EP1323160A1 - Support de donnees optique comprenant dans la couche d'informations un colorant a base de phtalocyanine en tant que compose absorbant la lumiere - Google Patents

Support de donnees optique comprenant dans la couche d'informations un colorant a base de phtalocyanine en tant que compose absorbant la lumiere

Info

Publication number
EP1323160A1
EP1323160A1 EP01976217A EP01976217A EP1323160A1 EP 1323160 A1 EP1323160 A1 EP 1323160A1 EP 01976217 A EP01976217 A EP 01976217A EP 01976217 A EP01976217 A EP 01976217A EP 1323160 A1 EP1323160 A1 EP 1323160A1
Authority
EP
European Patent Office
Prior art keywords
optical data
data carrier
alkyl
formula
optionally
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Withdrawn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
EP01976217A
Other languages
German (de)
English (en)
Inventor
Horst Berneth
Karl-Friedrich Bruder
Wilfried Haese
Karin HASSENRÜCK
Serguei Kostromine
Peter Landenberger
Thomas Sommermann
Josef-Walter Stawitz
Rainer Hagen
Rafael Oser
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 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/de
Priority claimed from DE10124585A external-priority patent/DE10124585A1/de
Priority claimed from DE2001140165 external-priority patent/DE10140165A1/de
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1323160A1 publication Critical patent/EP1323160A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • 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

Definitions

  • Optical data carrier containing a phthalocyanine dye as a light-absorbing compound in the information layer
  • the invention relates to a write-once optical data carrier which can be used in the
  • Information layer as a light-absorbing compound contains at least one phthalocyanine dye, and a method for its preparation.
  • the write-once optical data carriers using special light-absorbing substances or mixtures thereof 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 - was recently launched.
  • the storage density can be increased by using shorter-wave laser radiation (635 to 660 nm) and a higher numerical aperture NA.
  • the write-once format is the DVD-R.
  • the patent literature describes dye-based writable optical data memories which are equally suitable for CD-R and DVD-R systems (JP-A 11 043 481 and JP-A 10 181 206).
  • JP-A 11 043 481 and JP-A 10 181 206 For a high reflectivity and a high modulation level of the readout signal, as well as for a sufficient sensitivity when writing, use is made of the fact that the IR wavelength 780 nm of the CD-R lies at the foot of the long-wave flank of the absorption peak of the dye.
  • the red wavelength 635 nm or 650 nm of the DVD-R lies at the foot of the short-wave flank of the absorption peak of the dye (cf. EP-A 519 395 and WO-A 00/09522).
  • the writable information layer made of light-absorbing organic substances must be as amo ⁇ he 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 blurred by diffusion Form interfaces and thus adversely affect reflectivity.
  • a light-absorbing substance with too low heat resistance at the interface to a polymeric carrier can diffuse in the latter and in turn adversely affect the reflectivity.
  • An excessively high vapor pressure of a light-absorbing substance can sublimate the above-mentioned sputtering or vapor deposition of further layers in a high vacuum and thus reduce the desired layer thickness. This in turn leads to a negative influence on the reflectivity.
  • the object of the invention is accordingly to provide suitable compounds which meet the high requirements (such as light stability, favorable signal-to-noise ratio, damage-free application to the substrate material, etc.) for use in the information layer in a write-once optical data carrier, in particular for high-density recordable optical media data storage
  • Phthalocyanines show an intense absorption in the for
  • Laser important wave range 360 - 460 nm the so-called B or Soret band.
  • the present invention therefore relates to an optical data carrier, comprising a — preferably transparent, 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 cover layer is applied, which can be written and read with blue light, preferably laser light, particularly preferably light at 360-460 nm, in particular 380-420 nm, very particularly preferably at 390-410 nm, the information layer being a light-absorbing compound and optionally on Contains binders, characterized in that at least one phthalocyanine is used as the light-absorbing compound.
  • a compound of the formula (I) is used as the phthalocyanine
  • Pc represents a phthalocyanine
  • radicals R 3 to R 6 correspond to substituents of the phthalocyanine ring, in which
  • X 1 and X 2 independently of one another for halogen such as F, Cl, Br, I, hydroxy,
  • R 3 , R 4 , R 5 and R 6 independently of one another for halogen such as F, Cl, Br, I, cyano, nitro, alkyl, aryl, alkylamino, dialkylamino, alkoxy, alkylthio, aryloxy, arylthio, SO 3 H, CO 2 R 9 , CONRiR 2 , NH-COR 7 or a radical of the formula - (B) m -D, in which
  • B is a bridge member from the group direct bond, CH2, CO, CH (alkyl),
  • metallocenyl radical or metallocenylcarbonyl radical titanium, manganese, iron, ruthenium or osmium being suitable as the metal center
  • Z 1 and Z 2 independently of one another represent NR'R ", OR” or SR ",
  • Y 1 stands for NR *, O or S
  • Y 2 stands for NR '
  • n 1 to 10
  • R 'and R independently of one another represent hydrogen, alkyl, cycloalkyl, aryl or hetaryl, or a direct bond or a bridge to one of the C-
  • w, x, y and z are independently 0 to 4 and w + x + y + z ⁇ 16,
  • R 1 and R 2 independently of one another for hydrogen, alkyl, hydroxyalkyl, aryl or R 1 and R 2 together with the N atom to which they are attached form a heterocyclic 5-, 6- or 7-membered ring, optionally under Participation of further heteroatoms, in particular from the group O, N and S, where NR J R 2 , in particular represent pyrrolidino, piperidino or Mo ⁇ holino,
  • R 7 to R 16 independently of one another represent alkyl, aryl, hetaryl or hydrogen, in particular represent alkyl, aryl or hetaryl,
  • Ci to C 20 alkylCOO " formate, oxalate, lactate, glycolate, citrate, CH 3 OSO 3 " , NH 2 SO 3 " , CH 3 SO 3 ⁇ , V ⁇ SO 4 2 " or 1/3 PO 4 3" stands.
  • M represents a radical of the formula (Ic), in particular with Co (III) as the metal atom
  • alkyl, alkoxy, aryl and heterocyclic radicals can optionally further radicals such as alkyl, halogen, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, nitro, cyano, CO-NH, alkoxy, alkoxycarbonyl, Mo ⁇ holino, piperidino, pyrrolidino , Pyrrolidono, trialkylsilyl, trialkylsiloxy or phenyl.
  • the alkyl and alkoxy radicals can be saturated, unsaturated, straight-chain or branched, the alkyl radicals can be partially or perhalogenated, the alkyl and alkoxy radicals can be ethoxylated or propoxylated or silylated. Adjacent alkyl and / or
  • Alkoxy radicals on aryl or heterocyclic radicals can together form a three- or four-membered bridge.
  • Preferred compounds of the formula (I) are those in which the following applies to the radicals R 1 to R 16 , R ', R "and the ligands or substituents X and X:
  • alkyl preferably denote Ci-Ci ⁇ -alkyl, in particular CrC 6 alkyl, which are optionally substituted by halogen, such as chlorine, bromine, fluorine, hydroxy, cyano and / or C 1 -C 6 alkoxy;
  • alkoxy are preferably C 1 -C 6 alkoxy, in particular dC 6 alkoxy, which are optionally substituted by halogen, such as chlorine, bromine, fluorine, hydroxy, cyano and / or dC 6 alkyl;
  • cycloalkyl are preferably C 4 -C 8 cycloalkyl, in particular C5 to C 6 cycloalkyl, which are optionally substituted by halogen, such as chlorine, bromine or fluorine, hydroxy, cyano and / or C 1 -C 6 alkyl are.
  • alkenyl preferably denote C 6 -O 8 alkenyl, which are optionally substituted by halogen, such as chlorine, bromine or fluorine, hydroxy, cyano and / or d-C0-alkyl, in particular alkenyl means allyl,
  • heterocyclic radicals with 5- to 7-membered rings, which preferably contain heteroatoms from the group N, S and / or O and are optionally fused with aromatic rings or optionally carry further substituents, for example halogen, hydroxy , Cyano and / or alkyl, with particular preference being given to: pyridyl, furyl, thienyl, oxazolyl, thiazolyl, imidazolyl, quinolyl, benzoxazolyl, benzthiazolyl and benzimidazolyl,
  • aryl is preferably C 6 -C ⁇ 0 aryl, in particular phenyl or naphthyl, optionally substituted by halogen, such as F, Cl, hydroxy, C ⁇ -C 6 - alkyl, C ⁇ -C 6 -alkoxy, NO 2 and or CN are substituted.
  • R 3 , R 4 , R 5 and R 6 independently of one another for chlorine, fluorine, bromine, iodine, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert. Butyl, pentyl, tert. Amyl, hydroxyethyl, 3-dimethylaminopropyl, 3-diethylaminopropyl,
  • Mi stands for a Mn or Fe cation
  • w, x, y and z are independently 0 to 4 and w + x + y + z ⁇ 12,
  • NR R for ammo, methylamino, ethylammo, propylamino, isopropylammo, butylamino, isobutylamino, tert. Butylamino, pentylamino, tert.
  • R 7 to R 16 independently of one another for hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, ter. -Butyl, pentyl, tert-amyl, phenyl, p-tert-butyl-phenyl, p-methoxyphenyl, isopropylphenyl, p-trifluoromethylphenyl, cyanophenyl, naphthyl, 4-pyridinyl, 2-pyridinyl, 2-quinolinyl, 2 -Pyrrolyl or 2-
  • the alkyl, alkoxy, aryl and heterocyclic radicals optionally further radicals such as alkyl, halogen, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, nitro, cyano, CO-NH 2 , alkoxy, alkoxycarbonyl, Mo ⁇ holino, piperidino, pyrrolidino , Pyrrolidono, trialkylsilyl, trialkylsiloxy or phenyl, the alkyl and / or alkoxy radicals can be saturated, unsaturated, straight-chain or branched, the alkyl radicals can be partially or perhalogenated, the alkyl and / or alkoxy radicals can be ethoxylated or propoxylated or silylated , adjacent alkyl and / or alkoxy radicals on aryl or heterocyclic radicals can jointly form a three- or four-membered bridge.
  • Redox systems in the context of this application include in particular those described in Angew. Chem. 1978, p. 927 and the redox systems described in Topics of Current Chemistry, Vol. 92, p. 1 (1980).
  • P-Phenylenediamines P-Phenylenediamines, phenothiazines, dihydrophenazines, bipyridinum salts (Viologene), quinodimethanes are preferred.
  • phthalocyanines of the formula (I) are used wherein
  • M stands for a trivalent, single axially substituted metal atom of the formula (Ia), the metal Me being selected from the group Al, Ga, Ti, In, Fe and Mn or
  • M represents a tetravalent, doubly axially substituted metal atom of the formula (Ib), the metal Me being selected from the group Si, Ge, Sn, Zr, Cr, Ti, Co and V.
  • X 1 and X 2 are halogen, in particular chlorine, aryloxy, in particular phenoxy or alkoxy, in particular methoxy.
  • R 3 - R 6 are in particular halogen, -CC 6 - alkyl or -CC 8 alkoxy.
  • Phthalocyanines of the formula I are very particularly preferred, where M is a radical of the formula (Ia) or (Ib) and w, x, y and z are each 0 and X 1 and / or X 2 are each halogen.
  • phthalocyanines used according to the invention can be prepared by known methods, for example:
  • the light-absorbing compound should preferably be thermally changeable.
  • the thermal change preferably takes place at a temperature ⁇ 600 ° C.
  • Such a change can be, for example, a decomposition or chemical change in the chromophoric center of the light-absorbing compound.
  • the light-absorbing substances described guarantee a sufficiently high reflectivity of the optical data carrier in the unwritten state and a sufficiently high absorption for the thermal degradation of the information layer in the case of selective illumination with focused blue light, in particular laser light, preferably with a light wavelength in the range from 360 to 460 nm.
  • the contrast between the described 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.
  • optical data carrier can preferably be written and read with laser light with a wavelength of 360-460 nm.
  • the coating with the phthalocyanines is preferably carried out by spin coating, sputtering or vacuum evaporation.
  • Vacuum evaporation or sputtering means in particular the phthalocyanines which are insoluble in organic or aqueous media, preferably those of the formula (I) where w, x, y and z are each 0 and
  • the phthalocyanines which are soluble in organic or aqueous media are particularly suitable for application by spin coats.
  • the phthalocyanines 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 serve u. a. to adjust the reflectivity and the heat balance. Depending on the laser wavelength, metals can be gold, silver, aluminum, alloys, etc. his.
  • Dielectric layers are, for example, silicon dioxide and silicon nitride.
  • Protective layers are, for example photocurable,
  • the structure of the optical data carrier can be:
  • the invention further relates to optical data carriers according to the invention described with blue light, in particular laser light, particularly preferably laser light with a wavelength of 360-460 nm.
  • the dye monochloro aluminum phthalocyanine (AlClPc) was evaporated in a high vacuum (pressure p »2 « 10 "5 mbar) from a resistively heated molybdenum boat at a rate of approx. 5 Als onto a pregrooved polycarbonate substrate.
  • the layer thickness was about 70 nm.
  • the pregrooved polycarbonate substrate was injection-molded as a disc. The diameter of the disc was 120 mm and its thickness was 0.6 mm.
  • the groove structure embossed in the injection molding process had a track spacing of about 1 ⁇ m, the groove depth The width of the half-width of the groove was about 150 nm and about 260 nm, respectively.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Optical Recording Or Reproduction (AREA)
  • Manufacturing Optical Record Carriers (AREA)

Abstract

La présente invention concerne un support de données optique comprenant un substrat de préférence transparent, éventuellement déjà revêtu avec une ou plusieurs couches de réflexion. Une couche d'informations, inscriptible avec de la lumière, éventuellement une ou plusieurs couches de réflexion et éventuellement une couche de protection ou un autre substrat ou une couche de couverture sont appliquées à la surface dudit substrat. Ce support de données optique peut être inscrit et lu avec de la lumière bleue, de préférence de la lumière laser. La couche d'informations comprend un composé absorbant la lumière et éventuellement un liant. Ce support de données optique est caractérisé en ce qu'au moins un colorant à base de phtalocyanine est utilisé en tant que composé absorbant la lumière.
EP01976217A 2000-09-21 2001-09-12 Support de donnees optique comprenant dans la couche d'informations un colorant a base de phtalocyanine en tant que compose absorbant la lumiere Withdrawn EP1323160A1 (fr)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
DE10046771 2000-09-21
DE10046771 2000-09-21
DE10115227 2001-03-28
DE10115227A DE10115227A1 (de) 2001-03-28 2001-03-28 Optischer Datenträger enthaltend in der Informationsschicht eine lichtabsorbierende Verbindung mit mehreren chromophoren Zentren
DE10124585A DE10124585A1 (de) 2000-09-21 2001-05-21 Optische Datenspeicher enthaltend ein Co-Phthalocyanin-Komplex in der mit Licht beschreibbaren Informationsschicht
DE10124585 2001-05-21
DE10140165 2001-08-22
DE2001140165 DE10140165A1 (de) 2001-08-22 2001-08-22 Optischer Datenträger enthaltend in der Informationsschicht einen Phthalocyaninfarbstoff als lichtabsorbierende Verbindung
PCT/EP2001/010515 WO2002025648A1 (fr) 2000-09-21 2001-09-12 Support de donnees optique comprenant dans la couche d'informations un colorant a base de phtalocyanine en tant que compose absorbant la lumiere

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JP (1) JP2004509785A (fr)
CN (1) CN1462435A (fr)
AU (1) AU2001295559A1 (fr)
CZ (1) CZ2003831A3 (fr)
PL (1) PL361400A1 (fr)
TW (1) TW583658B (fr)
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US20020076648A1 (en) 2002-06-20
AU2001295559A1 (en) 2002-04-02
CZ2003831A3 (cs) 2003-06-18
JP2004509785A (ja) 2004-04-02
PL361400A1 (en) 2004-10-04
CN1462435A (zh) 2003-12-17
TW583658B (en) 2004-04-11

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