EP1374233A1 - Optical data carrier that contains a triazacyanine dye as the light-absorbing compound in the information layer g - Google Patents

Optical data carrier that contains a triazacyanine dye as the light-absorbing compound in the information layer g

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Publication number
EP1374233A1
EP1374233A1 EP02735147A EP02735147A EP1374233A1 EP 1374233 A1 EP1374233 A1 EP 1374233A1 EP 02735147 A EP02735147 A EP 02735147A EP 02735147 A EP02735147 A EP 02735147A EP 1374233 A1 EP1374233 A1 EP 1374233A1
Authority
EP
European Patent Office
Prior art keywords
ylidene
light
alkyl
optionally
optical data
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP02735147A
Other languages
German (de)
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
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lanxess Deutschland GmbH
Original Assignee
Bayer Chemicals AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE10115227A external-priority patent/DE10115227A1/en
Priority claimed from DE10117463A external-priority patent/DE10117463A1/en
Application filed by Bayer Chemicals AG filed Critical Bayer Chemicals AG
Publication of EP1374233A1 publication Critical patent/EP1374233A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic 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
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic 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
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/12—Benzo[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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic 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
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic 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
    • C07D455/04—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic 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
    • C07D491/02—Heterocyclic 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
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/06—Cobalt compounds
    • C07F15/065—Cobalt compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/045—Special non-pigmentary uses, e.g. catalyst, photosensitisers of phthalocyanine dyes or pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/085—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex substituting the central metal atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
    • C09B47/26—Amide radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent 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
    • C09K9/02—Organic tenebrescent materials
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording 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
    • G11B7/004—Recording, reproducing or erasing methods; Read, write or erase circuits therefor
    • G11B7/0045—Recording
    • G11B7/00455—Recording involving reflectivity, absorption or colour changes
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording 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
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording 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
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record 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
    • G11B7/244—Record 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
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording 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
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record 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
    • G11B7/244—Record 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
    • G11B7/246—Record 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
    • G11B7/247—Record 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 methine or polymethine dyes
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording 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
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record 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
    • G11B7/244—Record 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
    • G11B7/246—Record 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
    • G11B7/248—Record 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 porphines; azaporphines, e.g. phthalocyanines
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording 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
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record 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
    • G11B7/244—Record 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
    • G11B7/249—Record 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 organometallic compounds
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording 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
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record 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
    • G11B7/254—Record 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
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording 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
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/26—Apparatus or processes specially adapted for the manufacture of record carriers
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording 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
    • G11B7/007—Arrangement 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/21—Circular sheet or circular blank

Definitions

  • Optical data carrier containing a triazacyanine 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 contains a triazacyanine dye as a light-absorbing compound, and a process for its 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 spot size scales with the laser wavelength ⁇ / NA is the numerical aperture of the objective lens used.
  • the aim should be to use the smallest possible wavelength ⁇ . 390 nm are currently possible on the basis of semiconductor laser diodes.
  • the 780 nm wavelength 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 and 650 nm of the DVD-R lies at the foot of the short-wave flank of the absorption peak of the dye.
  • This concept is described in JP-A 02 557 335, JP-A 10 058 828, JP-A 06 336 086, JP-A 02 865 955, WO-A 09 917 284 and US-A 5 266 699 to the 450 nm range Working wavelength extended on the short-wave flank and the red and IR range on the long-wave flank of the absorption peak.
  • the recordable information layer made of light-absorbing organic substances must be as amorphous as possible
  • 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 diffuse by diffusion Form interfaces and thus adversely affect reflectivity.
  • a light-absorbing substance with too low heat resistance at the interface to a polymer carrier can diffuse in it and in turn adversely affect the reflectivity.
  • the vapor pressure of a light-absorbing substance is too high, it can subhm in 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 accordingly to provide suitable connections 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 writable optical data storage formats in one
  • the invention therefore relates to an optical data carrier, comprising a preferably transparent substrate, optionally already coated with one or more reflection layers, on the surface of which an information layer which can be written on with light, optionally one or more reflection layers and optionally a protective layer or a further substrate or a covering 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, characterized in that at least one triazacyanine dye is used as the light-absorbing compound.
  • 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 a temperature ⁇ 300 ° C., in particular ⁇ 200 ° C.
  • a change can be, for example, a decomposition or chemical change in the chromophoric center of the light-absorbing compound.
  • a triazacyanin of the formula I is preferred
  • X 1 and X 3 represent nitrogen or
  • X 2 and X 4 independently of one another represent O, S, CH or NR 3 ,
  • R, R and R independently of one another for C 6 -C 6 alkyl, C 3 - to C 6 alkenyl,
  • the rings A and B together with X ⁇ , X ⁇ or X ⁇ , ⁇ 4 and the C atom bonded between them each independently represent a five- or six-membered aromatic or quasi-aromatic heterocyclic ring which contain 1 to 4 heteroatoms and / or benzyl or naphthane fused and / or substituted by nonionic radicals, and An "stands for an anion,
  • nonionic radicals are C1 to C4 alkyl, C1 to C4 alkoxy, halogen, cyano, nitro, C1 to C4 alkoxycarbonyl, C1 to C4 alkylthio, C1 to C4 alkanoylamino, benzoylamino , Mono- or Di-C ⁇ - to C4-alkylamino in question.
  • Alkyl, alkoxy, aryl and heterocyclic radicals can optionally carry further radicals such as alkyl, halogen, nitro, cyano, CO-NH2, alkoxy, trialkylsilyl, trialkylsiloxy or phenyl, the 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, neighboring ones
  • Alkyl and / or alkoxy residues on aryl or heterocych residues can jointly form a three- or four-membered bridge and the heterocych residues can be fused to benzene and / or quaternized.
  • Ring A of the formula is particularly preferably
  • benzthiazol-2-yl benzoxazol-2-yl, benzimidazol-2-yl, thiazol-2-yl, isothiazol-3-yl, imidazol-2-yl, pyrazol-5-yl, l, 3,4-thiadiazole -2-yl, l, 2,4-thiadiazol-5-yl, 1,2,3-
  • said rings may each by Ci to C6 alkyl, Ci to C 6 alkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, C to C 6 alkoxycarbonyl, Ci to C 6 alkylthio, Ci to C ⁇ acylamino, C 6 to Cio aryl, C 6 - to Cio-aryloxy, C 6 - to C10- Arylcarbonylamino, mono- or di-C to C 6 -alkylamino, Nd- to C 6 -alkyl-N- C 6 - to Cio-arylamino, pyrrohdino, morpholino or piperazino, and
  • rings may each by Ci- to C 6 - alkyl, Ci to C 6 alkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, Ci to C6 - alkoxycarbonyl, CJ to C 6 alkylthio, C ⁇ - to C 6 acyla
  • the triazacyanines are those of the formula
  • R and R 2 independently of one another are Cp to C 6 alkyl, C 3 to C 6 alkenyl, C 5 to C 7 cycloalkyl or C 7 to C 6 aralkyl,
  • X 5 represents N or CR 6 .
  • X 6 represents N or CR 7 ,
  • R 4 to R 7 independently of one another are hydrogen, Cp to C alkyl, Ci to C 4 -
  • Ci 5 -aralkylamino N-Cp to C 4 -alkyl-NC 5 - to C ⁇ 7 -cyclo- alkylamino, N-Cp to C -alkyl-NC 6 - to Cio-arylamino, C 6 - to Ciö- Arylamino, Pyrrohdino, Piperidino, Piperazino or Morpholino stand or
  • C 4 alkoxy substituted Cp to Cio alkanoate optionally substituted by nitro, cyano, hydroxy, Cp to C 25 alkyl, perfluoro Cp to C alkyl, Cp to C alkoxycarbonyl or chlorine, benzene or naphthalene or biphenyl sulfonate , benzene or naphthalene or biphenyl disulfonate, optionally substituted by nitro, cyano, hydroxy, Cp to C alkyl, Cp to C 4 alkoxy, Cp to C 4 alkoxycarbonyl or chlorine, optionally by nitro, cyano, Cp to C 4- alkyl, Cp to C -alkoxy, Cp to C 4 -alkoxy- carbonyl, benzoyl, chlorobenzoyl or toluoyl substituted benzoate, the anion of naphthalenedicarboxylic acid, diphenyl ether disulfonate, the
  • Bromide, iodide, tetrafluoroborate, perchlorate, methanesulfonate, benzenesulfonate, toluenesulfonate, dodecylbenzenesulfonate, tetradecanesulfonate are preferred.
  • the triazacyanines used are those of the formula (IV)
  • R 1 and R 2 independently of one another are methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl, cyclohexyl, chloroethyl, cyanomethyl, cyanoethyl, hydroxyethyl, 2-hydroxypropyl, methoxyethyl, ethoxyethyl or a radical of the formula
  • X 5 represents N or CR 6 .
  • X 6 represents N or CR 7
  • R 4 and R 5 independently of one another are hydrogen, methyl, ethyl, methoxy, cyano, methoxycarbonyl, dimethylamino, diethylamino, dipropylamino, dibutylamino, N-methyl-N-cyanoethylamino, N-methyl-N-methoxyethylamino, N-methyl- N-hydroxyethylamino, bis (cyanoethyl) amino, bis (methoxyethyl) amino, bis (hydroxyethyl) amino, N-methyl-N-benzylamino, N-methyl-N-phenylamino, phenylamino, methoxyphenylamino, pyrrohdino, piperidino , N-methyl-, N-ethyl-, N-hydroxyethyl- or N-cyanoethylpiperazino or morpholino,
  • R 6 and R 7 independently of one another represent hydrogen, methyl, ethyl, methoxy or cyano or
  • the triazacyanines used are those of the formula (IV)
  • R 1 and R 2 are the same and represent methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl, cyclohexyl, chloroethyl, cyanomethyl, cyanoethyl, hydroxyethyl, 2-hydroxypropyl, methoxyethyl, ethoxyethyl or a radical of the formula
  • the triazacyanines used are those of the formula (IV)
  • R 1 and R 2 are the same and represent methyl, ethyl, propyl, butyl, pentyl, hexyl,
  • X 5 represents N
  • X 6 represents N
  • R 4 and R 5 are the same and represent dimethylamino, diethylamino, dipropylamino, dibutylamino, N-methyl-N-cyanoethylamino, N-methyl-N-methoxyethylamino, N-methyl-N-hydroxyethylamino, bis- (cyanoethyl) amino, Bis (methoxyethyl) amino, bis (hydroxyethyl) amino, N-methyl-N-benzylamino, N-methyl-N-phenylamino, phenylamino, methoxyphenylamino, pyrrohdino, piperidino, N-methyl, N-ethyl, N-hydroxyethyl- or N-cyanoethylpiperazino or morpholino, and
  • the triazacyanines used are those of the formula (IV)
  • R 1 and R 2 are the same and represent methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl, cyclohexyl, chloroethyl, cyanomethyl, cyanoethyl, hydroxyethyl, 2-hydroxypropyl, methoxyethyl, ethoxyethyl or a radical of the formula
  • X b CR 7 stands, R 4 for dimethylamino, diethylamino, dipropylamino, dibutylamino, N-
  • Methyl-N-hydroxyethylamino bis- (cyanoethyl) amino, bis- (methoxyethyl) amino, bis- (hydroxyethyl) amino, N-methyl-N-benzylamino, N- methyl-N-phenylamino, phenylamino, methoxyphenylamino,
  • those triazacyanine dyes are preferred whose absorption maximum ⁇ max2 is in the range 420 to 550 nm, the wavelength ⁇ / at which the extinction in the short-wave Flank of the absorption maximum of the wavelength ⁇ max is half the extinction value at ⁇ maX2 , and the wavelength ⁇ ⁇ 0 , at which the absorbance in the short-wave flank of the absorption maximum of the wavelength ⁇ max2
  • Tenths of the extinction value at ⁇ max2 is preferably not more than 50 nm apart.
  • Such a triazacyanine dye preferably does not have a shorter-wave maximum ⁇ max ⁇ up to a wavelength of 350 nm, particularly preferably up to 320 nm, very particularly preferably up to 290 nm.
  • Triazacyanin dyes with an absorption maximum ⁇ max2 of 410 to 530 nm are preferred.
  • Triazacyanine dyes with an absorption maximum ⁇ max2 of 420 to 510 nm are particularly preferred.
  • Triazacyanine dyes with an absorption maximum ⁇ max of 430 to 500 nm are very particularly preferred.
  • triazacyanine dyes ⁇ / 2 and ⁇ / ⁇ 0 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.
  • those triazacyanine dyes are preferred whose absorption maximum ⁇ maX 2 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 ⁇ max2 is half the extinction value at ⁇ maX2 , and the wavelength in 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 , preferably not further than
  • Such a triazacyanine dye preferably has no longer-wave maximum ⁇ max3 up to a wavelength of 750 nm, particularly preferably up to 800 nm, very particularly preferably up to 850 nm.
  • Triazacyanin dyes with an absorption maximum ⁇ max2 of are preferred
  • Triazacyanine dyes with an absorption maximum ⁇ maX 2 of 550 to 620 nm are particularly preferred.
  • Triazacyanine dyes with an absorption maximum ⁇ max2 of 580 to 610 nm are very particularly preferred.
  • triazacyanine dyes ⁇ / 2 and ⁇ ⁇ 0 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 triazcyanine dyes have a molar extinction coefficient ⁇ > 20,000 l / mol cm, preferably> 30,000 l / mol cm, particularly preferably> 40,000 l / mol cm, very particularly preferably> 60,000 l / mol cm.
  • the absorption spectra are measured, for example, in solution.
  • Triazacyanins of formula (I) are known, for. B. from EP-A 0 567 846.
  • the light-absorbing substances described guarantee a sufficiently high reflectivity (> 10%) of the optical data carrier in the blank state as well as 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 triazacyanine dyes according to the invention in particular guarantee a particularly high change in the refractive index during the transition from the unwritten to the described state.
  • the triazacyanine dyes are preferably applied to the optical data carrier by spin coating.
  • the triazacyanines can be mixed with one another or with other dyes with similar spectral properties.
  • 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 are used, among other things, to adjust the reflectivity and the heat balance. Depending on the laser wavelength, metals can be gold, silver, aluminum and others. Dielectric layers are, for example, silicon dioxide and silicon nitride.
  • Protective layers are, for example, photocurable lacquers, (pressure-sensitive) adhesive layers and protective films.
  • Preferred pressure-sensitive adhesive layers consist mainly of acrylic adhesives.
  • 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 one
  • Adhesive layer (5) Adhesive layer (5), a cover layer (6).
  • the structure of the optical data carrier can preferably:
  • a 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 a protective layer (4), optionally an adhesive layer (5), and a transparent one Cover layer (6) are applied.
  • a preferably 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 preferably transparent substrate (1) on the surface of which there is optionally a protective layer (2), at least one information layer (3) that can be written on with light, preferably laser light, optionally a protective layer (4), optionally an adhesive layer (5), and a trans Parente 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 (cf. FIG. 2): 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.

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Abstract

The invention relates to an optical data carrier that contains a preferably transparent substrate that is optionally already coated with one or more reflective layers, onto whose surface an information layer which can be written on with light, optionally one or more reflective layers and optionally a protective layer or a further substrate or a cover layer are applied. Said optical data carrier can be written on and read with blue, red or infrared light, preferably laser light, and the information layer comprises a light-absorbing compound and optionally a binder. The inventive data carrier is further characterized in that at least one triazacyanine dye is used as the light-absorbing compound.

Description

Optischer Datenträger enthaltend in der Informationsschicht einen Triazacyaninfarbstoff als lichtabsorbierende VerbindungOptical data carrier containing a triazacyanine dye in the information layer as a light-absorbing compound
Die Erfindung betrifft einen einmal beschreibbaren optischen Datenträger, der in derThe invention relates to a write-once optical data carrier, which in the
Informationsschicht als lichtabsorbierende Verbindung einen Triazacyaninfarbstoff enthält, sowie ein Verfahren zu ihrer Herstellung.Information layer contains a triazacyanine dye as a light-absorbing compound, and a process for its preparation.
Die einmal beschreibbaren optischen Datenträger unter Verwendung von speziellen lichtabsorbierenden Substanzen bzw. deren Mischungen eignen sich insbesondere für den Einsatz bei hochdichten beschreibbaren optischen Datenspeicher, die mit blauen Laserdioden insbesondere GaN oder SHG Laserdioden (360 - 460 nm) arbeiten und/oder für den Einsatz bei DVD-R bzw. CD-R Disks, die mit roten (635 - 660 nm) bzw. infraroten (780 - 830 nm) Laserdioden arbeiten, sowie die Applikation der oben genannten Farbstoffe auf ein Polymersubstrat, insbesondere Polycarbonat, durchThe 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
Spin-Coating oder Aufdampfen.Spin coating or vapor deposition.
Die einmal beschreibbare Compact Disk (CD-R, 780 nm) erlebt in letzter Zeit ein enormes Mengenwachstum und stellt das technisch etablierte System dar.The compact disk (CD-R, 780 nm), which can be written on once, has experienced enormous volume growth recently and represents the technically established system.
Aktuell wird die nächste Generation optischer Datenspeicher - die DVD - in den Markt eingeführt. Durch die Verwendung kürzerwelliger Laserstrahlung (635 bis 660 nm) und höherer numerischer Apertur NA kann die Speicherdichte erhöht werden. Das beschreibbare Format ist in diesem Falle die DVD-R.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.
Heute werden optische Datenspeicherformate, die blaue Laserdioden (Basis GaN, JP 08191171 oder Second Harmonie Generation SHG JP 09050629) (360 nm bis 460 nm) mit hoher Laserleistung benutzen, entwickelt. Beschreibbare optische Datenspeicher werden daher auch in dieser Generation Verwendung finden. Die er- reichbare Speicherdichte hängt von der Fokusierung des Laserspots in derToday, optical data storage formats using blue laser diodes (based on GaN, JP 08191171 or Second Harmonie Generation SHG JP 09050629) (360 nm to 460 nm) with high laser power are being developed. Writable optical data storage devices will therefore also be used in this generation. The storage density that can be achieved depends on the focus of the laser spot in the
Informationsebene ab. Die Spotgröße skaliert dabei mit der Laserwellenlänge λ / NA ist die numerische Apertur der verwendeten Objektivlinse. Zum Erhalt einer möglichst hohen Speicherdichte ist die Verwendung einer möglichst kleinen Wellenlänge λ anzustreben. Möglich sind auf Basis von Halbleiterlaserdioden derzeit 390 nm.Information level. The spot size scales with the laser wavelength λ / NA is the numerical aperture of the objective lens used. In order to obtain the highest possible storage density, the aim should be to use the smallest possible wavelength λ. 390 nm are currently possible on the basis of semiconductor laser diodes.
In der Patentliteratur werden auf Farbstoffe basierende beschreibbare optische Datenspeicher beschrieben, die gleichermaßen für CD-R und DVD-R Systeme geeignet sind (JP-A 11 043 481 und JP-A 10 181 206). Dabei wird für eine hohe Reflektivität und eine hohe Modulationshöhe des Auslesesignals, sowie für eine genügende Empfindlichkeit beim Einschreiben von der Tatsache Gebrauch gemacht, daß die IR-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). 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
Wellenlänge 780 nm der CD-R am Fuß der langwelligen Flanke des Absorptions- peaks des Farbstoffs liegt, die rote Wellenlänge 635 nm bzw. 650 nm der DVD-R am Fuß der kurzwelligen Flanke des Absorptionspeaks des Farbstoffs liegt. Diese Konzept wird in JP-A 02 557 335, JP-A 10 058 828 , JP-A 06 336 086, JP-A 02 865 955, WO-A 09 917 284 und US- A 5 266 699 auf den Bereich 450 nm Arbeitswellenlänge auf der kurzwelligen Flanke und den roten und IR Bereich auf der langwelligen Flanke des Absorptionspeaks ausgedehnt.The 780 nm wavelength 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 and 650 nm of the DVD-R lies at the foot of the short-wave flank of the absorption peak of the dye. This concept is described in JP-A 02 557 335, JP-A 10 058 828, JP-A 06 336 086, JP-A 02 865 955, WO-A 09 917 284 and US-A 5 266 699 to the 450 nm range Working wavelength extended on the short-wave flank and the red and IR range on the long-wave flank of the absorption peak.
Neben den oben genannten optischen Eigenschaften muss die beschreibbare Informa- tionsschicht aus lichtabsorbierenden organischen Substanzen eine möglichst amorpheIn addition to the optical properties mentioned above, the recordable information layer made of light-absorbing organic substances must be as amorphous as possible
Morphologie aufweisen, um das Rauschsignal beim Beschreiben oder Auslesen möglichst klein zu halten. Dazu ist es besonders bevorzugt, dass bei der Applikation der Substanzen durch Spin Coating aus einer Lösung, durch Aufdampfen und/oder Sublimation beim nachfolgenden Überschichten mit metallischen oder dielektrischen Schichten im Vakuum Kristallisation der lichtabsorbierenden Substanzen verhindert wird.Have morphology to keep the noise signal as small as possible when writing or reading. For this purpose, it is particularly preferred that when 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.
Die amorphe Schicht aus lichtabsorbierenden Substanzen sollte vorzugsweise eine hohe Wärmeformbeständigkeit besitzen, da ansonsten weitere Schichten aus organi- schem oder anorganischem Material, die per Sputtem oder Aufdampfen auf die lichtabsorbierende Informationsschicht aufgebracht werden via Diffusion unscharfe Grenzflächen bilden und damit die Reflektivität ungünstig beeinflussen. Darüber hinaus kann eine lichtabsorbierende Substanz mit zu niedriger Wärmeformbeständigkeit an der Grenzfläche zu einem Polymeren Träger in diesen diffundieren und wiederum die Reflektivität ungünstig beeinflussen.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 diffuse by diffusion Form interfaces and thus adversely affect reflectivity. In addition, a light-absorbing substance with too low heat resistance at the interface to a polymer carrier can diffuse in it and in turn adversely affect the reflectivity.
Ein zu hoher Dampfdruck einer lichtabsorbierenden Substanz kann beim oben erwähnten Sputtern bzw. Aufdampfen weiterer Schichten im Hochvakuum subhmieren und damit die gewünschte Schichtdicke vermindern. Dies führt wiederum zu einer negativen Beeinflussung der Reflektivität.If the vapor pressure of a light-absorbing substance is too high, it can subhm in 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.
Aufgabe der Erfindung ist demnach die Bereitstellung geeigneter Verbindungen, die die hohen Anforderungen (wie Lichtstabilität, günstiges Signal-Rausch-Verhältnis, schädigungsfreies Aufbringen auf das Substratmaterial, u.a.) für die Verwendung in der Informationsschicht in einem einmal beschreibbaren optischen Datenträger insbe- sondere für hochdichte beschreibbare optische Datenspeicher-Formate in einemThe object of the invention is accordingly to provide suitable connections 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 writable optical data storage formats in one
Laserwellenlängenbereich von 340 bis 680 nm erfüllen.Meet laser wavelength range from 340 to 680 nm.
Überraschender Weise wurde gefunden, dass lichtabsorbierende Verbindungen aus der Gruppe der Triazacyaninfarbstoffe das oben genannte Anforderungsprofil beson- ders gut erfüllen können.Surprisingly, it was found that light-absorbing compounds from the group of triazacyanine dyes can meet the above-mentioned requirement profile particularly well.
Die Erfindung betrifft daher einen optischen Datenträger, enthaltend ein vorzugsweise transparentes, gegebenenfalls schon mit einer oder mehreren Reflektions- schichten beschichtetes Substrat, auf dessen Oberfläche eine mit Licht beschreibbare Informationsschicht, gegebenenfalls eine oder mehrere Reflexionsschichten und gegebenenfalls eine Schutzschicht oder ein weiteres Substrat oder eine Abdeckschicht aufgebracht sind, der mit blauem oder rotem Licht, vorzugsweise Laserlicht, beschrieben und gelesen werden kann, wobei die Informationsschicht eine lichtabsorbierende Verbindung und gegebenenfalls ein Bindemittel enthält, dadurch gekenn- zeichnet, dass als lichtabsorbierende Verbindung wenigstens ein Triazacyaninfarbstoff verwendet wird. Die lichtabsorbierende Verbindung sollte vorzugsweise thermisch veränderbar sein. Vorzugsweise erfolgt die thermische Veränderung bei einer Temperatur <600°C, besonders bevorzugt bei einer Temperatur <400°C, ganz besonders bevorzugt bei einer Temperatur <300°C, insbesondere <200°C. Eine solche Veränderung kann beispielsweise eine Zersetzung oder chemische Veränderung des chromophoren Zentrums der lichtabsorbierenden Verbindung sein.The invention therefore relates to an optical data carrier, comprising a preferably transparent substrate, optionally already coated with one or more reflection layers, on the surface of which an information layer which can be written on with light, optionally one or more reflection layers and optionally a protective layer or a further substrate or a covering 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, characterized in that at least one triazacyanine dye is used as the light-absorbing compound. 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 a temperature <300 ° C., in particular <200 ° C. Such a change can be, for example, a decomposition or chemical change in the chromophoric center of the light-absorbing compound.
Bevorzugt ist ein Triazacyanin der Formel IA triazacyanin of the formula I is preferred
woπn embedded image in which
X1 und X3 für Stickstoff stehen oderX 1 and X 3 represent nitrogen or
X -1 - rR> l . u.„ndΛ v X3 - rR> 2 unabhängig voneinander für S stehen,X -1 - rR> l. u. "ndΛ v X3 - rR> 2 independently of one another stand for S,
X2 und X4 unabhängig voneinander für O, S, CH oder N-R3 stehen,X 2 and X 4 independently of one another represent O, S, CH or NR 3 ,
R , R und R unabhängig voneinander für Ci- bis Cι6-Alkyl, C3- bis C6-Alkenyl,R, R and R independently of one another for C 6 -C 6 alkyl, C 3 - to C 6 alkenyl,
C5- bis C7-Cycloalkyl oder C7- bis Cι6-Aralkyl stehen.C 5 - to C 7 cycloalkyl or C 7 - to -C 6 aralkyl.
Die Ringe A und B jeweils zusammen mit X^, X^ bzw. X^, χ4 und dem jeweils dazwischen gebundenen C-Atom unabhängig voneinander für einen fünf- oder sechs- gliedrigen aromatischen oder quasiaromatischen heterocyclischen Ring stehen, die 1 bis 4 Heteroatome enthalten und/oder benz- oder naphthanelliert und/oder durch nichtionische Reste substituiert sein können, und An" für ein Anion steht,The rings A and B together with X ^, X ^ or X ^, χ4 and the C atom bonded between them each independently represent a five- or six-membered aromatic or quasi-aromatic heterocyclic ring which contain 1 to 4 heteroatoms and / or benzyl or naphthane fused and / or substituted by nonionic radicals, and An "stands for an anion,
entspricht.equivalent.
Als nichtionische Reste kommen beispielsweise C\- bis C4-Alkyl, C\- bis C4- Alkoxy, Halogen, Cyano, Nitro, C\- bis C4-Alkoxycarbonyl, Cj- bis C4-Alkylthio, Cj- bis C4-Alkanoylamino, Benzoylamino, Mono- oder Di-C^- bis C4-Alkylamino in Frage.Examples of nonionic radicals are C1 to C4 alkyl, C1 to C4 alkoxy, halogen, cyano, nitro, C1 to C4 alkoxycarbonyl, C1 to C4 alkylthio, C1 to C4 alkanoylamino, benzoylamino , Mono- or Di-C ^ - to C4-alkylamino in question.
Alkyl-, Alkoxy-, Aryl- und heterocychschen Reste können gegebenenfalls weitere Reste wie Alkyl, Halogen, Nitro, Cyano, CO-NH2, Alkoxy, Trialkylsilyl, Trialkyl- siloxy oder Phenyl tragen, die Alkyl- und Alkoxyreste können geradkettig oder verzweigt sein, die Alkylreste können teil- oder perhalogeniert sein, die alkyl- und Alkoxyreste können ethoxyliert oder propoxyliert oder silyliert sein, benachbarteAlkyl, alkoxy, aryl and heterocyclic radicals can optionally carry further radicals such as alkyl, halogen, nitro, cyano, CO-NH2, alkoxy, trialkylsilyl, trialkylsiloxy or phenyl, the 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, neighboring ones
Alkyl und/oder Alkoxyreste an Aryl- oder heterocychschen Resten können gemeinsam eine drei- oder viergliedrige Brücke ausbilden und die heterocychschen Reste können benzanneliert und/oder quaterniert sein.Alkyl and / or alkoxy residues on aryl or heterocych residues can jointly form a three- or four-membered bridge and the heterocych residues can be fused to benzene and / or quaternized.
Besonders bevorzugt stehen der Ring A der FormelRing A of the formula is particularly preferably
für Benzthiazol-2-yl, Benzoxazol-2-yl, Benzimidazol-2-yl, Thiazol-2-yl, Isothiazol- 3-yl, Imidazol-2-yl, Pyrazol-5-yl, l,3,4-Thiadiazol-2-yl, l,2,4-Thiadiazol-5-yl, 1,2,3-for benzthiazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, thiazol-2-yl, isothiazol-3-yl, imidazol-2-yl, pyrazol-5-yl, l, 3,4-thiadiazole -2-yl, l, 2,4-thiadiazol-5-yl, 1,2,3-
Thiadiazol-5-yl, l,3,4-Triazol-2-yl, 2- oder 4-Pyridyl, 2- oder 4-Chinolyl steht, wobei die genannten Ringe jeweils durch Ci- bis C6-Alkyl, Ci- bis C6-Alkoxy, Fluor, Chlor, Brom, Iod, Cyano, Nitro, C bis C6-Alkoxycarbonyl, Ci- bis C6-Alkylthio, Ci- bis Cό-Acylamino, C6- bis Cio-Aryl, C6- bis Cio-Aryloxy, C6- bis C10- Arylcarbonylamino, Mono- oder Di-C bis C6-Alkylamino, N-d- bis C6-Alkyl-N- C6- bis Ciö-Arylamino, Pyrrohdino, Morpholino oder Piperazino substituiert sein können, undThiadiazol-5-yl, l, 3,4-triazol-2-yl, 2- or 4-pyridyl, 2- or 4-quinolyl, said rings may each by Ci to C6 alkyl, Ci to C 6 alkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, C to C 6 alkoxycarbonyl, Ci to C 6 alkylthio, Ci to C ό acylamino, C 6 to Cio aryl, C 6 - to Cio-aryloxy, C 6 - to C10- Arylcarbonylamino, mono- or di-C to C 6 -alkylamino, Nd- to C 6 -alkyl-N- C 6 - to Cio-arylamino, pyrrohdino, morpholino or piperazino, and
der Ring B der Formelthe ring B of the formula
für Benzthiazol-2-yliden, Benzoxazol-2-yliden, Benzimidazol-2-yliden, Thiazol-2- yliden, Isothiazol-3-yliden, Imidazol-2-yliden, Pyrazol-5-yliden, l,3,4-Thiadiazol-2- yliden, l,2,4-Thiadiazol-5-yliden, l,2,3-Thiadiazol-5-yliden, l,3,4-Triazol-2-yliden, Pyridin-2- oder 4-yliden, Chinolin-2- oder 4-yliden steht, wobei die genannten Ringe jeweils durch Ci- bis C6- Alkyl, Ci- bis C6-Alkoxy, Fluor, Chlor, Brom, lod, Cyano, Nitro, Ci- bis C6-Alkoxycarbonyl, Cj- bis C6-Alkylthio, C\- bis C6-Acylamino, C6- bis Cι0-Aryl, C6- bis Cio-Aryloxy, C6- bis Cio-Arylcarbonylamino, Mono- oder Di-for benzthiazol-2-ylidene, benzoxazol-2-ylidene, benzimidazol-2-ylidene, thiazol-2-ylidene, isothiazol-3-ylidene, imidazol-2-ylidene, pyrazol-5-ylidene, l, 3,4-thiadiazole -2-ylidene, l, 2,4-thiadiazol-5-ylidene, l, 2,3-thiadiazol-5-ylidene, l, 3,4-triazol-2-ylidene, pyridin-2- or 4-ylidene, quinoline-2- or 4-ylidene, said rings may each by Ci- to C 6 - alkyl, Ci to C 6 alkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, Ci to C6 - alkoxycarbonyl, CJ to C 6 alkylthio, C \ - to C 6 acylamino, C 6 - to Cι 0 aryl, C 6 - to Cio-aryloxy, C 6 - to Cio-arylcarbonylamino, mono- or di-
Cr bis C6-Alkylamino, N-Ci- bis C6-Alkyl-N-C6- bis Cio-Arylamino, Pyrrohdino, Morpholino oder Piperazino substituiert sein können.Cr to C 6 alkylamino, N-Ci to C 6 alkyl-NC 6 - to Cio-arylamino, pyrrohdino, morpholino or piperazino may be substituted.
In einer besonders bevorzugten Form handelt es sich bei den Triazacyaninen um solche der FormelIn a particularly preferred form, the triazacyanines are those of the formula
woπn R und R2 unabhängig voneinander für Cp bis Cι6-Alkyl, C3- bis C6-Alkenyl, C5- bis C7-Cycloalkyl oder C7- bis Cι6-Aralkyl stehen,embedded image in which R and R 2 independently of one another are Cp to C 6 alkyl, C 3 to C 6 alkenyl, C 5 to C 7 cycloalkyl or C 7 to C 6 aralkyl,
X5 für N oder C-R6 steht,X 5 represents N or CR 6 ,
X6 für N oder C-R7 steht,X 6 represents N or CR 7 ,
R4 bis R7 unabhängig voneinander für Wasserstoff, Cp bis C -Alkyl, Ci- bis C4-R 4 to R 7 independently of one another are hydrogen, Cp to C alkyl, Ci to C 4 -
Alkoxy, Ci- bis C4- Alkyl thio, Cyano, Cp bis C4-Alkoxycarbonyl, Nitro, Mono- oder Bis- Cp bis C -Alkylamino, N-Ci- bis C -Alkyl-N-Alkoxy, Ci to C 4 - alkyl thio, cyano, Cp to C 4 alkoxycarbonyl, nitro, mono- or bis- Cp to C alkylamino, N-Ci to C -alkyl-N-
C - bis Ci5-aralkylamino, N-Cp bis C4-Alkyl-N-C5- bis Cι7-cyclo- alkylamino, N-Cp bis C -Alkyl-N-C6- bis Cio-arylamino, C6- bis Ciö- Arylamino, Pyrrohdino, Piperidino, Piperazino oder Morpholino stehen oderC - to Ci 5 -aralkylamino, N-Cp to C 4 -alkyl-NC 5 - to Cι 7 -cyclo- alkylamino, N-Cp to C -alkyl-NC 6 - to Cio-arylamino, C 6 - to Ciö- Arylamino, Pyrrohdino, Piperidino, Piperazino or Morpholino stand or
R ;R und R ;R unabhängig voneinander eine -CH=CH-CH=CH-Brücke bilden, die durch Methyl, Chlor, Methoxy oder Cyano substituiert sein kann undR; R and R; R independently of one another form a -CH = CH-CH = CH bridge which can be substituted by methyl, chlorine, methoxy or cyano and
An" für ein Anion steht.An "stands for an anion.
Als Anionen An" kommen alle einwertigen Anionen oder ein Äquivalent eines mehrwertigen Anions in Frage. Vorzugsweise handelt es sich um farblose Anionen. Geeignete Anionen sind beispielsweise Chlorid, Bromid, Iodid, Tetrafluoroborat, Per- chlorat, Hexafluorosilicat, Hexafluorophosphat, Methosulfat, Ethosulfat, Ci- bis Cio- Alkansulfonat, Cp bis Cio-Perfluoralkansulfonat, ggf. durch Chlor, Hydroxy, Cp bisAnions An " are all monovalent anions or an equivalent of a polyvalent anion. They are preferably colorless anions. Suitable anions are, for example, chloride, bromide, iodide, tetrafluoroborate, perchlorate, hexafluorosilicate, hexafluorophosphate, methosulfate, ethosulfate, Ci - to Cio-alkanesulfonate, Cp to Cio-perfluoroalkanesulfonate, optionally by chlorine, hydroxy, Cp to
C4-Alkoxy substituiertes Cp bis Cio-Alkanoat, ggf. durch Nitro, Cyano, Hydroxy, Cp bis C25- Alkyl, Perfluor-Cp bis C - Alkyl, Cp bis C -Alkoxycarbonyl oder Chlor substituiertes Benzol- oder Naphthalin- oder Biphenylsulfonat, ggf. durch Nitro, Cyano, Hydroxy, Cp bis C - Alkyl, Cp bis C4- Alkoxy, Cp bis C4-Alkoxycarbonyl oder Chlor substituiertes Benzol- oder Naphthalin- oder Biphenyldisulfonat, ggf. durch Nitro, Cyano, Cp bis C4-Alkyl, Cp bis C -Alkoxy, Cp bis C4-Alkoxy- carbonyl, Benzoyl, Chlorbenzoyl oder Toluoyl substituiertes Benzoat, das Anion der Naphthalindicarbonsäure, Diphenyletherdisulfonat, Tetraphenylborat, Cyanotri- phenylborat, Tetra-Cp bis C2o-alkoxyborat, Tetraphenoxyborat, 7,8- oder 7,9-Di- carba-nido-undecaborat(l-) or (2-), die gegebenenfalls an den B- und/oder C-Atomen durch eine oder zwei Cp bis Cι2-Alkyl- oder Phenyl-Gruppen substituiert sind,C 4 alkoxy substituted Cp to Cio alkanoate, optionally substituted by nitro, cyano, hydroxy, Cp to C 25 alkyl, perfluoro Cp to C alkyl, Cp to C alkoxycarbonyl or chlorine, benzene or naphthalene or biphenyl sulfonate , benzene or naphthalene or biphenyl disulfonate, optionally substituted by nitro, cyano, hydroxy, Cp to C alkyl, Cp to C 4 alkoxy, Cp to C 4 alkoxycarbonyl or chlorine, optionally by nitro, cyano, Cp to C 4- alkyl, Cp to C -alkoxy, Cp to C 4 -alkoxy- carbonyl, benzoyl, chlorobenzoyl or toluoyl substituted benzoate, the anion of naphthalenedicarboxylic acid, diphenyl ether disulfonate, tetraphenyl borate, cyanotriphenyl borate, tetra-Cp to C 2 o-alkoxyborate, tetraphenoxyborate, 7,8- or 7,9-di-carba-nano-borate undecaborate (1-) or (2-), which are optionally substituted on the B and / or C atoms by one or two Cp to C 2 alkyl or phenyl groups,
Dodecahydro-dicarbadodecaborat(2-) oder B-Cp bis Cι2-Alkyl-C-phenyl-dodeca- hydro-dicarbadodecaborat( 1 -).Dodecahydro-dicarbadodecaborate (2-) or B-Cp to Cι 2 -alkyl-C-phenyl-dodeca- hydro-dicarbadodecaborate (1 -).
Bevorzugt sind Bromid, Iodid, Tetrafluoroborat, Perchlorat, Methansulfonat, Benzolsulfonat, Toluolsulfonat, Dodecylbenzolsulfonat, Tetradecansulfonat.Bromide, iodide, tetrafluoroborate, perchlorate, methanesulfonate, benzenesulfonate, toluenesulfonate, dodecylbenzenesulfonate, tetradecanesulfonate are preferred.
In einer ganz besonders bevorzugten Form handelt es sich bei den verwendeten Triazacyaninen um solche der Formel (IV),In a very particularly preferred form, the triazacyanines used are those of the formula (IV)
worinwherein
R1 und R2 unabhängig voneinander für Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl, Benzyl, Cyclohexyl, Chlorethyl, Cyanmethyl, Cyanethyl, Hydroxyethyl, 2-Hydroxypropyl, Methoxyethyl, Ethoxyethyl oder einen Rest der FormelR 1 and R 2 independently of one another are methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl, cyclohexyl, chloroethyl, cyanomethyl, cyanoethyl, hydroxyethyl, 2-hydroxypropyl, methoxyethyl, ethoxyethyl or a radical of the formula
stehen, stand,
X5 für N oder C-R6 steht,X 5 represents N or CR 6 ,
X6 für N oder C-R7 steht, R4 und R5 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, Methoxy, Cyano, Methoxycarbonyl, Dimethylamino, Diethylamino, Dipropyl- amino, Dibutylamino, N-Methyl-N-cyanethylamino, N-Methyl-N- methoxyethylamino, N-Methyl-N-hydroxyethylamino, Bis-(cyan- ethyl)amino, Bis-(methoxyethyl)amino, Bis-(hydroxyethyl)amino, N- Methyl-N-benzylamino, N-Methyl-N-phenylamino, Phenylamino, Methoxyphenylamino, Pyrrohdino, Piperidino, N-Methyl-, N-Ethyl-, N-Hydroxyethyl- oder N-Cyanethylpiperazino oder Morpholino stehen,X 6 represents N or CR 7 , R 4 and R 5 independently of one another are hydrogen, methyl, ethyl, methoxy, cyano, methoxycarbonyl, dimethylamino, diethylamino, dipropylamino, dibutylamino, N-methyl-N-cyanoethylamino, N-methyl-N-methoxyethylamino, N-methyl- N-hydroxyethylamino, bis (cyanoethyl) amino, bis (methoxyethyl) amino, bis (hydroxyethyl) amino, N-methyl-N-benzylamino, N-methyl-N-phenylamino, phenylamino, methoxyphenylamino, pyrrohdino, piperidino , N-methyl-, N-ethyl-, N-hydroxyethyl- or N-cyanoethylpiperazino or morpholino,
R6 und R7 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, Methoxy oder Cyano stehen oderR 6 and R 7 independently of one another represent hydrogen, methyl, ethyl, methoxy or cyano or
R4;R6 und R5;R7 unabhängig voneinander eine -CH=CH-CH=CH-Brücke bilden, die durch Methyl, Chlor, Methoxy oder Cyano substituiert sein kann undR 4 ; R 6 and R 5 ; R 7 independently form a -CH = CH-CH = CH bridge which can be substituted by methyl, chlorine, methoxy or cyano and
An" für ein Anion steht.An "stands for an anion.
In einer ebenfalls herausragend bevorzugten Form handelt es sich bei den verwendeten Triazacyaninen um solche der Formel (IV),In a form which is also exceptionally preferred, the triazacyanines used are those of the formula (IV)
woπnembedded image in which
R1 und R2 gleich sind und für Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl, Benzyl, Cyclohexyl, Chlorethyl, Cyanmethyl, Cyanethyl, Hydroxy- ethyl, 2-Hydroxypropyl, Methoxyethyl, Ethoxyethyl oder einen Rest der FormelR 1 and R 2 are the same and represent methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl, cyclohexyl, chloroethyl, cyanomethyl, cyanoethyl, hydroxyethyl, 2-hydroxypropyl, methoxyethyl, ethoxyethyl or a radical of the formula
stehen, stand,
C-R steht,C-R stands
X6 C-R7 steht,X 6 CR 7 stands,
R4;R6 und R5;R7 gleich sind und eine -CH=CH-CH=CH-Brücke bilden, die durch Methyl, Chlor, Methoxy oder Cyano substituiert sein kann undR 4 ; R 6 and R 5 ; R 7 are the same and form a -CH = CH-CH = CH bridge which can be substituted by methyl, chlorine, methoxy or cyano and
An" für ein Anion steht.An "stands for an anion.
In einer ebenfalls herausragend bevorzugten Form handelt es sich bei den verwendeten Triazacyaninen um solche der Formel (IV),In a form which is also exceptionally preferred, the triazacyanines used are those of the formula (IV)
woπnembedded image in which
R1 und R2 gleich sind und für Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl,R 1 and R 2 are the same and represent methyl, ethyl, propyl, butyl, pentyl, hexyl,
Benzyl, Cyclohexyl, Chlorethyl, Cyanmethyl, Cyanethyl, Hydroxy- ethyl, 2-Hydroxypropyl, Methoxyethyl, Ethoxyethyl oder einen Rest der FormelBenzyl, cyclohexyl, chloroethyl, cyanomethyl, cyanoethyl, hydroxyethyl, 2-hydroxypropyl, methoxyethyl, ethoxyethyl or a radical of the formula
stehen,stand,
X5 für N steht,X 5 represents N,
X6 für N steht, R4 und R5 gleich sind und für Dimethylamino, Diethylamino, Dipropylamino, Dibutylamino, N-Methyl-N-cyanethylamino, N-Methyl-N-methoxy- ethylamino, N-Methyl-N-hydroxyethylamino, Bis-(cyanethyl)amino, Bis-(methoxyethyl)amino, Bis-(hydroxyethyl)amino, N-Methyl-N- benzylamino, N-Methyl-N-phenylamino, Phenylamino, Methoxy- phenylamino, Pyrrohdino, Piperidino, N-Methyl-, N-Ethyl-, N-Hy- droxyethyl- oder N-Cyanethylpiperazino oder Morpholino stehen, undX 6 represents N, R 4 and R 5 are the same and represent dimethylamino, diethylamino, dipropylamino, dibutylamino, N-methyl-N-cyanoethylamino, N-methyl-N-methoxyethylamino, N-methyl-N-hydroxyethylamino, bis- (cyanoethyl) amino, Bis (methoxyethyl) amino, bis (hydroxyethyl) amino, N-methyl-N-benzylamino, N-methyl-N-phenylamino, phenylamino, methoxyphenylamino, pyrrohdino, piperidino, N-methyl, N-ethyl, N-hydroxyethyl- or N-cyanoethylpiperazino or morpholino, and
An" für ein Anion steht.An "stands for an anion.
In einer ebenfalls herausragend bevorzugten Form handelt es sich bei den verwendeten Triazacyaninen um solche der Formel (IV),In a form which is also exceptionally preferred, the triazacyanines used are those of the formula (IV)
worinwherein
R1 und R2 gleich sind und für Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl, Benzyl, Cyclohexyl, Chlorethyl, Cyanmethyl, Cyanethyl, Hydroxy- ethyl, 2-Hydroxypropyl, Methoxyethyl, Ethoxyethyl oder einen Rest der FormelR 1 and R 2 are the same and represent methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl, cyclohexyl, chloroethyl, cyanomethyl, cyanoethyl, hydroxyethyl, 2-hydroxypropyl, methoxyethyl, ethoxyethyl or a radical of the formula
stehen,stand,
X5 N steht,X 5 N stands
Xb C-R7 steht, R4 für Dimethylamino, Diethylamino, Dipropylamino, Dibutylamino, N-X b CR 7 stands, R 4 for dimethylamino, diethylamino, dipropylamino, dibutylamino, N-
Methyl-N-cyanethylamino, N-Methyl-N-methoxyethylamino, N-Methyl-N-cyanoethylamino, N-methyl-N-methoxyethylamino, N-
Methyl-N-hydroxyethylamino, Bis-(cyanethyl)amino, Bis-(methoxy- ethyl)amino, Bis-(hydroxyethyl)amino, N-Methyl-N-benzylamino, N- Methyl-N-phenylamino, Phenylamino, Methoxyphenylamino,Methyl-N-hydroxyethylamino, bis- (cyanoethyl) amino, bis- (methoxyethyl) amino, bis- (hydroxyethyl) amino, N-methyl-N-benzylamino, N- methyl-N-phenylamino, phenylamino, methoxyphenylamino,
Pyrrohdino, Piperidino, N-Methyl-, N-Ethyl-, N-Hydroxyethyl- oder N-Cyanethylpiperazino oder Morpholino steht,Pyrrohdino, piperidino, N-methyl-, N-ethyl-, N-hydroxyethyl- or N-cyanoethylpiperazino or morpholino,
R5;R7 eine -CH=CH-CH=CH-Brücke bildet, die durch Methyl, Chlor, Methoxy oder Cyano substituiert sein kann undR 5 ; R 7 forms a -CH = CH-CH = CH bridge, which can be substituted by methyl, chlorine, methoxy or cyano and
An" für ein Anion steht.An "stands for an anion.
Für einen erfindungsgemäßen einmal beschreibbaren optischen Datenträger, der mit dem Licht eines blauen Lasers beschrieben und gelesen wird, sind solche Triazacyaninfarbstoffe bevorzugt, deren Absorptionsmaximum λmax2 im Bereich 420 bis 550 nm liegt, wobei die Wellenlänge λι/ , bei der die Extinktion in der kurzwelligen Flanke des Absorptionsmaxirnums der Wellenlänge λmax die Hälfte des Extinktionswerts bei λmaX2 beträgt, und die Wellenlänge λι ι0, bei der die Extinktion in der kurzwelligen Flanke des Absorptionsmaximums der Wellenlänge λmax2 einFor a once writable optical data carrier according to the invention, which is written and read with the light of a blue laser, those triazacyanine dyes are preferred whose absorption maximum λ max2 is in the range 420 to 550 nm, the wavelength λι / at which the extinction in the short-wave Flank of the absorption maximum of the wavelength λ max is half the extinction value at λ maX2 , and the wavelength λι ι 0 , at which the absorbance in the short-wave flank of the absorption maximum of the wavelength λ max2
Zehntel des Extinktionswerts bei λmax2 beträgt, vorzugsweise jeweils nicht weiter als 50 nm auseinander liegen. Bevorzugt weist ein solcher Triazacyaninfarbstoff bis zu einer Wellenlänge von 350 nm, besonders bevorzugt bis zu 320 nm, ganz besonders bevorzugt bis zu 290 nm, kein kürzerwelliges Maximum λmaxι auf.Tenths of the extinction value at λ max2 is preferably not more than 50 nm apart. Such a triazacyanine dye preferably does not have a shorter-wave maximum λ max ι up to a wavelength of 350 nm, particularly preferably up to 320 nm, very particularly preferably up to 290 nm.
Bevorzugt sind Triazacyaninfarbstoffe mit einem Absorptionsmaximum λmax2 von 410 bis 530 nm.Triazacyanin dyes with an absorption maximum λ max2 of 410 to 530 nm are preferred.
Besonders bevorzugt sind Triazacyaninfarbstoffe mit einem Absoφtionsmaximum λmax2 von 420 bis 510 nm. Ganz besonders bevorzugt sind Triazacyaninfarbstoffe mit einem Absoφtionsmaximum λmax von 430 bis 500 nm.Triazacyanine dyes with an absorption maximum λ max2 of 420 to 510 nm are particularly preferred. Triazacyanine dyes with an absorption maximum λ max of 430 to 500 nm are very particularly preferred.
Bevorzugt liegen bei diesen Triazacyaninfarbstoffen λι/2 und λι/ι0, so wie sie oben definiert sind, nicht weiter als 40 nm, besonders bevorzugt nicht weiter als 30 nm, ganz besonders bevorzugt nicht weiter als 20 nm auseinander.These triazacyanine dyes λι / 2 and λι / ι 0 , as defined above, 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.
Für einen erfindungsgemäßen einmal beschreibbaren optischen Datenträger, der mit dem Licht eines roten Lasers beschrieben und gelesen wird, sind solche Triazacyaninfarbstoffe bevorzugt, deren Absoφtionsmaximum λmaX2 im Bereich 500 bis 650 nm liegt, wobei die Wellenlänge λι/2, bei der die Extinktion in der langwelligen Flanke des Absoφtionsmaximums der Wellenlänge λmax2 die Hälfte des Extinktionswerts bei λmaX2 beträgt, und die Wellenlänge bei der die Extinktion in der langwelligen Flanke des Absoφtionsmaximums der Wellenlänge λmax2 ein Zehntel des Extinktionswerts bei λmax2 beträgt, vorzugsweise jeweils nicht weiter alsFor a write-once optical data carrier according to the invention which is written and read with the light of a red laser, those triazacyanine dyes are preferred whose absorption maximum λ maX 2 is in the range from 500 to 650 nm, the wavelength λι / 2 at which the absorbance in the long-wave flank of the absorption maximum of the wavelength λ max2 is half the extinction value at λ maX2 , and the wavelength in which the extinction in the long-wave flank of the absorption maximum of the wavelength λ max2 is one-tenth of the extinction value at λ max2 , preferably not further than
50 nm auseinander liegen. Bevorzugt weist ein solcher Triazacyaninfarbstoff bis zu einer Wellenlänge von 750 nm, besonders bevorzugt bis zu 800 nm, ganz besonders bevorzugt bis zu 850 nm, kein längerwelliges Maximum λmax3 auf.50 nm apart. Such a triazacyanine dye preferably has no longer-wave maximum λ max3 up to a wavelength of 750 nm, particularly preferably up to 800 nm, very particularly preferably up to 850 nm.
Bevorzugt sind Triazacyaninfarbstoffe mit einem Absoφtionsmaximum λmax2 vonTriazacyanin dyes with an absorption maximum λ max2 of are preferred
530 bis 630 nm.530 to 630 nm.
Besonders bevorzugt sind Triazacyaninfarbstoffe mit einem Absoφtionsmaximum λmaX2 von 550 bis 620 nm.Triazacyanine dyes with an absorption maximum λ maX 2 of 550 to 620 nm are particularly preferred.
Ganz besonders bevorzugt sind Triazacyaninfarbstoffe mit einem Absoφtionsmaximum λmax2 von 580 bis 610 nm.Triazacyanine dyes with an absorption maximum λ max2 of 580 to 610 nm are very particularly preferred.
Bevorzugt liegen bei diesen Triazacyaninfarbstoffen λι/2 und λι ι0, so wie sie oben definiert sind, nicht weiter als 40 nm, besonders bevorzugt nicht weiter als 30 nm, ganz besonders bevorzugt nicht weiter als 20 nm auseinander. Die Triazcyaninfarbstoffe weisen beim Absoφtionsmaximum λmaX2 einen molaren Extinktionskoeffizienten ε > 20000 1/mol cm, bevorzugt > 30000 1/mol cm, besonders bevorzugt > 40000 1/mol cm, ganz besonders bevorzugt > 60000 1/mol cm auf.These triazacyanine dyes λι / 2 and λι ι 0 , as defined above, 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. At the absorption maximum λ maX2, the triazcyanine dyes have a molar extinction coefficient ε> 20,000 l / mol cm, preferably> 30,000 l / mol cm, particularly preferably> 40,000 l / mol cm, very particularly preferably> 60,000 l / mol cm.
Die Absoφtionsspektren werden beispielsweise in Lösung gemessen.The absorption spectra are measured, for example, in solution.
Triazacyanine der Formel (I) sind bekannt, z. B. aus EP-A 0 567 846.Triazacyanins of formula (I) are known, for. B. from EP-A 0 567 846.
Die beschriebenen lichtabsorbierenden Substanzen garantieren eine genügend hohe Reflektivität (> 10%) des optischen Datenträgers im unbeschriebenen Zustand sowie eine genügend hohe Absoφtion zur thermischen Degradation der Informationsschicht bei punktueller Beleuchtung mit fokussiertem Licht, wenn die Lichtwellen- länge im Bereich von 360 bis 460 nm und 600 bis 680 nm liegt. Der Kontrast zwischen beschriebenen und unbeschriebenen Stellen auf dem Datenträger wird durch die Reflektivitätsänderung der Amplitude als auch der Phase des einfallenden Lichts durch die nach der thermischen Degradation veränderten optischen Eigenschaften der Informationsschicht realisiert.The light-absorbing substances described guarantee a sufficiently high reflectivity (> 10%) of the optical data carrier in the blank state as well as 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.
Die erfindungsgemäßen Triazacyaninfarbstoffe garantieren insbesondere eine besonders hohe Änderung des Brechungsindex beim Übergang vom unbeschriebenen in den beschriebenen Zustand.The triazacyanine dyes according to the invention in particular guarantee a particularly high change in the refractive index during the transition from the unwritten to the described state.
Die Triazacyaninfarbstoffe werden auf den optischen Datenträger vorzugsweise durch Spin-coaten aufgebracht. Die Triazacyanine können untereinander oder aber mit anderen Farbstoffen mit ähnlichen spektralen Eigenschaften gemischt werden. Die Informationsschicht kann neben den Triazacyaninfarbstoffen Additive enthalten wie Bindemittel, Netzmittel, Stabilisatoren, Verdünner und Sensibilisatoren sowie weitere Bestandteile. Der optische Datenspeicher kann neben der Informationsschicht weitere Schichten wie Metallschichten, dielektrische Schichten sowie Schutzschichten tragen. Metalle und dielektrische Schichten dienen u. a. zur Einstellung der Reflektivität und des Wärmehaushalts. Metalle können je nach Laserwellenlänge Gold, Silber, Aluminium u.a. sein. Dielektrische Schichten sind beispielsweise Siliziumdioxid und Silicium- nitrid. Schutzschichten sind, beispielsweise photohärtbare, Lacke, (drucksensitive) Kleberschichten und Schutzfolien.The triazacyanine dyes are preferably applied to the optical data carrier by spin coating. The triazacyanines can be mixed with one another or with other dyes with similar spectral properties. In addition to the triazacyanine dyes, the information layer can contain additives such as binders, wetting agents, stabilizers, thinners and sensitizers and other constituents. In addition to the information layer, the optical data storage device can carry further layers such as metal layers, dielectric layers and protective layers. Metals and dielectric layers are used, among other things, to adjust the reflectivity and the heat balance. Depending on the laser wavelength, metals can be gold, silver, aluminum and others. Dielectric layers are, for example, silicon dioxide and silicon nitride. Protective layers are, for example, photocurable lacquers, (pressure-sensitive) adhesive layers and protective films.
Bevorzugte drucksensitive Kleberschichten bestehen hauptsächlich aus Acrylklebern. Nitto Denko DA-8320 oder DA-8310, in Patent JP-A 11-273147 offengelegt, können beispielsweise für diesen Zweck verwendet werden.Preferred pressure-sensitive adhesive layers consist mainly of acrylic adhesives. Nitto Denko DA-8320 or DA-8310, disclosed in patent JP-A 11-273147, for example, can be used for this purpose.
Der optische Datenträger weist beispielsweise folgenden Schichtaufbau auf (vgl. Fig. 1): ein transparentes Substrat (1), gegebenenfalls eine Schutzschicht (2), eine In- formationsschicht (3), gegebenenfalls eine Schutzschicht (4), gegebenenfalls eineThe 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 one
Kleberschicht (5), eine Abdeckschicht (6).Adhesive layer (5), a cover layer (6).
Vorzugsweise kann der Aufbau des optischen Datenträgers:The structure of the optical data carrier can preferably:
- ein vorzugsweise transparentes Substrat (1) enthalten, auf dessen Oberfläche mindestens eine mit Licht beschreibbare Informationsschicht (3), die mit Licht, vorzugsweise Laserlicht beschrieben werden kann, gegebenenfalls eine Schutzschicht (4), gegebenenfalls eine Kleberschicht (5), und eine transparente Abdeckschicht (6) aufgebracht sind.- Contain 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 a protective layer (4), optionally an adhesive layer (5), and a transparent one Cover layer (6) are applied.
ein vorzugsweise transparentes Substrat (1) enthalten, auf dessen Oberfläche eine Schutzschicht (2), mindestens eine mit Licht, vorzugsweise Laserlicht beschreibbare Informationsschicht (3), gegebenenfalls eine Kleberschicht (5), und eine transparente Abdeckschicht (6) aufgebracht sind. ein vorzugsweise transparentes Substrat (1) enthalten, auf dessen Oberfläche gegebenenfalls eine Schutzschicht (2), mindestens eine mit Licht, vorzugsweise Laserlicht beschreibbare Informationsschicht (3), gegebenenfalls eine Schutzschicht (4), gegebenenfalls eine Kleberschicht (5), und eine trans- parente Abdeckschicht (6) aufgebracht sind.contain a preferably 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. contain a preferably transparent substrate (1), on the surface of which there is optionally a protective layer (2), at least one information layer (3) that can be written on with light, preferably laser light, optionally a protective layer (4), optionally an adhesive layer (5), and a trans Parente cover layer (6) are applied.
ein vorzugsweise transparentes Substrat (1) enthalten, auf dessen Oberfläche mindestens eine mit Licht, vorzugsweise Laserlicht beschreibbare Informationsschicht (3), gegebenenfalls eine Kleberschicht (5), und eine transparente Abdeckschicht (6) aufgebracht sind.contain 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.
Alternativ weist der optische Datenträger beispielsweise folgenden Schichtaufbau auf (vgl. Fig. 2): ein vorzugsweise transparentes Substrat (11), eine Informationsschicht (12), gegebenenfalls eine Reflexionsschicht (13), gegebenenfalls eine Kleberschicht (14), ein weiteres vorzugsweise transparentes Substrat (15).Alternatively, the optical data carrier has, for example, the following layer structure (cf. FIG. 2): a preferably transparent substrate (11), an information layer (12), optionally a reflection layer (13), optionally an adhesive layer (14), another preferably transparent substrate (15).
Die Erfindung betrifft weiterhin mit blauem oder rotem Licht, insbesondere Laserlicht beschriebene erfindungsgemäße optische Datenträger. The invention further relates to optical data carriers according to the invention described with blue or red light, in particular laser light.
Die folgenden Beispiele verdeutlichen den Gegenstand der Erfindung:The following examples illustrate the subject matter of the invention:
BeispieleExamples
Beispiel 1example 1
a) 45 g 2-Aminobenzthiazol wurden in 500 ml Toluol bei 80°C während 30 min mit 41.6 g Dimethylsulfat versetzt. Nach 1 h bei 80°C wurde die Suspension abgekühlt, abgesaugt und mit Toluol gewaschen. Der Feststoff wurde in 300 ml Wasser gelöst. Durch Zugabe von konz. KOH-Lösung wurde der pH auf 9 angehoben. Nach 6 h Rühren bei Raumtemperatur wurde das ausgefallene Produkt abgesaugt, mit Wasser gewaschen und gertocknet. Man erhielt 42,9 g (87 % ά. Th.) farbloses Kristallisat der Formela) 45 g of 2-aminobenzothiazole were added in 500 ml of toluene at 80 ° C for 30 min with 41.6 g of dimethyl sulfate. After 1 h at 80 ° C the suspension was cooled, suction filtered and washed with toluene. The solid was dissolved in 300 ml of water. By adding conc. KOH solution, the pH was raised to 9. After stirring for 6 hours at room temperature, the precipitated product was filtered off with suction, washed with water and dried. 42.9 g (87% of th.) Of colorless crystals of the formula were obtained
b) 30 g 2-Aminobenzthiazol wurden in 400 ml Eisessig gelöst und bei 10°C mit 80 ml 85 gew.-%iger Phosphorsäure und 60 ml 48 gew.-%iger Schwefelsäure versetzt. Bei 5°C wurden 68 g Nitrosylschwefelsäure (40 gew.-%ig in Schwefelsäure) zugetropft. Nach 4 h bei 0-5 °C wurde der Nitritüberschuss mit Amidosulfonsäure zerstört.b) 30 g of 2-aminobenzothiazole were dissolved in 400 ml of glacial acetic acid and 80 ml of 85% strength by weight phosphoric acid and 60 ml of 48% strength by weight sulfuric acid were added at 10 ° C. 68 g of nitrosylsulfuric acid (40% by weight in sulfuric acid) were added dropwise at 5 ° C. After 4 h at 0-5 ° C, the excess nitrite was destroyed with sulfamic acid.
c) Die Diazotierung aus b) wurde zu einer Lösung von 32,8 g des Produkts aus a) in 240 ml Eisessig bei 10°C getropft, wobei der pH durch Zutropfen von 20 gew.-%iger Sodalösung auf 3 gehalten wurde. Schließlich wurde auf pH =c) The diazotization from b) was added dropwise to a solution of 32.8 g of the product from a) in 240 ml of glacial acetic acid at 10 ° C., the pH being kept at 3 by dropwise addition of 20% strength by weight sodium carbonate solution. Finally it was adjusted to pH =
3,5 gestellt und über Nacht bei Raumtemperatur gerührt. Das Produkt wurde abgesaugt, mit Wasser gewaschen. Es wurde in 300 ml Wasser angeschlagen, mit 20 gew.-%iger Sodalösung auf pH = 7,5 eingestellt, erneut abgesaugt, mit Wasser gewaschen und getrocknet. Man erhielt 29,7 g (46 % d. Th.) eines gelben Pulvers der Formel3.5 and stirred overnight at room temperature. The product was filtered off, washed with water. It was struck in 300 ml of water, adjusted to pH = 7.5 with 20% by weight sodium carbonate solution, suctioned off again, with Washed water and dried. 29.7 g (46% of theory) of a yellow powder of the formula were obtained
d) 8,8 g des Triazens aus c) wurden in 40 ml γ-Butyrolacton bei 80°C mit 4 ml Dimethylsulfat versetzt. Nach 6 h bei 80°C wurde abgekühlt, auf 500 ml Wasser ausgetragen und von Unlöslichem abfiltriert.d) 8.8 g of the triazene from c) were mixed with 40 ml of γ-butyrolactone at 80 ° C. with 4 ml of dimethyl sulfate. After 6 h at 80 ° C., the mixture was cooled, poured onto 500 ml of water and insoluble was filtered off.
e) Die Lösung aus d) wurde bei Raumtemperatur mit 6,6 g Natriumtetra- fluoroborat versetzt. Nach Rühren über Nacht wurde abgesaugt und mit Wasser gewaschen. Der orange Feststoff wurde nacheinander in 50 ml Methanol, 50 ml Essigester und 10 ml Wasser verrührt, jeweils abgesaugt und getrocknet. Man erhielt 2,4 g (28 % d. Th.) eines orangen Pulvers der Formele) The solution from d) was mixed with 6.6 g of sodium tetrafluoroborate at room temperature. After stirring overnight, the product was filtered off with suction and washed with water. The orange solid was stirred in succession in 50 ml of methanol, 50 ml of ethyl acetate and 10 ml of water, each filtered off with suction and dried. 2.4 g (28% of theory) of an orange powder of the formula were obtained
BF,BF,
Sch p. - 260-266 °C λmax (Methanol/Chloroform 1:1) = 489 nm ε = 33280 1/mol cm | 2 - λι ιo (kurzwellige Flanke) = 61 nm λj/2 - λi/iQ (langwellige Flanke) = 16 nm Löslichkeit: > 2% in TFP (2,2,3,3-Tetrafluoφropanol) glasartiger Film. Ebenfalls geeignete Triazacyaninfarbstoffe sind in der Tabelle zusammengestellt:Sch p. - 260-266 ° C λ max (methanol / chloroform 1: 1) = 489 nm ε = 33280 1 / mol cm | 2 - λι ιo (short-wave flank) = 61 nm λj / 2 - λi / iQ (long-wave flank) = 16 nm Solubility:> 2% in TFP (2,2,3,3-tetrafluoropropanol) glassy film. Suitable triazacyanine dyes are also listed in the table:
!) in Methanol, wenn nicht anders angegeben. !) in methanol, unless otherwise stated.
2) auf der kurzwelligen Flanke 2) on the short-wave flank
3) auf der langwelligen Flanke 3) on the long-wave flank

Claims

Patentansprücheclaims
1. Optischer Datenträger enthaltend ein vorzugsweise transparentes gegebenenfalls schon mit einer oder mehreren Reflektionsschichten beschichtetes Substrat, auf dessen Oberfläche eine mit Licht beschreibbare Informationsschicht, gegebenenfalls eine oder mehrere Reflexionsschichten und gegebenenfalls eine Schutzschicht oder ein weiteres Substrat oder eine Abdeckschicht aufgebracht sind, der mit blauem oder rotem Licht, vorzugsweise Laserlicht, beschrieben und gelesen werden kann, wobei die Informations- Schicht eine lichtabsorbierende Verbindung und gegebenenfalls eine Bindemittel enthält, dadurch gekennzeichnet, dass als lichtabsorbierende Verbindung und gegebenenfalls ein Bindemittel enthält, dadurch gekennzeichnet, dass als lichtabsorbierende Verbindung wenigstens ein Triazacyaninfarbstoff verwendet wird.1. Optical data carrier containing a preferably transparent substrate, possibly already coated with one or more reflection layers, on the surface of which an information layer which can be written on with light, optionally one or more reflection layers and optionally a protective layer or a further substrate or a covering layer, which are coated with blue or red light, preferably laser light, can be described and read, the information layer containing a light-absorbing compound and optionally a binder, characterized in that the light-absorbing compound and optionally containing a binder, characterized in that at least one triazacyanine dye is used as the light-absorbing compound becomes.
Optischer Datenträger gemäß Anspruch 1, dadurch gekennzeichnet, dass das Triazacyanin der FormelOptical data carrier according to claim 1, characterized in that the triazacyanin of the formula
worinwherein
X1 und X3 für Stickstoff stehen oderX 1 and X 3 represent nitrogen or
X'-R1 und X3-R2 unabhängig voneinander für S stehen,X'-R 1 and X 3 -R 2 are independently S,
X2 und X4 unabhängig voneinander für O, S, CH oder N-R3 stehen, R , R und R unabhängig voneinander für Cp bis Cι6- Alkyl, C3- bis C6- Alkenyl, C5- bis C -Cycloalkyl oder C7- bis C16-Aralkyl stehen,X 2 and X 4 independently of one another represent O, S, CH or NR 3 , R, R and R independently of one another are Cp to C 6 alkyl, C 3 to C 6 alkenyl, C 5 to C cycloalkyl or C 7 to C 16 aralkyl,
die Ringe A und B jeweils zusammen mit χ , X^ bzw. X^, χ4 Und den jeweils dazwischen gebundenen C-Atomen unabhängig voneinander für einen fünf- oder sechsgliedrigen aromatischen oder quasiaromatischen heterocychschen Ring stehen, die 1 bis 4 Heteroatome enthalten und/oder benz- oder naphthanelliert und/oder durch nichtionische Reste substituiert sein können, undthe rings A and B each, together with χ, X ^ and X ^, χ4 U nd bound between each C-atoms independently a five or six membered aromatic or quasi-aromatic heterocychschen ring which contain 1 to 4 heteroatoms and / or benzylated or naphthanellated and / or substituted by nonionic radicals, and
An" für ein Anion steht,An "stands for an anion,
entspricht.equivalent.
3. Optischer Datenträger gemäß der Anspruch 2, dadurch gekennzeichnet, dass3. Optical data carrier according to claim 2, characterized in that
der Ring A der Formelthe ring A of the formula
für Benzthiazol-2-yl, Benzoxazol-2-yl, Benzimidazol-2-yl, Thiazol-2-yl, Iso- thiazol-3-yl, Imidazol-2-yl, Pyrazol-5-yl, l,3,4-Thiadiazol-2-yl, 1,2,4-Thia- diazol-5-yl, l,2,3-Thiadiazol-5-yl, l,3,4-Triazol-2-yl, 2- oder 4-Pyridyl, 2- oder 4-Chinolyl steht, wobei die genannten Ringe jeweils durch Cp bis C6-for benzthiazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, thiazol-2-yl, isothiazol-3-yl, imidazol-2-yl, pyrazol-5-yl, l, 3.4 -Thiadiazol-2-yl, 1,2,4-thiazad-5-yl, l, 2,3-thiadiazol-5-yl, l, 3,4-triazol-2-yl, 2- or 4- Pyridyl, 2- or 4-quinolyl, where the rings mentioned in each case by Cp to C 6 -
Alkyl, Cp bis C6-Alkoxy, Fluor, Chlor, Brom, lod, Cyano, Nitro, Cp bis C6- Alkoxycarbonyl, Cp bis C6- Alkyl thio, Cp bis C6-Acylamino, C6- bis Cio- Aryl, C6- bis Cio-Aryloxy, C6- bis Cio-Arylcarbonylamino, Mono- oder Di- Cp bis C6-Alkylamino, N-Cp bis C6-Alkyl-N-C6- bis Cι0-Arylamino, Pyrrohdino, Moφholino oder Piperazino substituiert sein können, undAlkyl, Cp to C 6 alkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, Cp to C 6 alkoxycarbonyl, Cp to C 6 alkyl thio, Cp to C 6 acylamino, C 6 to Cio aryl , C 6 - to Cio-aryloxy, C 6 - to Cio-arylcarbonylamino, mono- or di- Cp to C 6 alkylamino, N-Cp to C 6 alkyl-NC 6 - to Cι 0 arylamino, Pyrrohdino, Moφholino or piperazino may be substituted, and
der Ring B der Formelthe ring B of the formula
_C>_C>
BB
(III)(III)
für Benzthiazol-2-yliden, Benzoxazol-2-yliden, Benzimidazol-2-yliden, Thia- zol-2-yliden, Isothiazol-3-yliden, Imidazol-2-yliden, Pyrazol-5-yliden, 1,3,4- Thiadiazol-2-yliden, l,2,4-Thiadiazol-5-yliden, l,2,3-Thiadiazol-5-yliden, l,3,4-Triazol-2-yliden, Pyridin-2- oder 4-yliden, Chinolin-2- oder 4-yliden steht, wobei die genannten Ringe jeweils durch Cp bis C6- Alkyl, Cp bis C6- Alkoxy, Fluor, Chlor, Brom, lod, Cyano, Nitro, Cp bis C6-Alkoxycarbonyl, Cp bis C6-Alkylthio, Cp bis Cό-Acylamino, C6- bis Cio-Aryl, C6- bis Cι0- Aryloxy, C6- bis Cio-Arylcarbonylamino, Mono- oder Di-Cp bis C6-for benzothiazol-2-ylidene, benzoxazol-2-ylidene, benzimidazol-2-ylidene, thiazol-2-ylidene, isothiazol-3-ylidene, imidazol-2-ylidene, pyrazol-5-ylidene, 1,3,4 Thiadiazol-2-ylidene, l, 2,4-thiadiazol-5-ylidene, l, 2,3-thiadiazol-5-ylidene, l, 3,4-triazol-2-ylidene, pyridin-2- or 4- ylidene, quinolin-2- or 4-ylidene, the rings mentioned each having Cp to C 6 alkyl, Cp to C 6 alkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, Cp to C 6 alkoxycarbonyl , Cp to C 6 -alkylthio, Cp to Cό-acylamino, C 6 - to Cio-aryl, C 6 - to Cι 0 - aryloxy, C 6 - to Cio-arylcarbonylamino, mono- or di-Cp to C 6 -
Alkylamino, N-Cp bis C6-Alkyl-N-C6- bis Cio-Arylamino, Pyrrohdino, Moφholino oder Piperazino substituiert sein können.Alkylamino, N-Cp to C 6 -alkyl-NC 6 - to Cio-arylamino, pyrrohdino, Moφholino or piperazino can be substituted.
4. Optischer Datenträger gemäß einem oder mehreren der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass das Triazacyanin der Formel entspricht4. Optical data carrier according to one or more of claims 1 to 3, characterized in that the triazacyanin corresponds to the formula
woπn R1 und R2 unabhängig voneinander für Cp bis Cι6-Alkyl, C3- bis C6- Alkenyl, C5- bis C7-Cycloalkyl oder C7- bis d6-Aralkyl stehen,embedded image in which R 1 and R 2 independently of one another are Cp to C 6 alkyl, C 3 to C 6 alkenyl, C 5 to C 7 cycloalkyl or C 7 to d 6 aralkyl,
X3 für N oder C-R6 steht,X 3 represents N or CR 6 ,
X6 für N oder C-R7 steht,X 6 represents N or CR 7 ,
R4 bis R7 unabhängig voneinander für Wasserstoff, Cp bis C4-Alkyl, Cp bis C4- Alkoxy, Cyano, Cp bis C4-Alkoxycarbonyl, Nitro,R 4 to R 7 independently of one another are hydrogen, Cp to C 4 alkyl, Cp to C 4 alkoxy, cyano, Cp to C 4 alkoxycarbonyl, nitro,
Mono- oder Bis- Cp bis C4-Alkylamino, N-Cp bis C4-Alkyl- N-C7- bis C15-aralkylamino, N-Cp bis C4-Alkyl-N-C5- bis Ct7- cycloalkylamino, N-Cp bis C4-Alkyl-N-C6- bis Cio-arylamino, C6- bis do-Arylamino, Pyrrohdino, Piperidino oder Mor- pholino stehen oderMono- or bis-Cp to C 4 -alkylamino, N-Cp to C 4 -alkyl-NC 7 - to C 15 -aralkylamino, N-Cp to C 4 -alkyl-NC 5 - to C t7 - cycloalkylamino, N- Cp to C 4 alkyl-NC 6 - to Cio-arylamino, C 6 - to do-Arylamino, Pyrrohdino, Piperidino or Morpholino stand or
R4; R6 und R5; R7 unabhängig voneinander eine -CH=CH-CH=CH-Brücke bilden, die durch Methyl, Chlor, Methoxy oder Cyano substituiert sein kann undR 4 ; R 6 and R 5 ; R 7 independently form a -CH = CH-CH = CH bridge which can be substituted by methyl, chlorine, methoxy or cyano and
An" für ein Anion steht.An "stands for an anion.
5. Verwendung von Triazacyaninen in der Informationsschicht von einmal beschreibbaren optischen Datenträgem, wobei die Triazacyanine ein Absoφtionsmaximum λmax2 im Bereich von 420 bis 650 nm besitzen.5. Use of triazacyanins in the information layer of write-once optical data carriers, the triazacyanins having an absorption maximum λ max2 in the range from 420 to 650 nm.
6. Verwendung von Triazcyaninen in der Informationsschicht von einmal beschreibbaren optischen Datenträgem, wobei die Datenträger mit einem blauen Laserlicht beschrieben und gelesen werden. 6. Use of triazcyanines in the information layer of write-once optical data carriers, the data carriers being written on and read with a blue laser light.
7. Verfahren zur Herstellung der optischen Datenträger gemäß Anspruch 1, das dadurch gekennzeichnet ist, dass man ein vorzugsweise transparentes, gegebenenfalls mit einer Reflexionsschicht schon bechichtetes Substrat mit den Triazacyaninen gegebenenfalls in kombination mit geeigneten Bindern und Additiven und gegebenenfalls geeigneten Lösungsmitteln beschichtet und gegebenenfalls mit einer Relexionsschicht, weiteren Zwischenschichten und gegbenenfalls einer Schutzschicht oder einem weiteren Substrat oder einer Abdeckschicht versieht.7. The method for producing the optical data carrier according to claim 1, which is characterized in that a preferably transparent substrate, optionally already coated with a reflection layer, is coated with the triazacyanines, optionally in combination with suitable binders and additives and optionally suitable solvents, and optionally with a Relief layer, further intermediate layers and optionally a protective layer or another substrate or a cover layer.
8. Mit blauem oder rotem, insbesondere blauem Licht, insbesondere blauem8. With blue or red, especially blue light, especially blue light
Laserlicht, beschriebene optische Datenträger nach Anspruch 1. Laser light, described optical data carrier according to claim 1.
EP02735147A 2001-03-28 2002-03-20 Optical data carrier that contains a triazacyanine dye as the light-absorbing compound in the information layer g Withdrawn EP1374233A1 (en)

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DE10117463A DE10117463A1 (en) 2001-04-06 2001-04-06 Optical data medium for information recording, has cover layer and adhesive layer having preset total thickness, and recorded and readout with focussing objective lens setup having preset numerical aperture
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US6641889B2 (en) 2003-11-04
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JP2004524195A (en) 2004-08-12
CN1513176A (en) 2004-07-14

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