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
  • C09B69/00—Dyes not provided for by a single group of this subclass
  • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic 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 cationic amino heterocyclic dye as a light-absorbing compound in the information layer
• the invention relates to a write-once optical data carrier which contains a cationic amino heterocyclic dye in the information layer as a light-absorbing compound, and to a process for its preparation and the application of the above-mentioned dyes to a polymer substrate, in particular polycarbonate, by spin coating or vapor deposition.
• 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.
• 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.
• JP-A 08 191 171 or Second Harmonie Generation SHG JP-A-09050629 (360 nm to 460 nm) with high laser power.
• 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 information level.
• the spot size scales with the laser wavelength ⁇ / NA.
• NA is the numerical aperture of the objective lens used.
• the use of the smallest possible wavelength ⁇ should be aimed for. 390 nm are currently possible on the basis of semiconductor laser diodes.
• 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 am
• the writable information layer made of light-absorbing organic substances must have a morphology which is as amorphous as possible in order to keep the noise signal as small as possible when writing or reading.
• the substances are applied by spin coating from a solution, by vapor deposition and / or sublimation, subsequent crystallization of the light-absorbing substances with metallic or dielectric layers in vacuum is prevented.
• the amorphous layer of light-absorbing substances should preferably have a high heat resistance, since otherwise further layers of organic or inorganic material, which are applied to the light-absorbing information layer by sputtering or vapor deposition, form blurred interfaces via diffusion and thus adversely affect the reflectivity.
• a light-absorbing substance with too low a heat resistance can diffuse at the interface to a polymeric carrier 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 therefore to provide suitable compounds that meet the high requirements (such as light stability, favorable signal-to-noise ratio, damage-free application to the substrate material, etc.) for use in the information layer in a write-once optical data carrier, in particular for high-density recordable optical media Meet data storage formats in a laser wavelength range from 340 to 830 nm.
• the invention therefore relates to an 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 are applied , which can be written and read with blue, red or infrared light, preferably laser light, the information layer containing a light-absorbing compound and optionally a binder, characterized in that at least one cationic amino heterocyclic 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 cationic amino heterocyclic dye of the formula I is preferred
• X 1 represents O or S
• X 2 represents CR 10 or N
• R 1 , R 2 , R 8 and R 9 independently of one another for hydrogen, d- to C 6 -alkyl, C 5 - bis
• C 7 cycloalkyl, C 6 - to C ⁇ 0 aryl or C 7 - to C ⁇ are 5 or aralkyl
• R 2 and NR 8 R 9 independently of one another represent pyrrolidino, morpholino, piperazino or piperidino,
• R 10 represents hydrogen, cyano, C to C6 alkyl, halogen, or C 6 - to C ⁇ is 0 aryl, Y for stands,
• Y rl b _ .; is “ ⁇ Yr3 independently of one another for N or C-R 18,
• n 0 or 1
• X 3 represents O or S
• X 4 represents CR 11 or N
• R represents hydrogen, C ⁇ - to C 6 -alkyl, halogen, hydroxy, C 6 - to do-aryl or NR 12 R 13 or
• R 3 and R 6 are an -O-, -CH 2 - or -C (CH 3 ) 2 bridge or a bridge of the formulas
• R 4, R 5, R 12 and R 13 independently represent hydrogen, Ci- to C ö alkyl, C 5 - to C ⁇ aralkyl - to C 7 -cycloalkyl, C 6 - to Cio-aryl or C 7 or
• NR 4 R 5 and NR 12 R 13 independently of one another represent pyrrolidmo, morpholino, piperazino or piperidino,
• R 11 represents hydrogen, cyano, C to C 6 alkyl, halogen or C 6 to o-aryl,
• X. 5 3 represents nitrogen or
• X 6 represents O, S, NR 19 , CR 20 or CR 20 R 21 ,
• Y ° represents N or CR 18 .
• R 7 and R 19 independently of one another are C ⁇ - to C 16 -alkyl, C 3 - to C 6 -alkenyl, C 5 - to C 7 -cycloalkyl or C 7 - to -CC 6 aralkyl, R 20 and R 21 independently of one another represent Cr to C alkyl or
• R 14 and R 15 are independently hydrogen, Cr to C 16 alkyl, - to C 7 - cycloalkyl, C 7 - to C 16 aralkyl, C 6 - to C 10 aryl or a heterocyclic
• NR 14 R 15 represent a five- or six-membered saturated ring which is attached via N and which may additionally contain an N or O and / or may be substituted by nonionic radicals,
• R 16 and R 16 independently of one another are hydrogen, Cr to C 6 alkyl, Cr to C 6 alkoxy or halogen or
• R 16 ; R 14 and / or R 16 ' ; R 15 form a two- or three-membered bridge which can contain an O or N and / or can be substituted by nonionic radicals
• R 17 for hydrogen, Cr to C 16 alkyl, Cr to C 16 alkoxy, halogen, cyano, Cr to C 4 alkoxycarbonyl, O-CO-R 22 , NR 23 -CO-R 22 , O-SO 2 - R 22 or NR 23 -SO 2 -R 22 is,
• R 22 for hydrogen, C to C 16 alkyl, C 4 to C 7 cycloalkyl, C 7 to C 16 aralkyl, Cr to Cie alkoxy, mono- or bis-Cr to C 6 alkylamino, C 6 to Cio-aryl, C 6 to Cio-aryloxy, C 6 to Cio-arylamino or a heterocyclic radical,
• R, 2 Z 3 i represents hydrogen or Q to C 4 alkyl
• a cationic amino heterocyclic dye of the formula I is also preferred
• X 1 represents O, S or Se
• X 2 represents CR ⁇ or N
• R 3 represents hydrogen, - to C 6 -alkyl, halogen, hydroxy, C 6 - to C 10 -aryl,
• NR 8 R 9 or -CH YA
• R 1 , R 2 , R 8 and R 9 independently of one another represent hydrogen, Cr to C 6 alkyl, C 5 to C 7 cycloalkyl, C 6 to C 10 aryl or C 7 to C 5 aralkyl or
• NR * R 2 and NR 8 R 9 independently of one another represent pyrrolidino, morpholmo, piperazino or piperidino,
• R 10 represents hydrogen, cyano, Cr to C 6 alkyl, halogen or C 6 to Cio aryl,
• Y 1 to Y 3 independently of one another represent N or CR 18 ,
• n 0 or 1
• X 3 represents O, S or Se
• R 6 represents hydrogen, Cr to C 6 alkyl, halogen, hydroxy, C 6 to Cio-aryl or NR 12 R 13 or
• R and R are a -O-, -CH 2 - or -C (CH 3 ) 2 bridge or a bridge of the formulas
• R 4 , R 5 , R 12 and R 13 independently of one another represent hydrogen, Cr to C 6 alkyl, C 5 to C 7 cycloalkyl, C 6 to Cio aryl or C 7 to C 5 aralkyl or
• NR 4 R 5 and NR 12 R 13 independently of one another represent pyrrolidmo, morpholino, piperazino or piperidino,
• R, ⁇ represents hydrogen, cyano, Cr to C 6 alkyl, halogen or C 6 to Cio aryl,
• X 5 represents nitrogen or X s -R 'stands for S
• X 6 represents O, S, NR 19 , CR 20 or CR 20 R 21 ,
• Y ° represents N or CR 18 .
• R 7 and R 19 independently of one another represent Cr to C 6 alkyl, C to C 6 alkenyl, C 5 to C 7 cycloalkyl or C to C 6 aralkyl,
• R> 20. and R, 21 independently of one another represent Cr to C 4 alkyl or
• B together with X 5 , X 6 and the C atom bonded in between represents a five- or six-membered aromatic or quasi-aromatic or partially hydrogenated heterocyclic ring which contain 1 to 4 heteroatoms and / or benzylated or naphthanellated and / or substituted by nonionic radicals can be,
• R 14 and R 15 independently of one another are hydrogen, Cr to C 6 alkyl, C 4 to C 7 cycloalkyl, C 7 to C 6 aralkyl, C 6 to Cio aryl or a heterocyclic radical or
• NR 14 R 15 represent a five- or six-membered saturated ring which is attached via N and which may additionally contain an N or O and / or may be substituted by nonionic radicals, R 16 and R 16 ' independently of one another represent hydrogen, Cr to Ci ⁇ -alkyl, Cr to C i 6 - alkoxy or halogen or
• R 16 ; R 1 and / or R 16 ; R 15 form a two- or three-membered bridge which can contain an O or N and / or can be substituted by nonionic radicals,
• R 17 for hydrogen, Cr to C 6 alkyl, Cr to C 6 alkoxy, halogen, cyano, Cr to C 4 alkoxycarbonyl, O-CO-R 22 , NR 23 -CO-R 22 , O-SO 2 - R 22 or
• R 22 for hydrogen, d to C 6 alkyl, C 4 to C 7 cycloalkyl, C 7 to C 6 aralkyl, Cr to C 6 alkoxy, mono- or bis-Cr to C 6 alkylamino, C 6 - to Cio-aryl, C 6 - to Cio-aryloxy, C 6 - to Cio-arylamino or a heterocyclic radical,
• R 23 represents hydrogen or C to C 4 alkyl
• nonionic radicals are Cr to C - alkyl, Cr to C 4 alkoxy, halogen, cyano, nitro, Cr to C alkoxycarbonyl, Cr to C alkylthio, Cr to C -
• Alkanoylamino benzoylamino, mono- or di-Cr to C 4 -alkylamino in question.
• Alkyl, alkoxy, aryl and heterocyclic radicals can optionally carry further radicals such as alkyl, halogen, nitro, cyano, CO-NH 2 , alkoxy, trialkylsilyl, trialkylsiloxy or phenyl, 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, adjacent alkyl and / or alkoxy radicals on aryl or heterocyclic radicals can jointly form a three- or four-membered bridge and the heterocyclic radicals can be fused to benzene and / or quaternized.
• Ring B is preferably of the formula
• Ring B of the formula is also preferably
• naimim rings each by Cj to C 6 alkyl, Cr to C 6 alkoxy, fluorine,
• the cationic amino heterocyclic dyes used are those of the formula (VI)
• X and X independently of one another represent O or S,
• X 4 represents CR 11 or N
• R 3 represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 8 R 9 ,
• R 6 represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 12 R 13 or
• R 1 , R 2 , R 4 , R 5 , R 8 , R 9 , R 12 and R 13 independently of one another for hydrogen, methyl
• R 10 and R 1! independently of one another represents hydrogen, cyano, methyl, ethyl, propyl, butyl, phenyl, tolyl, methoxyphenyl or xylyl,
• n 0 or 1
• the cationic amino heterocyclic dyes used are those of the formula (VI) embedded image in which
• X 1 , X 3 and X 3 independently of one another represent O, S or Se,
• X 2 represents CR 10 or N
• X 4 and X 4 * independently of one another represent CR 11 or N,
• R 3 represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 8 R 9 ,
• R 6 and R 6 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 12 R 13 or
• R 1 , R 2 , R 4 , R 4 * , R 5 , R 5 * , R 8 , R 9 , R 12 , R 13 , R 14 * and R 15 * independently of one another for hydrogen, methyl, ethyl, propyl, Butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclopentyl, cyclohexyl, phenyl, tolyl, methoxyphenyl,
• Xylyl, benzyl, phenethyl or phenylpropyl are or
• R 2 , NR 4 R 5 , NR 4 * R 5 * , NR 8 R 9 , NR 12 R 13 and NR 14 * R 15 * independently of one another represent pyrrolidino, morpholino, piperazino, N-methylpiperazino or piperidino, R 10 and R n independently of one another represent hydrogen, cyano, methyl, ethyl, propyl, butyl, phenyl, tolyl, methoxyphenyl or xylyl,
• R 16 * and R 16 '* independently of one another represent hydrogen, methyl, methoxy or chlorine or
• R 10 ; R 14 and / or R .1 1 6 0 '* 7 ⁇ R- 1 1 5 3 can form a - (CH 2 ) 2 - or - (CH 2 ) 3 bridge,
• n 0 or 1
• X 1 are very particularly preferred; X 3 , X 2 ; X 4 , R 1 ; R 4 , R 2 ; R 5 and R 3 ; R 6 in pairs the same.
• the dyes of the formula (VI) are also very particularly preferred,
• X 1 and X 3 are the same and stand for O or S,
• X 2 and X 4 are the same and stand for CH or N,
• R 3 and R 6 are the same and represent hydrogen, methyl, 2-propyl, tert-butyl, chlorine,
• R 1 , R 2 , R 4 , R 5 , R 8 and R 9 represent hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, phenyl or benzyl, the radicals of the groups R 1 ; R 4 ; R 8 and R 2 ; R 5 ; R 9 are the same in each case, or
• NR R 2 , NO. 4 R 5 and NR 8 R 9 are the same and stand for pyrrolidmo, morpholino or piperidino *
• the cationic aminoheterocyclic dyes used are those of the formula (VII)
• X 1 represents O or S
• X 2 represents CR 10 or N
• R 3 represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 8 R 9 ,
• R 1 , R 2 , R 8 and R 9 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclopentyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, xylyl, benzyl, phenethyl or phenylpropyl or
• ⁇ 2 and NR 8 R 9 independently of one another represent pyrrolidino, morpholino, piperazino, N-methylpiperazino or piperidino,
• R 10 represents hydrogen, cyano, methyl, ethyl, propyl, butyl, phenyl, tolyl, methoxyphenyl or xylyl,
• X 5 is N
• benzthiazol-2-ylidene 1,3-thiazol-2-ylidene, benzoxazol-2-ylidene, benzimidazol-2-ylidene, 3-H - Indol-2-ylidene, dihydropyridin-2- or -4-ylidene, dihydroquinolin-2- or -4-ylidene, 1,3-thiazolin-2-ylidene, 1,3-oxazolin-2-ylidene, imidazolin-2 -ylidene or pyrrolin-2-ylidene, or.
• R 7 represents methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, allyl, cyclopentyl, cyclohexyl, benzyl, phenethyl or phenylpropyl,
• n 0 or 1
• Y ° represents CH or N
• the cationic aminoheterocyclic dyes used are those of the formula (VII)
• X "" 1 X v3 independently of one another represent O, S or Se, X 2 represents CR 10 or N,
• X 4 represents CR ⁇ 11 or N
• R 3 represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 8 ⁇ rR> 9 y ,
• R, 6 ° represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 12 R 13 ,
• R 1 , R 2 , R 4 * , R 5 * , R 8 , R 9 , R 14 * and R 15 * independently of one another for hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclopentyl, cyclohexyl, Phenyl, tolyl, methoxyphenyl, xylyl, benzyl, phenethyl or phenylpropyl or
• NR ] R 2 , NR 4 * R 5 * , NR 8 R 9 and R 14 * R 15 * independently of one another represent pyrrolidino, morpholino, piperazino, N-methylpiperazino or piperidmo,
• R 10 and R n independently of one another represent hydrogen, cyano, methyl, ethyl, propyl, butyl, phenyl, tolyl, methoxyphenyl or xylyl,
• Formylamino, acetylamino, propionylamino, phenyl, tolyl, methoxyphenyl, Phenoxy, benzoylamino, dimethylamino, diethylamino, dipropylamino, N-methyl-N-phenylamino, pyrrolidino, morpholino or piperidino can be substituted,
• R 7 represents methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, allyl, cyclopentyl, cyclohexyl, benzyl, phenethyl or phenylpropyl,
• R 16 * and R 16 '* independently of one another represent hydrogen, methyl, methoxy or chlorine or
• R 16 * ; R 14 * and / or R 16 ' 7 R 15 * can form a - (CH 2 ) 2 - or - (CH 2 ) 3 bridge,
• n 0 or 1
• Y u CH or N
• the dyes of the formula (VII) are very particularly preferred
• X 1 represents O or S
• X 2 represents CH or N
• R 3 represents hydrogen, methyl, 2-propyl, tert-butyl, chlorine, phenyl or NR 8 R 9 ,
• R 1 , R 2 , R 8 and R 9 represent hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, phenyl or benzyl, the radicals R 1 ; R 8 and R 2 ; R 9 are the same in pairs, or
• NR ⁇ 2 and NR 8 R 9 are the same and represent pyrrolidino, morpholino or piperidmo,
• the cationic amino heterocyclic dyes used are those of the formula (VIII)
• X 1 represents O or S
• X 2 represents CR, ⁇ l o u or N
• R j represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 8 8 Rr, ° y
• R 1 , R 2 , R 8 and R 9 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclopentyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, xylyl, benzyl, phenethyl or phenylpropyl or lSö ⁇ R 2 and NR 8 R 9 independently of one another represent pyrrolidino, morpholino, piperazino, N-methylpiperazino or piperidmo,
• R 10 represents hydrogen, cyano, methyl, ethyl, propyl, butyl, phenyl, tolyl, methoxyphenyl or xylyl,
• R 14 and R 15 independently represent hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclopentyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, xylyl, benzyl, phenethyl, phenylpropyl, pyridyl or a radical of the formula
• NR 14 R 15 represents pyrrolidino, morpholino, piperazino, N-methylpiperazino or piperidino,
• R 16 and R 16 ' independently of one another represent hydrogen, methyl, ethyl, methoxy, ethoxy or chlorine or
• R 16 ; R 15 and / or R 16 ' ; R 14 form a - (CH 2 ) 2 - or - (CH 2 ) 3 bridge, which can be substituted by up to 3 methyl groups,
• R 17 For hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, cyano, methoxycarbonyl, ethoxycarbonyl, O-CO-R 22 , NR 23 -CO-R 22 , O-SO 2 -R 22 or NR 23 - SO 2 -R 22 stands,
• R 22 represents methyl, ethyl, trifluoromethyl, cyclopentyl, cyclohexyl, benzyl, methoxy, ethoxy, dimethylamino, diethylamino, methylamino, phenyl, phenoxy, anilino or pyridyl
• R, 23 represents hydrogen or methyl
• n 0 or 1
• the cationic amino heterocyclic dyes used are those of the formula (VIII)
• X 1 represents O, S or Se
• X represents CR 1 1 0 U or N
• R 3 represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 8 R 9 ,
• R 1 , R 2 , R 8 , R 9 , R 14 * and R 15 * independently of one another for hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclopentyl, Cyclohexyl, phenyl, tolyl, methoxyphenyl, xylyl, benzyl, phenethyl or phenylpropyl or
• NR R 2 , NR 8 R 9 and NR 14 * R 15 * independently of one another represent pyrrolidino, morpholino, piperazino, N-methylpiperazino or piperidino,
• R 10 represents hydrogen, cyano, methyl, ethyl, propyl, butyl, phenyl, tolyl, methoxyphenyl or xylyl,
• R 14 and R 15 independently of one another are hydrogen, methyl, ethyl, propyl, butyl,
• NR 14 R 15 represents pyrrolidino, morpholino, piperazino, N-methylpiperazino or piperidino,
• R 16 and R 16 ' independently of one another for hydrogen, methyl, ethyl, methoxy,
• R 16 ; R 15 and / or R 16 ' ; R 14 form a - (CH 2 ) 2 - or - (CH 2 ) 3 bridge which can be substituted by up to 3 methyl groups,
• R 17 for hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, cyano, methoxycarbonyl, Eth ⁇ xycarbonyl, O-CO-R 22 , NR 23 -CO-R 22 , O-SO 2 -R 22 or NR 23 -SO 2 -R 22 stands, R 22 represents methyl, ethyl, trifluoromethyl, cyclopentyl, cyclohexyl, benzyl, methoxy, ethoxy, dimethylamino, diethylamino, methylamino, phenyl, phenoxy, anilino or pyridyl,
• R 23 represents hydrogen or methyl
• R 16 * and R 16 '* independently of one another represent hydrogen, methyl, methoxy or chlorine or
• R 16 * ; R 14 * and / or R 16 ' 7 R 15 * can form a - (CH 2 ) 2 - or - (CH 2 ) 3 bridge,
• n 0 or 1
• the dyes of the formula (VIII) are very particularly preferred,
• X 1 represents O or S
• X 2 represents CH or N
• R 3 represents hydrogen, methyl, 2-propyl, tert-butyl, chlorine, phenyl or NR 8 R 9 ,
• R 1 , R 2 , R 8 and R 9 represent hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, phenyl or benzyl, the radicals R 1 ; R 8 and R 2 ; R 9 are the same in pairs, or
• NT ⁇ R 2 and NR 8 R 9 are the same and represent pyrrolidmo, morpholino or piperidino,
• R 14 and R 15 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, phenyl or benzyl or
• NR 14 R 15 represents pyrrolidino, morpholino or piperidino
• R 16 represents hydrogen, methyl or methoxy or
• R 16 ; R 15 form a - (C ⁇ 2 ) 2 -, - (CH 2 ) 3 - or -C (CH 3 ) 2 - (CH 2 ) 2 bridge,
• R 16 represents hydrogen
• R 17 represents hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, cyano, methoxycarbonyl, ethoxycarbonyl, acetoxy, acetamino, benzoylamino, methanesulfonylamino or trifluoromethanesulfonylamino,
• Y stands for CH or N
• Suitable anions An “are all monovalent anions or one equivalent of a polyvalent anion or polymeric in question. Preferably, there is are colorless anions. Suitable anions include, for example, chloride, bromide, iodide, tetrafluoroborate, perchlorate, hexafluorosilicate, hexafluorophosphate, methosulfate,
• Suitable anions are the anions of dyes, preferably dyes whose ⁇ max differs from the ⁇ maX 2 or ⁇ maX 3 of the dyes of the formula (I) by no more than 30 nm, preferably no more than 20 nm, very particularly preferably differs by no more than 10 nm.
• anionic dyes are oxonols, azo dyes, anthraquinone dyes or metal complex dyes such as. B. formazans or azo metal complex dyes.
• Bromide, iodide, tetrafluoroborate, perchlorate, hexafluorophosphate, methanesulfonate, trifluoroethanesulfonate, benzenesulfonate, toluenesulfonate, dodecylbenzenesulfonate, tetradecanesulfonate are preferred.
• Mixtures of the cationic amino heterocyclic dyes according to the invention can also be used for properties of the information layer.
• Mixtures with other, preferably cationic, dyes can also be used.
• Preferably used as mixed dyes are those whose ⁇ max differs from the ⁇ max2 or ⁇ max of the dyes of the formula (I) by no more than 30 nm, preferably no more than 20 nm, very particularly preferably no more than 10 nm.
• Examples include dyes from the classes of cyanines, streptocyanines, hemicyanines, diazahemicyanines, zero methines, enamine dyes, hydrazone dyes, di- or tri (het) arylmethane dyes, xanthene dyes, azine dyes (phenazines, oxazines, thiazines) or, for example, from the classes of azo dyes, anthraquinone dyes, neutrocyanines, porphyrins or
• Phthalocyanines Such dyes are known for example from H. Berneth,
• a write-once optical data carrier which is written and read with the light of a blue laser
• Wavelength ⁇ max2 is one tenth of the absorbance value at ⁇ max2 , preferably not more than 50 nm apart.
• a cationic amino heterocyclic dye preferably has 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.
• Such cationic aminoheterocyclic dyes with an absorption maximum ⁇ max2 of 410 to 530 nm are preferred.
• Cationic ammoheterocyclic dyes with an absorption maximum ⁇ max2 of 420 to 510 nm are particularly preferred.
• Cationic amino heterocyclic dyes with an absorption maximum ⁇ max2 of 430 to 500 nm are very particularly preferred.
• These cationic aminoheterocyclic dyes ⁇ j / 2 and ⁇ ⁇ o, as defined above, are preferably not more than 40 nm apart, particularly preferably not more than 30 nm apart, very particularly preferably not more than 20 nm apart.
• Range is 500 to 650 nm, the wavelength ⁇ / 2 , at which the absorbance in the long-wave flank of the absorption maximum of wavelength ⁇ max2 is half the absorbance value at ⁇ max , and the wavelength ⁇ ⁇ / ⁇ o, at which the Absorbance in the long-wave flank of the absorption maximum of wavelength ⁇ max2 is one tenth of the absorbance value at ⁇ max2 , preferably not more than 50 nm apart.
• Such a cationic aminoheterocyclic 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.
• Cationic amino heterocyclic dyes with an absorption maximum ⁇ max2 of 530 to 630 nm are preferred.
• Absorption maximum ⁇ max from 550 to 620 nm.
• These cationic ammoheterocyclic dyes ⁇ and ⁇ / ⁇ o, 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.
• a write-once optical data carrier which is written and read with the light of an infrared laser
• Wavelength ⁇ max3 is one tenth of the extinction value at ⁇ max3 , preferably not more than 50 nm apart.
• Cationic ammoheterocyclic dyes with an absorption maximum ⁇ max3 of 660 to 790 nm are preferred.
• Cationic aminoheterocyclic dyes with an absorption maximum ⁇ max3 of 670 to 760 nm are particularly preferred.
• Cationic aminoheterocyclic dyes with an absorption maximum ⁇ max3 of 680 to 740 nm are very particularly preferred.
• cationic ammoheterocyclic dyes ⁇ / 2 and ⁇ ⁇ o are preferably not more than 40 nm apart, particularly preferably not more than 30 nm apart, very particularly preferably not more than 20 nm apart.
• the cationic ammoheterocyclic dyes have a molar extinction coefficient ⁇ > 40,000 l / mol cm, preferably> 60,000 l / mol cm, particularly preferably> 80,000 l / mol cm, very particularly preferably> 100,000 l / mol cm.
• the absorption spectra are measured, for example, in solution.
• a method for determining such a dipole moment change ⁇ is described, for example, in F. Würthner et al., Angew. Chem. 1997, 109, 2933 and in the literature cited therein.
• a low solvatochromism methanol / methylene chloride
• Cationic aminoheterocyclic dyes and their solvatochromism are preferred
• ⁇ I ⁇ Met iencWo ⁇ d - ⁇ Methanoi
• Cationic amino heterocyclic dyes of the formula (I) are known in some cases, for example from Synthesis, 1973, 621; Angew. Chem. 2001, 113, 597; Dissertation R. Flaig, University of Halle, 1996, Angew. Chem. 2001, 113, 3097.
• the invention further provides cationic ammoheterocyclic dyes of the formula (VI), wherein
• X 1 and X 3 independently of one another represent O or S,
• X 2 represents CR 10 or N
• X 4 represents CR 11 or N
• R 3 represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 8 R 9 ,
• R 6 represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 12 R 13 or
• R 1 , R 2 , R 4 , R 5 , R 8 , R 9 , R 12 and R 13 independently of one another for hydrogen, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclopentyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, xylyl, Benzyl, phenethyl or phenylpropyl are or
• NR ⁇ 2 , NR 4 R 5 , NR 8 R 9 and NR 12 R 13 independently of one another represent pyrrolidino, piperazino, N-methylpiperazino or piperidino,
• Y 1 to Y 3 represent CH
• n 0 or 1
• X 1 are preferred; X 3 , X 2 ; X 4 , R 1 R 4 , R 2 ; R 5 and R 3 ; R 6 in pairs the same.
• the invention further provides cationic amino heterocyclic dyes of the formula (VII),
• X 1 represents O or S
• X 2 represents CR 10 or N
• R 3 represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 8 R 9 ,
• R 1 , R 2 , R 8 and R 9 independently of one another are hydrogen, methyl, ethyl, propyl,
• R 2 and NR 8 R 9 independently of one another represent pyrrolidino, morpholino, piperazino, N-methylpiperazino or piperidino,
• R 10 represents hydrogen, cyano, methyl, ethyl, propyl, butyl, phenyl, tolyl, methoxyphenyl or xylyl,
• R 7 represents methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, allyl, cyclopentyl, cyclohexyl, benzyl, phenethyl or phenylpropyl,
• Y 1 to Y 3 represent CH
• n 0 or 1
• the invention furthermore relates to cationic amino heterocyclic dyes of the formula (VIII),
• X 1 represents O or S
• X 2 represents CR 10 or N
• R 3 represents hydrogen, methyl, ethyl, propyl, butyl, chlorine, phenyl, tolyl, methoxyphenyl, xylyl or NR 8 R 9 ,
• R 1 , R 2 , R 8 and R 9 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclopentyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, xylyl, benzyl, phenethyl or phenylpropyl or
• NR L R 2 and NR 8 R 9 independently of one another represent pyrrolidino, piperazino, N-methylpiperazino or piperidino,
• R 10 represents hydrogen, cyano, methyl, ethyl, propyl, butyl, phenyl, tolyl, methoxyphenyl or xylyl
• R 14 and R 15 independently represent hydrogen, methyl, ethyl, propyl, butyl, cyanoethyl, hydroxyethyl, hydroxypropyl, cyclopentyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, xylyl, benzyl, phenethyl, phenylpropyl, pyridyl or a radical of the formula
• NR R represents pyrrolidino, morpholino, piperazino, N-methylpiperazino or piperidino,
• R 16 and R 16 independently of one another represent hydrogen, methyl, ethyl, methoxy, ethoxy or chlorine or
• R 16 ; R 15 and / or R 16 ' ; R 14 form a - (CH 2 ) 2 - or - (CH 2 ) 3 bridge, which can be substituted by up to 3 methyl groups,
• R 17 for hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, cyano, methoxycarbonyl, ethoxycarbonyl, O-CO-R 22 , NR 23 -CO-R 22 , O-SO 2 -R 22 or NR 23 -SO 2 -R 22 stands,
• R 22 represents methyl, ethyl, trifluoromethyl, cyclopentyl, cyclohexyl, benzyl, methoxy, ethoxy, dimethylamino, diethylamino, methylamino, phenyl, phenoxy, anilino or pyridyl,
• R 23 represents hydrogen or methyl
• Y 1 to Y 3 represent CH, n stands for 0 or 1 and
• 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, 600 to 680 nm or 750 to 820 nm.
• Contrast between written and unwritten points on the data carrier is achieved by the change in reflectivity of the amplitude and the phase of the incident light by the optical properties of the information layer which have changed after thermal degradation.
• the cationic ammoheterocyclic dyes are preferably applied to the optical data carrier by spin coating.
• the cationic ammoheterocyclic dyes can be mixed with one another or with other dyes with similar spectral properties.
• cationic dyes can be mixed with different anions.
• 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.
• 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, adhesive layers and protective films.
• the adhesive layers can be pressure sensitive.
• Pressure-sensitive adhesive layers mainly consist of acrylic adhesives.
• the invention further relates to a write-once optical data carrier, comprising a preferably transparent substrate, on the surface of which there is at least one information layer which can be written on with light, optionally one
• Reflective layer and / or optionally a protective layer are applied, which can be written and read with blue, red or infrared light, preferably laser light, the information layer comprising at least one of the abovementioned light-absorbing compounds and, if appropriate, a binder, wetting agent, stabilizers, thinners and sensitizers and contains other ingredients.
• the structure of the optical data carrier can be:
• 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
• the structure of the optical data carrier can preferably:
• Light preferably laser light, optionally a protective layer (4), optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
• a preferably transparent substrate (1) on the surface of which a protective layer (2), at least one information layer (3) which can be written on with light, preferably laser light, optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
• a transparent substrate (1) on the surface of which there is optionally a protective layer (2), at least one information layer (3) which can be written on with light, preferably laser light, optionally a protective layer (4), optionally an adhesive layer (5), and a transparent one 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 optical data carrier has, for example, the following layer structure (cf. FIG. 3): a preferably transparent substrate (21), an information layer (22), optionally a reflection layer (23), a protective layer (24).
• the invention further relates to optical data carriers according to the invention described with blue, red or infrared light, in particular laser light.
• Suitable cationic amino heterocyclic dyes are also listed in the following tables:
• a UV-curable acrylic lacquer was then applied by spin coating and cured using a UV lamp.
• the light reflected by the reflective layer of the disc was
• a signal-to-noise ratio C / N 36 dB was measured.
• the write power was applied as an oscillating pulse sequence, the disk being alternately irradiated for 1 ⁇ s with the above-mentioned write power P w and for 4 ⁇ s with the read power P r ⁇ 0.6 mW.
• the disc was irradiated with this oscillating pulse sequence until it had turned around once. The marking generated in this way was then read out with the reading power P r and the above-mentioned signal-to-noise ratio C / N was measured.

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• 2002
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