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WO2006136493A1 - Colorants azoiques a complexe metallifere a base d'antipyrine-indandione et leur utilisation dans des couches optiques pour l'enregistrement optique de donnees - Google Patents

Colorants azoiques a complexe metallifere a base d'antipyrine-indandione et leur utilisation dans des couches optiques pour l'enregistrement optique de donnees Download PDF

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Publication number
WO2006136493A1
WO2006136493A1 PCT/EP2006/062971 EP2006062971W WO2006136493A1 WO 2006136493 A1 WO2006136493 A1 WO 2006136493A1 EP 2006062971 W EP2006062971 W EP 2006062971W WO 2006136493 A1 WO2006136493 A1 WO 2006136493A1
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alkyl
optical
formula
compound
group
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PCT/EP2006/062971
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English (en)
Inventor
Jean-Christophe Graciet
Lars LÜCKE
Pascal Steffanut
Martin Alexander Winter
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Clariant Finance (Bvi) Limited
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Publication of WO2006136493A1 publication Critical patent/WO2006136493A1/fr

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    • 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
    • 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
    • G11B7/2467—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
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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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    • G11B7/2492—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
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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
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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
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Definitions

  • the present invention relates to antipyrine-indandione 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 only read many (WORM) type optical recording medium capable of recording and reproducing information with radiation of blue laser, which employs an antipyrine-indandione based azo metal complex dye in the optical layer.
  • WORM write only read many
  • CD-R recordable compact discs
  • DVD-R recordable digital versatile discs
  • CD-R recordable compact discs
  • D-R recordable digital versatile discs
  • CD-R recordable compact discs
  • D-R recordable digital versatile discs
  • 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 stability, 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 write once read many
  • 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 recordable digital versatile discs
  • 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. By these new specifications the data storage is increased up to 27 Gigabytes per recording layer for a 12 cm diameter disc. By adopting 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.
  • GaN or SHG laser diodes blue diode laser with a wavelength of 405 nm
  • 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. aluminium, 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.
  • Antipyrine azo dyes of the below general formulae are known for many years (see for example DE 1076078 A and US 2,993,884):
  • the present invention therefore relates to antipyrine-indandione based azo metal complex dyes and to their use in an optical layer comprising antipyrine-indandione based azo metal complex dyes as described below and to the use of said optical layers for optical data recording media. More particularly, the invention relates to a write only read many (WORM) type optical data recording medium capable of recording and reproducing information with radiation of blue laser of preferably 405 nm, which employs an antipyrine-indandione based azo metal complex dye in the optical layer.
  • WORM write only read many
  • the present invention is directed to a compound of formula (I),
  • M represents a divalent metal atom
  • R 1 represents O or S
  • R is selected from the group consisting of hydrogen, C 1-10 alkyl, C 5-10 cycloalkyl,
  • R is selected from C 1-10 alkyl, C 5-10 cycloalkyl, unsubstituted benzyl or substituted benzyl, with substituents being halogen, C 1-10 alkyl or nitro;
  • R 4 , R 5 , R 6 , R 7 , R 10 and R 11 are independently from each other selected from the group consisting of hydrogen, -Cl, -CN, -Br, -CF 3 , Ci- 4 -alkyl, chloromethyl,
  • Formular (I) can also be represented by other tautomeric forms.
  • the present invention is directed to a compound of formula (I) wherein
  • M is selected from the group consisting of Ni, Cu, Co, Zn, Al, Fe, Pd, Pt, Cr and
  • R 1 is oxygen
  • R 2 is selected from the group consisting of hydrogen, -CH 3 , -C 2 H 5 , -CH(CH 3 )2, phenyl, -CN and -CF 3
  • R 3 is selected from the group consisting of C 1-4 alkyl, unsubstituted benzyl and substituted benzyl, with substituents being halogen, C 1-10 alkyl or nitro
  • R 4 and R 5 are independently from each other selected from the group consisting of hydrogen, -Cl, -CN, -Br, -CF 3 , Ci- 4 -alkyl, chloromethyl, Ci- 4 -alkoxymethyl, phenoxymethyl, -NO 2 and sulfonamide, the sulfonamide selected from
  • R 6 , R 7 , R 10 and R 11 are independently from each other selected from hydrogen, -Cl,
  • the present invention is directed to a compound of formula
  • M is selected from the group consisting of Ni, Cu, Co, Zn and Cr;
  • R 1 is oxygen
  • R 2 is selected from H, CH 3 or C 2 H 5 ;
  • R 3 is selected from CH 3 or C 2 H 5 ;
  • R 4 , R 5 , R 6 , R 7 , R 10 and R 11 are independently from each other hydrogen, Cl, or methyl; and to the use of said compounds in an optical layer for optical data recording.
  • the present invention is directed to a compound of a formula selected from the group consisting of formulae (1), (2), (3), (4), (5), (6) and (7),
  • M represents a divalent metal atom
  • R 1 represents O or S
  • R 2 is selected from the group consisting of hydrogen, C 1-10 alkyl, C 5-10 cycloalkyl,
  • R 3 is selected from C 1-10 alkyl, C 5-10 cycloalkyl, unsubstituted benzyl or substituted benzyl, with substituents being halogen, C 1-10 alkyl or nitro;
  • R 4 , R 5 , R 6 , R 7 , R 10 and R 11 are independently from each other selected from the group consisting of hydrogen, -Cl, -CN, -Br, -CF 3 , Ci- 4 -alkyl, chloromethyl, Ci-4-alkoxymethyl, phenoxymethyl, -NO2 and sulfonamide, the sulfonamide selected from -SO 2 NH 2 , -SO 2 NHR 8 or -SO 2 N(R 8 ) 2 , with R 8 being Ci-Cn-alkyl; they are prepared by azo coupling reaction of the respective coupling component and diazo component, the latter being prepared by diazotization reaction of the respective amine component.
  • the coupling components and the amine components are known substances.
  • the azo coupling reaction may be carried out in water, and non-aqueous solvents and 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 chloro-benzene.
  • the azo coupling reaction is preferably carried out in a stoichiometric ratio of coupling component and diazo component.
  • the azo 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 10°C.
  • the azo coupling may be carried out in an acidic as well as an alkaline medium.
  • the compounds of formula (I) are prepared by complexing reaction of one equivalent of a divalent metal salt with two equivalents of the corresponding ligand of formula (II).
  • the metal salt is reacted in solution with a boiling solution of the ligands. It is possible to use a total of two equivalents of different ligands to yield heteroleptic compounds of formula (I). Usually a precipitate is formed, which 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.
  • a further subject of the invention is therefore a process for the preparation of the compounds of formula (I), as well as of the compounds of formula (I) in all the preferred aspects of the formula (I) as described above, by a complexing reaction of two equivalents of the compound of the formula (II) (azo ligands) with one equivalent of a divalent metal salts; with the azo ligands preferably prepared by a azo coupling reaction of the respective diazo components and the respective coupling component.
  • the subject of the invention is further the use of the compounds of formulae (I), (1), (2), (3), (4), (5), (6) and (7) 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), (1), (2), (3), (4), (5), (6) and (7) 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.
  • a further subject of the present invention is an optical layer comprising at least one compound of formula (I), (1), (2), (3), (4), (5), (6) or (7), also in all the preferred aspects of the formula (I), 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 compounds of formula (I) in all the preferred aspects of the formula (I).
  • a further subject of the invention is the use of said optical layers for optical data recording media, a further subject of the invention is an optical data recording medium comprising an optical layer comprising at least one compound of formula (I), (1), (2), (3), (4), (5), (6) or (7), also in all the preferred aspects of the formula (I).
  • the invention relates also to a method for producing said optical layers 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 especially 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 alcohols, 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 (TFP), 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, especially 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.
  • Cover layer also called protective 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 plasties may be thermosetting plasties and thermoplastic plasties. Preference is given to radiation-cured (e.g. using UV radiation) protective layers, which are particularly simple and economical to produce. A wide variety of radiation-curable materials are known.
  • radiation-curable monomers and oligomers are acrylates and methacrylates of diols, triols and tetrols, polyimides of aromatic tetracarboxylic acids and aromatic diamines having C 1-4 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. Readout methods
  • 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:
  • a decomposition point (DP) in the preferred temperature range between 220°C and 350°C, more precisely 250°C to 320°C
  • 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 250- 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.
  • ⁇ max and ⁇ values of a compound are determined by using an UV- vis spectrophotometer, the compound was dissolved in CH2CI2, DMSO or in TFP. 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.
  • Example 1 was carried out with the difference, that 1.34 g CuCl 2 instead of nickel acetate tetrahydrate was used.
  • Example 1 was carried out with the difference, that 2.19 g Zn(OAc) 2 ⁇ H 2 O instead of nickel acetate tetrahydrate was used.
  • Table A shows phys-chem data of the examples.
  • the optical and thermal properties of the compounds of formula (I) were studied.
  • the compounds of formula (I) show 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 offrom 350 to 500 nm.
  • n values of the refractive index were evaluated between 1.0 and 2.7.
  • 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 6 ⁇ m thick protective layer of a UV curable photopolymer (650-020, DSM) is applied thereto by means of spincoating.
  • 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

La présente invention concerne des colorants azoïques à complexe métallifère à base d'antipyrine-indandione et leur utilisation dans des couches optiques pour l'enregistrement optique de données, de préférence pour l'enregistrement optique de données au moyen d'un laser présentant une longueur d'onde pouvant atteindre 450 nm. L'invention concerne également un support d'enregistrement optique du type à écriture unique et à lecture multiple (WORM) permettant d'enregistrer et de reproduire des informations avec un rayonnement de laser bleu, et faisant appel à un colorant azoïque à complexe métallifère à base d'antipyrine-indandione situé dans la couche optique.
PCT/EP2006/062971 2005-06-22 2006-06-07 Colorants azoiques a complexe metallifere a base d'antipyrine-indandione et leur utilisation dans des couches optiques pour l'enregistrement optique de donnees WO2006136493A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8075976B2 (en) * 2005-07-14 2011-12-13 Mitsubishi Kagaku Media Co., Ltd. Optical recording medium, optical recording material and metal complex compound

Citations (4)

* 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
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 (4)

* 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
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

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8075976B2 (en) * 2005-07-14 2011-12-13 Mitsubishi Kagaku Media Co., Ltd. Optical recording medium, optical recording material and metal complex compound
US8309196B2 (en) 2005-07-14 2012-11-13 Mitsubishi Kagaku Media Co., Ltd. Optical recording medium, optical recording material and metal complex compound

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