WO2007020191A1 - Colorants a base de complexes metalliques azoiques a base d'acide thiobarbiturique et utilisation de ceux-ci dans des couches optiques destinees a l'enregistrement de donnees optiques - Google Patents

Colorants a base de complexes metalliques azoiques a base d'acide thiobarbiturique et utilisation de ceux-ci dans des couches optiques destinees a l'enregistrement de donnees optiques Download PDF

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Publication number
WO2007020191A1
WO2007020191A1 PCT/EP2006/064938 EP2006064938W WO2007020191A1 WO 2007020191 A1 WO2007020191 A1 WO 2007020191A1 EP 2006064938 W EP2006064938 W EP 2006064938W WO 2007020191 A1 WO2007020191 A1 WO 2007020191A1
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alkyl
independently
halogen
formula
substituted
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PCT/EP2006/064938
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English (en)
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Jean-Christophe Graciet
Pascal Steffanut
Lars LÜCKE
Martin Alexander Winter
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Clariant International Ltd
Clariant Finance (Bvi) Limited
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Publication of WO2007020191A1 publication Critical patent/WO2007020191A1/fr

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    • 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
    • G11B7/2492—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 neutral 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo 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
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    • 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
    • G11B7/2467—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 azo-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
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    • G11B2007/25705—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials
    • G11B2007/25706—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials containing transition metal elements (Zn, Fe, Co, Ni, Pt)
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    • G—PHYSICS
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    • G11B2007/25713—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials containing nitrogen
    • G—PHYSICS
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    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
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    • 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
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    • G11B7/257—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
    • G11B2007/25705—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials
    • G11B2007/25715—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials containing oxygen
    • 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
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    • G11B7/257—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
    • G11B2007/25705—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials
    • G11B2007/25716—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials containing sulfur
    • 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
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    • G11B7/253—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 substrates
    • G11B7/2533—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 substrates comprising resins
    • 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
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    • 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
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    • G11B7/257—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
    • G11B7/2572—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of organic materials
    • G11B7/2575—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of organic materials resins
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Definitions

  • the present invention relates to thiobarbituric acid based azo metal complex dyes and their use in optical layers for optical data recording, preferably for optical data recording using a laser with a wavelength up to 450 nm.
  • the invention further relates to a write once read many (WORM) type optical recording medium capable of recording and reproducing information with radiation of blue laser, which employs a thiobarbituric acid based azo metal complex dye in the optical layer.
  • WORM write once read many
  • CD-R recordable compact discs
  • DVD-R recordable digital versatile discs
  • CD-R recordable compact discs
  • D-R recordable digital versatile discs
  • dyes are suitable in their respective fields with the laser wavelength criteria.
  • Other general requirements for dye media are strong absorption, high reflectance, high recording sensitivity, enhancement of photosensitivity, low thermal conductivity as well as light and thermal stabilities, durability for storage or non-toxicity. Furthermore sharp thresholds of thermal decomposition and steep absorption slopes are desirable.
  • these dyes have to be suitable for the spin coating process to prepare thin films, i.e. they have to be sufficiently soluble in the organic solvents generally applied in the spin coating process.
  • WORM type and erasable type optical recording media reproduce information by detecting variations in the reflectivity caused by physical deformation, by alterations of optical characteristics as well as by phase and magnetic properties of a recording layer before and after the recording.
  • CD-R Recordable compact discs
  • DVD digital versatile discs
  • DVD-R with increased information storage capabilities up to 4.7 GBytes have been commercialized.
  • the DVD-R technology adopts as a light source a red diode laser with a wavelength of 630-670 nm. Thereby the pit size and track interval can be reduced, increasing the information storage capacity by up to 6-8 times compared to CD-R's.
  • Blu-ray ® discs (Blu-ray ® disc is a standard developed by Hitachi Ltd., LG Electronics Inc., Matsushita Electric Industrial Co. Ltd., Pioneer Corporation, Royal Philips Electronics, Samsung Electronics Co. Ltd., Sharp Corporation, Sony Corporation, Thomson Multimedia) or HD-DVD discs (a standard developed by Toshiba and NEC) are going to be the next milestone in optical recording technology.
  • the data storage may be increased up to 27 Gigabytes per recording layer for a 12 cm diameter disc.
  • a blue diode laser with a wavelength of 405 nm GaN or SHG laser diodes
  • the pit size and track interval can be further reduced, again increasing the storage capacity by an order of magnitude.
  • An optical data recording media generally comprises a substrate and a recording layer, the optical layer.
  • a substrate usually discs or wavers of organic polymeric materials are used as substrates.
  • Preferred substrates are polycarbonate (PC) or polymethylmethacrylate (PMMA).
  • the substrate has to provide an even and uniform surface of high optical quality.
  • the optical layer is deposited thereon in a thin and uniform film of high optical quality and defined thickness.
  • a reflective layer e.g. aluminum, gold or copper, is deposited upon the optical layer.
  • Advanced optical data recording media may comprise further layers, such as protective layers, adhesive layers or additional optical layers.
  • the material is usually deposited by spin coating, vacuum evaporation, jet coating, rolling coating or soaking.
  • the preferred process in industry is spin coating to form an optical layer of about 70 nm to 250 nm thickness.
  • the material of the optical layer has to be highly soluble in organic solvents.
  • Aminoantipyrine based dyes of the below general formulae are known for many years (see for example DE 1076078 A and US 2,993,884):
  • azo derivatives behave generally as monobasic tridentate ligands towards metals like nickel, copper or manganese.
  • thiobarbituric acid based azo metal complex dyes as described below are useful as dye compounds in optical layers for optical data recording media.
  • halogen represents F, Cl, Br or I, preferably F, Cl or Br, more preferably F or Cl, even more preferably Cl, if not otherwise stated;
  • alkyl represents linear and branched alkyl; and
  • alkoxy represents linear and branched alkoxy; any alkyl and cycloalkyl groups being unsubstituted or substituted by one or more halogen atoms (preferably halogenated alkyl are selected from the group consisting of CF 3 , CF 2 CF 3 , CF 2 CF 2 CF 3 , chloromethyl); if not otherwise stated.
  • M represents a metal atom
  • A is a five or six membered N-heteroaromatic cycle, optionally fused to a benzene ring;
  • R 1 , R 2 and R 7 are independently from each other selected from hydrogen, C 1-10 alkyl, C 5-10 cycloalkyl, the alkyl groups being optionally substituted by halogen; C 1-10 alkoxy, C 1-10 dialkylamino, unsubstituted phenyl or substituted phenyl (with 1 to 4 substituents being independently from each other selected from halogen, C 1-10 alkyl or nitro), unsubstituted or substituted benzyl (with 1 to 4 substituents being independently from each other selected from halogen, C 1-10 alkyl or nitro);
  • R 3 and R 8 are independently from each other selected from hydrogen, C 1-10 alkyl, C 5-10 cycloalkyl, the alkyl groups being optionally substituted by halogen
  • halogenated alkyl are selected from the group consisting of CF 3 , CF 2 CF 3 , CF 2 CF 2 CF 3 , chloromethyl); C 1-10 alkoxy, unsubstituted phenyl or substituted phenyl (with 1 to 4 substituents being independently from each other selected from halogen, C 1-10 alkyl or nitro), unsubstituted benzyl or substituted benzyl (with 1 to 4 substituents being independently from each other selected from halogen, C 1-10 alkyl or nitro), carboxy,C 1-10 alkyl carboxylate, NH- C 1-10 alkyl or NH-SO 2 - C 1-10 alkyl, CN;
  • R 4 and R 9 are independently from each other selected from H, C 1-10 alkyl, C 5-10 cycloalkyl, the alkyl groups being substituted by halogen; unsubstituted benzyl or substituted benzyl (with 1 to 4 substituents being independently from each other selected from halogen, C 1-10 alkyl or nitro);
  • R ⁇ R e R 10 and R 11 are independently from each other selected from hydrogen, Cl, CN, Br, Ci-4 alkyl, the alkyl groups being optionally substituted by halogen (preferably halogenated alkyl are selected from the group consisting of CF 3 , CF 2 CF 3 , CF 2 CF 2 CF 3 , chloromethyl), C 1- 4 -alkoxymethyl or phenoxymethyl, NO 2 or sulfonamide.
  • the subject of the invention is a compound of formula (I), wherein M is selected from the group consisting of Ni, Cu, Co, Zn, Al, Fe, Pd, Pt, Cr, Mn; A is selected to form one of the following groups
  • R 1 , R 2 R 7 and R 16 are independently from each other selected from H, CH 3 , C 2 H 5 , C 3 H 7 , C 4 Hg , unsubstituted phenyl or substituted phenyl (with 1 to 3 substituents being independently from each other selected from halogen or C 1-10 alkyl); R 3 and R 8 are independently from each other selected from hydrogen, CH 3 , C 2 H 5 ,
  • R 4 and R 9 are independently from each other selected from H, C 1-4 alkyl, unsubstituted benzyl or substituted benzyl (with 1 to 3 substituents being independently from each other selected halogen, C 1-10 alkyl or nitro);
  • R 5 , R 6 , R 10 and R 11 are independently from each other selected from hydrogen, Cl,
  • R 12 is selected from H, CH 3 , C 2 H 5 ;
  • R 13 are independently from each other selected from hydrogen, Ci-I 0 alkyl, C 5- I 0 cycloalkyl, the alkyl groups being optionally substituted by halogen (preferably halogenated alkyl are selected from the group consisting of CF 3 , CF 2 CF 3 , CF 2 CF 2 CF 3 , chloromethyl); Ci-I 0 alkoxy, unsubstituted phenyl or substituted phenyl (with 1 to 4 substituents being independently from each other selected from halogen, Ci-I 0 alkyl or nitro), unsubstituted benzyl or substituted benzyl (with 1 to 4 substituents being independently from each other selected from halogen, Ci-I 0 alkyl or nitro), carboxy,Ci-io alkyl carboxylate, NH- Ci-I 0 alkyl or NH-SO 2 - Ci-I 0
  • subject of the present invention is a compound of formula (I), wherein
  • M is selected from the group consisting of Ni, Cu, Co, Zn, Cr; A is selected to form one of the following groups N R 16
  • R 1 , R 2 R 7 and R 16 are independently from each other selected from H, CH 3 , C 2 H 5 ,
  • R 3 and R 1 are independently from each other selected from H, CH 3 , C 2 H 5 , CF 3 ,
  • R 4 and R" are independently from each other selected from H, CH 3 , C 2 H 5 ;
  • R 5 , R 6 , R 10 and R 11 are independently from each other selected from hydrogen, Cl,
  • R 1 12 and R , 13 are independently from each other selected from H, CH 3 , C 2 H 5 .
  • A is selected to form one of the following groups
  • R 5 , R 6 , R 10 and R 11 are independently from each other selected from hydrogen, Cl, CF 3 , CF 2 CF 3 , CF 2 CF 2 CF 3 .
  • R 1 , R 2 R 7 and R 16 are independently from each other selected from H, CH 3 , C 2 H 5 , phenyl or substituted phenyl, with one or two substituents being independently from each other selected from Cl, CH 3 and C 2 H 5 .
  • R 1 , R 2 R 7 and R 16 are independently from each other selected from H, CH 3 , C 2 H 5 , phenyl, chlorophenyl and dichlorophenyl.
  • the subject of the invention is a compound of formula (II) or (III)
  • M is selected from the group consisting of Ni, Cu, Co, Zn, Al, Fe, Pd, Pt, Cr and Mn; and R 14 and R 15 are independently from each other selected from hydrogen and Cl.
  • the subject of the invention is a compound of formula (II) or (III) wherein M is selected from nickel, zinc, copper, cobalt, chromium, and wherein R 14 and R 15 are defined as above.
  • the thiobarbituric acid based azo metal complex dyes of the invention are prepared by complexation reaction of one equivalent of a aminoantipyrine based azo ligand of the formula (IV) and one equivalent of a aminoantipyrine based azo ligand of the formula (V) with a one equivalent of a metal salt, wherein A and R 1 to R 11 are defined as above with all their preferred embodiments.
  • the metal salt is a divalent metal salt with the metal selected preferably of the group consisting of Ni, Cu, Co, Zn, Al, Fe, Pd, Pt, Cr, Mn.
  • Divalent salts of these metals are preferably sulfates, chlorides and acetates and their respective hydrates.
  • Preferred metal salts are derived from Ni, Cu, Co, Zn, Cr and Mn.
  • Preferred metal salts are for example nickel-, copper-, cobalt-, zinc-, chromium- or manganese sulfate; nickel-, copper-, cobalt-, zinc-, chromium- or manganese chloride or nickel-, copper-, cobalt-, zinc-, chromium- or manganese acetate and their respective hydrates, especially preferably Cu(SO 4 ) 2 , CuCl 2 , Ni(OAc) 2 *4 H 2 O, NiCl 2 *6 H 2 O, Co(SO 4 ) 2 , Zn(OAc) 2 *4 H 2 O.
  • metal salts are nickel acetate tetrahydrate Ni(OAc) 2 *4 H 2 O, copper sulfate Cu(SO 4 ) 2 , cobalt sulfate Co(SO 4 ) 2 , zinc acetate tetrahydrate Zn(OAc) 2 *4 H 2 O.
  • the azo ligand is prepared by azo coupling reaction of the respective diazo component and the respective coupling agent.
  • the diazo component is prepared by diazotization reaction of the respective amine compound.
  • the coupling reaction may be carried out in water, non-aqueous solvents and in mixtures thereof.
  • Non-aqueous solvents are alcohols such as methanol, ethanol, propanol, butanol, pentanol, etc., dipolar aprotic solvents such as DMF, DMSO, NMP and water-immiscible solvents such as toluene or chlorobenzene.
  • the coupling is preferably carried out in a stochiometric ratio of coupling component and diazo component.
  • the coupling is generally done at temperatures between -30°C to 100°C, preference being given to temperatures of -10°C to 30°C, and particular preference to temperatures of -5°C to 20°C.
  • the coupling may be carried out in an acidic as well as an alkaline medium. Preference is given to pH ⁇ 10, particular preference to pH between 3 to 9.0 .
  • the complexes of formula (I) are prepared by reaction of a solution of one equivalent of a metal salt with a boiling solution of two equivalents of the dye ligand. It is possible to use more than one dye ligand, naturally in this case the combined amounts of the dye ligands should preferably be equal to two equivalents of the metal salts. Of course it is also possible to use more than one metal salt, for example a mixture of 2 or 3 metal salts, in the required stochiometric amounts; and a combination of these measures is also possible.
  • the precipitate is isolated following standard methods.
  • the solvents used in the process are water, solvents and mixtures thereof.
  • the solvents are preferably selected from the group consisting of C 1-8 alcohols, alkylnitriles, aromatics, dimethylformamide, N-methylpyrolidone.
  • Most preferred solvents used in the process are C 1-8 alcohols.
  • a further subject of the invention is therefore a process for preparing the thiobarbituric acid based azo metal complexes by a complexation reaction of the respective azo ligands with metal salts as described above.
  • the subject of the invention is further the use of the compounds of formula (I) as defined above and the use of the compounds of formula (I) in all the preferred aspects of the formula (I) as described above, in an optical layer for optical data recording.
  • the subject of the invention is further the use of the compounds of formula (I) as defined above and the use of the compounds of formula (I) in all the preferred aspects of the formula (I) as described above, as a dye in an optical layer for optical data recording.
  • the subject of the present invention is further an optical layer comprising a compound of formula (I) as described above and the use of said optical layer for optical data recording media.
  • An optical layer according to the invention may also comprise a mixture of two or more, preferably of two or three, more preferably of two dye compounds of formula (I) as defined above.
  • the thiobarbituric acid based azo metal complex dye compounds of formula (I) provide for particularly preferable properties when used in optical layers for optical data recording media according to the invention.
  • the invention relates to a method for producing optical layers on a substrate comprising the following steps
  • the substrate which functions as support for the layers applied thereto, is advantageously semi-transparent (transmittance T>10%) or preferably transparent (transmittance T>90%).
  • the support can have a thickness of from 0.01 to 10 mm, preferably from 0.1 to 5 mm.
  • Suitable substrates are, for example, glass, minerals, ceramics and thermosetting or thermoplastic plastics.
  • Preferred supports are glass and homo- or co-polymeric plastics.
  • Suitable plastics are, for example, thermoplastic polycarbonates, polyamides, polyesters, polyacrylates and polymethacrylates, polyurethanes, polyolef ⁇ ns, polyvinyl chloride, polyvinylidene fluoride, polyimides, thermosetting polyesters and epoxy resins.
  • the most preferred substrates are polycarbonate (PC) or polymethylmethacrylate (PMMA).
  • the substrate can be in pure form or may also comprise customary additives, for example UV absorbers as light-stabilizers for the optical layer.
  • the substrate is advantageously transparent over at least a portion of the range from 350 to 500 nm, so that it is permeable to at least 90% of the incident light of the writing or readout wavelength.
  • Organic solvents are selected from C 1-8 alcohol, halogen substituted C 1-8 alcohols, C 1-8 ketone, C 1-8 ether, halogen substituted C 1-4 alkane, nitriles, preferably acetonitrile, or amides, or mixtures thereof.
  • Preferred C 1-8 alcohols or halogen substituted C 1-8 alcohols are for example methanol, ethanol, isopropanol, diacetone alcohol (DAA), 2,2,3, 3-tetrafluoropropanol, trichloroethanol, 2-chloroethanol, octafluoropentanol or hexafluorobutanol, more preferred 2,2,3, 3-tetrafluoro-l-propanol.
  • Preferred C 1-8 ketones are for example acetone, methylisobutylketone, methylethylketone, or 3-hydroxy-3-methyl-2-butanone.
  • Preferred halogen substituted C 1-4 alkanes are for example chloroform, dichloromethane or 1-chlorobutane.
  • Preferred amides are for example dimethylformamide or dimethylacetamide.
  • Suitable coating methods are, for example, immersion, pouring, brush-coating, blade- application and spin-coating, as well as vapor-deposition methods carried out under a high vacuum.
  • pouring methods solutions in organic solvents are generally used.
  • solvents are employed, care should be taken that the supports used are insensitive to those solvents.
  • the optical layer is preferably applied by spin- coating with a dye solution.
  • Optical layer also called dye layer or recording layer
  • the optical layer is preferably arranged between the transparent substrate and the reflecting layer.
  • the thickness of the recording layer is from 10 to 1000 nm, preferably from 30 to 300 nm, more preferably from 70 to 250 nm, especially about 80 nm, for example from 60 to 120 nm.
  • the optical layer comprises a compound of formula (I) preferably in an amount sufficient to have a substantial influence on the refractive index, for example at least 30% by weight of the total weight of the optical layer, more preferably at least 60% by weight, most preferably at least 80% by weight.
  • stabilizers for example 1 O 2 -, triplet- or luminescence quenchers, melting-point reducers, decomposition accelerators or any other additives that have already been described in optical data recording media.
  • stabilizers or fluorescence-quenchers are added if desired.
  • Stabilizers, 1 O 2 -, triplet- or luminescence-quenchers are, for example, metal complexes of N- or S-containing enolates, phenolates, bisphenolates, thiolates or bisthiolates, hindered phenols and derivatives thereof such as o-hydroxyphenyl-triazoles or -triazines or other UV absorbers, such as hindered amines (TEMPO or HALS, as well as nitroxides or NOR-HALS), and also as cations diimmonium, ParaquatTM or Orthoquat salts, such as ® Kayasorb IRG 022, ® Kayasorb IRG 040, optionally also as radical ions, such as N 5 N 5 N ,N'-tetrakis(4-dibutylaminophenyl)-p-phenylene amine-ammonium hexafluorophosphate, hexafluoroantimonate or perchlorate.
  • the present invention provides for an optical layer suitable for high-density recording material, e.g. of the WORM disc format, in a laser wavelength range of from 350-450nm, preferably around 405 nm.
  • a method for producing an optical data recording medium comprising an optical layer according to the invention usually comprises the following additional steps
  • the application of the metallic reflective layer is preferably effected by sputtering, vapor-deposition in vacuum or by chemical vapor deposition (CVD).
  • the sputtering technique is especially preferred for the application of the metallic reflective layer.
  • Reflecting materials suitable for the reflective layer include especially metals, which provide good reflection of the laser radiation, used for recording and playback, for example the metals of Main Groups III, IV and V and of the Sub-groups of the Periodic Table of the Elements.
  • Special preference is given to a reflective layer of aluminum, silver, copper, gold or an alloy thereof, on account of their high reflectivity and ease of production.
  • Cover layer also called protective layer
  • cover layer Materials suitable for the cover layer include plastics, which are applied in a thin layer to the support or the uppermost layer either directly or with the aid of adhesive layers.
  • the material of the cover layer may for example be the same as the material of the substrate. It is advantageous to select mechanically and thermally stable plastics having good surface properties, which may be modified further.
  • the plastics may be thermosetting plastics and thermoplastic plastics. Preference is given to radiation-cured (e.g. using UV radiation) protective layers, which are particularly simple and economical to produce.
  • radiation-curable materials are known. Examples of radiation-curable monomers and oligomers are acrylates and methacrylates of diols, triols and tetrols, polyimides of aromatic tetracarboxylic acids and aromatic diamines having Ci-C 4 alkyl groups in at least two ortho-positions of the amino groups, and oligomers with dialkylmaleinimidyl groups, e.g. dimethyl maleinimidyl groups.
  • a high-density optical data recording medium therefore preferably is a recordable optical disc comprising: a first substrate, which is a transparent substrate with grooves, a optical layer (recording layer), which is formed on the first substrate surface using the compounds of formula (I), a reflective layer formed on the optical layer, a second substrate, which is a transparent substrate connected to the reflective layer with an attachment layer.
  • the optical data recording medium according to the invention is preferably a recordable optical disc of the WORM type. It may be used, for example, as a playable HD-DVD (high density digital versatile disc) or Blu-ray ® disc, as storage medium for a computer or as an identification and security card or for the production of diffractive optical elements, for example holograms.
  • WORM high density digital versatile disc
  • Blu-ray ® disc as storage medium for a computer or as an identification and security card or for the production of diffractive optical elements, for example holograms.
  • optical data recording media according to the invention may also have additional layers, for example interference layers. It is also possible to construct optical data recording media having a plurality of (for example two) recording layers. The structure and the use of such materials are known to the person skilled in the art. Preferred, if present, are interference layers that are arranged between the recording layer and the reflecting layer and/or between the recording layer and the substrate and consist of a dielectric material of TiO 2 , Si 3 N 4 , ZnS or silicone resins.
  • optical data recording media according to the invention can be produced by processes known in the art.
  • the structure of the optical data recording medium according to the invention is governed primarily by the readout method; known function principles include the measurement of the change in the transmission or, preferably, in the reflection, but it is also known to measure, for example, the fluorescence instead of the transmission or reflection.
  • the optical data recording medium is structured for a change in reflection
  • the following structures can be used: transparent support / recording layer (optionally multilayered) / reflective layer and, if expedient, protective layer (not necessarily transparent); or support (not necessarily transparent) / reflective layer / recording layer and, if expedient, transparent protective layer.
  • transparent support / recording layer optionally multilayered
  • reflective layer and, if expedient, protective layer (not necessarily transparent); or support (not necessarily transparent) / reflective layer / recording layer and, if expedient, transparent protective layer.
  • the light detector is located on the same side as the light source.
  • the first-mentioned structure of the recording material to be used according to the invention is generally preferred.
  • the optical data recording medium is structured for a change in light transmission, the following different structure comes into consideration: transparent support/ recording layer (optionally multilayered) and, if expedient, transparent protective layer.
  • the light for recording and for readout can be incident either from the support side or from the recording layer side or, where applicable, from the protective layer side, the light detector in this case always being located on the opposite side.
  • Suitable lasers are those having a wavelength of 350-500 nm, for example commercially available lasers having a wavelength of 405 to 414 nm, especially semi-conductor lasers.
  • the recording is done, for example, point for point, by modulating the laser in accordance with the mark lengths and focusing its radiation onto the recording layer. It is known from the specialist literature that other methods are currently being developed which may also be suitable for use.
  • the process according to the invention allows the storage of information with great reliability and stability, distinguished by very good mechanical and thermal stability and by high light stability and by sharp boundary zones of the pits. Special advantages include the high contrast, the low jitter and the surprisingly high signal/noise ratio, so that excellent readout is achieved.
  • the readout of information is carried out according to methods known in the art by registering the change in absorption or reflection using laser radiation.
  • the invention accordingly relates also to a method for the optical data recording, storage and playback of information, wherein an optical data recording medium according to the invention is used.
  • the recording and the playback advantageously take place in a wavelength range of from 350 to 500 nm.
  • the compounds of formula (I) provide for particularly preferable properties when used in optical layers for optical data recording media according to the invention. They possess the required optical characteristics, demonstrated when used in the form of a solid film: • an advantageously homogeneous, amorphous and low-scattering optical layer,
  • a high refractive index at the longer wavelength flank of the absorption band which preferably achieves n values of the refractive index of from 1.0 to 3.0 in the range of from 350 to 500 nm, • a high sensitivity under laser radiation of high power density and good playback characteristics in the desired spectral range,
  • Recording performance of a compound is related to specific parameters measured on disc like:
  • the absorption edge is surprisingly steep even in the solid phase.
  • the compounds of formula (I) also show a narrow decomposition temperature of 220- 350°C, fitting with the thermal requirements. Additionally, these compounds show a high solubility in organic solvents, which is ideal for the spin-coating process to manufacture optical layers.
  • the recording media according to the invention may also have additional layers, for example interference layers. It is also possible to construct recording media having a plurality of (for example two) recording layers. The structure and the use of such materials are known to the person skilled in the art.
  • Preferred, if present, are interference layers that are arranged between the recording layer and the reflecting layer and/or between the recording layer and the substrate and consist of a dielectric material OfTiO 2 , Si 3 N 4 , ZnS or silicone resins.
  • These recording media according to the invention can be produced by processes known in the art.
  • ⁇ max and ⁇ values of a compound are determined by using an UV- vis spectrophotometer, the compound was dissolved in CH2CI2, DMSO or in tip. The values are obtained by balancing the measurements performed on compound solutions at three different concentrations.
  • Thermal Decomposition Decomposition point (DP) and heat release (HR)
  • DP Decomposition point
  • HR heat release
  • the compound is incorporated into a sealed aluminum pan. Analysis conditions are as following: Temperature range from 25 to 400°C, heating rate 10°C/min, nitrogen flow of 50 ml/min. Values are determined by single measurement.
  • PRSNR PRSNR
  • Annex H of Version 0.9 PART 1 Physical Specifications
  • DVD Specifications for High Density Read-Only Disk
  • PRSNR and SbER are measured in a state in which information has been recorded in the adjacent tracks.
  • Ligand (1) A mixture of 20.7 g of 4-aminoantipyrine, 130 ml of water and 32 g of concentrated hydrochloric acid (30% w/w) was gradually admixed with 24.9 ml of sodium nitrite (33% w/v) at 0°C. After 1 hour of reaction at 0°C, the violet-pink diazotization solution was added drop wise to an alkaline solution of 20.4 g of l,3-diethyl-2-thiobarbituric acid while maintaining pH at 7.5-9 with sodium hydroxide (30% w/w). The batch was stirred 3 hours, then filtered with suction. The precipitate was washed with water and dried. 38.2 g of a ligand of formula (1) was obtained.
  • the optical and thermal properties of the compounds of formula (I) were studied.
  • the compounds of formula (I) showed high absorption at the desired wavelengths.
  • the shapes of the absorption spectra that still remain critical to the disc reflectivity and formation of clean mark edges, are composed of one major band, comprised in a range of from 350 to 500 nm.
  • n values of the refractive index were evaluated between 1.0 and 2.7. Light stabilities were found comparable to commercial dyes which are already stabilized with quenchers for the use in optical data recording. Sharp threshold of thermal decomposition within the required temperature range characterizes the compounds of formula (I) which are desirable for the application in optical layers for optical data recording.
  • a 100 ⁇ m thick silver layer is then applied to the recording layer by atomization.
  • a 6 ⁇ m thick protective layer of a UV curable photopolymer (650- 020, DSM) is applied thereto by means of spin coating.
  • a second substrate is provided to combine with the resin protection layer using an attachment layer. This completes the manufacturing of a high-density recordable optical disc, the optical data recording medium.
  • Evaluation tests are performed using an optical disk evaluation device available from Pulse Tech Co., Ltd.
  • the testing conditions are the following ones:
  • Constant linear velocity (CLV) 6.61 m/sec.
  • a test for evaluating a degree of degradation due to repetition reproduction is conducted for each of the write-once optical disks made for the described dye recording layers. Readings are carried out at a reading laser power of 0.4 mW and the degrees of degradation of PRSNR and SbER are then measured. Maximum cycle number was found within the specifications.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)

Abstract

L'invention concerne des colorants à base de complexes métalliques azoïques à base d'acide thiobarbiturique et l'utilisation de ceux-ci dans des couches optiques, aux fins d'enregistrement de données optiques, de préférence, d'enregistrement de données optiques au moyen d'un laser présentant une longueur d'ondes allant jusqu'à 450 nm. L'invention concerne également un support d'enregistrement optique de type non réinscriptible (WORM) capable d'enregistrer et de reproduire des informations au moyen d'un rayonnement de laser bleu, mettant en oeuvre un colorant à base de complexes métalliques azoïques à base d'acide thiobarbiturique dans la couche optique.
PCT/EP2006/064938 2005-08-15 2006-08-02 Colorants a base de complexes metalliques azoiques a base d'acide thiobarbiturique et utilisation de ceux-ci dans des couches optiques destinees a l'enregistrement de donnees optiques WO2007020191A1 (fr)

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EP05017706 2005-08-15

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WO2007020191A1 true WO2007020191A1 (fr) 2007-02-22

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1076078B (de) * 1958-02-06 1960-02-25 Ciba Geigy Verfahren zum Faerben und Bedrucken von im wesentlichen aus Polyacrylnitril bestehenden Fasern
US2993884A (en) * 1958-02-06 1961-07-25 Ciba Ltd Metal complexes of monoazo-dyestuffs
EP1191526A2 (fr) * 2000-08-25 2002-03-27 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Supports d'enregistrement optiques
US20020091241A1 (en) * 2000-11-02 2002-07-11 Industrial Technology Research Institute Azo-metal complex dye and method for producing the same and its use for a high density optical disc recording medium
US20040161701A1 (en) * 2000-02-10 2004-08-19 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenyujo Cyanine dyes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1076078B (de) * 1958-02-06 1960-02-25 Ciba Geigy Verfahren zum Faerben und Bedrucken von im wesentlichen aus Polyacrylnitril bestehenden Fasern
US2993884A (en) * 1958-02-06 1961-07-25 Ciba Ltd Metal complexes of monoazo-dyestuffs
US20040161701A1 (en) * 2000-02-10 2004-08-19 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenyujo Cyanine dyes
EP1191526A2 (fr) * 2000-08-25 2002-03-27 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Supports d'enregistrement optiques
US20020091241A1 (en) * 2000-11-02 2002-07-11 Industrial Technology Research Institute Azo-metal complex dye and method for producing the same and its use for a high density optical disc recording medium

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