wave flank of the absorption peak of the dye.
  • the writable information layer made of light-absorbing organic substances must have a morphology which is as amorphous as possible in order to keep the noise signal as small as possible when writing or reading.
  • the substances are applied by spin coating from a solution, by vapor deposition and / or sublimation, subsequent crystallization of the light-absorbing substances with metallic or dielectric layers in vacuum is prevented.
  • the amorphous layer of light-absorbing substances should preferably have a high heat resistance, since otherwise further layers of organic or inorganic material, which are applied to the light-absorbing information layer by sputtering or vapor deposition, are diffused by diffusion
  • An excessively high vapor pressure of a light-absorbing substance can sublimate the above-mentioned sputtering or vapor deposition of further layers in a high vacuum and thus reduce the desired layer thickness. This in turn leads to a negative influence on the reflectivity.
  • the object of the invention is therefore to provide suitable compounds which meet the high requirements (such as light stability, favorable signal-to-noise ratio, damage-free application to the substrate material, etc.) for use in the information layer in a write-once optical data carrier, in particular for high-density recordable optical media Meet data storage formats in a laser wavelength range from 340 to 680 nm.
  • a high capacity optical storage medium containing xanthene dyes is known from EP-A-0 805 441.
  • the claimed xanthene dyes can have up to four positive or negative excess charges and corresponding counterions.
  • a proton or a metal, ammonium or phosphonium cation are described as cationic counterions.
  • light-absorbing compounds from the group of xanthene dyes which contain at least two anionic groups and have at least one cation as counterion, which contains at least one specific conjugated ⁇ system with at least 6 ⁇ electrons, meet the requirement profile mentioned above can meet particularly well.
  • the invention therefore relates to an optical data carrier, comprising a preferably transparent substrate, possibly already coated with one or more reflection layers, on the surface of which a surface can be written on with light Information layer, optionally one or more reflection layers and optionally a protective layer or another substrate or a cover layer are applied, which can be written and read with blue or red light, preferably laser light, the information layer containing a light-absorbing compound and optionally a binder, thereby characterized in that at least one xanthene dye is used as the light-absorbing compound, which contains at least two anionic groups and has at least one cation as the counter ion, which contains at least one conjugated ⁇ system with at least 6 ⁇ electrons, with the proviso that the cation is not a benzyl tri methylammonium, benzyltriethylammonium, tetraphenylphosphomum,
  • Butyltriphenylphosphonium or Ethyltriphenylphosphomum is.
  • the light-absorbing compound should preferably be thermally changeable.
  • the thermal change preferably takes place at a temperature ⁇ 600 ° C., particularly preferably at a temperature ⁇ 400 ° C., very particularly preferably at one
  • Such a change can be, for example, a decomposition or chemical change in the chromophoric center of the light-absorbing compound.
  • a xanthene dye of the formula (I) is preferred
  • R 1 to R 4 independently of one another for hydrogen, Ci to C 16 alkyl, C 3 to C 6 -
  • NR'R 2 or NR 3 R 4 independently of one another represent a five- or six-membered saturated ring which is attached via N and which may additionally contain an N or O and / or may be substituted by nonionic radicals,
  • R 5 to R 10 independently of one another are hydrogen, halogen, C 1 -C 16 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, cyano or nitro or
  • R; R, R; R, R; R or R; R independently of one another represent a two- or three-membered bridge which may contain an N or O and / or which may be substituted by nonionic radicals,
  • R 11 represents hydrogen, d to C 6 alkyl, C 5 to C 7 cycloalkyl, C 6 to C 0 aryl or a heterocyclic radical which can be substituted by nonionic radicals or an anionic group X " ,
  • X represents an anionic group of the formulas -COO " , -SO “ or -O-SO 3 " or an equivalent of the di-anionic groups of the formulas -PO 3 2 " or -O-PO 3 2" ,
  • M + stands for a cation or an equivalent of a polycation which contains at least one conjugated ⁇ system with at least 6 ⁇ electrons
  • M + does not represent benzyltrimethylammonium, benzyltriethylammonium, tetraphenylphosphonium, butyltriphenylphosphonium or ethyltriphenylphosphonium.
  • nonionic radicals are Ci to C 4 alkyl, Ci to C alkoxy, halogen, cyano, nitro, Ci to C alkoxycarbonyl, Ci to C 4 alkylthio, C to C 4 alkanoylamino, benzoylamino, Mono- or di-Ci to C 4 alkylamino in question.
  • Alkyl radicals including those in alkoxy, alkylthio or aralkyl, also those that later in
  • Text mentioned can be straight or branched.
  • Heterocyclic radicals are furyl, thienyl, pyridyl or a radical of the formula
  • Alkyl, alkoxy, aryl and heterocyclic radicals can optionally carry further radicals, such as alkyl, halogen, nitro, cyano, CO-NH 2 , alkoxy, trialkylsilyl, trialkylsiloxy or phenyl, which alkyl and alkoxy radicals can be straight-chain or branched, the alkyl radicals can be partially or perhalogenated, the alkyl and alkoxy radicals can be ethoxylated or propoxylated or silylated, adjacent alkyl and / or alkoxy radicals on aryl or heterocyclic radicals can together form a three- or four-membered radical Form a bridge and the heterocyclic radicals can be benzannelated and / or quaternized.
  • further radicals such as alkyl, halogen, nitro, cyano, CO-NH 2 , alkoxy, trialkylsilyl, trialkylsiloxy or phenyl, which alkyl
  • a cation or an equivalent of a polycation which contains at least one conjugated ⁇ system with at least 6 ⁇ electrons is preferably to be understood
  • anilinium salts diphenyliodonium, thien-2-yl-trimethylammonium
  • pyridinium salts quinolinium salts, benzothiazolium salts, dithiolium salts
  • bipyridinium salts Chinodiimmoniumsalze, Metallocenyle as ferrocenyl (Fe m (C 5 H 5) 2 +), Manganocenyl (Mn, II (CO) 3 C 5 H 5 + ), d) cationic organic dyes.
  • Aromatic and heteroaromatic substituents mean, for example: phenyl, tolyl, anisyl, chlorophenyl, naphthyl, furyl, thienyl, pyridyl, quinolyl.
  • Cationic organic dyes can, for example, come from the classes of cyanines, streptocyanines, hemicyanines, diazahemicyanines, zero methines, enamine dyes, hydrazone dyes, di- or tri (het) arylmethane dyes, xanthene dyes, azine dyes (phenazines, oxazines, thiazines) or, for example, the
  • Classes of azo dyes, anthraquinone dyes, neutrocyanines, porphyrins or phthalocyanines come from if they carry at least one localized positive charge.
  • Such dyes are disclosed, for example H. Berneth, Cationic Dyes in Ullmann's Encyclopedia of Industrial Chemistry, VCH, th edition sixth
  • the oxidation stage OX and the radical stage SEM are suitable as cations M + , provided they are cationic.
  • R 1 to R 4 independently of one another are hydrogen, methyl, ethyl, propyl, butyl, chloroethyl, cyanoethyl, hydroxyethyl, hydroxypropyl, -CH 2 CH 2 COO ⁇ -CH 2 CH 2 CH 2 COO ⁇ -CH 2 CH 2 CH 2 CH 2 COO ⁇ -CH 2 CH 2 SO 3 " ,
  • NR'R 2 or NR 3 R 4 independently of one another represent pyrrolidino, piperidino, morpholino, piperazino or N-methylpiperazino,
  • R 5 to R 10 independently of one another represent hydrogen, chlorine, methyl or methoxy or
  • R 11 for hydrogen, -CH 2 CH 2 COO-, -CH 2 CH 2 CH 2 COO ⁇
  • radicals R 1 to R 4 and R 11 contain a total of at least two -COO " or -SO 3 " groups, represents a cation or an equivalent of a polycation of one of the following formulas,
  • R 21 to R 23 , R 36 , R 37 , R 39 to R 42 , R 51 to R 54 , R 57 , R 61 to R 66 , R 72 , R 73 , R 72 ' , R 73' , R 76 , R 77 , R 80 and R 81 independently of one another for hydrogen, d- to C 16 - Alkyl, C - to C 6 -alkenyl, C 5 - to C 7 -cycloalkyl, C 7 - to -CC 6 aralkyl or C 6 - to Cio-aryl, which can be substituted by nonionic radicals or
  • two adjacent radicals together with the nitrogen atom connecting them independently represent a five- or six-membered saturated ring which is bonded via N and which may additionally contain an N or O and / or may be substituted by nonionic radicals,
  • R 25 to R 27 , R 32 , R 33 and R 78 independently of one another for d- to C 16 -alkyl, C 3 - bis
  • R 28 for hydrogen, chlorine, amino, Ci to C 16 alkyl, C 3 to C 6 alkenyl, C 5 to C 7 cycloalkyl, C 7 to C ] 6 aralkyl or C 6 to Cio -Aryl stands,
  • R 24 , R 24 ' , R 29 to R 31 , R 34 , R 35 and R 79 independently of one another for hydrogen, halogen, Ci to C 8 alkyl, C ⁇ to C 8 alkoxy, Ci to C 4 -Alkylthio, Cyano or Nitro stand or
  • R 38 , R 55 and R 56 independently of one another are hydrogen, halogen, Ci to C 4 alkyl, d to C 4 alkoxy, cyano, nitro, d to C 4 alkoxycarbonyl, Ci to C 4
  • alkanoylamino or Ci to C 4 -alkanesulfonylamino and R can form a - (CH 2 ) 2 - or - (CH 2 ) 3 bridge with R,
  • R 43 to R 48 , R 60 , R 67 , R 68 and R 82 independently of one another represent hydrogen, halogen, Ci to C 8 alkyl, d to C 8 alkoxy or Ci to C 4 alkylthio and R 43 with R 39 , R 44 with R 40 , R 46 with R 41 , R 47 with R 41 , R 67 with R 63 , R 68 with R 65 and R 82 with R 80 a - (CH 2 ) 2 - or - ( CH 2 ) 3 bridge can form
  • R 49 , R 74 and R 74 independently of one another are hydrogen, Ci to C 16 alkyl, C to C 7 cycloalkyl or C 6 to C 0 aryl, which by nonionic
  • Residues can be substituted,
  • Y 5 and Y 6 independently of one another represent O, S, NR 57 or CR 58 R 59 ,
  • Z, Y 7 and Y 7 independently of one another represent N, CH or C-CN,
  • Y 8 and Y 8 independently of one another represent O or S,
  • R 58 and R 59 independently of one another represent hydrogen or C 1 -C 4 -alkyl or
  • B 2 represents a direct bond
  • -CH CH-, -C ⁇ C- or thien-2,5-diyl
  • Het represents a five- or six-membered aromatic or quasi-aromatic heterocyclic ring which contains 1 to 3 heteroatoms of the N, O or S series and which is benzannelated and / or substituted by up to three nonionic radicals,
  • n represents an integer from 1 to 3, where, if m> 1, the radicals indicated with m can have different meanings and
  • n an integer from 1 to 2.
  • heterocyclic rings Het are thiazolyl, benzthiazolyl, thienyl, benzothienyl, pyrazolyl, thiadiazolyl, pyridyl.
  • radical-cationic oxidation state SEM of the formula corresponding to formula (XXV) is also suitable as M 1 "
  • the xanthene dyes used are those of the formula (II)
  • R 1 to R 4 independently of one another are hydrogen, methyl, ethyl, propyl, butyl,
  • NR'R 2 or NR 3 R 4 independently of one another represent pyrrolidino, piperidino or morpholino,
  • R 5, ⁇ R, 6, n R8 and R independently of one another represent hydrogen, methyl or methoxy or
  • R 21 to R 23 , R 36 , R 37 , R 39 to R 42 , R 57 , R 61 to R 66 , R 72 , R 73 , R 72 ' , R 73' , R 76 , R 77 , R 80 and R 81 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclohexyl, benzyl or phenyl or
  • NR 21 R 22 , NR 36 R 37 NR 39 R 40 , NR 41 R 42 , NR 61 R 62 and NR 80 R 81 independently of one another represent pyrrolidino, piperidino or morpholino,
  • R 5 to R, R 32 , R 3 and R independently of one another represent methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclohexyl or benzyl,
  • R 24 , R 24 ' , R 34 , R 35 and R 79 independently of one another represent hydrogen, chlorine, methyl, methoxy, cyano or nitro or
  • R 30 and R 31 are the same and represent methyl, ethyl, propyl, 2-propyl, butyl or tert-butyl,
  • R for hydrogen, chlorine, methyl, methoxy, cyano, nitro, methoxycarbonyl
  • R 43 to R 48 , R 67 , R 68 and R 82 independently of one another represent hydrogen, chlorine, methyl or methoxy,
  • R 49 , R 74 and R 74 independently of one another represent methyl, cyclohexyl or phenyl
  • B 1 stands for a direct bond
  • Y ° represents O, S or NR 5 3 7 '
  • R 58 and R 59 are the same and represent methyl
  • Y 8 and Y 8 stand for O or S and are the same,
  • R 69 represents hydrogen or a radical of the formula
  • R 75 for hydrogen or for a radical of the formulas
  • n represents an integer from 1 to 3, where, if m> 1, the radicals indicated with m can have different meanings.
  • the xanthene dyes used are those of the formula (II-A)
  • R 1 to R 4 and R 21 to R 23 independently of one another represent hydrogen, methyl, ethyl, propyl or butyl or
  • NR R, NR R or NR R independently of one another represent pyrrolidino, piperidino or morpholino
  • R, 5, R, R and R independently of one another represent hydrogen or methyl or
  • R '; R 5 , R 2 ; R °, R 3 ; R 8 or R 4 ; R 9 independently of one another represent a -CH 2 CH 2 CH 2 bridge,
  • R, 24 stands for hydrogen, methyl or methoxy or two adjacent radicals
  • n 1 to 2.
  • the xanthene dyes used are those of the formula (II-B)
  • R 1 to R 4 and R 25 independently of one another represent hydrogen, methyl, ethyl, propyl or butyl or NR'R 2 or NR 3 R 4 independently of one another represent pyrrolidino, piperidino or mo holino,
  • R, R, R and R independently of one another represent hydrogen or methyl or
  • R '; R 5 , R 2 ; R 6 , R 3 ; R 8 or R 4 ; R 9 independently of one another represent a -CH 2 CH 2 CH 2 bridge,
  • R »24 stands for hydrogen, methyl or methoxy or two adjacent radicals
  • n 1 to 2.
  • the xanthene dyes used are those of the formula (II-C)
  • R 1 to R 4 , R 25 and R 26 independently of one another represent hydrogen, methyl, ethyl, propyl or butyl or NR'R 2 or NR 3 R 4 independently of one another represent pyrrolidino, piperidino or morpholino,
  • R, 5, R, R and R independently of one another represent hydrogen or methyl or
  • R '; R 5 , R 2 ; R 6 , R 3 ; R 8 or R 4 ; R 9 independently of one another represent a -CH 2 CH 2 CH 2 bridge,
  • R 24 stands for hydrogen, methyl or methoxy or two adjacent radicals
  • n 1 to 2.
  • the xanthene dyes used are those of the formula (II-D)
  • R 1 to R 4 independently of one another represent hydrogen, methyl, ethyl, propyl or butyl or NR'R 2 or NR 3 R 4 independently of one another represent pyrrolidino, piperidino or morpholino,
  • R 5, R r 6, R and R independently of one another represent hydrogen or methyl or
  • R '; R 5 , R 2 ; R °, R 3 ; R 8 or R 4 ; R 9 independently of one another represent a -CH 2 CH 2 CH 2 bridge and
  • R 24 represents hydrogen, methoxy, ethoxy, butoxy or octoxy.
  • the xanthene dyes used are those of the formula (II-E)
  • R to R independently of one another represent hydrogen, methyl, ethyl, propyl or butyl or
  • R 2 or NR 3 R 4 independently of one another represent pyrrolidino, piperidino or morpholino,
  • R> 5, ⁇ R> 6, ⁇ R) 8 and, R r, 9 independently of one another represent hydrogen or methyl or R '; R 5 , R 2 ; R 6 , R 3 ; R 8 or R 4 ; R 9 independently of one another represent a -CH 2 CH 2 CH 2 bridge and
  • R and R are the same and represent hydrogen, methyl or tert-butyl.
  • the xanthene dyes used are those of the formula (II-F)
  • R 1 to R 4 , R 32 and R 33 independently of one another represent hydrogen, methyl, ethyl, propyl or butyl or
  • NR'R 2 or NR 3 R 4 independently of one another represent pyrrolidino, piperidino or morpholino,
  • R 5, R, R and R independently of one another represent hydrogen or methyl or
  • n 1 or 2
  • the xanthene dyes used are those of the formula (II-G)
  • R 1 to R 4 , R 32 , R 36 and R 37 independently of one another represent hydrogen, methyl, ethyl, propyl or butyl or
  • NR R, NR 3 R and NR R independently of one another represent pyrrolidino, piperidino or morpholino and R »36 additionally represents phenyl, methoxyphenyl or ethoxyphenyl,
  • R, 5, R, R and R independently of one another represent hydrogen or methyl or
  • R '; R 5 , R 2 ; R 6 , R 3 ; R 8 or R 4 ; R 9 independently of one another represent a -CH 2 CH 2 CH 2 bridge and
  • R, 34 represents hydrogen, methyl, methoxy or methoxycarbonyl
  • R, 38 represents hydrogen, methyl, methoxy, cyano, acetylamino or methanesulfonylamino
  • the xanthene dyes used are those of the formula (II-H)
  • R 1 to R 4 and R 39 to R 42 independently of one another represent hydrogen, methyl, ethyl, propyl or butyl or NR'R 2 , NR 3 R 4 , NR 39 R 40 and NR 41 R 42 independently of one another represent pyrrolidino, piperidino or morpholino,
  • R 5 , R 6 , R 8 , R 9 , R 43 , R 44 , R 46 and R 47 are independently hydrogen or
  • R 45 and R 48 represent hydrogen and
  • R, 49 represents hydrogen, methyl or phenyl.
  • the xanthene dyes used are those of the formula (II-J)
  • R to R and R to R independently of one another represent hydrogen, methyl, ethyl, propyl or butyl or
  • NR J R 2 , NR 3 R 4 , NR 63 R ° 4 and NR 65 R 66 independently of one another represent pyrrolidino, piperidino or morpholino
  • R 5 , R 6 , R 8 , R 9 , R 67 and R 68 independently of one another represent hydrogen or methyl or
  • R '; R 5 , R 2 ; R 6 , R 3 ; R 8 , R 4 ; R 9 , R 63 ; R 67 and R 65 ; R 68 independently of one another represent a - CH 2 CH 2 CH 2 bridge,
  • R 69 represents hydrogen, phenyl, 2-chloro-phenyl, 4-dimethylaminophenyl, 4-diethylaminophenyl, 4-anilinophenyl, naphthyl, 4-dimethylaminonaphthyl or 4-anilinonaphthyl.
  • the xanthene dyes used are those of the formula (II-K)
  • R 1 to R 4 , R 72 , R 73 , R 72 ' and R 73' independently of one another represent hydrogen, methyl, ethyl, propyl or butyl, where R 72 and R 72 or R 73 and R 73 are the same or
  • R 2 , NR 3 R 4 , NR 72 R 73 and NR 72 R 73 ' independently of one another are py ⁇ olidino, piperidino or Mo ⁇ holino, where NR 72 R 73 and NR 72 R 73 are the same,
  • R 5 , R 6 , R 8 and R 9 independently of one another represent hydrogen or methyl or R ⁇ R 5 , R 2 ; R 6 , R 3 ; R 8 and R 4 ; R 9 independently of one another represent a -CH 2 CH 2 CH 2 bridge,
  • Y 8 and Y 8 are the same and stand for S,
  • R 74 and R 74 ' are identical and represent hydrogen, methyl, ethyl, propyl, butyl or phenyl,
  • R 75 represents hydrogen, phenyl, 4-dimethylaminophenyl or 4-diethylaminophenyl and
  • the xanthene dyes used are those of the formula (II-L) embedded image in which
  • R 1 to R 4 , R 80 and R 81 independently of one another represent hydrogen, methyl, ethyl, propyl or butyl or
  • NR'R 2 , NR 3 R 4 and NR 80 R 81 independently of one another represent pyrrolidino, piperidino or Mo ⁇ holino,
  • R 7'8 8 represents methyl, ethyl, benzyl, cyanoethyl or hydroxyethyl
  • R »5, R, R, R and R» 82 independently of one another represent hydrogen or methyl or
  • R '; R 5 , R 2 ; R 6 , R 3 ; R 8 , R 4 ; R 9 and R 80 ; R 82 independently of one another represent a - CH 2 CH 2 CH 2 bridge, the bridge R 80 ; R 82 can be substituted by 1 to 3 methyl groups, and
  • R represents hydrogen or bromine.
  • those xanthene dyes are preferred whose absorption maximum ⁇ m j u is in the range 420 to 550 nm, the wavelength ⁇ / 2 at which the extinction in the short-wave flank of the absorption maximum of the wavelength ⁇ m a ⁇ half of the absorbance value ⁇ max2 , and the wavelength ⁇ y ⁇ 0 , at which the extinction in the short-wave flank of the absorption maximum of the wavelength ⁇ max2 is one tenth of the extinction value at ⁇ maX2 , preferably not more than 50 nm apart.
  • Such a xanthene dye preferably has no shorter-wave maximum ⁇ max ⁇ up to a wavelength of 350 nm, particularly preferably up to 320 nm, very particularly preferably up to 290 nm.
  • Xanthene dyes with an absorption maximum ⁇ ma ⁇ 2 of 410 to 530 nm are preferred.
  • Xanthene dyes with an absorption maximum ⁇ maX2 of 420 to 510 nm are particularly preferred.
  • Xanthene dyes with an absorption maximum ⁇ maX 2 of 430 to 500 nm are very particularly preferred.
  • ⁇ ⁇ a and ⁇ no are preferably not more than 40 nm apart, particularly preferably not more than 30 nm apart, very particularly preferably not more than 20 nm apart.
  • xanthene dyes for a write-once optical data carrier according to the invention which is written and read with the light of a red laser, preference is given to xanthene dyes whose absorption maximum ⁇ maX2 is in the range from 500 to 650 nm, the wavelength ⁇ / 2 at which the absorbance in the long-wave flank of the absorption maximum of the wavelength ⁇ ma ⁇ 2 is half the extinction value at max2 , and the wavelength ⁇ ] / ⁇ 0 , at which the extinction in the long-wave flank of the absorption maximum of the wavelength ⁇ maX2 is one tenth of the extinction value at ⁇ max2 are preferably no more than 50 nm apart.
  • Such a xanthene dye preferably has a wavelength of up to 750 nm, particularly preferably up to 800 nm, very particularly preferably up to 850 nm, no longer-wave maximum ⁇ max3 .
  • Xanthene dyes with an absorption maximum ⁇ max2 of 530 to 630 nm are preferred.
  • Xanthene dyes with an absorption maximum ⁇ max2 of 550 to 620 nm are particularly preferred.
  • Xanthene dyes with an absorption maximum ⁇ m ax2 of 580 to 610 nm are very particularly preferred.
  • ⁇ 2 and ⁇ ] / 10 are preferably not more than 40 nm apart, more preferably not more than 30 nm apart, very particularly preferably not more than 20 nm apart.
  • the xanthene dyes have a molar extinction coefficient ⁇ > 40,000 l / mol cm, preferably> 60,000 l / mol cm, particularly preferably> 80,000 l / mol cm, very particularly preferably> 100,000 l / mol cm.
  • the absorption spectra are measured, for example, in solution.
  • Xanthene dyes of the formula (I) with cations other than the invention are known in some cases.
  • Another object of the invention are xanthene dyes of the formula (I), in which the substituents have the general, special and very special meanings given above and the provisions given above apply.
  • the xanthene dyes of the formula (I) are prepared, for example, by
  • M + represents a cation M + not according to the invention, for example an alkali metal ion such as Li + , Na + , K + , a proton H * or an ammonium ion such as NH 4 + , trimethylammonium or tetramethylammonium,
  • M + has the meaning according to the invention given above and Z " stands for an anion, for example for chloride, bromide, hydrogen sulfate, V% sulfate, methosulfate, acetate or tetrafluoroborate,
  • Suitable solvents are for example water, alcohols such as methanol, ethanol, propanol, methoxyethanol, methoxypropanol, nitriles such as acetonitrile, amides such as dimethylformamide, N-methylpyrrolidone and esters such as ⁇ -butyrolactone or mixtures thereof.
  • Formula (I) is that xanthene dyes of the formula (I), in which M + stands for a cation M + not according to the invention, for example for an alkali metal ion such as Li + , Na + , K + , a proton H + or an ammonium ion such as NH + , Trimethylammonium or tetramethylammonium, can be reacted with cation exchangers which are loaded with the cations M + according to the invention.
  • Suitable solvents are also those described above. This process is advantageous if the xanthene dyes of the formula (I) according to the invention are readily soluble in the solvent selected. They are then isolated, for example, by stripping off the solvent or by precipitation with a solvent in which they are sparingly soluble.
  • solvents can e.g. B. aromatics such as toluene or
  • Be esters such as ethyl acetate.
  • the light-absorbing substances described guarantee a sufficiently high reflectivity (> 10%) of the optical data carrier in the blank state and a sufficiently high absorption for the thermal degradation of the information layer in the case of selective illumination with focused light if the light wavelength is in the range from 360 to 460 nm and 600 to 680 nm.
  • the contrast between written and unwritten points on the data carrier is realized by the change in reflectivity of the amplitude as well as the phase of the incident light by the optical properties of the information layer which have changed after thermal degradation.
  • the xanthene dyes are preferably applied to the optical data carrier by spin coating.
  • the xanthene dyes can be mixed with one another or with other dyes with similar spectral properties. In particular, dyes can also be mixed with different cations.
  • the information layer can contain additives such as binders, wetting agents, stabilizers, thinners and sensitizers and other constituents.
  • the optical data storage device can carry further layers such as metal layers, dielectric layers and protective layers.
  • Metals and dielectric layers serve u. a. to adjust the reflectivity and the heat balance. Depending on the laser wavelength, metals can be gold, silver, aluminum and the like. a. his.
  • Dielectric layers are, for example, silicon dioxide and silicon nitride.
  • Protective layers are, for example photocurable, lacquers (pressure sensitive)
  • Adhesive layers and protective films are Adhesive layers and protective films.
  • Pressure-sensitive adhesive layers mainly consist of acrylic adhesives. Nitto Denko DA-8320 or DA-8310, disclosed in patent JP-A 11-273147, can be used for this purpose, for example.
  • the optical data carrier has, for example, the following layer structure (cf. FIG. 1): a transparent substrate (1), optionally a protective layer (2), an information layer (3), optionally a protective layer (4), optionally an adhesive layer (5), a cover layer (6).
  • the structure of the optical data carrier can preferably:
  • a preferably transparent substrate (1) on the surface of which at least one information layer (3) which can be written on with light and which can be written on with light, preferably laser light, optionally one
  • Protective layer (4) optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
  • a transparent substrate (1) on the surface of which a protective layer (2), at least one information layer (3) which can be written on with light, preferably laser light, optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
  • a transparent substrate (1) on the surface of which there is optionally a protective layer (2), at least one information layer (3) which can be written on with light, preferably laser light, optionally a protective layer (4), optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
  • a preferably transparent substrate (1) on the surface of which at least one information layer (3) which can be written on with light, preferably laser light, optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
  • the optical data carrier has, for example, the following layer structure
  • a preferably transparent substrate 11
  • an information layer (12)
  • optionally a reflection layer 13
  • optionally an adhesive layer 14
  • another preferably transparent substrate 15
  • the invention further relates to optical data carriers according to the invention described with blue or red light, in particular laser light.
  • Suitable xanthene dyes are listed in the table, which can be prepared analogously to Example 1:
  • a 4% by weight solution of the dye from Example 15 in 2,2,3,3-tetrafluoropropanol was prepared at room temperature. This solution was applied to a pregrooved polycarbonate substrate using spin coating. The pregrooved polycarbonate substrate was produced as a disk using injection molding. The dimensions of the disc and the groove structure corresponded to those which are usually used for DVD-R.
  • the disk with the dye layer as the information carrier was sputtered with 100 nm silver.
  • the write power was applied as an oscillating pulse sequence, the disk being alternately irradiated for 1 ⁇ s with the above-mentioned write power P w and for 4 ⁇ s with the read power P r »0.6 mW.
  • the disc was irradiated with this oscillating pulse sequence until it had turned around once.
  • the marking generated in this way was then read out with the reading power P r and the above-mentioned signal-to-noise ratio C / N was measured.

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Publication number Priority date Publication date Assignee Title
EP1516895A1 (en) * 2003-09-19 2005-03-23 Clariant International Ltd. New coumarin type dyes for optical data recording
WO2006120205A3 (en) * 2005-05-10 2007-02-01 Clariant Int Ltd Anionic phthalocyanine based dyes for use as bca dye in an optical recording layer for blue laser recording
AU2006201909B2 (en) * 2005-05-09 2008-12-04 Dell Products L.P. System and Method For Multi-Laser Optical Medium
CN102838578A (zh) * 2011-06-24 2012-12-26 住友化学株式会社 盐及着色固化性组合物
KR101927875B1 (ko) * 2016-04-21 2018-12-18 (주)켐이 크산텐계 염료 화합물 및 이를 포함하는 포토레지스트 조성물

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EP1506547A1 (en) * 2002-05-17 2005-02-16 Ciba Specialty Chemicals Holding Inc. High-performance optical storage media
CN1653531A (zh) * 2002-05-17 2005-08-10 西巴特殊化学品控股有限公司 由五环呫吨鎓染料组成的光学存储介质
KR20060028434A (ko) * 2003-06-27 2006-03-29 시바 스페셜티 케미칼스 홀딩 인크. 저장 밀도가 높은 광학 기록 재료
US7391691B2 (en) * 2003-08-29 2008-06-24 General Electric Company Method for facilitating copyright protection in digital media and digital media made thereby
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US7459259B2 (en) 2004-09-29 2008-12-02 Sabic Innovative Plastics Ip B.V. Marked article and method of making the same
US20060072444A1 (en) * 2004-09-29 2006-04-06 Engel David B Marked article and method of making the same
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JPWO2012008360A1 (ja) * 2010-07-13 2013-09-09 Jsr株式会社 着色剤、着色組成物、カラーフィルタ及び表示素子
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US20230287217A1 (en) * 2020-10-06 2023-09-14 Oregon Health & Science University Zwitterionic Cell-Permeant and Water-Soluble Rhodamine Dyes for Quantitative Imaging Applications
JP2023150459A (ja) * 2022-03-31 2023-10-16 保土谷化学工業株式会社 トリアリールメタン色素、該色素を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1057594A (en) * 1964-05-21 1967-02-01 Edward Gurr Ltd Improvements in or relating to dyes and stains
US4656121A (en) * 1984-02-06 1987-04-07 Ricoh Co., Ltd. Optical information recording medium
US4924009A (en) * 1987-06-03 1990-05-08 Bowling Green State University Xanthene dye complexes
EP0542420A1 (en) * 1991-11-15 1993-05-19 Zeneca Limited Anionic xanthene derivatives and their use in inks
EP0805441A1 (de) * 1996-05-03 1997-11-05 Ciba SC Holding AG Optische Speichermedien mit hoher Kapazität, die Xanthenfarbstoffe enthalten
US6020105A (en) * 1996-10-08 2000-02-01 Fuji Photo Film Co., Ltd. Information recording medium

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1006738A (en) * 1910-12-30 1911-10-24 Hoechst Ag Red acid dyestuff of the triphenylmethane series and process of making same.
US3367946A (en) * 1964-10-22 1968-02-06 Du Pont Xanthene dyes
US4304834A (en) * 1979-12-26 1981-12-08 Polaroid Corporation Novel xanthene compounds and photographic products and processes employing the same
US4290950A (en) * 1979-12-26 1981-09-22 Polaroid Corporation Sulfo-substituted-3,6-di(N-indolinyl)-9-sulfonamidophenyl-xanthenes
JPS59106989A (ja) * 1982-12-10 1984-06-20 Ricoh Co Ltd インクジエツト記録法
JPS60199079A (ja) * 1984-03-22 1985-10-08 Ricoh Co Ltd インクジエツト用水性インク
JPH06105342B2 (ja) * 1986-12-01 1994-12-21 富士写真フイルム株式会社 発光性色素によつて増感されたハロゲン化銀感光材料
EP0540468B1 (de) * 1991-10-30 1996-12-04 Ciba-Geigy Ag NIR-Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
US6130101A (en) * 1997-09-23 2000-10-10 Molecular Probes, Inc. Sulfonated xanthene derivatives
CN1108304C (zh) * 1997-09-26 2003-05-14 复旦大学 蓝光dvd-r用光信息存贮材料

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1057594A (en) * 1964-05-21 1967-02-01 Edward Gurr Ltd Improvements in or relating to dyes and stains
US4656121A (en) * 1984-02-06 1987-04-07 Ricoh Co., Ltd. Optical information recording medium
US4924009A (en) * 1987-06-03 1990-05-08 Bowling Green State University Xanthene dye complexes
EP0542420A1 (en) * 1991-11-15 1993-05-19 Zeneca Limited Anionic xanthene derivatives and their use in inks
EP0805441A1 (de) * 1996-05-03 1997-11-05 Ciba SC Holding AG Optische Speichermedien mit hoher Kapazität, die Xanthenfarbstoffe enthalten
US6020105A (en) * 1996-10-08 2000-02-01 Fuji Photo Film Co., Ltd. Information recording medium

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1516895A1 (en) * 2003-09-19 2005-03-23 Clariant International Ltd. New coumarin type dyes for optical data recording
AU2006201909B2 (en) * 2005-05-09 2008-12-04 Dell Products L.P. System and Method For Multi-Laser Optical Medium
WO2006120205A3 (en) * 2005-05-10 2007-02-01 Clariant Int Ltd Anionic phthalocyanine based dyes for use as bca dye in an optical recording layer for blue laser recording
CN102838578A (zh) * 2011-06-24 2012-12-26 住友化学株式会社 盐及着色固化性组合物
CN102838578B (zh) * 2011-06-24 2016-03-16 住友化学株式会社 盐及着色固化性组合物
KR101927875B1 (ko) * 2016-04-21 2018-12-18 (주)켐이 크산텐계 염료 화합물 및 이를 포함하는 포토레지스트 조성물

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EP1377974A1 (de) 2004-01-07

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